Cunninghamella

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Iqbal M. Choudhary - One of the best experts on this subject based on the ideXlab platform.

  • a new metabolite from Cunninghamella blakesleeana mediated biotransformation of an oral contraceptive drug levonorgestrel
    Natural Product Research, 2019
    Co-Authors: Bates Malikovna Kudaibergenova, Mahwish Siddiqui, Atia-tul- Wahab, Iqbal M. Choudhary, Zharylkasyn A Abilov
    Abstract:

    Cunninghamella blakesleeana-mediated biotransformation of an oral contraceptive drug, levonorgestrel (1), yielded a new metabolite, 13β-ethyl-17α-ethynyl-10,17β-dihydroxy-4,6-dien-3-one (2), and two known metabolites 3 (13β-ethyl-17α-ethynyl-10β,17β-dihydroxy-4-en-3-one), and 4 (13β-ethyl-17α-ethynyl-6β,17β-dihydroxy-4-en-3-one) at an ambient temperature using aqueous media. Hydroxylation and dehydrogenation of compound 1 was observed during the bio-catalytic transformation. The structure of a new metabolite 2 was determined by 1H, 13C, and 2DNMR and HR-EIMS spectroscopic techniques.

  • Compounds 2–4 obtained by the biotransformation of mibolerone (1) with Cunninghamella blakesleeana and C. echinulata.
    2017
    Co-Authors: Mahwish Siddiqui, Malik Shoaib Ahmad, Atia-tul- Wahab, Samme Yousuf, Narjis Fatima, Nimra Naveed Shaikh, Atta-ur- Rahma, Iqbal M. Choudhary
    Abstract:

    Compounds 2–4 obtained by the biotransformation of mibolerone (1) with Cunninghamella blakesleeana and C. echinulata.

  • microbial transformation of contraceptive drug etonogestrel into new metabolites with Cunninghamella blakesleeana and Cunninghamella echinulata
    Steroids, 2016
    Co-Authors: Elias Baydoun, Malik Shoaib Ahmad, Atia-tul- Wahab, Iqbal M. Choudhary, Nayab Shoaib, Roula M Abdelmassih, Colin A Smith, Nimra Naveed
    Abstract:

    Biotransformation of a steroidal contraceptive drug, etonogestrel (1), (13-ethyl-17β-hydroxy-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-3-one) was investigated with Cunninghamella blakesleeana and C. echinulata. Five metabolites 2-6 were obtained on incubation of 1 with Cunninghamella blakesleeana, and three metabolites, 2, 4, and 6 were isolated from the transformation of 1 with C. echinulata. Among them, metabolites 2-4 were identified as new compounds. Their structures were deduced as 6β-hydroxy-11,22-epoxy-etonogestrel (2), 11,22-epoxy-etonogestrel (3), 10β-hydroxy-etonogestrel (4), 6β-hydroxy-etonogestrel (5), and 14α-hydroxy-etonogestrel (6). Compounds 1-6 were evaluated for various biological activities. Interestingly, compound 5 was found to be active against β-glucuronidase enzyme with IC50 value of 13.97±0.12μM, in comparison to standard compound, d-saccharic acid 1,4-lactone (IC50=45.75±2.16μM). Intestinal bacteria produce β-glucuronidase. Increased activity of β-glucuronidase is responsible for the hydrolyses of glucuronic acid conjugates of estrogen and other toxic substances in the colon, which plays a key role in the etiology of colon cancer. Inhibition of β-glucoronidase enzyme therefore has a therapeutic significance. Compounds 1-6 were also found to be non cytotoxic against 3T3 mouse fibroblast cell lines.

  • microbial transformation of nandrolone with Cunninghamella echinulata and Cunninghamella blakesleeana and evaluation of leishmaniacidal activity of transformed products
    Steroids, 2014
    Co-Authors: Elias Baydoun, Malik Shoaib Ahmad, Iqbal M. Choudhary, Roula M Abdelmassih, Colin A Smith, Martin Karam, Mahwish Shafi Ahmed Khan
    Abstract:

