Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale.
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 IC50values 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.
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
Qingjuan
Q
Ma
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China. Electronic address: hanli@mail.neu.edu.cn.
Li
L
Han
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
Xiaoxu
X
Bi
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
Xingbo
X
Wang
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
Yu
Y
Mu
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
Peipei
P
Guan
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
Liya
L
Li
Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China. Electronic address: huangxs@mail.neu.edu.cn.
Xueshi
X
Huang
D034902:Alisma / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D002783:Cholestenones / Q000737:chemistry; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D008264:Macrophages / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D027343:Rhizome / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000520:alpha-Glucosidases / Q000378:metabolism
D000900:Anti-Bacterial Agents; D002783:Cholestenones; D004365:Drugs, Chinese Herbal; D012717:Sesquiterpenes; D014315:Triterpenes; C457233:alisol A 24-acetate; C526957:alisol B 23-acetate; C516685:alisol F; C000050:alisol A; D009569:Nitric Oxide; D000520:alpha-Glucosidases
Alisma orientale; Alismataceae; Anti-inflammatory activity; Antibacterial activity; Cytotoxicity; Sesquiterpenoid; Triterpenoid