Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives

Hueso-Falcón, Idaira; Girón, Natalia; Velasco, Patricia Barrera; Amaro-Luis, Juan M.; Ravelo, Ángel G.; Heras, Beatriz de las; Hortelano, Sonsoles; Estévez‐Braun, Ana

doi:10.1016/j.bmc.2009.11.064

Cited by 48 publications

(24 citation statements)

References 56 publications

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“…Thus, such natural compounds as: acetate 78, alcohol 79 or in the case of 15-oxo-ent-kaurene derivatives, α-phenylethylketone 76 and α-oxopyrazoline 80 exhibit no such activity. Moreover, the cytotoxic activity of methyl 15-oxo-ent-kaur-16-en-19-oate 75 is 35 times greater, than that of initial acid 77 [44] …”

Section: Scheme 6 Electrophilic Addition At a Double Bond Of Ent-kaumentioning

confidence: 93%

“…The GC-analysis after 48 hours showed the 84% conversion with a diastereomeric ratio 59 / 60 = 61:39. To study the cytotoxicity of ent-kauranes with respect to some human cancer cells, derivatives 61 -63 were recently synthesized by electrophilic addition at the double bond of ent-kaur-16-en-19-oic acid 1 [44]. It was established, that this modifi cation (Scheme 6) led to the complete disappearance of the anticancer effect.…”

Section: Mcpbamentioning

confidence: 99%

“…In the same direction, 15α-hydroxy-ent-kaur-16-en-19-oic acid 64 was synthesized with a better yield by using SeO 2 /EtOH system, starting with ent-kaur-16-en-19-oic acid 1 and by saponifi cation of the 15α-angeloyl-ent-kaur-16-en-19-oic acid 69 [43]. Due to a continuing interest in the evaluation of biological potential of natural diterpenes, Hueso-Falcónin et al [44] reported a study on the preparation of ent-kaurane derivatives from the natural ent-kaur-16-en-19-oic acid 1 (Scheme 8). These compounds were tested for their ability to induce apoptosis of signaling pathway in mouse and human cancer cells and some conclusions about structure-activity relationships have been made.…”

Section: Scheme 6 Electrophilic Addition At a Double Bond Of Ent-kaumentioning

confidence: 99%

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Synthetic Transformations of Ent-Kaurenoic Acid

Morarescu¹

2015

ChemJMold

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Abstract. This paper presents a review on kaurane diterpenes, covering various aspects of chemical and microbiological transformations of native ent-kaurenoic acid, namely, its reactions via COOH groups, double bonds and rearrangements of the carbon skeleton that lead to a wide range of natural and synthetic derivatives with potential biologic activities and can present convenient synthons for the syntheses of other native ent-kauranes. Ent-kaur-16-en-19-oic acid 1 is one of the intermediate compounds, which is involved in the biosynthesis of diverse ent-kaurane diterpenes, including gibberellins, a group of growth phyto-hormones. Therefore, it is not surprising that many ent-kauranes and their derivatives act as growth regulators in plants [25]. KeywordsThe broad spectrum of presented by the ent-kaurane diterpenes biological activities has motivated countless studies of structural modifi cations of the skeleton, aiming at obtaining the new potentially bioactive substances. These structural transformations have been achieved either chemically or microbiologically, by using microorganism cultures.

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Section: Scheme 6 Electrophilic Addition At a Double Bond Of Ent-kaumentioning

confidence: 93%

Section: Mcpbamentioning

confidence: 99%

Section: Scheme 6 Electrophilic Addition At a Double Bond Of Ent-kaumentioning

confidence: 99%

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Synthetic Transformations of Ent-Kaurenoic Acid

Morarescu¹

2015

ChemJMold

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“…Occasionally, cattle consume different species of Espeletia and other paramo vegetation, although of poor quality (Molinillo and Monasterio, 2002). Both compounds have complicated structures, and have a tetracyclic skeleton and lipophilic properties (Hueso-Falcón et al, 2010), they differ in an additional endocyclic double bond presented by compound [2] in the 9-11 position. Different investigators have produced an important number of derivatives by hemi-synthesis, for instance, derivatization of the acid group on carbon-19 to obtain alcohols, esters and amides (Diamantino et al, 2008;Mthembu et al, 2010;Haraguchi et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

In vitro antimicrobial activity of two dibutyltin(IV) complexes of kaurenic acids derivatives

Quintero-Rincón¹,

Fontal²,

Fonseca³

et al. 2016

Emir. J. Food Agric

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“…[6][7][8] Regarding the chemical composition, a series of ent-pimarane and ent-kaurane diterpenes have been isolated from this plant. 9) Although these diterpenes are best known for their cytotoxic or cardiovascular effects, 10,11) there have also some reports indicating their anti-inflammatory activity. Tedanol, a ent-pimarane diterpene isolated from Tedania ignis, significantly reduced carrageenan-induced inflammation in mice.…”

mentioning

confidence: 99%

ent-Kaurane and ent-Pimarane Diterpenes from Siegesbeckia pubescens Inhibit Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia

Lee

Kim

Lee

et al. 2014

Biological & Pharmaceutical Bulletin

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The extract of Siegesbeckia pubescens herb and its chemical constituents were tested for the ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglia. The methanol extract and the 90% MeOH fraction of S. pubescens effectively attenuated lipopolysaccharide-induced nitric oxide production. Several steps of chromatography yielded eight ent-kaurane diterpenes (1-8) and one ent-pimarane diterpene (9) from the 90% MeOH fraction. Among these compounds, compounds 2-9 showed significant inhibitory effect on lipopolysaccharide-induced nitric oxide production in BV2 microglia. Compounds 3 and 9 concentration-dependently decreased the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), supported by quantitative real time polymerase chain reaction (PCR) and Western blot analysis. These results suggest that ent-kaurane and ent-pimarane diterpenes isolated from S. pubescens are expected to be potential candidates against neuroinflammation-related disease.

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Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives

Cited by 48 publications

References 56 publications

Synthetic Transformations of Ent-Kaurenoic Acid

Synthetic Transformations of Ent-Kaurenoic Acid

In vitro antimicrobial activity of two dibutyltin(IV) complexes of kaurenic acids derivatives

<i>ent</i>-Kaurane and <i>ent</i>-Pimarane Diterpenes from <i>Siegesbeckia pubescens</i> Inhibit Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia

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