Secondary biotransformation of 11β-hydroxy-dianabol (11β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one) (1), catalyzed by using two fungi Gibberella fujikuroi and Cunninghamella blakesleeana at ambient conditions, was carried out to synthesize its analogues. Transformation of compound 1 with G. fujikuroi yielded a new metabolite, 11β, 17β-dihydroxy-17α-methyl-5β-androst-1-ene-3-one (2), while four new derivatives, 6β, 17β-dihydroxy-17α-methylandrost-1,4-diene-3,11-dione (3), 15α,17β-dihydroxy-17α-methylandrost-1,4-diene-3,11-dione (4), 6β,11β,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one (5), and 7β,11β,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one (6) were obtained by transformation with C.
View Article and Find Full Text PDFBackground: Drug repurposing in oncology promises benefits to many patients through its ability to provide novel, and fast-tracked treatments. Previous studies have demonstrated that depression may influence tumor progression. Anti-proliferative activity of certain antidepressants, mainly selective serotonin reuptake inhibitors (SSRIs), are reported in the literature.
View Article and Find Full Text PDFVanillic acid (VA) - a naturally occurring phenolic compound in plants - is not only used as a flavoring agent but also a prominent metabolite post tea consumption. VA and its associated compounds are believed to play a significant role in preventing diseases, underscoring the need for a systematic investigation. Herein, we report a 4-step synthesis employing the classical organic reactions, such as Willamson's alkylation, Fischer-Spier reaction, and Steglich esterification, complemented with a protection-deprotection strategy to prepare 46 VA derivatives across the five series (1a-1i, 2a-2i, 3, 3a-3i, 4a-4i, 5a-5i) in high yields.
View Article and Find Full Text PDFA synthetic anabolic-androgenic steroid, methylstenbolone (1), was structurally transformed into a series of nine analogues, 2,17α-dimethyl-7α,17β-dihydroxy-5α-androst-1-en-3-one (2), 2,17α-dimethyl-15β,17β-dihydroxy-5α-androst-1-en-3-one (3), 2,17α-dimethyl-6α,9α,17β-trihydroxy-5α-androst-1-en-3-one (4), 2-methyl-17β-hydroxy-17α-(hydroxymethyl)-5α-androst-1-en-3-one (5), 2-methyl-11β,17β-dihydroxy-17α-(hydroxymethyl)-5α-androst-1-en-3-one (6), 2-methyl-17β-hydroxy-17α-(hydroxymethyl)-5α-androst-1-en-3,6-dione (7), 2-methyl-17β-hydroxy-17α-(hydroxymethyl)-5β-androst-1-en-3,6-dione (8), 2,17α-dimethyl-7β,17β-dihydroxy-5α-androst-1-en-3-one (9), and 2,17α-dimethyl-12β,17β-hydroxy-5α-androst-1-en-3,7-dione (10) by fungal cell suspension cultures, Macrophomina phaseolina and Cunninghamella blakesleeana for the first time. Among those, compounds 2-4 and 6-10 were identified as new. Herein, spectral data of metabolite 5 was reported for the first time.
View Article and Find Full Text PDFA new clerodane diterpene, named 6α-hydroxy-3,13E-clerodien-15-oic acid (1), together with a known clerodane diterpene (2), four known labdane diterpenes (3-6), a triterpenoid (7), a known steroid (8), and two benzenoid compounds (9 and 10) were isolated from Detarium microcarpum Guill. & Perr. The structures of all obtained compounds were determined by chemical properties and spectroscopic evidence, accompanied by comparisons with data in the literature.
View Article and Find Full Text PDFA new sesquiterpene (Prosoterpene, ) and eleven reported compounds (-) of several classes, such as flavonoids, alkaloids, phenolic acids, and long-chain alcohols, were isolated from the BuOH extract of (Guill. & Perr.) Taub.
View Article and Find Full Text PDFSix 5(14)-membered ring type of cyclopeptide alkaloids (CPAs), including two undescribed members, 1-hydro,2β-methoxy-mauritine-A () and 1-hydro,2α-methoxy-mauritine-A (), together with four known compounds, mauritine-A (), mauritine C (), amphibine-A (), and amphibine-E (), were isolated from the root bark of (L.) Desf., Their structures were determined by multiple spectral analyses, including UV, IR, 1D NMR, 2D NMR, EI-MS, HR-EI-MS, FAB-MS and ESI-MS, and by comparison with literature.
View Article and Find Full Text PDFTwo new ursane-type triterpenoids, named Polyanside A () and B (), along with eleven known compounds (-), were isolated and elucidated from (Benth.) Prance. The structures of these compounds were elucidated based on chemical evidence and multiple spectroscopic data.
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