Triterpenoids

Connolly, Joseph D.; Hill, Robert A.

doi:10.1039/b204068a

Cited by 36 publications

(15 citation statements)

References 131 publications

(141 reference statements)

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“…Triterpenoids constitute a large number of natural products,25, 26 including those with carboxyl groups as well as various esters27 that in principle can be hydrolyzed in vivo to the free aryl carboxylic acid 11. Many of these triterpernoids are biologically active compounds that include anticancer and antiviral activities 26.…”

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confidence: 99%

Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs

Scott

Chen

Daniel

et al. 2011

Bioorganic & Medicinal Chemistry Letters

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Shp2 protein tyrosine phosphate (PTP) is a novel target for anticancer drug discovery. We identified estramustine phosphate as a Shp2 PTP inhibitor from the National Cancer Institute Approved Oncology Drug set. A focused structure-activity relationship study indicated that the 17-phosphate group is required for the Shp2 PTP inhibitor activity of estramustine phosphate. A search for estramustine phosphate analogs led to identification of two triperpenoids, enoxolone and celastrol, having Shp2 PTP inhibitor activity. With the previously reported PTP1B inhibitor trodusquemine, our study reveals steroids and triterpenoids with negatively charged phosphate, carboxylate, or sulfonate groups as novel pharmacophores of selective PTP inhibitors. KeywordsShp2; Protein tyrosine phosphatase; Estramustine phosphate; Enoxolone; Celastrol; Triterpenoids Protein tyrosine phosphorylation is a major signaling mechanism that controls cellular activities pertinent to cancer initiation and progression. Protein tyrosine phosphorylation is coordinately regulated by protein tyrosine kinases (PTKs) and protein tyrosine phosphatases (PTPs). While many PTKs have well-demonstrated roles in human cancer and are validated targets of anticancer drugs, increasing evidence also shows that a number of PTPs, such as

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confidence: 99%

Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs

Scott

Chen

Daniel

et al. 2011

Bioorganic & Medicinal Chemistry Letters

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“…2) allowed us to assemble the structure of 1 to be a new pentacyclic triterpenoid, urs-12-en-29α-oic acid-3β-ol. 1 has the same skeleton with ursane [3]. The major differences identified were one methyl group connecting to C-19 in ursane, with the carboxylic group connecting to C-19 and the hydroxyl group linking to C-3 in 1.…”

Section: Resultsmentioning

confidence: 94%

New bioactive triterpenoid from Oldenlandia cantonensis How

Lan

2007

Front. Chem. China

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A new pentacyclic triterpenoid, urs-12-en-29α-oic acid-3β-ol (1), was obtained from the ethanol extract of Chinese herb Oldenlandia cantonensis How. The structure was elucidated by spectroscopy methods, including nuclear magnetic resonance (NMR) (1D and 2D), infrared spectroscopy (IR), and mass spectrometry (MS). 1 exhibited significant inhibitory activity against the human DNA topoisomerase I (hTopo I), the cancer cell lines BEL-7402 and MCG-803, with the IC 50 values 12.0, 6.5, and 8.0 µg/mL, respectively. The volatile oil, the fraction of petroleum ether: EtOAc = 20:1 (V/V ) on Si gel chromatography, was also quantitatively analyzed by gas chromatography mass spectrometry (GC-MS). As a result, 60 compounds were identified. Among them, the long chain aliphatics, terpenes and steroids, as the representative structure type, were found with percentages of 36.16%, 6.42% and 9.28%, respectively.

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“…To determine the connectivity of the functional group in compound 1, 1 H-1 H COSY and HMBC experiments were conducted, and the results are shown in Figure 2. The 1 H-1 H COSY spectrum of 1 showed connectivity in H1-H2-H3, H5-H6-H7, H11-H12, H15-H16-H17 and H20-H22-H23-H24, indicating the presence of lanostane-type (Connolly and Hill, 2003). In the HMBC spectrum, the connectivity arising from the tertiary methyl protons to their attached carbons enabled the determine of the five primary methyls at C-4, C-10, C-14, C-15, and C-25, respectively.…”

Section: Resultsmentioning

confidence: 98%

Triterpenoids from The Bark of Garcinia porecta and their Cytotoxic Activity against MCF7 Breast Cancer Lines

et al. 2019

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The Garcinia genus is a well known tropical plant in the Indo-Malesiana region and mainly distributed in tropical countries including Indonesia, Thailand, and Malaysia. Previous phytochemical studies on Garcinia species have led to the identification and isolation of mainly prenylated xanthones. This research describes the isolation and structure elucidation of isolated triterpenoids compounds from the bark of Garcinia porecta. Dried powder bark of G. porecta was extracted with methanol and then partitioned with n-hexane, ethyl acetate, and n-butanol. The n-hexane extract then was separated and purified with chromatography techniques to obtain isolated compounds 1 and 2. The chemical structure of isolated compounds was elucidated by spectroscopic methods including one and two-dimensional NMR as well as high-resolution mass spectrometric analysis and identified as lanosterol (1) dan arabidiol (2), respectively. These triterpenoids were isolated from this plant for the first time. Compound 1 and 2 showed weak cytotoxic activity against MCF-7 breast cancer cells with IC50 values of 60.09 dan 46.17 µM, respectively.

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Triterpenoids

Cited by 36 publications

References 131 publications

Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs

Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs

New bioactive triterpenoid from Oldenlandia cantonensis How

Triterpenoids from The Bark of Garcinia porecta and their Cytotoxic Activity against MCF7 Breast Cancer Lines

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