Nuts and Seeds in Health and Disease Prevention

By Victor R Preedy and Ronald Ross Watson

Nuts and Seeds in Health and Disease Prevention, Second Edition investigates the benefits of nuts and seeds in health and disease prevention using an organizational style that will provide easy-access to information that supports identifying treatment options and the development of symptom-specific functional foods. This book examines seeds and nuts as agents that affect metabolism and other health-related conditions and explores the impact of compositional differences between various seeds and nuts, including differences based on country of origin and processing technique. Finally, the book includes methods for the analysis of seed and nut-related compounds.

Written for nutrition researchers, nutritionists, food scientists, government regulators of food, and students of agriculture, oils and feeds, nutrition and life sciences, this book is sure to be a welcomed resource.

• Identifies options and opportunities for improving health through the consumption of nut and seed products
• Provides easy access to information that supports the identification of treatment options
• Contains insights into health benefits that will assist in development of symptom-specific functional foods
• Examines seeds and nuts as agents that affect metabolism and other health-related conditions
• Explores the impact of compositional differences between various seeds and nuts, including differences based on country of origin and processing technique
• Includes methods for analysis of seed and nut-related compound

• Language: English
• Publisher: Academic Press
• Release date: May 17, 2020
• ISBN: 9780128216101

Book preview

Nuts and Seeds in Health and Disease Prevention

Second Edition

Editors

Victor R. Preedy

Ronald Ross Watson

Table of Contents

Cover image

Title page

Copyright

Contributors

Preface

Acknowledgments

I. Overview and General Themes

Chapter 1. Rambutan (Nephelium lappaceum L.) Seed and Its Fat

Introduction

Botanical Descriptions

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Applications in Health Promotion and Disease Prevention

Nephelium lappaceum Seed Fat (RSF) Characteristics, Potential Food, and Therapeutic Uses

RSF and Its Potential Food Uses for Health Promotion

Adverse Effects and Reactions, Allergies, and Toxicity

Summary Point

Chapter 2. Soursop Seed: Soursop (Annona muricata L.) Seed, Therapeutic, and Possible Food Potential

Introduction

Botanical Descriptions

Historical Cultivation and Usage

Present-day Cultivation and Usage

Applications in Health Promotion and Disease Prevention

Annona muricata Seed and Its Possible Potential for Food Use

Adverse Effects and Reactions, Allergies, and Toxicity

Summary Points

Chapter 3. Red Horse-Chestnut Seeds of Aesculus × Carnea: A New Way for Health and Food Design?

Introduction

Botanical Descriptions

Historical Cultivation and Usage

Red Horse-Chestnuts: Chemical Composition and Characterization

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions (Allergies and Toxicity)

Summary Points

Chapter 4. The African Breadfruit (Treculia africana) Decne Plant Seed: A Potential Source of Essential Food and Medicinal Phytoconstituents

Introduction

Botanical Description, Cultivation, and Usage

Fruit Processing and Seed Production

Nutritional Value and Food Uses of Treculia africana Seed

Antinutritional Compositions of African Breadfruit Seed

Applications to Health Promotion and Disease Prevention

Future Perspectives

Chapter 5. Perennial Horse Gram (Macrotyloma axillare) Seeds: Biotechnology Applications of Its Peptide and Protein Content – Bowman–Birk Inhibitors and Lectin

Introduction

Botanical Description

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Applications to Health Promotion and Disease Prevention – Biotechnology Applications of the Protein Seed Content

Adverse Effects and Reactions – Toxicity of Macrotyloma axillare

Summary Points

Chapter 6. Biological Properties of a Partially Purified Component of Neem Oil: An Updated and Revised Work

Introduction

Chapter 7. Bioactive Compounds of Oregano Seeds

Introduction

Botanical Description

Historical Cultivation and Use

Current Cultivation and Use

Applications for Health Promotion and Disease Prevention

Adverse Effects and Reactions, Allergies, and Toxicity

Summary Points

Chapter 8. Mango Seed: Mango (Mangifera indica L.) Seed and Its Fats

Introduction

Botanical Description

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions, Allergies, and Toxicity

Summary Points

II. Role of Seeds in Nutrition and Antioxidant Activities

Chapter 9. Biological Functions of Soyasaponins: The Potential Use to Improve Zinc Nutrition

Introduction

Zinc Nutrition and Health

Zinc Absorption in the Small Intestine and Zinc Transporter, ZIP4

Soybean Soyasaponin Bb Increases ZIP4 Abundance at the Apical Membrane

Conclusion

Chapter 10. Purple Wheat (Triticum sp.) Seeds: Phenolic Composition and Antioxidant Properties

Introduction

Botanical Description

Historical Cultivation of Purple Wheat

Phenolic Compounds in Purple Wheat Seeds

Methods of Analyses for Phenolic Contents and Phenolic Composition of Purple Wheat Seeds

Total Phenolic Content and Phenolic Acid Composition

Total Anthocyanin Content and Anthocyanin Composition

Total Flavonoid Content and Proanthocyanidin Composition

Processing and Utilization of Purple Wheat

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions (Allergies and Toxicity)

Summary Points and Future Perspectives

Chapter 11. Protective Role of Nigella sativa and Thymoquinone in Oxidative Stress: A Review

Introduction

Free Radicals and Antioxidant Defense

Chemical Constituents

Traditional Medicine

Pharmacological Properties

In vitro Antioxidant Activity of Nigella sativa

In vivo Antioxidant Activity of Nigella sativa

Conclusion

Chapter 12. Black Soybean Seed: Black Soybean Seed Antioxidant Capacity

Introduction

History, cultivation, and use

Anthocyanin

Antioxidant activity of black soybeans and black soybean–based food products

Health-promoting and disease-preventing effects of black soybean seed

Summary Points

Chapter 13. Fenugreek (Trigonella foenum) Seeds in Health and Nutrition

Introduction

Scientific Classification

Morphology of Seed

Earlier Cultivation of Fenugreek Seed

Current Cultivation

Phytochemical Constituents

Therapeutic Potential of Fenugreekenugreek Seed

Adverse Effects

Conclusion

Chapter 14. Tamarind (Tamarindus indica) Seeds in Health and Nutrition

Introduction

Botanical Description

Vernacular Names

Taxonomical Classification

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Nutritional Characterization of Tamarind Seeds

Phytochemicals Composition of Tamarind Seed

Biological Activities

Tamarind Seed Polysaccharide: a Promising Natural Excipient for Pharmaceuticals

Possible Adverse Effects and Reaction(s)

Summary of Key Point(s)

Chapter 15. Sesame Seed in Controlling Human Health and Nutrition

Introduction

Plant Profile

Chemical Composition

Pharmacological Applications

Sesame Oil Protects Against Lead-Plus-Lipopolysaccharide-Induced Acute Hepatic Injury

Conclusions

Chapter 16. Kancolla Seeds: High Nutritional Foods With Nutraceutical Properties

Introduction

Nutritional Values of Kancolla Seeds

Phytochemical Composition of Kancolla Seeds

Triterpenoid Saponins

Chapter 17. Health-promoting Potential and Nutritional Value of Madhuca longifolia Seeds

Introduction

Botanical Description and Cultivation

Composition of M. longifolia Seeds and Seed Cake

M. longifolia Butter Content and Composition

Applications of M. longifolia Butter

Applications of M. longifolia Seeds in Health Promotion and Disease Prevention

Adverse Effects (Allergies and Toxicity)

