Microbial Transformations of 6α- and 6β-Eudesmanolides by Rhizopus nigricans Cultures

García, Yolanda; Garcı́a-Granados, Andrés; Martı́nez, Antonio; Parra, Andrés; Rivas, Francisco; Arias, J. M.

doi:10.1021/np50124a004

Cited by 10 publications

(7 citation statements)

References 18 publications

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“…These spectroscopic data closely resemble those of 1β,3β-dihydroxy-eudesman-6α,12-olide (2), which was also isolated and identified in this study (Garcia et al, 1995). In the HMBC spectrum, correlations between H-13 (δ H 5.46 and 5.98) and the methine carbon C-7 at δ 42.8, and between the methine proton at δ H 2.48 and two exo-methylene carbons (δ C 141.8 and 117.1, C-11 and 13), indicated that the exo-methylene was located at C-11 of 1.…”

Section: Resultssupporting

confidence: 84%

“…The subfraction TME20 (0.5 g) was subjected to Sephadex LH-20 column chromatography and eluted with MeOH -14), 12.7 (C-13), 9.2 (C-15). 1 H-and 13 C-NMR data were consistent with the literature values (Garcia et al, 1995).…”

Section: Extraction and Isolationsupporting

confidence: 89%

“…In addition, other two compounds were identified as 1β,3β-dihydroxy-eudesman-6α,12-olide (2) (Garcia et al, 1995) and loliolide (3) (Kimura and Maki, 2002) by interpreting spectral data and making comparisons with literature values.…”

Section: Resultsmentioning

confidence: 99%

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Eudesmanolides from Taraxacum mongolicum and their inhibitory effects on the production of nitric oxide

et al. 2011

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A new eudesmanolide, 1β,3β-dihydroxy-eudesman-11(13)-en-6α,12-olide (1) was isolated and identified from Taraxacum mongolicum, together with two known compounds, 1β,3β-dihydroxyeudesman-6α,12-olide (2) and loliolide (3). The structure of 1 was established by analysis of its physical and spectroscopic data. 1 was found to have an inhibitory activity on nitric oxide production with an IC(50) of 38.9 μM in activated RAW 264.7 cells.

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Section: Resultssupporting

confidence: 84%

Section: Extraction and Isolationsupporting

confidence: 89%

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Eudesmanolides from Taraxacum mongolicum and their inhibitory effects on the production of nitric oxide

et al. 2011

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“…427 The microbiological transformations of 7a-hydroxyfrullanolide 428 and 11,13-dehydrosantonin 429 by Aspergillus niger have been reported. The microbial transformations of 6a-and 6b-eudesmanolides by cultures of the fungus Rhizopus nigricans have been examined, 430 and the microbiological transformation of a-santonin by several fungi has been studied. 431 A biomimetic synthesis of the bisesquiterpene lactones (±)biatractylolide and (±)-biepiasterolide has been accomplished.…”

Section: Eudesmane Carboxylic Acidsmentioning

confidence: 99%

Eudesmane sesquiterpenoids from the Asteraceae family

2006

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“…3 Eudesmane sesquiterpenes are common in nature, 4,5 and in the past decade, several biotransformations of these kinds of compounds have been carried out to acquire products difficult to achieve by chemical means. [6][7][8][9][10][11][12][13][14][15][16] Cryptomeridiol is a natural sesquiterpene diol 17 that exerts a potent antispasmodic effect on the isolated rabbit ileum, 18 and 4-epi-cryptomeridiol is also a natural compound. 19 Sesquiterpene lactones show a wide variety of remarkable biological activities, but many of them present strong cytotoxic properties, apparently due to the R, -unsaturated lactone group.…”

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confidence: 99%

Chemical-Microbiological Synthesis of Cryptomeridiol Derivatives by Gliocladium roseum: Semisynthesis of 11-Hydroxyeudesmanolides

et al. 2002

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Biotransformations of 4R-and 4 -hydroxyeudesmane derivatives by the filamentous fungus Gliocladium roseum were achieved. Hydroxylation at C-11 was the main action of this microorganism, producing new cryptomeridiol (12 and 14) and 4-epi-cryptomeridiol derivatives (6 and 7), respectively, in good yields. The biotransformation activity of G. roseum toward 4 -hydroxyeudesmane was focused on the isopropyl moiety, but more scattered on the 4R-hydroxylated derivative, acting in both the "A" and "B" rings and the isopropyl group of the molecule. Semisyntheses of 11-hydroxyeudesmanolides from the isolated 11,12-dihydroxylated metabolites were also accomplished and used in assigning the stereochemistry of hydroxylation.Gliocladium roseum CECT 2733, the anamorphic form of Nectria ochroleuca IMI 40022, is a filamentous fungus that has been used previously to hydroxylate the sesquiterpene patchoulol, 1 to biotransform a derivative of the diterpene varodiol, to produce an ent-Ambrox derivative, 2 and to carry out the bioconversion of a 4 -hydroxyeudesmane derivative. 3 Eudesmane sesquiterpenes are common in nature, 4,5 and in the past decade, several biotransformations of these kinds of compounds have been carried out to acquire products difficult to achieve by chemical means. [6][7][8][9][10][11][12][13][14][15][16] Cryptomeridiol is a natural sesquiterpene diol 17 that exerts a potent antispasmodic effect on the isolated rabbit ileum, 18 and 4-epi-cryptomeridiol is also a natural compound. 19 Sesquiterpene lactones show a wide variety of remarkable biological activities, but many of them present strong cytotoxic properties, apparently due to the R, -unsaturated lactone group. 20-23 Some authors suspect that 11-hydroxysesquiterpenolides are the precursors of those compounds, and thus the unsaturated system could be released in small quantities, thereby attenuating the cytotoxic effect. 24 In previous papers 25,26 we reported the incubations of several 4 -hydroxyeudesmane compounds by the filamentous fungi Curvularia lunata ATCC 12017 and Rhizopus nigricans ATCC 10404. The action of these microorganisms was directed mainly toward the isopropyl moiety; specifically, C. lunata was active toward C-12 and R. nigricans to C-11. Some of the best results were achieved on the 6 -acetoxy-1-keto derivative. Also we have described the incubations of some 4R-hydroxylated derivatives, 25,26 but with poor transformation results. Therefore, in this study we have chosen 6 -acetoxy-1-keto derivatives that are 4 -or 4R-hydroxylated to carry out several biotransformations with the microorganism G. roseum. Results and Discussion6 -Acetoxy-4 -hydroxyeudesman-1-one (1) and its 4R-epimer compound (2) were obtained respectively, by Jones' oxidation at C-1, from the natural compounds 3 27 and 4. 28 Incubation of substrate 1 with G. roseum for 9 days yielded the metabolites 5 (3%), 6 (6%), 7 (58%), and 8 (4%).Metabolite 5 had a molecular formula of C 17 H 26 O 5 , which indicated the presence of an additional oxygen atom and the absence of two hydrog...

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Microbial Transformations of 6α- and 6β-Eudesmanolides by Rhizopus nigricans Cultures

Cited by 10 publications

References 18 publications

Eudesmanolides from Taraxacum mongolicum and their inhibitory effects on the production of nitric oxide

Eudesmanolides from Taraxacum mongolicum and their inhibitory effects on the production of nitric oxide

Eudesmane sesquiterpenoids from the Asteraceae family

Chemical-Microbiological Synthesis of Cryptomeridiol Derivatives by Gliocladium roseum: Semisynthesis of 11-Hydroxyeudesmanolides

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