Antimycobacterial Cycloartanes from <i>Borrichia </i><i>frutescens</i>

Cantrell, Charles L.; Tong, L.; Fronczek, Frank R.; Fischer, Nikolaus H.; Adams, Linda B.; Franzblau, Scott G.

doi:10.1021/np960551w

Cited by 88 publications

(87 citation statements)

References 16 publications

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“…All of the isolates obtained from Q. majus along with 11 analogues were evaluated for their potential to inhibit the growth of M. tuberculosis and African green monkey Vero cells, respectively, according to established protocols (Collins and Franzblau, 1997;Cantrell et al, 1996). The results (Table I) showed that three common triterpenes, betulinic acid (1), oleanolic acid (4) and ursolic acid (6), along with the flavanone 5 exhibited significant inhibitory activity in a microplate alamar blue assay with MIC values of 62, 30, 31, and 90 µg/ml, respectively, while the other two isolates 2 and 3 were inactive (MIC > 128 µg/ml).…”

Section: Resultsmentioning

confidence: 99%

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Constituents of Quinchamalium majus with Potential Antitubercular Activity

Wang

Franzblau

et al. 2004

Zeitschrift Für Naturforschung C

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Antitubercular bioassay-guided fractionation of the dichloromethane extracts of the above-ground biomass and roots of Quinchamalium majus led to the identification of six known constituents, betulinic acid (1), daucosterol (2), 5,7-dihydroxyflavone (3), oleanolic acid (4), (Ð)-2S-pinocembrin (5), and ursolic acid (6), for the first time in this species. Their chemical structures were determined on the basis of spectroscopic evidence and chemical transformation methods. All of these compounds along with additional 11 analogues were evaluated for their antitubercular potential against Mycobacterium tuberculosis in a microplate alamar blue assay, and the primary structure-activity relationships (SARs) for 4 and 6 were discussed. In addition, all the isolates were tested for cytotoxicity against African green monkey Vero cells in order to evaluate for their selectivity potential.

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Section: Resultsmentioning

confidence: 99%

“…Evaluation of cytotoxicity of the CH 2 Cl 2 -soluble extract and pure compounds was performed as a modification of an established protocol (Cantrell et al, 1996). In brief, test compounds were dissolved at 10Ð40 mg/ml in DMSO.…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Constituents of Quinchamalium majus with Potential Antitubercular Activity

Wang

Franzblau

et al. 2004

Zeitschrift Für Naturforschung C

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“…16) After 72 h exposure, cell viability was measured using the CellTiter 96 aqueous non-radioactive cell proliferation assay. The IC 50 is defined as the reciprocal dilution resulting in 50% inhibition of the Vero cells.…”

