Neuritogenic cerebrosides from an edible Chinese mushroom. Part 2: Structures of two additional termitomycesphins and activity enhancement of an inactive cerebroside by hydroxylation

被引：45

作者：

Qi, JH ^{[1
]}

Ojika, M ^{[1
]}

Sakagami, Y ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2001年 / 9卷 / 08期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0968-0896(01)00125-0

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：

Termitomycesphins E and F, novel cerebrosides that are hydroxylated around the middle of the long-chain base (LCB), have been isolated from the edible Chinese mushroom Termitomyces albuminosus (Berk.) Heim. ('Jizong' in Chinese) together with termitomycesphins A-D, and shown to induce neuronal differentiation in rat PC12 cells. Their stereostructures have been determined based on their chemical derivatization and spectroscopic analysis. The major cerebroside obtained from the same mushroom was not hydroxylated around the middle of the LCB and was inactive against PC12 cells, suggesting the importance of the extra hydroxyl group on LCB. The Di- and tetrahydroxylation of this inactive cerebroside resulted in the enhancement of its neuritogenic activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2171 / 2177

页数：7

共 15 条

[1] TROPHIC FACTORS AND NEURONAL SURVIVAL [J].

BARDE, YA .

NEURON, 1989, 2 (06) :1525-1534

[2]

BOTHWELL M, 1991, CURR TOP MICROBIOL, V165, P71

[3] AMELIORATION OF CHOLINERGIC NEURON ATROPHY AND SPATIAL MEMORY IMPAIRMENT IN AGED RATS BY NERVE GROWTH-FACTOR [J].

FISCHER, W ;

WICTORIN, K ;

BJORKLUND, A ;

WILLIAMS, LR ;

VARON, S ;

GAGE, FH .

NATURE, 1987, 329 (6134) :65-68

[4]

GILLIAN MN, 2000, J AM CHEM SOC, V122, P4011

[5] ESTABLISHMENT OF A NORADRENERGIC CLONAL LINE OF RAT ADRENAL PHEOCHROMOCYTOMA CELLS WHICH RESPOND TO NERVE GROWTH-FACTOR [J].

GREENE, LA ;

TISCHLER, AS .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1976, 73 (07) :2424-2428

[6] WOOL WAX .6. THE SYNTHESIS AND STEREOCHEMISTRY OF THE STRAIGHT-CHAIN ALPHA-HYDROXY-ACIDS [J].

HORN, DHS ;

PRETORIUS, YY .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (MAY) :1460-1464

[7] OPHIDIACEREBROSIDES - CYTOTOXIC GLYCOSPHINGOLIPIDS CONTAINING A NOVEL SPHINGOSINE FROM A SEA STAR [J].

JIN, WZ ;

RINEHART, KL ;

JARESERIJMAN, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :144-147

[8] NERVE GROWTH-FACTOR TREATMENT AFTER BRAIN INJURY PREVENTS NEURONAL DEATH [J].

KROMER, LF .

SCIENCE, 1987, 235 (4785) :214-216

[9] Termitomycesphins A-D, novel neuritogenic cerebrosides from the edible Chinese mushroom Termitomyces albuminosus [J].

Qi, JH ;

Ojika, M ;

Sakagami, Y .

TETRAHEDRON, 2000, 56 (32) :5835-5841

[10] THE LOCATION OF DOUBLE-BONDS IN A CEREBROSIDE FROM EDIBLE FUNGI (MUSHROOM) ESTIMATED BY B/E LINKED SCAN FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY [J].

SAWABE, A ;

MORITA, M ;

OKAMOTO, T ;

OUCHI, S .

BIOLOGICAL MASS SPECTROMETRY, 1994, 23 (11) :660-664

← 1 2 →