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Anti-inflammatory pregnene steroids from the oleo-gum resin of Commiphora mukul: in-vitro and in-silico studies
Phytochemical investigation of a methanolic extract derived from the oleo-gum resin of Commiphora mukul resulted in the isolation of seven pregnene-type steroids (1-7), including a new compound named commukulsterol A (1). Their structures were decided by extensive analyses of 1D, 2D-NMR and Mass spe...
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Published in: | Phytochemistry letters 2024-12, Vol.64, p.106-116 |
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Main Authors: | , , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites |
Online Access: | Get full text |
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Summary: | Phytochemical investigation of a methanolic extract derived from the oleo-gum resin of Commiphora mukul resulted in the isolation of seven pregnene-type steroids (1-7), including a new compound named commukulsterol A (1). Their structures were decided by extensive analyses of 1D, 2D-NMR and Mass spectra. The relative configurations of commukulsterols A (1) and B (2) were determined via DFT calculations of their 1H and 13C chemical shifts, followed by DP4+ statistical analysis. Absolute configurations were then decided by biogenetic similarities and specific rotations. Such analyses led to the revision of the structure of 2, initially elucidated as 20S-acetyloxy-4-pregnene-3,16-dione, to pro-20R. 1-7 showed varying inhibitory effects on LPS-induced NO release in RAW264.7 macrophages, with IC50 values ranging from 7.6 to 53.9 μM for (1-6), while 7 didn’t show activity up to 100 μM. On the other hand, molecular docking revealed that 3 &4 could bind to the catalytic site of inducible nitric oxide synthase (iNOS). Moreover, molecular dynamics simulation of 3 &4 in association with iNOS were examined for 200 ns, revealing adequate stability. ADMET analysis indicated good oral bioavailability and drug-like properties. The observed chemical profile highlighted a unique chemical relationship between Burseraceae and Simaroubaceae families.
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•Seven pregnane steroids were isolated from the oleo gum resin of Commiphora muckul.•A new compound and revised structure of a known compound were decided.•Structures were identified by NMR & MS, while configurations by DFT calculations.•Compounds were tested for their anti-inflammatory activity and ADMET properties were predicted.•Molecular docking asserted by molecular dynamics evaluated the activity on molecular level. |
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ISSN: | 1874-3900 |
DOI: | 10.1016/j.phytol.2024.10.006 |