Antitumor agents.: 228.: Five new agarofurans, reissantins A-E, and cytotoxic principles from Reissantia buchananiii

被引:74
作者
Chang, FR
Hayashi, K
Chen, IH
Liaw, CC
Bastow, KF
Nakanishi, Y
Nozaki, H
Cragg, GA
Wu, YC
Lee, KH
机构
[1] Univ N Carolina, Sch Pharm, Nat Prod Lab, Chapel Hill, NC 27599 USA
[2] NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA
[3] Okayama Univ Sci, Fac Sci, Dept Biochem, Okayama 7000005, Japan
[4] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan
来源
JOURNAL OF NATURAL PRODUCTS | 2003年 / 66卷 / 11期
关键词
SESQUITERPENE PYRIDINE ALKALOIDS; TRITERPENES; CONSTITUENTS; DATURADIOL; TERPENOIDS; DITERPENES; WILFORDII; STEROIDS;
D O I
10.1021/np030241v
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Twenty-one compounds, including five new agarofuran sesquiterpenes, reissantins A-E (1-5), were isolated from Reissantia buchananii by means of bioassay-directed fractionation and their structures identified from spectral data. Reissantins A-C are the first reported simple agarofuran sesquiterpenes to contain a 5-carboxy-N-methyl-2-pyridone (CNMP) substituent, which has previously been found only in macroring agarofuran pyridine alkaloids. The major terpenoid components, celastrol (6) and its methyl ester derivative, pristimerin (7), were significantly active against nine cancer cell lines, including A549, MCF-7, HCT-8, KB, KB-VIN, U-87-MG, PC-3, 1A9, and PTX10 cell lines, with ED50 values ranging from 0.076 to 0.34 mug/mL.
引用
收藏
页码:1416 / 1420
页数:5
相关论文
共 24 条
[1]  
Alves JS, 2000, MAGN RESON CHEM, V38, P201, DOI 10.1002/(SICI)1097-458X(200003)38:3<201::AID-MRC622>3.3.CO
[2]  
2-S
[3]   Resorcinol derivatives and flavonoids of Ononis natrix subspecies ramosissima [J].
Barrero, AF ;
Herrador, MM ;
Arteaga, P ;
RodriguezGarcia, I ;
GarciaMoreno, M .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (02) :65-68
[4]  
DELLEMONACHE F, 1972, GAZZ CHIM ITAL, V102, P636
[5]   A NOVEL TYPE OF TRITERPENOID QUINONE METHIDE PIGMENT FROM THE TOADSTOOL RUSSULA-FLAVIDA (AGARICALES) [J].
FRODE, R ;
BROCKELMANN, M ;
STEFFAN, B ;
STEGLICH, W ;
MARUMOTO, R .
TETRAHEDRON, 1995, 51 (09) :2553-2560
[6]   Sesquiterpene pyridine alkaloids from Hippocratea excelsa [J].
Furukawa, M ;
Makino, M ;
Uchiyama, T ;
Ishimi, K ;
Ichinohe, Y ;
Fujimoto, Y .
PHYTOCHEMISTRY, 2002, 59 (07) :767-777
[7]   THE STRUCTURE OF CELASTRANHYDRIDE - A NOVEL TRITERPENE ANHYDRIDE OF CELASTRACEAE [J].
GAMLATH, CB ;
GUNATILAKA, AAL ;
TEZUKA, Y ;
KIKUCHI, T .
TETRAHEDRON LETTERS, 1988, 29 (01) :109-112
[8]   STUDIES ON TERPENOIDS AND STEROIDS .13. REISSANTIOLOXIDE - A NOVEL EPOXYTRITERPENOID FROM REISSANTIA-INDICA - X-RAY CRYSTAL-STRUCTURE [J].
GAMLATH, CB ;
GUNATILAKA, AAL ;
SCHLEMPER, EO .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :249-250
[9]  
GAMLATH CB, 1989, J CHEM SOC P1, V12, P2259
[10]   STUDIES ON TERPENOIDS AND STEROIDS .3. STRUCTURE AND SYNTHESIS OF A NEW PHENOLIC D-A-FRIEDO-24-NOROLEANANE TRITERPENOID, ZEYLASTERONE, FROM KOKOONA-ZEYLANICA [J].
GUNAHERATH, GMKB ;
GUNATILAKA, AAL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :2845-2850