Kukoamine A has been known for decades as an anti-inflammatory and hypotensive principle of Chinese medicinal plant extract from Lycium root, bark, and fruit. The recent pharmacological significance of this alkaloid makes it a potential therapeutic target for the pharmaceutical industry. We accomplished the synthesis of kukoamine A in a 73% yield over four steps starting from cheaper commercial reagents, ambient reaction conditions, and minimal purification efforts.
New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H2O2 (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18βH-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18βH-olean-9,12-diene-2,3,30-trioic acid.
A new oleanane-type triterpene glycoside, 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl ester, was isolated from the aqueous-ethanolic extract of the seeds of Nephelium lappaceum L. The structure elucidation of this compound was based on analyses of spectroscopic data, including 1D and 2D NMR and HR-ESI-MS techniques, and by comparing their NMR data with those reported in the literature.
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