New Cytotoxic Bis 5-Alkylresorcinol Derivatives from the Leaves of Oncostemon bojerianum from the Madagascar Rainforest

Bioassay-directed fractionation of a CH(2)Cl(2)-MeOH extract of the leaves of Oncostemon bojerianum resulted in the isolation of eight new 5-alkylresorcinols, named oncostemonols A-H (1-8), and two known derivatives, (8'Z)-1,3-dihydroxy-5-[16'-(3' ',5' '-dihydroxyphenyl...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2002-11, Vol.65 (11), p.1627-1632
Main Authors: CHATURVEDULA, V. S. Prakash, SCHILLING, Jennifer K., MILLER, James S., ANDRIANTSIFERANA, Rabodo, RASAMISON, Vincent E., KINGSTON, David G. I.
Format: Article
Language:English
Subjects:
Acetylation
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
Drug Screening Assays, Antitumor
Female
General pharmacology
Humans
Inhibitory Concentration 50
Madagascar
Medical sciences
Methylation
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Ovarian Neoplasms
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Primulaceae - chemistry
Resorcinols - chemistry
Resorcinols - isolation & purification
Resorcinols - pharmacology
Stereoisomerism
Tumor Cells, Cultured - drug effects
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Summary:Bioassay-directed fractionation of a CH(2)Cl(2)-MeOH extract of the leaves of Oncostemon bojerianum resulted in the isolation of eight new 5-alkylresorcinols, named oncostemonols A-H (1-8), and two known derivatives, (8'Z)-1,3-dihydroxy-5-[16'-(3' ',5' '-dihydroxyphenyl)-8'-hexadecen-1'-yl]benzene (9) and (8'Z)-1,3-dihydroxy-5-[14'-(3' ',5' '-dihydroxyphenyl)-8'-tetradecen-1'-yl]benzene (10). The structures of the new compounds 1-8 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. All the compounds exhibited cytotoxic activity against the A2780 ovarian cancer cell line.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0201568