Biomimic transformation of resveratrol

被引:139
作者
Takaya, Y [1 ]
Terashima, K [1 ]
Ito, J [1 ]
He, YH [1 ]
Tateoka, M [1 ]
Yamaguchi, N [1 ]
Niwa, M [1 ]
机构
[1] Meijo Univ, Fac Pharm, Tempa Ku, Nagoya, Aichi 4688503, Japan
关键词
resveratrol; peroxidase; epsilon-viniferin; thallium(III) nitrate;
D O I
10.1016/j.tet.2005.08.023
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Resveratrol was treated with several kinds of peroxidases and inorganic reagents so as to prepare E-viniferin. Among several inorganic reagents, which were investigated in this study, thallium(III) nitrate in methanol gave (+/-)-epsilon-viniferin in the yield of 68%. On the other hand, peroxidases did not lead to F-viniferin, but some stilbenedimers such as pallidol, resveratrol trans-dehydrodimer, and leachianol F were obtained. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10285 / 10290
页数:6
相关论文
共 11 条
[1]
Stilbene derivatives from Cissus quadrangularis [J].
Adesanya, SA ;
Nia, R ;
Martin, MT ;
Boukamcha, N ;
Montagnac, A ;
Païs, M .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12) :1694-1695
[2]
Absolute structures of new hydroxystilbenoids, vitisin C and viniferal, from Vitis vinifera 'Kyohou' [J].
Ito, J ;
Niwa, M .
TETRAHEDRON, 1996, 52 (30) :9991-9998
[3]
OXIDATIVE DIMERIZATION OF 4-HYDROXYSTILBENES INVITRO - PRODUCTION OF A GRAPEVINE PHYTOALEXIN MIMIC [J].
LANGCAKE, P ;
PRYCE, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (07) :208-210
[4]
DIRECT PREPARATION OF 5-AMINO-1,3-PENTADIENES THROUGH USE OF PALLADIUM-PROMOTED REACTIONS [J].
NIKAIDO, M ;
ASLANIAN, R ;
SCAVO, F ;
HELQUIST, P ;
AKERMARK, B ;
BACKVALL, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24) :4738-4740
[5]
5 RESVERATROL OLIGOMERS FROM ROOTS OF SOPHORA-LEACHIANA [J].
OHYAMA, M ;
TANAKA, T ;
IINUMA, M .
PHYTOCHEMISTRY, 1995, 38 (03) :733-740
[6]
Regioselective oxidative coupling of 4-hydroxystilbenes:: Synthesis of resveratrol and ε-viniferin (E)-dehydrodimers [J].
Sako, M ;
Hosokawa, H ;
Ito, T ;
Iinuma, MI .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2598-2600
[7]
Biogenetic reactions on stilbenetetramers from Vitaceaeous plants [J].
Takaya, Y ;
Yan, KX ;
Terashima, K ;
He, YH ;
Niwa, M .
TETRAHEDRON, 2002, 58 (45) :9265-9271
[8]
Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F [J].
Takaya, Y ;
Yan, KX ;
Terashima, K ;
Ito, J ;
Niwa, M .
TETRAHEDRON, 2002, 58 (36) :7259-7265
[9]
Takaya Y., 2001, TRENDS HETEROCYCL CH, V7, P41
[10]
Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures [J].
Waffo-Teguo, P ;
Lee, D ;
Cuendet, M ;
Mérillon, JM ;
Pezzuto, JM ;
Kinghorn, AD .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (01) :136-138