Conclusion

III. Fungal Infections on Seeds and Nuts and Health

Chapter 18. Ginkgo biloba Seeds: Antifungal and Lipid Transfer Proteins from Ginkgo biloba Nuts

Introduction

Lipid Transfer Proteins

Antifungal Proteins

Outlook

Chapter 19. Mycotoxins in Nuts and Seeds

Introduction

Natural Occurrence

Effect of Heat Processing

Toxicological Effects in Humans

Summary Points

IV. Nuts and Seeds in Disease Prevention and Therapy

Chapter 20. Lepidium sativum Seeds: Therapeutic Significance and Health-Promoting Potential

Introduction

Botanical Description and Cultivation

Chemical Composition of Lepidium sativum Seeds

Amino Acids Profile

Seed Oil Composition

Edible Applications of Lepidium sativum

Applications of Lepidium sativum to Health Promotion and Disease Prevention

Application As An Excipient in Pharmaceutical Dosage Form

Therapeutic Applications

Adverse Effects (Allergies and Toxicity)

Conclusions

Chapter 21. The Effects of Nuts on Metabolic Diseases and Disorders

Introduction

Fats

Macrominerals and Micromineral

Phenolic Compounds

Discussion

Chapter 22. Tea (Camellia oleifera) Seeds: Use of Tea Seeds in Human Health

Introduction

Botanical Description

Historical Cultivation and Usage

Present-day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions (Allergies and Toxicity)

Summary Points

Chapter 23. Effect of Nigella sativa on Blood Diseases: A Review

Introduction

Effect of Nigella sativa on Hematological Parameters

Induction of Anemia by Chemical Compounds

Clinical Studies

Conclusion

Chapter 24. Dermatological Effects of Nigella sativa and Its Constituent, Thymoquinone: A Review

Introduction

Methods

Anti-inflammatory and Immunomodulatory Properties of Nigella sativa and Its Constituent, TQ, Used to Treat Skin Ailments

In vitro and in Vivo Preclinical Studies

Clinical Studies

Anticancer

In vitro Studies

In vivo Studies

Wound Healing Effects

In vivo Studies

In vitro Studies

Antimicrobial Properties Against Skin Relevant Pathogens

Antibacterial

In vitro Studies

In vivo Studies

Antifungal Effects

Antiparasitic Properties

Conclusion

Chapter 25. Indian Mustard (Brassica juncea L.) Seeds in Health

Introduction

Botanical Descriptions

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions (Allergies and Toxicity)

Summary Points

Chapter 26. Potential Role of Seeds From India in Diabetes

Introduction

Seeds from Medicinal Plants and Their Role in Diabetes

Conclusion

Chapter 27. Lupine Seeds (Lupinus spp.): History of Use, Use as An Antihyperglycemic Medicinal, and Use as a Food Plant

Introduction

Botanical Description

Historical Medicinal Use

Current Medicinal Applications

Type 2 Diabetes

Fiber

Alkaloids

DPP-IV Inhibitors

Conglutins

Hyperlipidemia

Hypertension

Adverse Effects

Summary Points

Chapter 28. Cancer Chemopreventive Potential of Seed Proteins and Peptides

Introduction

Chapter 29. Use of Red Clover (Trifolium pratense L.) Seeds in Human Therapeutics

Introduction

Botanical Description

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions, Allergies, and Toxicity

Summary Points

Chapter 30. Milk Thistle Seeds in Health

Introduction

Botanical Descriptions

Historical Cultivation and Usage

Present-day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Summary Points

V. Extracts From Nuts and Seeds in Health

Chapter 31. Nut Consumption and Noncommunicable Diseases: Evidence From Epidemiological Studies

Introduction

Nuts and Metabolic Disorders

Nuts and Cardiovascular Disease Risk

Nuts and Cancer Risk

Nuts and Affective Disorders

Nuts and Cognitive Disorders

Conclusions

Chapter 32. Beneficial Effects of Nuts From India in Cardiovascular Disorders

Introduction

Cardiovascular Disorder

Almond and Cardiovascular Diseases

Cashew Nuts and Cardiovascular Diseases

Walnut and Cardiovascular Diseases

Pistachios and Cardiovascular Diseases

Peanuts and Cardiovascular Diseases

Conclusion

Chapter 33. Seeds as Herbal Drugs

Introduction

Medicinal Constituents of Seeds

Factors Influencing Medicinal Properties of Seeds

Seeds as Source of Medicinally Important Fixed Oils

Seeds as Herbal Drugs and Source of Medicinally Active Compounds

Summary Points

Chapter 34. Therapeutic Importance of Caster Seed Oil

Introduction

Castor Oil Is Unique Among all Fats and Oils

Soaps, Waxes, and Greases

Pharmacological and Medicinal Use

Other Health Benefits of Castor Oil

Side Effects of Castor Oil

Chapter 35. Coriandrum sativum L.: Characterization, Biological Activities, and Applications

Coriander Plant

Coriander Oil and Extracts

Coriander Biological Activities

Uses of Coriander Oil and Extracts

Concluding Remarks

Chapter 36. Proteinase Inhibitors From Buckwheat (Fagopyrum esculentum Moench) Seeds

Introduction

Botanical Descriptions

Present-day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions (Allergies and Toxicity)

Summary Points

Chapter 37. Pumpkin Seeds: Phenolic Acids in Pumpkin Seed (Cucurbita pepo L.)

Introduction

Historical Cultivation and Usage

Present-Day Cultivation and Usage

Applications to Health Promotion and Disease Prevention

Adverse Effects and Reactions (Allergies and Toxicity)

Summary Points

Chapter 38. Big Leaf Mahogany Seeds: Swietenia macrophylla Seeds Offer Possible Phytotherapeutic Intervention Against Diabetic Pathophysiology

Introduction

Description and Distribution

Ethnomedicinal Significance of Swietenia macrophylla Seeds

Swietenia macrophylla Seeds as a Potential Phytotherapeutic Agent Against Diabetes

Swietenia macrophylla Seeds Against Ailments Contribute in the Diabetic Pathogenesis

Toxicities and Contraindications of Swietenia macrophylla Seeds

Phytochemicals in Swietenia macrophylla Seeds

Antidiabetic Phytochemicals in Swietenia macrophylla Seeds

Metabolites in Swietenia macrophylla Seeds Against Pathogenesis Contribute in the Complications

Predicted Molecular Interactions of Swietenine with Signal Proteins and Detection of Drug-likeness

Molecular Docking

In silico ADMET Prediction

Conclusion

Index

Copyright

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Contributors

Kaveri Mahadev Adki,     Shobhaben Pratapbhai Patel School of Pharmacy and Technology Management, SVKM’s NMIMS, Mumbai, Maharashtra, India

Larissa Lovatto Amorin,     Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Franklin Brian Apea-Bah

Department of Food and Human Nutritional Sciences, University of Manitoba, Winnipeg, Manitoba, Canada

Richardson Centre for Functional Foods and Nutraceuticals, Smartpak, University of Manitoba, Winnipeg, Manitoba, Canada

Havva Atar,     Department of Biology, Faculty of Arts and Sciences, Zonguldak Bülent Ecevit University, Zonguldak, Turkey

Cecilia Baraldi,     Department of Life Sciences, University of Modena and Reggio Emilia, Modena, Italy

Mikhail A. Belozersky,     A.N. Belozersky Institute of Physico-Chemical Biology, Moscow State University, Moscow, Russia

Trust Beta

Department of Food and Human Nutritional Sciences, University of Manitoba, Winnipeg, Manitoba, Canada

Richardson Centre for Functional Foods and Nutraceuticals, Smartpak, University of Manitoba, Winnipeg, Manitoba, Canada

