Cytotoxic triterpenoid saponins from the stem bark of Antonia ovata

被引：7

作者：

Magid, Abdulmagid Alabdul ^{[1
]}

Bobichon, Helene ^{[2
]}

Borie, Nicolas ^{[1
]}

Lalun, Nathalie ^{[3
]}

Long, Christophe ^{[4
]}

Moretti, Christian ^{[5
]}

Lavaud, Catherine ^{[1
]}

机构：

[1] CNRS, Inst Chim Mol Reims, Lab Pharmacognosie, IFR Biomol 53,UMR 6229, Batiment 18,BP 1039, F-51687 Reims 2, France

[2] Univ Reims, CNRS, UMR 6237, F-51095 Reims, France

[3] UFR Med, Lab Biol Cellulaire Genet & Histol, F-51095 Reims, France

[4] CNRS, Inst Rech Pierre Fabre, ISTMT, UMS 2597, F-31432 Toulouse, France

[5] SAE, UMR 138, IRD, F-98713 Papeete, Tahiti, France

来源：

PHYTOCHEMISTRY | 2010年 / 71卷 / 04期

关键词：

Antonia ovata; Loganiaceae; Triterpenoid saponins; R-1-barrigenol; A(1)-barrigenol; Barringtogenol C; Camelliagenin; Cytotoxic activity; ICHTHYOTOXIC PLANTS; IRIDOIDS; ACID;

D O I：

10.1016/j.phytochem.2009.11.007

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：

Phytochemical investigation of the MeOH extract of the stem bark of Antonia ovata led to the isolation of four triterpenoid saponins, along with eleven known Compounds Their structures were established by extensive 1D and 2D NMR, as well as HR-MS analysis and acid hydrolysis All isolated saponins contained the same tetrasaccharide chain O-beta-D-xylopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 3)-O-[beta-D-glucopyranosyl-(1 -> 2)]-beta-D-glucuropyranoside linked to C-3 of esterified derivatives of R-1-barrigenol. A(1)-barrigenol, barringtogenol C, or camelliagenin Biological evaluation of the Compounds against KB cell line revealed a potent cytotoxic activity with IC50 Values ranging from 3 1 to 6 6 mu M. The known compounds were found to be inactive at 10 mu g/ml concentration. (C) 2009 Elsevier Ltd All rights reserved.

引用

页码：429 / 434

页数：6

共 16 条

[1] NMR-SPECTROSCOPY IN THE STRUCTURAL ELUCIDATION OF OLIGOSACCHARIDES AND GLYCOSIDES [J].

AGRAWAL, PK .

PHYTOCHEMISTRY, 1992, 31 (10) :3307-3330

[2] PLANTS OF NEW-CALEDONIA .137. IRIDOIDS FROM COELOSPERMUM-BILLARDIERI [J].

BENKRIEF, R ;

SKALTSOUNIS, AL ;

TILLEQUIN, F ;

KOCH, M ;

PUSSET, J .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :532-541

[3]

Bisset N.G., 1980, INDOLE BIOGENETICALL, P27

[4] Structure-activity relationships of some hederagenin diglycosides:: Haemolysis, cytotoxicity and apoptosis induction [J].

Chwalek, Martin ;

Lalun, Nathalie ;

Bobichon, Helene ;

Ple, Karen ;

Voutquenne-Nazabadioko, Laurence .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2006, 1760 (09) :1418-1427

[5] IRIDOIDS - A REVIEW [J].

ELNAGGAR, LJ ;

BEAL, JL .

JOURNAL OF NATURAL PRODUCTS, 1980, 43 (06) :649-707

[6] Iridoid glucosides from Galium album and G-lovcense [J].

Handjieva, N ;

Mitova, M ;

Ancev, M ;

Popov, S .

PHYTOCHEMISTRY, 1996, 43 (03) :625-628

[7] ALKALOIDS OF HUNTERIA-ZEYLANICA [J].

LAVAUD, C ;

MASSIOT, G ;

VERCAUTEREN, J ;

MENOLIVIER, LL .

PHYTOCHEMISTRY, 1982, 21 (02) :445-447

[8] Preliminary assays indicate that Antonia ovata (Loganiaceae) and Derris amazonica (Papilionaceae), ichthyotoxic plants used for fishing in Roraima, Brazil, have an insecticide effect on Lutzomyia longipalpis (Diptera: Psychodidae: Phlebotominae) [J].

Luitgards-Moura, JF ;

Bermudez, EGC ;

Felisberto, A ;

da Rocha, I ;

Tsouris, P ;

Rosa-Freitas, MG .

MEMORIAS DO INSTITUTO OSWALDO CRUZ, 2002, 97 (05) :737-742

[9] THE FISHING POISONS OR ICHTHYOTOXIC PLANTS OF FRENCH-GUYANA [J].

MORETTI, C ;

GRENAND, P .

JOURNAL OF ETHNOPHARMACOLOGY, 1982, 6 (02) :139-160

[10] Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L.) [J].

Nakatani, N ;

Kayano, S ;

Kikuzaki, H ;

Sumino, K ;

Katagiri, K ;

Mitani, T .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (11) :5512-5516

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