SYNTHESIS OF 3β-HYDROXY-20-OXO-30-NORLUPAN-28-OIC (PLATANIC) ACID AND ITS GLYCOSIDES

被引:8
作者
Denisenko, M. V. [1 ]
Samoshina, N. F. [1 ]
Denisenko, V. A. [1 ]
Dmitrenok, P. S. [1 ]
机构
[1] Russian Acad Sci, Pacific Inst Bioorgan Chem, Far E Branch, Vladivostok 690022, Russia
关键词
betulin; platanic acid; glucosides; PMR; C-13; NMR; BETULINIC ACID; LUPANE-TYPE; TRITERPENOIDS; DERIVATIVES; AGENTS;
D O I
10.1007/s10600-011-0048-5
中图分类号
R914 [药物化学];
学科分类号
100705 [微生物与生化药学];
摘要
All available literature data on the chemical synthesis and isolation from natural sources of 3 beta-hydroxy-20-oxo-30-norlupan-28-oic (platanic) acid and its derivatives and their biological activity were reviewed. A one-step synthesis of platanic acid from betulin was developed. Its glycosylation by alpha-acetobromoglucose (ABG) catalyzed by Ag2O in various solvents such as pyridine, CH2Cl2, and their mixture was studied. The optimal synthetic schemes for platanic acid monoglucosides and diglucoside were found. NMR spectra of platanic acid and its glycosides were studied.
引用
收藏
页码:741 / 748
页数:8
相关论文
共 18 条
[1]
CHEMISTRY OF TRITERPENES AND RELATED COMPOUNDS .43. CONSTITUENTS OF BARK OF PLATANUS X HYBRIDA BROT AND STRUCTURE OF PLATANIC ACID [J].
APLIN, RT ;
HALSALL, TG ;
NORIN, T .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, :3269-&
[2]
Denisenko M. V., 1991, CHEM NAT COMPD+, V27, P374
[3]
TERPENOIDS .23. INTERCONVERSION OF THURBEROGENIN AND BETULINIC ACID [J].
DJERASSI, C ;
HODGES, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (14) :3534-3538
[4]
Cytotoxic lupane-, secolupane-, and oleanane-type triterpenes from Viburnum awabuki [J].
El-Gamal, Ali A. .
NATURAL PRODUCT RESEARCH, 2008, 22 (03) :191-197
[5]
ANTI-AIDS AGENTS .11. BETULINIC ACID AND PLATANIC ACID AS ANTI-HIV PRINCIPLES FROM SYZIGIUM-CLAVIFLORUM, AND THE ANTI-HIV ACTIVITY OF STRUCTURALLY RELATED TRITERPENOIDS [J].
FUJIOKA, T ;
KASHIWADA, Y ;
KILKUSKIE, RE ;
COSENTINO, LM ;
BALLAS, LM ;
JIANG, JB ;
JANZEN, WP ;
CHEN, IS ;
LEE, KH .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (02) :243-247
[6]
Hyek E. W. H., 1989, PHYTOCHEMISTRY, V28, P2229
[7]
Junges MJ, 1999, J BRAZIL CHEM SOC, V10, P317
[8]
Development of C-20 modified betulinic acid derivatives as antitumor agents [J].
Kim, JY ;
Koo, HM ;
Kim, DSHL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (17) :2405-2408
[9]
A new norlupene from the leaves of Melaleuca leucadendron [J].
Lee, CK .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (03) :375-376
[10]
Triterpenic acids from Eugenia moraviana [J].
Lunardi, I ;
Peixoto, JLB ;
da Silva, CC ;
Shuquel, ITA ;
Basso, EA ;
Vidotti, GJ .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (02) :180-183