Polyphenols isolated from the bark of Castanea sativa Mill. chemical structures and autoassociation

被引:38
作者
Lampire, O
Mila, I
Raminosoa, M
Michon, V
Du Penhoat, CH
Faucheur, N
Laprevote, O
Scalbert, A
机构
[1] Ecole Normale Super, Dept Chim, URA 1679, F-75231 Paris 05, France
[2] Inst Natl Agron Paris Grignon, INRA, Chim Biol Lab, Ctr Biotechnol Agroind, F-78850 Thiverval Grignon, France
[3] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
Castanea sativa; Fagaceae; chestnut; bark; ellagitannins; galloyl esters; phenol glycosides; hamamelitannins; intermolecular associations; NMR spectroscopy; mass spectrometry;
D O I
10.1016/S0031-9422(98)00114-9
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
Eight phenolic compounds (castalin, castalagin, vescalagin, kurigalin, 5-O-galloylhamamelose, (3', 5'-dimethoxy-4'-hydroxyphenol)-1-O-beta-D-(6-O-galloyl)glucose, chestanin, and acutissimin A) were isolated from chestnut bark and their structures elucidated on the basis of spectroscopic analyses. Evidence for strong intermolecular associations of 5-O-galloylhamamelose is presented on the basis of NMR and mass spectroscopic data. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:623 / 631
页数:9
相关论文
共 36 条
[1]   COMPLETE H-1 AND C-13 NMR ASSIGNMENT OF COMPLEX POLYCYCLIC AROMATIC-HYDROCARBONS [J].
BAX, A ;
FERRETTI, JA ;
NASHED, N ;
JERINA, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3029-3034
[2]  
Brouillard R., 1988, The Flavonoids, P525, DOI DOI 10.1007/978-1-4899-2913-6_16
[3]  
DANGLES O, 1994, NEW J CHEM, V18, P287
[4]  
DUPENHOAT CLMH, 1991, PHYTOCHEMISTRY, V30, P329, DOI 10.1016/0031-9422(91)84148-L
[5]   GALLOTANNINS .5. STRUCTURE OF PENTA- AND TETRA-O-GALLOYLGLUCOSES, AND SOME OBSERVATIONS ON MOLECULAR WEIGHTS OF GALLOTANNINS [J].
GRAMSHAW, JW ;
HAWORTH, RD ;
SEARLE, T ;
HASLAM, E .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (AUG) :2944-&
[6]  
Griffiths WJ, 1996, RAPID COMMUN MASS SP, V10, P1169
[7]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[8]  
ISHIMARU K, 1987, CHEM PHARM BULL, V35, P602
[9]   TANNINS AND RELATED-COMPOUNDS .54. PHENOLIC GLUCOSIDE GALLATES FROM QUERCUS-MONGOLICA AND QUERCUS-ACUTISSIMA [J].
ISHIMARU, K ;
NONAKA, G ;
NISHIOKA, I .
PHYTOCHEMISTRY, 1987, 26 (04) :1147-1152
[10]   ELLAGITANNINS AND COMPLEX TANNINS FROM QUERCUS-PETRAEA BARK [J].
KONIG, M ;
SCHOLZ, E ;
HARTMANN, R ;
LEHMANN, W ;
RIMPLER, H .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (10) :1411-1415