Chemistry of Spices This page intentionally left blank Chemistry of Spices Edited by Villupanoor A. Parthasarathy Indian Institute of Spices Research Calicut, Kerala, India Bhageerathy Chempakam Indian Institute of Spices Research Calicut, Kerala, India and T. John Zachariah Indian Institute of Spices Research Calicut, Kerala, India CABI is a trading name of CAB International CABI Head Offi ce CABI North American Offi ce Nosworthy Way 875 Massachusetts Avenue Wallingford 7th Floor Oxfordshire OX10 8DE Cambridge, MA 02139 UK USA Tel: +44 (0)1491 832111 Tel: +1 617 395 4056 Fax: +44 (0)1491 833508 Fax: +1 617 354 6875 E-mail: cabi@cabi.org E-mail: cabi-nao@cabi.org Website: www.cabi.org ©CAB International 2008. All rights reserved. No part of this publication may be reproduced in any form or by any means, electronically, mechanically, by photocopying, recording or otherwise, without the prior permission of the copyright owners. A catalogue record for this book is available from the British Library, London, UK. Library of Congress Cataloging-in-Publication Data Chemistry of spices / [edited by] V.A. Parthasarathy, B. Chempakam, T. John Zachariah. p. cm. Includes bibliographical references and index. ISBN 978-1-84593-405-7 (alk. paper) 1. Spices Analysis. 2. Spice plants Composition. I. Parthasarathy, V.A. II. Chempakam, B., Dr. III. Zachariah, T. John. IV. Title. SB305.C44 2008 641.3'383 dc22 2007043551 ISBN-13: 978 1 84593 405 7 Typeset by Spi, Pondicherry, India. Printed and bound in the UK by Biddles Ltd, King’s Lynn. Contributors vii Preface ix 1 Introduction 1 V.A. Parthasarathy, B. Chempakam and T. John Zachariah 2 Black Pepper 21 T. John Zachariah and V.A. Parthasarathy 3 Small Cardamom 41 B. Chempakam and S. Sindhu 4 Large Cardamom 59 B. Chempakam and S. Sindhu 5 Ginger 70 T. John Zachariah 6 Turmeric 97 B. Chempakam and V.A. Parthasarathy 7 Cinnamon and Cassia 124 N.K. Leela 8 Clove 146 N.K. Leela and V.P. Sapna 9 Nutmeg and Mace 165 N.K. Leela 10 Coriander 190 V.A. Parthasarathy and T. John Zachariah 11 Cumin 211 Shamina Azeez 12 Fennel 227 Shamina Azeez Contents v 13 Fenugreek 242 N.K. Leela and K.M. Shafeekh 14 Paprika and Chilli 260 T. John Zachariah and P. Gobinath 15 Vanilla 287 Shamina Azeez 16 Ajowan 312 T. John Zachariah 17 Star Anise 319 B. Chempakam and S. Balaji 18 Aniseed 331 N.K. Leela and T.M. Vipin 19 Garcinia 342 K.S. Krishnamurthy and V.P. Sapna 20 Tamarind 362 K.S. Krishnamurthy, V.P. Sapna and V.A. Parthasarathy 21 Parsley 376 Shamina Azeez and V.A. Parthasarathy 22 Celery 401 K.S. Krishnamurthy 23 Curry Leaf 413 V.A. Parthasarathy, T. John Zachariah and B. Chempakam 24 Bay Leaf 426 V.A. Parthasarathy, T. John Zachariah and B. Chempakam Index 435 vi Contents Indian Institute of Spices Research, Calicut – 673 012, Kerala, India Phone: 0091 – 0495 – 2731410, Fax: 0091 – 0495 – 2730294 E-mail: mail@spices.res.in, Web site: www.spices.res.in Dr V.A. Parthasarathy, Director E-mail: parthasarathy@spices.res.in Division of Crop Production & PHT Dr B. Chempakam, Principal Scientist & Head E-mail: chembakam@spices.res.in Dr T. John Zachariah, Senior Scientist – Biochemistry E-mail: john@spices.res.in Dr N.K. Leela, Senior Scientist – Organic Chemistry E-mail: leela@spices.res.in Dr K.S. Krishnamurthy, Senior Scientist – Plant Physiology E-mail: kskrishnamoorthy@spices.res.in Dr Shamina Azeez, Senior Scientist – Biochemistry E-mail: shamina@spices.res.in Gobinath, P. E-mail: gobinath_bio@yahoo.com Balaji, S. E-mail: bio_balaji@yahoo.co.in Sapna, V.P. E-mail: sapnajeesh@yahoo.co.in Shafeekh, K.M. E-mail: shefi clt@yahoo.com Sindhu, S. E-mail: intelnidhu@yahoo.com Vipin, T.M. E-mail: vip_kkd@yahoo.co.in Contributors vii This page intentionally left blank Spices are woven into the history of nations. The desire to possess and monopolize the spice trade has, in the