Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone

Two new compounds, a cyclic peptide desmocyclopeptide ( 1) and a special flavone desmorostratone ( 2) were isolated from the stem bark of Desmos rostrata, along with two known compounds, desmosdumotins B ( 3) and C ( 4). Their structures were established on the basis of the spectral data, including...

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Bibliographic Details
Published in:Tetrahedron 2009-08, Vol.65 (34), p.7171-7176
Main Authors: Nguyen, Ngoc Tuan, Pham, Van Cuong, Litaudon, Marc, Guéritte, Françoise, Bodo, Bernard, Nguyen, Van Tuyen, Nguyen, Van Hung
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical Sciences
Chemistry
Exact sciences and technology
General pharmacology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Medical sciences
Organic chemistry
Peptides
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Preparations and properties
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Summary:Two new compounds, a cyclic peptide desmocyclopeptide ( 1) and a special flavone desmorostratone ( 2) were isolated from the stem bark of Desmos rostrata, along with two known compounds, desmosdumotins B ( 3) and C ( 4). Their structures were established on the basis of the spectral data, including mass spectrometry and 2D NMR. The total synthesis of desmorostratone ( 2) was performed in order to confirm its structure as well as that of desmosdumotin C ( 4), which was a tautomeric mixture in the solution. Finally, cytotoxity of these compounds were evaluated. Desmosdumotin C ( 4) displayed a moderate inhibition activity against KB cell line with an IC 50 of 19.2 μM, whereas the other products showed a weak inhibition against the same cell line target. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.06.017