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New Lignans from the Flower of Forsythia koreana and Their Suppression Effect on VCAM ‐1 Expression in MOVAS Cells
Author(s) -
Lee YeongGeun,
Jang SeonA,
Seo KyeongHwa,
Gwag Jung Eun,
Kim HyoungGeun,
Ko JungHwan,
Ji SoAe,
Kang SeChan,
Lee Dae Young,
Baek NamIn
Publication year - 2018
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201800026
Subject(s) - pinoresinol , chemistry , lignan , forsythia , caprifoliaceae , sephadex , column chromatography , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , silica gel , chromatography , organic chemistry , botany , enzyme , honeysuckle , medicine , alternative medicine , traditional chinese medicine , pathology , biology
Six lignans including two new lignans were obtained as the principal components of the Forsythia koreana flowers via silica gel (SiO 2 ), octadecyl SiO 2 ( ODS ) as well as Sephadex LH ‐20 column chromatography. In addition to two new lignans, named koreanaside A ((7 R ,8 S ,7 ′R ,8 ′S )‐7,7 ′ ‐diepoxy‐5 ′ ‐hydroxy‐3,3 ′ ‐dimethoxylignan 4‐ O ‐ β ‐ d ‐glucopyranoside) and koreanaside B ((7 R ,8 S ,7 ′S ,8 ′R )‐7,9 ′ ‐epoxy‐9,5 ′ ,7 ′ ‐trihydroxy‐3,3 ′ ‐dimethoxylignan 4‐ O ‐ β ‐ d ‐glucopyranoside), four known lignans were identified to be (+)‐phylligenin, (−)‐epipinoresinol, pinoresinol, and tinosposide A. The structures and absolute configurations of koreanasides A and B were established by means of analysis of spectroscopic data ( NMR , IR , FAB ‐ MS , and CD ), whereas the structures of known lignans were identified by comparison their NMR and MS values with those in the reported literature. Their chemical structures including configuration were established by means of analysis of spectroscopic data ( NMR , IR , FAB ‐ MS , and CD ) but also comparison of their NMR and MS values with those in the reported literature. This is the first article for isolation of six lignans of F . koreana flowers. Koreanasides A and B showed high radical scavenging activity with oxygen radical absorbance capacity ( ORAC ) values of 0.97 ± 0.01 and 1.02 ± 0.01, respectively. Koreanaside A also prohibited expressing VCAM ‐1 in MOVAS cells with 80.5% at 25 mg/mL.