Lasiodiplodin, a potent antileukemic macrolide from Euphorbia splendens

Leet, Kuo-Hsiung; Hayashi, Nanao; Okano, Masayoshi; Hall, Iris H.; Wu, Rong-Yang; Mcphailti, Andrew T.

doi:10.1016/s0031-9422(00)82428-0

Cited by 79 publications

(48 citation statements)

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“…47 Esta substância foi também isolada em pequena quantidade de Annona dioica, (família Anonaceae), sendo que a possibilidade enantiomérica (o carbono 14 é quiral e permite dois estereoisômeros) ainda não foi definitivamente estabelecida. 48 Entre os medicamentos antitumorais de origem vegetal, destacamse os derivados e os correspondentes produtos naturais bioproduzidos pelas espécies Catharanthus roseus ou Vinca rósea, família Apocynaceae (9 e 10, e seus derivados 78 e 79), Camptotheca acumata, família Nyssaceae (80 e seu derivados 81 e 82) e Podophyllum peltatum e P. emodi, família Berberidaceae (11 e 12, derivados de 13).…”

Section: Substâncias Orgânicas Naturais E Semissintèticas Anticancerunclassified

Contribuição da fitoquímica para o desenvolvimento de um país emergente

Braz-Filho¹

2010

Quím. Nova

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Recebido em 2/6/09; publicado na web em 8/12/09 PHYTOCHEMICAL CONTRIBUTION TO DEVELOPMENT OF A EMERGENT COUNTRY. The sustainable development of an emergent country is dependent on a consistent scientific, technologic and innovative policy, on nature and biodiversity, on a rational exploration of natural resources to feeding, social advance and economical aim along with maintenance of health and diseases treatment. Phytochemical investigations may be used to contribute with development throughout undergraduate and graduate career preparing professionals with qualification to these activities, as researcher and professor, including discovering and divulgation of new scientific knowlegments. The role of organic compounds produced by secondary metabolism of plants in the development of new drugs is presented (e. g.) throughout exposition using examples of features involved in this activity, since the recognition of a plant-derived popular medicine, until the laboratory semi-synthesis of its main constituents. Several aspects related to the use of some vegetable species in treatment of many tropical diseases are pointed. Economical and social importance of isolation, structural characterization, pharmacological investigation and chemical transformations of new natural organic substances isolated from the plants are related.Keywords: emergent country; phytochemical investigations; structural identifications. INTRODUÇÃOO desenvolvimento sustentável de um país depende essencialmente de uma política consistente de educação, ciência, tecnologia e inovação, sustentada na preservação da natureza, na biodiversidade e na exploração racional de fontes naturais necessárias para alimentação, avanço social e econômico, num cenário que assegura a manutenção da saúde e a cura de doenças.As atividades da fitoquímica podem contribuir significativamente para a concretização de tal programação através da investigação da flora e seu quimismo, da divulgação e geração de novos conhecimentos e da formação de recursos humanos qualificados. A química de produtos naturais (QPN) de vegetais -fitoquímica, como é concebida atualmente, se dedica principalmente à caracterização estrutural, avaliação de propriedades e investigações biossintéticas de substâncias naturais produzidas pelo metabolismo secundário de organismos vivos. 1 A vida dos organismos vivos -nascimento, crescimento, reprodução, envelhecimento, doenças e morte -é assegurada e controlada pelas transformações químicas realizadas por metabolismos primário (principal atividade dos bioquímicos) e secundário -especializado (atividade primordial do químico de produtos naturais).Assim, os organismos vivos utilizam trajetórias biogenéticas para transformações e interconversões químicas de metabólitos do seu acervo vivo e dinâmico (Esquema 1). As principais biorreações utilizadas em tais processos vitais envolvem reações de alquilação (substituição nucleofílica, adição eletrofílica), rearranjos de Wagner -Meerwein, condensação aldólica, reação de Claisen, formação da base de Schiff, reação d...

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Section: Substâncias Orgânicas Naturais E Semissintèticas Anticancerunclassified

Contribuição da fitoquímica para o desenvolvimento de um país emergente

Braz-Filho¹

2010

Quím. Nova

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“…1 H NMR (500 MHz, CDCl 3 ) δ: 7.29 (d, J 7.6 Hz, ArH-1), 7.40 (t, J 8.1 Hz, 1 H, ArH-2), 6.84 (d, J 8.2 Hz, 1 H, ArH-3), 5.05 (m, 1 H, CH-14), 4,99 (m, 1 H, CH 2 -7), 3.96 (dt, J 11.15 and 1.84 Hz, 1 H, CH 2 -7'), 3.84 (s, 3 H, OCH 3 ), 2.18 (br, 1 H, CH 2 -8), 1.73 (br, 1 H, CH 2 -8'), 1.73 (br, 2 H, CH 2 -12), 1.49-1.35 (m, 6 H, CH 2 -9 to 11). 13 8,9,10,11, (7) To a solution of bromide 6 (1.22 g, 3.56 mmol) in benzene (30 mL), DBU (2.7 mL, 17.8 mmol) was added. After stirring under reflux and an argon atmosphere for 10 h, the reaction mixture was quenched with 10% hydrochloric acid (15 mL) and then extracted with ethyl acetate (3 x 20 mL).…”

