W Tang G. Eisenbrand Chinese Drugs of Plant Origin Chemistry, Pharmacology, and Use in Traditional and Modem Medicine With 41 Figures Springer-Verlag Berlin Heidelberg New York London Paris Tokyo Hong Kong Barcelona Budapest Professor Dr. WEICI TANG Professor Dr. GERHARD EISENBRAND Lebensmittelchemie und Umwelttoxikologie, Universitiit Kaiserslautem, Erwin-SchrOdinger-StraBe, D-67S0 Kaiserslautem ISBN-13: 978-3-642-73741-1 e-ISBN-13: 978-3-642-73739-8 DOl: 10.1007/978-3-642-73739-8 This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustra tions, recitation, broadcasting, reproduction on microfilm or in any other way, and storage in data banks. 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In every individual case the user must check such information by consulting the relevant literature. 27/3145-543210 Printed on acid-free paper Preface Traditional Chinese medicine has been used for thousands of years by a large population. It is currently still serving many of the health needs of the Chinese people; and still enjoying their confi dence it is practised in China in parallel with modern Western medical treatment. In addition to scientific organisations dedi cated to modern Western medicine, e. g. the Chinese Academy of Medical Sciences and various medical schools, a series of parallel institutions have been established in China to promote traditional Chinese medicine, such as the Academy of Traditional Chinese Medicine and training institutions. Almost all hospitals in China have a department of traditional medicine. Furthermore, a large number of scientific journals are dedicated to traditional Chinese medicine, covering both experimental and clinical investigations. Medicinal materials constitute a key topic in the treatment of disease according to traditional Chinese medicine. The Chinese Pharmacopoeia (1985 edition) is therefore divided into two sepa rate volumes, Volume I containing traditional Chinese medicinal materials and preparations and Volume II containing pharmaceu tics of Western medicine. The oldest Chinese review of medicinal materials, Shennong Bencao Jing (100-200 A. D.), covered 365 herbal drugs. The clas sic compilation in this field, Bencao Gangmu (Compendium of Materia Medica), was published in 1578 by Li Shi-zhen and recorded as many as 1898 crude drugs of plant, animal and min eral origin. About 50 years ago modern chemical and pharmacological methods were first used to investigate traditional medicinal mate rials in China. With the growth in our knowledge about chemistry, biochemistry, physiology, and pharmaceutics and the progress made in scientific instrumentation, there have been an increasing number of scientific reports characterizing the biological activities of the chemical constituents of Chinese medicinal materials. The majority of these papers have been in Chinese, scattered in a series of journals not easily available outside China. The present book provides information on recent advances and perspectives for future research into Chinese medicinal materials, including a large number of reports from Chinese journals. It is hoped that this information may be of value for the development of new drugs and may stimulate further investigations. Since tradi- VI Preface tional Chinese medicine has its own theoretical system that is rather different from modern pharmacological science, we hope that this book may serve as a bridge between traditional Chinese medicine and modern Western medicine. Our descriptions focus on the chemical constituents and the most important biological activities. Toxicological aspects, espe cially those relating to mutagenic and carcinogenic activities, are also given consideration. Within this limited survey it was not possible to cover all the Chinese medicinal materials used in traditional and folk medicine. Altogether, more than 500 species and subspecies from about 130 genera and about 3000 chemical constituents have been described. Most subjects represent official drugs of plant origin selected from the Chinese Pharmacopoeia, Vol. I (1985). For completeness, the total list of official plant species in the Chinese Pharmacopoeia ~ (1985) and in the appendix to it have been included. On the other hand, some unofficial plants with biologically active ingredients have also been considered. Examples are Anisodus tanguticus with