Neolignan and megastigmane glucosides from the aerial parts of Isodon japonicus with cell protective effects on BaP-induced cytotoxicity

被引:22
作者
Matsumoto, Takahiro [1 ]
Nakamura, Seikou [1 ]
Nakashima, Souichi [1 ]
Ohta, Tomoe [1 ]
Ogawa, Keiko [1 ]
Fukaya, Masashi [1 ]
Tsukioka, Junko [1 ]
Hasei, Tomohiro [1 ]
Watanabe, Tetsushi [1 ]
Matsuda, Hisashi [1 ]
机构
[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan
关键词
Isodon japonicas; Lamiaceae; Isodonoside; Isodonmegastigmane; Glucoside; Neolignan; Megastigmane; FLOWER BUDS; GLYCOSIDES; LIGNAN; LEAVES; MELANOGENESIS; CONSTITUENTS; ROOTS; ACID;
D O I
10.1016/j.phytochem.2017.02.007
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Six neolignan glucosides, named isodonosides I-VI, and a megastigmane glucoside named isodonmegastigmane I, were isolated together with 15 known compounds from the methanolic extract of aerial parts of Isodon japonicus cultivated in Tokushima, Japan. The chemical structures of the compounds were elucidated based on their MS and NMR spectroscopic analysis. The absolute configurations of the neolignan and megastigmane glucosides were determined by derivatizations, by ECD (electronic circular dicroism) Cotton effect approximation, and by the modified Mosher's method. In addition, a significant cell protective effects of neolignan glucosides on benzolajpyrene-induced cytotoxicity was found. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:101 / 108
页数:8
相关论文
共 39 条
[1]   TANNINS IN LABIATAE PLANTS .2. A TETRAMERIC DERIVATIVE OF CAFFEIC ACID FROM RABDOSIA-JAPONICA [J].
AGATA, I ;
HATANO, T ;
NISHIBE, S ;
OKUDA, T .
PHYTOCHEMISTRY, 1989, 28 (09) :2447-2450
[2]   ASYMMETRIC-SYNTHESIS OF "3-METHYL-2-PHENYL-1,4-BENZODIOXANES - ABSOLUTE-CONFIGURATION OF THE NEOLIGNANS EUSIDERIN AND EUSIDERIN-C AND EUSIDERIN-D [J].
ARNOLDI, A ;
MERLINI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2555-2557
[3]   CELL-DIVISION PROMOTING ACTIVITY OF NATURALLY-OCCURRING DEHYDRODICONIFERYL GLUCOSIDES - DO CELL-WALL COMPONENTS CONTROL CELL-DIVISION [J].
BINNS, AN ;
CHEN, RH ;
WOOD, HN ;
LYNN, DG .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (04) :980-984
[4]   (6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits [J].
Çalis, I ;
Kuruüzüm-Uz, A ;
Lorenzetto, PA ;
Rüedi, P .
PHYTOCHEMISTRY, 2002, 59 (04) :451-457
[5]   Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui [J].
D'Abrosca, B ;
DellaGreca, M ;
Fiorentino, A ;
Monaco, P ;
Oriano, P ;
Temussi, F .
PHYTOCHEMISTRY, 2004, 65 (04) :497-505
[6]   Iridoid glucosides from Veronica hederifolia [J].
Harput, US ;
Saracoglu, I ;
Nagatsu, A ;
Ogihara, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (08) :1106-1108
[7]  
HECHT SS, 1993, J CELL BIOCHEM, P27
[8]   A new furofuran lignan from Isodon japonicus [J].
Hong, Seong Su ;
Lee, Chul ;
Lee, Chang Hee ;
Park, Mieon ;
Lee, Moon Soon ;
Hong, Jin Tae ;
Lee, Heesoon ;
Lee, Mi Kyeong ;
Hwang, Bang Yeon .
ARCHIVES OF PHARMACAL RESEARCH, 2009, 32 (04) :501-504
[9]   Two New Diterpenoids and Other Constituents from Isodon japonicus [J].
Hou, Rui-Jie ;
Yan, Fu-Lin ;
Zhang, Hai-Yang ;
Bai, Yi-Xiao ;
Ding, Ming-Ming .
HELVETICA CHIMICA ACTA, 2012, 95 (07) :1175-1180
[10]   Neolignan glycosides from Symplocos caudata [J].
Huo, Changhong ;
Liang, Hong ;
Zhao, Yuying ;
Wang, Bin ;
Zhang, Qingying .
PHYTOCHEMISTRY, 2008, 69 (03) :788-795