The biotransformation of 18-hydroxy-9-epi-ent-pimara-7,15-diene by Gibberella fujikuroi

Fraga, Braulio M.; Hernández, Melchor G.; González, Pedro; Chamy, Marı́a C.; Garbarino, Juan A.

doi:10.1016/s0031-9422(99)00542-7

Cited by 15 publications

(30 citation statements)

References 9 publications

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“…Other workers previously suggested that biotransformation of AbA can yield 7-hydroxy-AbA (7) or 7,8-epoxyAbA (31). Also, fungal biotransformation of pimaradiene diterpenes, containing a B ring structure with a 7,8 double bond similar to AbA, led mainly to epoxides with the 7,8 double bond plus 7-oxo derivatives (12,13). Fraga et al (12,13) suggested that the 7,8-epoxide rearranged to the 7-ketone by opening of the oxirane ring.…”

Section: Proteome Versus Transcriptomementioning

confidence: 99%

“…Also, fungal biotransformation of pimaradiene diterpenes, containing a B ring structure with a 7,8 double bond similar to AbA, led mainly to epoxides with the 7,8 double bond plus 7-oxo derivatives (12,13). Fraga et al (12,13) suggested that the 7,8-epoxide rearranged to the 7-ketone by opening of the oxirane ring. This mechanism would explain the production of 7-oxo-PaA from AbA in this study, which might be catalyzed by DitU.…”

Section: Proteome Versus Transcriptomementioning

confidence: 99%

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Distinct Roles for Two CYP226 Family Cytochromes P450 in Abietane Diterpenoid Catabolism by Burkholderia xenovorans LB400

et al. 2008

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The 80-kb dit cluster of Burkholderia xenovorans LB400 encodes the catabolism of abietane diterpenoids. This cluster includes ditQ and ditU, predicted to encode cytochromes P450 (P450s) belonging to the poorly characterized CYP226A subfamily. Using proteomics, we identified 16 dit-encoded proteins that were significantly more abundant in LB400 cells grown on dehydroabietic acid (DhA) or abietic acid (AbA) than in succinategrown cells. A key difference in the catabolism of DhA and AbA lies in the differential expression of the P450s; DitU was detected only in the AbA-grown cells, whereas DitQ was expressed both during growth on DhA and during growth on AbA. Analyses of insertion mutants showed that ditQ was required for growth on DhA, ditU was required for growth on AbA, and neither gene was required for growth on the central intermediate

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Section: Proteome Versus Transcriptomementioning

confidence: 99%

Section: Proteome Versus Transcriptomementioning

confidence: 99%

Distinct Roles for Two CYP226 Family Cytochromes P450 in Abietane Diterpenoid Catabolism by Burkholderia xenovorans LB400

et al. 2008

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“…The fungus G. fujikuroi was gracefully provided by Dr. B. Fraga, Natural Products and Agrobiology Institute, CSIC, Canary Islands, Spain. The strain of G. fujikuroi was grown either on solid PDA (potato dextrose agar) or in liquid medium according to Fraga et al 2000. G. fujikuroi was grown on surface culture in petri plates at 26ºC for 5 days on PDA medium (25 ml per flask) comprising potato extract (4 g/L), glucose (20 g/L), and agar (15 g/L).…”

