Terpenoids and Steroids from Trichilia Species

Abstract

O trabalho descreve o isolamento de três novos sesquiterpenóides do extrato metanólico dos galhos de Trichilia claussenii: 14-hidroxielemol, germacra-10(14)-en-9,11,15-triol e germacra-3,10(14)-dien-9,11-diol-4-carbaldeído. Também foram isolados os sesquiterpenos β-eudesmol, criptomeridiol e o triterpeno 22,25-diidroxi-9β,19-ciclolanost-23-en-3-ona. Do extrato diclorometânico das folhas de T. lepidota foram isolados mistura de hidrocarbonetos (C 29 H 60 , C 31 H 64 e C 33 H 68 ), mistura dos sesquiterpenos epóxido de cariofileno e epóxido de humuleno, espatulenol e os esteróides 24-metileno-12β-hidroxicolesterol, 24-metil-12β-hidroxicolest-4-en-3-ona, 3-palmitato de 24-metil-12β-hidroxicolest-5-eno, mistura de 24-metilenocolesterol, campesterol, estigmasterol e β-sitosterol, além de α-tocoferol e fitol. O extrato metanólico forneceu a N-metil-4-hidroxiprolina. As estruturas das substâncias isoladas foram estabelecidas com base em dados espectroscópicos.The methanol extract of stems of Trichilia claussenii yielded three new sesquiterpenoids: 14-hydroxyelemol, germacra-10(14)-en-9,11,15-triol and germacra-3,10(14)-dien-9,11-diol-4-carbaldehyde. Two known sesquiterpenoids β-eudesmol, cryptomeridiol and the triterpenoid 22,25-dihydroxy-9β,19-cyclolanost-23-en-3-one were also isolated. The dichloromethane extract from the leaves of T. lepidota afforded a mixture of hydrocarbons (C 29 H 60 , C 31 H 64 and C 33 H 68 ), a mixture of the sesquiterpenes caryophyllene and humulene epoxides, spathulenol, and a series of sterols: 24-methylene-12β-hydroxycholesterol, 24-methyl-12β-hydroxycholest-4-en-3-one, 24-methylene-12β-hydroxycholest-5-ene-3-palmitate; a mixture of 24-methylenecholesterol, campesterol, stigmasterol and β-sitosterol; besides α-tocoferol and phytol. From the methanol extract it was isolated N-methyl-4-hydroxyproline. The structures of the isolated compounds were determined on the basis of spectroscopic analysis.

Phenylpropanoid substituted flavan-3-ols from Trichilia catigua and their in vitro antioxidative activity

“…3 Other species, T. claussenii and T. lepidota, were evaluated and yielded sesquiterpenoids. 12 We further investigated the constituents of T. catigua bark and isolated nine polyphenolic constituents, including one new compound. The isolated polyphenols showed high radical scavenging and antioxidative activity in DPPH (2,2-diphenyl-1-picryl-hydrazyl) and Fe 3+ -Fe 2+ assays.…”

Secondary Metabolites of the Genus Trichilia: Contribution to the Chemistry of Meliaceae Family

“…The Trichilia genus consists of about 70 species, mainly distributed in tropical America and Africa, of which 43 species occur in Brazil [5][6][7][8].…”

Lepidotrichilins A and B, New Protolimonoids with Cytotoxic Activity from Trichilia Lepidota (Meliaceae)

“…The Trichilia genus consists of about 230 species distributed throughout tropical America and other countries ranging from Africa and Asia [2,3]. Previous investigations on the chemical constituents of the dichloromethane extract from the leaves of this species revealed the presence of hydrocarbons mixtures (C 29 H 60 , C 31 H 64 and C 33 H 68 ), sesquiterpenes, steroids, amino acids and other compounds derived from the terpene metabolic pathway [4].…”