Further Eudesmane Derivatives fromVerbesinaSpecies

Abstract

The aerial parts of VERBESINA PERSICIFOLIA DC afforded a new eudesmane derivative in addition to known compounds. The roots of V. SUBCORDATA gave also new eudesmane cinnamates in addition to several known ones as well as a 5alpha-hydroxybicyclogermacra-1 (10) E, 4 (15)-diene. A reinvestigation of V. VIRGINICA L. gave two new ( Z)-configurated coumarates. Furthermore the structures of some sesquiterpenes are revised. The structures were elucidated by highfield NMR spectroscopy and a few chemical reactions.

Eudesmane Derivatives from Verbesina turbacensis

“…In spite of this result, the stereochemistry in C-3 was evidenced on the basis of H-3 multiplicity signal and the magnitude of its coupling constants to H-2α (J 3.5 Hz) and H-2β a (J 11.5 Hz), which were in agreement with a β-equatorial oriented hydroxyl group. All the above data were consistent with the structure proposed for 5, and these ones also agree well with the spectroscopic data reported for the 6β-[cinnamoyloxy]-3β, 4α-dihydroxyeudesmane, a sesquiterpene previously isolated from V. persicifolia D.C. 6 and V. oncophora Rob. et Seat.…”

“…Species of the genus Verbesina (Asteraceae, tribe Heliantheae, subtribe Ecliptinae) have produced a range of eudesmane sesquiterpenes with cinnamate or a derived ester group, [1][2][3][4][5][6][7] of which, α-and β-verbesinolcoumarates were the first reported examples. 1,8 Several species also afforded elemanolides, 9,10 diterpenes, 11 flavonoids, 12 and biological active guanidines as Galegine, the toxic principle of V. enceloides Benth.…”

Verbesinosides A−F, 15,27-Cyclooleanane Saponins from the American Native Plant Verbesina virginica

“…The IR spectrum of 1 also showed a strong aromatic ester absorption at 1699 cm −1 , in accordance with the UV maxima at 214 and 261 nm 10. The free trimethoxybenzoic acid, namely, eudesmic acid, was isolated previously from Verbesina species 4. Based on the presence of the carboxylic carbon (δ 178.1), two olefinic carbons (δ 137.8, qC and 121.1, CH), and one oxygen-bearing methine carbon (δ 88.9), resonating in the downfield region that are typical of oleanolic acid derivatives,11 we believed initially compound 1 to be an oleanane-like triterpenoid skeleton attached to a sugar moiety of three monosaccharides and a trimethoxybenzoyl moiety.…”

Phytomedicinal aspects of sesquiterpenoid peroxides: Origin, structures and biological activity

“…Hydroperoxide of dihydroartemisinic acid (26) was isolated from the plant Artemisia annua (Wallaart et al, 1999), and compound (27) was isolated from leaves of Cacalia tangutica [62], and the Mexican tree Robinsonecio gerberifolius afforted hydroperoxide (28) [63]. Hydroperoxyeudesmane cinnamate (29) and compound (39) were found in extracts of Brintonia discoidea [64], and Verbesina subcordata [65].…”