ABSTRACT
he chemical investigation of the methanolic crude extract of leaves of Diospyros iturensis gave us 15 known secondary metabolites identified as mixture of α-amyrenone (1) and β-amyrenone (2), β-amyrin (3), mixture of β-sitosterol (4) and stigmasterol (5), betulin (6), uvaol (7), betulinic acid (8), ursolic acid (9), corosolic acid (10), actinidic acid (11),11-O-p-hydroxybenzoylbergenin (12), bergenin (13) and mixture of stigmasterol glucoside (14) and β-sitosterol glucoside (15) respectively. The structures of secondary metabolites were elucidated with the help of NMR and mass spectral data and by comparison of their spectral data with literature.Among the fifteen isolated compounds, four compounds were identified for the first time in Diospyros genus.These included uvaol (7), corosolic acid (10), actinidic acid (11) and 11-O-p-hydroxybenzoylbergenin (12).Crude methanolic extract of leaves and four isolated compounds including betulin (6), betulinic acid (8), 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) were evaluated for their antiproliferative activity against two cancer cell lines CAL-27 and NCI-H460 by the MTT assay, antioxidant potential and inhibitory activity against the lipoxygenase and urease enzymes, respectively. The results indicated that the methanolic crude extract of leaves exhibited moderate antioxidant activity and was inactive against the two cancer cell lines. Betulin (6),11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate antioxidant and lipoxygenase inhibition with IC 50 = 65.8, 85.6, 82.5 µM and IC50 = 58.5, 95.2, 76.2 µM, respectively. Furthermore, 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate urease inhibition activity with IC50 values of 45.6 µM and 49.8 µM, respectively.
ABSTRACT
he chemical investigation of the methanolic crude extract of leaves of Diospyros iturensis gave us 15 known secondary metabolites identified as mixture of α-amyrenone (1) and β-amyrenone (2), β-amyrin (3), mixture of β-sitosterol (4) and stigmasterol (5), betulin (6), uvaol (7), betulinic acid (8), ursolic acid (9), corosolic acid (10), actinidic acid (11),11-O-p-hydroxybenzoylbergenin (12), bergenin (13) and mixture of stigmasterol glucoside (14) and β-sitosterol glucoside (15) respectively. The structures of secondary metabolites were elucidated with the help of NMR and mass spectral data and by comparison of their spectral data with literature.Among the fifteen isolated compounds, four compounds were identified for the first time in Diospyros genus.These included uvaol (7), corosolic acid (10), actinidic acid (11) and 11-O-p-hydroxybenzoylbergenin (12).Crude methanolic extract of leaves and four isolated compounds including betulin (6), betulinic acid (8), 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) were evaluated for their antiproliferative activity against two cancer cell lines CAL-27 and NCI-H460 by the MTT assay, antioxidant potential and inhibitory activity against the lipoxygenase and urease enzymes, respectively. The results indicated that the methanolic crude extract of leaves exhibited moderate antioxidant activity and was inactive against the two cancer cell lines. Betulin (6),11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate antioxidant and lipoxygenase inhibition with IC 50 = 65.8, 85.6, 82.5 µM and IC50 = 58.5, 95.2, 76.2 µM, respectively. Furthermore, 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate urease inhibition activity with IC50 values of 45.6 µM and 49.8 µM, respectively.
ABSTRACT
Phytochemical investigation of leaves, barks and roots of Nauclea vanderguchtii led to the isolation of sixteen compounds, which includes one citric acid derivative (2), one alkaloid (16), one peptide derivative (3), and twelve triterpenes (1, 4 - 13). These compounds were identified as rotundanonic acid (1), 2-hydroxy-1,2,3-propanetricarboxylic acid 2-methyl ester (2), asperphenamate (3), lupeol (4), stigmasterol (5), betulin (6), betulenic acid (7), stigmasterol 3-O-β-D-glucopyranoside (8), quinovic acid 3β-O-α-L-rhamnoside (9), α-amyrin (10), 3-oxoquinovic acid (11), ursolic acid (12), hederagenin (13), rotundic acid (14), clethric acid (15), and naucleficine (16) by the analysis of their NMR spectroscopic data including 2D NMR spectra and by comparison of their spectroscopic data reported in the literature. Compounds 1 and 3 were isolated for the first time in the genus Nauclea, and compound 2 was isolated for the first time from the Rubiaceae family. Complete NMR assignations for 1 have been published for the first time.