Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities

被引：40
|
作者：
Bi, Xueyan [1 ,2 ]
Li, Wei [1 ]
Sasaki, Tatsunori [1 ]
Li, Qin [3 ]
Mitsuhata, Naoko [1 ]
Asada, Yoshihisa [4 ]
Zhang, Qingbo [2 ]
Koike, Kazuo [1 ]
机构：
[1] Toho Univ, Fac Pharmaceut Sci, Chiba 2748510, Japan
[2] Heilongjang Inst Food & Drug Control, Harbin 150001, Peoples R China
[3] China Med Univ, Affiliated Hosp 4, Lab Ctr, Shenyang 110005, Peoples R China
[4] Tokyo Univ Sci, Fac Pharmaceut Sci, Chiba 2788510, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 21期
关键词：
Syringa reticulata; Antioxidant; Oleaceae; Secoiridoid; Superoxide anion scavenging activity; PHENOLIC GLYCOSIDES; CONSTITUENTS; DERIVATIVES; LIGNAN;
D O I：
10.1016/j.bmcl.2011.08.089
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A 70% EtOH extract from the bark of Syringa reticulata has shown significant antioxidant activity. Chemical study on the extract resulted in the isolation of seventeen compounds (1-17), including a novel oleoside-type secoiridoid glucoside, reticuloside (1), and the structures were elucidated on the basis of extensive spectroscopic analyses. Among the isolated compounds, jaspolyoside (2), oleuropein (4) and 2-(3,4-dihydroxy)-phenylethyl-beta-D-glucopyranoside (17), showed the most potent superoxide anion scavenging activity with the EC50 values of 4.97, 2.57 and 4.97 mu M, respectively. The structure-activity relationship indicated that the presence of 2-(3,4-dihydroxyphenyl)-ethoxy group is important for exhibiting the activity. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6426 / 6429
页数：4
相关论文
共 50 条
  • [41] Diterpenoid, sesquiterpenoid and secoiridoid glucosides from Aster auriculatus
    Wang, CZ
    Yu, DQ
    [J]. PHYTOCHEMISTRY, 1997, 45 (07) : 1483 - 1487
  • [42] Secoiridoid and iridoid glucosides from the leaves of Fraxinus griffithii
    Macahig, Rene Angelo
    Harinantenaina, Liva
    Matsunami, Katsuyoshi
    Otsuka, Hideaki
    Takeda, Yoshio
    Shinzato, Takakazu
    [J]. JOURNAL OF NATURAL MEDICINES, 2010, 64 (01) : 1 - 8
  • [43] NEW SECOIRIDOID GLUCOSIDES FROM GENTIANA-VERNA
    MPONDO, EM
    GARCIA, J
    LESTANI, J
    [J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05): : 1146 - 1149
  • [44] Further acylated secoiridoid glucosides from Gentiana rhodantha
    Ma, WG
    Fuzzati, N
    Wolfender, JL
    Yang, CR
    Hostettmann, K
    [J]. PHYTOCHEMISTRY, 1996, 43 (04) : 805 - 810
  • [45] IRIDOID AND SECOIRIDOID GLUCOSIDES FROM GENTIANA-OLIVIERI
    ERSOZ, T
    CHULIA, AJ
    GARCIA, J
    CALIS, I
    [J]. PHARMACEUTISCH WEEKBLAD-SCIENTIFIC EDITION, 1987, 9 (04) : 233 - 233
  • [46] Two novel secoiridoid glucosides from Tripterospermum chinense
    Zhang, Tao
    Li, Jian
    Li, Bin
    Chen, Li
    Yin, Hai-Long
    Liu, Shi-Jun
    Tian, Ying
    Dong, Jun-Xing
    [J]. JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2012, 14 (12) : 1097 - 1102
  • [47] Two new phenolic glycosides from Syringa reticulata
    Koichi Machida
    Naomi Ohkawa
    Asami Ohsawa
    Masao Kikuchi
    [J]. Journal of Natural Medicines, 2009, 63
  • [48] Two dimeric secoiridoid glucosides from Jasminum polyanthum
    Tanahashi, T
    Takenaka, Y
    Nagakura, N
    [J]. PHYTOCHEMISTRY, 1996, 41 (05) : 1341 - 1345
  • [49] Secoiridoid and iridoid glucosides from the leaves of Fraxinus griffithii
    Rene Angelo Macahig
    Liva Harinantenaina
    Katsuyoshi Matsunami
    Hideaki Otsuka
    Yoshio Takeda
    Takakazu Shinzato
    [J]. Journal of Natural Medicines, 2010, 64 : 1 - 8
  • [50] Nine new secoiridoid glucosides from jasminum nudiflorum
    Takenaka, Y
    Tanahashi, T
    Taguchi, H
    Nagakura, N
    Nishi, T
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (03) : 384 - 389
12345