A New Triterpene and Anti-Hepatitis B Virus Active Compounds from <i>Alisma orientalis</i>

Jiang, Zhi‐Yong; Zhang, Xuemei; Zhang, Fengxue; Liu, Geoffrey; Zhao, Fang; Zhou, Jun; Chen, Ji‐Jun

doi:10.1055/s-2006-947178

Cited by 105 publications

(61 citation statements)

References 5 publications

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“…Protostane triterpenes from Alisma orientalis have also been reported for their anti-HBV activity. Compound 7 in particular showed promising effects, inhibiting HBsAg and HBeAg with an IC50 of 7.7 µmol/L and 5.1 µmol/L, respectively, whereas cytotoxicity was only observed at a much higher concentration [50% cytotoxicity concentration (CC50)=142.7 µmol/L] [39] . Among the 10 different alkaloids isolated from Corydalis saxicola, a traditional herb used as folk medicine to treat hepatitis in China, dihydrochelerythrine was shown to exhibit extraordinary effects against HBsAg and HBeAg secretions.…”

Section: -Arylbenzofuran Derivativesmentioning

confidence: 99%

Natural products as promising drug candidates for the treatment of hepatitis B and C

Wohlfarth

Efferth

2008

Acta Pharmacol Sin

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Hepatitis B virus (HBV) or hepatitis C virus (HCV) infections are a major threat worldwide. Combination therapy of interferon-α and ribavirin is currently the treatment of choice for HCV-infected patients. However, this regimen is only effective in approximately 50% of patients and provokes severe side-effects. Numerous natural alternatives for treating HCV have been suggested. Deoxynojirimycin and its derivatives are iminosugars which exert anti-HCV activity by inhibiting α-glucosidases. A non-immunosuppressive derivate of cyclosporine A, NIM811, exerts anti-HCV activity by binding to cyclophilin. Other natural products with promising anti-HCV activity are 2-arylbenzofuran derivatives, Mellein, and pseudoguaianolides. For HBV treatment, several drugs are available, specifically targeting the virus polymerase (lamivudine, entecavir, telbivudine, and adefovir dipivoxil). The efficacy of these drugs is hampered by the development of resistance due to point mutations in the HBV polymerase. Due to drug resistance and adverse side-effects, the search for novel drugs is mandatory. Wogonin, ellagic acid, artemisinin and artesunate, chrysophanol 8-O-β-D-glucoside, saikosaponin C, and protostane triterpenes are active against HBV. Natural products need to be investigated in more detail to explore their potential as novel adjuncts to established HBV or HCV therapy.

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Section: -Arylbenzofuran Derivativesmentioning

confidence: 99%

Natural products as promising drug candidates for the treatment of hepatitis B and C

Wohlfarth

Efferth

2008

Acta Pharmacol Sin

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“…The 1 H-and 13 C-NMR spectra (Table 1) showed signals for one oxymethine, one oxygen quaternary carbon, five tertiary methyls, and a 1,2,4-trisubstituted aromatic ring, which suggested that compound 1 was an abietane diterpenoid substituted by two hydroxy groups. The heteronuclear multiple bond connectivity (HMBC) correlations of H-C (16) and H-C(17) (d H 1.58, 2H 3 ) with the oxygen quaternary carbon C(15) (d C 72.3, s) confirmed that one hydroxy group was located at C (15). Furthermore, correlations H-C(3)/C(1), C (2) and C(4), and H-C(5)/C(3) in the HMBC spectrum of 1 confirmed the other hydroxy group to be positioned at C(3).…”

Section: Resultsmentioning

confidence: 99%

“…The formazan crystals were redissolved and the absorbance was measured on a microplate reader at 490 nm. 16) Cytotoxicity Testing Cells were seeded in 96-well plates, treated with indicated concentrations of tested compounds or a positive control compound, Etoposide (VP-16; Jiangsu Hengrui Medicine Co., Ltd.). After incubation for 24 h at 37°C, 20 ml/well of MTT (5 mg/ml) was added and cells were incubated for an additional 4 h. Then, "triplex solution" (10% sodium dodecyl sulfate (SDS), 5% isobutanol, 12 mM HCl) was added to dissolve the formazan crystals overnight.…”

Section: Methodsmentioning

confidence: 99%

Anti-Hepatitis B Virus and Cytotoxic Diterpenoids from Isodon lophanthoides var. gerardianus

Yang

Li²,

Huang

et al. 2011

Chem. Pharm. Bull.

