Structure-activity relationships of novel neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata

被引:30
作者
Han, Chunguang [1 ]
Qi, Jianhua [1 ]
Ojika, Makoto [1 ]
机构
[1] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan
基金
日本学术振兴会;
关键词
linckosides; steroid glycosides; marine natural products; neuritogenic activity;
D O I
10.1016/j.bmc.2006.02.032
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
Six new steroid glycosides, linckosides F-K, and a related metabolite were isolated from the Okinawan blue starfish Linckia laevigata as mimics or enhancers of nerve growth factor (NGF). Their structures and stereochemistry were elucidated by spectroscopic methods and chemical derivatization. Structure-activity relationships suggest that both a carbon branch modified by a pentose at the side chain and 2'-O-methylxylopyranose at C-3 of the aglycon are important for neuritogenic activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4458 / 4465
页数:8
相关论文
共 14 条
[1]
TROPHIC FACTORS AND NEURONAL SURVIVAL [J].
BARDE, YA .
NEURON, 1989, 2 (06) :1525-1534
[2]
STARFISH SAPONINS .41. STRUCTURE OF 2 NEW STEROIDAL GLYCOSIDE SULFATES (MINIATOSIDE-A AND MINIATOSIDE-B) AND 2 NEW POLYHYDROXYSTEROIDS FROM THE STARFISH PATIRIA-MINIATA [J].
DAURIA, MV ;
IORIZZI, M ;
MINALE, L ;
RICCIO, R ;
URIARTE, E .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (01) :94-101
[3]
Intranasal administration of nerve growth factor (NGF) rescues recognition memory deficits in AD11 anti-NGF transgenic mice [J].
De Rosa, R ;
Garcia, AA ;
Braschi, C ;
Capsoni, S ;
Maffei, L ;
Berardi, N ;
Cattaneo, A .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (10) :3811-3816
[4]
Nonmyeloablative conditioning allows for more rapid T-cell repertoire reconstitution following allogeneic matched unrelated bone marrow transplantation compared to myeloablative approaches [J].
Friedman, TM ;
Varadi, G ;
Hopely, DD ;
Filicko, J ;
Wagner, Y ;
Ferber, A ;
Martinez, J ;
Brunner, J ;
Grosso, D ;
McGuire, L ;
Korngold, R ;
Flomenberg, N .
BIOLOGY OF BLOOD AND MARROW TRANSPLANTATION, 2001, 7 (12) :656-664
[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]
NERVE GROWTH-FACTOR AND ALZHEIMERS-DISEASE [J].
HEFTI, F ;
WEINER, WJ .
ANNALS OF NEUROLOGY, 1986, 20 (03) :275-281
[7]
HEFTI F, 1989, NEUROBIOL AGING, V10, P515, DOI 10.1016/0197-4580(89)90118-8
[8]
Investigation of the polar steroids from an Antarctic starfish of the family Echinasteridae: Isolation of twenty seven polyhydroxysteroids and steroidal oligoglycosides, structures and biological activities [J].
Iorizzi, M ;
DeMarino, S ;
Minale, L ;
Zollo, F ;
LeBert, V ;
Roussakis, C .
TETRAHEDRON, 1996, 52 (33) :10997-11012
[9]
STARFISH SAPONINS .52. CHEMICAL-CONSTITUENTS FROM THE STARFISH ECHINASTER BRASILIENSIS [J].
IORIZZI, M ;
DERICCARDIS, F ;
MINALE, L ;
RICCIO, R .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (12) :2149-2162
[10]
NERVE GROWTH-FACTOR TREATMENT AFTER BRAIN INJURY PREVENTS NEURONAL DEATH [J].
KROMER, LF .
SCIENCE, 1987, 235 (4785) :214-216