Caavuranamide, a novel steroidal alkaloid from the ripe fruits of Solanum caavurana Vell. (Solanaceae)

Abstract

A investigação fitoquímica dos frutos maduros de Solanum caavurana Vell. (Solanaceae) forneceu um novo alcaloide esteroidal do tipo espirosolano, caavuranamida, juntamente com os alcaloides 4-tomatiden-3-ona e 5α-tomatidan-3-ona. Suas estruturas foram elucidadas através de métodos espectroscópicos. As atividades antiproliferativa e antimicrobiana para o extrato etanólico e subfrações provenientes de partição e de extração ácido-base foram investigadas. A caavuranamida apresentou atividade antibacteriana similar ao controle positivo cloranfenicol contra Rhodococcus equi.Phytochemical investigation of the ripe fruits of Solanum caavurana Vell. (Solanaceae) afforded a novel steroidal alkaloid with spirosolane-type skeleton, named as caavuranamide, together with the alkaloids 4-tomatiden-3-one and 5α-tomatidan-3-one. Their structures were elucidated on the basis of spectroscopic methods. The antiproliferative and antimicrobial activities for the ethanolic extract, sub-fractions obtained from partition and acid-base treatment were also evaluated. Caavuranamide showed antibacterial activity similar to the chloramphenicol positive control against Rhodococcus equi.

In vitro Antiproliferative and Antibacterial Activities of Essential Oils from Four Species of Guatteria

“…Using the concentration‐response curve for each cell line, the TGI was determined by nonlinear regression analysis using the software ORIGIN 7.5 ( OriginLab Corporation ). [ ][ ] The experiments were performed in triplicate.…”

“…Gram-negative: Salmonella choleraesuis (ATCC 10708), and Pseudomonas aeruginosa (ATCC 13388). The antimicrobial effect was evaluated by using the broth microdilution method previously described in Vaz et al [23] Inocolum for the assays was prepared by diluting a cell mass in a 0.85% NaCl solution and adjusting to the McFarland scale of 0.5 cell suspensions. MIC tests were performed according to CLSI, [24] using Muller-Hinton broth on a tissue-culture test plate (96 wells).…”

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

“…It is comprised of about 2000 species distributed across subtropical and tropical regions of Asia [ 3 – 9 ], tropical Africa [ 10 – 29 ], non-arid Africa [ 30 – 43 ], Americas [ 44 – 87 ], Australia [ 71 – 74 , 81 – 84 ] and India [ 71 ]. The genus is well represented in Brazil with about 350 species widely distributed from north to south in diverse phytogeographic regions [ 70 , 80 ]. In Brazil (Ceará, Bahia, Mato Grosso do Sul, Paraná and north-central coast of Santa Catarina State), many Solanum species, usually known as ‘yubeba’, the word that refers to the prickles found on the stems of several of the species, are widely used in traditional medicine [ 66 , 80 , 87 ].…”

Can the Cure for Chagas’ Disease be Found in Nature?

“…In Solanaceae family, distributed in tropical and subtropical regions of Americas, Africa, and Australia, the genus Solanum is the most representative comprising about 1400 species [18]. The glycoalkaloids (Figure 7) solamargine (18) and solasonine (19) are the typical metabolites of Solanum genus; however, several other classes of compounds, such as flavonoids, phenolic acids, steroids, tannins, and triterpenes, were also recognized.…”

“…C. annua is a perennial herb that grows in American tropical areas and is broadly used in traditional medicine. Previous examination of this plant has led to the isolation of montbretol derivative (22) which showed trypanocidal activity against trypomastigote (IC 50 = 25 μM) and epimastigote (IC 50 = 69 μM) forms of T. cruzi [18]. Some semi-synthetic abietane-type diterpenoids isolated from Plectranthus barbatus Andrews (boldo de jardim), Dracocephalum komarovii Lipsky, Salvia cilicica Boiss, and Juniperus procera Hochst.…”