Montacin and cis-montacin, two new cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona montana

被引:18
作者
Liaw, CC
Chang, FR
Wu, YC [2 ]
Wang, HK
Nakanishi, Y
Bastow, KF
Lee, KH
机构
[1] Univ N Carolina, Nat Prod Lab, Sch Pharm, Chapel Hill, NC 27599 USA
[2] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan
来源
JOURNAL OF NATURAL PRODUCTS | 2004年 / 67卷 / 11期
关键词
D O I
10.1021/np030216p
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new monotetrahydrofuran Annonaceous acetogenins, montacin (1), and cis-montacin (2), along with four known acetogenins, annonacin, cis-annonacin, annomontacin, and cis-annomontacin, were isolated from the seeds of Annona montana. The structures of the new isolates were elucidated by spectral and chemical methods. The new acetogenins exhibited moderate in vitro cytotoxic activity against the 1A9 human ovarian cancer cell line. Interestingly, when Ca2+ was present, compounds 1 and 2 became 3- to 10-fold more active against 1A9 cells and the PTX10 subline.
引用
收藏
页码:1804 / 1808
页数:5
相关论文
共 20 条
[1]   Annonaceous acetogenins: Recent progress [J].
Alali, FQ ;
Liu, XX ;
McLaughlin, JL .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540
[2]   THE RELATIVE CONFIGURATION OF ACETOGENINS ISOLATED FROM ANNONA-SQUAMOSA - ANNONIN-I (SQUAMOCIN) AND ANNONIN-VI [J].
BORN, L ;
LIEB, F ;
LORENTZEN, JP ;
MOESCHLER, H ;
NONFON, M ;
SOLLNER, R ;
WENDISCH, D .
PLANTA MEDICA, 1990, 56 (03) :312-316
[3]  
FUJIMOTO Y, 1994, CHEM PHARM BULL, V42, P1175, DOI 10.1248/cpb.42.1175
[4]   Screening for Annonaceous acetogenins in bioactive plant extracts by liquid chromatography mass spectrometry [J].
Gu, ZM ;
Zhou, DW ;
Wu, J ;
Shi, G ;
Zeng, L ;
McLaughlin, JL .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (03) :242-248
[5]   Isolation of new bioactive annonaceous acetogenins from Rollinia mucosa guided by liquid chromatography mass spectrometry [J].
Gu, ZM ;
Zhou, DW ;
Lewis, NJ ;
Wu, J ;
Shi, GE ;
McLaughlin, JL .
BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (10) :1911-1916
[6]   ANNOMONTACIN - NEW CYTOTOXIC ACETOGENIN GAMMA-LACTONE MONOTETRAHYDROFURAN ISOLATED FROM ANNONA-MONTANA [J].
JOSSANG, A ;
DUBAELE, B ;
CAVE, A ;
BARTOLI, MH ;
BERIEL, H .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :967-971
[7]   A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop annonaceous acetogenins as potential antitumor agents [J].
Liaw, CC ;
Chang, FR ;
Wu, MJ ;
Wu, YC .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (02) :279-281
[8]   New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata [J].
Liaw, CC ;
Chang, FR ;
Lin, CY ;
Chou, CJ ;
Chiu, HF ;
Wu, MJ ;
Wu, YC .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (04) :470-475
[9]   ANNONACIN, A NOVEL, BIOLOGICALLY-ACTIVE POLYKETIDE FROM ANNONA-DENSICOMA [J].
MCCLOUD, TG ;
SMITH, DL ;
CHANG, CJ ;
CASSADY, JM .
EXPERIENTIA, 1987, 43 (08) :947-949
[10]   Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line [J].
Nakanishi, Y ;
Chang, FR ;
Liaw, CC ;
Wu, YC ;
Bastow, KF ;
Lee, KH .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) :3185-3188