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Compounds obtained from sida acuta with the potential to induce quinone reductase and to inhibit 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary organ culture model.

Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, Center for Pharmaceutical Biotechnology, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, U.S.A.
Archives of Pharmacal Research (Impact Factor: 1.75). 09/2003; 26(8):585-90. DOI: 10.1007/BF02976704
Source: PubMed

ABSTRACT Activity-guided fractionation of the EtOAc-soluble extract of the whole plants of Sida acuta using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells, led to the isolation of ten active compounds of previously known structure, quindolinone (1), cryptolepinone (2), 11-methoxyquindoline (3), N-trans-feruloyltyramine (4), vomifoliol (5), loliolide (6), 4-ketopinoresinol (7), scopoletin (8), evofolin-A (9), and evofolin-B (10), along with five inactive compounds of known structure, ferulic acid, sinapic acid, syringic acid, (+/-)-syringaresinol, and vanillic acid. These isolates were identified by physical and spectral data measurement. A new derivative of quindolinone, 5,10-dimethylquindolin-11-one (1a) was synthesized and characterized spectroscopically. Of the active substances, compounds 1-3 and 1a exhibited the most potent QR activity, with observed CD (concentration required to double induction) values ranging from 0.01 to 0.12 microg/mL. Six compounds were then evaluated in a mouse mammary organ culture assay, with cryptolepinone (2), N-trans-feruloyltyramine (4), and 5,10-dimethylquindolin-11-one (1a) found to exhibit 83.3, 75.0, and 66.7% inhibition of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions, respectively, at a dose of 10 microg/mL.

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    • "Several authors have reported the presence of bioactives compounds such as polyphenol, alkaloids (Karou et al., 2005a,b) in the two plants. Other researchers have isolated 10 actives components (quindolinone, cryptolepinone, 11-methoxyquindoline, N-trans-feruloyltyramine, vomifoliol, loliolide , 4-ketopinoresinol, scopoletin, evofolin-A, and evofolin-B), along with five inactive compounds of known structure, ferulic acid, sinapic acid, syringic acid, (±)-syringaresinol, and vanillic acid in extract of S. acuta (Cao and Qi, 1993; Dinan et al., 2001; Jang et al., 2003). Three compounds kaempferol 1, quercetin 2, and 3-O-␤-d- (6 -O-trans-p-coumaroyl)-␣-l-glucopyranosyl-kaempferol 3 have been isolated in U. lobata (Adeloye et al., 2007). "
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    ABSTRACT: The potential antiproliferative and antioxidant activities of extracts from five medicinal plants from Cameroon were evaluated in vitro on HepG-2 cells. The results showed the significant decrease of the viability of the cells in a concentration-dependent manner. According to the IC50 obtained, the extracts of S. acuta (461.53±0.23) and U. lobata (454.93±0.12) showed significant antiproliferative activity. At fixed concentration (250�gmL−1), extracts demonstrated higher antiproliferative activity (67.05%; 65.42%), (52.62%; 56.64%) and (32.98%; 36.85%) respectively during 24, 48 and 72 h. Extracts of S. cordifolia and V. album demonstrated significant antiproliferative property after 48 h while S. rhombifolia exhibited weak cytotoxicity. The results of the antioxidant properties showed that theses extracts induced significantly increase of SOD, CAT and GsT activity after 48 h. Taken together, the results extracts showed that of S. acuta and U. lobata may be a promising alternative to synthetic substances as natural compound with high antiproliferative and antioxidant activities
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    • "Several authors have reported the presence of bioactives compounds such as polyphenol, alkaloids (Karou et al., 2005a,b) in the two plants. Other researchers have isolated 10 actives components (quindolinone, cryptolepinone, 11-methoxyquindoline, N-trans-feruloyltyramine, vomifoliol, loliolide , 4-ketopinoresinol, scopoletin, evofolin-A, and evofolin-B), along with five inactive compounds of known structure, ferulic acid, sinapic acid, syringic acid, (±)-syringaresinol, and vanillic acid in extract of S. acuta (Cao and Qi, 1993; Dinan et al., 2001; Jang et al., 2003). Three compounds kaempferol 1, quercetin 2, and 3-O-␤-d- (6 -O-trans-p-coumaroyl)-␣-l-glucopyranosyl-kaempferol 3 have been isolated in U. lobata (Adeloye et al., 2007). "
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    ABSTRACT: The potential antiproliferative and antioxidant activities of extracts from five medicinal plants from Cameroon were evaluated in vitro on HepG-2 cells. The results showed the significant decrease of the viability of the cells in a concentration-dependent manner. According to the IC(50) obtained, the extracts of S. acuta (461.53±0.23) and U. lobata (454.93±0.12) showed significant antiproliferative activity. At fixed concentration (250μgmL(-1)), extracts demonstrated higher antiproliferative activity (67.05%; 65.42%), (52.62%; 56.64%) and (32.98%; 36.85%) respectively during 24, 48 and 72h. Extracts of S. cordifolia and V. album demonstrated significant antiproliferative property after 48h while S. rhombifolia exhibited weak cytotoxicity. The results of the antioxidant properties showed that theses extracts induced significantly increase of SOD, CAT and GsT activity after 48h. Taken together, the results extracts showed that of S. acuta and U. lobata may be a promising alternative to synthetic substances as natural compound with high antiproliferative and antioxidant activities.
    05/2010; 29(3):223-8. DOI:10.1016/j.etap.2010.01.003
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    • "The plant has been screened for its cancer chemopreventive properties by Jang et al. (2003). The study resulted in the isolation of several compounds, among them quindolinone, cryptolepinone and 11- methoxyquindoline was found to induce quinone reductase activity, while cryptolepinone, Ntransferuloyltyramine exhibited a significant inhibition of 7, 12-dimethylbenz-[a]anthracene-induce preneoplastic lesions in mouse mammary organ culture model. "
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    ABSTRACT: Sida acuta is shrub belonging to Malvaceae family. The plant is widely distributed in the subtropical regions where it is found in bushes, in farms and around habitations. Surveys conducted in indigenous places revealed that the plant had many traditional usages that varied from one region to another. The most cited illnesses are fever, headache and infections diseases. Indeed, many laboratory screening have been conducted to show the scientific rationale behind these usages and many compounds have been isolated from the plant. In the present review we listed the plant usages in folk medicine in some regions where the plant grows and we discussed on the confirmed in vitro activities after laboratory screenings. The review ended with the pharmacological properties of several compounds isolated from S. acuta principally alkaloids.
    AFRICAN JOURNAL OF BIOTECHNOLOGY 01/2008; 625:2953-2959. · 0.57 Impact Factor
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