Isolation of erinacine P, a new parental metabolite of cyathane-xylosides, from Hericium erinaceum and its biomimetic conversion into erinacines A and B

被引:112
作者
Kenmoku, H
Sassa, T [1 ]
Kato, N
机构
[1] Yamagata Univ, Fac Agr, Dept Bioresources, Yamagata 9978555, Japan
[2] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
关键词
biomimetic reactions; biosynthesis; glycosides; terpenes and terpenoids;
D O I
10.1016/S0040-4039(00)00601-8
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
A new cyathane-xyloside, erinacine P, was isolated from mycelia of basidiomycetous Hericium erinaceum YB4-6237 in a shaken culture. Since its aglycon closely resembles typical cyathane diterpenoids such as cyathins and cyathatriols in its substitution pattern, this glycoside seems to be an important metabolite in the biosynthesis of erinacines and striatins. In fact, according to our biogenesis studies, erinacine P can be successfully converted chemically into erinacine B and, further, to erinacine A under mild conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4389 / 4393
页数:5
相关论文
共 16 条
[1]
Ayer W. A., 1978, REV LATINOAM QUIM, V9, P177
[2]
METABOLITES OF BIRDS NEST FUNGI .11. DITERPENOID METABOLITES OF CYATHUS-EARLEI LLOYD [J].
AYER, WA ;
LEE, SP .
CANADIAN JOURNAL OF CHEMISTRY, 1979, 57 (24) :3332-3337
[3]
HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[4]
Ciganek E., 1997, ORG REACTIONS, V51, P201
[5]
STRIATIN-A, STRIATIN-B, AND STRIATIN-C - NOVEL DITERPENOID ANTIBIOTICS FROM CYATHUS-STRIATUS - X-RAY CRYSTAL-STRUCTURE OF STRIATIN-A [J].
HECHT, HJ ;
HOFLE, G ;
STEGLICH, W ;
ANKE, T ;
OBERWINKLER, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (15) :665-666
[6]
Inchausti A, 1997, PHYTOTHER RES, V11, P193, DOI 10.1002/(SICI)1099-1573(199705)11:3<193::AID-PTR68>3.3.CO
[7]
2-I
[8]
Kawagishi H, 1996, HETEROCYCL COMMUN, V2, P51
[9]
Erinacines E, F, and G, stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum [J].
Kawagishi, H ;
Shimada, A ;
Hosokawa, S ;
Mori, H ;
Sakamoto, H ;
Ishiguro, Y ;
Sakemi, S ;
Bordner, J ;
Kojima, N ;
Furukawa, S .
TETRAHEDRON LETTERS, 1996, 37 (41) :7399-7402
[10]
ERINACINE-A, ERINACINE-B AND ERINACINE-C, STRONG STIMULATORS OF NERVE GROWTH-FACTOR (NGF)-SYNTHESIS, FROM THE MYCELIA OF HERICIUM ERINACEUM [J].
KAWAGISHI, H ;
SHIMADA, A ;
SHIRAI, R ;
OKAMOTO, K ;
OJIMA, F ;
SAKAMOTO, H ;
ISHIGURO, Y ;
FURUKAWA, S .
TETRAHEDRON LETTERS, 1994, 35 (10) :1569-1572