Hydroxylation of a hederagenin derived saponin by a Xylareaceous fungus found in fruits of Sapindus saponaria

Abstract

Durante nossos estudos visando a obtenção de microorganismos endofíticos associados a plantas tropicais, um fungo do grupo Xylareaceae foi isolado das partes internas dos frutos de Sapindus saponaria. Os frutos de S. saponaria acumulam grande quantidade de saponinas triterpênicas e sesquiterpênicas. A saponinaarabinopiranosil-hederagenina foi isolada por métodos cromatográfios após saponificação do extrato bruto obtido dos frutos de S. saponaria e admistrada junto ao meio de cultivo usado para crescimento do fungo. Após extração dos metabólitos obtidos, uma nova saponina foi purificada por CLAE em escala preparativa e caracterizada como um derivado 22 -hidroxilado. Essa saponina hidroxilada teve sua estrutura molecular elucidada através da interpretação de dados de EM/EM e RMN.During our screening of tropical plants for endophyte microorganisms, a Xylareaceous fungus was found living on the internal part of Sapindus saponaria fruits. The fruits of S. saponaria accumulate great amounts of triterpenoidal and sesquiterpenoidal saponins. The saponin 3-O-( -D-xylopyranosyl)-(1 3)--L-rhamnopyranosyl-(1 2)--L-arabinopyranosyl-hederagenin was isolated using chromatographic methods, after alkaline hydrolysis of the crude extract obtained from S. saponaria fruits and added to the culture medium used to grows the fungus. A new saponin was isolated from this experiment by preparative scale HPLC and characterized as a 22 -hydroxy derivative. The structure of this hydroxylated saponin was elucidated based on interpretation of MS/MS data and NMR spectra.

Spermicidal and anti-Trichomonas vaginalis activity of Brazilian Sapindus saponaria

“…The structures were established by spectroscopic methods ( 1 H and 13 C NMR, HSQC, HMBC, and ESI/MS) and by comparing them with literature data [8,10]. …”

“…The fruit of Sapindus saponaria L. (Sapindaceae), a medium-sized tropical tree, is used by population as soap for washing clothes, and for curing ulcers, external wounds and inflammations [7]. Scientific works has shown antimicrobial activity [8-10], but has been little studied. In a recent study, members of our research group isolated and identified the principal constituents of the n-BuOH saponins, saponins (S1 and S2), and also an acyclic oligoglycoside.…”

In vivo activity of Sapindus saponaria against azole-susceptible and -resistant human vaginal Candida species

“…The fruit of Sapindus saponaria L. (Sapindaceae), a medium-sized tropical tree found principally in America and India, has shown antimicrobial activity [2-4], but few studies have been carried out with this plant.…”

Candida albicans PROTEIN PROFILE CHANGES IN RESPONSE TO THE BUTANOLIC EXTRACT OF Sapindus saponaria L.

“…Species from the Sapindaceae family are known for their traditional medicinal use as diuretics, stimulants, expectorants, natural surfactants, sedatives, and vermifuges and for their use in the treatment of stomachaches and dermatitis in many parts of the world 3 . Sapindus saponaria L. (Sapindaceae), popularly known as "sabão-de-soldado" and "saboeiro", is a medium-sized deciduous tree that occurs in the tropics of the Americas and India, where the fruit is used as a soap and as a medicine against ulcers, scabies, joint pain, inflammation 4 , 5 , 6 , 7 and skin lesions caused by fungi 8 . Sapindus saponaria is a potential candidate for the treatment of candidiasis in vitro and in vivo 9 , 10 , 11 .…”