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

Abstract

Two new compounds, an ent-isopimarane-type diterpene, 3R,12R-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 Euphorbia quinquecostata. 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.