Efforts toward the total synthesis of a jatrophane diterpene

Mohan, Priya; Koushik, Krishna; Fuertes, Michael J.

doi:10.1016/j.tetlet.2012.03.080

Cited by 12 publications

(11 citation statements)

References 26 publications

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“…The search for less toxic and more potent anti-carcinogenic drugs is based on the fact that current drugs are scarcely selective and highly toxic to normal cells (Mohan, Koushik & Fuertes, 2012). The most promising sources of such molecules are plants, especially those used for herbal medicine (Alonso-Castro et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Production of cytotoxic compounds in dedifferentiated cells ofJatropha curcasL. (Euphorbiaceae)

Ovando-Medina

Pérez-Díaz

Ruiz-González

et al. 2016

PeerJ

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This study addresses the in vitro culture as an alternative to obtain compounds with cytotoxic activity from the medicinal plant Jatropha curcas (Euphorbiaceae). We determined the presence of cytotoxic compounds in both whole plants and dedifferentiated cells. We evaluated the effect of auxin, cytokinins and light on callus induction in cotyledon explants. We found that the most effective combination to induce callus was the auxin 2,4-D (5 mM) with the cytokinin 6-BAP (2.5 mM), on Murashige-Skoog medium in darkness. We compared the callogenic potential among accessions from different geographic origins, finding that ARR-251107-MFG7 is most prone to form callus. The roots of J. curcas grown in field produced a compound chromatographically similar to the cytotoxic diterpene jatrophone. The profile of compounds extracted from the dedifferentiated cells was similar to that of the whole plant, including a relatively abundant stilbene-like compound. This study contributes to the future establishment of protocols to produce anti-cancer compounds from J. curcas cultivated in vitro.

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Section: Introductionmentioning

confidence: 99%

Production of cytotoxic compounds in dedifferentiated cells ofJatropha curcasL. (Euphorbiaceae)

Ovando-Medina

Pérez-Díaz

Ruiz-González

et al. 2016

PeerJ

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“…[65] It was intended to prepare the target compound by HWE olefination of cyclopentane fragment 196 with phosphonate 203 and subsequent RCM reaction.…”

Section: Mohan (2012)mentioning

confidence: 99%

“…[65] One year later, a slightly modified approach was reported that was intended to circumvent the problems observed in the key HWE olefination reaction in their preliminary route. [75] The modified sequence, outlined in Scheme 38, should also deliver jatrophane derivative 205 (see Scheme 33) and was based on an NHK coupling reaction as the key step for the elaboration of the crucial C6-C7 bond.…”

Section: Mohan (2013)mentioning

confidence: 99%

Progress in the Preparation of Jatrophane Diterpenes

Rinner

2015

Eur J Org Chem

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“…Despite the challenging structural properties, only a few approaches to jatrophane diterpenes have been reported. 10−24 …”

Section: Introductionmentioning

confidence: 99%

Synthesis of an Advanced Intermediate of the Jatrophane Diterpene Pl-4: A Dibromide Coupling Approach

Fürst

Rinner

2013

J. Org. Chem.

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The preparation of an advanced intermediate toward the synthesis of the jatrophane diterpene Pl-4 is described. The key step is a regioselective chelation-controlled lithiation of the (Z)-configured bromide in the corresponding vinyl dibromide precursor. The method outlined within this Article is suitable for the facile access of sterically hindered internal vinyl halides for further coupling reactions.

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Efforts toward the total synthesis of a jatrophane diterpene

Cited by 12 publications

References 26 publications

Production of cytotoxic compounds in dedifferentiated cells ofJatropha curcasL. (Euphorbiaceae)

Production of cytotoxic compounds in dedifferentiated cells ofJatropha curcasL. (Euphorbiaceae)

Progress in the Preparation of Jatrophane Diterpenes

Synthesis of an Advanced Intermediate of the Jatrophane Diterpene Pl-4: A Dibromide Coupling Approach

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