RSS-Feed abonnieren
DOI: 10.1055/s-2002-36350
© Georg Thieme Verlag Stuttgart · New York
Antimalarial Agents from Plants. III. Trichothecenes from Ficus fistulosa and Rhaphidophora decursiva
Publikationsverlauf
Received: April 25, 2002
Accepted: July 28, 2002
Publikationsdatum:
20. Dezember 2002 (online)
![](https://www.thieme-connect.de/media/plantamedica/200212/lookinside/thumbnails/10.1055-s-2002-36350-1.jpg)
Abstract
Bioassay-directed fractionation of an extract prepared from the dried leaves and stem barks of Ficus fistulosa Reinw. ex Blume (Moraceae) led to the isolation of verrucarin L acetate (1), together with 3α-hydroxyisohop-22(29)-en-24-oic acid, 3β-gluco-sitosterol, 3,4-dihydro-6,7-dimethoxyisocarbostyril, 3,4,5-trimethoxybenzyl alcohol, α-methyl-3,4,5-trimethoxybenzyl alcohol, indole-3-carboxaldehyde, palmanine, and aurantiamide acetate. Roridin E (2) was identified in a subfraction from the dried leaves and stems of Rhaphidophora decursiva Schott (Araceae). Verrucarin L acetate and roridin E were characterized as macrocyclic trichothecene sesquiterpenoids and found to inhibit the growth of Plasmodium falciparum with IC50 values below 1 ng/ml.
Key words
Ficus fistulosa - Moraceae - Rhaphidophora decursiva - Araceae - antimalarial activity - bioassay-directed fractionation - trichothecene sesquiterpenoids - verrucarin L acetate - roridin E
References
- 1 Rosenthal J P, Beck D, Bhat A, Biswas J, Brady L, Bridbord K. et al . Combining high risk science with ambitious social and economic goals. Pharmaceutical Biology. 1999; 37 (Supplement) 6-21
- 2 Soejarto D D, Gyllenhaal C, Regalado J C, Pezzuto J M, Fong H HS, Tan G T. et al . Studies on biodiversity of Vietnam and Laos: the UIC-based ICBG program. Pharmaceutical Biology. 1999; 37 (Supplement) 100-13
- 3 Tuyen NV; Kim D SHL, Fong H HS, Soejarto D D, Khanh T C, Tri M V. et al . Structure elucidation of two triterpenoids from Ficus fistulosa . Phytochemistry. 1998; 50 467-9
- 4 Zhang H J, Tamez P A, Hoang V D, Tan G T, Hung N V, Xuan L T. et al . Antimalarial compounds from Rhaphidophora decursiva . Journal of Natural Products. 2001; 64 772-7
- 5 Zhang H J, Qiu S X, Tamez P A, Tan G T, Aydogmus Z, Hung N V. et al .Antimalarial agents from plants. II. Decursivine, a new antimalarial indole alkaloid from Rhaphidophora decursiva. Pharmaceutical Biology 2002 40: in press
- 6 Kitajima J, Kimizuka K, Arai M, Tanaka Y. Constituents of Ficus pumila leaves. Chemical Pharmaceutical Bulletin. 1998; 46 1647-9
- 7 Faizi S, Ali M, Saleem R I, Bibi S. Complete 1H- and 13C-NMR assignments of stigma-5-en-3-O-β-glucoside and its acetyl derivative. Magnetic Resonance Chemistry. 2001; 39 399-405
- 8 Jarvis B B, Midiwo J O, DeSilva T, Mazzola E P. Verrucarin L, a new macrocyclic trichothecene. Journal of Antibiotics. 1981; 34 120-1
- 9 Patra A, Mukhopadhyay P K. Carbon-13 NMR spectra of some benzene derivatives. Journal of Indian Chemical Society. 1983; 60 265-8
- 10 Koul S, Koul J L, Taneja S C, Dhar K L, Jamwal D S, Singh K ,. et al . Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities. Biorganic and Medicinal Chemistry. 2000; 8 251-68
- 11 Kametani T, Ohsawa T, Ihara M, Fukumoto K. Studies on the syntheses of heterocyclic compounds. DCCLV. Iminoketene cycloaddition. (4). Alternative syntheses of 5,6,7,8-tetrahydro-2,3-dimethoxy-8-oxoisoquinolo[1,2-b]quinazoline and rutecarpine. Chemical Pharmaceutical Bulletin. 1978; 26 922-6
- 12 Valencia E, Weiss I, Firdous S, Freyer A J, Shamma M. The isoindolobenzazepine alkaloids. Tetrahedron. 1984; 40 3957-62
- 13 Sammes M P, Katritzky A R, Law K W. 13C-NMR chemical shift assignments for some 1H-pyrrole-2-carboxylic acid derivatives. Magnetic Resonance Chemistry. 1986; 24 827-33
- 14 Wahidulla S, D’Souza L, Kamat S Y. Dipeptides from the red alga Acanthophora spicifera. Phytochemistry. 1991; 30 3323-5
- 15 Saikawa Y, Okamoto H, Inui T, Makabe M, Okuno T, Suda T. et al . Toxic principles of a poisonous mushroom Podostroma cornu-damae . Tetrahedron. 2001; 57 8277-81
- 16 Isaka M, Punya J, Lertwerawat Y, Tanticharoen M, Thebtaranonth Y. Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria . Journal of Natural Products. 1999; 62 329-31
- 17 Tamm C, Breitenstein W. The biosynthesis of trichothecene mycotoxins: Study of Secondary Metabolism. Editor(s): Steyn PS Academic Press New York; 1980: 69-104
- 18 Jarvis B B, Midiwo J O, Bean G A, Aboul-Nasr M B, Barros C S. The mystery of trichothecene antibiotics in Baccharis species. Journal of Natural Products. 1988; 51 736-44
- 19 Ueno Y, Hosoya M, Morita Y, Ueno I, Takashi T. Inhibition of the protein synthesis in rabbit reticulocyte by nivalenol, a toxic principle isolated from Fusarium nivale-growing rice. Journal of Biochemistry. 1968; 64 479-85
- 20 Cundliffe E, Davies J E. Inhibition of initiation, elongation, and termination of eukaryotic protein synthesis by trichothecene fungal toxins. Antimicrobial Agents and Chemotherapy. 1977; 11 491-9
- 21 Hernandez F, Cannon M. Inhibition of protein synthesis in Saccharomyces cerevisiae by the 12,13-epoxytrichothecenes trichodermol, diacetoxyscirpenol and verrucarin A: Reversibility of the effects. Journal of Antibiotics. 1982; 35 875-81
Professor Harry H. S. Fong
Program for Collaborative Research in the Pharmaceutical Sciences, M/C 877
College of Pharmacy
University of Illinois at Chicago
833 S. Wood St.
Chicago, IL 60612
USA
eMail: hfong@uic.edu
Fax: +1-312-413-5894