Sanjib Bhattacharya,     West Bengal Medical Services Corporation Ltd., Salt Lake City, Kolkata, West Bengal, India

Shovonlal Bhowmick,     Department of Chemical Technology, University of Calcutta, Kolkata, West Bengal, India

Anders Borgen,     Agrologica, Houvej, Mariager, Denmark

Letizia Bresciani,     Human Nutrition Unit, Department of Veterinary Science, University of Parma, Parma, Italy

H.N. Büyükkartal,     Ankara University, Faculty of Science, Department of Biology, Tandoğan, Ankara, Turkey

Chanya Chaicharoenpong,     Institute of Biotechnology and Genetic Engineering, Chulalongkorn University, Bangkok, Thailand

Phool Chandra,     School of Pharmaceutical Sciences, IFTM University, Lodhipur Rajput, Moradabad, Uttar Pradesh, India

Hatice Çölgeçen,     Department of Biology, Faculty of Arts and Sciences, Zonguldak Bülent Ecevit University, Zonguldak, Turkey

William de Castro Borges,     Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Ben O. de Lumen,     Department of Nutritional Science and Toxicology, University of California Berkeley, Berkeley, California, United States

Andressa Jacqueline de Oliveira,     Department of Biochemistry and Biotechnology, State University of Londrina, Londrina, Paraná, Brazil

Alessandra de Paula Carli

Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Universidade Federal dos Vales do Jequitinhonha e Mucuri, Instituto de Ciência, Engenharia e Tecnologia, Campus do Mucuri, Teófilo Otoni, Minas Gerais, Brazil

Marcos Aurélio de Santana,     Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Saikat Dewanjee,     Advanced Pharmacognosy Research Laboratory, Department of Pharmaceutical Technology, Jadavpur University, Kolkata, West Bengal, India

Irene Dini,     Pharmacy Department, Federico II University, Naples, Italy

Valentina I. Domash,     V.F. Kuprevich Institute of Experimental Botany of the National Academy of Sciences of Belarus, Minsk, Belarus

Celia Domeño,     Faculty of Veterinary Medicine, University of Zaragoza, Zaragoza, Spain

Fernanda C. Domingues,     CICS-UBI – Health Sciences Research Centre, University of Beira Interior, Covilhã, Portugal

Tarun K. Dua,     Department of Pharmaceutical Technology, University of North Bengal, Darjeeling, West Bengal, India

Yakov E. Dunaevsky,     A.N. Belozersky Institute of Physico-Chemical Biology, Moscow State University, Moscow, Russia

María del Carmen Durán-de-Bazúa,     Chemical Engineering Department, Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Ciudad de México, Mexico

Giorgia Foca

Department of Life Sciences, University of Modena and Reggio Emilia, Reggio Emilia, Italy

Interdepartmental Research Center BIOGEST-SITEIA, University of Modena and Reggio Emilia, Reggio Emilia, Italy

Fatemeh Forouzanfar

Neuroscience Research Center, Mashhad University of Medical Sciences, Mashhad, Iran

Department of Neuroscience, Faculty of Medicine, Mashhad University of Medical Sciences, Mashhad, Iran

Anil Bhanudas Gaikwad,     Laboratory of Molecular Pharmacology, Department of Pharmacy, Birla Institute of Technology and Science, Pilani Campus, Pilani, Rajasthan, India

Frixia Galán-Méndez,     Facultad de Ciencias Químicas, Universidad Veracruzana, Circuito Aguirre Beltrán s/n, Xalapa, Veracruz, Mexico

Justyna Godos,     Oasi Research Institute - IRCCS, Troina, Italy

Giuseppe Grosso,     Department of Biomedical and Biotechnological Sciences, University of Catania, Catania, Italy

Milton Hércules Guerra de Andrade,     Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Ken-ichi Hatano,     Division of Molecular Science, Faculty of Science and Technology, Gunma University, Kiryu, Gunma, Japan

Blanca Hernández-Ledesma,     Group of Food Proteins, Instituto de Investigación en Ciencias de la Alimentación (CIAL, CSIC-UAM, CEI UAM+CSIC), Madrid, Spain

María del Rosario Hernández-Medel,     Instituto de Ciencias Básicas, Universidad Veracruzana, Avenida Luis Castelazo Ayala s/n, Xalapa, Veracruz, Mexico

Melissa Tiemi Hirozawa,     Department of Biochemistry and Biotechnology, State University of Londrina, Londrina, Paraná, Brazil

Azar Hosseini,     Pharmacological Research Center of Medicinal Plants, Mashhad University of Medical Sciences, Mashhad, Razavi Khorasan Province, Iran

Hossein Hosseinzadeh

Department of Pharmacodynamics and Toxicology, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Razavi Khorasan Province, Iran

Pharmaceutical Research Center, Pharmaceutical Technology Institute, Mashhad University of Medical Sciences, Mashhad, Razavi Khorasan Province, Iran

Chia-Chien Hsieh,     School of Life Science, Undergraduate and Graduate Programs of Nutrition Science, National Taiwan Normal University, Taipei, Taiwan

Ignasius Radix A.P. Jati,     Department of Food Technology, Faculty of Agricultural Technology, Widya Mandala Catholic University Surabaya, Surabaya, East Java, Indonesia

Taiho Kambe,     Division of Integrated Life Science, Graduate School of Biostudies, Kyoto University, Kyoto, Japan

Natalya V. Khadeeva,     N.I. Vavilov Institute of General Genetics, Russian Academy of Sciences, Moscow, Russia

David H. Kinder,     College of Pharmacy, Ohio Northern University, Ada, OH, United States

Kathryn T. Knecht,     Associate Professor of Pharmaceutical Sciences, School of Pharmacy, Loma Linda University, Loma Linda, CA, United States

U. Koca,     Gazi University, Faculty of Pharmacy, Department of Pharmacognosy, Etiler, Ankara, Turkey

Vera Krimer-Malešević,     National Reference Laboratories, Belgrade, Serbia

Yogesh Anant Kulkarni,     Shobhaben Pratapbhai Patel School of Pharmacy and Technology Management, SVKM’s NMIMS, Mumbai, Maharashtra, India

Ankit Pravin Laddha,     Shobhaben Pratapbhai Patel School of Pharmacy and Technology Management, SVKM’s NMIMS, Mumbai, Maharashtra, India

Sonaly Cristine Leal,     Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Qin Liu,     School of Food Science and Engineering, Nanjing University of Finance and Economics, Nanjing, Jiangsu, China

Laura Maletti,     Department of Chemical and Geological Sciences, University of Modena and Reggio Emilia, Modena, Italy

Andrea Marchetti

Department of Chemical and Geological Sciences, University of Modena and Reggio Emilia, Modena, Italy

Interdepartmental Research Center BIOGEST-SITEIA, University of Modena and Reggio Emilia, Reggio Emilia, Italy

Daniela Martini,     DeFENS-Department of Food, Environmental and Nutritional Sciences, Division of Human Nutrition, University of Milan, Milan, Italy

Takuya Miyakawa,     Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan

Mohammad Moradzad,     Master of student of clinical biochemistry, department of clinical Biochemistry, Kurdistan University of medical sciences, Sanandaj, Iran, Kurdistan in Iran

Souvik Mukherjee,     Department of Pharmaceutical Sciences, Guru Ghasidas Vishwavidyalaya (A Central University), Bilaspur, Chhattisgarh, India

Aline Myuki Omori,     Department of Pathological Sciences, State University of Londrina, Londrina, Paraná, Brazil

