The Piscicidal Plants in Southeast Asia and Their Active Constituents
KAZUYOSHI KAWAZU
Department of Food Science and Technology, Kyoto University
There are many kinds of plants which have carcinosarcoma etc. by two groups of scientists been employed for hundred of years as a medi in the U.S.A.ll Among effective plant species cine, insecticide, insect repellent, antiseptic, are Stephania hernandiifolia, Elephantopus elatus, arrow poison or fish poison. A number of Acnistus arborscens, Catharanthus roseus and such useful plants has been noted among thous Acronychia baueri, from which ( ± )-tetrandrine, ands of higher plants growing in Southeast elephantopin and elephantin, withaferin A, vin Asia. For example, Stro/Jhantus gratus, Rau caleukoblastine, and acronychin were isolated wolfia serjJentina, Digitalis JJUrpurea and Cinchona as the active constituents, respectively. succirnbra were known as medicinal plants; Regarding plant species employed as pestici Derris species were used as a fish poison and des, it is considerably easy to isolate and insecticide; A lbizzia procera was said to repel elucidate the active constituents of the plants ants ; and Melia azadirachta was noted as keep because the bioassay method is readily set up. ing away insects. A typical classical investigation on such a Extensive chemical investigations to reveal natural pesticide was that on rotenone isolated the active principles of these useful plants were from Derris species. Subsequently a lot of carried out. From medicinal plants a variety plants was examined for insecticidal property of cardiac glycosides and various alkaloids and some of them were found to have the pro were isolated and their structures were esta perty to some extent. Among these effective blished. species, are M ammea americana, Quassia amara The isolation of active principles from medi and Tripterygium wilfordii, from which mam cinal plants is sometimes not easy since an ap meins, quassin and ryanodine were isolated as propriate bioassay to search the active principles the active constituents, respectively. More re is not available because of the complex remedial cently, M elia azedarach that repels insects was effects of the medicinal plants. The chemical chemically studied, and meliantriol was isolated investigation on medicinal plants can, therefore, and characterized as the active constituent. find out some chemical constituents of the It should be emphasized that all the plants plants, but hardly reveal the active principles. cited above are also known as fish poisons. It It is necessary to set up an appropriate is interesting and important to investigate bioassay for examining the specified biological chemical constituents of the piscicidal plants in activity in order to isolate the active principle view of finding out novel compounds having from the plant. If the bioassay method is any biological activity. In Southeast Asia about standardized, it is scarecely impossible to isolate 100 species of plants are reported to have been the active principles even though they are con used as fish poisons2>. Some of these plants, tained in very small quantities. together with organs employed are listed in Recently more than 10,000 plant extracts were Table I. screened for antitumor activity against the Leu A few of them were investigated chemically, kemia L-12120 in mice and the Walker 256 and the active constituents were isolated, the 20 Table 1, Piscicidal Plants in Southeast Asia Araceae Acorus calamtts L., root Stemonaceae Stemona burkillii Prain, tuberous root Urticaceae FicttS diversifolia Blume, latex Polygonaceae Polygonum barbatum L., whole plant P. orientale L., whole plant M enisPermaceae CissamPelos pareira L., root Stephania hernandiifolia Walp., root Anamirta paniculata Coleb. (=A. cocculus Wight et Arm.) seeds CafJparidaceae Gynandropsis gy11andra Briquet, seeds Pittosporaceae Pittosporum ferrngineum Ait., leaves and fruits Leguminosae Albizzia acle Merr., bark A. procera Benth., bark Derris elliptica Benth., root D. malacce11sis Prain, root Milletia sericea Benth., root Pachyrrhizus erosus Urban, leaves and seeds P. tuberostu Spreng., seeds Pithecellobium ellipticum Hassk., bark Tephrosia candida DC., root, bark and leaves Tephrosia vogelii Hook, whole plant T. purpurea Pers., whole plant Whit/ordiodendron Pubescens Burk ill, seeds Litiaceae Erythroxylon cuneatum Kurz, bark and leaves Rutaceae Acronychia resinosa Forst., bark A. laurifolia Blume, root Buxaceae Buxm rolfei Vidal, fruits EttPhorbiaceae Cleistanthus collinus Benth., bark, root and leaves Euphorbia antiquorium L ., latex E. neriifolia L., leaves E. tirucalli L., latex E. trigona Haw., latex Jatropha curcus L., latex Mallottu apelta Muell.·Arg., seeds M. philippinensis Muell.-Arg., seeds Guttiferae Calophyllm inoPhyllum L., bark, leaves and seeds C. muscigerum Boeri. et '.Koord., bark C. soulattri Burm., bark and roots Thymelaeaceae Wickstroemia ridleyi Gamble, bark Lecythidiaceae Barringtonia acutangula Gaertn., bark and seeds Myrsinaceae Aegiceras corniculatum Blanco ( =A. majiu Gaertn.) ba1·k Ebenaceae Diospyros ebenaster Retz., immature fruits D. lucida Wall., fruits D. wallichii Ki~g et Gamble, root, leaves and fruits Styracaceae ' . Styrax be11zoin Dryander, bark and root V erbenaceae Callicarpa candicans (Burm. f.) Hoch1·., (=C. cana L.) leaves C. maingayi King et Gamble, . leaves Vitex trifolia L., bark, fruits and leaves
- 21- structures of which were established. The fangchinoline, ( + )-tetrand1'ine ( V), isochondro others remain uninvestigated or partially in dendrine have been isolated as active consti vestigated, the active constituents of which have tuentssi. It is noteworthy that ( ± )-tetrandrine not yet been established. has been found to exhibit antitumor activity. Herewith we wish to summarize the piscicidal plants whose active constituents have been established, and to show the structures3l. c1~o'fl()_c,1, 1) Stenwna burkillii Prain (Stemonaceae) is q::o--~ TN a tuberous herb found in Southeast Asia. Its tuberous root is a fish poison and was used as an insecticide. From the root of S. tuberosa, ,J"&.i; tuberostemoni.ne (I ) was isolated and the struc OCH , ture established.
