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Noncytotoxic and Antitumour-Promoting Activities of Garcinia Acid Esters from Garcinia atroviridis Griff. ex T. Anders (Guttiferae).

Mackeen MM, Mooi LY, Amran M, Mat N, Lajis NH, Ali AM - Evid Based Complement Alternat Med (2012)

Bottom Line: Anders (Guttiferae), were examined.Although the antitumour-promoting activity of compound 1 is moderate compared with the known antitumour promoter genistein, its non-toxicity suggests the potential of compound 1 and related structures as chemopreventive agents.The weak antioxidant activity displayed by both compounds also suggested that the primary antitumour-promoting mechanism of compound 1 did not involve oxidative-stress quenching.

View Article: PubMed Central - PubMed

Affiliation: Department of Cell and Molecular Biology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, Selangor, 43400 Serdang, Malaysia.

ABSTRACT
The in vitro antitumour-promoting, cytotoxic, and antioxidant activities of two ester derivatives of garcinia acid, that is, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide (1) and 1',1''-dibutyl methyl hydroxycitrate (2), that had been previously isolated from the fruits of Garcinia atroviridis Griff. ex T. Anders (Guttiferae), were examined. Based on the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation, compound 1 (IC(50): 70 μM) showed much higher (8-fold) antitumour-promoting activity than compound 2 (IC(50): 560 μM). In addition, both compounds were nontoxic towards CEM-SS (human T-lymphoblastic leukemia) cells (CD(50): >100 μM), Raji (human B-lymphoblastoid) cells (CD(50): >600 μM), and brine shrimp (LD(50): >300 μM). Although the antitumour-promoting activity of compound 1 is moderate compared with the known antitumour promoter genistein, its non-toxicity suggests the potential of compound 1 and related structures as chemopreventive agents. The weak antioxidant activity displayed by both compounds also suggested that the primary antitumour-promoting mechanism of compound 1 did not involve oxidative-stress quenching.

No MeSH data available.


Related in: MedlinePlus

The structures of the compound 1 (2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide) and compound 2 (1′,1′′-dibutyl methyl hydroxycitrate).
© Copyright Policy - open-access
Related In: Results  -  Collection


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fig1: The structures of the compound 1 (2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide) and compound 2 (1′,1′′-dibutyl methyl hydroxycitrate).

Mentions: The occurrence of xanthones, benzophenones, and biflavonoids is common in the Garcinia genus [2]. To date, the metabolites that have been isolated from G. atroviridis are atroviridin (xanthone); atrovirinone and 4-methylhydroatrovirinone (prenylated quinones); atrovirisidone and atrovirisidone B (prenylated depsidones); along with the known metabolites morelloflavone, fukugiside, naringenin, 3,8′′-binaringenin, 14-cis-docosenoic acid, garcinia acid (same as (−)-hydroxycitric acid) and its γ-lactone [3–7]. Garcinia acid, which has been primarily obtained from the Garcinia genus, is an effective inhibitor of lipogenesis with commercial and clinical applications [8]. Previously, two garcinia acid esters, namely, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide and 1′,1′′-dibutyl methyl hydroxycitrate (Figure 1) had been isolated from the fruits of G. atroviridis, guided by antifungal activity against Cladosporium herbarum [1, 9]. In this paper, we reported the antitumour-promoting, antioxidant and cytotoxic activities of both these compounds.


Noncytotoxic and Antitumour-Promoting Activities of Garcinia Acid Esters from Garcinia atroviridis Griff. ex T. Anders (Guttiferae).

Mackeen MM, Mooi LY, Amran M, Mat N, Lajis NH, Ali AM - Evid Based Complement Alternat Med (2012)

The structures of the compound 1 (2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide) and compound 2 (1′,1′′-dibutyl methyl hydroxycitrate).
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3368197&req=5

fig1: The structures of the compound 1 (2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide) and compound 2 (1′,1′′-dibutyl methyl hydroxycitrate).
Mentions: The occurrence of xanthones, benzophenones, and biflavonoids is common in the Garcinia genus [2]. To date, the metabolites that have been isolated from G. atroviridis are atroviridin (xanthone); atrovirinone and 4-methylhydroatrovirinone (prenylated quinones); atrovirisidone and atrovirisidone B (prenylated depsidones); along with the known metabolites morelloflavone, fukugiside, naringenin, 3,8′′-binaringenin, 14-cis-docosenoic acid, garcinia acid (same as (−)-hydroxycitric acid) and its γ-lactone [3–7]. Garcinia acid, which has been primarily obtained from the Garcinia genus, is an effective inhibitor of lipogenesis with commercial and clinical applications [8]. Previously, two garcinia acid esters, namely, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide and 1′,1′′-dibutyl methyl hydroxycitrate (Figure 1) had been isolated from the fruits of G. atroviridis, guided by antifungal activity against Cladosporium herbarum [1, 9]. In this paper, we reported the antitumour-promoting, antioxidant and cytotoxic activities of both these compounds.

Bottom Line: Anders (Guttiferae), were examined.Although the antitumour-promoting activity of compound 1 is moderate compared with the known antitumour promoter genistein, its non-toxicity suggests the potential of compound 1 and related structures as chemopreventive agents.The weak antioxidant activity displayed by both compounds also suggested that the primary antitumour-promoting mechanism of compound 1 did not involve oxidative-stress quenching.

View Article: PubMed Central - PubMed

Affiliation: Department of Cell and Molecular Biology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, Selangor, 43400 Serdang, Malaysia.

ABSTRACT
The in vitro antitumour-promoting, cytotoxic, and antioxidant activities of two ester derivatives of garcinia acid, that is, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy-3-propanolide (1) and 1',1''-dibutyl methyl hydroxycitrate (2), that had been previously isolated from the fruits of Garcinia atroviridis Griff. ex T. Anders (Guttiferae), were examined. Based on the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation, compound 1 (IC(50): 70 μM) showed much higher (8-fold) antitumour-promoting activity than compound 2 (IC(50): 560 μM). In addition, both compounds were nontoxic towards CEM-SS (human T-lymphoblastic leukemia) cells (CD(50): >100 μM), Raji (human B-lymphoblastoid) cells (CD(50): >600 μM), and brine shrimp (LD(50): >300 μM). Although the antitumour-promoting activity of compound 1 is moderate compared with the known antitumour promoter genistein, its non-toxicity suggests the potential of compound 1 and related structures as chemopreventive agents. The weak antioxidant activity displayed by both compounds also suggested that the primary antitumour-promoting mechanism of compound 1 did not involve oxidative-stress quenching.

No MeSH data available.


Related in: MedlinePlus