past, compelled many a navigator to find new routes to spice-producing nations. In the late 13th century, Marco Polo’s exploration of Asia established Venice as the most important trade port. Venice remained prosperous until about 1498. Portuguese explorer Vasco de Gama sailed around Africa’s Cape of Good Hope to reach Calicut, India. He returned with pepper, cinnamon, ginger and jewels, and also deals for the Portuguese to continue trade with India. Spices impart aroma, colour and taste to food preparations and sometimes mask unde- sirable odours. The volatile oils from spices give the aroma and the oleoresins impart the taste. There is a growing interest in the theoretical and practical aspects of the inner biosynthetic mechanisms of the active principles in spices, as well as in the relationship between the biological activity and the chemical structure of these secondary metabolites. The antioxidant properties of herbs and spices are of particular interest in view of the impact of oxidative modification of low-density lipoprotein cholesterol in the develop- ment of atherosclerosis. A range of bioactive compounds in herbs and spices has been studied for anticarcinogenic properties in animals, but the challenge lies in integrating this knowledge to ascertain whether these effects can be observed in humans, and within defined cuisines. Research on the structure activity relationships in spice components has become an exciting field since these compounds play a major role in the culinary, indus- trial and pharmacological fields. Hence, we have attempted to compile all available information on the chemistry of spice crops such as black pepper, cardamom (small), cardamom (large), ginger, turmeric, cinnamon and cassia, clove, nutmeg and mace, coriander, cumin, fennel, fenugreek, paprika, vanilla, ajowan, star anise, aniseed, garcinia, tamarind, parsley, celery, curry leaf and bay leaf. To edit this book, we have used the current Indian expertise on spices and we have made every effort to collate all available information so that the book will be useful to researchers, industrialists and postgraduate students of agriculture, horticulture and phy- tochemistry. It will also be a very useful resource book for spice traders and processors. We are grateful to CABI for giving us the opportunity to edit this book and we are indebted to Ms Sarah Hulbert of CABI Head Office for her immense help in getting the book into final shape. She has answered an array of e-mails and strings of questions to help us in this ven- ture and we thank her for her patience and assistance. Preface ix x Preface We appreciate the help rendered by Mr A. Sudhakaran, artist-cum-photographer of IISR, Calicut, Kerala, for designing the cover page. The help given by Ms T.V. Sandhya in typesetting the manuscript is gratefully acknowledged. We also thank the Director of the Indian Institute of Spices Research, Calicut, India, for providing photographs of the spices. V.A. Parthasarathy B. Chempakam T.J. Zachariah [...]... shows the area and production of important spices in the world Compared with many other field and horticultural crops, area and production of spices is limited The FAO database gives the area and production of a limited number of spices only Spices were cultivated in an area of 7587.02 thousand ha, with a production of 31,859.69 thousand t during 2005 The world export of spices during 2005 was 3592.48... and Sakariah, K.K (2002) Chemistry and biochemistry of (-) -hydroxycitric acid from garcinia Journal of Agricultural and Food Chemistry 50, 10–22 Jung, E.M., Lim, J.H., Lee, T.J., Park, J., Choi, K.S and Kwon, T.K (2005) Curcumin sensitizes tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis through reactive oxygen speciesmediated up-regulation of death receptor 5 (DR5)... component of fenugreek seeds (Mazza et al., 2002) Among the leafy spices, 45 aroma volatiles of desert parsley have been identified, with the major constituents as myristicin, apiole, b-phellandrene, p-mentha-1,3,8triene and 4-isopropenyl-1-methylbenzene (MacLeod et al., 1985) Among these, apiole in particular has a desirable parsley odour character The leaf stems of celery show three main constituents of. .. 