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

Abstract

(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...

Orthosiphol A from the Aerial Parts of Orthosiphon aristatus is Putatively Responsible for Hypoglycemic Effect via α-Glucosidase Inhibition

“…[I] mM purified using the combination of Sephadex LH20 and silica gel column chromatography, affording four flavonoids named sinensetin (1), salvigenin (2), tetramethylscutellarein (3), and 3,7,4'tri-O-methylkaempferol (4), together with a diterpenoid named orthosiphol A (5) ( Figure 1). The identities of the isolated compounds were made by spectroscopic analysis, particularly NMR, and MS, which coincided well with previous reports [11][12][13][14][15].…”

The Genus Solanum: An Ethnopharmacological, Phytochemical and Biological Properties Review

“…Spanish: tamarillo, tomate de árbol, tomate SerranoEcuador, Colombia, Peru, Bolivia, Rwanda, South Africa, India, Nepal China, United States, Chile, Australia, New Zealand, Malaysia, Philippines, Puerto Rico, Bhutan [71–74]Ripe fruit edible, preservative [71, 72], antioxidant [75]13 S. buddleifolium UnknownBrazil [79]Unknown14 S. caavurana Laranjinha do mato, ‘jurubebarana’ or ‘jurubeba-branca’Brazil (Ceará, Bahia, Mato Grosso do Sul, Paraná,Santa Catarina States), Paraguay, ArgentinaAnemia, liver disorders, digestion [80]15 S. capsicoides Cockroach berry, polohauai’i (Polynesia), devil’s appleBrazil, Central America, Australia, Brooklyn, New York [81–84]Ornamental [83], anti-inflammatory [85], anticancer [86], antihypertensive [87]16 S. cathayanum ChinaAnti-inflammatory, anti-bacterial [102], antitumor, anti-neurodegenerative [102–106]17S. cernuum“Panaceia”BrazilGastric ulcers, hepatic injuries, skin disorders, anti-tumor, depurative, diuretic, antihemorrhagic, antiblennorrhoea, cardiac disorders, analgesic, anti-inflammatory, urinary disorders, gastric cancer, gonorrhea [107–112]18 S. chrysotrichum “Sosa”MexicoAnti-mycotic, anti-inflammatory [113–120]19 S. cornifolium Latin AmericaAnti-mycotic [121]20 S. crinitum “jurubeba” and “fruto-de-lobo”Brazil, ColombiaAnti-tumor [122, 123]…”

Estudo farmacobotânico comparativo de folhas de Solanum crinitum Lam., Solanum gomphodes Dunal e Solanum lycocarpum A. St.-Hil., Solanaceae

“…Solanum crinitum possui frutos considerados tóxicos (Agra & Bhattacharyya, 1999), dos quais já foram isolados alcalóides e flavonóides, que apresentaram atividade citotóxica (Esteves-Souza et al, 2002;Cornelius et al, 2004). A outra espécie, Solanum gomphodes, também nativa da flora brasileira é usada popularmente com as mesmas indicações de S. lycocarpum, entretanto, seus constituintes químicos e atividades biológicas são desconhecidos.…”