( IV ) ( V)
4) Anamirta f1aniculata Coleb. (Menis/Jer maceae) is a small woody climber found throughout Southeast Asia. Its seeds were used as a fish poison. The piscicidal principles are
( I ) picrotoxinin (VI) and picrotin (VIl)G>. 2) Cissamf1clos fJareira L. ( M enisfJermaceac) ,,.o, , is a small woody climber distributed through oc---+-'- -'~, out the tropics. The pounded root is used I as a fish poison. The active principles are 0 similar to those of tubocurare in the Amazon (Chondrodendron tomentosum Ruiz et Pavon). ···01-1 They are alkaloids of biscoclaurine type, be beerine (II), ( ± )-curine, hayatinine, isochon drodendrine, sepeerine, cissampareine (III) and 4"-O-methylcurine4 J. ( VJ ) ( VU ) Cll, Ow N- Clb HO H 5) Albizzia fJrocera Benth. ( Legurninosae) is a woody climber found in India, Burma, Thai land and Java. The bark was used as a fish poison. The action was confirmed due to a ¢~ saponin which consists of a triterpene acid as 116a.CH, OH 0 an aglycone and arabinose, rhamnose and glu CH,-N cose as a sugar moiety. OCl b 6) De1'1'is ellifJtica Benth. and Derris malac censis Prain ( Leguminosae) are woody climbers ( II J ( Ill ) found throughout Southeast Asia. The roots 3) Stephania hemandiifolia (Willd.) Walp. are old famous fish poisons and also insecticides. (Menispermaceae) is a climber found from India Besides rotenone (VIII) (10% of the dried to Australia. The tuberous root is extremely root), deguelin (IX), toxicarol ( X), elliptone poisonous and was used as a fish poison. It (XI ) and tephrosin are contained as active was said that the active principles were picro constituents?>. Rotenone has long been used toxin and the related compounds, but several as one of the three important natural insectici alkaloids, isotrilobine (IV), ( ± )-tetrandrine, des.
- 22 - ~oy"~
~OCII, c~~o OCII, OCH , ~n (111) OCII, cu, _ (IX ) R = H (X) 11 = 011 o,;° ()yoy ~OCH, OCH, Justicia hayatai var. decumbens Yamamoto. 10) Calof1hyllum inophyllum L . (Gutti/erae) ( Xl ) is a big tree distributed throughout Southeast Asia. It was used as a medicine in India. 7) Milletia sericea Benth. (Leguminosae) is The seeds, bark and leaves were employed as a large woody climber found throughout Malay fish poisons. From the seeds calophyllolide sia. The root is used as a fish poison. The (XVI), ( ± )-inophyllolide (XVII) and calophyl active principle seems to be rotenone since the lic acid (XVII) were isolated by Pro£. Polo Formosan M. taiwaniana Hayata was fotmd to nskyS> . Calophyllolide was reported to have contain rotenone. anticoagulant activity. As the piscicidal con stituents of the leaves we isolated ( )-inophyl 8) Pachyrrhizus erosus Urban (Legttminosae) + lolide and the four related compounds (XIX)9>. is a herbaceous climber, native of tropical America. It's leaves and seeds were used as fish poisons. Rotenone, pachynhizone (XII), pachyrrhizin (XIII) and erosnin (XIV) were isolated from the seeds. 0 0 ( XVI ) ( X'III ) (XI) (XIV ) 9) Cleistanthus collinus Benth. (Euf>hor biaceae) is a tree common in the more open forests of the tropics. The bark and root are recorded to be used as criminal poisoning, and -24 -