    Therapeutic potential of nandrolone and its derivatives against leishmaniasis has been studied. A number of derivatives of nandrolone (1) were synthesized through biotransformation. Microbial transformation of nandrolone (1) with Cunninghamella echinulata and Cunninghamella blakesleeana yielded three new metabolites, 10b,12b,17b-trihydroxy-19-nor-4-androsten-3-one (2), 10b,16a,17b-trihydroxy-19-nor-4androsten-3-one (3), and 6b,10b,17b-trihydroxy-19-nor-4-androsten-3-one (4), along with four known metabolites, 10b,17b-dihydroxy-19-nor-4-androsten-3-one (5), 6b,17b-dihydroxy-19-nor-4-androsten3-one (6 )1 0b-hydroxy-19-nor-4-androsten-3,17-dione (7) and 16b,17b-dihydroxy-19-nor-4-androsten-3-one (8). Compounds 1–8 were evaluated for their anti-leishmanial activity. Compounds 1 and 8 showed a significant activity in vitro against Leishmania major. The leishmanicidal potential of compounds 1–8 (IC50 = 32.0 ± 0.5, >100, 77.39 ± 5.52, 70.90 ± 1.16, 54.94 ± 1.01, 80.23 ± 3.39, 61.12 ± 1.39 and 29.55 ± 1.14 lM, respectively) can form the basis for the development of effective therapies against the protozoal tropical disease leishmaniasis.

  • fungal metabolites of e guggulsterone and their antibacterial and radical scavenging activities
    Chemistry & Biodiversity, 2005
    Co-Authors: Iqbal M. Choudhary, Adnan Ali S Shah, Amtul Sami, Asma Ajaz, Farzana Shaheen
    Abstract:

    Fungal transformation of (E)-guggulsterone (= (17E)-pregna-4,17-diene-3,16-dione; 1) by Rhizopus stolonifer, Fusarium lini, Cunninghamella elegans, or Gibberella fujikuroi afforded ten hydroxylated metabolites (2-11; Scheme), which were fully characterized. Compounds 4-11 have not been described yet. Some of these novel hydroxylated metabolites, as well as acetylated derivatives thereof, exhibited significant antibacterial and radical-scavenging activities (Table 3).

Da-fang Zhong - One of the best experts on this subject based on the ideXlab platform.

  • Biotransformation of metoprolol by the fungus Cunninghamella blakesleeana
    Acta pharmacologica Sinica, 2007
    Co-Authors: Hai-hua Huang, Xiaoyan Chen, Yuming Sun, Li Hong Lin, Da-fang Zhong
    Abstract:

    Aim: To investigate the biotransformation of metoprolol, a β 1 -cardioselective adrenoceptor antagonist, by filamentous fungus, and to compare the parallels between microbial transformation and mammalian metabolism. Methods: Five strains of Cunninghamella ( C elegans AS 3.156, C elegans AS 3.2028, C echinulata AS 3.2004, C blakesleeana AS 3.153 and AS 3.910) were screened for the ability to transform metoprolol. The metabolites of metoprolol produced by C blakesleeana AS 3.153 were separated and assayed by liquid chromatography-tandem mass spectrometry (LC/MS n ). The major metabolites were isolated by semipreparative HPLC and the structures were identified by a combination of LC/MS n and nuclear magnetic resonance analysis. Results: Metoprolol was transformed to 7 metabolites; 2 were identified as new metabolites and 5 were known metabolites in mammals. Conclusion: The microbial transformation of metoprolol was similar to the metabolism in mammals. The fungi belonging to Cunninghamella species could be used as complementary models for predicting in vivo metabolism and producing quantities of metabolite references for drugs like metoprolol.

  • biotransformation of indomethacin by the fungus Cunninghamella blakesleeana
    Acta Pharmacologica Sinica, 2006
    Co-Authors: Peng Zhang, Da-fang Zhong, Hai-hua Huang, Li Hong Lin
    Abstract:

    Aim: To investigate the biotransformation of indomethacin, the first of the newer nonsteroidal anti-inflammatory drugs, by filamentous fungus and to compare the similarities between microbial transformation and mammalian metabolism of indomethacin. Methods: Five strains of Cunninghamella (C elegans AS 3.156, C elegans AS 3.2028, C blakesleeana AS 3.153, C blakesleeana AS 3.910 and C echinulata AS 3.2004) were screened for their ability to catalyze the biotransformation of indomethacin. Indomethacin was partially metabolized by five strains of Cunninghamella , and C blakesleeana AS 3.910 was selected for further investigation. Three metabolites produced by C blakesleeana AS 3.910 were isolated using semi-preparative HPLC, and their structures were identified by a combination analysis of LC/MS n and NMR spectra. These three metabolites were separated and quantitatively assayed by liquid chromatography-ion trap mass spectrometry. Results: After 120 h of incubation with C blakesleeana AS 3.910, approximately 87.4% of indomethacin was metabolized to three metabolites: O -desmethylindomethacin (DMI, M1, 67.2%), N -deschlorobenzoylindomethacin (DBI, M2, 13.3%) and O -desmethyl- N -deschlorobenzoylindomethacin (DMBI, M3, 6.9%). Three phase I metabolites of indomethacin produced by C blakesleeana AS 3.910 were identical to those obtained in humans. Conclusion: C blakesleeana could be a useful tool for generating the mammalian phase I metabolites of indomethacin.

