Inhibitory effects of compounds from Styrax obassia on NO production

Thao Quyen Cao; Manh Hung Tran; Jeong Ah Kim; Phuong Thao Tran; Jeong-Hyung Lee; Mi Hee Woo; Hyeong-Kyu Lee; Byung Sun Min

doi:10.1016/j.bmcl.2015.10.020

Inhibitory effects of compounds from Styrax obassia on NO production

Bioorg Med Chem Lett. 2015 Nov 15;25(22):5087-91. doi: 10.1016/j.bmcl.2015.10.020. Epub 2015 Oct 8.

Authors

Thao Quyen Cao¹, Manh Hung Tran¹, Jeong Ah Kim², Phuong Thao Tran³, Jeong-Hyung Lee⁴, Mi Hee Woo¹, Hyeong-Kyu Lee⁵, Byung Sun Min⁶

Affiliations

¹ College of Pharmacy, Drug Research and Development Center, Catholic University of Daegu, Gyeongbuk 712-702, Republic of Korea.
² College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 702-701, Republic of Korea.
³ College of Natural Science, Kangwon National University, Kangwon 200-701, Republic of Korea.
⁴ College of Natural Science, Kangwon National University, Kangwon 200-701, Republic of Korea. Electronic address: jhlee36@kangwon.ac.kr.
⁵ Natural Medicine Research Center, Korea Research Institute of Bioscience & Biotechnology, Chungbuk 363-883, Republic of Korea.
⁶ College of Pharmacy, Drug Research and Development Center, Catholic University of Daegu, Gyeongbuk 712-702, Republic of Korea. Electronic address: bsmin@cu.ac.kr.

PMID: 26483135
DOI: 10.1016/j.bmcl.2015.10.020

Abstract

Two new benzofurans, 2-(3,4-dimethoxyphenyl)-5-(1,3-dihydroxypropyl)-7-methoxybenzofuran (1) and 2-(3,4-methylenedioxyphenyl)-5-(3-hydroxymethyletoxy-1-hydroxypropyl)-7-methoxybenzofuran (2), a new triterpene, 3β, 6β, 21β-trihydroxyolean-12-ene (3), and eleven known compounds were isolated from the stem bark of Styrax obassia. The structures of the isolated compounds were established by extensive spectroscopic analyses, including 1D and 2D NMR and HRMS. Their anti-inflammatory activities were evaluated against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. Compound 1 was shown to reduce LPS-induced iNOS expression in a dose-dependent manner. In addition, pretreating cells with 1 significantly suppressed their LPS-induced expression of COX-2 protein.

Keywords: Benzofuran; NO production; RAW246.7 cells; Styracaceae; Styrax obassia.

Publication types

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

MeSH terms

Animals
Anisoles / isolation & purification
Anisoles / pharmacology
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Benzofurans / isolation & purification
Benzofurans / pharmacology*
Cell Line
Cyclooxygenase 2 / metabolism
Cyclooxygenase 2 Inhibitors / isolation & purification
Cyclooxygenase 2 Inhibitors / pharmacology
Mice
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide / biosynthesis
Nitric Oxide Synthase Type II / antagonists & inhibitors
Plant Bark / chemistry
Styrax / chemistry*
Triterpenes / isolation & purification
Triterpenes / pharmacology

Substances

2-(3,4-dimethoxyphenyl)-5-(3-methoxypropyl)benzofuran
Anisoles
Anti-Inflammatory Agents, Non-Steroidal
Benzofurans
Cyclooxygenase 2 Inhibitors
Triterpenes
homoegonol
Nitric Oxide
Nitric Oxide Synthase Type II
Nos2 protein, mouse
Ptgs2 protein, mouse
Cyclooxygenase 2