Tucupentol, a Novel Mono-tetrahydrofuranic Acetogenin from Annona montana, as a Potent Inhibitor of Mitochondrial Complex I

被引：17

作者：

Alvarez Colom, Olga ^{[1
]}

Neske, Adriana ^{[1
]}

Chahboune, Nadia ^{[2
]}

Carmen Zafra-Polo, M. ^{[2
]}

Bardon, Alicia ^{[1
]}

机构：

[1] Univ Nacl Tucumin, Inst Quim Organ, Fac Bioquim Quim & Farm, San Miguel De Tucuman, Argentina

[2] Univ Valencia, Dept Farmacol, Fac Farm, E-46100 Burjassot, Spain

来源：

CHEMISTRY & BIODIVERSITY | 2009年 / 6卷 / 03期

关键词：

RING ACETOGENINS; MURICATA; LEAVES;

D O I：

10.1002/cbdv.200800102

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：

Ten acetogenins, one of them new, were isolated from leaves and twigs of a Bolivian collection of Annona montana. The new compound that we named tucupentol (1) is a mono-tetrahydrofuran-pentahydroxy-acetogenin. The inhibitory potency of tucupentol (1) on the mitochondrial complex I was evaluated, and this activity was compared with that of the known acetogenins, annonacin-A, cis-annonacin-10-one, aromin, and gigantetronenin, also isolated from this plant material. The mentioned acetogenins acted as selective inhibitors of mitochondrial complex I in the 0.8-5.4-nM range.

引用

页码：335 / 340

页数：6

共 20 条

[1] Aromin and aromicin, two new bioactive annonaceous acetogenins, possessing an unusual bis-THF ring structure, from Xylopia aromatica (Annonaceae) [J].

Alfonso, D ;

ColmanSaizarbitoria, T ;

Zhao, GX ;

Shi, G ;

Ye, Q ;

Schwedler, JT ;

McLaughlin, JL .

TETRAHEDRON, 1996, 52 (12) :4215-4224

[2]

Alkofahi A., 1989, ACS SYM SER, P25

[3] Acetogenins from Annonaceae:: recent progress in isolation, synthesis and mechanisms of action [J].

Bermejo, A ;

Figadère, B ;

Zafra-Polo, MC ;

Barrachina, I ;

Estornell, E ;

Cortes, D .

NATURAL PRODUCT REPORTS, 2005, 22 (02) :269-303

[4]

Cave A, 1997, Fortschr Chem Org Naturst, V70, P81

[5] KEY ANTIFUNGAL, ANTIBACTERIAL AND ANTIINSECT ASSAYS - A CRITICAL-REVIEW [J].

COLE, MD .

BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1994, 22 (08) :837-856

[6] NATURAL SUBSTANCES (ACETOGENINS) FROM THE FAMILY ANNONACEAE ARE POWERFUL INHIBITORS OF MITOCHONDRIAL NADH DEHYDROGENASE (COMPLEX-I) [J].

ESPOSTI, MD ;

GHELLI, A ;

RATTA, M ;

CORTES, D ;

ESTORNELL, E .

BIOCHEMICAL JOURNAL, 1994, 301 :161-167

[7] GIGANTETRONENIN AND GIGANTRIONENIN - NOVEL CYTOTOXIC ACETOGENINS FROM GONIOTHALAMUS-GIGANTEUS [J].

FANG, XP ;

ANDERSON, JE ;

SMITH, DL ;

MCLAUGHLIN, JL ;

WOOD, KV .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (11) :1655-1663

[8] Steady-state kinetics of the reduction of coenzyme Q analogs by complex I (NADH:Ubiquinone oxidoreductase) in bovine heart mitochondria and submitochondrial particles [J].

Fato, R ;

Estornell, E ;

DiBernardo, S ;

Pallotti, F ;

Castelli, GP ;

Lenaz, G .

BIOCHEMISTRY, 1996, 35 (08) :2705-2716

[9] 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

[10] Novel cytotoxic monotetrahydrofuranic annonaceous acetogenins from Annona montana [J].

Liaw, CC ;

Chang, FR ;

Chen, SL ;

Wu, CC ;

Lee, KH ;

Wu, YC .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (15) :4767-4776

← 1 2 →