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Antiparasitic compounds from East African plants: Isolation and biological activity of anonaine, matricarianol, canthin-6-one and caryophyllene oxide

Published online by Cambridge University Press:  19 September 2011

F. Bettarini ,
G. E. Borgonovi ,
T. Fiorani ,
I. Gagliardi ,
V. Caprioli ,
P. Massardo ,
J. I. J. Ogoche ,
A. Hassanali ,
E. Nyandat  and
A. Chapya
F. Bettarini
Affiliation:
Istituto Guido Donegani S.p.A., Enimont Group, Via G. Fauser 4, 28100 Novara, Italy
G. E. Borgonovi
Affiliation:
Istituto Guido Donegani S.p.A., Enimont Group, Via G. Fauser 4, 28100 Novara, Italy
T. Fiorani
Affiliation:
Istituto Guido Donegani S.p.A., Enimont Group, Via G. Fauser 4, 28100 Novara, Italy
I. Gagliardi
Affiliation:
Istituto Guido Donegani S.p.A., Enimont Group, Via G. Fauser 4, 28100 Novara, Italy
V. Caprioli
Affiliation:
Agrimont S.r.l., Ricerca Fitofarmaci, Enimont Group, Via G. Fauser 4, 28100 Novara, Italy
P. Massardo
Affiliation:
Agrimont S.r.l., Ricerca Fitofarmaci, Enimont Group, Via G. Fauser 4, 28100 Novara, Italy
J. I. J. Ogoche
Affiliation:
The International Centre of Insect Physiology and Ecology, P. O. Box 30772, Nairobi, Kenya
A. Hassanali
Affiliation:
The International Centre of Insect Physiology and Ecology, P. O. Box 30772, Nairobi, Kenya
E. Nyandat
Affiliation:
The International Centre of Insect Physiology and Ecology, P. O. Box 30772, Nairobi, Kenya
A. Chapya
Affiliation:
The International Centre of Insect Physiology and Ecology, P. O. Box 30772, Nairobi, Kenya
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Abstract

Five natural compounds possessing antiparasitic activity were isolated from East African plants and tested, together with some semisynthetic derivatives, against micro-organisms and arthropods of agricultural interest. Anonaine (1), from Annona squamosa, canthin-6-one(8) and 5-methoxycanthin-6-one (9), from Fagaropsis angolensis, showed fungicidal activity. E,Z-matricarianol (4), from Hoehnelia vernonioides was fungicidal, Insecticidal and acarlcldal. Caryophyllene oxide (12), isolated from Uvaria sp., turned out to be insecticidal and antifeedant. Canthin-6-one (8) and its dihydroderivative 11 were the most effective antimicrobial compounds tested. The possibility ofusing some of the isolated compounds as leads for new synthetic chemicals is discussed.

Résumé

Cinq produits naturels ayant de l'activité antiparasitaire étaient isolés de plantes de1' Afrique Orientale et evalué, avec quelques dérivés semisynthétiques, contre des microrganismes et des arthropodes d'intérêt agricole. L'anonaine (1), isolée de 1'Annona squamosa, le cantin-6-one (8) et le 5-methoxycantin-6-one (9), isolés de la Fagaropsis angolensis, montraient de l'activité fongicide. L' E, Z-matricarianol (4), isolé de l'Hoehnelia vernonioides, se revelait fongicide, insectcide et acarcide. L'époxidede B-caryophylléne (12), isolé de 1' Uvaria sp., se réélalt insectcide et antiappetant Le cantin-6-one (8) et son dihldroderivé 11 étaient les plus actifs parmi les produits antimcrobiens évalues. On discute la possibilité d'utiliser quelques-uns des produits isolés commesouches de nouveaux produits synthétiques.

Keywords

Antiparasitic activityfungicidal activityinsecticidal activityanonaineAnnona squamosacanthin-6-oneFagaropsis angolensisZanthoxylum usambarensisE,Z-matricarianolHoehnelia vernonioidescaryophyllene oxideUvaria sp.
Type
Research Articles
Information
International Journal of Tropical Insect Science , Volume 14 , Issue 1 , February 1993 , pp. 93 - 99
Copyright
Copyright © ICIPE 1993

