Journal
JOURNAL OF NATURAL PRODUCTS
Volume 79, Issue 1, Pages 252-256Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.5b00801
Keywords
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Funding
- National Science and Technology Project of China [2011ZX09307-002-02]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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A pair of racemic indolizidine enantiomers, (+/-)-homocrepidine A (1), and a piperidine derivative, homocrepidine B (2), were isolated from Dendrobium crepidatum along with the known alkaloid crepidine (3). The racemic mixture of 1 was separated into a pair of enantiomers, (+)-1 and (-)-1, by HPLC using a chiral chromatographic substrate, which represents the first successful example of resolving indolizidine racemic mixtures. The absolute configurations of (+)-1 and (-)-1 were assigned from single-crystal X-ray diffraction data. The evaluation of anti-inflammatory activity with LPS-induced RAW 264.7 macrophages revealed that (+)-1 strongly inhibited the production of nitric oxide (IC50, 3.6 mu M) and significantly decreased the expression of inducible nitric oxide synthase, while (-)-1 and (+/-)-1 only had moderate inhibitory effects (IC50, 22.8 and 14.7 mu M). Compound 2 showed moderate anti-inflammatory activity (IC50, 27.6 mu M).
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