Further heliangolides and guaianolides from Eupatorium altissimum

Sesquiterpenoids Isolated from Eupatorium glehnii. Isolation of Guaiaglehnin A, Structure Revision of Hiyodorilactone B, and Genetic Comparison

“…The similar revision of the E,Z-geometry was reported in the case of eupachifolin-C (3). 19,20) The other 13 compounds were identified as eupachifolin-C (3), 19,20) hiyodorilactones A (4), C (6), and D (7), 3,4) eupaformosanin (8), 21) 3b-acetoxy-8b-tigloyloxyheliangolide (9), 22) 4E-deacetyl chromolaenide-4Ј-O-acetate (10), 23) 5Ј-deoxyeupaformosanin (11), 24) deacetyl hiyodorilactone D (12), 25) E,E,E-3-hydroxymethyl-7,11,15-trimethylhexadeca-2,6,10-triene-1,14,15-triol (13), 26) borneol glucoside (14), 27) thymol glucoside (15), [28][29][30] and eugenol glucoside (16). 31,32) Hiyodorilactones 3,4) from E. glehnii collected in Nagano Prefecture were isolated, but these substances were not found from the sample collected in Tokushima and Hokkaido.…”

Terpenoids, flavonoids and other constituents of Eupatorium betonicaeforme (Asteraceae)

“…1 Several studies on Eupatorium species have been reported, revealing a great number and diversity of secondary metabolites, where the sesquiterpenes lactones of the guaianolide, 2 germacranolide, 3 heliangolide, 4 and eudesmanolide types 5 are the most characteristic compounds. Flavonoids, 6 diterpenes, 7 benzofurans, 8 pyrrolizidine alkaloids, 9 chromenes 10 and thymol derivatives 11 are also common.…”

Seven New Sesquiterpene Lactones from Eupatorium chinense

“…Among them, eupachinitones E and H from E. chinense 5 were active against several tumor cell lines. In the continuation of our research work on this folklore medicinal herb, seven new sesquiterpenoids, namely eupatochinilides I-VII (1-7), together with eight known compounds, euponin (8), 6 mollisorin A (9), 7 niveusin B (10), 8 8β-(4'-acetoxy-tiglyloxy)-3β-hydroxy-6H β ,7H α -germacra-1(10)E,4E,11(13)trien-6,12-olide (11), 9 eupalinilide B (12), 10 8β-(4'hydroxytigloyloxy)-5-desoxy-8-desacyleuparotin (13), 11 3-deacetyeupalinin A (14), 12 and 15-hydroxyleptocarpin (15) (Scheme 1), 13 were isolated from its ethanolic extract of the whole plant of E. chinense L. Their structures were mainly demonstrated by spectroscopic methods, and a few of compounds 5-6 with some uncertainties of stereochemistry, which can not be assigned by the currently used spectroscopic methods, were completely solved by GIAO (gauge-independent atomic orbital) based 13 C NMR chemical shift alculations. Herein, we report the isolation and structural elu-cidation of the fifteen sesquiterpenoids.…”