Molluscicidal activity of Solanum species of the Northeast of Brazil on Biomphalaria glabrata

Silva, Tânia Maria Sarmento; Câmara, Celso A.; Agra, Maria de Fátima; Carvalho, Mário Geraldo de; Frana, Marli Terezinha; Brandoline, Solange Viana Paschoal Blanco; Paschoal, Luciana da Silva; Braz-Filho, Raimundo

doi:10.1016/j.fitote.2006.05.007

Cited by 40 publications

(29 citation statements)

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“…[6][7][8] Solanum crinitum Lam (Solanaceae), popularly known as "jurubeba" and "fruto-de-lobo", is a shrub or small tree in South America, including southern Brazil and Colombia. 9,10 In the course of our pharmacological and phytochemical investigations of Solanum species, 3,4,8,[11][12][13] we have reported the cytotoxic and antitumoral activities of flavonoids isolated from trichomes of young branches Other Chemical Constituents Isolated from Solanum crinitum Lam. (Solanaceae) J. Braz.…”

Section: O-b-d-apiofuranosyl-(1→5)-b-d-apiofuranosyl-(1→6)-b-d-glucopmentioning

confidence: 99%

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Cornelius

Carvalho

Alves

et al. 2010

J. Braz. Chem. Soc.

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(7), ácido 4-hidroxibenzoico (12), e quatro derivados do ácido cinâmico: cis-e trans-cumárico (10 e 11), cis-e trans-cumarato de etila (8 e 9), isolados de tricomas do fruto. Do extrato metanólico de frutos verdes foram isolados três alcalóides esteroidais glicosilados: solamargina (13), 20-epi-solamargina (14) e solasonina (16). Os derivados 3,5,7,4'-tetra-O-metil-kaempferol (4), 3,7,4'-tri-O-metil-kaempferol (5), 3,7,4'-tri-O-metil-5-Oacetil-kaempferol (6), peracetil-epi-solamargina (15) e peracetil-solasonina (17) foram sintetizados e estão sendo registrados pela primeira vez na literatura. As estruturas foram definidas através de análise de dados espectrométricos.The phytochemical investigation of Solanum crinitum Lam led to the isolation from the fruit trichomes of four flavonoids, tiliroside (1), astragalin (2), kaempferol (3), biochanin A-7- O-b-D-apiofuranosyl-(1→5)-b-D-apiofuranosyl-(1→6)-b-D-glucopyranoside (7), along with 4-hydroxybenzoic acid (12), and four cinnamic acid derivatives, cis-and trans-coumaric acids (10 and 11) and cis-and trans-ethyl coumarate (8 and 9). Three tri-glycosyl-steroidal alkaloids, solamargine (13), 20-epi-solamargine (14) and solasonine (16) were isolated from the methanolic extract of the green fruits. The derivatives 3,5,7,4'-tretra-O-methyl-kaempferol (4), 3,7,4'-tri-O-methyl-kaempferol (5), 3,7,4'-tri-O-methyl-5-O-acetyl-kaempferol (6), the peracetyl-episolamargine (15) and peracetyl-solasonine (17) were prepared. The structures were established through the analysis of their spectral data. The complete 1 H and 13 C NMR data assignments of the new peracetyl derivatives of the alkaloids were made.Keywords: Solanum crinitum, Solanaceae, steroidal glycoalkaloids, flavonoids, cinnamic acids Introduction Solanum (L) is the most representative genus of Solanaceae, containing about 1,500 species, and 5,000 epithets. It is widespread in tropical and subtropical regions of all the world, but its highest diversity occurs in South America. 1 Solanum species are a rich source of steroidal alkaloids, flavonoids and their glycosides which are known to possess a variety of biological activities. The glycoalkaloids are natural toxins with ecological and human health importance, such as the allelopathic effect against herbivores, against pathogenic microorganism 2,3 and molluscicidal activity, 4 and are also of interest as starting material for anabolic, anti-fertility, anti-inflammatory, anti-allergic drugs. 5 As the alkaloids, the flavonoids are a frequent group of compounds in Solanum species, and can be used as systematic markers for the family taxons. [6][7][8] Solanum crinitum Lam (Solanaceae), popularly known as "jurubeba" and "fruto-de-lobo", is a shrub or small tree in South America, including southern Brazil and Colombia. 9,10 In the course of our pharmacological and phytochemical investigations of Solanum species, 3,4,8,[11][12][13] we have reported the cytotoxic and antitumoral activities of flavonoids isolated from trichomes of young branches Other Chemical Constituents Is...

