1987
DOI: 10.1055/s-2006-962614
|View full text |Cite
|
Sign up to set email alerts
|

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.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2
1

Citation Types

3
12
0

Year Published

1988
1988
2019
2019

Publication Types

Select...
8
1

Relationship

0
9

Authors

Journals

citations
Cited by 22 publications
(15 citation statements)
references
References 10 publications
3
12
0
Order By: Relevance
“…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.…”
Section: Resultssupporting
confidence: 91%
See 1 more Smart Citation
“…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.…”
Section: Resultssupporting
confidence: 91%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Resultssupporting
confidence: 65%
“…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].…”
Section: Sesquiterpenoid Hydroperoxidesmentioning
confidence: 99%