Biotransformation of pseudolaric acid B by Chaetomium globosum

Zhang, Xing; Ye, Min; Gong, Yujing; Feng, Lin-min; Tao, Sijia; Yin, Jun; Guo, Dan

doi:10.1016/j.procbio.2011.07.019

Cited by 7 publications

(5 citation statements)

References 11 publications

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“…Reduction of carboxyl groups at non-active sites are important enzymatic reactions catalyzed by microorganisms, for example. Literature has shown that phase II enzymes such as sulfotransferases, UDP-glucuronosyltransferases, glycine N -acyltransferases and methyl-transferases can react with different diterpenes, increasing their molecular weight and polarity [ 44 , 45 , 46 ].…”

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

“…Pseudolaric acid B (compound 8 in Figure 10 ) is a diterpene that displays anticancer, antifertility and potent antifungal activities. The bioconversion of 8 by Chaetomium globosum afforded the three novel compounds pseudolaric acid I ( 8.3 ), pseudolaric acid B 18-oyl-alanine ( 8.5 ), and pseudolaric acid B 18-oyl-serine ( 8.2 ) [ 46 ]. Two known compounds, pseudolaric acid F ( 8.4 ) and pseudolaric acid B 18-oyl-glycine ( 8.1 )m were also isolated from the biotransformation extracts ( Figure 10 ).…”

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

“…The detoxification process, common to human metabolism of xenobiotics, can also occur in microbial cells. For instance, when incubated with the potent antifungal pseudolaric acid B, Chaetomium globosum bioconverted the diterpenoid into five inactive metabolites [ 46 ]. The fungi stopped growing in the presence of pseudolaric acid B, but after two days of incubation, the mycelia continued growing.…”

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

“… Derivatives ( 8.1 – 8.5 ) of pseudolaric acid ( 8 ) obtained by Chaetomium globosum biotransformation [ 46 ]. …”

Section: Figurementioning

confidence: 99%

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An Overview of Biotransformation and Toxicity of Diterpenes

2018

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Diterpenes have been identified as active compounds in several medicinal plants showing remarkable biological activities, and some isolated diterpenes are produced at commercial scale to be used as medicines, food additives, in the synthesis of fragrances, or in agriculture. There is great interest in developing methods to obtain derivatives of these compounds, and biotransformation processes are interesting tools for the structural modification of natural products with complex chemical structures. Biotransformation processes also have a crucial role in drug development and/or optimization. The understanding of the metabolic pathways for both phase I and II biotransformation of new drug candidates is mandatory for toxicity and efficacy evaluation and part of preclinical studies. This review presents an overview of biotransformation processes of diterpenes carried out by microorganisms, plant cell cultures, animal and human liver microsomes, and rats, chickens, and swine in vivo and highlights the main enzymatic reactions involved in these processes and the role of diterpenes that may be effectively exploited by other fields.

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Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

“… Derivatives ( 8.1 – 8.5 ) of pseudolaric acid ( 8 ) obtained by Chaetomium globosum biotransformation [ 46 ]. …”

Section: Figurementioning

confidence: 99%

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An Overview of Biotransformation and Toxicity of Diterpenes

2018

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“…A literatura demonstra que diversos carbonos do núcleo terpenoide são suscetíveis a uma série de modificações químicas por biotransformação, incluindo hidroxilações, redução, hidrólise, epoxidação, redução de grupos carboxílicos, metilação, conjugação com ácido glucurônico, sulfato e aminoácidos (SULTANA & SAIFY, 2013;GARCÍA-GRANADOS et al, 2007;BHATTI & KERA, 2014;WANG et al, 2010;ZHANG et al, 2011). O esclareol é um diterpeno labdano extensivamente estudado em processos de biotransformação.…”

Section: Friedrich Nietzscheunclassified

Biotransformações dos ácidos ent-poliáltico e ent-diidroagático por culturas microbianas e microssomas hepáticos

Sousa¹

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Synthetic Studies toward Pseudolaric Acids: Radical Cyclization to Form Bridged Scaffold

Niu,

Lin,

Cui

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryPseudolaric acids are a family of diterpenoid natural products that exhibit a broad spectrum of biological activities. The main structural feature of their framework is a trans‐fused perhydroazulene bearing a bridged lactone positioned at the junction of the rings. Herein, we have developed a radical cyclization strategy that allows flexible tuning of the cyclization process through diverse silicon substitutions on the substrates. This strategy can assist in constructing a series of skeletons with structural resemblance to pseudolaric acids and expedites the construction of the bridged lactone. Finally, it facilitates the synthesis of the entire skeletal structure of the pseudolaric acid family of natural products, excluding the B‐ring functionalization.

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Biotransformation of pseudolaric acid B by Chaetomium globosum

Cited by 7 publications

References 11 publications

An Overview of Biotransformation and Toxicity of Diterpenes

An Overview of Biotransformation and Toxicity of Diterpenes

Biotransformações dos ácidos ent-poliáltico e ent-diidroagático por culturas microbianas e microssomas hepáticos

Synthetic Studies toward Pseudolaric Acids: Radical Cyclization to Form Bridged Scaffold

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