Section: Methodsmentioning

confidence: 99%

Antitubercular Activity of Triterpenoids from Asteraceae Flowers

Akihisa

Franzblau

Ukiya

et al. 2005

Biological & Pharmaceutical Bulletin

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The flowers of Chrysanthemum morifolium RAMAT. and related chrysanthemum plants (Asteraceae) are used as a Chinese natural medicine. Florists Chrysanthemum Flower (Ju Hua) is prescribed for anti-inflammatory, analgesic, and antipyretic purposes and for the treatment of eye disease in Chinese traditional preparations. 1) In the course of our studies on bioactive principles of natural medicines and medicinal foodstuffs, we found that the triterpene alcohols isolated from the non-saponifiable lipid (NSL) fraction of the extract of chrysanthemum (C. morifolium RAMAT. var. sinense MAKINO forma esculentum MAKINO; Japanese name: Ryourigiku) and other Asteraceae plants (pot marigold, cosmos, sunflower, burdock, etc.) possess remarkable anti-inflammatory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema in mice, [2][3][4][5] inhibitory effects on trypsin and chymotrypsin, 6) anti-tumor promoting effects, [7][8][9] and cytotoxic activity against human cancer cell lines. 7) Various types of triterpenoids from plants have recently been reported to exhibit antitubercular activity. 10,11) In this paper, we describe the antitubercular activity against Mycobacterium tuberculosis of twenty-nine 3-hydroxy triterpenoids: twentyeight (1-16, 18-29) were isolated from the NSL fraction of the extract of chrysanthemum flowers and one (17) was chemically derived from compound 16. MATERIALS AND METHODSChemicals Twenty-seven triterpenoids (1-16, 18-26, 28, 29) (Chart 1) were isolated from the NSL fraction of the methanol extract of chrysanthemum flowers.2,3,5) Triterpenoid 27, which had previously been isolated from the extract of sunflower pollen, 12) was isolated from the NSL fraction of the methanol extract of chrysanthemum flower, 13) and triterpenoid 17 was prepared from 16 by oxidation with CrO 3 -pyridine followed by NaBH 4 reduction of the oxidation product. 14)Determination of Antitubercular Activity Antitubercular activity of compounds in DMSO was determined against Mycobacterium tuberculosis H 37 Rv (ATCC 27294) in Middlebrook 7H12 medium using the Microplate Alamar Blue Assay (MABA) as previously described.15) The MIC is defined as the lowest concentration effecting a reduction in fluorescence of 90% relative to controls.Cytotoxicity Assay Toxicity against Vero cells (ATCC CCL-81) was determined as described earlier.16) After 72 h exposure, cell viability was measured using the CellTiter 96 aqueous non-radioactive cell proliferation assay. The IC 50 is defined as the reciprocal dilution resulting in 50% inhibition of the Vero cells. RESULTS AND DISCUSSIONThe MIC values of 1-29 against M. tuberculosis are shown in Table 1. Among the compounds tested, fifteen of them: five taraxastanes (2, 4-7), two oleananes (9, 11), two ursanes (13, 15), two lupanes (17, 18), two cycloartanes (22, 24), one tirucallane (27), and one dammarane (29), exhibited activity with MIC values of 4-64 mg/ml, among which maniladiol (9; MIC 4 mg/ml) and 3-epilupeol (17; 4 mg/ml) followed by 4,5a-epoxyhelianol (27; 6 mg/ml) showed the ...

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“…Caldwell and coworkers showed that OA isolated from Argentinean shrub, Junella tridens (Verbanaceae) was active against M. tuberculosis H37Rv [36]. The MIC of OA determined using a BACTEC radiospirometric assay [37] was 50 mg mL -1 (Table 1). OA-derivatives, oleanonic acid and 3-epi-oleanonc acid, were three-fold more active.…”

Section: Antibacterial Activity Of Oa and Its Derivativesmentioning

confidence: 99%

Antibacterial activity of oleanolic and ursolic acids and their derivatives

et al. 2010

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Bacterial resistance to antibiotics is increasing at an alarming rate and many commonly used antibiotics are no longer effective.Thus, there is considerable interest in investigating novel antibacterial compounds, such as the plant-derived pentacyclic triterpenoids, including oleanolic acid (OA), ursolic acid (UA) and their derivatives. These compounds can be isolated from many medicinal and crop plants and their antibacterial, antiviral, antiulcer and anti-inflammatory effects are well documented. OA and UA are active against many bacterial species, particularly Gram-positive species, including mycobacteria. They inhibit bacterial growth and survival, and the spectrum of minimal inhibitory concentration (MIC) values is very broad. In addition, OA, UA and their derivatives display potent antimutagenic activity. Studies to identify the cellular targets and molecular mechanisms of OA and UA action were initiated a few years ago and it has already been demonstrated that both acids influence bacterial gene expression, the formation and maintenance of biofilms, cell autolysis and peptidoglycan turnover. Before these compounds can be used clinically as antimicrobial agents, further extensive studies are required to determine their cytotoxicity and the optimum mode of their application.

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Antimycobacterial Cycloartanes from Borrichia frutescens

Cited by 88 publications

References 16 publications

Constituents of Quinchamalium majus with Potential Antitubercular Activity

Constituents of Quinchamalium majus with Potential Antitubercular Activity

Antitubercular Activity of Triterpenoids from Asteraceae Flowers

Antibacterial activity of oleanolic and ursolic acids and their derivatives

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