Two new auronols, amaronols A (1) and B (2), were isolated from the bark of Pseudolarix amabilis, along with pseudolaric acid B (3), pseudolaric acid C (4), demethoxydeacetoxy-pseudolaric acid B (5), pseudolaric acid B-beta-D-glucoside (6), pseudolaric acid A-beta-D-glucoside (7), and myricetin (8). The structures of amaronols A and B were established by spectral data interpretation as 2,4,6-trihydroxy-2-[(3',4',5'-trihydroxyphenyl) methyl]-3(2H)-benzofuranone and 2,4,6-trihydroxy-2-[(3', 5'-dihydroxy-4'-methoxyphenyl) methyl]-3(2H)-benzofuranone, respectively. Antimicrobial testing results of the eight compounds indicated that only pseudolaric acid B was active against Candida albicans (MIC, 3.125 microg/mL; MFC, 6.25 microg/mL), while myricetin was marginally active against Trichophyton mentagrophytes (MIC, 50 microg/mL).
Antifungal assay-guided isolation of the 95% ethanol extract of the stems of Colubrina retusa yielded jujubogenin 3-O-alpha-L-arabinofuranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranoside (1), which showed modest growth-inhibitory effects against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus (MICs, 50 microg/mL). In addition, two new minor saponins, jujubogenin 3-O-alpha-L-arabinofuranosyl(1-->2)-[2-O-(trans, cis)p-coumaroyl-beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopy ranosi de (2), and jujubogenin 3-O-(5-O-malonyl)-alpha-L-arabinofuranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranoside (3), were obtained. Saponin 2 was marginally active against only C. neoformans, with a MIC of 50 microg/mL, while 3 was inactive. NMR spectroscopy was used extensively for the structure determination of these compounds. The previously reported ambiguity of the NMR assignments of jujubogenin saponins for carbons -26 to -29 was clarified by a comprehensive analysis of the NMR spectra of 1.
A new jujubogenin saponin was isolated from the stems of Colubrina retusa and identified as jujubogenin 3-O-alpha-L-arabinofuranosyl (1-->2)-[3-O-(trans)-p-coumaroyl-beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranoside (4) on the basis of chemical and spectroscopic data. The antimycobacterial activity expressed as minimum inhibitory concentration (MIC) for compound 4 was 10 microg/mL.
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