Anti-inflammation furanoditerpenoids from Caesalpinia minax Hance. (September 2015)

• Record Type: Journal Article
• Authors: Dong, Ruijuan; Yuan, Jiuzhi; Wu, Shilong; Huang, Jian; Xu, Xiaotong; Wu, Zhaohua; Gao, Huiyuan
• Is Part Of: Phytochemistry. Volume 117(2015:Sep.)
• Page Start: 325
• Page End: 331
• Publication Date: 2015-09
• Subjects: FUEMRDUPCPFBAQ-NFULFNSNSA-N -- KRHVJQKWELQGPY-QGEKGGCWSA-N -- OOUAFSXMWSCEGT-OEUDVJJISA-N -- JIKAOWSAQOJBMZ-DHUJPDJZSA-N -- KRTDSTYERVHJLI-SBRNPDNRSA-N -- OZMSPYFQLYZNFR-GWKQGQDASA-N; Caesalpinia minax Hance -- Caesalpinia -- A-seco-rearranged cassane -- Anti-inflammation activity -- Circular dichroism -- Conformation analysis; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2015.06.025
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract : Graphical abstract: Twelve furanocassane derivatives, including six previously unreported were isolated from the seeds of Caesalpinia minax Hance. Neocaesalminin A (1 ) was found with an unusual A- seco -rearranged cassane skeleton. The inhibitory effect on NO production for all compounds was evaluated in vitro. Furanoditerpenes were responsible for this herb's anti-inflammation activity. Highlights: Cassane furanoditerpenes, six previously unreported were isolated from seeds of Caesalpinia minax Hance. Neocaesalminin A, a furanoditerpene, has an unusual A- seco -rearranged cassane skeleton. Inhibitory effects on NO production for all compounds were evaluated in vitro. Cassane furanoditerpenes were responsible for the Caesalpinia minax Hance anti-inflammation activity. Abstract: Cassane skeletons are rare in nature, but often possess valuable medicinal properties. A furanoditerpenoid with an unusual A- seco -rearranged cassane skeleton, neocaesalminin A, and five furanoditerpenoids were isolated from seeds of Caesalpinia minax Hance, along with six known cassane derivatives, 7- O -acetyl-bonducellpin C, caesalmin F, caesalmin C, ζ-caesalmin, caesalmin E1 and caesalpinin K. Compound structures were determined by spectroscopy (HR-ESI-MS, UV, IR, 1D NMR, 2D NMR), X-ray crystallography and quantum chemical computation of electronic circular dichroism). Three of the previously known compounds exhibited significant inhibition of nitric oxide production of RAW264.7 macrophages stimulated by lipopolysaccharide (LPS).