Mario Augusto Ono,     Department of Pathological Sciences, State University of Londrina, Londrina, Paraná, Brazil

Hesham F. Oraby,     Department of Agronomy, Faculty of Agriculture, Zagazig University, Zagazig, Egypt

Folake Lucy Oyetayo,     Department of Biochemistry, Ekiti State University, Ado-Ekiti State University Ado-Ekiti, Nigeria

Victor Olusegun Oyetayo,     Department of Microbiology, Federal University of Technology, Akure, Nigeria

Dilipkumar Pal,     Department of Pharmaceutical Sciences, Guru Ghasidas Vishwavidyalaya (A Central University), Bilaspur, Chhattisgarh, India

Paramita Paul,     Department of Pharmaceutical Technology, University of North Bengal, Darjeeling, West Bengal, India

Yang Qiu,     Department of Food and Human Nutritional Sciences, University of Manitoba, Winnipeg, Manitoba, Canada

Arezoo Rajabian,     Pharmacological Research Center of Medicinal Plants, Mashhad University of Medical Sciences, Mashhad, Iran

Mohamed Fawzy Ramadan,     Agricultural Biochemistry Department, Faculty of Agriculture, Zagazig University, Zagazig, Egypt

Gianfranco Risuleo,     Dipartimento di Biologia e Biotecnologie Charles Darwin, Sapienza Università di Roma - Piazzale Aldo Moro, Roma Italy

Fabrizio Roncaglia,     Department of Chemical and Geological Sciences, University of Modena and Reggio Emilia, Modena, Italy

Neetu Sachan,     School of Pharmaceutical Sciences, IFTM University, Lodhipur Rajput, Moradabad, Uttar Pradesh, India

Achintya Saha,     Department of Chemical Technology, University of Calcutta, Kolkata, West Bengal, India

Patricia Sanchez,     College of Letters and Science, University of California, Los Angeles, CA, United States

Alexandre Gonçalves Santos,     Universidade Federal de Ouro Preto, Departamento de Ciências Biológicas, Núcleo de Pesquisas em Ciências Biológicas, Laboratório de Enzimologia e Proteômica, Campus Morro do Cruzeiro, Ouro Preto, Minas Gerais, Brazil

Elisabete Yurie Sataque Ono,     Department of Biochemistry and Biotechnology, State University of Londrina, Londrina, Paraná, Brazil

Simona Sighinolfi,     Department of Chemical and Geological Sciences, University of Modena and Reggio Emilia, Modena, Italy

Filomena Silva

ARAID – Agencia Aragonesa para la Investigación y el Desarrollo, Zaragoza, Spain

Faculty of Veterinary Medicine, University of Zaragoza, Zaragoza, Spain

CICS-UBI – Health Sciences Research Centre, University of Beira Interior, Covilhã, Portugal

Julio A. Solís-Fuentes,     Instituto de Ciencias Básicas, Universidad Veracruzana, Avenida Luis Castelazo Ayala s/n, Xalapa, Veracruz, Mexico

Vetriselvan Subramaniyan,     Associate Professor, Department of Pharmacology, Faculty of Medicine, MAHSA University, Bandar Saujana Putra, Selangor, Malaysia

Reka Szőllősi,     Department of Plant Biology, University of Szeged, Szeged, Hungary

Masakazu Takahashi,     Department of Bioscience and Biotechnology, Fukui Prefectural University, Fukui, Japan

Masaru Tanokura,     Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan

Lorenzo Tassi

Department of Chemical and Geological Sciences, University of Modena and Reggio Emilia, Modena, Italy

Interdepartmental Research Center BIOGEST-SITEIA, University of Modena and Reggio Emilia, Reggio Emilia, Italy

Alexander A. Vassilevski,     Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

Enas Mohamed Wagdi Abdel-Hamed,     Soil Science Department, Faculty of Agriculture, Zagazig University, Zagazig, Egypt

Preface

The objective of this book is to bring together scientific material relating to the health benefits and, where appropriate, adverse effects of nuts and seeds. In general, nuts and seeds are important not only from a nutritional point of view but also in terms of their putative medicinal or pharmacological properties. This book aims to describe these properties in a comprehensive way. However, at the same time, it is recognized that harmful effects also arise. Some nuts and seeds, for example, are poisonous when ingested in large quantities, but extracts have putative effects on tissues that may offer some therapeutic potential. Many of the nuts and seeds described in this book are components of traditional remedies without any present-day evidence to support their claims; their properties await rigorous elucidation and scientific investigation. Thus, the book embraces nuts and seeds in an unbiased way. The Editors also recognize that there is a wide interpretation of the terms nuts and seeds, and indeed some authorities have claimed that there are at least 12 seed types. The Editors have largely excluded cereals (grains) and other staple food crops, unless there was cause to include them, such as with buckwheat seeds. They have also selected some specific legumes, where there is some therapeutic potential in their extracts or interesting properties.

The book Nuts and Seeds in Health and Disease Prevention is divided into two parts. Part I, General Aspects and Overviews, contains holistic information, with sections on Overviews, Composition, Effects on Health, and Adverse Aspects. In Part II, Effects of Specific Nuts and Seeds, coverage is more specific. Each chapter in Part II contains sections entitled Botanical description, Historical cultivation and usage, Present-day cultivation and usage, Applications to health promotion and disease prevention (the main article), and, finally, Adverse effects and reactions. The Editors were faced with a difficult choice in organizing the chapters in Part II, and this was done using the simplest method available. Thus, in Part II, the nuts and seeds are listed alphabetically in terms of their common names, although each chapter contains full botanical terminology. We realize this is not perfect, for example, there are numerous types of cabbage seeds, and some nuts and seeds may have as many as 20 common names depending on the country where they are grown, but navigation and the retrieval of specific information is aided by a comprehensive index system.

This book is designed for health scientists, including nutritionists and dietitians, pharmacologists, public health scientists, those in agricultural departments and colleges, epidemiologists, health workers and practitioners, agriculturists, botanists, health care professionals of various disciplines, policy-makers, and marketing and economic strategists. It is designed for teachers and lecturers, undergraduates, and graduates.

The Editors

Acknowledgments

The work of Dr. Watson's editorial assistant, Bethany L. Stevens, in communicating with authors and editors and working on the manuscripts was critical to the successful completion of the book. It is very much appreciated. Support for Ms. Stevens' and Dr. Watson's editing was graciously provided by Dr. Preedy, Dr. Watson, and Southwest Scientific Editing & Consulting, LLC. Direction and guidance from Elsevier's staff was critical.

I

Overview and General Themes

Outline

Chapter 1. Rambutan (Nephelium lappaceum L.) Seed and Its Fat

Chapter 2. Soursop Seed: Soursop (Annona muricata L.) Seed, Therapeutic, and Possible Food Potential

Chapter 3. Red Horse-Chestnut Seeds of Aesculus × Carnea: A New Way for Health and Food Design?