Section: -Methoxy-6-(8-hydroxyoctyl) Benzoic Acid (5)mentioning

confidence: 99%

“…The organic phase was concentrated to furnish a yellow solid, which was recrystallized from hexane-ethyl acetate to afford the transunsaturated lactone 7 as white crystals (0.86 g, 94%, mp 79-80 °C). IR (KBr) ν max /cm -1 : 2929, 2864, 1720, 1595, 1572, 1472, 1438, 1258, 1119, 1108, 1071 14- 13, To a solution of unsaturated lactone 7 (0.10 g, 0.38 mmol) in dichloromethane (2 mL) was added drop wise a solution of m-CPBA (0.13 g, 2.0 eq) in dichloromethane (2 mL). The reaction mixture was stirred for 4 h, and then diluted with ethyl acetate (20 mL).…”

Section: -Methoxy-6-(8-hydroxyoctyl) Benzoic Acid (5)mentioning

confidence: 99%

“…16 The 1 H and 13 13 C NMR peaks for the acyclic precursors and macrocyclic lactones were described according to Figure 5. These spectra data will be further explored in connection with a study underway utilizing a NMR computer-aided approach and X-ray crystallography in order to establish the conformational structure of all new macrolactones.…”

Section: Chemistrymentioning

confidence: 99%

“…These orsellinic acid type macrolides also have attracted the attention of many synthetic chemists regarding both chemical and physiological activities. [11][12][13] For instance, methyldehydrolasiodiplodin, a mixture of geometrical isomers used as a precursor for the synthesis of lasiodiplodin, exhibits a rather uniform in vitro activity against human tumors e.g. leukemia, lung, colon, melanoma, ovarian, renal, prostate and breast.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and biological evaluation of new salicylate macrolactones from anacardic acids

Logrado¹,

Silveira

Romeiro

et al. 2005

J. Braz. Chem. Soc.

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No âmbito de uma linha de pesquisa que visa a obtenção de novas substâncias bioativas, a partir de lipídeos fenólicos não-isoprenóides de Anacardium occidentale, descrevemos a síntese e avaliação citotóxica de novas macrolactonas salicílicas, preparadas a partir da mistura de ácidos anacárdicos, principal constituinte do líquido da casca da castanha de caju (LCC) in natura.In connection with our ongoing investigation in the search for new bioactive compounds using non-isoprenoid phenolic lipids from Anacardium occidentale as starting material, we describe the synthesis and cytotoxicity screening of some novel salicylate macrolactones prepared from anacardic acids, the major constitutents of natural cashew nut-shell liquid (CNSL). Keywords: cashew nut shell liquid, anacardic acids, salicylate macrolactones IntroductionNon-isoprenoid phenolic lipids exist in plants from a number of different families, notably the Anacardiaceae shrub, many small plants, and certain bacterial sources. The cashew tree (Anacardium occidentale), a species originally native to Brazil where it is still cultivated, also grown in a large number of other tropical and sub-tropical countries, represents one of the major and cheapest sources of this class of compounds. 1 As the main component of natural cashew nut-shell liquid (CNSL), anacardic acids (1) are the most widely distributed phenolic lipids. Chemically, the anacardic acids feature a convenient salicylic acid system and a long sidechain at the 6-position, in which a double bond is found at C-8 in the monoene, diene and triene components ( Figure 1). Anacardic acids are reported to exhibit a variety of biological activities, 2 and also have stimulated much research in order to prepare drug analogues for application in several fields. 3 In the course of ongoing investigations aiming at new drug candidates, the particular structural behavior and abundance of anacardic acids have prompted us to search for a strategy to convert these materials into analogues of an emerging family of antitumor natural products, for example: oximidines I, II, and III, 4 apicularens A and B, 5 and salicylhalamides A and B 6 (Figure 2), which present a benzofused macrolactone bearing an unusual N-acylated enamide 1218 Logrado et al. J. Braz. Chem. Soc. side-chain. Related to the fact that these benzolactone enamides do not display any significant structural correlations to the profiles of known anti-cancer drugs, they constitute a very attractive new class of lead compounds in the search for antineoplastic agents and have therefore shown considerable interest concerning to isolation, chemical synthesis and mechanistic studies of the biochemical mode of action. [4][5][6][7] Other macrolactones structurally related to the above macrolides include lasiodiplodin, 8 cis-and transresorcylide, 9 and curvularin 10 ( Figure 3). These orsellinic acid type macrolides also have attracted the attention of many synthetic chemists regarding both chemical and physiological activities. 11-13 For instance, methyldehydrola...

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Resorcylic Acid Lactones

Napolitano¹,

Murphy²

2013

Natural Lactones and Lactams

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Lasiodiplodin, a potent antileukemic macrolide from Euphorbia splendens

Cited by 79 publications

References 3 publications

Contribuição da fitoquímica para o desenvolvimento de um país emergente

Contribuição da fitoquímica para o desenvolvimento de um país emergente

Synthesis and biological evaluation of new salicylate macrolactones from anacardic acids

Resorcylic Acid Lactones

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