Microbial transformation of 1,9-dideoxyforskolin to forskolin

Nadkarni, S. R.; Akut, P. M.; Ganguli, B. N.; Khandelwal, Y.; Souza, N. J. De; Rupp, R. H.; Fehlhaber, H.‐W.

doi:10.1016/s0040-4039(00)85186-2

Cited by 29 publications

(7 citation statements)

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“…1.9-njdrox4lfbrskolin (22). No extra carbonyl function is shown by the "C-NMR data of 26, the only perturbation being at C(14) and C(15) as compared to 22.…”

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confidence: 90%

“…They are both extracted from the Indian herb Coleus ,forskohlii. Forskolin exhibits a promising potential for the treatment of various diseases [22]. It activates adenylate cyclase and represents a useful tool in the understanding of cyclic AMP-mediated physiological processes [22].…”

mentioning

confidence: 99%

“…Forskolin exhibits a promising potential for the treatment of various diseases [22]. It activates adenylate cyclase and represents a useful tool in the understanding of cyclic AMP-mediated physiological processes [22]. Microbial hydroxylation of 7-0 -deacetyl-l,9-dideoxyforskolin (23) led to 7 -0 -deacetylforskolin (24), whereas 1,9-dideoxyforskolin (22) gave a mixture of 2-hydroxylated derivatives 25 [22].…”

mentioning

confidence: 99%

“…It activates adenylate cyclase and represents a useful tool in the understanding of cyclic AMP-mediated physiological processes [22]. Microbial hydroxylation of 7-0 -deacetyl-l,9-dideoxyforskolin (23) led to 7 -0 -deacetylforskolin (24), whereas 1,9-dideoxyforskolin (22) gave a mixture of 2-hydroxylated derivatives 25 [22]. Tn addition to these microbial oxidations, the potential biological usefulness of this class of polyfunctionalised labdane derivatives prompted the interest of chemists to either perform chemical modifications of these compounds or devise their total syntheses [23].…”

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confidence: 99%

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Functionalisation of saturated hydrocarbons. Part XI. Oxidation of cedrol, β‐ and γ‐eudesmol, sclareol, manoyl oxide, 1,9‐dideoxyforskolin, methyl trans‐dihydroiasmonate, and tetrahydrolinalool by the ‘Gif system’

Barton

Beloeil

Billion

et al. 1987

Helvetica Chimica Acta

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Dedicated to Professor Tadeus Rrichstrin on the occasion of his 90th birthday (10.V11.87)The oxidation of cedrol (l), p-and y-eudesmol(6 and 7, resp.), sclareol(14), manoyl oxide ( 1 3 , 1,9-didcoxyforskolin (22) (+)-methyl trans-dihydrojasmonate (28), and tetrahydrolinalool(32), nearly all of natural terpenoid origin, by the 'Gifsystem' has afforded a number of novel products (3, 11, and 12, 16/17, 18/19, 26, 29-31, and ketones corresponding to 34-35, resp.). The structures of these compounds were established by spectroscopic techniques including 2D-NMR and, wherc appropriate, by comparison with authentic samples.Introduction. -In the preceding parts of this series [l-61, we reported our findings on the oxidation of saturated hydrocarbons by the 'Gifsystem'. This process, especially in its most elaborate form (catalytic amounts of iron cluster Fe,O(OAc),Pyr, 5, Zn powder, AcOH, pyridine, and air at room temperature) was successfully applied to a variety of simple hydrocarbons [2] [3] and then to more complex molecules such as steroids [4] [5] and terpenoids [l] [6]. As a rule, this oxidising system leads to the formation of ketones as major products, i.e. selective attack on secondary positions. This regioselectivity is rather unusual when compared with other oxidising processes. A noticeable exception was observed in the case of cholestane derivatives where the important side-chain cleavage to give 20-ketones competed with the oxidation of the methylenes of the steroidal nucleus [4]

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“…1.9-njdrox4lfbrskolin (22). No extra carbonyl function is shown by the "C-NMR data of 26, the only perturbation being at C(14) and C(15) as compared to 22.…”

mentioning

confidence: 90%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Functionalisation of saturated hydrocarbons. Part XI. Oxidation of cedrol, β‐ and γ‐eudesmol, sclareol, manoyl oxide, 1,9‐dideoxyforskolin, methyl trans‐dihydroiasmonate, and tetrahydrolinalool by the ‘Gif system’

Barton

Beloeil

Billion

et al. 1987

Helvetica Chimica Acta

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“…Forskolin (7β-acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one) is the major diterpenoid from the Indian herb Coleus forskohlii which is its main source as well [191]. Forskolin is a potential drug for treatment of glaucoma, congestive heart failure, and bronchial astma.…”

Section: Microbial Transformations For Providing Information Regardinmentioning

confidence: 99%

Microbial Transformations of Plant Secondary Metabolites

Mutafova¹,

Fernandes²,

Mutafov³

et al. 2016

Bioprocessing of Plant in Vitro Systems

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The aim of this chapter is to present the authors' view on the place and role of microbial transformation reactions as a perspective means of processing of plantderived biologically active compounds into metabolites with new and/or increased activity and availability and decreased toxicity. Some microbial transformations providing information regarding metabolism in humans and mammals of plant-derived secondary metabolites applied as drugs and/or food additives are also considered.

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