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Isolation of two rare N-glycosides from Ginkgo biloba and their anti-inflammatory activities.


ABSTRACT: Two rare N-?-D-glucopyranosyl-1H-indole-3-acetic acid conjugates, N-[2-(1-?-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-glutamic acid (1) and N-[2-(1-?-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-aspartic acid (2) were isolated from Ginkgo biloba. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. In addition, a simplified and efficient synthetic route for compounds 1 and 2 is also disclosed to determine the absolute configurations of them. This concise syntheses of compounds 1 and 2 may facilitate studies of the biology of this type alkaloids. Compounds 1 and 2 were also tested for their cytotoxic and anti-inflammatory activities. The biological evaluation showed that compounds 1 and 2 led to the decrease of interleukin (IL)-6, nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 at mRNA level in lipopolysaccharide (LPS)-stimulated murine macrophage RAW264.7 cells.

SUBMITTER: Cheng JT 

PROVIDER: S-EPMC7138816 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Isolation of two rare N-glycosides from Ginkgo biloba and their anti-inflammatory activities.

Cheng Jin-Tang JT   Guo Cong C   Cui Wen-Jin WJ   Zhang Qing Q   Wang Shu-Hui SH   Zhao Qing-He QH   Liu De-Wen DW   Zhang Jun J   Chen Sha S   Chen Chang C   Liu Yan Y   Pan Zheng-Hong ZH   Liu An A  

Scientific reports 20200407 1


Two rare N-β-D-glucopyranosyl-1H-indole-3-acetic acid conjugates, N-[2-(1-β-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-glutamic acid (1) and N-[2-(1-β-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-aspartic acid (2) were isolated from Ginkgo biloba. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. In addition, a simplified and efficient synthetic route for compounds 1 and 2 is also disclosed to determine the absolute configurations of them. This concise syntheses of compo  ...[more]

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