Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacephenone derivatives from Artemisia capillaris

Yong Zhao; CA Geng; H Chen; YB Ma; XY Huang; TW Cao; K He; H Wang; XM Zhang; JJ Chen

doi:10.1016/j.bmcl.2015.02.024

Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacephenone derivatives from Artemisia capillaris

Yong Zhao, CA Geng, H Chen, YB Ma, XY Huang, TW Cao, K He, H Wang, XM Zhang, JJ Chen

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

31 Citationer (Scopus)

Abstract

p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.

Originalsprog	Engelsk
Tidsskrift	Biooganic & Medicinal Chemistry Letters
Vol/bind	25
Sider (fra-til)	1509-1514
DOI	https://doi.org/10.1016/j.bmcl.2015.02.024
Status	Udgivet - 2015
Udgivet eksternt	Ja

Adgang til dokumentet

10.1016/j.bmcl.2015.02.024

Citationsformater

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title = "Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacephenone derivatives from Artemisia capillaris",

abstract = "p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.",

author = "Yong Zhao and CA Geng and H Chen and YB Ma and XY Huang and TW Cao and K He and H Wang and XM Zhang and JJ Chen",

year = "2015",

doi = "10.1016/j.bmcl.2015.02.024",

language = "English",

volume = "25",

pages = "1509--1514",

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T1 - Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacephenone derivatives from Artemisia capillaris

AU - Zhao, Yong

AU - Geng, CA

AU - Chen, H

AU - Ma, YB

AU - Huang, XY

AU - Cao, TW

AU - He, K

AU - Wang, H

AU - Zhang, XM

AU - Chen, JJ

PY - 2015

Y1 - 2015

N2 - p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.

AB - p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.

U2 - 10.1016/j.bmcl.2015.02.024

DO - 10.1016/j.bmcl.2015.02.024

M3 - Journal article

VL - 25

SP - 1509

EP - 1514

JO - Biooganic & Medicinal Chemistry Letters

JF - Biooganic & Medicinal Chemistry Letters

ER -