Epi-Ililic acid from Alcantara Ekmaniana

doi:10.1016/S0031-9422(00)95289-0

Phytochemistry

Volume 21, Issue 2, 1982, Pages 456-457

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Abstract

The aerial parts of Alcantara ekmaniana afforded, in addition to known compounds, epi-ilicic acid. The furanogermacranolides isolated indicate a close relationship between this genus and other members of the same tribe.

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J.B. Harborne et al.

There are more references available in the full text version of this article.

Cited by (13)

Three new sesquiterpenes from Tithonia diversifolia and their anti-hyperglycemic activity
2012, Fitoterapia
Citation Excerpt :
Chemical studies on this species have resulted in sesquiterpene lactones, chromene, and flavone [13–16]. The present study is our ongoing research of antidiabetic active metabolites from T. diversifolia, involving the isolation and identification of 14 sesquiterpenes, including three new sesquiterpenes: tagitinin G (1), tagitinin H (2), tagitinin I (3), and 11 known sesquiterpenes: tirotundin 3-O-methyl ether (4) [15], deacetylvguiestin (5) [16], 1β-hydroxydiversifolin-3-O-methyl ether (6) [17], tagitinin C (7) [16], 1β-hydroxytirotundin 3-O-methyl ether (8) [12], 1β-hydroxytirotundin-1,3-O-dimethyl ether (9) [18], tagitinin F-3-O-methyl ether (10) [17], tagitinin F (11) [19], tagitinin A (12) [16], 3β-acetoxy-4α-hydroxyeduesm-11(13)-en-12-oic acid (13) [20], ilicic acid (14) [21,22]. In addition, the anti-hyperglycemic activities of compounds 1-14 were evaluated by glucose uptake in 3T3-L1 adipocytes.
Three new germacrane sesquiterpenes (1), (2), (3), along with eleven known sesquiterpenes, namely, tirotundin-3-O-methyl ether (4), deacetylvguiestin (5), 1β-hydroxydiversifolin-3-O-methyl ether (6), tagitinin C (7), 1β-hydroxytirotundin-3-O-methyl ether (8), 1β-hydroxytirotundin-1,3-O-dimethyl ether (9), tagitinin F-3-O-methyl ether (10), tagitinin F (11), tagitinin A (12), 3β-acetoxy-4α-hydroxyeduesm-11(13)-en-12-oic acid (13) and ilicic acid (14) were isolated from the aerial parts of Tithonia diversifolia. Their structures were established by spectroscopic analysis, while the relative configuration of compound 1 was confirmed by X-ray diffraction analysis. In addition, compounds 1–14 were evaluated in vitro for their anti-hyperglycemic activity by glucose uptake in 3T3-L1 adipocytes. It was found that 10 μg/mL 1, 3, 6 and 8 could significantly increase glucose uptake without significant toxic effects.
Jasonol, a rare tricyclic eudesmane sesquiterpene and six other new sesquiterpenoids from Jasonia candicans
1998, Tetrahedron
The extract of the leaves of Jasonia candicans yielded, seven new sesquiterpenes and sesquiterpene lactones including a eudesmane containing a rare type of 6/6/4 membered ring system, two 7-epi-eudesmanes (12-hydroxyisointermedeol and 7-epi-ilicic acid), two guaianolides (inuviscolide and its 8-epi- derivative), iphionane and cadinane-triol derivatives. The structures were elucidated by spectroscopic analysis particularly high-resolution 1D and 2D NMR spectroscopy and the extensive NOE analysis.
Sesquiterpene lactones, lignans and aromatic esters from Cheirolophus species
1994, Phytochemistry
Oxygenated nerolidol esters and eudesmane acids from Inula viscosa
1991, Phytochemistry
Eremophilane derivatives and other constituents from Haeckeria species and further Australian inuleae
1991, Phytochemistry
From the aerial parts of two Haeckeria species, in addition to known compounds, 19 new eremophilan-12-oic acids, one being a seco-nor derivative, two eudesman-12-oic acids and three germacran-12-oic acids were isolated. The other species only gave known compounds which in part are of taxonomic relevance. The structures were elucidated by high field NMR spectroscopy. The chemotaxonomic aspects are discussed briefly.
Evolution of sesquiterpene lactones in asteraceae
1986, Biochemical Systematics and Ecology

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^☆: Part 391 in the series “Naturally Occuring Terpene Derivatives”. For Part 390 see Bohlmann, F., Zdero, C., King, R.M. and Robinson, H. (1982) Phytochemistry21 (in press).

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Short reportEpi-Ililic acid from Alcantara Ekmaniana☆

Abstract

Phytochemistry

Phytochemistry

Phytochemistry

Short report
Epi-Ililic acid from Alcantara Ekmaniana☆