Chapter 4. The African Breadfruit (Treculia africana) Decne Plant Seed: A Potential Source of Essential Food and Medicinal Phytoconstituents

Chapter 5. Perennial Horse Gram (Macrotyloma axillare) Seeds: Biotechnology Applications of Its Peptide and Protein Content – Bowman–Birk Inhibitors and Lectin

Chapter 6. Biological Properties of a Partially Purified Component of Neem Oil: An Updated and Revised Work

Chapter 7. Bioactive Compounds of Oregano Seeds

Chapter 8. Mango Seed: Mango (Mangifera indica L.) Seed and Its Fats

Chapter 1

Rambutan (Nephelium lappaceum L.) Seed and Its Fat

Julio A. Solís-Fuentes ¹ , Frixia Galán-Méndez ² , María del Rosario Hernández-Medel ¹ , and María del Carmen Durán-de-Bazúa ³       ¹ Instituto de Ciencias Básicas, Universidad Veracruzana, Avenida Luis Castelazo Ayala s/n, Xalapa, Veracruz, Mexico      ² Facultad de Ciencias Químicas, Universidad Veracruzana, Circuito Aguirre Beltrán s/n, Xalapa, Veracruz, Mexico      ³ Chemical Engineering Department, Labs 301-303, Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Ciudad de México, Mexico

Abstract

The rambutan (Nephelium lappaceum L.) is a plant of Asiatic origin whose fruits are widely appreciated and consumed in many parts of the world. The rambutan seed, an abundant and available residue and incipiently consumed as food by populations of some producing regions, is being re-evaluated in its composition and in its edible, nutritional, and medicinal qualities, as well as an unconventional source of edible vegetable fats. The fat of the rambutan seed, with a high content of oleic and arachidic acids, has physicochemical and phase properties close to those of some partially hydrogenated fats with high contents of trans fatty acids, so the possibility of being used in many of its applications toward obtaining healthier fats and zero trans foods is highly valued.

Keywords

Healthier fats; Nephelium lappaceum; Rambutan seed; Rambutan seed fat; Trans fats

List of abbreviation

ALP    Arachidoyl-linoleoyl-palmitoyl-glycerol

AOO    Arachidoyl-dioleoyl-glycerol

AOP    Arachidoyl-oleoyl-palmitoyl-glycerol

ASO    Arachidoyl-stearoyl-oleoyl-glycerol

ASP    Arachidoyl-stearoyl- palmitoyl-glycerol

CB    Cocoa butter

CBE    Cocoa butter equivalent

CE    Catechin equivalent

FA    Fatty acid

FFAs    Free fatty acids

FOs    Fat and oils

GAE    Gallic acid equivalent

RS    Rambutan seed

RSF    Rambutan seed fat

SFC    Solid fat content

SOS    1,3-distearoyl-2-oleoyl- glycerol

TGs    Triacylglycerols

WHO    World Health Organization

Introduction

Rambutan (Nephelium lappaceum L.) is an exotic plant from Southeast Asian native to the Malaysian–Indonesian region, closely related to fruit species as lychee (Litchi chinensis Sonn.) with whom it shares some morphological features except its long, thick, and soft spines or hairs in its shell; its edible pulp is white, juicy, translucent, subacid-sweet flavored, also similar to litchi. Like other parts of the plant, the seed of rambutan (RS) fruit contains important bioactive components; some researchers have shown that RS extracts can possess hypoglycemic, antinociceptive, analgesic, anti-inflammatory, CNS depressant, antibacterial, and anticancer activity. ¹ RS has some nutrients and also contains considerable amounts of edible fat with potential uses in the food and pharmaceutical industries, which is important because, currently, a clear trend has been observed toward the use of natural vegetable fats for a total or partial replacement of industrial trans fats obtained by hydrogenation or interesterification of vegetable oils, and, therefore, rambutan seed fat (RSF) properties have become a very important issue for the procurement of nutrition and health of the population.

Botanical Descriptions

Rambutan is a perennial tropical tree belonging to the Sapindaceae family, which includes around 37 genera and 72 species. It is a medium size evergreen tree that grows to a height of 12–20   m. The trees can be male, female, or hermaphroditic, with alternate and pinnate leaves (10–30   cm long and 3–11 leaflets) with small apetalous and discoidal flowers (from 2 to 5   cm). Its name is associated with the Malay word rambut, which means hairy. Its fruit, in clusters of 15–20 units, sometimes called hairy lychee is usually consumed fresh; ² , ³ it has a single seed, round or ellipsoid in shape; its color varies from pink to deep red or from orange red to yellowish red. There is a translucent and juicy white pulp under the fruit skin whose taste is sweet and pleasant. ⁴

The flowering and fruit production occur between 3 and 5 years after planting. More than 200 varieties of rambutan are cultivated and available throughout tropical Asia. ³ , ⁵

Historical Cultivation and Usage

It is believed that this plant is native to the Malay Archipelago, from where it spread to Thailand, Burma, Sri Lanka, India, Vietnam, the Philippines, and Indonesia. Later, at the beginning of the 20th century, some varieties of rambutan were introduced in the Western Hemisphere due to their high development potential in regions with favorable agro-climatic conditions for their cultivation: between 100 and 1000   m of altitude, temperatures of around 28°C, and blooming during spring and summer.

The most extensive cultivation of N. lappaceum is found in the countries of Southeast Asia, especially in Malaysia, the Philippines, and Thailand. The main use of rambutan has been as fresh fruit considering only its pulp as edible, but canned rambutan is also produced and exported by the main producer countries. ³ , ⁵

Present-Day Cultivation and Usage

The most important species, from the economic point of view, within the Nephelium genus is the rambutan. ³ It is cultivated in Southeast Asia and in Australia, South Africa, and Mexico, and in other tropical places in the world such as Hawaii, the Caribbean islands, Costa Rica, Honduras, and Panama, among many other places. In Thailand, the best known and popular varieties are Rongrien and Chompu, which have crispy arils and are suitable for both fresh and canned consumptions. Data about world cultivated area and production of rambutan are scarce, and estimates for the year 2003 show that its cultivation is on more than 200,000 hectares with a production of between 1.5 and 2 million tons each year. However, considering the tendency in many countries for a greater consumption of healthy fruits, it is feasible that to date such figures are widely exceeded. ² Thailand, Indonesia, and Malaysia are the main producers and exporters of the fruit accounting about 80% of the world production. ⁶ From the fruit, only the pulp is considered edible, generally consumed fresh, although sometimes it is processed industrially to obtain juices, jams, and jellies, among other products, generally in canned presentations. ⁴ , ⁷

The rambutan fruit is 34–54% pulp, 37–62% of peel, non-edible until now, and 4–9% of seed, consumed as food in some places and possibly suitable for some applications in foods. ⁸ , ⁹

The two main residues of rambutan fruit processing are the peel and seeds. Even though in some Asian countries, RS is eaten after roasting or boiling, having a slight bitter taste, according to popular knowledge, it is known that raw is poisonous. ⁷ RS as a waste in canned manufactures reaches thousands of tons by year in the main producer countries. Only in Thailand it is estimated that the rambutan canning industry produces around 2000 tons of RS each year. ¹⁰

Chemical composition of RS depends on varietal and phenotypic variability; ranges of some reported values are shown in Table 1.1: moisture 3.31–34.4%, fat 28.2–39.13%, crude protein 7.9–13.7%, with a good quality because of its essential amino acids present around 23.6–27.8%, ash 2.26–2.30%, crude fiber 7.6, and total carbohydrates 28.7–62.4%. Contents of the minerals – K, P, Mg, Mn, Fe, Na, and Zn – have also been reported. Some bioactive compounds are present too: phenolic acid in levels of 4.4–26.7   mg/100g of db seed, with an important presence of tannins, ellagic and gallic acids, geraniin, and corilagin. Thus, RS as a possible food contains important nutrients, as well as other constituents that have recognized bioactivity. Because of its protein and carbohydrate contents, some authors such as Harahap et al. ¹¹ have considered that RS is comparable to watermelon seeds (Citrullus lanatus Schrad) or pumpkin seeds (Cucurbita pepo).

