Structure elucidation by NMR spectroscopy of a new acetylated saponin from Centratherum anthelminticum

Mehta, B. K.; Mehta, Darshana; Itoriya, Amrita

doi:10.1016/j.carres.2004.10.001

Cited by 10 publications

(7 citation statements)

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“…Centratherum anthelminticum (L.) KUNTZE (family: Asteraceae) is an erect, pubescent annual herb found widely in the Indian subcontinent which is locally known as “Somraj,” and its seeds are known as “Kalijiri” in Hindi [5, 6]; scientific synonyms for this plant include Vernonia anthelmintica and Conyza anthelmintica , among others. This plant is used extensively in Ayurveda for the treatment of cough and diarrhoea, as well as an anthelmintic, stomachic, diuretic, and antiphlegmatic agent [5, 7].…”

Section: Introductionmentioning

confidence: 99%

“…This plant is used extensively in Ayurveda for the treatment of cough and diarrhoea, as well as an anthelmintic, stomachic, diuretic, and antiphlegmatic agent [5, 7]. Experimental studies proved the pharmacological effects of this plant's seeds extract, including antihelminthic [8], larvicidal [9], antipyretic [10], antifilarial [11], antihyperglycemic [12], antimicrobial [13], and diuretic [14] activities.…”

Section: Introductionmentioning

confidence: 99%

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Chloroform Fraction ofCentratherum anthelminticum(L.) Seed Inhibits Tumor Necrosis Factor Alpha and Exhibits Pleotropic Bioactivities: Inhibitory Role in Human Tumor Cells

Arya

Achoui

Cheah

et al. 2012

Evidence-Based Complementary and Alternative Medicine

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We investigated the antioxidant potential, cytotoxic effect, and TNF-α inhibition activity with NF-κB activation response in a chloroform fraction ofCentratherum anthelminticumseeds (CACF). The antioxidant property of CACF was evaluated with DPPH, ORAC, and FRAP assays, which demonstrated significant antioxidant activity. The cytotoxicity of CACF was tested using the MTT assay; CACF effective inhibitory concentrations (IC50) for A549, PC-3, MCF-7, and WRL-68 cells were31.42±5.4,22.61±1.7,8.1±0.9, and54.93±8.3 μg/mL, respectively. CACF effectively and dose-dependently inhibited TNF-α release,in vitroandin vivo. CACF inhibited TNF-α secretion in stimulated RAW264.7 macrophage supernatants with an IC50of 0.012 μg/mL, without affecting their viability; the highest dose tested reduced serum TNF-α by 61%. Acute toxicity testing in rats revealed that CACF was non-toxic at all doses tested. Matching the cytotoxic activity towards a mechanistic approach, CACF dose-dependently exhibitedin vitroinhibitory effects against the activation of NF-κB translocation in MCF-7 cells. Preliminary phytochemical screening with GC/MS analysis detected 22 compounds in CACF, of which morpholinoethyl isothiocyanate was the most abundant (29.04%). The study reveals the potential of CACF in the treatment of breast cancer and in oxidative stress conditions with associated inflammatory responses.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chloroform Fraction ofCentratherum anthelminticum(L.) Seed Inhibits Tumor Necrosis Factor Alpha and Exhibits Pleotropic Bioactivities: Inhibitory Role in Human Tumor Cells

Arya

Achoui

Cheah

et al. 2012

Evidence-Based Complementary and Alternative Medicine

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“…The signals of the aglycone's C-12 and C-13 at δ 122.0 and δ 144.0, respectively show the presence of two olefinic carbons (Mehta et al, 2004;Xu et al, 2010) and a signal at δ 178.6 (C-28) which shows the presence of a carboxylic acid at that position, thus, confirming that the aglycone is of olean-12-ene skeleton and therefore olean-12-en-28-oic acid aglycone.…”

Section: Resultsmentioning

confidence: 66%

“…Compound 3 (Figure 3) was also isolated as a brownish amorphous powder and its molecular formula was determined as 68, 0.74, 0.85, 0.86, 0.87, 0.93 and 1.07 which is a characteristic of a typical oleanane type triterpene acid, an oxymethine at δ 3.01 and olefinic protons at δ 5.17 indicating that the aglycone is of olean -12-ene skeleton and therefore olean-12-en-28-oic acid aglycone (Mehta et al, 2004;Xu et al, 2010). It also displayed five anomeric proton signals at δ 4.31, 4.27, 5.21/5.33, 4.69 and 5.04 signifying the presence of five sugar units.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial saponins from the leaves of Polyscias fulva (Araliaceae)

Maritim¹,

Wagara²,

Matasyoh³

2019

Afr. J. Biotechnol.