  • Biotransformation of pantoprazole by the fungus Cunninghamella blakesleeana
    Xenobiotica, 2005
    Co-Authors: Hai-hua Huang, Da-fang Zhong
    Abstract:

    To investigate the biotransformation of pantoprazole, a proton-pump inhibitor, by filamentous fungus and further to compare the similarities between microbial transformation and mammalian metabolism of pantoprazole, four strains of Cunninghamella (C. blakesleeana AS 3.153, C. echinulata AS 3.2004, C. elegans AS 3.156, and AS 3.2028) were screened for the ability to catalyze the biotransformation of pantoprazole. Pantoprazole was partially metabolized by four strains of Cunninghamella, and C. blakesleeana AS 3.153 was selected for further investigation. Three metabolites produced by C. blakesleeana AS 3.153 were isolated using semi-preparative HPLC, and their structures were identified by a combination analysis of LC/MSn and NMR spectra. Two further metabolites were confirmed with the aid of synthetic reference compounds. The structure of a glucoside was tentatively assigned by its chromatographic behavior and mass spectroscopic data. These six metabolites were separated and quantitatively assayed by liqui...

  • transformation of verapamil by Cunninghamella blakesleeana
    Applied and Environmental Microbiology, 2004
    Co-Authors: Lu Sun, Hai-hua Huang, Lei Liu, Da-fang Zhong
    Abstract:

    A filamentous fungus, Cunninghamella blakesleeana AS 3.153, was used as a microbial model of mammalian metabolism to transform verapamil, a calcium channel antagonist. The metabolites of verapamil were separated and assayed by the liquid chromatography-ion trap mass spectrometry method. After 96 h of incubation, nearly 93% of the original drug was metabolized to 23 metabolites. Five major metabolites were isolated by semipreparative high-performance liquid chromatography and were identified by proton nuclear magnetic resonance and electrospray mass spectrometry. Other metabolites were characterized according to their chromatographic behavior and mass spectral data. The major metabolic pathways of verapamil transformation by the fungus were N dealkylation, O demethylation, and sulfate conjugation. The phase I metabolites of verapamil (introduction of a functional group) by C. blakesleeana paralleled those in mammals; therefore, C. blakesleeana could be a useful tool for generating the mammalian phase I metabolites of verapamil.

  • Microbial transformation of naproxen by Cunninghamella species.
    Acta Pharmacologica Sinica, 2003
    Co-Authors: Da-fang Zhong, Hai-hua Huang
    Abstract:

    AIM: The metabolites of naproxen produced by Cunninghamella species were isolated and identified, and further to compare the similarities between microbial transformation and mammalian metabolism. METHODS: Naproxen was transformed by three strains of Cunninghammella species (Cunninghamella blakeslesna AS 3.153, Cunninghamella echinulata AS 3.2004, and Cunninghamella elegans AS 3.156). The metabolites of naproxen were separated and assayed by liquid chromatography-mass spectrometry method. Semi-preparative HPLC was used to isolate the major metabolite, and the structure was identified by nuclear magnetic resonance (NMR) and mass spectrometry. RESULTS: Naproxen was transformed into 2 metabolites, desmethylnaproxen and desmethylnaproxen-6-O-sulfate, both were the known mammalian metabolites. The conjugated metabolite was newly detected in microbial transformation samples. CONCLUSION: The microbial transformation of naproxen has some similarities with the metabolism of naproxen in mammals. The fungi belonging to Cunninghamella species could be used as complementary in vitro models for drug metabolism to predict and produce the metabolites of drugs in mammals.

Carl E Cerniglia - One of the best experts on this subject based on the ideXlab platform.

