Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale

  • Phytochemistry. 2016 Nov;131:150-157. doi: 10.1016/j.phytochem.2016.08.015.
Qingjuan Ma  1 ,  Li Han  2 ,  Xiaoxu Bi  1 ,  Xingbo Wang  1 ,  Yu Mu  1 ,  Peipei Guan  1 ,  Liya Li  1 ,  Xueshi Huang  3
Affiliations
  • 1. Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
  • 2. Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China. Electronic address: [email protected].
  • 3. Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China. Electronic address: [email protected].
PMID: 27615692 DOI: 10.1016/j.phytochem.2016.08.015
Abstract

Sixteen triterpenoids and nine sesquiterpenoids were isolated from the rhizome of Alisma orientale. Structures of 16-oxo-11-anhydroalisol A 24-acetate, 13β,17β-epoxy-24,25,26,27-tetranor-alisol A 23-oic acid, 1αH,5αH-guaia-6-ene-4β,10β-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 1αH,5αH-guaia-6-ene-4β,10β-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 4β,10β-dihydroxy-1αH,5βH-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.

Keywords
Alisma orientale; Alismataceae; Anti-inflammatory activity; Antibacterial activity; Cytotoxicity; Sesquiterpenoid; Triterpenoid.
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