Section: Biotransformation Experiments and Chemical Analysismentioning

confidence: 99%

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Carvajal¹,

Espinoza²,

Caggia³

et al. 2011

Electro Journal of Biotech

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Background: Several studies have shown that (-)-Jasmonic acid, (+)-7-iso-Jasmonic acid and its methyl ester, methyl jasmonate, have anti-cancer activity in vitro and in vivo, exhibiting selective cytotoxicity towards cancer cells. The degree of activity of these molecules is strongly related to their stereochemistry. The biotransformation of known compounds, natural or synthesized, related to interesting biological activities, generates new molecules displaying new improved properties compared with the original ones, increasing its value and providing new more effective products. Therefore, based on the above rationales and observations, in this work a biotransformation protocol to modify the chemical structure of the plant hormone jasmonic acid by using the fungus Gibberella fujikuroi was established. Results: The three jasmonic acid derivatives obtained, 3(S)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (1), 3(R)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (2), 3-Hydroxy-2(S)-(2Z-pentenyl)-cyclopentane-1(S)-acetic acid (3), were tested for cell-growth inhibition activity towards the human cancer epithelial cell line, the oral squamous carcinoma cells (KB). The results obtained show that jasmonic acid derivatives (1-3) are active on human cancer cells examined in different concentration ranges, with IC50 value less than of 25 µM. The compound 3, with the same molecular structure of compounds 1 and 2, but with different stereochemistry, was more active confirming that the activity of jasmonate compounds is related to their stereochemistry and to substituents in the cyclopentane ring. In this study, we also tested the potential proapoptotic activity of compound 3, and our data suggest that it, as other jasmonate compounds, is able to trigger apoptotic death in cancer cells. This event may be correlated at an elevation of reactive oxygen species (ROS). Administration of N-acetylcysteine (NAC) prevented compound 3 cytotoxicity. Conclusions: This work shows for the by first time the production of hydroxylated derivatives of JA by biotransformation. The activity observed of these compounds in cancer cells is higher than the observed with JA and is strongly related to its stereochemistry.

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“…5) In an attempt to clarify the orientation of symmetrical dimer 1 by regioselective oxidation, compound 1 was subjected to a microbial transformation studies. The present study describes the isolation and identification of this polar biotransformed metabolite (2).…”

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confidence: 99%

Microbial Transformation of Terreusinone, an Ultraviolet-A (UV-A) Protecting Dipyrroloquinone, by Streptomyces sp.

Lee

Choi

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Selectivity is an essential requirement in the synthetic organic chemistry. The regioselectivity of enzymes even on complex or symmetric molecules without the need of protecting groups is the fundmental strength of biocatalysis. The application of biocatalysis to marine natural products has been shown to be a powerful tool for the generation of new, active, and less toxic derivatives for lead optimization and for establishing the stereostructure and structure-activity relationships (SAR). 1-4)Terreusinone (1), a chiral and symmetrical dimer, is an ultraviolet-A (UV-A) protecting dipyrroloquinone isolated from the marine-derived fungus Aspergillus terreus. 5)In an attempt to clarify the orientation of symmetrical dimer 1 by regioselective oxidation, compound 1 was subjected to a microbial transformation studies. The present study describes the isolation and identification of this polar biotransformed metabolite (2).The marine actinomycete (MFAac18) was isolated from a sample of sea plant Zostera marina collected at Bijin Island, Gyeongnam, using YPG (yeast, peptone, and glucose) agar. The fermentation of the bacterium, isolate MFAac18, was carried out in the presence of a substance, terreusinone (1) by a two-stage fermentation protocol.6,7) The incubation was harvested after five weeks, and the broth was extracted with EtOAc. Chromatography of the extract (75 mg) gave the metabolite, terreusinol (2, 5 mg).Terreusinol (2) was isolated as a red solid. A molecular formula of C 18 H 22 N 2 O 5 , which gave nine degrees of unsaturation, was established by high resolution electron impact mass spectrum (HR-EI-MS) and 13 C-NMR methods. The general features of its UV, IR, and NMR spectra (Table 1) closely resembled those of 1, except that the 1 Hand 13 C-NMR signals were doubled due to the presence of two slightly different side chain units from the regioselective oxidation on a direction of the two side chains.In

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The biotransformation of 18-hydroxy-9-epi-ent-pimara-7,15-diene by Gibberella fujikuroi

Cited by 15 publications

References 9 publications

Distinct Roles for Two CYP226 Family Cytochromes P450 in Abietane Diterpenoid Catabolism by Burkholderia xenovorans LB400

Distinct Roles for Two CYP226 Family Cytochromes P450 in Abietane Diterpenoid Catabolism by Burkholderia xenovorans LB400

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Microbial Transformation of Terreusinone, an Ultraviolet-A (UV-A) Protecting Dipyrroloquinone, by Streptomyces sp.

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