Cytotoxic Activity of Lupane-Type Triterpenes fromGlochidion sphaerogynumandGlochidion eriocarpumTwo of which Induce Apoptosis

Abstract

Six known lupanes lupenone ( 1), 3- epi-lupeol ( 2), glochidone ( 4), glochidonol ( 5), glochidiol ( 6) and lup-20(29)-ene-1beta,3beta-diol ( 7) were isolated from the roots and stem wood of Glochidion eriocarpum and three, 5, 6 and lup-20(29)ene-3alpha,23-diol ( 3), were isolated from the roots and stem wood of Glochidion sphaerogynum. Compounds were identified by (1)H- and (13)C-NMR techniques. Triterpenes 2 - 7 were tested against the growth of three human tumor cell lines, MCF-7, NCI-H-460 and SF-268. Lupanes 3, 5, and 6 exhibited strong inhibitory effects against all three; thus GI (50) values for 3 were 12.7 +/- 3.7, 17.9 +/- 1.1 and 17.9 +/- 0.5, for 5 9.0 +/- 3.7, 4.9 +/- 0.2 and 9.8 +/- 0.5, and for 6 6.63 +/- 0.7, 7.5 +/- 0.5 and 9.7 +/- 0.3.3. Epilupeol was less active, with GI (50) values of 75.6 +/- 11.7, 86.1 +/- 12.4 and 80.9 +/- 2.6 while 7 was moderately active only against MCF-7 (GI (50) = 79.2 +/- 2.4). Additional studies indicated that triterpenes 5 and 6 exerted their antiproliferative activity through the involvement of apoptosis while triterpene 3 did not.

Isolation and cytotoxicity of triterpenes from the roots of Phyllanthus pulcher Wall. ex Mll. Arg. (Euphorbiaceae)

“…Compound 4 is reported for the first time from a natural Bagalkotkar et al 185 source while 1 and 3 are isolated for the first time from Euphorbiaceae family. Compounds 1, 2 and 5 were identified by comparison of their spectral data with the literature values, which supported the structures as 3α-acetoxyl-25-hydroxyolean-12-en-28-oic acid (Chun et al, 2002) and, glochidone and glochidonol (Puapairoj et al, 2005), respectively. Although 12(13)-dehydro-3α-acetoxyolean-28-oic acid (3) was previously reported (Bohlmann et al, 1979), here we are representing the complete data for the first time.…”

Efecto in vitro de los terpenos lupeol y casearina G sobre células sanguíneas y tumorales

“…En esta investigación, el lupeol mostró muy poco efecto sobre las células tumorales estudiadas en comparación con lo reportado por otros investigadores 17,18 que utilizaron concentraciones mucho más altas 18 o compuestos estructuralmente diferentes 17 al lupeol utilizado en nuestro trabajo.…”

NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

“…In a second study, the hexane and EtOAc extracts of the roots of the specimen collected in the central Brazilian cerrado were submitted to several chromatographic columns, which eventually lead to the identification of the triterpenes α-amyrin, β-amyrin, 26 oleanolic acid, 27 glochidonol, 28 and the mixture of stigmasterol, β-sitosterol and campesterol. 29,30 The new quinone diterpene derivative was identified by 1 H NMR and 2D NMR experiments, such as HSQC, HMBC, and 1D NOE (Table 1), as well high-resolution mass spectrometry.…”

“…31 All the compounds isolated from the roots of the second specimen were identified through comparison of their spectral data with the literature. [26][27][28][29][30] …”