New Chemical Constituents of Euphorbia quinquecostata and Absolute Configuration Assignment by a Convenient Mosher Ester Procedure Carried Out in NMR Tubes

Two new compounds, an ent-isopimarane-type diterpene, 3alpha,12alpha-dihydroxy-ent-8(14),15-isopimaradien-18-al (1), and a dihydrobenzo[b]furan neolignan, (-)-trans-9-acetyl-4,9'-di-O-methyl-3'-de-O-methyldehydrodiconiferyl alcohol (2), along with five known compounds, 7,7'-dihydroxy-...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2002-09, Vol.65 (9), p.1278-1282
Main Authors: SU, Bao-Ning, PARK, Eun Jung, MBWAMBO, Zakaria H., SANTARSIERO, Bernard D., MESECAR, Andrew D., FONG, Harry H. S., PEZZUTO, John M., KINGHORN, A. Douglas
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Carcinoma, Hepatocellular
Cell Transformation, Neoplastic - chemically induced
Crystallography, X-Ray
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Epidermis
Euphorbia - chemistry
Furans - chemistry
Furans - isolation & purification
Furans - pharmacology
General pharmacology
Inhibitory Concentration 50
Lignans - chemistry
Lignans - isolation & purification
Lignans - pharmacology
Medical sciences
Mice
Molecular Structure
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Stems - chemistry
Plants, Medicinal - chemistry
Quinone Reductases - metabolism
Stereoisomerism
Tanzania
Tumor Cells, Cultured - drug effects
Wood
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Summary:Two new compounds, an ent-isopimarane-type diterpene, 3alpha,12alpha-dihydroxy-ent-8(14),15-isopimaradien-18-al (1), and a dihydrobenzo[b]furan neolignan, (-)-trans-9-acetyl-4,9'-di-O-methyl-3'-de-O-methyldehydrodiconiferyl alcohol (2), along with five known compounds, 7,7'-dihydroxy-6,8'-bicoumarin (bicoumol) (3), 3,4-dimethoxycinnamaldehyde (4), 6-hydroxy-7-methoxycoumarin (isoscopoletin), N-butylaniline, and vanillin, have been isolated from an ethyl acetate-soluble extract of the stem wood of Euphorbiaquinquecostata. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic data interpretation, and single-crystal X-ray diffraction analysis was used to confirm the structure and relative stereochemistry of 1. The absolute configuration of 1 was established by a convenient Mosher ester procedure in which the sample was treated with MTPA chlorides in deuterated pyridine directly in NMR tubes. All isolates were evaluated for the induction of quinone reductase in Hepa1c1c7 hepatoma cells and for the inhibition of the transformation of murine epidermal JB6 cells.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0202475