Apotirucallane and Tirucallane Triterpenoids from Luvunga sarmentosa

Abstract

The leaves of Luvunga sarmentosa yielded two new apotirucallane triterpenoids, 3-epi-skimmiarepin A (1) and 21,23-epoxy-7alpha,21-dihydroxyapotirucalla-14,24-dien-3-one (2), and a new tirucallane triterpene, 3-epi-flindissol (3). Because of a hemiacetal functionality at C-21, all compounds occurred as mixtures of 21-epimers. 3-epi-Skimmiarepin A (1) and 3-epi-flindissol (3) were oxidized to the corresponding gamma-lactones. The structures have been elucidated on the basis of mass and NMR spectroscopic methods.

Further terpenoids from Euphorbia tirucalli

“…The large coupling constants of H-3 [δH 3.27, dd, (J = 11.0, 6.0)] indicated its axial α-position, thus deducing the equatorial β-position of 3-OH moiety [57][58][59]. The stereochemistry of the tetracyclic nucleus and the orientation of the side chain could be further inferred from the key NOE correlations emphasized in Fig.…”

Lepidotrichilins A and B, New Protolimonoids with Cytotoxic Activity from Trichilia Lepidota (Meliaceae)

“…The compounds 3, 4 and 5 were identified as 21,23-epoxy-7α-21α-dihydroxyapotirucalla-14,24-dien-3-one, and 21,23-epoxy-7α-21β-dihydroxyapotiru-calla-14,24-dien-3-one previously isolated from Luvunga sarmentosa [10] and dysorane D isolated from Dysoxylum roseum [11].…”

Brazoxide A, a New Tirucallane Triterpene fromPilocarpus spicatussubsp.AracatensisKaastra

“…; CDCl 3 ), HMBC, COSY, and NOESY data for compound 1, and 1 H-and 13 C-NMR (300 and 75 MHz, resp. ; CDCl 3 ) for 3-epi-flindissol 17…”