Applications in Health Promotion and Disease Prevention

RS composition shows important nutritional constituents, with well-known effects in the maintenance of health, if its possibility as food is considered. However, some compounds with an antinutritive and toxic effect have also been identified as being present in RS, so their food safety must be fully evaluated. The bioactive compounds with a known antioxidant capacity, present in RS, represent an interesting aspect, since extracts of the seed have shown to possess hypoglycemic, antinociceptive, analgesic, anti-inflammatory, CNS depressant, antibacterial, and anticancer activity. ¹ , ¹² , ¹³

Table 1.1

a  Augustin MA, Chua BC. Composition of rambutan seeds. Pertanika 1988; 11(2):211–215.

b  Mehdizadeh S, Lasekan O, Muhammad K et al. Variability in the fermentation index, polyphenols, and amino acids of seeds of rambutan (Nephelium lappaceum L.) during fermentation. Journal of Food Composition and Analysis 2015; 37:128–135.

On the other hand, it is well known that the importance of vegetable fat and oils (FOs) in diet and food processing on human health and RS, being a highly available waste, can be used as an unconventional source of natural fats with possible uses in the food industry and as a vehicle for active medicines in the pharmaceutical industries, and in cosmetics.

Currently, the identification of new sources of natural dietary fats is an important asset because of their relative scarcity compared to those of vegetable oils and because the demand for edible fats for food applications has been satisfied, in most cases so far, through the partially hydrogenated fats production with high trans fatty acid (FA). The negative effect on health of diets with high levels of trans FA, corroborated in several investigations, ¹⁴ has been the basis for the approach of one of the global objectives of the World Health Organization to be achieved in the coming years, regarding the elimination of trans fats in processed food products ¹⁴ , ¹⁵ for being replaced with vegetable oils or with natural fats in agreement with the new approaches reassessing the role of saturated AF on health and on various diseases. ¹⁶

Nephelium lappaceum Seed Fat (RSF) Characteristics, Potential Food, and Therapeutic Uses

RSF Physical and Chemical Properties

Table 1.2 shows some physicochemical properties. The RSF is an almost white, semi-solid fat at room temperature, with 31Y+1.1R color on the Lovibond scale, and a fusion range between 14.5 and 55.8°C. Oleic and arachidic acids are the major FAs; RSF has a saponification and an iodine numbers of 157.0–246.7 and 37.6–50.6, respectively.

Chemical composition of RSF shows variability; Table 1.3 presents the ranges of data reported for many authors. The major FAs of RSF are oleic (33.35–46.64%), arachidic (26.03–34.36%), gondoic (5.75–10.55), and stearic acids (5.22–8.97), followed by palmitic and linoleic and in smaller amounts behenic, lignoceric, linoleic, lauric, and myristic acids. Globally, 37.51–46.24% are SFA and 44.19–62.50% are UFA.

Triglycerides of RSF correspond to 83.94–95.33%; so far, there are few reports that establish with certainty which are the majority. Harahap et al. ¹¹ found that these corresponded to AOO, ASO, AOP, ASP, and ALP with 49.8, 15.0, 12.8, 9.0, and 6.3%, respectively. Other triacylglycerols (TGs) identified by several authors around 3% or less are ALnO, arachidoyl linolenoyl oleoylglycerol; SOO, stearoyl dioleoyl glycerol; OOO, trioleoyl glycerol; and POS, palmitoyl oleoyl stearoyl glycerol, among others. ⁴

In the fraction of unsaponifiable (0.43–0.82%) campesterol, stigmasterol, β-sitosterol, and α-tocopherol have been identified.

Additionally, Harahap et al. ¹¹ found some metals content in the fat: Ca, Mg, and Zn (at concentrations of 160, 51, and 40   μg/g, respectively) among others.

Table 1.2

a  Lourith N, Kanlayavattanakul M, Mongkonpaibool K et al. Rambutan seed as a new promising unconventional source of specialty fat for cosmetics. Industrial Crops and Products 2016; 83:149–154.

RSF Phase Behavior

RFS has been proposed for being used as zero trans natural margarines and frying shortenings or in the formulation of pharmacological and cosmetic products, and to be used as special high-quality fats, such as those used in confectionery products ⁴ , ⁵ , ⁸ , ¹⁰ , specifically, the latter, as a possible substitute for cocoa butter (CB). ⁹ All these possible applications of RSF derive from the composition and properties including their phase properties.

It is known that vegetable FOs are a mixture of different TGs according to the different FAs that constitute them and that, together with the polymorphism, characteristic of these molecules determines their behavior as solid–liquid phase, ¹⁷ and in fact, unlike pure compounds, these mixtures of TGs do not have a single melting or crystallization temperature, but rather a temperature range in which the transition between the solid and liquid phases develops and completes. The transition temperature for the different TGs depends on the position of each FA in the TG molecule, its length, and the existence or not of insaturations in the chain of each FA. In general, saturated and longer hydrocarbon chains determine S–L transitions at higher temperatures. Thus, the composition in TGs and FAs of RSF explains that this is a semi-solid fat at an ambient temperature around 20°C.

Table 1.3

a  Winayanuwattikun P, Kaewpiboon C, Piriyakananon K et al. Potential plant oil feedstock for lipase-catalyzed biodiesel production in Thailand. Biomass Bioenergy 2008;32(12):1279–1286.

Table 1.2 presents the main physicochemical and phase properties of RSF. The solid fat content at several temperatures shows that around 20°C 25% of TGs of RSF are solid. Fig. 1.1 shows the typical fusion curve of RSF in which the temperatures at which the fat begins to melt (onset, −14.7°C) and to which it ends, to be totally liquid (off set, 55.8), can be observed; likewise, its groups of TGs can be identified with lower (<8°C), intermediate (from 8.1 to 29°C), and higher melting temperatures (>29°C), which allow us to perceive the possibility of separating them through fractionation, for example, dry fractionation method. This option will render more specific application alternatives to RSF. ⁵ It is evident that the S–L phase behavior of RSF depends not only on the composition of TGs but also on the variety of N. lappaceum; Chai et al. ¹⁸ made a comparison of these phase behaviors for 11 Thai varieties, with which the versatility and potential uses of RSF have considerably broadened.

RSF and Its Potential Food Uses for Health Promotion

The possibility of using RSF in food is wide due to the numerous applications of vegetable fats in this sector. Nowadays, the most obvious advantages that its alimentary use would bring in the procurement of health is in its contribution to the objective of gradually replacing trans fats in food applications, delineated by different organisms and health institutions at local and international levels.

Some of the possible uses of RSF or its fractions, which were studied and reported, are as shortenings and as an additional fat to CB or supplementary CB in confectionary products.

Sirisompong et al. ⁸ suggested that the RSF obtained from a Thai variety of rambutan showed chemical and physical characteristics comparable to those of conventional partially hydrogenated edible fats. The use of RSF to replace this type of fats is especially interesting when the oxidation of the product can become an important aspect.

Figure 1.1 Typical fusion curve of rambutan seed fat. The figure shows the temperatures at which the process of solid–liquid phase transition of rambutan seed fat occurs.

Mahisanut et al. ¹⁰ studied the isothermal fractionation of RSF with acetone and with ethanol, obtaining a fraction high in arachidic acid with acetone at 25°C and 24   h of incubation and whose properties were comparable to those of some commercial fully hydrogenated fats.

Sonwai and Ponprachanuvut ¹⁹ evaluated the physicochemical properties, the composition in FAs, and the phase behavior of RSF of varieties grown in Thailand, and their possible industrial applications. They say that the behavior of crystallization or melting turned out to be similar to that presented by CB, with a two-step crystallization curve, and that properties of the RSF may be appropriate in specific applications in various segments of the industry.