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References

REFERENCES

Achenbach, H., Renner, C. and Addae-Mensah, I. (1982) Untersuchung der Inhaltsstoffe von Hexalobus crispiflorus. Liebigs Ann. Chem., 1623–1633.CrossRefGoogle Scholar
Anderson, L. A., Harris, A. and Phillipson, J. D. (1983) Production of cytotoxic canthin-6-one alkaloids by Ailanthus altissima plant cell cultures. J. Nat. Prod. 46, 374–378.CrossRefGoogle ScholarPubMed
Bhakuni, D. S., Tewari, S. and Dhar, M. M. (1972) Aporphine alkaloids of Annona squamosa. Phytochemistry 11, 1819–1822.Google Scholar
Bohlmann, F., Zdero, C., Bethke, H. and Schumann, D. (1968) Elektronens to Binduzierte Fragmentierung von Acetylenverbindungen, II. Chem. Ber. 101, 1553–1570.Google Scholar
Carpita, A., Neri, D. and Rossi, R. (1987) Stereocontrolled synthesis of naturally-occurring polyacetylenes characterized by (E)-1-en-3-yne, (E)-1-en-3,5-diyne, (1E,5E)-1,5-dien-3-yne, and (1E,7E)-1,7-dien-3,5-diyne moieties. Gazz. Chim. Ital. 117, 481–489.Google Scholar
Crespi-Perellino, N., Guicciardi, A., Malyszko, G. and Minghetti, A. (1986) Biosynthetic relationship between indole alkaloids produced by cell cultures of Ailanthus altissima. J. Nat. Prod. 49, 814–822.Google Scholar
Fournier, G., Lenicque, P. M. and Paris, M. R. (1978) Etude de la toxicité de l'huile essentielle de Cannabis sativa L. et de ses principaux constituants sur la planaire (Dugesia tigrina G). Toxicol. Eur. Res. 1, 3857–389.Google Scholar
Groweiss, A. and Kashman, Y. (1983) Eight new xenia diterpenoids from three soft corals ofthe red sea. Tetrahedron 39, 3385–3396.CrossRefGoogle Scholar
Harris, A., Anderson, L. A., Phillipson, J. D. and Brown, R.T. (1985) Canthin-6-onealkaloids from Brucea antidysenterica root bark. Planta Medica 42, 151–153.CrossRefGoogle Scholar
Hubert, T. D. and Wiemer, D. F. (1985) Anti-repellent terpenoids from Melampodium divaricatum. Phytochemistry 24, 1197–1198.CrossRefGoogle Scholar
Koike, K. and Ohmoto, T. (1985) Carbon-13 nuclear magnetic resonance study of Canthin-6-one alkaloids. Chem. Pharm. Bull. 33, 5239–5244.Google Scholar
Leboeuf, M., Cavé, A., Forgacs, P., Tibcrghien, R., Provost, J., Touché, A. et Jacquemin, H. (1982) Alcaloides des Annonacees XL: Etude chimique et pharmacologique des alcaloides de l'Annona montana Macf. Plant. Med. Phytother. XVI, 3, 169–184.Google Scholar
Liou, Y. F., Lin, K. H. and Lou, S. T. (1979) Screening for antimicrobial and anti-tumour alkaloids. J. Taiwan Pharm. Assoc. 31, 28–39.Google Scholar
Mitscher, L. A., Showalter, H. D. H., Shipchandler, M. T., Leu, R. P. and Beal, J. L. (1972) Antimicrobial agents from higher plants. IV. Zanthoxylum elephantiasis. Isolationand identification of Canthin-6-one. Lloydia 35, 177–180.Google Scholar
Odebiyi, o. o. and Sofowora, E. A. (1979) Antimicrobial alkaloids from a Nigerian chewing stick (Fagara zanthoxyloides). Planta Medica 36, 204–207.CrossRefGoogle ScholarPubMed
Oehl, R., Lenzer, G. and Rosenmund, P. (1976) Eine neue Darstellung von Canthin-6-one sowie Synthesen einiger Indolo[2,3-a]chinolizine. Chem. Ber. 109, 705–709.CrossRefGoogle Scholar
Ohmoto, T. and Sung, Y. I. (1982) Antimycotic substances in the crude drugs II. Shoyak. Zasshi 36, 307–314.Google Scholar
Rao, K. V. and Davis, T. L. (1982) Constituents of Magnolia grandiflora. III. Toxicprinciple of the wood. J. Nat. Prod. 45, 283–287.Google Scholar
Rosenkranz, H. J. and Schmid, H. (1968) Notiz uber die Synthese von Iso-, Noriso- und Desathyltuboflavin. Helv. Chim. Acta 51, 565–568.Google Scholar
Stipanovic, R. D., Williams, H. J. and Smith, L. A. (1986) Cotton terpenoid inhibition of Heliothis virescens development. ACSSymp. Ser. 296, 79–94.Google Scholar
Villar, A., Mares, M., Rios, J. L., Canton, E. and Gobernado, M. (1987) Antimicrobial activity of benzylisoquinoline alkaloids. Pharmazie 42, 248–250.Google Scholar
Vohora, S. B., Kumar, I. and Naqvi, S. A. H. (1975) Phytochemical, pharmacological, antibacterial and anti-ovulatory studies on Annona squamosa. Planta Medica 28, 97–100.Google Scholar