Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products

Gauthier, Charles; Legault, Jean; Piochon, Marianne; Lavoie, Serge; Tremblay, Sarah; Pichette, André

doi:10.1016/j.bmcl.2009.02.076

Cited by 37 publications

(23 citation statements)

References 34 publications

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“…All of the chacotriosidic saponins were tested in vitro for their cytotoxic activity. Although lupane-type chacotriosides (113-115) did not show any cytotoxicity, allobetulin and 28-oxoallobetulin chacotriosides (122 and 123) exhibited a cytotoxic activity profile similar and even stronger than betulinic acid (3) against MCF-7 and PC-3 human cancer cell lines (Gauthier et al 2009d). …”

Section: Chacotriosidic Saponinsmentioning

confidence: 97%

“…Furthermore, the apoptosis-inducing activity of solamargine, which is a steroidal alkaloid featuring the same chacotrioside moiety at the C-3 position, seems to be due to the presence of rhamnose moieties (Cham and Daunter 1990;Chang et al 1998) as it is the case for dioscin (Wang et al 2007). Thus, as lupane-type saponins with rhamnose residues were found to be highly active against cancer cells, we considered synthesizing lupeol, betulin and betulinic acid chacotriosidic saponins (113-115) (Gauthier et al 2009d). As shown in Fig.…”

Section: Chacotriosidic Saponinsmentioning

confidence: 99%

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Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins

et al. 2010

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Lupeol, betulin and betulinic acid are members of the so-called lupane-type triterpenoids. These natural products found worldwide in quite of lot of vegetables, fruits and plant species exhibit promising pharmacological activities including antiinflammatory, anti-HIV and antitumor activities. Nevertheless, the poor pharmacokinetic properties of these cholesterol-like triterpenoids hampered further pharmaceutical developments. The synthesis of lupanetype saponins, i.e., sugar-derived lupanes, seems to be a good avenue to improve both their water solubility and pharmacological activity. The aims of this review are twofold: first, to describe the biological activity of naturally occurring lupane-type saponins, and second, report the different methodologies employed for the elaboration of glycosidic linkages at the C-3 and/or C-28 positions on the lupane core. The synthesis of both natural and unnatural lupane-type saponins is discussed with an emphasis on molecules exhibiting relevant biological activities.

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Section: Chacotriosidic Saponinsmentioning

confidence: 97%

Section: Chacotriosidic Saponinsmentioning

confidence: 99%

Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins

et al. 2010

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“…36 A importância do ácido betulínico (67) estimulou o desenvolvimento de novas atividades de pesquisa na busca, inclusive, de produtos derivados dotados de outras atividades biológicas através de biotransformações químicas 37 ou utilizando, inclusive, novos reagentes e novas reações. [38][39][40][41] Transformações microbiológicas (biotransformações, Esquema 6) para obtenção de substâncias mais ativas e/ou menos tóxicas assumem interesse social e econômico, principalmente quando tais conversões seletivas através de modificações sintéticas revelam dificuldades (Esquema 6). 37 As transformações microbiológicas de substâncias naturais e sintéticas oferecem novos horizontes para modificações estruturais destinadas a vários objetivos, desde a introdução de grupos funcionais a rearranjos moleculares.…”

Section: Substâncias Orgânicas Naturais Anti-hivunclassified

“…41 Outras classes de substâncias naturais têm também revelado potente atividade inibidora sobre HIV, podendo-se citar, como exemplos adicionais, a cumarina 70 42,43 e os flavonoides 7-O-b-D-galactopiranosilacacetina (71) e crisina (72), isolados das flores de Chrysantbermum morifolium (família Compositae) juntamente com mais sete substâncias conhecidas, sendo que a conhecida flavona crisina (72) revelou-se a mais ativa. 44 …”

Section: Substâncias Orgânicas Naturais Anti-hivunclassified

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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“…There have been sporadic reports on the structure-activity relationship, providing a possible correlation between the cytotoxic effects and certain structural features. Readers are referred to some interesting research by Gauthier et al 24,32,33 In a recent study by Liu et al, a synthetic derivative of β-hederin was evaluated for its cytotoxic properties in five human cell lines (ie, HeLa, MCF-7, HL-60, HT1080, and Hep-G2). 34 The authors reported synthesis of 13 novel triterpenoid saponins, designed as amide derivatives of the natural cytotoxic saponin, β-hederin, using a stepwise glycosylation strategy.…”

Section: Saponins As Cytotoxic Agentsmentioning

confidence: 99%

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Thakur¹,

Melzig²,

Fuchs³

et al. 2011

BTAT

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Saponins are bioactive compounds produced mainly by plants but also by some marine organisms and insects. In the recent past, there has been unforeseen interest in the clinical utilization of saponins as chemotherapeutic agents. The research on saponins in various forms as a treatment for cancer has generated a lot of potential. The advent of nanotechnology and the cytotoxicity enhancing properties of saponins are some of the highlights of the current decade. This review gives an updated overview of the clinical potential that saponins hold as cytotoxic agents, and covers the literature for 1957-2011, with the main focus on research conducted in the last decade. It is conceivable that saponins hold a lot of therapeutic potential and could be a lead for identification of synthetic or semisynthetic molecules for the treatment of cancer via membrane-mediated or transport-mediated pathways.

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Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products

Cited by 37 publications

References 34 publications

Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins

Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins

Contribuição da fitoquímica para o desenvolvimento de um país emergente

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

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