Alisol F

Zhongguo Zhong Yao Za Zhi. 2009 Apr;34(8):994-8.

Chemical constituents of Alisma orientalis and their immunosuppressive function.[Pubmed: 19639784]

To investigate the chemical constituents with immunosuppressive function from Alisma orientalis.
METHODS AND RESULTS:
The chemical constituents were isolated and purified by kinds of column chromatography and its structures were elucidated by NMR spectra and physicochemical properties. Its immunocompentence of lymphocytes taken from spleen of mouse were examined by MTT assay. Twelve compounds were isolated and identified as clovandiol (1), orientalol E (2), alismoxide (3), alismol (4), 4alpha, l0alpha-dihydroxy-5beta-H-guaj-6-en (5), alismorientols A (6), Alisol F (7), alisol A (8), 13beta,17beta-epoxy alisol A (9), alisol B 23-acetate (10), 1H-indole-3-carboxylic acid (11) and cuccinic acid (12). Compounds 9, 10 and alisol A 24-acetate showed immunosuppressive function.
CONCLUSIONS:
Compounds 1, 5, 11 and 12 were isolated firstly from this genus,and the NMR spectra data of 1 were corrected firstly, some protostan-type triterpenoids may be developed as new drug with immunosuppressive function.

Bioorg Med Chem Lett. 1999 Nov 1;9(21):3081-6.

Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate.[Pubmed: 10560729]

The methanolic extract from a Chinese herbal medicine, the rhizome of Alisma orientale, was found to exhibit inhibitory activity of nitric oxide (NO) production in lipopolysaccharide (LPS)activated macrophages.
METHODS AND RESULTS:
Novel triterpenes, alismaketones-B 23-acetate and -C 23-acetate, were isolated from the active extract together with eight sesquiterpenes and eighteen protostane-type triterpenes. The absolute stereostructures of new triterpenes were characterized on the basis of chemical and physicochemical evidence, which included the chemical correlations with known triterpenes. The guaiane-type sesquiterpenes (alismol, orientalols A and C) and protostane- and seco-protostane-types triterpenes (alisols C monoacetate, E-23-acetate, F, H, I, L-23-acetate, and M-23-acetate, alismaketones-B 23-acetate and -C 23-acetate, alismalactone 23-acetate, and 3-methylalismalactone 23-acetate) inhibited LPS-induced NO production (IC50 = 8.4-68 microM). Other triterpenes (alisols A, A monoacetate, B, B monoacetate, E, G, K-23-acetate, and N-23-acetate and 11-deoxyalisol B) also showed the potent inhibitory activity, but they showed cytotoxic effects more than 30 microM (MTT assay). In addition, alismol and Alisol F were found to suppress iNOS induction.

Planta Med. 2006 Aug;72(10):951-4.

A new triterpene and anti-hepatitis B virus active compounds from Alisma orientalis.[Pubmed: 16858666 ]

A new triterpenoid named alisol O ( 1) was isolated from the rhizomes of Alisma orientalis, together with six known compounds: alisol A 24-acetate ( 2), 25-anhydroalisol A ( 3), 13 beta,17 beta-epoxyalisol A ( 4), alisol B 23-acetate ( 5), Alisol F ( 6), and Alisol F 24-acetate ( 7).
METHODS AND RESULTS:
Based on 1D and 2D-NMR data (HMQC, HMBC, COSY, ROESY), the structure of the new compound was deduced to be 11-dehydroxy-12-dehydroAlisol F-24-acetate ( 1). Compounds 2 - 7 exhibited inhibitory activity in vitro on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line with IC (50) values of 2.3, 11.0, 15.4, 14.3, 0.6 and 7.7 microM, and on HBV e antigen (HBeAg) secretion with IC (50) values of 498.1, 17.6, 41.0, 19.9, 8.5 and 5.1 microM, respectively.

Molecules. 2017 Jun 8;22(6).

Anti-Inflammatory Activities and Liver Protection of Alisol F and 25-Anhydroalisol F through the Inhibition of MAPK, STAT3, and NF-κB Activation In Vitro and In Vivo.[Pubmed: 28594379 ]

Alisol F and 25-anhydroAlisol F isolated from Alisma orientale, were proved to exhibit anti-inflammatory potential in our previous work.
METHODS AND RESULTS:
In the current study, the anti-inflammatory effects and action mechanisms of Alisol F and 25-anhydroAlisol F were investigated in vitro. Moreover, the pharmacological effects of Alisol F in lipopolysaccharide (LPS)/d-galactosamine (d-gal)-induced acute liver-injured mice were evaluated. The results demonstrated that Alisol F and 25-anhydroAlisol F could suppress LPS-induced production of nitric oxide (NO), interleukin-6 (IL-6), tumor necrosis factor alpha (TNF-α), and interleukin-1β (IL-1β), as well as inhibit the mRNA and protein levels of inducible nitric oxide (iNOS) and cyclooxygenase-2 (COX-2). In addition, we investigated the role of Alisol F and 25-anhydroAlisol F in mediating mitogen-activated protein kinases (MAPKs), signal transducers, and activators of transcription 3 (STAT3) and nuclear factor κB (NF-κB) pathways involved in the inflammation process of LPS-stimulated RAW 264.7 cells. The phosphorylation of ERK, JNK, p38, and STAT3, and the NF-κB signaling pathway, were obviously suppressed in Alisol F and 25-anhydroAlisol F treated cells. Results obtained from in vitro experiments suggested Alisol F obviously improved liver pathological injury by inhibiting the production of TNF-α, IL-1β, and IL-6, and significantly decreasing the serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels in LPS/d-gal-induced mice. Furthermore, the reduction of phosphorylation of ERK and JNK, as well as suppression of the NF-κB signaling pathway, were also observed in liver tissues of the Alisol F-treated mice model.
CONCLUSIONS:
Alisol F and 25-anhydroAlisol F may serve as potential leads for development of anti-inflammatory agents for acute liver failure treatment.

Phytochemistry. 2016 Nov;131:150-157.

Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale.[Pubmed: 27615692]

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.
METHODS AND RESULTS:
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.