Selective Cytotoxicity of Ginkgetin from <i>Selaginella moellendorffii</i>

Sun, Changming; Syu, Wan-Jr; Huang, Yi-Tsau; Chen, Chien-Chih; Ou, Jun-Chih

doi:10.1021/np960608e

Cited by 91 publications

(68 citation statements)

References 22 publications

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“…11,12 Moreover, many studies have suggested that flavonoids exhibit important cancer chemoprevention [13][14][15][16] and anticancer activities. [17][18][19] Focusing on the anti-cancer properties of chemical constituents from Brazilian plants we have assayed the cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia cells of a glicoalkaloid fraction (GB), the flavonoid tiliroside (1), solasonine (2) and peracethyl solasonine (2a) from Solanum crinitum Lam and the aglicone solasodine (3) from S. jabrense. We report here our latest results.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia of alkaloids and flavonoid from two Solanum Species

Esteves-Souza¹,

Silva²,

Alves³

et al. 2002

J. Braz. Chem. Soc.

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Diversas espécies do gênero Solanum apresentam glicoalcalóides e flavonóides com grande variedade de atividades biológicas. O flavonóide tiliroside (1), uma fração rica em glicoalcalóides denominada GB e o glicoalcalóide solasonina (2) foram obtidos dos tricomas de galhos jovens e frutos de Solanum crinitum Lam e o alcalóide estereoidal solasodina (3), extraído das partes aéreas de S. jabrense Agra & M. Nee, tiveram sua atividade citotóxica avaliada frente a células do carcinoma de Ehrlich e da leucemia humana K562. O efeito antiproliferativo destas substâncias mostrou comportamento dose-dependente após avaliação através do método do MTT, para ambos os casos. Os resultados indicaram atividade citotóxica para 1, GB e 2, com IC 50 = 69,50 µM, 19,5 µg mL -1 e 74,20 µM, respectivamente, quando ensaiadas frente ao carcinoma de Ehrlich, e IC 50 = 118,40 µM, 13,65 µg mL -1 , 60,35 µM e 76,92 µM para 1, GB, 2 e 2a (derivado peracetilado da solasonina) frente a leucemia K562. A baixa atividade da aglicona solasodina (3) indicou a importância da presença dos açúcares na estrutura do glicoalcalóide e permitiu postular a substância 2, presente na fração rica em glicoalcalóides (GB), como um dos principios ativos. Além disso, os resultados mostraram a possibilidade de biomonitoramento através do ensaio do MTT na busca de metabólitos com atividade citotóxica.Steroidal alkaloids, flavonoids and their glycosides occurring in numerous species of Solanum genus are known to possess a variety of biological activities. The flavonoid tiriloside (1), a rich in glycoalkaloids total fraction named GB and the glycoalkaloid solasonine (2) isolated from thricomes of young branches and fruits from Solanum crinitum Lam, and the aglycone solasodine (3) isolated from Solanum jabrense Agra & M. Nee, were assayed against murine Ehrlich carcinoma and human K562 leukaemia cultured cells. The exposure in vitro of these cancer cells to these products resulted in a dose-dependent growth inhibition evaluated by the MTT method. The results indicated significant cytotoxic activities with IC 50 = 69.50 µM, 19.5 µg mL -1 , and 74.20 µM for 1, GB and 2, respectively, against Ehrlich carcinoma, and IC 50 = 186.50 µM, 13.65 µg mL -1 and 76.92 µM, for 1, GB, 2 and 2a, respectively, against K562 leukaemia cells. The low activity of the aglycone 3 indicates that the role of the sugar moiety is very important in the cytotoxic activity of glycoalkaloid solsonine. The cytotoxic activity revealed by the GB fraction may be attributed to the presence of 2. Additionally, these results show the viability of the MTT assay for monitoring phytochemical bioactive compounds. K562 Leukaemia Vol. 13, No. 6, 2002 Kolaviron for the treatment of various diseases, including hepatitis and laryngitis, 3 and several Leguminosae plants containing isoflavonoids with potent estrogenic activity. 4 Many plants in the Solanaceae family accumulate steroidal alkaloids based on a C 27 cholestane skeleton, e.g. solasodine and tomatidine. These compounds are essentially nitrogen analogues...

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Section: Introductionmentioning

confidence: 99%

Cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia of alkaloids and flavonoid from two Solanum Species

Esteves-Souza¹,

Silva²,

Alves³

et al. 2002

J. Braz. Chem. Soc.

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“…All experiments were carried out at least three times and they gave similar results. The inhibitory activities of ochnaflavone (4) and wogonin (reference compound) on COX-2 catalyzed PGE 2 production from LPS-activated RAW 264.7 cells were estimated. Ochnaflavone exhibited quite strong inhibitory activity (IC 50 = 1.08 μM) on COX-2 catalyzed PGE 2 production from LPS-activated RAW 264.7 cells.…”

Section: Resultsmentioning

confidence: 99%

“…Previously, certain biflavonoids were reported to inhibit phosphodiesterase, 1 lens aldose reductase, 2 mast cell histamine release 3 and to show anticancer activity. 4 Recently, some C-C and C-O-C biflavonoids were synthesized and their anti-microbial 5 and anti-inflammatory 6,7 activities were demonstrated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Ochnaflavone and Its Inhibitory Activity on PGE₂Production

