Biotransformation of a mulinane diterpenoid by Aspergillus alliaceus and Mucor circinelloides

Herrera-Canché, Stephanie G.; Sánchez-González, Mónica Noel; Loyola, Luis A.; Bórquez, Jorge; García‐Sosa, Karlina; Peña‐Rodríguez, Luis M.

doi:10.1080/10242422.2019.1596083

Cited by 6 publications

(2 citation statements)

References 35 publications

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“…To date, only one semisynthetic azorellane derivative, 7 β -deacetylazorellanol ( 16 ), has been reported; this can be explained by the fact that the cyclopropane ring in the azorellane skeleton can be easily open under weak acidic conditions, to produce semisynthetic derivatives having a mulinane skeleton [ 54 ]. However, the limited number of functionalized positions, and the type of functional groups, found in the chemical structures of natural azorellane and mulinane diterpenoids limit the number and type of semisynthetic derivatives that can be prepared through chemical modification [ 55 ]; because of this, in recent years, biotransformation using filamentous fungi such as Mucor plumbeus and M. circinelloides has been explored as a new strategy to obtain novel mulinane and azorellane derivatives [ 51 , 55 , 56 ] ( Table 4 , Figure 6 ).…”

Section: Synthetic Semisynthetic and Biotransformed Mulinane Andmentioning

confidence: 99%

Mulinane- and Azorellane-Type Diterpenoids: A Systematic Review of Their Biosynthesis, Chemistry, and Pharmacology

et al. 2020

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Mulinane- and azorellane-type diterpenoids have unique tricyclic fused five-, six-, and seven-membered systems and a wide range of biological properties, including antimicrobial, antiprotozoal, spermicidal, gastroprotective, and anti-inflammatory, among others. These secondary metabolites are exclusive constituents of medicinal plants belonging to the Azorella, Laretia, and Mulinum genera. In the last 30 years, more than 95 mulinanes and azorellanes have been reported, 49 of them being natural products, 4 synthetics, and the rest semisynthetic and biotransformed derivatives. This systematic review highlights the biosynthetic origin, the chemistry, and the pharmacological activities of this remarkably interesting group of diterpenoids.

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Section: Synthetic Semisynthetic and Biotransformed Mulinane Andmentioning

confidence: 99%

Mulinane- and Azorellane-Type Diterpenoids: A Systematic Review of Their Biosynthesis, Chemistry, and Pharmacology

et al. 2020

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“…These compounds have an intrinsic ability to undergo diverse chemical reactions, leading to the generation of novel bioactive compounds. 11 The dynamic nature of natural products, coupled with their ability to undergo various chemical transformations, underscores their versatility as a valuable resource in the continuous pursuit of innovative drug development. Functional groups present in natural products often undergo chemical transformations such as oxidation, reduction, esterification, and alkylation, resulting in derivatives with altered biological activities.…”

Section: Introductionmentioning

confidence: 99%

Acid Induced Phytoconstituents of Calotropis procera Extract Combined with Ampicillin in Combating Clinical Resistant Isolates of Staphylococcus aureus and Salmonella spp.

Gideon,

Ladan,

Yakubu

2024

Fine Chemical Engineering

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Natural products, with their inherent diversity, offer unique pharmacophores, chemotypes, and scaffolds that can be harnessed to create effective drugs targeting various infections and diseases. This study introduces a straightforward, rudimentary, and environmentally sustainable method to enhance the antimicrobial activity of two less potent antimicrobial agents, fostering synergism against drug-resistant clinical bacteria. The aqueous extract of fresh leaves and flowers of Calotropis procera was subjected to a reaction with a 1 mg/mL ampicillin solution, resulting in synergy and heightened susceptibility against resistant strains of Staphylococcus aureus and Salmonella spp., augmenting their zones of inhibition from 0 mm to 16.8 mm and from 5.3 mm to 21.4 mm, respectively. Gas chromatography-mass spectrometry (GC-MS) analysis identified 53 phytochemicals in C. procera extract, revealing oleic acid (13.04%), 1,1,1,3,5,5,7,7,7-nonamethyl-3-(trimethylsiloxy) tetrasiloxane (9.50%), 9-heptadecanone (3.75%), cystamine (3.35%), and tetrahydro-4H-pyran-4-ol (3.15%) as the top five most abundant phytochemicals. Notably, 18 out of the 53 phytochemicals were associated with known reported biological activities. The analysis revealed the discovery of compounds such as farnesol, cystamine, cystine, metaraminol, dl-phenylephrine, and two distinct substituted amphetamine compounds. Three phytochemicals demonstrated anticancer properties, namely farnesol, 4-amino-1-pentanol, and an imidazole derivative resembling the drug Ribavir. These compounds may serve as valuable starting materials, intermediates, or derivatives in pharmaceutical production.

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Separation and purification of plant terpenoids from biotransformation

Chen

Pang

Luo

et al. 2021

Engineering in Life Sciences

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The production of plant terpenoids through biotransformation has undoubtedly become one of the research hotspots, and the continuous upgrading of the corresponding downstream technology is also particularly important. Downstream technology is the indispensable technical channel for the industrialization of plant terpenoids. How to efficiently separate high‐purity products from complex microbial fermentation broths or enzyme‐catalyzed reactions to achieve high separation rates, high returns and environmental friendliness has become the focus of research in recent years. This review mainly introduces the common separation methods of plant terpenoids based on biotransformation from the perspectives of engineering strain construction, unit separation technology, product properties and added value. Then, further attention was paid to the application prospects of intelligent cell factories and control in the separation of plant terpenoids. Finally, some current challenges and prospects are proposed, which provide possible directions and guidance for the separation and purification of terpenoids and even industrialization.

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Biotransformation of a mulinane diterpenoid by Aspergillus alliaceus and Mucor circinelloides

Cited by 6 publications

References 35 publications

Mulinane- and Azorellane-Type Diterpenoids: A Systematic Review of Their Biosynthesis, Chemistry, and Pharmacology

Mulinane- and Azorellane-Type Diterpenoids: A Systematic Review of Their Biosynthesis, Chemistry, and Pharmacology

Acid Induced Phytoconstituents of <i>Calotropis procera</i> Extract Combined with Ampicillin in Combating Clinical Resistant Isolates of <i>Staphylococcus aureus</i> and <i>Salmonella</i> spp.

Separation and purification of plant terpenoids from biotransformation

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