Two New Macrolide Sesquiterpene Pyridine Alkaloids from Maytenus emarginata: Emarginatine G and the Cytotoxic Emarginatine F

Kuo, Yao‐Haur; King, Ming-Lu; Chen, Chia–Fu; Chen, Haur-Young; Chen, Chung‐Hsiung; Chen, Ke; Lee, Kuo‐Hsiung

doi:10.1021/np50104a011

Cited by 76 publications

(41 citation statements)

References 3 publications

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“…HSQC and HMBC data further supported the assignment of the 2,3-disubstituted pyridine unit (Supplemental Table 1). A dicarboxy side chain containing two esters, one methine, two methylenes, one ethyl group, and the 2,3-disubstituted pyridine unit supported the presence of a cassininic acid moiety in oppositine A (1). The NMR data for this portion of the molecule are consistent with data reported for the analogous protons in the compounds cassinine 13 and orthophosphonine.…”

supporting

confidence: 79%

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

et al. 2006

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Two new sesquiterpene pyridine alkaloids, oppositines A (1) and B (2), have been isolated from the plant, Pleurostylia opposita (Celastraceae), collected in Sri Lanka. The compounds were isolated and purified by solvent/solvent partitioning, column chromatography and HPLC. Their structures were assigned on the basis of extensive 1D and 2D NMR studies as well as analysis by HRESIMS. Oppositines A (1) and B (2) showed moderate cytotoxicity against HCT116 cell lines with EC 50 values of 27 ± 2 and 26 ± 3 μM, respectively.Poly-acetylated sesquiterpene pyridine alkaloids are ubiquitously found in the Celastraceae family of plants. 1-4 Dihydro-β-agarofuran sesquiterpenes frequently incorporate pyridine dicarboxylic acids to bridge their sesquiterpenoid cores at the C-3 and C-13 positions. The dihydro-β-agarofuran skeleton is comprised of a decalin ring, a tetrahydrofuran ring, and methyl substituents located at the C-4, C-10, and two at the C-11 position. Evoninic, wilfordic, edulic, cathaic, and cassininic (often misnamed cassinic) acids are some of the pyridine carboxylic acids present in this class of sesquiterpenes. These compounds are of interest due to their wide range of biological activities including: cytotoxicity, 1 immunosuppression, 2 insecticidal, 3,5,6 insect-antifeedant, 5,7 anti-HIV, 4 reversal of the multidrug resistance (MDR) phenotype, 8-11 and antitumor. 12 As part of an ongoing search for bioactive compounds, two new sesquiterpene alkaloids, oppositines A (1) and B (2), were isolated from the Sri Lankan plant, Pleurostylia opposita (Wallich, 1824) (Celastraceae).The air dried stem bark of P. opposita was extracted with 1:1 MeOH/CH 2 Cl 2 . The extract was dried and partitioned between petroleum ether and aqueous MeOH, and the aqueous MeOH was subsequently partitioned with chloroform. The chloroform-soluble material was fractionated using size exclusion chromatography, preparative TLC, and reversed-phase HPLC resulting in oppositines A (1) and B (2).

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confidence: 79%

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

et al. 2006

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“…Kuo (1994) isolated two sesquiterpenes from M. emarginata namely 'emarginatine F' and . Each data point represents the mean of data from three wells (n = 3).…”

Section: Discussionmentioning

confidence: 99%

Growth inhibition and induction of apoptosis in human cancerous HeLa cells by Maytenus procumbens

Momtaz¹,

Hussein²,

Ostad³

et al. 2013

Food and Chemical Toxicology

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The possible biochemical activities of the acetonic/ethanolic extract of the leaves of Maytenus procumbens (L.M.P), and its isolated compounds were investigated in the present study. In cytotoxicity assay, L.M.P showed IC 50 of 68.79, 51.22, 78.49, 76.59, and 76.64 µg/ml on Caco-2, HeLa, HT29, NIH3T3, and T47D cells, respectively. Bioassay guided fractionation led to the isolation and identification of a new triterpene: '30-hydroxy-11α-methoxy-18β-olean-12-en-3-one' (HMO) in addition to a known terpenoid: 'asiatic acid' (AA). HMO exhibited the most cytotoxicity against HeLa cells and was further investigated for its ability to induce apoptosis in MTT, Annexin V-fluorescein isothiocyanate; Annexin V-FITC, propidium iodide; PI, radical scavenging capacity; RSC, 1,2-diphenyl-2-picrylhydrazyl; DPPH, ferric-reducing antioxidant power; FRAP, thiobarbituric acid reactive substance; TBARS, reactive oxygen species; ROS, 2,7-dichlorofluorescin diacetate; DCFH-DA.

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“…The authors also have identified cytotoxic sesquiterpene pyridine alkaloids, including emarginatines B (I7) and F (I8), from M. emarginata (Willd.) Ding Hou (90,91). Recently, new triterpenes were isolated from M. chuchuhuasca R. Hamet and Colas (92), along with sesquiterpenes from the same plant (93).…”

Section: Maytenus Speciesmentioning

confidence: 99%

Plant‐Derived Natural Products Research in Drug Discovery

Lee

Itokawa

Akiyama

et al. 2012

Natural Products in Chemical Biology

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Two New Macrolide Sesquiterpene Pyridine Alkaloids from Maytenus emarginata: Emarginatine G and the Cytotoxic Emarginatine F

Cited by 76 publications

References 3 publications

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

Growth inhibition and induction of apoptosis in human cancerous HeLa cells by Maytenus procumbens

Plant‐Derived Natural Products Research in Drug Discovery

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