Anti-HBV active constituents from Piper longum

In the screening search for Hepatitis B virus inhibitory agents from medicinal plants, the ethanol extract of Piper longum Linn. was found to possess superior anti-HBV activity in vitro. Bioassay-guided fractionation coupled with repeated purification resulted in the isolation of four new compounds,...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2013-04, Vol.23 (7), p.2123-2127
Main Authors: Jiang, Zhi-Yong, Liu, Wen-Feng, Zhang, Xue-Mei, Luo, Jie, Ma, Yun-Bao, Chen, Ji-Jun
Format: Article
Language:English
Subjects:
alkaloids
Amide alkaloids
Anti-HBV activity
Antiviral Agents - chemistry
Antiviral Agents - isolation & purification
Antiviral Agents - pharmacology
chemistry
Dose-Response Relationship, Drug
ethanol
fractionation
glycosides
Hep G2 Cells
hepatitis B antigens
Hepatitis B virus
Hepatitis B virus - drug effects
Humans
Longumoside
medicinal plants
Microbial Sensitivity Tests
Molecular Structure
nuclear magnetic resonance spectroscopy
Piper - chemistry
Piper longum
Plant Extracts - chemistry
Plant Extracts - isolation & purification
Plant Extracts - pharmacology
screening
secretion
Structure-Activity Relationship
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Summary:In the screening search for Hepatitis B virus inhibitory agents from medicinal plants, the ethanol extract of Piper longum Linn. was found to possess superior anti-HBV activity in vitro. Bioassay-guided fractionation coupled with repeated purification resulted in the isolation of four new compounds, involving two new glycosides longumosides A (1) and B (2) and two new amide alkaloids erythro-1-[1-oxo-9(3,4-methylenedioxyphenyl)-8,9-dihydroxy-2E-nonenyl]-piperidine (3), threo-1-[1-oxo-9(3,4-methylenedioxyphenyl)-8,9-dihydroxy-2E-nonenyl]-piperidine (4), as well as two compounds 3β,4α-dihydroxy-2-piperidinone (5), 5,6-dihydro-2(1H)-pyridinone (6) from natural source for the first time. The structures of the four new compounds were determined by extensive analyses of the MS, IR, 1D and 2D NMR data. Besides, the compounds 2–6, together with the known compounds 7–11 obtained previously, were assayed for their anti-HBV activity by using Hep G 2.2.15 cell line in vitro. Results suggested the compound piperine (7) possessed remarkable inhibitory HBV activity, against the secretion of hepatitis B virus surface antigen (HBsAg) and hepatitis B virus e antigen (HBeAg) with the Selectivity Index (SI) values of 15.7 and 16.8, respectively.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.01.118