anticholinergic alkaloids and drugs of potential use in the treat ment of cancer, such as Camp to theca acuminata, Cephalotaxus spp., Rabdosia spp., and Tripterygium wilfordii. Different plant species within the same genus are generally treated as one item. Exceptions are the genera Artemisia, Panax, and Sophora. Some items from Chinese folk medicine have not been included in this edition because of limited space. Examples are Ganoderma lucidum, Gossypium herbaceum, Huperzia serrata, and Zanthoxy lum species. They might be included in a later edition. Most medicinal materials contain a large variety of known or still unknown compounds. Traditional Chinese medicine prefers modalities characterized by a combination of numerous individual materials, sometimes up to a hundred or more. It is obvious that the interaction between individual materials might be of consider able relevance for the biological effectiveness of these combina tions. Studies on the chemical constituents and pharmacological activities of combined preparations have been very scarce up (0 now and an appropriate discussion of the effects of such combina tions is therefore not possible at the present time. Kaiserslautern, January 1992 WTANG G. EISENBRAND Contents 1 Acanthopanax senticosus (Rupr. et Maxim.) Harms . 1 2 Achyranthes bidentata BI. 13 3 Aconitum spp. . . . . . .19 4 Acorus gramineus Soland. 45 5 Agrimonia pilosa Ledeb. . 47 6 Ailanthus altissima (Mill.) Swingle 51 7 Akebia quinata (Thunb.) Decne. . 59 8 Alangium chinense (Lour.) Harms 69 9 Albizia julibrissin Durazz. . . . 73 10 Alisma orientalis (Sam.) Juzep. . 75 11 Allium sativum L. 79 12 Alpinia spp. . . . . . . . . . 87 13 Amomum spp. . . . . . . . . 95 14 Andrographis paniculata (Burm. f.) Nees 97 15 Anemarrhena asphodeloides Bge. 105 16 Anemone raddeana Regel . . . . 109 17 Angelica spp. . . . . . . . . . 113 18 Anisodus tanguticus (Max.) Pasch. 127 19 Ardisiajaponica (Thunb.) BI. 135 20 Areca catechu L. . 139 21 Aristolochia spp. . . . . . . 145 22 Artemisia annua L. . . . . . 159 23 Artemisia argyi LevI. et Vant. 175 24 Artemisia capillaris Thunb. and A. scoparia Waldst. et Kit. . . . . . . . . . . . 179 25 Asarum spp. . . . . . . . . . . . . 185 26 Astragalus membranaceus (Fisch.) Bge. 191 27 Atractylodes macrocephala Koidz. 199 28 Blelilla striata (Thunb.) Reichb. f. 203 29 Brucea javanica (L.) Merr. . 207 30 Bupleurum spp. ........ 223 31 Caesalpinia sappan L. . . . . . . 233 32 Calvalia lilacina (Mont. et Berk.) Lloyd . 237 33 Camp to theca acuminata Decne. 239 34 Carpesium abrotanoides L. . 263 35 Carthamus tinctorius L. . . . . 267 36 Centella asiatica (L.) Urb. . . . 273 37 Centipeda minima (L.) A. Braun et Aschers. 277 38 Cephalotaxus spp. . . . . . . . . . . . 281 VIII Contents 3'9 Choerospondias axillaris (Roxb.) Burtt et Hill 307 40 Chrysanthemum indicum L. and C. morifolium Ramat.. . . . . 309 41 Cimicifuga dahurica (Turcz.) Maxim. 315 42 Cinnamomum cassia Presl . . . . . 319 43 Cissampelos pare ira L. var. hirsuta (Buch. ex DC.) Formen 331 44 Citrus spp. ....... . . . . 337 45 Clematis spp. . . . . . . . . . . 351 46 Codonopsis pilosula (Franch.) Nannf. 357 47 Coptis spp. . . . . . . . . . . . 361 48 Cordyceps sinensis (Berk.) Sacco . . 373 49 Corydalis turtschaninovii Bess. f. yanhusuo Y. H. Chou et C. C. Hsii. . 377 50 Crocus sativus L. . . . . . 395 51 Cucurbita moschata Duch. . 399 52 Curcuma spp. . . . . . . 401 53 Cynanchum glaucescens (Decne.) Hand.-Mazz. 417 54 Daphne genkwa Sieb. et Zucco 429 55 Datur(l metal L. . . . . 437 56 Daucus carota L. . . . . 447 57 Dendrobium nobile Lindl. 451 58 Dichroa febrifuga Lour. . 455 59 Dioscorea spp. . . . . . 459 60 Ecklonia kurome Okam. . 475 61 Eleutherine americana Merr. et Heyne 479 62 Ephedra spp. ..... 481 63 Epimedium spp. . . . . 491 64 Erycibe obtusifolia Benth. 499 65 Eucommia ulmoides Olivo 501 66 Evodia rutaecarpa (Juss.) Benth. 509 67 Forsythia suspensa (Thunb.) Vahl. 515 68 Fraxinus spp. . . . . . 521 69 Fritillaria spp. . . . . . 525 70 Gardenia jasminoides Ellis 539 71 Gastrodia elata Bl. 545 72 Gentiana spp. . 549 73 Ginkgo bi/oba L. . 555 74 Glycyrrhiza spp. . 567 75 Houttuynia cordata Thunb. 589 76 !lex pubescens Hook et Am. 593 - 77 Inula spp. . . . . . . . . 597 78 Leonurus heterophyllus Sweet 607 79 Ligusticum chuanxiong Hort. 609 80 Lithospermum erythrorhizon Sieb. et Zucco . 