Secoiridoid glucosides and unusual recyclized secoiridoid aglycones from Ligustrum vulgare

被引:15
作者
Tanahashi, Takao [1 ]
Takenaka, Yukiko [1 ]
Okazaki, Naoaki [1 ]
Koge, Megumi [1 ]
Nagakura, Naotaka [1 ]
Nishi, Toyoyuki [2 ]
机构
[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan
[2] Nippon Shinyaku Inst Bot Res, Yamashina Ku, Kyoto 6078182, Japan
关键词
Ligustrum vulgare; Oleaceae; Secoiridoid glucoside; Secoiridoid; 10-Hydroxy-2 ''-methoxyoleuropein; Ligustrohemiacetal; 10-Hydroxyoleoside aglycone; JASMINUM; CONSTITUENTS;
D O I
10.1016/j.phytochem.2009.09.009
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
Phytochemical investigation of the dried leaves and twigs of Ligustrum vulgare has led to the isolation of the secoiridoid glucosides, (2 '' R)- and (2 '' S)-10-hydroxy-2 ''-methoxyoleuropeins (1 and 2), and the secoiridoid aglycones, ligustrohemiacetals A (3) and B (4). Their structures were elucidated by spectroscopic and chemical means. Enzymatic hydrolysis of 10-hydroxyoleuropein to the analog of ligustrohemiacetals A and B led to the structural revision of jasmolactones. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2072 / 2077
页数:6
相关论文
共 15 条
[1]   SECOIRIDOID GLUCOSIDES FROM LONICERA-PERICLYMENUM [J].
CALIS, I ;
STICHER, O .
PHYTOCHEMISTRY, 1984, 23 (11) :2539-2540
[2]   SECOIRIDOIDS FROM OLEA-EUROPAEA [J].
GARIBOLDI, P ;
JOMMI, G ;
VEROTTA, L .
PHYTOCHEMISTRY, 1986, 25 (04) :865-869
[3]   STUDIES ON MONOTERPENE GLUCOSIDES AND RELATED NATURAL-PRODUCTS .46. 3 SECOIRIDOID GLUCOSIDES FROM LIGUSTRUM-JAPONICUM [J].
INOUE, K ;
NISHIOKA, T ;
TANAHASHI, T ;
INOUYE, H .
PHYTOCHEMISTRY, 1982, 21 (09) :2305-2311
[4]   Dual inhibition of metallopeptidases ACE and NEP by extracts, and iridoids from Ligustrum vulgare L. [J].
Kiss, A. K. ;
Mank, M. ;
Melzig, M. F. .
JOURNAL OF ETHNOPHARMACOLOGY, 2008, 120 (02) :220-225
[5]   STUDIES ON THE CONSTITUENTS OF ACANTHOPANAX-SCIADOPHYLLOIDES FR ET SAV LEAVES [J].
KITAJIMA, J ;
TAKAMORI, Y ;
TANAKA, Y .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1989, 109 (03) :188-191
[6]   Carbohydrate esters of cinnamic acid from fruits of Physalis peruviana, Psidium guajava']java and Vaccinium vitis-idaea [J].
Latza, S ;
Gansser, D ;
Berger, RG .
PHYTOCHEMISTRY, 1996, 43 (02) :481-485
[7]   HPLC analysis of flavonoids and secoiridoids in leaves of Ligustrum vulgare L. (Oleaceae) [J].
Romani, A ;
Pinelli, P ;
Mulinacci, N ;
Vincieri, FF ;
Gravano, E ;
Tattini, M .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (09) :4091-4096
[8]   SECOIRIDOID GLYCOSIDES FROM JASMINUM-MULTIFLORUM [J].
SHEN, YC ;
LIN, CY ;
CHEN, CH .
PHYTOCHEMISTRY, 1990, 29 (09) :2905-2912
[9]   NOVEL SECOIRIDOID LACTONES FROM JASMINUM-MULTIFLORUM [J].
SHEN, YC ;
CHEN, CH .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05) :1060-1070
[10]  
SHEN YC, 1993, TETRAHEDRON LETT, V34, P1949