Caesalminaxins O-T, cassane diterpenoids from the seeds of Caesalpinia minax and their anti-inflammation

Six previously undescribed cassane diterpenoids, named caesalminaxins O-T (1–6), together with 28 known compounds (7–34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diff...

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Bibliographic Details
Published in:Fitoterapia 2019-04, Vol.134, p.50-57
Main Authors: Ruan, Qing-Feng, Zhou, Xing-Hong, Jiang, Shi-Qin, Yang, Bao, Jin, Jing, Cui, Hui, Zhao, Zhong-Xiang
Format: Article
Language:English
Subjects:
Anti-inflammatory activity
Caesalpinia
Caesalpinia minax
Cassane diterpenoids
Diterpenes
Enol group
Indomethacin
Lipopolysaccharides
NMR
Nuclear magnetic resonance
Organic chemistry
Quantum chemistry
Seeds
X-ray diffraction
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Summary:Six previously undescribed cassane diterpenoids, named caesalminaxins O-T (1–6), together with 28 known compounds (7–34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Among the undescribed diterpenoids, compound 6 that possessed an unusual enol group at C-7 with a highly deshielded 1H NMR signal was the first example in cassane diterpenoids. All of the isolates were evaluated for their inhibitory activity against lipopolysaccharide-activated NO production in RAW264.7 cells. Compound 16 showed moderate inhibitory activity with an IC50 value of 17.3 μM, which was more potent than the positive control (indomethacin, IC50 = 29.7 μM). [Display omitted]
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2019.02.004