88143-06-0Relevant articles and documents
Biotransformation of ent-13-epi-manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi
Garcia-Granados, Andres,Fernandez, Antonia,Gutierrez, Maria C.,Martinez, Antonio,Quiros, Raquel,Rivas, Francisco,Arias, Jose M.
, p. 107 - 115 (2004)
Biotransformation of ent-3β,12α-dihydroxy-13-epi-manoyl oxide with Fusarium moniliforme gave the regioselective oxidation of the hydroxyl group at C-3 and the ent-7β-hydroxylation. The action of Gliocladium roseum in the 3,12-diketoderivative originated monohydroxylations at C-1 and C-7, both by the ent-β face, while Rhizopus nigricans produced hydroxylation at C-7 or C-18, epoxidation of the double bond, reduction of the keto group at C-3, and combined actions as biohydroxylation at C-2/epoxidation of the double bond and hydroxylation at C-7/reduction of the keto group at C-3. In the ent-3-hydroxy-12-keto epimers, G. roseum originated monohydroxylations at C-1 and C-7 and R. nigricans originated the oxidation at C-3 as a major transformation, epoxidation of double bond and hydroxylation at C-2. Finally, in the ent-3β-hydroxy epimer R. nigricans also originated minor hydroxylations at C-1, C-6, C-7 and C-20 and F. moniliforme produced an hydroxylation at C-7 and a dihydroxylation at C-7/C-11.
Chemical-microbiological semisynthesis of enantio-Ambrox derivatives
Garcia-Granados, Andres,Martinez, Antonio,Quiros, Raquel,Extremera, Antonio Luis
, p. 8567 - 8578 (1999)
enantio-3-Hydroxyambrox derivatives were obtained through combined chemical and microbiological methods from ent-12-dioxo-13-epi-manoyl oxides. Regioselective and stereoselective reduction of the carbonyl group at C-3 of ent-3,12-dioxo-13-epi-manoyl oxide was carried out with Baker's yeast. Regioselective acetylation of ent-3,12-dihydroxy-13-epi-manoyl oxide was accomplished with Candida cylindracea lipase or Novozym 435 and vinyl acetate. Microbial biotransformation of ent-3 β-acetoxy-12-oxo-13-epi- manoyl oxide with Neetria ochroleuca yielded new ent-1β-hydroxy- and ent- 7β-hydroxy derivatives. Baeyer-Villiger oxidation at C-12 was observed in the biotransformation with baker's yeast and G. roseun to obtain norambreinolide lactones which were converted in to enantio-Ambrox derivatives.
CHEMICAL-MICROBIOLOGICAL SYNTHESIS OF ENT-13-EPI-MANOYL OXIDES WITH BILOGICAL ACTIVITIES
Garcia-Granados, Andres,Jimenez, M Belinda,Martinez, Antonio,Parra, Andres,Rivas, Francisco,Arias, Jose Maria
, p. 741 - 748 (2007/10/02)
The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6β-hydroxy, ent-1α-hydroxy, ent-11β-hydroxy and Δ1-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6β) or C-11 (ent-11β).The ent-6β-hydroxy and Δ1-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovoni.The biotransformation of ent-12α-hydroxy-3β-hydroxy-13-epi-manoyl oxide and ent-3β-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6β-hydroxyl derivatives.The incubation of ent-3β-acetoxy-12β-dihydroxy-13-epi-manoyl oxide gave ent-3β,12β-dihydroxy-13-epi-manoyl oxide and ent-3β,6β,12β-trihydroxy-13-epi-manoyl oxide (trimanoyl).Both products increased the activity of adenylatecyclase. - Key words: Curvularia lunata; biotransformation; ent-13-epi-manoyl oxides; antileishmanic activity; adenylatecyclase activator.
