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Bergamotane-type sesquiterpenes from the leaves and twigs of Illicium oligandrum and their anti-inflammatory activities.

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Title: Bergamotane-type sesquiterpenes from the leaves and twigs of Illicium oligandrum and their anti-inflammatory activities.
Authors: Li, Wen-Rui1 (AUTHOR), Zhao, Jia-Ying1,2 (AUTHOR), Li, Mi1 (AUTHOR), Wang, Xiao-Jing1 (AUTHOR), Su, Guo-Zhu1 (AUTHOR), Wang, Hai-Qiang1 (AUTHOR), Li, Li1,2 (AUTHOR) lili@imm.ac.cn, Du, Guan-Hua2 (AUTHOR), Wang, Ru-Bing1 (AUTHOR) wangrubing@imm.ac.cn, Ma, Shuang-Gang1 (AUTHOR) mashuanggang@imm.ac.cn
Source: Phytochemistry. May2023, Vol. 209, pN.PAG-N.PAG. 1p.
Subjects: Sesquiterpenes, Anti-inflammatory agents, Caryophyllene, Twigs, Ketones, Circular dichroism, Schisandra
Abstract: Eight undescribed β-bergamotene-type sesquiterpene oliganins A-H (1–8) and one known α-bergamotene-type sesquiterpene (9) were isolated from the leaves and twigs of Illicium oligandrum Merr. & Chun. The structures of compounds 1 – 8 were elucidated by extensive spectroscopic data, and the absolute configurations were determined by using a modified Mosher's method and electronic circular dichroism calculations. The isolates were further evaluated in terms of their anti-inflammatory potential on nitric oxide (NO) generation in lipopolysaccharide-stimulated RAW264.7 and BV2 cells. Compounds 2 and 8 exhibited potent inhibitory effects on the production of NO with IC 50 values ranging from 21.65 to 49.28 μM, which were greater than or comparable to those of dexamethasone (positive control). β-Bergamotene-type sesquiterpenes with an α,β-unsaturated ketone exhibited potential nitric oxide inhibitory effect in LPS-stimulated RAW264.7 and BV2 cells with IC 50 values ranging from 21.65 to 49.28 μM, which were stronger or comparable than those of dexamethasone. [Display omitted] • Eight undescribed β-bergamotene-type sesquiterpenes were isolated from Illicium oligandrum. • The stereochemistry of epimeric isomers was determined by ECD calculations. • Two sesquiterpenes with an α, β-unsaturated ketone exhibited potent NO inhibitory activity. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:Eight undescribed β-bergamotene-type sesquiterpene oliganins A-H (1–8) and one known α-bergamotene-type sesquiterpene (9) were isolated from the leaves and twigs of Illicium oligandrum Merr. & Chun. The structures of compounds 1 – 8 were elucidated by extensive spectroscopic data, and the absolute configurations were determined by using a modified Mosher's method and electronic circular dichroism calculations. The isolates were further evaluated in terms of their anti-inflammatory potential on nitric oxide (NO) generation in lipopolysaccharide-stimulated RAW264.7 and BV2 cells. Compounds 2 and 8 exhibited potent inhibitory effects on the production of NO with IC 50 values ranging from 21.65 to 49.28 μM, which were greater than or comparable to those of dexamethasone (positive control). β-Bergamotene-type sesquiterpenes with an α,β-unsaturated ketone exhibited potential nitric oxide inhibitory effect in LPS-stimulated RAW264.7 and BV2 cells with IC 50 values ranging from 21.65 to 49.28 μM, which were stronger or comparable than those of dexamethasone. [Display omitted] • Eight undescribed β-bergamotene-type sesquiterpenes were isolated from Illicium oligandrum. • The stereochemistry of epimeric isomers was determined by ECD calculations. • Two sesquiterpenes with an α, β-unsaturated ketone exhibited potent NO inhibitory activity. [ABSTRACT FROM AUTHOR]
ISSN:00319422
DOI:10.1016/j.phytochem.2023.113617