Triterpenes from Rhus taitensis

Yürüker, Ayşen; Orjala, Jimmy; Sticher, Otto; Rali, Topul

doi:10.1016/s0031-9422(97)00901-1

Cited by 30 publications

(22 citation statements)

References 12 publications

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“…3 β ,22,25–Trihydroxylupane: NMR data matched those previously published 6. HRESIMS m/z 483.3801 [M + Na] + , calcd for C 30 H 52 O 3 Na 483.3814.…”

Section: Methodssupporting

confidence: 80%

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Tetrahdroxysqualene from Rhus taitensis Shows Antimycobacterial Activity against Mycobacterium tuberculosis

et al. 2008

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Tuberculosis has become a major health problem, in particular with the emergence of extremely drug resistant tuberculosis (XDRTB). In our search for new therapeutic leads against TB, we isolated a new triterpene (1) from the plant Rhus taitensis collected in Papua New Guinea. Tetrahydroxysqualene (1) was isolated using bioassay-guided fractionation of the methanolic extract of R. taitensis leaves and twigs. The structure of tetrahydroxysqualene (1) was elucidated on the basis of HRESIMS and 1D and 2D NMR spectra. Tetrahydroxysqualene (1) exhibited anti-tuberculosis activity with an MIC of 10.0 μg/mL while showing only modest cytotoxicity.Tuberculosis, caused by the bacterial pathogen Mycobacterium tuberculosis, has become a major global health threat, especially in developing nations.1 TB therapy requires long treatment regimens and patient compliance is difficult, 2 and failure of patients to comply with therapy has led to the emergence of multi drug resistant TB (MDRTB) and extremely drug resistant TB (XDRTB). 2, 3 There is an ever-growing need for new therapeutics for treatment of TB, especially for HIV/TB patients.4Over the past decades, natural products have played an important role as sources of secondary metabolites with potential as lead compounds for drug discovery. 5 In our effort to discover new therapeutic leads against TB, we screened a natural products library constructed of plant extract fractions from Papua New Guinea plants. Plant extracts were fractionated on HP20SS, which is a reversed-phase polystyrene-based adsorbent (See Experimental). The subsequent fractions were formatted into 96-well plates for screening. After screening the HP20SS library, we identified a TB inhibitory HP20SS fraction from Rhus taitensis Guill. (Anacardiaceae). A large scale extraction and bioassay-guided fractionation yielded one new triterpene, tetrahydroxysqualene (1) as the active component and the known 3β,22,25-trihydroxylupane. 6 The latter was not active against TB.The genus Rhus, also known by the common name sumac, contains over 250 described species of flowering plants, and the biological activities of Rhus spp. extracts have recently been reviewed. 7,8 More recent reports include detailed studies on the anti-HIV activity of

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“…3 β ,22,25–Trihydroxylupane: NMR data matched those previously published 6. HRESIMS m/z 483.3801 [M + Na] + , calcd for C 30 H 52 O 3 Na 483.3814.…”

Section: Methodssupporting

confidence: 80%

“…(Anacardiaceae). A large scale extraction and bioassay-guided fractionation yielded one new triterpene, tetrahydroxysqualene (1) as the active component and the known 3 β ,22,25-trihydroxylupane 6. The latter was not active against TB.…”

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confidence: 99%

Tetrahdroxysqualene from Rhus taitensis Shows Antimycobacterial Activity against Mycobacterium tuberculosis

et al. 2008

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“…More targeted studies on non-phenolic phytochemicals in sumac have isolated and structurally characterized the following compounds: 3α,20-dihydroxy-3β,25-epoxylupane (2) from the flowers of R. typhina [20]; allobutulin, α-/β-amyrin, campesterol, lupeol, and β-sitosterol from R. typhina leaves and branches [21]; rhuslactone (3) [22] and semialatic acid (4), semialactone (5), isofouquierone peroxide (6), and fouquierone (7) from the bark of R. javanica [23]; 2, 3β,20,25-trihydroxylupane (8), 3,25-diacetyl-3β,20,25-trihydroxylupane (9), 3β,20-dihydroxylupane (10), 20-hydroxylupane-3-one (11), and 20,28-dihydroxylupane-3-one (12) from the leaves of R. taitensis [24] and campesterol from R. thyrsiflora leaves [25]. Only two studies have investigated non-phenolic compounds from R. semialata, and the works involved isolation of just three compounds.…”

Section: Phytochemicals In Essential Oils and Non-polar Extractables mentioning

confidence: 99%

Chemical Profiles of Essential Oils and Non-Polar Extractables from Sumac (Rhus spp.)

Rayne¹

2011

Nature Precedings

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Sumac is the common name for a genus (Rhus) with >250 individual species of flowering plants in the family Anacardiaceae. These plants are globally distributed in temperate and tropical regions and can grow on marginal lands, making them strong candidates for renewable bioproduct sources. Despite the extensive historical use of some members of Rhus spp. for tannins and other commercial phenolics, little is known about the non-phenolic components of extracts and essentials oils. The current review highlights opportunities available to extend these limited prior studies to other sumac species, and for obtaining value-added compounds to complement already established phenolic extractions in these commercial plant species. To date, a number of individual aldehydes, fatty acids, long chain alcohols, terpenes and terpenoids, and waxes of commercial or bioactive potential in essential oils and non-polar extractables from selected members of the Rhus genera have been identified. Additional studies are needed to broaden the phytochemical database from other sumac species, and to better quantify the potential yields of these valuable compounds from the plants under natural and agriculturally managed conditions.

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“…Among the above described constituents, the stearic and eicosanoic acid esters of arnidiol (3, 4), and 16b-hydroxylupeol (11,12), and the eicosanoic ester of maniladiol (8) are new natural products. All the other corresponding esters had been described only with 1 H-NMR, [14][15][16] and their a) Compounds 1, 3 and 4 showed similar NMR data to that of 2 except for the alkyl chain moiety of the fatty acid residue.…”

Section: )mentioning

confidence: 99%