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Section: O-b-d-apiofuranosyl-(1→5)-b-d-apiofuranosyl-(1→6)-b-d-glucopmentioning

confidence: 99%

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Cornelius

Carvalho

Alves

et al. 2010

J. Braz. Chem. Soc.

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“…15,16 In our previous studies we had found that several species of Solanum, including the unripe fruits of S. asperum have potentially significant molluscicidal activity. 2,3 The crude alkaloid fraction obtained from the active total MeOH extract as well as the pure alkaloids isolated were tested for the molluscicidal activity (Table 2). Individually, the glykoalkaloids solanandaine (1) (LC 50 =73.1 g mL -1 ), solasonine (2) (LC 50 =47.0 g mL -1 ) and solamargine (3) (LC 50 =26.3 g mL -1 ), were found to be less active than the total MeOH (LC 50 =25.5 g mL -1 ) 3 and the crude alkaloidal extracts (LC 50 =9.7 g mL -1 ) of S. asperum (Table 3).…”

Section: Resultsmentioning

confidence: 99%

“…1 In this region, many species of Solanum are widely used in popular medicine and are commonly known as 'yubeba', the word derived from Tupi Guarani that refers to the prickles found on the stems of several of the species. 1 Some common and wide-spread Solanum species of Brazil had shown 2,3 considerable molluscicidal activity demonstrated by several members of the genus investigated earlier. 4,5 Thus, we have been studying various species of Solanum growing in our country 3,[6][7][8][9][10] with the expectation that the extracts of plants of this genus might be useful in the control of Biomphalaria glabrata, the intermediate host of Schistosoma mansoni, the parasite that causes human schistosomiasis in Brazil.…”

Section: Introductionmentioning

confidence: 96%

Steroidal glycoalkaloids and molluscicidal activity of Solanum asperum Rich. fruits

Silva¹,

Câmara

Freire

et al. 2008

J. Braz. Chem. Soc.

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O fracionamento bio-monitorado do extrato alcaloídico dos frutos verdes de Solanum asperum forneceu um novo alcalóide esteroidal, denominado solanandaina, juntamente com a solasonina e a solamargina. Tanto o extrato alcaloídico como os glicoalcalóides isolados apresentaram potente atividade moluscicida.Bioassay-guided fractionation of the alkaloidal extract of the green fruits of Solanum asperum afforded a new compound, solanandaine along with solasonine and solamargine. The total crude alkaloids as well as the isolated pure alkaloids exhibited significant molluscicidal activity.Keywords: Solanum asperum, glycoalkaloid, solanandaine, solasonine, solamargine, molluscicidal IntroductionSolanum L. (Solanaceae) is distributed mainly throughout the tropical and subtropical regions of the world and is the largest and most complex genus of the family Solanaceae. In Brazil, Solanum is represented by about 350 species. 1 In this region, many species of Solanum are widely used in popular medicine and are commonly known as 'yubeba', the word derived from Tupi Guarani that refers to the prickles found on the stems of several of the species. 1 Some common and wide-spread Solanum species of Brazil had shown 2,3 considerable molluscicidal activity demonstrated by several members of the genus investigated earlier. 4,5 Thus, we have been studying various species of Solanum growing in our country 3,6-10 with the expectation that the extracts of plants of this genus might be useful in the control of Biomphalaria glabrata, the intermediate host of Schistosoma mansoni, the parasite that causes human schistosomiasis in Brazil. In our previous bioassays, the crude MeOH extract of the unripe fruits of S. asperum Rich showed 3,11 activity in studies with Artemia salina (LC 50 = 420.5 g mL -1 ) and Biomphalaria glabrata (LC 50 = 25.5 g mL -1 ). Bioassay-guided fractionation indicated that the activity was concentrated in the alkaloid fraction. Thus, the alkaloid fraction upon CC on Sephadex LH-20 followed by PTLC on Silica gel afforded a new compound, (2) and solamargine (3). In this work, we wish to report the isolation, characterization and the molluscicidal activity of the alkaloids of S. asperum unripe fruits. Results and DiscussionSolanum asperum Rich. is popularly known in Brazil as 'jussara' or 'coça-coça'. It is a neotropical species belonging to the section Brevantherum with wide distribution in South America. Extract of S. asperum unripe fruits demonstrated significant molluscicidal activity. With the aid of biossay-guided fractionation of the crude alkaloid mixture, solanandaine, solasonine and solamargine were isolated from the green fruits of S. asperum. Silva et al. 1049 Vol. 19, No. 5, 2008 Solanandaine (1) (Table 1) are fully compatible with a -D-glucose structure for this hexose unit. The other two anomeric signals are broad singlets at H 5.84 and 6.38, typical of -L-rhamnose unities. The HSQC spectrum shows that the three signals at C 100.6, 102.4 and 103.2 are due to the corresponding anomeric carbons of the three ...

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“…Seis dos dezessete extratos testados revelaram atividade, sendo que duas espécies (S. jabrense e S. stipulaceum) forneceram resultados efetivos para sugerir a utilização no controle de esquistossomose. 30 A solavetivona (58) e a solasodina (59) foram isoladas de S. jabrense. 31,32 Um alcaloide esteroidal isolado de Solanum criticum foi recentemente caracterizado como 20-episolasodina (59a).…”

Section: Esquema 5 Conversão Biocataítica 8-hidroximanzamina a (8-ohunclassified

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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Molluscicidal activity of Solanum species of the Northeast of Brazil on Biomphalaria glabrata

Cited by 40 publications

References 8 publications

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Steroidal glycoalkaloids and molluscicidal activity of Solanum asperum Rich. fruits

Contribuição da fitoquímica para o desenvolvimento de um país emergente

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