613 81 Lonicera japonica Thunb. . . . . . . . . 621 82 Luffa cylindrica (L.) Roem. . . . . . . . 627 83 Lycium barbarum L. and L. chinensis Mill. 633 Contents IX 84 Magnolia spp. . . . . . . . . . . . . . . . .. 639 85 Melia azedarach L. and M. toosendan Sieb. et Zucco 647 86 Menispermum dauricum DC.. . . 659 87 Momordica cochinchinensis (Lour.) Spreng. and M. grosvenori Swingle 665 88 Morus alba L. . . . . . 669 89 Nelumbo nucifera Gaertn. . 697 90 Paeonia spp.. . . . . . . 703 91 Panax ginseng C. A. Mey. . 711 92 Panaxjaponicus C. A. Mey. 739 93 Panax notoginseng (Burk.) F. H. Chen 745 94 Peucedanum praeruptorum Dunn . 753 95 Phellodendron amurense Rupr. . . . . 759 96 Physochlaina infundibularis Kuang . . ~~ 763 97 Phytolacca americana L. and P. acinosa Roxb. 765 98 Pinellia ternata (Thunb.) Breit. . 777 99 Polygala tenuifolia Willd. . . 781 100 Polygonum spp. . . . . . . 787 101 Pseudolarix kaempferi Gord. . 793 102 Pueraria lobata (Willd.) Ohwi 797 103 Qingdai. . . . . . 805 104 Quisqualis indica L.. . . . . 813 105 Rabdosia spp. . . . . . . . 817 106 Rehmannia glutinosa Libosch. 849 107 Rheum spp. . . . . . . . 855 108 Rhododendron dauricum L. 877 109 Rubia cordifolia L. . . . . 885 110 Salvia miltiorrhiza Bge. . . 891 111 Schisandra chinensis (Turcz.) BailI. 903 112 Scutellaria baicalensis Georgi 919 113 Sophoraflavescens Ait. 931 114 Sophora japonica L. .... 945 115 Stemona spp. . . . . . . . 957 116 Stephania tetrandra S. Moore 963 117 Swertia mileensis T. N. Ho et W L. Shih 979 118 Trichosanthes kirilowii Maxim. . . . 983 119 Tripterygium wilfordii Hook.. . . . 989 120 Uncaria rhynchophylla (Miq.) Jacks. 997 121 Verbena ofJicinalis L. . . . . . . . 1003 122 Vitex negundo L. var. cannabifolia (Sieb. et Zucc.) Hand.-Mazz. ............ 1007 123 Zingiber officinale (Willd.) Rosc. . . . . 1011 124 Ziziphusjujuba Mill. and Z. spinosa Hu . 1017 Appendix 1 . 1025 Appendix 2 . 1038 Subject Index 1039 j Acanthopanax senticosus (Rupr. et Maxim.) Harms - - = - - - - - - - 1.1 Introduction Ciwujia, Radix Acanthopanacis senticosi, is the dry root and rootstock of Acantho panax (Eleutherococcus) senticosus (Rupr. et Maxim.) Harms (Araliaceae), which is collected in spring and fall. It is listed officially in the Chinese Pharmacopoeia and commonly known as "Siberian ginseng". It belongs to the same plant family as Panax ginseng. In addition, two galenic preparations of A. senticosus are also in cluded in the Chinese Pharmacopoeia: - Ciwujia Jingao, Extractum Acanthopanacis senticosi, prepared by extraction of the powdered root of A. senticosus with 75% ethanol and concentration of the extract - Ciwujia Pian, Tabellae Acanthopanacis senticosi, prepared from the extract The roots and rootstock of A. senticosus and its preparations have been used as a tonic in Chinese traditional medicine for a long time. 1.2 Chemical Constituents From the roots and stems of A. senticosus collected in China, isofraxidin (1-1), sesamin (1-2), fJ-sitosterol (1-3), friedelin (1-4), and several polysaccharides have been isolated in addition to eleutherosides A, B (1-8), Bl (1-9), C, D, E, I, K, L, and M [1]. The eleutherosides I, K, L, and M have also been isolated from the leaves of A. senticosus [2]. Isofraxidin is a derivative of coumarin, the lactone of coumarinic acid; sesamin is a lignan derivative; and fJ-sitosterol, a widely distributed plant sterol, has a stig mastane (1-5) carbon skeleton, whereas friedelin belongs to triterpenes derived from D: A-friedooleanane (1-6). 0, ::-15 H--8° 0 rl()oMe o~-­ OAO~OH l)=l 0 OMe o Isofraxidin (1-1) Sesamin (1-2) 2 Acanthopanax senticosus (Rupr. et Maxim.) Harms Me o HO P-Sitosterol (1-3) Friedelin (1-4) Stigmastane (1-5) D:A-Friedooleanane (1-6) The eleutherosides are glycosides with different aglycones. Thus, eleutheroside A (1-7) is a steroid glycoside with f3-sitosterol as the aglycone; eutherosides I (1-13), K (1-14), L (1-15), and M (1-16) are triterpene glycosides with oleanolic acid as the aglycone; and eleutherosides D (1-11) and E (1-12) are epimeric syringaresinol diglycosides. The other eleutherosides are glycosides with simple aglycones. The most simple eleutheroside is eleutheroside C (1-10), which is ethyl a-D-galactopyra noside. Eleutheroside B is identical to syringin. Me MeO HO~CH200~CH=CH-CH20H ~I20~ y- OH HN HO MeO OH OH Eleutheroside A (1-7) Eleutheroside B (1-8)