Furostanol saponins in Allium caepa L. var. tropeana seeds

被引:37
作者
Dini, I [1 ]
Tenore, GC [1 ]
Trimarco, E [1 ]
Dini, A [1 ]
机构
[1] Univ Naples Federico II, Fac Farm, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy
关键词
red onion; Allium caepa; Liliaceae; steroid saponins; NMR; mass;
D O I
10.1016/j.foodchem.2004.09.015
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An analysis of the polar extracts from seeds of Allium caepa L. var. tropeana led to the isolation of eight furostanol saponins, one of which was previously reported in the literature. On the basis of 1D, 2D NMR and mass spectrometry data, the structures of the compounds were elucidated as 1-O-beta-D-glucopyranosyl-(25R)-furost-5(6)-en-1 beta,3 beta,22 alpha,26-tetraol-26-O-alpha-L-rhamnopyranosyl-(1"' -> 2")-O-alpha-L-arabinopyranoside (1a), its epimer at position 22, 1-O-beta-D-glucopyranosyl-(25R)-furost-5(6)-en-1 beta,3 beta, 22 beta,26- tetraol-26-O-alpha-L-rhamnopyranosyl-(1"' -> 2")-O-alpha-L-arabinopyranoside (1b), 1-O-(3-D-glucopyranosyl-22-O-methyl-(25R)-furost-5(6)-en-1 beta,3 beta,22 zeta,26-tetraol-26-O-alpha-L-rhamnopyranosyl-(1"' -> 2")-O-alpha-L-arabinopyranoside (probably artefact) (2), 1-O-beta-D-glucopyranosyl-(25R)-furost-5(6)-en-1 beta,3 beta,22 beta,26-tetraol-26-O-alpha-L-rhamnopyranosyl-(1"' -> 6")-O-(3-D-galactopyranoside (3), 1-O-beta-D-glucopyranosyl-22-O-methyl-(25R)-furost-5(6)-en-1 beta,3 beta,22 zeta,26-tetraol-26-O-alpha-L-rhamnopyranosyl-(1"' -> 6")-O-beta-D-galactopyranoside (probably artefact) (4), 26-O-beta-D-glucopyranosyl-(25R)-furost-5(6)-en-3 beta,22 alpha,26-triol-3-O-alpha-L-rhamnopyranosyl-(1" -> 2')-O-[beta-D-glucopyranosyl-(1"' -> 6')-O]-beta-D-glucopyranoside (5a) and its epimer at position 22,26-O-beta-D-glucopyranosyl-(25R)-furost-5(6)-en-3 beta,22 beta,26-triol-3-O-alpha-L-rhamnopyranosyl-(1" -> 2')-O-[beta-D-glucopyranosyl-(1"' -> 6')-O]-beta-D-glucopyranoside (5b) and the known compound 26-O-beta-D-glucopyranosyl-22-O-methyl-(25R)-furost-5(6)-en-3 beta,22 zeta,26-triol-3-O-alpha-L-rhamnopyranosyl-(1" -> 2')-O-[beta-D-glucopyranosyl-(1"' -> 6')-O]-beta-D-glucopyranoside (6) [Mimaki, Y., Satou, T., Kuroda, M., Sashida, Y., & Hatakeyama, Y. (1999). Steroidal saponins from the bulbs of Lilium candidum. Phytochernistry, 51, 567-573]. This is the first report on furostanol saponins in the seeds of Allium caepa L. var. tropeana. (c) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:205 / 214
页数:10
相关论文
共 15 条
[1]   NMR spectroscopy of steroidal sapogenins and steroidal saponins: An update [J].
Agrawal, PK ;
Jain, DC ;
Pathak, AK .
MAGNETIC RESONANCE IN CHEMISTRY, 1995, 33 (12) :923-953
[2]   C-13 NMR SPECTRAL INVESTIGATIONS .10. C-13 NMR-SPECTROSCOPY OF STEROIDAL SAPOGENINS AND STEROIDAL SAPONINS [J].
AGRAWAL, PK ;
JAIN, DC ;
GUPTA, RK ;
THAKUR, RS .
PHYTOCHEMISTRY, 1985, 24 (11) :2479-2496
[3]   THE CHEMISTRY OF GARLIC AND ONIONS [J].
BLOCK, E .
SCIENTIFIC AMERICAN, 1985, 252 (03) :114-&
[4]   DIOSGENIN-BEARING, MOLLUSCICIDAL SAPONINS FROM ALLIUM-VINEALE - AN NMR APPROACH FOR THE STRUCTURAL ASSIGNMENT OF OLIGOSACCHARIDE UNITS [J].
CHEN, SX ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3679-3689
[5]  
Da Silva BP, 1999, PHYTOCHEMISTRY, V51, P931
[6]   Two novel furostanol saponins from the rhizomes of Dioscorea panthaica Prain et Burkill and their cytotoxic activity [J].
Dong, M ;
Feng, XZ ;
Wang, BX ;
Wu, LJ ;
Ikejima, T .
TETRAHEDRON, 2001, 57 (03) :501-506
[7]  
Harmatha J, 2000, PR PHYT SOC, V45, P129
[8]  
HIROMICHI M, 2001, J NUTR, V131, pS1000
[9]   Steroidal saponins from the bulbs of Lilium candidum [J].
Mimaki, Y ;
Satou, T ;
Kuroda, M ;
Sashida, Y ;
Hatakeyama, Y .
PHYTOCHEMISTRY, 1999, 51 (04) :567-573
[10]   Steroidal saponins from the underground parts of Ruscus aculeatus and their cytostatic activity on HL-60 cells [J].
Mimaki, Y ;
Kuroda, M ;
Kameyama, A ;
Yokosuka, A ;
Sashida, Y .
PHYTOCHEMISTRY, 1998, 48 (03) :485-493