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Saponins are a major family of secondary metabolites that occur in a wide range of plant species. Bioassay-guided fractionation of extract of the leaves of Polyscias fulva led to the isolation of three known saponins named, 3-O-α-L-arabinopyranosyl-hederagenin (1), 3-O-[α-L-rhamnopyranosyl(1-2)-α-Larabinopyranosyl]-hederagenin (2) and 3-O-[rhamnopyranosyl-(1→2)-xylopyranosyl]-Olean-12-en-28-O-[rhamnopyranosyl-(1→4)-glucopyranosyl-(1→6-glucopyranosyl] ester) (3). Leaves of the plant were collected from Kakamega rain forest in Kenya, dried under shade and ground into fine powder and extraction was done using methanol. The methanol extract was subjected to column chromatography and the fractions purified using preparative high performance liquid chromatography (HPLC). The bioactivity of the pure compounds was done using disc diffusion method. The three compounds exhibited moderate activities against Gram positive bacterium (Staphylococcus aureus ATCC25922) and Gram negative bacterium (Klebsiella pneumoniae ATCC13883). Compound 1 was found to be the most active against K. pneumoniae (8.00±1.00 mm) and S. aureus (10.00±1.73 mm) followed by compound 2 with inhibition zones of 7.66±0.57 and 7.33±0.57 mm against K. pneumoniae and S. aureus, respectively. Compound 3 was the least active against both K. pneumoniae (7.33±0.57 mm) and S. aureus (7.00±1.00 mm). The results obtained indicate that compounds 1, 2 and 3 exhibit potential as possible sources of antibacterial agents.

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“…Singh, Pandey, L. Singh, & Sen, 1981;Scott & Krewson, 1965). Earlier phytochemical investigations revealed that the seeds of plant contain aliphatic fatty acids, steroids and glycosides (Mehta, Mehta, & Itoria, 2004a;Mehta, Verma, Kotra, & Jafari, 2004b;Mehta, Verma, & Mehta, 2005). In the present study, we report on the isolation and characterisation of two novel compounds:…”

Section: Introductionmentioning

confidence: 79%

Isolation and structure determination of acetylated triterpenoid saponins from the seeds ofCentratherum anthelminticum

Mehta

Itoriya

2010

Natural Product Research

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Phytochemical investigation of Centratherum anthelminticum seeds resulted in the isolation of two novel glycosides. The pentacyclic triterpenoid saponins were shown to contain hederagenin and sugar residues forming two glycosyl chains. The structural analysis of its acetylated derivative was determined using a combination of homo- (1D 1H NMR, 13C NMR and 13C NMR-DEPT) and heteronuclear 2D NMR techniques (1H-1H-COSY, total correlated spectroscopy (TOCSY), heteronuclear multiple quantum coherence (HMQC)), heteronuclear multiple bond correlation (HMBC) and chemical methods. The structure of the saponins were established to be 3-O-[beta-D-glucopyranosyl-(1 --> 2)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-glucopyranosyl]-23-hydroxyolean-12-en-28-oic acid and 3-O-[beta-D-glucopyranosyl-(1 --> 2)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucoyranosyl-(1 --> 3)-beta-D-glucopyranosyl]-23-hydroxyolean-12-en-28-oic acid. Different extracts and compounds were also tested for antifilarial and antimicrobial activities. Methanolic, acetone and aqueous extracts of seeds exhibited some pronounced pharmacological activity under study.

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Structure elucidation by NMR spectroscopy of a new acetylated saponin from Centratherum anthelminticum

Cited by 10 publications

References 9 publications

Chloroform Fraction ofCentratherum anthelminticum(L.) Seed Inhibits Tumor Necrosis Factor Alpha and Exhibits Pleotropic Bioactivities: Inhibitory Role in Human Tumor Cells

Chloroform Fraction ofCentratherum anthelminticum(L.) Seed Inhibits Tumor Necrosis Factor Alpha and Exhibits Pleotropic Bioactivities: Inhibitory Role in Human Tumor Cells

Antibacterial saponins from the leaves of Polyscias fulva (Araliaceae)

Isolation and structure determination of acetylated triterpenoid saponins from the seeds ofCentratherum anthelminticum

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