Isolation, structure and synthesis of chevalierins A, B and C, cyclic peptides from the latex of Jatropha chevalieri

Baraguey, Carine; Auvin‐Guette, Catherine; Blond, Alain; Cavelier, Florine; Lezenven, Françoise; Pousset, Jean-Louis; Bodo, Bernard

doi:10.1039/a804003f

Cited by 34 publications

(51 citation statements)

References 10 publications

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“…Essential oils, present in numerous plant varieties, contain terpene derivatives that can cause allergic or irritant reactions. For example, furan sesquiterpenes and triterpenes are found in J. chevalieri oil; triterpenes are present in oils from L. hastata , C. procera , S. kunthianum , B. parkii and D. microcarpum ; and terpenoids are found in G. senegalensis . M. leucadendra (cajeput tree) yields an essential oil of tea tree (tea tree oil), as does Melaleuca alternifolia , which can induce contact eczema through its terpene compounds .…”

Section: Discussionmentioning

confidence: 99%

Negative cutaneous effects of medicinal plants in Senegal

et al. 2015

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SummaryUse of medicinal plants is common and widespread throughout Africa, including in Senegal. Because efficacy has been demonstrated, public policies have been instituted that have allowed plant-based therapies to have an important role in general primary care. However, little is known about the cutaneous safety of many plant-based therapies. In this 6-month prospective study all cases of dermatitis induced or aggravated by exclusive use of medicinal plants were evaluated via skin allergy testing. The results were classified and compared with the available literature. Forty-three cases of plant-therapy-associated cutaneous reactions were identified, including worsening of existing conditions (56%), recurrence of a previously resolved condition (16%) and new dermatitis arising spontaneously (28%). In the cases where the condition was new, generalized exfoliative dermatitis occurred in 42% of cases with an average time of onset of 9 days. Specific plants were identified in 65% of cases and included 18 varieties. The frequency and severity of plant-induced cutaneous reactions should be the basis for the creation of a phytovigilance programme and re-evaluation of how traditional medicine is used in the general population. When irritation occurs, identification of the responsible plant and allergy testing should be the first steps towards relieving symptoms.In Africa, many plants are used empirically in traditional medicine. According to the World Health Organization, plantbased therapies represent a first-line medical recourse for more than 80% of people across all social classes in many African countries. This is due to the accessibility and low cost of plant-based medicine, along with advertisements in the media by an increasing number of traditional practitioners. However, these practitioners are sometimes illiterate and incompetent. The current cultural environment promotes self-medication and/or polymedication.Often called traditional phytotherapy, plant-based therapies can be delivered via either topical or oral routes. Topical delivery consists of direct application of the plant onto the skin, while the oral route encompasses ingestion of a liquid maceration of one or several plants. The benefits of plantbased therapies have been demonstrated; various administrative policies currently ensure that phytotherapy is an important component of primary-care medicine in Africa. However, the potential for harmful effects remains largely unknown by the general population, prescribers, and health and political authorities.Many dermatological afflictions diseases arise from or are exacerbated by the inappropriate and abusive use of these plants. The condition may be life-threatening when it is an erythroderma (exfoliative dermatitis) or leads to synechiae of ocular and genital mucous membranes. Despite the current use of hundreds of plants in traditional medicine, very few toxicological studies have been conducted in research laboratories. The present study was performed to evaluate the cutaneous safety of several com...

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Section: Discussionmentioning

confidence: 99%

Negative cutaneous effects of medicinal plants in Senegal

et al. 2015

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“…The BOP reagent was found to be best in the macrocyclization step to give axinastatin 4, cyclo (Pro-Leu-Thr-Pro-Leu-Trp-Val) [121], while chevalierin C, cyclo (Tyr-Thr-Ile-Phe-Asp-Ile-Phe-Gly-Ala) was cyclized using HBTU under high dilution [122]. …”

Section: Cyclotripeptides All-l Cyclotripeptides With All α-mentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

414

241

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Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