Kim¹,

Vo²,

Park

2014

Bulletin of the Korean Chemical Society

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Ochnaflavone, a naturally occurring biflavonoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a C-O-C linkage, was first synthesized and evaluated its inhibitory activity on PGE2 production. Total synthesis was accomplished through modified Ullmann diaryl ether formation as a key step. Coupling reactions of 4'-halogenoflavones and 3'-hydroxy-5,7,4'-trimethoxyflavone were explored in diverse reaction conditions. The reaction of 4'-fluoro-5,7-dimethoxyflavone (2c) and 3 '-hydroxy-5,7,4'-trimethoxyflavone (2d) in N,N-dimethylacetamide gave the coupled compound 3 in 58% yield. Synthetic ochnaflavone strongly inhibited PGE2 production (IC50 = 1.08 µM) from LPS-activated RAW 264.7 cells, which was due to reduced expression of COX-2. On the contrary, the inhibition mechanism of wogonin was somewhat different from that of ochnaflavone although wogonin, a natural occurring anti-inflammatory flavonoid, showed strong inhibitory activity of PGE2 production (IC50 = 0.52 µM), and seems to be COX-2 enzyme inhibition. Our concise total synthesis of ochnaflavone enable us to provide sufficient quantities of material for advanced biological studies as well as to efficiently prepare derivatives for structure-activity relationship study.

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“…show notable anti-cancer properties (Lai et al, 2010). The antithiamin substances in brackens, such as astragalin, isoquercitrin, rutin, caffeic acid, and tannic acid have Lee and Lin, 1988;Silva et al, 1995;Sun et al, 1997;Lee et al, 1999;Lin et al, 2000;Su et al, 2000;Chen et al, 2005b;Gao et al, 2007;Li J et al, 2014;Li S 2014;Elda et al, 2015 35 Guha et al, 1996 MTT: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (Konoshima et al, 1996). A. evecta and Selaginella tamariscina have been shown to have significant antidiabetic activity (Miao et al, 1996;Nguyen, 2005).…”

Section: Anti-cancer Antidiabetic and Antiviral Activitymentioning

confidence: 99%

“…3d), Selaginella lepidophyla, Selaginella labordei, Selaginella moellendorffii, Selaginella delicatula, S. tamariscina, and Sellaginella doederleinii (Fig. 3e) were shown to have cytotoxic and antimutagenic effects due to the presence of bioflavonoids (Lee and Lin, 1988;Silva et al, 1995;Sun et al, 1997;Lee et al, 1999;Lin et al, 2000;Su et al, 2000;Chen JJ et al, 2005;Gayathri et al, 2005;Woo et al, 2005;Gao et al, 2007;Shi et al, 2008;Tan et al, 2009), while Pteris semipinnata (Fig. 4c) and P. multifida have cytotoxic effects due to the presence of diterpenes (Woerdenbag et al, 1996;Li et al, 1998Li et al, , 1999.…”

Section: Anti-cancer Antidiabetic and Antiviral Activitymentioning

confidence: 99%

A review of the use of pteridophytes for treating human ailments

Xavier-ravi

Vigila

Zhang

et al. 2018

J. Zhejiang Univ. Sci. B

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Abstract:The aim of this review was to explore the pharmacological activity of early tracheophytes (pteridophytes) as an alternative medicine for treating human ailments. As the first vascular plants, pteridophytes (aka, ferns and fern allies) are an ancient lineage, and human beings have been exploring and using taxa from this lineage for over 2000 years because of their beneficial properties. We have documented the medicinal uses of pteridophytes belonging to thirty different families. The lycophyte Selaginella sp. was shown in earlier studies to have multiple pharmacological activity, such as antioxidant, anti-inflammatory, anti-cancer, antidiabetic, antiviral, antimicrobial, and anti-Alzheimer properties. Among all the pteridophytes examined, taxa from the Pteridaceae, Polypodiaceae, and Adiantaceae exhibited significant medicinal activity. Based on our review, many pteridophytes have properties that could be used in alternative medicine for treatment of various human illnesses. Biotechnological tools can be used to preserve and even improve their bioactive molecules for the preparation of medicines against illness. Even though several studies have reported medicinal uses of ferns, the possible bioactive compounds of several pteridophytes have not been identified. Furthermore, their optimal dosage level and treatment strategies still need to be determined. Finally, the future direction of pteridophyte research is discussed.

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Selective Cytotoxicity of Ginkgetin from Selaginella moellendorffii

Cited by 91 publications

References 22 publications

Cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia of alkaloids and flavonoid from two Solanum Species

Cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia of alkaloids and flavonoid from two Solanum Species

Synthesis of Ochnaflavone and Its Inhibitory Activity on PGE₂Production

A review of the use of pteridophytes for treating human ailments

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Selective Cytotoxicity of Ginkgetin from Selaginella moellendorffii

Cited by 91 publications

References 22 publications

Cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia of alkaloids and flavonoid from two Solanum Species

Cytotoxic activities against Ehrlich carcinoma and human K562 leukaemia of alkaloids and flavonoid from two Solanum Species

Synthesis of Ochnaflavone and Its Inhibitory Activity on PGE2Production

A review of the use of pteridophytes for treating human ailments

Contact Info

Product

Resources

About

Synthesis of Ochnaflavone and Its Inhibitory Activity on PGE₂Production