  • Biotransformation of mirtazapine by Cunninghamella elegans
    Drug metabolism and disposition: the biological fate of chemicals, 2002
    Co-Authors: J. D. Moody, James P. Freeman, Carl E Cerniglia
    Abstract:

    The fungus Cunninghamella elegans was used as a microbial model of mammalian metabolism to biotransform the tetracyclic antidepressant drug mirtazapine, which is manufactured as a racemic mixture of R(-)- and S(+)-enantiomers. In 168 h, C. elegans transformed 91% of the drug into the following seven metabolites: 8-hydroxymirtazapine, N-desmethyl-8-hydroxymirtazapine, N-desmethylmirtazapine, 13-hydroxymirtazapine, mirtazapine N-oxide, 12-hydroxymirtazapine, and N-desmethyl-13-hydroxymirtazapine. Circular dichroism spectral analysis of unused mirtazapine indicated that it was slightly enriched with the R(-)-enantiomer. When the fungus was treated with the optically pure forms of the drug, the S(+)-enantiomer produced all seven metabolites whereas the R(-)-enantiomer produced only 8-hydroxymirtazapine, N-desmethyl-8-hydroxymirtazapine, N-desmethylmirtazapine, and mirtazapine N-oxide. C. elegans produced five mammalian and two novel metabolites and is therefore a suitable microbial model for mirtazapine metabolism.

  • biotransformation of malachite green by the fungus Cunninghamella elegans
    Applied and Environmental Microbiology, 2001
    Co-Authors: Changjun Cha, Daniel R Doerge, Carl E Cerniglia
    Abstract:

    The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized the triphenylmethane dye malachite green with a first-order rate constant of 0.029 μmol h−1 (mg of cells)−1. Malachite green was enzymatically reduced to leucomalachite green and also converted to N-demethylated and N-oxidized metabolites, including primary and secondary arylamines. Inhibition studies suggested that the cytochrome P450 system mediated both the reduction and the N-demethylation reactions.

  • Biotransformation of Vinclozolin by the Fungus Cunninghamella elegans
    Journal of Agricultural and Food Chemistry, 2000
    Co-Authors: Jairaj V Pothuluri, James P. Freeman, Thomas M Heinze, Richard D. Beger, Carl E Cerniglia
    Abstract:

    This study investigated the biotransformation of the dicarboximide fungicide vinclozolin [3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione] by the fungus Cunninghamella elegans. Experiments with phenyl-[U-ring-14C]vinclozolin showed that after 96 h incubation, 93% had been transformed to four major metabolites. Metabolites were separated by HPLC and characterized by mass and NMR spectroscopy. Biotransformation occurred predominantly on the oxazolidine-2,4-dione portion of vinclozolin. The metabolites were identified as the 3R- and 3S- isomers of 3‘,5‘-dichloro-2,3,4-trihydroxy-2-methylbutyranilide, N-(2-hydroxy-2-methyl-1-oxobuten-3-yl)-3,5-dichlorophenyl-1-carbamic acid, and 3‘,5‘-dichloro-2-hydroxy-2-methylbut-3-enanilide. The enanilide compound has been reported previously as a plant and mammalian metabolite and is implicated to contain antiandrogenic activity. The 3R- and 3S- isomers of 3‘,5‘-dichloro-2,3,4-trihydroxy-2-methylbutyranilide are novel metabolites. Keywords: Vinclozolin; ...

  • fungal metabolism of acenaphthene by Cunninghamella elegans
    Applied and Environmental Microbiology, 1992
    Co-Authors: Jairaj V Pothuluri, Frederick E Evans, J.p. Freeman, Carl E Cerniglia
    Abstract:

    The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized within 72 h of incubation approximately 64% of the [1,8-14C]acenaphthene added. The radioactive metabolites were extracted with ethyl acetate and separated by thin-layer chromatography and reversed-phase high-performance liquid chromatography. Seven metabolites were identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques as 6-hydroxyacenaphthenone (24.8%), 1,2-acenaphthenedione (19.9%), trans-1,2-dihydroxyacenaphthene (10.3%), 1,5-dihydroxyacenaphthene (2.7%), 1-acenaphthenol (2.4%), 1-acenaphthenone (2.1%), and cis-1,2-dihydroxyacenaphthene (1.8%). Parallel experiments with rat liver microsomes indicated that the major metabolite formed from acenaphthene by rat liver microsomes was 1-acenaphthenone. The fungal metabolism of acenaphthene was similar to bacterial and mammalian metabolism, since the primary site of enzymatic attack was on the two carbons of the five-member ring.

Hai-hua Huang - One of the best experts on this subject based on the ideXlab platform.

