Quiquelignan A-H, eight new lignoids from the rattan palm Calamus quiquesetinervius and their antiradical, anti-inflammatory and antiplatelet aggregation activities

Chao-Lin Chang; Li-Jie Zhang; Ru-Yin Chen; Chin-Chung Wu; Hui-Chi Huang; Michael C Roy; Jhih-Ping Huang; Yang-Chang Wu; Yao-Haur Kuo

doi:10.1016/j.bmc.2009.12.016

Quiquelignan A-H, eight new lignoids from the rattan palm Calamus quiquesetinervius and their antiradical, anti-inflammatory and antiplatelet aggregation activities

Bioorg Med Chem. 2010 Jan 15;18(2):518-25. doi: 10.1016/j.bmc.2009.12.016. Epub 2009 Dec 11.

Authors

Chao-Lin Chang¹, Li-Jie Zhang, Ru-Yin Chen, Chin-Chung Wu, Hui-Chi Huang, Michael C Roy, Jhih-Ping Huang, Yang-Chang Wu, Yao-Haur Kuo

Affiliation

¹ Graduate Institute of Natural Products, Kaohsiung Medical University 807, Taiwan, ROC.

PMID: 20056545
DOI: 10.1016/j.bmc.2009.12.016

Abstract

Eight new lignin derivatives, termed quiquelignan A-H (1-8), comprising three tricin-type flavonolignans (1-3) and five 8-O-4' neolignans (4-8), were isolated from the ethanol extract of Calamus quiquesetinervius stems. Structural elucidation of the new isolates was accomplished on the basis of spectroscopic data. Compounds 1-8 showed strong-to-moderate antioxidant activity against the hydroxy radical (()OH). Among them, compound 5 showed significantly higher hydroxy radical scavenging activity (IC(50) 4.4microg/mL). Compounds 2-4 and 6-8 dose-dependently suppressed the LPS-stimulated production of nitric oxide (NO) in RAW 264.7 cells. The anti-inflammatory potency of 4 and 6 was 2.7-4.5-fold higher compared with quercetin. Compounds 2-4, 6 and 8 also exhibited mild collagen-antagonistic activity, but were inactive with respect to thrombin-induced platelet aggregation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Antioxidants / chemistry
Antioxidants / isolation & purification
Antioxidants / pharmacology*
Calamus / chemistry*
Cell Survival / drug effects
Dose-Response Relationship, Drug
Free Radical Scavengers / chemistry
Free Radical Scavengers / isolation & purification
Free Radical Scavengers / pharmacology*
Lignin / analogs & derivatives
Lignin / isolation & purification
Lignin / pharmacology*
Mice
Molecular Structure
Plant Stems / chemistry
Platelet Aggregation / drug effects
Platelet Aggregation Inhibitors / chemistry
Platelet Aggregation Inhibitors / isolation & purification
Platelet Aggregation Inhibitors / pharmacology*
Stereoisomerism
Structure-Activity Relationship

Substances

Anti-Inflammatory Agents
Antioxidants
Free Radical Scavengers
Platelet Aggregation Inhibitors
Lignin