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“…is widely cultivated in China and Japan, and the dried rhizomes are a crude drug for the treatment of diabetes and diuretics. 1) Our previous paper 2) reported that a serious protostane-type triterpenes extracted from this plant showed anti-hepatitis B virus (HBV) activity. As a subsequent study on this plant, further investigation on the less polar part of the 90% EtOH extract of the dried rhizomes of A. orientalis led to the isolation of two new sesquiterpenes: alismorientols A (1) and B (2) (Fig.…”

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Two New Sesquiterpenes from Alisma orientalis

Jiang

Zhang

Zhou

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Alisma orientalis (SAM.) JUZEP. is widely cultivated in China and Japan, and the dried rhizomes are a crude drug for the treatment of diabetes and diuretics. 1) Our previous paper 2) reported that a serious protostane-type triterpenes extracted from this plant showed anti-hepatitis B virus (HBV) activity. As a subsequent study on this plant, further investigation on the less polar part of the 90% EtOH extract of the dried rhizomes of A. orientalis led to the isolation of two new sesquiterpenes: alismorientols A (1) and B (2) (Fig. 1 (Table 1). NMR spectral analysis revealed that compound 1 was a guaiane-type sesquiterpenoid. 13C DEPT experiment showed that compound 1 possessed the same numbers of methyls, methylenes, methines, and quaternary carbons as those of orientaol E.3) However, the chemical shifts for the C-atoms of 1 were not identical with those of orientaol E, 3) especially for C-4 (d 83.3), C-5 (52.0), C-7 (d 76.5), C-9 (37.6), C-10 (d 71.7), and C-14 (d 32.8). The chemical shifts for other C-atoms in 1 were also shifted downfield about 1 to 2 ppm. Considering the different solvent, the down-shift chemical shifts of those carbons could be explained.The differences between compound 1 and orientaol E are focused on C-4, 5, 7, 9, 10, and C-14. ESI-MS established that compound 1 had mass 18 units more than orientalol E, accounting for one molecule of H 2 O was added to the epoxyl of C-10 and C-7 of orientalol E to form compound 1, deducing one additional OH group presented in compound 1, which could be supported by the HMBC experiment. In the HMBC spectrum (Fig. 2), no correlation between H-14 and C-7 could be found, demonstrating no epoxy attached between C-7 and C-10. The other long-range correlations between protons and carbons in HMBC were also given as follows: H-14 and H-5 with C-1, H-5, H-3, and H-15 with C-4, H-5 with C-6, H-6, H-11, H-12, H-13 with C-7, C-11, H-6 with C-11, H-12, and H-13 with C-11. The relative stereostructure of 1 characterized by ROESY experiment accounted for the very different chemical shifts of C-4, 5, 9, and C-14. As shown in Fig. 2, correlations between H-1, assumed to be a-oriented, and H-5, Me-14 were observed, besides correlation between H-5 and H-6, suggesting that H-5, 6, and Me-14 were in a-orientation. The a-configuration for H-6 could also be concluded by the coupling constant of H-6 at d 4.51 (br s). Consequently, compound 1 was established as 4a,6b,7a,10b-tetrahydroxy-1,5-cis-guaiane (1), which was also confirmed by X-ray crystallographic analysis (Fig. 3).Compound 2 was obtained as a colorless prism. The IR spectrum of 2 exhibited absorptions for OH groups at 3406 cm Ϫ1 and an olefinic moiety at 1634 cm Ϫ1 . The molecular formula was deduced to be (Table 1), four tertiary methyl signals were observed, together with an olefinic proton at d H 5.87 (1H, d, Jϭ2.9 Hz, H-6). The 13 C-NMR spectrum of 2 revealed the presence of 15 carbon signals, of which two olefinic carbons [d C 121.6 (C-6, d), 150.0 (C-7, s)] were observed. The above spectral features suggested 2 ...

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A New Triterpene and Anti-Hepatitis B Virus Active Compounds from Alisma orientalis

Cited by 105 publications

References 5 publications

Natural products as promising drug candidates for the treatment of hepatitis B and C

Natural products as promising drug candidates for the treatment of hepatitis B and C

Anti-Hepatitis B Virus and Cytotoxic Diterpenoids from Isodon lophanthoides var. gerardianus

Two New Sesquiterpenes from Alisma orientalis

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