Biological properties of jatrophane polyesters, new microtubule-interacting agents

Miglietta, Antonella; Gabriel, Ludovica; Appendino, Giovanni; Bocca, Claudia

doi:10.1007/s00280-002-0541-4

Cited by 52 publications

(41 citation statements)

References 19 publications

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“…The unique mechanism of taxol ® promoted considerable interest in finding other chemotypes which act by similar mechanisms, and one such plant-derived chemotype is the jatrophane esters, in particular jatrophane 1, isolated from samples of the Corsican and Sardinian plant, Euphorbia semiperfoliata Viv. (Euphorbiaceae); though reported as a cytotoxin earlier, its actual biological mechanism of action was not reported until recently (Miglietta et al, 2002). Other recently discovered taxol mimics include the microbial metabolites, the epothilones, and the marine invertebrate metabolites, discodermolide, eleutherobin, sarcodictyins and the laulimalides (Cragg et al, 2005;Cragg and Newman, 2004).…”

Section: Cell Cycle Target Inhibition and Anti-cancer Drug Discoverymentioning

confidence: 94%

Plants as a source of anti-cancer agents

Cragg

Newman

2005

Journal of Ethnopharmacology

1,697

1,060

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Plant-derived compounds have been an important source of several clinically useful anti-cancer agents. These include vinblastine, vincristine, the camptothecin derivatives, topotecan and irinotecan, etoposide, derived from epipodophyllotoxin, and paclitaxel (taxol A number of promising new agents are in clinical development based on selective activity against cancer-related molecular targets, including flavopiridol and combretastin A4 phosphate, while some agents which failed in earlier clinical studies are stimulating renewed interest.

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Section: Cell Cycle Target Inhibition and Anti-cancer Drug Discoverymentioning

confidence: 94%

Plants as a source of anti-cancer agents

Cragg

Newman

2005

Journal of Ethnopharmacology

1,697

1,060

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“…Some of these plants are used in folk medicine in the treatment of skin diseases, ulcers and warts, as well as cancer tumors and intestinal parasites (Hartwell, 1969;Rondón et al, 2005). In the past few years, Euphorbia species have been investigated extensively for the presence of polycyclic and macrocyclic diterpenes, some of which have shown several biological effects such as, antitumor (Valente et al, 2004;Miglietta et al, 2003), cytotoxic (Kong et al, 2002), antiviral (Zheng et al, 1998) and multidrug resistance reversing activity (Duarte et al, 2006). Euphorbia lagascae is currently cultivated for the extraction of a 12,13-epoxyoleic acid (vernolic acid), which is found at high levels in seeds, and is used in the oleochemical industry (Cuperus et al, 1996;Krewson and Scott, 1966;Bafor et al, 1993).…”

Section: Introductionmentioning

confidence: 98%

Antileishmanial activity of piceatannol isolated from Euphorbia lagascae seeds

Duarte

Kayser

Abreu

et al. 2007

Phytotherapy Research

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In the search for biologically active compounds from Euphorbia lagascae Spreng, an herbaceous plant native to southeast of Iberic Peninsula, a stilbene, two coumarins and two 12-deoxyphorbol diterpene esters were isolated by chromatographic methods, from the methanol extracts of its defatted seeds. The structures of these compounds were elucidated by a combination of physical and spectral data (IR, MS and high-resolution (1)H-NMR and (13)C-NMR spectroscopy utilizing COSY, HMBC, HMQC and NOESY experiments). The stilbene, piceatannol, was screened for its antileishmanial activity against promastigotes as an extracellular form of Leishmania donovani, Leishmania infantum and Leishmania major, and amastigotes of Leishmania donovani as an intracellular form. Pentostan (sodium stibogluconate), the first line clinical drug, was used as a standard reference. Piceatannol was moderately active against the extracellular forms of the three tested Leishmania species, and more active than the reference compound against the intracellular form of Leishmania donovani.

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“…The previously known family of prenylated benzophenones isolated from Malaysian fruits, such as guttiferone (36), has been shown to possess many biological properties [171][172][173] and have also been shown to induce tubulin assembly in vitro [174]. The jatrophane polyesters (38-40) induced tubulin assembly in vitro but failed to lead to G2/M cell cycle arrest [175]. Dicoumarol (41), a metabolite of coumarin [176], and lutein (42), the endogenous yellow chromophore in the retina [177], both have been reported to be microtubule-stabilizing agents.…”

Section: Other Natural Productsmentioning

confidence: 99%

Microtubule-Stabilizing Natural Products as Promising Cancer Therapeutics

Gallagher¹

2007

CMC

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Paclitaxel and related taxanes exhibit their anticancer activity by promoting tubulin polymerization and stabilizing microtubules, which results in mitotic G2/M arrest and apoptosis. The clinical success of paclitaxel in treating a wide array of tumor types has led to numerous efforts to identify novel natural products with paclitaxel-like mechanisms of action, but which may overcome some of the liabilities of the taxanes. Although the list of natural products that share the paclitaxel-like mechanism is relatively small, it continues to expand and currently includes a number of structurally distinct classes. Despite the mechanistic similarities between these classes, differences exist which may translate into their differential efficacy in the clinic. The past several years have seen a considerable amount of pre-clinical and clinical progress in developing these novel microtubule-stabilizing natural products as cancer therapeutics. This review focuses primarily on recent advances published since 2002.

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Biological properties of jatrophane polyesters, new microtubule-interacting agents

Abstract: Despite their structural difference from paclitaxel and other microtubule-interacting agents, jatrophanes may represent a new type of tubulin binder.

Cited by 52 publications

References 19 publications

Plants as a source of anti-cancer agents

Plants as a source of anti-cancer agents

Antileishmanial activity of piceatannol isolated from Euphorbia lagascae seeds

Microtubule-Stabilizing Natural Products as Promising Cancer Therapeutics

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