15-Deoxygoyazensolide, a new heliangolide from Vanillosmopsis erythropappa

Phytochemistry
1976.0

Abstract

Two new compounds from Compositae plants were isolated and structurally determined. 1) 15-Deoxygoyazensolide (la), a new heliangolide, was obtained from Vanillosmopsis erythropappa herbaceous parts via hexane extraction, silica gel-AgNO3 chromatography, and preparative TLC. It has formula C20H20O6 (HRMS), mp 132-134°, [α]D -38°, with γ-lactone (conjugated exocyclic methylene: IR 1770/1650 cm⁻¹, UV end absorption, NMR δ 6.21/5.45 ppm) and methacrylic ester (IR 1710/1640 cm⁻¹, NMR 1.82/6.01/5.54 ppm, MS M-C4H5O). Its NMR spectrum matched goyazensolide (lb) except C-15 (lb's hydroxymethylene replaced by vinyl methyl, δ 2.06 ppm), with stereochemistry based on lb. 2) A new diterpene galactoside from Acanthuspermum hispidum aerial parts (alcoholic extract) gave a hexaacetate (C35H56O16, MS). Acid hydrolysis yielded galactose; ¹H NMR indicated β-D-galactosidopyranoside. Data included Me-singlets, secondary OCOMe, CH2C(Me)=CHCH2OAc, methylene (4.91/5.10 ppm), and secondary nCHOR, consistent with a bicyclic diterpene triol glycoside (structure 1, absolute configuration unclear). Manganese dioxide oxidation showed primary allylic OH; ¹³C NMR (off-resonance, Yb(fod)3) confirmed structure.

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