Two novel blue pigments with ellagitannin moiety, rosacyanins A1 and A2, isolated from the petals of Rosa hybrida

被引:19
作者
Fukui, Yuko
Nomoto, Kyosuke
Iwashita, Takashi
Masuda, Katsuyoshi
Tanaka, Yoshikazu
Kusumi, Takaaki
机构
[1] Suntory Ltd, Inst Hlth Care Sci, Osaka 6188503, Japan
[2] Toyo Univ, Fac Life Sci, Itakura, Gumma 3740193, Japan
[3] Suntory Inst Bioorgan Res, Osaka 6188503, Japan
[4] Suntory Ltd, Inst Adv Technol, Osaka 6188503, Japan
关键词
rose; Rosa hybrida; rosacyanin; anthocyanidin; ellagitannin; blue pigment; FABMS/MS/MS; C-13 isotope shift; COLOR; ANTHOCYANINS; TANNINS; COPIGMENTATION; GENTIODELPHIN; GLYCOSIDES; CHEMISTRY; QUERCUS;
D O I
10.1016/j.tet.2006.07.068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel blue pigments, rosacyanins A1 and A2, were isolated from the petals of Rosa hybrida cv. 'M'me. Violet'. Their structures were elucidated on the basis of high-resolution Fourier transform ion cyclotron resonance mass spectroscopy (HR-FT-ICR-MS), FABMS/MS/MS, H-1, C-13 and two-dimensional NMR. The molecular formulas of rosacyanin Al (1) and A2 (2) are C56H37O31 and C63H41O35, respectively. The structures of rosacyanins Al and A2 consisted of a common chromophore containing cyanidin with a galloyl group link between positions 4 and 5 of the hydroxyl group of the flavylium nucleus and tellimagrandins (1 or 2). These pigments in which anthocyanidin nuclei linked to ellagitannin through an ether bond are the first compounds isolated from natural sources. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9661 / 9670
页数:10
相关论文
共 35 条
[1]   COPIGMENTATION OF ANTHOCYANINS IN PLANT-TISSUES AND ITS EFFECT ON COLOR [J].
ASEN, S ;
STEWART, RN ;
NORRIS, KH .
PHYTOCHEMISTRY, 1972, 11 (03) :1139-&
[2]   Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines [J].
Bakker, J ;
Timberlake, CF .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (01) :35-43
[3]   Covalently linked anthocyanin-flavonol pigments from blue Agapanthus flowers [J].
Bloor, SJ ;
Falshaw, R .
PHYTOCHEMISTRY, 2000, 53 (05) :575-579
[4]   THE CHEMISTRY OF ROSE PIGMENTS [J].
EUGSTER, CH ;
MARKIFISCHER, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (06) :654-672
[5]   New aspects of anthocyanin complexation. Intramolecular copigmentation as a means for colour loss? [J].
Figueiredo, P ;
Elhabiri, M ;
Toki, K ;
Saito, N ;
Dangles, O ;
Brouillard, R .
PHYTOCHEMISTRY, 1996, 41 (01) :301-308
[6]   Structures of two diacylated anthocyanins from Petunia hybrida cv. Surfinia Violet Mini [J].
Fukui, Y ;
Kusumi, T ;
Yoshida, K ;
Kondo, T ;
Matsuda, C ;
Nomoto, K .
PHYTOCHEMISTRY, 1998, 47 (07) :1409-+
[7]   Structure of rosacyanin B, a novel pigment from the petals of Rosa hybrida [J].
Fukui, Y ;
Kusumi, T ;
Masuda, K ;
Iwashita, T ;
Nomoto, K .
TETRAHEDRON LETTERS, 2002, 43 (14) :2637-2639
[8]   STRUCTURE OF GENTIODELPHIN, AN ACYLATED ANTHOCYANIN ISOLATED FROM GENTIANA-MAKINOI, THAT IS STABLE IN DILUTE AQUEOUS-SOLUTION [J].
GOTO, T ;
KONDO, T ;
TAMURA, H ;
IMAGAWA, H ;
IINO, A ;
TAKEDA, K .
TETRAHEDRON LETTERS, 1982, 23 (36) :3695-3698
[9]   STRUCTURE OF PLATYCONIN, A DIACYLATED ANTHOCYANIN ISOLATED FROM THE CHINESE BELL-FLOWER PLATYCODON-GRANDIFLORUM [J].
GOTO, T ;
KONDO, T ;
TAMURA, H ;
KAWAHORI, K ;
HATTORI, H .
TETRAHEDRON LETTERS, 1983, 24 (21) :2181-2184
[10]   STRUCTURE AND MOLECULAR STACKING OF ANTHOCYANINS - FLOWER COLOR VARIATION [J].
GOTO, T ;
KONDO, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :17-33