“…However, a chemical shift of H-7 (δ H 3.76) and δ C 72.9 for C-7 and δ C 76.0 for C-8 suggested that the alkene underwent a dihydroxylation. Structural assignment of isolated compounds 2 - 6 was further supported by comparison of analytical data with literature reports (compound 2 : Marasmius oreades 30 , compound 3 : Clitocybe conglobate 31 , compound 4 : Phellinidium sulphurascens 32 , compound 5 : Peniophora polygonia 33 , compound 6 : synthesis of stereoisomers 34 , 35 and synthetic derivatives ( vide infra ). Fig.…”
Macrotermitinae termites have farmed fungi in the genus Termitomyces as a food source for millions of years. However, the biochemical mechanisms orchestrating this mutualistic relationship are largely unknown. To deduce fungal signals and ecological patterns that relate to the stability of this symbiosis, we explored the volatile organic compound (VOC) repertoire of Termitomyces from Macrotermes natalensis colonies. Results show that mushrooms emit a VOC pattern that differs from mycelium grown in fungal gardens and laboratory cultures. The abundance of sesquiterpenoids from mushrooms allowed targeted isolation of five drimane sesquiterpenes from plate cultivations. The total synthesis of one of these, drimenol, and related drimanes assisted in structural and comparative analysis of volatile organic compounds (VOCs) and antimicrobial activity testing. Enzyme candidates putatively involved in terpene biosynthesis were heterologously expressed and while these were not involved in the biosynthesis of the complete drimane skeleton, they catalyzed the formation of two structurally related monocyclic sesquiterpenes named nectrianolins.
“…However, a chemical shift of H-7 (δ H 3.76) and δ C 72.9 for C-7 and δ C 76.0 for C-8 suggested that the alkene underwent a dihydroxylation. Structural assignment of isolated compounds 2 - 6 was further supported by comparison of analytical data with literature reports (compound 2 : Marasmius oreades 30 , compound 3 : Clitocybe conglobate 31 , compound 4 : Phellinidium sulphurascens 32 , compound 5 : Peniophora polygonia 33 , compound 6 : synthesis of stereoisomers 34 , 35 and synthetic derivatives ( vide infra ). Fig.…”
Macrotermitinae termites have farmed fungi in the genus Termitomyces as a food source for millions of years. However, the biochemical mechanisms orchestrating this mutualistic relationship are largely unknown. To deduce fungal signals and ecological patterns that relate to the stability of this symbiosis, we explored the volatile organic compound (VOC) repertoire of Termitomyces from Macrotermes natalensis colonies. Results show that mushrooms emit a VOC pattern that differs from mycelium grown in fungal gardens and laboratory cultures. The abundance of sesquiterpenoids from mushrooms allowed targeted isolation of five drimane sesquiterpenes from plate cultivations. The total synthesis of one of these, drimenol, and related drimanes assisted in structural and comparative analysis of volatile organic compounds (VOCs) and antimicrobial activity testing. Enzyme candidates putatively involved in terpene biosynthesis were heterologously expressed and while these were not involved in the biosynthesis of the complete drimane skeleton, they catalyzed the formation of two structurally related monocyclic sesquiterpenes named nectrianolins.
Four new sesquiterpenoids, namely 12-hydroxy-3-oxodrimenol (1), 11-hydroxyacetoxydrim-7-en-3β-ol (2), 2,6-dimethyl-7,10-epoxy-10-hydroxymethyldodeca-2,11-dien-6-ol (3), and 7,10-epoxy-2,6,10-trimethyldodeca-2,11-diene-4,6-diol (4), along with fourteen known compounds, were isolated from the cultures of Phellinidium sulphurascens. The structures of compounds 1–4 were established on the basis of extensive spectroscopic analysis. All of them were evaluated for their cytotoxic activities.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-014-0047-x) contains supplementary material, which is available to authorized users.
“…This stereochemistry is explained by considering el steric hindrance caused by the acetate group, redirecting below the epoxidation reactions. Additionally shifts of C-8 and C-9 in compound 12 were compared with a compound of similar structure [ 23 ].…”
Natural compounds from Drimys winteri Forst and derivatives exhibited larvicidal effects against Drosophila melanogaster til-til. The most active compound was isodrimenin (4). The highest lethal concentration to the larvae of D. melanogaster was 4.5 ± 0.8 mg/L. At very low concentrations drimenol (1), confertifolin (3), and drimanol (5) displayed antifeedant and larvae growth regulatory activity. The antifeedant results of nordrimanic and drimanic compounds were better in first instar larvae. The EC50 value of polygodial (2) was 60.0 ± 4.2 mg/L; of diol 15 45.0 ± 2.8 mg/L, and of diol 17 36.9 ± 3.7 mg/L, while the new nordrimane compound 12 presented a value of 83.2 ± 3.5 mg/L.
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