  • Biotransformation of metoprolol by the fungus Cunninghamella blakesleeana
    Acta pharmacologica Sinica, 2007
    Co-Authors: Hai-hua Huang, Xiaoyan Chen, Yuming Sun, Li Hong Lin, Da-fang Zhong
    Abstract:

    Aim: To investigate the biotransformation of metoprolol, a β 1 -cardioselective adrenoceptor antagonist, by filamentous fungus, and to compare the parallels between microbial transformation and mammalian metabolism. Methods: Five strains of Cunninghamella ( C elegans AS 3.156, C elegans AS 3.2028, C echinulata AS 3.2004, C blakesleeana AS 3.153 and AS 3.910) were screened for the ability to transform metoprolol. The metabolites of metoprolol produced by C blakesleeana AS 3.153 were separated and assayed by liquid chromatography-tandem mass spectrometry (LC/MS n ). The major metabolites were isolated by semipreparative HPLC and the structures were identified by a combination of LC/MS n and nuclear magnetic resonance analysis. Results: Metoprolol was transformed to 7 metabolites; 2 were identified as new metabolites and 5 were known metabolites in mammals. Conclusion: The microbial transformation of metoprolol was similar to the metabolism in mammals. The fungi belonging to Cunninghamella species could be used as complementary models for predicting in vivo metabolism and producing quantities of metabolite references for drugs like metoprolol.

  • biotransformation of indomethacin by the fungus Cunninghamella blakesleeana
    Acta Pharmacologica Sinica, 2006
    Co-Authors: Peng Zhang, Da-fang Zhong, Hai-hua Huang, Li Hong Lin
    Abstract:

    Aim: To investigate the biotransformation of indomethacin, the first of the newer nonsteroidal anti-inflammatory drugs, by filamentous fungus and to compare the similarities between microbial transformation and mammalian metabolism of indomethacin. Methods: Five strains of Cunninghamella (C elegans AS 3.156, C elegans AS 3.2028, C blakesleeana AS 3.153, C blakesleeana AS 3.910 and C echinulata AS 3.2004) were screened for their ability to catalyze the biotransformation of indomethacin. Indomethacin was partially metabolized by five strains of Cunninghamella , and C blakesleeana AS 3.910 was selected for further investigation. Three metabolites produced by C blakesleeana AS 3.910 were isolated using semi-preparative HPLC, and their structures were identified by a combination analysis of LC/MS n and NMR spectra. These three metabolites were separated and quantitatively assayed by liquid chromatography-ion trap mass spectrometry. Results: After 120 h of incubation with C blakesleeana AS 3.910, approximately 87.4% of indomethacin was metabolized to three metabolites: O -desmethylindomethacin (DMI, M1, 67.2%), N -deschlorobenzoylindomethacin (DBI, M2, 13.3%) and O -desmethyl- N -deschlorobenzoylindomethacin (DMBI, M3, 6.9%). Three phase I metabolites of indomethacin produced by C blakesleeana AS 3.910 were identical to those obtained in humans. Conclusion: C blakesleeana could be a useful tool for generating the mammalian phase I metabolites of indomethacin.

  • Biotransformation of pantoprazole by the fungus Cunninghamella blakesleeana
    Xenobiotica, 2005
    Co-Authors: Hai-hua Huang, Da-fang Zhong
    Abstract:

    To investigate the biotransformation of pantoprazole, a proton-pump inhibitor, by filamentous fungus and further to compare the similarities between microbial transformation and mammalian metabolism of pantoprazole, four strains of Cunninghamella (C. blakesleeana AS 3.153, C. echinulata AS 3.2004, C. elegans AS 3.156, and AS 3.2028) were screened for the ability to catalyze the biotransformation of pantoprazole. Pantoprazole was partially metabolized by four strains of Cunninghamella, and C. blakesleeana AS 3.153 was selected for further investigation. Three metabolites produced by C. blakesleeana AS 3.153 were isolated using semi-preparative HPLC, and their structures were identified by a combination analysis of LC/MSn and NMR spectra. Two further metabolites were confirmed with the aid of synthetic reference compounds. The structure of a glucoside was tentatively assigned by its chromatographic behavior and mass spectroscopic data. These six metabolites were separated and quantitatively assayed by liqui...

