Two new lanostane triterpenes, methyl lucidenate N ( 1) and T-butyl lucidenate B ( 2), were isolated from the fruiting bodies of GANODERMA LUCIDUM together with five known compounds ( 3- 7). The structures of the two new triterpenes were established as methyl 3 β,7 β-dihydroxy-4,4,14 α-trimethyl-11,15-dioxo-5 α-chol-8-en-24-oate ( 1) and T-butyl 7 β,12 β-dihydroxy-4,4,14 α-trimethyl-3,11,15-trioxo-5 α-chol-8-en-24-oate ( 2) by extensive spectroscopic studies and chemical evidence. The effect of the isolated compounds ( 1- 7) on triglyceride (TG) accumulation, an indicator of adipocyte differentiation, during the differentiation of 3T3-L1 preadipocytes was examined. T-Butyl lucidenate B ( 2) reduced the TG accumulation significantly by 72 % at 80 µM compared to the untreated group. Furthermore, compound 2 effectively suppressed the GPDH activity in the cells. Consistent with the decrease in TG accumulation and GPDH activity, compound 2 suppressed the gene expressions of PPAR γ, C/EBP α, and SREBP-1c in a dose-dependent manner during differentiation. Our findings demonstrate that the lanostane triterpenes isolated in this study contribute to the inhibitory effect of the fruiting bodies of G. LUCIDUM on adipocyte differentiation in 3T3-L1 cells.
Aceriphyllum rossii ENGLER (Saxifragaceae), an endemic species in Korea, is a perennial herb growing on damp rocks along valleys, usually to a height of 30 cm. It has deeply lobed maple-like leaves and thick brown rhizomes. Clusters of small white flowers bloom on an upright stem in spring. The young leaflets and stems have been used for food. 1) Only a few studies have been carried out on the chemical constituents and biological activities of this plant. Triterpenes and flavonol glycosides have been reported as constituents of this plant and have been found to inhibit ACAT (acyl-CoA: cholesterol acyltransferase) and to possess antioxidant activity.2,3) In our continuing study for the discovery of novel antitumor agents from natural sources, we have found that a MeOH extract of the whole plant of A. rossii had cytotoxicity (Ͼ70% inhibition at 30 mg/ml) against the human leukemia HL-60 cell line. The cytotoxicity of the MeOH extract was concentrated in the hexane-and EtOAc-soluble fractions. Further phytochemical study on these fractions resulted in the isolation of two new triterpenes (1, 2), together with six known triterpenes (3-8). The present paper reports the isolation and structural elucidation of these triterpenes and their in vitro cytotoxicity against the K562 and HL-60 cell lines. Results and DiscussionThe MeOH extract of the whole plant of A. rossii was suspended in H 2 O and successively partitioned with hexane, EtOAc, and BuOH. The hexane-and EtOAc-soluble fractions, with cytotoxicity against both the K562 and HL-60 cell lines, were subjected to silica gel column chromatography to give several fractions that were further purified with column chromatography on silica gel to afford eight triterpenes, including the new compounds, 3a,23-isopropylidenedioxyolean-12-en-27-oic acid (1) and 23-hydroxy-3-oxoolean-12-en-27-oic acid (2), as well as six known triterpenes, 3-oxoolean-12-en-27-oic acid (3), 4) 3a-hydroxyolean-12-en-27-oic acid (4), 4) b-peltoboykinolic acid (5), 5) aceriphyllic acid A (6),2) oleanolic acid (7), 6) and gypsogenic acid (8) 7 Bioassay-guided fractionation of a MeOH extract of the whole plant of Aceriphyllum rossii (Saxifragaceae) led to the isolation of two new triterpenes, 3a a,23-isopropylidenedioxyolean-12-en-27-oic acid (1) and 23-hydroxy-3-oxoolean-12-en-27-oic acid (2), together with six known triterpenes, 3-oxoolean-12-en-27-oic acid (3), 3a a-hydroxyolean-12-en-27-oic acid (4), b b-peltoboykinolic acid (5), aceriphyllic acid A (6), oleanolic acid (7), and gypsogenic acid (8). The structures of these compounds were elucidated on the basis of physicochemical and spectroscopic analyses. These compounds were evaluated for in vitro cytotoxicity against the K562 and HL-60 cell lines. Olean-12-en-27-oic acid derivatives (1-6) exhibited considerable cytotoxicity against K562 and HL-60 cell lines with IC 50 values ranging from 12.2 to 28.7 m mM and from 12.1 to 25.8 m mM, respectively.
Four new lanostane triterpenes, butyl ganoderate A (1), butyl ganoderate B (2), butyl lucidenate N (3), and butyl lucidenate A (4), were isolated from the fruiting bodies of Ganoderma lucidum together with 14 known compounds (5-18). The structures of the new triterpenes were established by extensive spectroscopic studies and chemical evidence. In addition, the inhibitory effect of isolated compounds on adipocyte differentiation in 3T3-L1 cells was examined.
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