Microbial hydroxylation of natural drimenic lactones

Maurs, Michèle; Azerad, Robert; Cortés, Manuel; Aranda, G.; Delahaye, M.; Ricard, Louis

doi:10.1016/s0031-9422(99)00199-5

Cited by 37 publications

(21 citation statements)

References 16 publications

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“…The converse is true for androstanes (22)(23)(24) with the absence of the 4 moiety in which hydroxylations occurred at equatorial positions instead of the aforementioned axial sites [8a, 12] (Fig. 2).…”

Section: Hydroxylation Of Steroidsmentioning

confidence: 99%

“…This was achieved by binding the smaller sesquiterpene substrates to one side of the active site model [5]. The insect antifeedants confertifolin (61) and isodrimenin (62), for example, were biotransformed by Rhizopus to the C-3 products (80% and 53% respectively) as well as the C-7 hydroxy (13%) metabolite for the latter [22]. Incubation of the sesquiterpenoid ketone 1,1,4-trimethyltricyclo …”

Section: Hydroxylation Of Terpenoidsmentioning

confidence: 99%

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Biotransformation Reactions by Rhizopus spp.

Martin

2010

COC

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The Rhizopus spp., in particular Rhizopus oryzae, are among the most frequently used whole cell biocatalysts. The fungus is known to catalyze the bioconversion of various reactive and non-reactive substrates with high regio-and stereoselectivities. The range of products obtained from these reactions has been attributed to the substrate binding modes within the enzyme's active site. More recently, an active site model has been developed to account for the reported bioconversions. The use of this model will prove useful in future synthetic and biotechnological applications.

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Section: Hydroxylation Of Steroidsmentioning

confidence: 99%

Section: Hydroxylation Of Terpenoidsmentioning

confidence: 99%

Biotransformation Reactions by Rhizopus spp.

Martin

2010

COC

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“…Biotransformation of terpenoids is gaining considerable attention owing to their antibacterial, antitumour, antiviral, anti-infl ammatory and anthelmintic properties, as well as their importance as fragrances or fl avoring agents (Aranda et al 1991;Maurs et al 1999;Abraham et al 2000). As a continuation of our studies on bioactive terpenes, we have recently investigated the biotransformation of various sesquiterpenes by fungal and plant cell cultures (Choudhary et al 2006(Choudhary et al , 2007Musharraf et al 2010).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of 5α-hydroxycaryophylla-4(12),8(13)-diene withCunninghamella elegansandRhizopus stolonifer

Musharraf

Najeeb

Hareem

et al. 2011

Biocatalysis and Biotransformation

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Biotransformation of 5 α -hydroxycaryophylla-4(12),8(13)-diene ( 1 ) was studied with Cunninghamella elegans and Rhizopus stolonifer . Incubation of 1 with C. elegans gave regioselective oxidative addition (hydration) and isomerization at the C-4(12) exocyclic double bond and hydroxylation at C-3 and C-15, and thus provided two polar metabolites, (3 Z ),8(14)-caryophylladiene-5 α ,(11 R )-15-diol ( 2 ) and 3 β ,4 β ,5 α -trihydroxycaryophylla-8(13)-ene ( 3 ). Incubation of 1 with R. stolonifer gave a transannular cyclization reaction and afforded 2 β -methoxyclovan-9-one ( 4 ), clovan-2 β -ol-9-one ( 5 ) and 8-methoxycaryolane-5 α ,13 β -diol ( 6 ). Compounds 3 and 6 are new compounds described here for the fi rst time; their structures were deduced with the help of different spectroscopic techniques.

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“…14 Moreover, it is also used as a biocatalyst for reactions that are difficult to accomplish by strictly chemical means, involving various substrates including natural drimanic lactones, 15,16 terpenes 17,18 and plant growth regulators. 19 The development of novel antifungal agents with activity against A niger is of interest.…”

Section: Introductionmentioning

confidence: 99%

“…11 A niger has other uses; it is used to test the efficacy of preservative treatments due to its ease of visualization and resistance to several antifungal agents, 12 to remove heavy metals from waste water, 13 and in the biodegradation of hexadecane. 14 Moreover, it is also used as a biocatalyst for reactions that are difficult to accomplish by strictly chemical means, involving various substrates including natural drimanic lactones, 15,16 terpenes 17,18 and plant growth regulators. 19 The development of novel antifungal agents with activity against A niger is of interest.…”

Section: Introductionmentioning

confidence: 99%

The antifungal activity and biotransformation of diisophorone by the fungus Aspergillus niger

Kıran

Yildirim

Hanson

et al. 2004

J of Chemical Tech & Biotech

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The microbial transformation of racemic diisophorone was investigated using the plant pathogen Aspergillus niger as a biocatalyst. Incubation of diisophorone with Aspergillus niger gave 8α-hydroxydiisophorone, 10-hydroxydiisophorone and 17-hydroxydiisophorone on the basis of their spectroscopic data including two-dimensional NMR analysis, nOe and an X-ray crystallographic study. The antifungal activity of diisophorone against Aspergillus niger was also examined.

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Microbial hydroxylation of natural drimenic lactones

Cited by 37 publications

References 16 publications

Biotransformation Reactions by Rhizopus spp.

Biotransformation Reactions by Rhizopus spp.

Biotransformation of 5α-hydroxycaryophylla-4(12),8(13)-diene withCunninghamella elegansandRhizopus stolonifer

The antifungal activity and biotransformation of diisophorone by the fungus Aspergillus niger

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