Glycosylation of capsaicin and 8-nordihydrocapsaicin by cultured cells of Catharanthus roseus

被引:42
作者
Shimoda, Kei
Kwon, Soonil
Utsuki, Akiko
Ohiwa, Shingo
Katsuragi, Hisashi
Yonemoto, Naoko
Hamada, Hatsuyuki
Hamada, Hiroki
机构
[1] Okayama Univ Sci, Fac Sci, Dept Life Sci, Okayama 7000005, Japan
[2] Natl Inst Fitness & Sports Kanoya, Kagoshima 8912390, Japan
[3] Sunny Hlth Co Ltd, Chuo Ku, Tokyo 1030028, Japan
[4] Okayama Univ Sci, Fac Sci, Dept Appl Sci, Okayama 7000005, Japan
[5] Oita Univ, Fac Med, Dept Pharm & Therapeut, Oita 8795593, Japan
关键词
Catharanthus roseus; apocynaceae; cultured plant cells; glycosylation; capsaicin; 8-nordihydrocapsaicin; beta-glucoside; beta-primeveroside; beta-vicianoside;
D O I
10.1016/j.phytochem.2007.03.005
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
The glycosylation of capsaicin and 8-nordihydrocapsaicin was investigated using cultured cells of Catharanthus roseus. In addition to capsaicin 4-O-beta-D-glucopyranoside (170 mu g/g fr. wt of cells), the biotransformation products, capsaicin 4-O-(6-O-beta-D-xylopyranosyl)-beta-glucopyranoside (116 mu g/g fr. wt of cells) and capsaicin 4-O-(6-O-alpha-L-arabinopyranosyl)-beta-D-glucopyranoside (83 mu g/g fr. wt of cells), were isolated from the cell suspension after three days of incubation with capsaicin. Two other compounds, 8-nordihydrocapsaicin 4-O(6-O-beta-D-Xylopyranosyl)-beta-D-glucopyranoside (171 mu g/g fr. wt of cells) and 8-nordihydrocapsaicin 4-O-(6-O-alpha-L-arabinopyranosyl)-beta-D-glucopyranoside (122 mu/g fr. wt of cells), together with the known 8-nordihydrocapsaicin 4-O-beta-D-glucopyranoside (204 mu g/g fr. wt of cells) were also isolated from the cell suspension after incubation with 8-nordihydrocapsaicin. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1391 / 1396
页数:6
相关论文
共 33 条
[1]
FORMATION AND METABOLISM OF THE PUNGENT PRINCIPLE OF CAPSICUM FRUITS .12. INTRACELLULAR DISTRIBUTIONS OF ENZYMES AND INTERMEDIATES INVOLVED IN BIOSYNTHESIS OF CAPSAICIN AND ITS ANALOGS IN CAPSICUM FRUITS [J].
FUJIWAKE, H ;
SUZUKI, T ;
IWAI, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (11) :2685-2689
[2]
FORMATION AND METABOLISM OF THE PUNGENT PRINCIPLE OF CAPSICUM FRUITS .11. CAPSAICINOID FORMATION IN THE PROTOPLAST FROM THE PLACENTA OF CAPSICUM FRUITS [J].
FUJIWAKE, H ;
SUZUKI, T ;
IWAI, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (10) :2591-2592
[3]
STUDIES ON PLANT-TISSUE CULTURE .51. BIOTRANSFORMATION OF PHENYLACETIC ACID AND 2-PHENYL-PROPIONIC ACID IN SUSPENSION-CULTURE OF COFFEA-ARABICA [J].
FURUYA, T ;
USHIYAMA, M ;
ASADA, Y ;
YOSHIKAWA, T ;
ORIHARA, Y .
PHYTOCHEMISTRY, 1988, 27 (03) :803-807
[4]
STUDIES ON PLANT-TISSUE CULTURE .59. BIOTRANSFORMATION OF 2-PHENYLPROPIONIC ACID IN ROOT CULTURE OF PANAX-GINSENG [J].
FURUYA, T ;
USHIYAMA, M ;
ASADA, Y ;
YOSHIKAWA, T .
PHYTOCHEMISTRY, 1989, 28 (02) :483-487
[5]
Hamada H., 2003, Plant Biotechnology, V20, P253, DOI 10.5511/plantbiotechnology.20.253
[6]
HYDROXYLATION OF PIPERITONE BY CELL-SUSPENSION CULTURES OF CATHARANTHUS-ROSEUS [J].
HAMADA, H ;
FUCHIKAMI, Y ;
IKEMATSU, Y ;
HIRATA, T ;
WILLIAMS, HJ ;
SCOTT, AI .
PHYTOCHEMISTRY, 1994, 37 (04) :1037-1038
[7]
Preparation of a new pepper: chemoenzymatic synthesis of capsaicin oligosaccharide and 8-nordihydrocapsaicin oligosaccharide [J].
Hamada, H ;
Nishida, K ;
Furuya, T ;
Ishihara, K ;
Nakajima, N .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 16 (02) :115-119
[8]
Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits [J].
Higashiguchi, Fumiharu ;
Nakamura, Hiroyasu ;
Hayashi, Hideo ;
Kometani, Takashi .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (16) :5948-5953
[9]
GLUCOSYLATION OF BUTYRIC-ACID BY CELL-SUSPENSION CULTURE OF NICOTIANA-PLUMBAGINIFOLIA [J].
KAMEL, S ;
BRAZIER, M ;
DESMET, G ;
FLINIAUX, MA ;
JACQUINDUBREUIL, A .
PHYTOCHEMISTRY, 1992, 31 (05) :1581-1583
[10]
Biotransformation and impact of ferulic acid on phenylpropanoid and capsaicin levels in Capsicum annuum L. cv. P1482 cell suspension cultures [J].
Kang, SM ;
Jung, HY ;
Kang, YM ;
Min, JY ;
Karigar, CS ;
Yang, JK ;
Kim, SW ;
Ha, YR ;
Lee, SH ;
Choi, MS .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (09) :3449-3453