  • transformation of verapamil by Cunninghamella blakesleeana
    Applied and Environmental Microbiology, 2004
    Co-Authors: Lu Sun, Hai-hua Huang, Lei Liu, Da-fang Zhong
    Abstract:

    A filamentous fungus, Cunninghamella blakesleeana AS 3.153, was used as a microbial model of mammalian metabolism to transform verapamil, a calcium channel antagonist. The metabolites of verapamil were separated and assayed by the liquid chromatography-ion trap mass spectrometry method. After 96 h of incubation, nearly 93% of the original drug was metabolized to 23 metabolites. Five major metabolites were isolated by semipreparative high-performance liquid chromatography and were identified by proton nuclear magnetic resonance and electrospray mass spectrometry. Other metabolites were characterized according to their chromatographic behavior and mass spectral data. The major metabolic pathways of verapamil transformation by the fungus were N dealkylation, O demethylation, and sulfate conjugation. The phase I metabolites of verapamil (introduction of a functional group) by C. blakesleeana paralleled those in mammals; therefore, C. blakesleeana could be a useful tool for generating the mammalian phase I metabolites of verapamil.

  • Microbial transformation of naproxen by Cunninghamella species.
    Acta Pharmacologica Sinica, 2003
    Co-Authors: Da-fang Zhong, Hai-hua Huang
    Abstract:

    AIM: The metabolites of naproxen produced by Cunninghamella species were isolated and identified, and further to compare the similarities between microbial transformation and mammalian metabolism. METHODS: Naproxen was transformed by three strains of Cunninghammella species (Cunninghamella blakeslesna AS 3.153, Cunninghamella echinulata AS 3.2004, and Cunninghamella elegans AS 3.156). The metabolites of naproxen were separated and assayed by liquid chromatography-mass spectrometry method. Semi-preparative HPLC was used to isolate the major metabolite, and the structure was identified by nuclear magnetic resonance (NMR) and mass spectrometry. RESULTS: Naproxen was transformed into 2 metabolites, desmethylnaproxen and desmethylnaproxen-6-O-sulfate, both were the known mammalian metabolites. The conjugated metabolite was newly detected in microbial transformation samples. CONCLUSION: The microbial transformation of naproxen has some similarities with the metabolism of naproxen in mammals. The fungi belonging to Cunninghamella species could be used as complementary in vitro models for drug metabolism to predict and produce the metabolites of drugs in mammals.

Jixun Zhan - One of the best experts on this subject based on the ideXlab platform.

  • metabolism of quercetin by Cunninghamella elegans atcc 9245
    Journal of Bioscience and Bioengineering, 2011
    Co-Authors: Jonathan Valiente, Jia Zeng, Jixun Zhan
    Abstract:

    Incubation of quercetin with Cunninghamella elegans ATCC 9245 yielded three metabolites, including quercetin 3-O-β-D-glucopyranoside, kaempferol 3-O-β-D-glucopyranoside and isorhamnetin 3-O-β-D-glucopyranoside. Glucosylation, O-methylation and dehydroxylation were involved in the process, among which dehydroxylation has never been found in Cunninghamella. Quercetin was completely metabolized in 72 h.

  • biotransformation of triptolide by Cunninghamella blakesleana
    Tetrahedron, 2003
    Co-Authors: Jixun Zhan, Hongzhu Guo, Lili Ning, Lei Zhong, Dean Guo
    Abstract:

    Abstract Biotransformation of triptolide 1 by Cunninghamella blakesleana (AS 3.970) was carried out. Seven biotransformation products were obtained and four of them were characterized as new compounds. On the basis of their NMR and mass spectral data, their structures were characterized as 5α-hydroxytriptolide 2 , 1β-hydroxytriptolide 3 , triptodiolide 4 , 16-hydroxytriptolide 5 , triptolidenol 6 , 19α-hydroxytriptolide 7 and 19β-hydroxytriptolide 8 . All the new transformed products ( 2 , 3 , 7 and 8 ) were found to exhibit potent in vitro cytotoxicity against some human tumor cell lines.

  • microbial transformations of artemisinin by Cunninghamella echinulata and aspergillus niger
    Tetrahedron Letters, 2002
    Co-Authors: Jixun Zhan, Hongzhu Guo, Jungui Dai, Yuanxing Zhang, Dean Guo
    Abstract:

    Microbial transformations of artemisinin 1 by Cunninghamella echinulata (AS 3.3400) and Aspergillus niger (AS 3.795) were carried out. Two products, 10β-hydroxyartemisinin 2 and 3α-hydroxydeoxyartemisinin 3, were obtained. Their structures were identified on the basis of chemical and spectroscopic data. 10β-Hydroxyartemisinin is a new compound.