Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale. (November 2016)

• Record Type: Journal Article
• Authors: Ma, Qingjuan; Han, Li; Bi, Xiaoxu; Wang, Xingbo; Mu, Yu; Guan, Peipei; Li, Liya; Huang, Xueshi
• Is Part Of: Phytochemistry. Volume 131(2016:Nov.)
• Page Start: 150
• Page End: 157
• Publication Date: 2016-11
• Subjects: Alisma orientale -- Alismataceae -- Triterpenoid -- Sesquiterpenoid -- Antibacterial activity -- Anti-inflammatory activity -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2016.08.015
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Sixteen triterpenoids and nine sesquiterpenoids were isolated from the rhizome of Alisma orientale . Structures of 16-oxo-11-anhydroalisol A 24-acetate, 13 β, 17 β -epoxy-24, 25, 26, 27-tetranor-alisol A 23-oic acid, 1 α H, 5 α H-guaia-6-ene-4 β, 10 β -diol, and alisguaiaone were elucidated by comprehensive spectroscopic data analysis. The cytotoxic, antibacterial, antifungal, anti-inflammatory, and α-glucosidase inhibitory activities of isolated terpenoids were evaluated. Triterpenoids alisol A, alisol A 24-acetate, 25- O -ethylalisol A, 11-deoxyalisol A, alisol E 24-acetate, alisol G, alisol B 23-acetate and sesquiterpenoids 1 α H, 5 α H-guaia-6-ene-4 β, 10 β -diol, 10-hydroxy-7, 10-epoxysalvialane exhibited cytotoxicities against the three tested human cancer cell lines with IC50 values ranging from 11.5 ± 1.7 μM to 76.7 ± 1.4 μM. Triterpenoids alisol A, 25- O -ethylalisol A, 11-deoxyalisol A, alisol E 24-acetate, alisol G, and 25-anhydroalisol F showed antibacterial activities against the Gram-positive strains Bacillus subtilis and Staphylococcus aureus with MIC values of 12.5–100 μg/mL. Sesquiterpenoid 4 β, 10 β -dihydroxy-1 α H, 5 β H-guaia-6-ene exhibited antibacterial activity against B. subtilis with an MIC value of 50 μg/mL, and 10-hydroxy-7, 10-epoxysalvialane exhibited activity against S. aureus with an MIC value of 100 μg/mL. Compounds 16-oxo-11-anhydroalisol A 24-acetate, alisol F, 25-anhydroalisol F, and alisguaiaone exhibited inhibitory effects on lipopolysaccharide-induced NO production in RAW 264.7 macrophage cells. None of the compounds showed obvious inhibitory activity against α-glucosidase. Graphical abstract: Sixteen triterpenoids and nine sesquiterpenoids were isolated from the rhizome of Alisma orientale . Four previously undescribed terpenoids among them were elucidated by comprehensive spectroscopic data analysis. Highlights: Twenty five terpenoids were isolated from the rhizome of Alisma orientale . Four previously undescribed terpenoids were characterized. Nine compounds exhibited weak to moderate cytotoxicity. Eight compounds showed antibacterial activities against B. subtilis or S. aureus . Four compounds presented inhibition against NO production.