51847-59-7Relevant academic research and scientific papers
Biotransformation of ent-kaur-16-ene and ent-trachylobane 7β-acetoxy derivatives by the fungus Gibberella fujikuroi (Fusarium fujikuroi)
Fraga, Braulio M.,Bressa, Carlo,González-Vallejo, Victoria,González, Pedro,Guillermo, Ricardo
, p. 60 - 70 (2012/10/08)
Candol A (7β-hydroxy-ent-kaur-16-ene) (6) is efficiently transformed by Gibberella fujikuroi into the gibberellin plant hormones. In this work, the biotransformation of its acetate by this fungus has led to the formation of 7β-acetoxy-ent-kaur-16-en-19-oic acid (3), whose corresponding alcohol is a short-lived intermediate in the biosynthesis of gibberellins and seco-ring ent-kaurenoids in this fungus. Further biotransformation of this compound led to the hydroxylation of the 3β-positions to give 7β-acetoxy-3β- hydroxy-ent-kaur-16-en-19-oic acid (14), followed by a 2β- or 18-hydroxylation of this metabolite. The incubation of epicandicandiol 7β-monoacetate (7β-acetoxy-18-hydroxy-ent-kaur-16-ene) (10) produces also the 19-hydroxylation to form the 18,19 diol (20), which is oxidized to give the corresponding C-18 or C-19 acids. These results indicated that the presence of a 7β-acetoxy group does not inhibit the fungal oxidation of C-19 in 7β-acetoxy-ent-kaur-16-ene, but avoids the ring B contraction that leads to the gibberellins and the 6β-hydroxylation necessary for the formation of seco-ring B ent-kaurenoids. The biotransformation of 7β-acetoxy-ent- trachylobane (trachinol acetate) (27) only led to the formation of 7β-acetoxy-18-hydroxy-ent-trachylobane (33).
DITERPENES FROM SIDERITIS SVENTENII AND S. CYSTOSIPHON
Fraga, Braulio M.,Hernandez, Melchor G.,Santana, Jose M. H.,Arteaga, Jose M.
, p. 591 - 594 (2007/10/02)
The new diterpenes, 7β-monoacetate of episinfernal, 7β-monoacetate of sideritriol, and sventenic acid, have been isolated from Sideritis sventenii.From S. cystosiphon, three new diterpenic esters, the 7β-acetate,18-palmitate of epicandicandiol, the 18-acetate of epicandicandiol, and the 7β,17-diacetate of sideritriol, have been obtained.
Didymooblongin, a New Kaurenoid Diterpene from Didymocarpus oblonga Wall.
Mitra, S. R.,Das, A. K.,Kirtaniya, C. L.,Adityachaudhury, N.,Patra, A.,Mitra, A. K.
, p. 79 - 80 (2007/10/02)
Didymooblongin (III), a new kaurenoid diterpene isolated from the whole plant of Didymocarpus oblonga, has been formulated as 7β-hydroxy-(-)-16-kaurene-19-oic acid (III) on the basis of spectral and chemical evidences.