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“…43 Outros como querimolaciclopeptídeo A e B, 44 diantina E 45 e segetalina C 46 também apresentaram ação citotóxica. Os peptídeos isolados de Euphorbiaceae, exclusivamente do gênero Jatropha, são notórios pela atividade antiproliferativa do parasita Plasmodium falciparum, como por exemplo, quevalierina A, 47 mahafaciclina A 42 e B 48 e polianina A, B e C. 49 Além das atividades citotóxica e antimalárica, outros euciclopeptídeos exibiram atividade inibidora de proteases, [50][51][52] inibidora da cicloxigenase, 53,54 imunomodulador, 55,56 imunossupressor 38 e mimético de hormônios estrogênicos 57 (Figura 4).…”

Section: Potencial Biológico De Euciclopeptídeos: Peptídeos Constituíunclassified

Peptídeos cíclicos de biomassa vegetal: características, diversidade, biossíntese e atividades biológicas

Picchi¹,

Altei²,

Saito³

et al. 2009

Quím. Nova

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Recebido em 7/4/08; aceito em 23/9/08; publicado na web em 30/4/09 CYCLIC PEPTIDE FROM PLANT BIOMASS: CHEMICAL FEATURES AND DIVERSITY, BIOSYNTHESIS AND BIOLOGICAL ACTIVITIES. Natural peptides are outstanding as the most promising macromolecules in the search for new drugs, especially those of cyclic nature. The higher plants revealed a very peculiar composition of their cyclic peptides, which distinguish themselves by a "head-to-tail" cyclization. It is possible to define two groups of cyclic peptides from plant biomass. Those called in this review as Eucyclopeptides formed by 2-12 amino acid, and Cyclotides considered as circular polypeptides, composed of 29-37 amino acid that retain three disulfides bridges in an arrangement known as cyclic cystine knot. Searching for plant peptides should form into a subject for scientific research in the forefront of great importance for bioprospecting natural products macromolecular.Keywords: cyclic peptides; eucyclopeptides; cyclotides. INTRODUÇÃO"Para todos os alvos moleculares importantes no corpo humano existem compostos naturais em outras espécies e em mais de uma em especial". Com essa afirmação Tulp & Bohlin propõem um apropriado paradigma para a química de produtos naturais e para a farmacologia. 1 Esses autores reconhecem que a validade desta citação depende do conhecimento dos mecanismos e funções moleculares e da especificidade de cada receptor biológico, além da elucidação de todos os produtos naturais existentes. Embora a proposta possa parecer ousada, não encontrou muita resistência da comunidade científica. 2,3 Talvez o principal alicerce desse novo paradigma seja a similaridade genética entre as espécies. Nosso código genético armazena cerca de 30.000 genes, dos quais 289 foram relacionados à doenças humanas. Surpreendentemente, quase a metade desses genes (ligados à doenças) tem um correspondente em Arabidopsis thaliana (L.) Heynh. 4 Com as descobertas do código genético humano além de outros organismos e os últimos desenvolvimentos sobre o estudos "-oma" (genoma, transcriptoma, proteoma e metaboloma) e tudo que diz respeito às reações bioquímicas responsáveis pela complexidade celular, as substâncias proteicas tornaram-se objeto de pesquisa multidisciplinar envolvendo química e biologia, principalmente. Dessa forma, discute-se cada vez mais a aplicação das ferramentas da biologia molecular na química de produtos naturais, onde o escopo principal pode ser proteínas e peptídeos. 5 Acredita-se que na era pós-genômica a quimio-genômica será uma alternativa eficiente na busca de fármacos para o tratamento de doenças de origem gené-tica e também de medicamentos com ação direta em determinados receptores celulares.Nesse contexto, os peptídeos de origem natural destacam-se como macromoléculas promissoras na busca de novos fármacos, especialmente os de natureza cíclica. Nos últimos anos as descobertas de peptídeos bioativos cresceram de forma exponencial. Newmann et al. revelam que de um total de 868 de fármacos indicados para uso médico entre 1981-2001, apenas 91 ...

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Isolation, structure and synthesis of chevalierins A, B and C, cyclic peptides from the latex of Jatropha chevalieri

Cited by 34 publications

References 10 publications

Negative cutaneous effects of medicinal plants in Senegal

Negative cutaneous effects of medicinal plants in Senegal

The cyclization of peptides and depsipeptides

Peptídeos cíclicos de biomassa vegetal: características, diversidade, biossíntese e atividades biológicas

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