Cytotoxic Cardiac Glycoside Constituents of <i>Vallaris glabra</i> Leaves

Kruakaew, Sudarat; Seeka, Chonticha; Lhinhatrakool, Thitima; Thongnest, Sanit; Yahuafai, Jantana; Piyaviriyakul, Suratsawadee; Siripong, Pongpun; Sutthivaiyakit, Somyote

doi:10.1021/acs.jnatprod.7b00554

Cited by 14 publications

(17 citation statements)

References 15 publications

(48 reference statements)

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“… 34,35 Furthermore, observation of two pairs of related compounds 5/6, and 7/8 indicated that cardiac glycosides displayed weaker cytotoxicities with an increase in the number of sugar units. The sugar moiety is another factor while determining cytotoxic activity, 34 but the sugar moieties were less active than C-10 groups.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, OH-5 and OCOCH 3 -16 were the potential cytotoxic groups compared with these compounds, and the results were supported by the results given in the literature. 34,35 Furthermore, observation of two pairs of related compounds 5/6, and 7/8 indicated that cardiac glycosides displayed weaker cytotoxicities with an increase in the number of sugar units. The sugar moiety is another factor while determining cytotoxic activity, 34 but the sugar moieties were less active than C-10 groups.…”

Section: Cytotoxic Activities Of Compoundsmentioning

confidence: 99%

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Three new cardiac glycosides obtained from the roots ofStreblus asperLour. and their cytotoxic and melanogenesis-inhibitory activities

Miao

Zhang

et al. 2018

RSC Adv.

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Three new cardiac glycosides strophanthidin-3-O-a-L-rhamnopyranosyl-(1/4)-6-deoxy-b-Dallopyranoside (1), 5bH-16b-acetylkamaloside (2), and mansonin-19-carboxylic acid (3) along with seven known steroids including five cardiac glycosides were isolated from the methanol extracts of Streblus asper Lour. roots. The structures of these compounds were established by spectroscopic analyses. The cytotoxicities of crude extracts and all the isolated compounds were evaluated against four human cancer cell lines (HL60, A549, AZ521, and SKBR3). Furthermore, the selective index (SI) of each compound was measured by the ratio of cytotoxic effect on a normal cell line (WI38) to the cytotoxic effect on cancer cell line (A549). The results suggested that cardiac glycosides (2, 4, and 6-8) exhibited significant cytotoxicities with IC 50 values from 0.01 to 3.77 mM as well as high selective index for WI38/ A549 (SI 1.50-24.26), and they displayed superior selectivities when compared with the reference cisplatin (SI 1.09). Preliminary structure-activity relationships (SARs) were also discussed regarding the type of C-10 group in the cardiac glycosides being a crucial factor in determining the cytotoxic activities and regarding the sugar moieties having much less of an active role than the type of C-10 group. In addition, the melanogenesis-inhibitory abilities of these compounds were also evaluated. Cardiac

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Section: Resultsmentioning

confidence: 99%

Section: Cytotoxic Activities Of Compoundsmentioning

confidence: 99%

Three new cardiac glycosides obtained from the roots ofStreblus asperLour. and their cytotoxic and melanogenesis-inhibitory activities

Miao

Zhang

et al. 2018

RSC Adv.

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“…With IC50 values ranging from 0.03-0.07 µM, it showed significant cytotoxic action against the HTB38 cell line. [78] Crude saponins from fruits…”

Section: Vallaris Glabramentioning

confidence: 99%

Plant secondary metabolites for the prevention and treatment of colorectal cancer: A review

Raju¹,

Sekar²,

Kumar³

et al. 2022

J Pharmacogn Phytochem

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Colorectal cancer is becoming more common and deadly in both men and women nowadays. Although various treatment interventions are available including chemotherapy, surgery, radiation therapy and hormonal therapy, they are associated with some harmful effects. To avoid the risk factors associated with these therapies, natural products could be used as one of the most promising candidates for colorectal cancer. The natural products and their dietary supplements demonstrated stronger potential against various colorectal cancer cells. Flavonoids, phenolics, terpenoids, saponins, quinones, alkaloids, and other secondary metabolites are among the bioactive substances found in dietary supplements. These dietary phytochemicals exhibited strong and potent cytotoxicity against colorectal cancer cells which indicated their ability as chemopreventive agents. Both intrinsic and extrinsic routes were used to trigger apoptosis by the phytochemical substances. Phytochemicals influenced the cell cycle regulation, oncogenes, tumor markers and induced apoptosis by modulating tumor-suppressive miRNAs, affecting the cell signaling pathways, upregulating apoptotic inducers with the downregulation of anti-apoptotic proteins and factors. Thus, in this review, we addressed the sources and mechanism of various isolated phytochemicals as anti-colorectal cancer agents.

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“…Partially hydrogenated N-heterocycles (azolines), in particular 2-oxazolines, 2-thiazolines, and 2-imidazolines, are important synthetic targets, not only due to their abundance in biologically active compounds, [1][2][3][4][5][6][7] but also due to their high value as useful synthetic building blocks. [8][9][10][11][12][13] Enantiopure derivatives substituted either at C4, at C5, or at both saturated carbons are of particular importance due to the stereochemical requirements of the desired products or the chiral building blocks made by them. Enantiopure 4-oxazolines are also widely applied as core structural motifs, for example in chiral ligands for enantioselective transition metal-catalyzed reactions.…”

mentioning

confidence: 99%

“…Decreasing the catalyst loading to 5 mol% had a negative effect on the yield. Reduction of the reaction time or performing the reaction at 0 °C did not improve the enantioselectivity but only led to lower reaction rates and incomplete conversions (See entries [12][13].…”

mentioning

confidence: 99%

Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxazolines

Abazid¹,

Hollwedel²,

Nachtsheim

2021

Preprint

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This manuscript describes a highly enantioselective oxidative cyclization of N-Allyl Benzamides and derivatives thereof. This method uses a chiral triazole-based iodine catalyst to generate a hypervalent iodine compound in situ as the active catalytic species. Besides oxazolines, other N-heterocylces such as thiazolines, imidazolines as well as oxanines can be generated in high optical purities. <br>

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Cytotoxic Cardiac Glycoside Constituents of Vallaris glabra Leaves

Cited by 14 publications

References 15 publications

Three new cardiac glycosides obtained from the roots ofStreblus asperLour. and their cytotoxic and melanogenesis-inhibitory activities

Three new cardiac glycosides obtained from the roots ofStreblus asperLour. and their cytotoxic and melanogenesis-inhibitory activities

Plant secondary metabolites for the prevention and treatment of colorectal cancer: A review

Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxazolines

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