A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.

被引:19
作者
Li, Chuangjun [1 ,2 ]
Li, Li [1 ,2 ]
Wang, Chao [1 ,2 ]
Yang, Jingzhi [1 ,2 ]
Ye, Fei [1 ,2 ]
Tian, Jinying [1 ,2 ]
Si, Yikang [1 ,2 ]
Zhang, Dongming [1 ,2 ]
机构
[1] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[2] Peking Union Med Coll, Beijing 100050, Peoples R China
关键词
Eucommia ulmoides Oliv; nor-triterpenoid; ulmoidol A; absolute configuration; ECD; PTPIB; MEGASTIGMANE GLYCOSIDES; CONSTITUENTS; SESQUILIGNAN; BARK;
D O I
10.3390/molecules171213960
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
A new ursane-type nortriterpenoid, (11S,12S)-4-methyl-11,12-epoxy-2-hydroxy-3-oxoursa-1,4-dine-28-oic acid gamma-lactone (1), named ulmoidol A, together with ten known compounds: ulmoidol (2), corosolic acid (3), 2 alpha,3 alpha-dihydroxy-24-nor-4(23), 12-oleanadien-28-oic acid (4), oleanolic acid (5), ursolic acid (6), cycloart-3 beta, 25-diol (7), foliasalacioside B1 (8), (6R,7E,9R)-9-hydroxy-4,7-megastigmadien-3-one-9-O-alpha-L-arabinopyranosyl-(1 -> 6)-beta-D-glucopyranoside (9), (6R,7E,9R)-9-hydroxy-4,7-megastigma-dien-3-one-9-O-alpha-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside (10), and quercetin 3-O-sambubioside (11) were isolated from the leaves of Eucommia ulmoides Oliv. The structure of compound 1 was determined by extensive spectroscopic analysis, and its absolute configuration was determined by CD experiments and a computational method. Compounds 3, 4, 7-10 were isolated from this plant for the first time. Compounds 3 and 4 showed inhibition to PTPIB activities, with IC50 values of 0.69 and 3.98 mu M, respectively.
引用
收藏
页码:13960 / 13968
页数:9
相关论文
共 25 条
[21]   Studies on the chemical constituents of green leaves of Eucommia ulmoides Oliv. [J].
Takamura, Chika ;
Hirata, Tetsuya ;
Yamaguchi, Yasuyo ;
Ono, Masateru ;
Miyashita, Hiroyuki ;
Ikeda, Tsuyoshi ;
Nohara, Toshihiro .
JOURNAL OF NATURAL MEDICINES, 2007, 61 (02) :220-221
[22]  
Tanaka C, 1997, CHEM PHARM BULL, V45, P1379, DOI 10.1248/cpb.45.1379
[23]   Production of bioactive triterpenes by Eriobotrya japonica calli [J].
Taniguchi, S ;
Imayoshi, Y ;
Kobayashi, E ;
Takamatsu, Y ;
Ito, H ;
Hatano, T ;
Sakagami, H ;
Tokuda, H ;
Nishino, H ;
Sugita, D ;
Shimura, S ;
Yoshida, T .
PHYTOCHEMISTRY, 2002, 59 (03) :315-323
[24]   Adenanthusone, a new ursane type nortriterpenoid from Isodon adenanthus [J].
Xiang, W ;
Song, QS ;
Zhang, HJ ;
Li, RT ;
Na, Z ;
Sun, HD .
HELVETICA CHIMICA ACTA, 2004, 87 (11) :2842-2847
[25]   A new phenolic glucoside and flavonoids from the bark of Eucommia ulmoides Oliv. [J].
Yao, Li-Na ;
Su, Yan-Fang ;
Yin, Zhao-Ye ;
Qin, Nan ;
Li, Tian-Xiang ;
Si, Chuan-Ling ;
Liu, Er-Wei ;
Gao, Xiu-Mei .
HOLZFORSCHUNG, 2010, 64 (05) :571-575