1,3,8-p-Menthatriene, b-phellandrene, myristicin CH3 CH3 H 3C OMe O CH2 H3C O CH2 β-Phellandrene 1,3,8-p -menthatriene CH2 Myristicin Celery (Apium graveolens L.) Myrcene, limonene, a-pinene CH3 CH2 CH3 CH2 H 3C CH2 H3C CH3 α-Pinene -( −) Limonene Myrcene Bay leaf (Laurus nobilis L.) 1,8-Cineole, linalool, a-terpinyl acetate, methyl eugenol OCH3 CH3 CH3 CH3 OCH3 OH O CH2 CH3 O H 3C CH3 1,8-Cineole H3C CH3... turpentinelike off-odours (Lewis et al., 1969) The major compounds in fresh pepper are translinalool oxide and α-terpineol, whereas dry black pepper oil contains - and β-pinenes, d-limonene and β-caryophyllene as major components In cardamom, the oil has very little mono- or sesquiterpenic hydrocarbons and is dominated by oxygenated compounds, all of which are potential aroma compounds While many of the identified... the latest trade in spices at 400,000–450,000 t, valued at US$1.5–2.5 billion annually Black pepper accounts for about 35% of the world trade in spices Table 2.1 gives an approximate estimate of world production and export of black pepper (Ravindran, 2000) ©CAB International 2008 Chemistry of Spices (eds V.A Parthasarathy, B Chempakam and T.J Zachariah) 21 22 T.J Zachariah and V.A Parthasarathy Table... initially to the presence of piperine only, the structure of which is trans,trans- 5-( 3,4-methylenedi-oxyphenyl)2,4-pentadienoic acid piperidide Further investigations into the pungency of this spice by several workers led to the discovery that materials other than piperine also contributed to its pungency (Traxler, 1971) Chun et al (2002) found that 88% of the polysaccharide of black pepper berries was... 3C CH3 O α-Terpinyl acetate CH2 Methyl eugenol Continued 16 V.A Parthasarathy et al Table 1.6 Continued Spice crop (botanical name) Compound and structure Curry leaf (Murraya koenigii Spreng.) Murrayacine, koenigine, a-pinene, b-phellandrene CHO OMe N H HO Me N H OCH3 O CH3 CH3 Murrayacine Koenigine C(CH3)2 CH3 CH3 α-Pinene β-Phellandrene Table 1.7 Value-added products from major spices Spices Product... ancient civilizations, where spices found applications in food preservation, cooking and traditional medicine Asia still grows most of the spices that once ruled the trade, including cinnamon, pepper, nutmeg, clove and ginger However, more and more spices are being planted in ©CAB International 2008 Chemistry of Spices (eds V.A Parthasarathy, B Chempakam and T.J Zachariah) 1 2 V.A Parthasarathy et al the... 8-cineole is the major component, together with α-terpinyl acetate, sabinene, α-pinene, β-pinene, β-elemene, α-terpineol, linalool and eugenol (Kilic et al., 2004) The major chemical constituents in spices are tabulated in Table 1.6 1.4 Value Addition and New Product Development Farm-level processing operations are the most important unit operations for value addition and product diversification of . properties of herbs and spices are of particular interest in view of the impact of oxidative modification of low-density lipoprotein cholesterol in the develop- ment of atherosclerosis. A range of bioactive. Chemistry of Spices This page intentionally left blank Chemistry of Spices Edited by Villupanoor A. Parthasarathy Indian Institute of Spices Research Calicut, Kerala,. Head E-mail: chembakam @spices. res.in Dr T. John Zachariah, Senior Scientist – Biochemistry E-mail: john @spices. res.in Dr N.K. Leela, Senior Scientist – Organic Chemistry E-mail: leela @spices. res.in Dr