New Triterpene Esters from Flowerheads ofArnica lonchophylla

Abstract

From the flowerheads of Arnica lonchophylla Greene ssp. lonchophylla Maguire (Asteraceae), a variety of mono-, di- and trihydroxytriterpenes of the oleanane, ursane, lupane and dammarane types were isolated and their structures elucidated by EI and CI mass spectrometry and extensive NMR spectroscopic analysis. Most of the compounds are esterified at position 3 with lauric, myristic, palmitic and stearic acids. Several ester derivatives of known triterpenes represent new natural products. The triterpenetriols 20(30)-taraxasten-3beta,16beta,21alpha-triol (arnitriol A) and lupane-3beta,16beta,20-triol, both isolated in the form of their C3-fatty acid ester derivatives, possess hydroxylation patterns which have not been described previously. Besides small amounts of triterpenetriol esters, the lauric, myristic, palmitic and stearic acid esters of arnidiol, faradiol, maniladiol and calenduladiol were also identified in the flowerheads of A. montana (Arnicae flos Ph. Eur.), A. chamissonis ssp. foliosa and A. angustifolia ssp. attenuata. A search for sesquiterpene lactones in the flowers of A. lonchophylla resulted in the identification of small amounts of helenalin and 11alpha,13-dihydrohelenalin.

Flavonoids and Triterpenoid Saponins from Pimenta dioica (Merr.) L

“…and 3 with related published data[3,6,[9][10][11], it was expected that the two sp2 olefinic carbons in the structure of 3 were C-13 and C-18, assigned at δ 137.7 and 124.8 instead of δ 143 and 121 for C-13 and C-12, respectively, in the common olean-type aglycones. The change of the position of the double bond resulted in a clear effect on the δ-values of some adjacent carbons, for example δ 21.0 (C-11), 25.6 (C-12) and 38.4 (C-19) in the case of 3, instead of ~ δ 23.0, 121.5, and 46.0 in other related olean 11,12-ene structures.…”

“…Three triterpenoid saponins (1)(2)(3) and four flavonoids (4)(5)(6)(7) were isolated from the desalted and defatted 80% methanol extract of P. dioica leaves through consecutive column chromatographic separations, and characterized on the basis of chemical and physicochemical analyses and comparison with published data [2][3][4][5][6][7][8] [aglycone-H] -, corresponding to the loss of a pentoside from the last fragment. These data, together with the acid hydrolysis that afforded arabinose, rhamnose and galactose in the aqueous phase, were compatible with a structure of hydroxyolean 28-rhamnosyl-galactosyl-galactosyl ester with an O-rhamnosyl-pentoside, most probably at C-3 [4] (co-TLC and PC with the authentic samples).…”

Plant Resources, 13C-NMR Spectral Characteristic and Pharmacological Activities of Dammarane-Type Triterpenoids

“…In order to complete and enrich the resource investigation of DTT, we summarize the literatures (1965–2016) describing this type of triterpenoids, extracted from various botanicals. In Table 1, 136 species, from Araliaceae, Cucurbitaceae, Rhamnaceae, and Meliaceae families, together with 42 others are summarized [4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,…”

2-Hydroxydiplopterol, a new cytotoxic pentacyclic triterpenoid from the halotolerant fungus Aspergillus variecolor B-17

“…Hopane type pentacyclic triterpenoids are common secondary metabolites of plants and fungi (Isaka et al, 2007;Wachter et al, 1999;Kumar et al, 1996;Shiojima and Ageta, 1994;Wu et al, 1990;Nielsen and Smedsgaard, 2003;Wilkins et al, 1989;Boonphong et al, 2001;Tsuda and Isobe, 1965;Ulubelen et al, 1994;Schmidt et al, 2004;Van Eijka et al, 1986;Toyota and Asakawa, 1993). These compounds shared an icosahydro-1H-cyclopenta[a]chrysene skeleton.…”