Febrianto et al. ²⁰ evaluated RSF in the development of confectionery products with improved characteristics through a treatment of fermentation and roasting of RS, analyzing the development of flavor compounds similar to cocoa due to the effect of these processes. The results showed that the desired pyrazine compounds were present and that they were up to 42.69% of the total odorant compound in the RSF. The fat from the fermented and roasted RS had similar characteristics with CB increasing its potential to be used as a substitute for CB.

In other non-food applications, Uraiwan and Satirapipathkul ²¹ and Witayaudom and Klinkesorn ²² reported the feasible use of RSF in the preparation of nanostructured lipid carriers for the delivery of bioactive compounds in cosmeceutical and pharmaceutical products.

Adverse Effects and Reactions, Allergies, and Toxicity

The scientific data about RS and RSF safety are scarce. Regarding the seed, it is known that some Asian peoples in rambutan producing regions, as the Philippines, consume it after its roasting. ⁷ The RS has a characteristic bitter taste and has been reported to have some narcotic effects that have been attributed to its contents of tannins, alkaloids, and saponins. ¹⁸ Fila et al. ²³ reported the content of some compounds with antinutritional effects in the different parts of rambutan; in the seed, saponins (2.10) and alkaloids (1.95   mg/100   g   db) were the most relevant ones, although phytates (0.77), oxalates (0.19), and tannins (0.28), as well as flavonoids (1.63), were also present. The authors concluded that these antinutritional compounds were in RS at tolerable levels.

Chai et al. ⁶ evaluated the RS toxicity, as a cocoa-like powder, after the fruit fermentation, drying, and roasted processes of the seed. Their results about brine shrimp lethality tests showed that SR, under these conditions, is not toxic.

Eiamwat et al. ²⁴ conducted tests to evaluate the toxicity of RSF in oral and dermal intakes in rats and rabbits, finding that a single oral dose of up to 5   and 2   g/kg of body mass in the dermal route was not lethal for rats. The treatment also did not cause skin irritation or signs of toxicity in rabbits. The authors concluded that RSF is a non-toxic fat.

Summary Point

• Rambutan is a fruit of Asian origin with a high consumption and industrialization in some regions of the world.

• RS is a residue of high availability, whose composition is attractive from the point of view of food, nutrition, and medicine.

• RS is a potential source of edible fat whose main FAs are oleic and arachidic acids.

• The physicochemical and phase characteristics of RSF make it potentially useable as a substitute for partially hydrogenated fats with high trans FA contents.

• Healthy dietary fats, free of trans FA, are of great importance in the promotion and maintenance of people's health.

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Chapter 2

Soursop Seed

Soursop (Annona muricata L.) Seed, Therapeutic, and Possible Food Potential

Julio A. Solís-Fuentes ¹ , María del Rosario Hernández-Medel ¹ , and María del Carmen Durán-de-Bazúa ²       ¹ Instituto de Ciencias Básicas, Universidad Veracruzana, Avenida Luis Castelazo Ayala s/n, Xalapa, Veracruz, Mexico      ² Chemical Engineering Department, Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Ciudad de México, Mexico

Abstract

Several genera of the Annonaceae family are characterized by containing bioactive components and are widely used in traditional medicine. Annona muricata L., a plant native to South America and widely cultivated in the tropical regions of the world, is the only one of this genus whose fruit, appreciated and consumed fresh, is also processed industrially. The seeds (AMS), traditionally inedible, are a residue of high availability whose composition has been the subject of extensive research. This paper describes that some of the components identified in seed fruit are of therapeutic importance in various diseases and health disorders, as well as their potential in the food industry, as AMS contain other components in significant quantities, particularly its oil, whose characteristics may be promising for possible applications, but which, at this time, despite some research efforts, the processes that guarantee its safety are not yet completely conclusive to rule out any toxicological risk.

Keywords

Annonaceous acetogenins; Annona muricata; Soursop metabolites; Soursop seed; Soursop seed oil

List of Abbreviations

AACGs    Annonaceous acetogenins

AMS    Annona muricata seeds

ATP    Adenosine triphosphate

ED50    Drug dose effective for 50% of exposed population

FA    Fatty acid

Hep 2,2,15    Human hepatoma cells infected with hepatitis B virus

Hep G2    Human hepatoma cells

IC50    Drug concentration required for 50% inhibition in vitro

THF    Tetrahydrofuran

THP    Tetrahydropyran

Introduction

Soursop (Annona muricata L) is a plant native to South America that is widely distributed in tropical and subtropical regions of the world; it belongs to the Annonaceae family and its fruits are widely appreciated for their organoleptic characteristics. The family includes several genera characterized by the presence of metabolites with important biological activities. AMS make up approximately 5% of ripe fruit weight. In recent years, scientific studies have confirmed the presence of alkaloids, acetogenins, and cyclopeptides, which are compounds of great importance that have attracted pharmacological interest. AMS also have a significant amount of oil whose composition and physical and chemical properties make it potentially attractive in the food sector.

Botanical Descriptions

A. muricata is an annonacea belonging to the Magnoliales Order and the Magnoliopsida Class. It is a tree from 4 to 7   m high, with smooth bark. Its leaves are long and pale green and its flowers have yellow-green fleshy petals. Its fruits are large, oval or heart shaped, with small green thin-shelled spines; their size ranges from 10 to 30   cm long and 15   cm wide, and they can weigh up to 2.5   kg. They have white flesh that is creamy and juicy. The seeds are small and numerous, dark-colored, and of compact consistency. They have a rigid coating that contains a kernel-like almond. At present, there is no information on the number of world varieties. Coarsely, soursop types were classified into sweet, subacid, or sour; however, in just one region of Puerto Rico, 14 varieties have been distinguished, and it is believed that in the other producing regions of the world there are many more. ¹

Historical Cultivation and Usage

Cultivated in Mexico already before the Spaniards arrived, the soursop has been highly appreciated for its edible fruit. It was distributed very early in the warm lowlands of eastern and western Africa, southeastern Asia, and China, where it was and continues to be commonly grown on a small scale or as a backyard tree. ² It was first used as fresh fruit and later in various food products processed either by hand or on an industrial scale. Historical information on the medicinal use of AMS is scarce, for it was not until the 20th century when its acaricidal property was first reported.

Present-day Cultivation and Usage

The soursop lives in tropical regions with warm weather ranging from sea level to 500   m high. In Mexico, for example, it is cultivated from the state of Sinaloa to the state of Chiapas and from the state of Veracruz to the Yucatan Peninsula along the Gulf of Mexico in small extensions up to 20   ha. In many other parts of the world, it is still grown as backyard trees. There are no data available for world production, imports, and exports. In Surinam, this fruit yields 43   kg/tree and 278 trees/ha. The commercial plantations are limited to the Philippines, the Caribbean, and South America.

