Abstract
The bitter and related constituents have been isolated fromVernonia amygdalina (Compositae), a plant ingested by wild chimpanzees possibly suffering from parasite-related diseases in the Mahale Mountains National Park, Tanzania. Isolated from the plant were four known sesquiterpene lactones, seven new steroid glucosides, and two aglycones of the glucosides. The sesquiterpene lactones showed significant in vitro antischistosomal, plasmodicidal, and leishmanicidal activities. Antischistosomal activity was also found for the major steroid glucoside, vernonioside B1. A trend in the glucosides to show significant antischistosomal, plasmodicidal, and amebicidal activities when the sugar moiety was removed, was observed. Vernodalin, judged as the most significant constituent for antiparasitic activities in vitro, was tested for in vivo antischistosomal effect. It was, however, highly toxic to the cercaria-infected mouse. Chimpanzees have been only rarely observed to ingest anything but the pith of the young stem. The occurrence of vernonioside B1 and its aglycone vernoniol B1, the major constituents among the steroid-related constituents, were detected at significant levels in the pith. However, vernodalin was abundant only in the leaves and bark. Thus, chimpanzees at Mahale were hypothesized to control parasite-related diseases by ingesting the young pith of this tree containing steroid-related constituents.
References
Brack, M. 1987. Agents Transmissible from Simians to Man. Springer-Verlag, Berlin.
Delmas, F., Gasquet, P., Timon-David, P., Madadi, N., Vanelle, P., Vaille, A., andMaldonado, J. 1993. Synthesis and in vitro anti-protozoan activity of new 5-nitrothiophene oxime ether derivatives.Eur. J. Med. Chem. 28:23–27.
Huffman, M. A., andSeifu, M. 1989. Observations on the illness and consumption of a possibly medicinal plantVernonia amygdalina (Del.), by a wild chimpanzee in the Mahale Mountains National Park, Tanzania.Primates 30:51–63.
Huffman, M.A., andWrangham, R.W. 1993. Diversity of medicinal plant use by wild chimpanzees. Mahale Mountains Chimpanzee Research Project. Ecological Report No. 83, Kyoto University, Kyoto.
Huffman, M.A., Nishida, T., andUehara, S. 1990. Intestinal parasites and medicinal plant use in wild chimpanzees: Possible behavioral adaptation for the control of parasites. Mahale Mountains Chimpanzee Research Project. Ecological Report No. 72, Kyoto University, Kyoto.
Huffman, M.A., Koshimizu, K., Ohigashi, H., andKawanaka, M. 1992. Medicinal plant use by wild chimpanzees: A behavioral adaptation for parasite control? Abstracts of papers, the American Association for the Advancement of Science (AAAS) Meetings, Chicago, Illinois p. 12.
Huffman, M.A., Gotoh, S., Izutsu, D., Koshimizu, K., andSeifu, M. 1994. Further observations on the use of the medicinal plant,Vernonia amygdalina (Del.) by a wild chimpanzee, its possible effect on parasite load, and its phytochemistry.Afric. Stud. Monogr. In press.
Jisaka, M., Kawanaka, M., Sugiyama, K., Takegawa, K., Huffman, M.A., Ohigahsi, H., andKoshimizu, K. 1992a. Antischistosomal activities of sesquiterpene lactones and steroid glucosides fromVernonia amygdalina, possibly used by wild chimpanzees against parasite-related diseases.Biosci. Biotech. Biochem. 56:845–846.
Jisaka, M., Ohiigashi, H., Takagaki, T., Nozaki, H., Tada, T., Hirota, M., Irie, R., Huffman, M.A., Nishida, T., Kaji, M., andKoshimizu, K. 1992b. Bitter steroid glucosides, vernoniosides A1, A2, and A3, and related B1 from a possible medicinal plant,Vernonia amygdalina, used by wild chimpanzees.Tetrahedron 48:625–632.
Jisaka, M., Ohigashi, H., Takegawa, K., Huffman, M.A., andKoshimizu, K. 1993a. Antitumoral and antimicrobial activities of bitter sesquiterpene lactones ofVernonia amygdalina, a possible medicinal plant used by wild chimpanzees.Biosci. Biotech. Biochem. 57:833–834.
Jisaka, M., Ohigashi, H., Takegawa, K., Hirota, M., Irie, R., Huffman, M.A., andKoshimizu, K. 1993b. Steroid glucosides fromVernonia amygdalina, a possible chimpanzee medicinal plant.Phytochemistry 34:409–413.
Kawabata, M., andNishida, T. 1991. A preliminary note on the intestinal parasites of wild chimpanzees of the Mahale Mountains, Tanzania.Primates 32:275–278.
Kawanaka, M. 1983. Deposition and maturation ofSchistosoma japonicum eggs in vitro: Comparison between Japanese and Philippine strains (in Japanese with English summary).Jpn. J. Parasitol. 32:305–315.
Kupchan, S.M., Hemingway, R.J., Karim, A., andWerner, D. 1969. Tumor inhibitors. XLVII. Vernodalin and vernomygdin, two new cytotoxic sesquiterepene lactones fromVernonia amygdalina Del.J. Org. Chem. 34:3908–3911.
Nishida, T., andUehara, S. 1983. Natural diet of chimpanzees (Pan troglodytes schweinfurthii): Long term record from the Mahale Mountains, Tanzania.Afr. Stud. Monogr. 3:109–130.
Ohigashi, H., Jisaka, M., Takagaki, T., Koshimizu, K., Huffman, M.A., Nishida, T., Takasaki, H., andKaji, M. 1991a. Possible medicinal plants used by wild chimpanzees, and their physiologically active compounds (in Japanese).Africa Kenkyu (J. Afric. Stud.) 39:15–27.
Ohigashi, H., Jisaka, M., Takagaki, T., Nozaki, H., Tada, T. Huffman, M.A., Nishida, T., Kaji, M., andKoshimizu, K. 1991b. Bitter principle and a related steroid glucoside fromVernonia amygdalina, a possible medicinal plant for wild chimpanzees.Agric. Biol. Chem. 55:1201–1203.
Page, J.E., Balza, F., Nishida, T., andTowers, G.H.N. 1992. Biologically active diterpene fromAspilia mossambicensis, a chimpanzee medicinal plant.Phytochemistry 31:3437–3439.
Rodriguez, M., Aregullin, M., Nishida, T., Uehara, S., Wrangham, R., Abramowski, Z., Finlayson, A., andTowers, G.H.N. 1985. Thiarubrine A, a bioactive constituent ofAspilia (Asteraceae) consumed by wild chimpanzees.Experientia 41:419–420.
Watt, J.M., andBreyer-Brandwijik, M.G. 1962. The medicinal and poisonous plants of southern and western Africa. E. & S. Livingstone Ltd., Edinburgh, 1457 pp.
Wrangham, R.W., andNishida, T. 1983.Aspilia spp. leaves: A puzzle in the feeding behavior of wild chimpanzees.Primates 24: 276–282.
Wright, C.W., Bray, D.H., O'Neill, M.J., Warhurst, D.C., Phillipson, J.D., Quetin-Leclercq, J., andAngenot, L. 1991. Antiamoebic and antiplasmodial activities of alkaloids isolated fromStrychnos usambarensis.Planta Med. 57:337–340.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ohigashi, H., Huffman, M.A., Izutsu, D. et al. Toward the chemical ecology of medicinal plant use in chimpanzees: The case ofVernonia amygdalina, a plant used by wild chimpanzees possibly for parasite-related diseases. J Chem Ecol 20, 541–553 (1994). https://doi.org/10.1007/BF02059596
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02059596