Stemodane and stemarane diterpenoid hydroxylation by Mucor plumbeus and Whetzelinia sclerotiorum

Chen, Avril R.M.; Ruddock, Peter L.D; Lamm, Andrew S.; Reynolds, William F.; Reese, Paul B.

doi:10.1016/j.phytochem.2005.06.015

Cited by 22 publications

(20 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…M. plumbeus is known to biotransform ent-kaurene diterpenes such as epicandicandiol and candicandiol, [15] as well as the abietane diterpenoids known as dehydroabietanol and teideadol. [16] In the same manner, for the diterpene (s): labdanes, [12] stemodanes, [17,24] stemarin, [24] and ribenone. [25] Tyrosol has been reported from cultures of G. fujikuroi, Ceratocystis sp., and from a marine strain of Bacillus subtilis KMM3427 associated with sea sponge Verongia sp.…”

Section: Resultsmentioning

confidence: 99%

Microbial transformation of the diterpene mulin‐11,13‐dien‐20‐oic acid by Mucor plumbeus

Areche

Loyola

Bórquez

et al. 2008

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

Two new mulinane-type derivatives: 16-hydroxy mulin-11,13-dien-20-oic (2) acid and 7alpha,16-dihydroxy mulin-11,13-dien-20-oic (3) acid were obtained by microbial transformation of mulin-11,13-dien-20-oic acid (1), along with tyrosol (4) using liquid cultures of Mucor plumbeus. The latter compound has not been previously identified in the genus Mucor. Structural elucidation of these metabolites was achieved using 1D- and 2D-NMR spectroscopy.

show abstract

Section: Resultsmentioning

confidence: 99%

Microbial transformation of the diterpene mulin‐11,13‐dien‐20‐oic acid by Mucor plumbeus

Areche

Loyola

Bórquez

et al. 2008

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

show abstract

“…They comprise the biotransformation of stemodine by Rhizopus oryzae [13], the transformation of isosteviol by Aspergillus niger, Glomerella cingulata and Mortierella elongata [14], biotransformation of baccatin and 1β -hydroxybaccatin I with Aspergillus niger [15], microbial transformation of a pimarane derivative with Gibberella fujikuroi [16], dehydroabietanol and teideadiol by Mucor plumbeus [17], stemodin and several Stemodia diterpenes with Aspergillus niger [18], Mucor plumbeus and Whetzelinia sclerotiorum [19].…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of Jatrophone by Aspergillus niger ATCC 16404

Pertino

Schmeda‐Hirschmann

Santos

et al. 2007

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

Biotransformation of the diterpene jatrophone (1) by Aspergillus niger ATCC 16404 afforded the new diterpene 9β -hydroxyisabellione (2). The compounds were characterized by spectroscopic analysis. The cytotoxicity of the compounds as IC 50 values on AGS and lung fibroblasts was 2.4 and 2.8 µ M for compound 1 and 53.1 and 260 µ M for 2, respectively. Microbial transformation of 1 into compound 2 strongly reduced the cytotoxicity and enhanced the selectivity against AGS cells.

show abstract

“…The NMR spectral data of compound 2 are summarized in the Table 1. Among the several recently reported diterpene biotransformations by A. niger [9,11,12], only in the bioconversion of isoesteviol, in which the 1α,7α-dihydroxy derivative is obtained, was the 1α position hydroxylated [13]. Related compounds with an additional OH function include 3,15-dihydroxy-8(17)-labden-19-oic acid from Juniperus thurifera [14,15], the 6,15-dihydroxyderivative from Viburnum suspensum [16] and 7α-hydroxy-8(17)labdene-15,18-dioic acid from Haplopappus pulchellus [17].…”

Section: Resultsmentioning

confidence: 99%

“…They include the biotransformation of stemodine by Rhizopus oryzae [3], the transformation of isosteviol by Aspergillus niger, Glomerella cingulata and Mortierella elongata [4], transformation of baccatin and 1β-hydroxybaccatin I with Aspergillus niger [5], microbial transformation of a pimarane derivative with Gibberella fujikuroi [6], of dehydroabietanol and teideadiol by Mucor plumbeus [7], stemodin and several Stemodia diterpenes with Aspergillus niger [8], Mucor plumbeus and Whetzelinia sclerotiorum [9].…”

Section: Introductionmentioning

confidence: 99%

Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

et al. 2007

View full text Add to dashboard Cite

Microbial transformation of imbricatolic acid (1) by Aspergillus niger afforded 1α-hydroxyimbricatolic acid (2), while transformation with Rhizopus nigricans yielded 15-hydroxy-8,17-epoxylabdan-19-oic acid (3). When the diterpene 1 was added to a Cunninghamella echinulata culture, the main products were the microbial metabolites mycophenolic acid (4) and its 3-hydroxy derivative 5. All the structures were elucidated by spectroscopic methods. The cytotoxicity of these compounds towards human lung fibroblasts and AGS cells was assessed. While 4 and 5 showed low cytotoxicity, with IC 50 values > 1000 µM against AGS cells and fibroblasts, 1α-hydroxyimbricatolic acid (2) presented moderate toxicity towards these targets, with IC 50 values of 307 and 631 µM, respectively. The structure of 2 is presented for the first time.

show abstract

Stemodane and stemarane diterpenoid hydroxylation by Mucor plumbeus and Whetzelinia sclerotiorum

Cited by 22 publications

References 21 publications

Microbial transformation of the diterpene mulin‐11,13‐dien‐20‐oic acid by Mucor plumbeus

Microbial transformation of the diterpene mulin‐11,13‐dien‐20‐oic acid by Mucor plumbeus

Biotransformation of Jatrophone by Aspergillus niger ATCC 16404

Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

Contact Info

Product

Resources

About