At this time, it is used mainly as fresh and industrialized fruit. The leaves are used commercially for therapeutic uses. Extracts from the seed powder are presently used as an effective insecticide against lice, worms, and aphids, as well as a larvicide. ¹ , ³

Applications in Health Promotion and Disease Prevention

Annona muricata L. Seed and Its Therapeutic Potential

In traditional medicine it is known that the bark, root, leaf, fruit, and seed of the fruit of Annona muricata are used for various medical purposes in the tropics. The crushed seeds are used mainly against internal and external parasites, worms, and lice. ¹ , ³ The studies have been carried out in general with crude extracts of organic solvents such as ethanol and n-hexane, and some of them have allowed to identify their bioactivities as well as to evaluate the synergism of their compounds. For example, ethanolic extracts of AMS have demonstrated their power of inhibition on the growth of larvae of Spodoptera litura (Noctuidae), ⁴  Aedes aegypti, ⁵a–⁵d and Culex quinquefasciatus, a vector of filariasis a set of infectious diseases that affect the lymphatic system and the skin, of great epidemiological importance in low-income countries. ⁵d,⁵e

Komansilan et al. ⁵c showed that the n-hexane fraction was the most effective and toxic against the mosquito Aedes aegypti, with a LC50 of 73.77   ppm. The extract analyzed by GC-MS showed the relative abundance of methyl palmitate (39.93%), methyl oleate (25.05%), and methyl stearate (25.71%). Ranisaharivony et al. ⁵d reported the synergistic activity of AACGs annonacin, murisolin, and annonacinone from AMS extracts and the catalytic hydrogenation of annonacin, which resulted in a more effective mixture of diastereomers than annonacin alone, against the larvae of C. quinquefasciatus.

The synergism between the alcoholic extracts of AMS and Piper nigrum in larvicidal evaluations realized by Grzybowski et al. ⁵b resulted in an efficient, simple, and less toxic formula from AMS. In addition, the antimalarial (Plasmodium falciparum) and leishmanicidal activities of the AMS extracts have been evaluated by Boyom et al. ⁵f and Vila-Nova et al., ⁵g,⁵h respectively.

In other tests conducted by Rizki et al. ⁵i the ethanolic extract of AMS showed an hypoglycemic effect, finding that with a dose of 400   mg/kg the blood glucose levels were significantly decreased in the test subjects.

On the other hand, the extracts of AMS have also been evaluated in their effectiveness for the control of pests, which indirectly also affect human health, such is the case of the studies that corroborated the effect against Sitophilus zeamais, which often infest the stored rice, ⁵j and in the cases of cabbage moth Plutella xylostella, ⁵k and the aphid Brevicoryne brassicae, which affects crops of Brassica oleracea. ⁵l

The Annonaceae family is characterized, in general, as presenting an exclusive group of secondary metabolites of the family of AACGs, compounds which are also found in large numbers in the AMS. ⁶–8a,8b

The AACGs are an important group of long-chain FA derivatives, C-30 to C-37, usually with a terminal γ-lactone, saturated or unsaturated. Sometimes the FAs are one to three rings of THF or THP, adjacent or not, which are occasionally replaced with epoxide rings or double bonds near the middle of the aliphatic chain. Accordingly, there can be 7 different types of terminal γ-lactones (L-A to L-F), 10 skeletons with THF and/or THP (T-A to T-H, with 3 subtypes of T-G) and mono-, di-, or triepoxides. ⁶-⁸a,⁸b  Fig. 2.1 shows the general structure of an AACG. The THF ring system can be simple (one ring), adjacent (two rings), or not adjacent, with hydroxyl groups on both sides or not; this creates chiral centers in the molecules, making it very complex to elucidate the structures. Many AACGs isolated as pure compounds are actually a mixture of diastereomers. However, the synthesis of some AACGs makes it possible to assign the chemical configurations of the corresponding natural AACGs unequivocally. ⁸a–⁸c

Figure 2.1 General structure of an AACG. The AACGs are an important group of long-chain FA derivatives, C-30, C-32, or C-34, usually with a terminal γ-lactone, saturated or unsaturated.

A little more than 400 compounds have been reported in the literature since the discovery of uvaricin in 1982 all from various genera exclusive to the Annonaceae family, ⁷ although only some types of structures are present in the AACGs isolated from the AMS. ³ To date, the AACGs that have been isolated from the seeds of soursop include a terminal γ-lactone and THF in their structure; a few have epoxides, yet there are none with adjacent THP or THF.⁸a , ⁸b

More recently, annoreticuin-9-one, ⁸d murisolin, cis-annoreticulin, and sabadelin, as well as a mixture of β-sitosterol and stigmasterol in a ratio of 1:3, were isolated from AMS. ⁸e

Various pharmacological investigations have shown that these metabolites possess antitumoral, antidiarrheal, larvicidal, antimalarial, pesticidal, and fungicidal activities, especially with regard to their antitumoral properties in vitro. Some are among the most potent inhibitors of complex I (NADH: ubiquinone oxidoreductase) in the system of mitochondrial electron transport between said complex and the NADH-oxidase in the plasma membrane characteristic of cancer cells; these actions induce apoptosis (programmed cell death), perhaps following the deprivation of ATP. The decrease in ATP is especially toxic to multidrug resistant tumor cells as well as to pesticide-resistant insects that possess ATP-dependent systems of xenobiotic flows, so said metabolites can be regarded as extraordinary antitumor agents and pesticides, especially for inhibiting resistance mechanisms requiring an ATP-dependent flow. ⁹a

The AACGs may be among the most potent cytotoxic agents known, for example, trilobacin and asiminocin, AACGs isolated from Asimina triloba, have demonstrated values of DE50   <   10 −¹²   μg/mL in several human tumor cell lines. ⁹a A little over 40 AACGs showing cytotoxic activity have been isolated from the AMS, among which cis-annonacin may be mentioned as displaying a selective cytotoxicity toward colon adenocarcinoma cells (HT-29), 10,000 times more potent than that of adriamycin (IC50   =   1.0   ×   10 −⁸   μg/mL, IC50   =   5.1   ×   10 −⁴   μg/mL, respectively); cis-annonacin-10-one showed the same range as adriamycin toward the same type of cell line (IC50   =   9.0   ×   10 −⁴   μg/mL). ⁶ The acetogenin annoreticuin-9-one exhibited cytotoxic activity against human pancreatic tumor PACA-2 cell lines, human prostate adenocarcinoma PC-3, and lung carcinoma A-549. ⁸d In addition, the anticancer and antitumor activity of AMS AACGs has been shown in cases of oral KB cancer, gallbladder tumor, and toxicity against human hepatoma cells. ⁹b

A recent study on the phytoestrogenic, hypocholesterolemic, and antioxidant activities demonstrated by the ethanolic extract of AMS suggests the possible utility of AMS to counteract or eliminate cancerous tumors given the close relationship between the levels of estrogen, cholesterol, and, of course, free radicals, with the incidence of cancer. ⁹c

The bioactivity possessed by these compounds has made it possible to obtain a patent for the isolation, identification, and antitumoral use of AACGs from the AMS, those include muricin A, B, C, D, E, F, and G, among which the most effective were muricin D (IC50   =   6.6   ×   10 −⁴   μg/mL for Hep G2 and IC50   =   4.8   ×   10 −² for Hep 2,2,15); muricin F (IC50   =   4.28   ×   10 −²   μg/mL Hep G2 and IC50   =   3.86   ×   10 −³   μg/mL for Hep 2,2,15); and longifolicin (IC50   =   4.04   ×   10 −⁴   μg/mL for Hep G2 and IC50   =   4.9   ×   10 −³   μg/mL for Hep 2,2,15). However, both muricin A and muricin B showed selective activity toward Hep 2,2,15 cell line with IC50   =   5.13   ×   10 −³   μg/mL and IC50   =   4.29   ×   10 −³   μg/mL, respectively. ¹⁰  Table 2.1 shows some of the AACGs isolated from the AMS with cytotoxic activity conform to the structure shown in Fig. 2.2; Table 2.2 presents some of the patented AACGs showing substituents according to Fig. 2.3, and Fig. 2.4 shows