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Special Issue "Biosynthesis and Biotransformation"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 December 2013)

Special Issue Editor

Guest Editor
Dr. Ioulia Smonou (Website)

Department of Chemistry, University of Crete, Campus Voutes-Heraklion, 71003 Crete, Greece
Interests: biocatalysis-biotransformations in organic synthesis; asymmetric synthesis of bioactive compounds using biocatalytic methods; applied biocatalysis; mechanisms of organic reactions

Special Issue Information

Dear Colleagues,

The contribution of Biosynthesis and Biotransformation is of increasing importance as potential alternative methods toward the synthesis of useful metabolites and their commercial production. Plant secondary metabolites, the natural products, are very useful in food and pharmaceutical industry,but their production by total synthesis is not economical. Plant cell culture or hairy root culture technology can be used as alternative methodology for the synthesis of useful chemical compounds or for the transformation of natural products to a variety of compounds of high economical importance.
Moreover, biotransformations, where secondary metabolites as well as xenobiotic compounds can be used as substrates, has emerged as one of the major targets of biotechnological application, offering great innovative potential in the otherwise difficult or impossible stereospecific synthesis of important organic molecules. Biotransformation reactions catalyzed by plant cell cultures include oxidoreductions, hydroxylations, acylations, etc. This innovative methodology is of great importance for industrial application.
This Special Issue on Biosynthesis and Biotransformation will offer an attractive forum to present the potential of this technology. I strongly encourage authors to submit papers for this Special Issue, within the scope of Molecules. I hope that the topics covered will reflect the potential and the excitement of Biosynthesis and Biotransformation in the scientific community.

Ioulia Smonou
Guest Editor

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs).


Keywords

  • biosynthetic enzymes
  • biosynthesis and Bacteria
  • mechanistic studies
  • biosynthesis of natural products
  • biocatalysis
  • enzymatic reactions
  • biotransformations

Published Papers (3 papers)

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Research

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Open AccessArticle Artichoke, Cynarin and Cyanidin Downregulate the Expression of Inducible Nitric Oxide Synthase in Human Coronary Smooth Muscle Cells
Molecules 2014, 19(3), 3654-3668; doi:10.3390/molecules19033654
Received: 13 January 2014 / Revised: 17 March 2014 / Accepted: 18 March 2014 / Published: 24 March 2014
Cited by 1 | PDF Full-text (439 KB) | HTML Full-text | XML Full-text
Abstract
Artichoke (Cynara scolymus L.) is one of the world’s oldest medicinal plants with multiple health benefits. We have previously shown that artichoke leaf extracts and artichoke flavonoids upregulate the gene expression of endothelial-type nitric oxide synthase (eNOS) in human endothelial cells. [...] Read more.
Artichoke (Cynara scolymus L.) is one of the world’s oldest medicinal plants with multiple health benefits. We have previously shown that artichoke leaf extracts and artichoke flavonoids upregulate the gene expression of endothelial-type nitric oxide synthase (eNOS) in human endothelial cells. Whereas NO produced by the eNOS is a vasoprotective molecule, NO derived from the inducible iNOS plays a pro-inflammatory role in the vasculature. The present study was aimed to investigate the effects of artichoke on iNOS expression in human coronary artery smooth muscle cells (HCASMC). Incubation of HCASMC with a cytokine mixture led to an induction of iNOS mRNA expression. This iNOS induction was concentration- and time-dependently inhibited by an artichoke leaf extract (1–100 µg/mL, 6 h or 24 h). Consistently, the artichoke leaf extract also reduced cytokine-induced iNOS promoter activation and iNOS protein expression. In addition, treatment of HCASMC with four well-known artichoke compounds (cynarin > cyanidin > luteolin ≈ cynaroside) led to a downregulation iNOS mRNA and protein expression, with cynarin being the most potent one. In conclusion, artichoke contains both eNOS-upregulating and iNOS-downregulating compounds. Such compounds may contribute to the beneficial effects of artichoke and may per se have therapeutic potentials. Full article
(This article belongs to the Special Issue Biosynthesis and Biotransformation)
Open AccessArticle Baeyer-Villiger Oxidation of Some C19 Steroids by Penicillium lanosocoeruleum
Molecules 2013, 18(11), 13812-13822; doi:10.3390/molecules181113812
Received: 8 September 2013 / Revised: 28 October 2013 / Accepted: 30 October 2013 / Published: 7 November 2013
Cited by 5 | PDF Full-text (245 KB) | HTML Full-text | XML Full-text
Abstract
The biotransformation of androsterone (1), epiandrosterone (2), androstanedione (3) and DHEA (dehydroepiandrosterone) (4) by Penicillium lanosocoeruleum—a fungal species not used in biotransformations so far—were described. All the substrates were converted in high yield [...] Read more.
The biotransformation of androsterone (1), epiandrosterone (2), androstanedione (3) and DHEA (dehydroepiandrosterone) (4) by Penicillium lanosocoeruleum—a fungal species not used in biotransformations so far—were described. All the substrates were converted in high yield (70%–99%) into D ring δ-lactones. The oxidation of 1 produced 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (5). The oxidation of 2 led to 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (6). The biotransformation of 3 resulted in the formation of 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (5) and 17a-oxa-D-homo-5α-androstan-3,17-dione (7). An analysis of the transformation progress of the studied substrates as a function of time indicates that the Baeyer-Villiger monooxygenase of this fungus does not accept the 3β-hydroxy-5-ene functionality of steroids. In this microorganism steroidal 3β-hydroxy-dehydrogenase (3β-HSD) was active, and as a result DHEA (4) was transformed exclusively to testololactone (8). Apart from the observed oxidative transformations, a reductive pathway was revealed with the C-3 ketone being reduced to a C-3α-alcohol. It is demonstrated for the first time that the reduction of the 3-keto group of the steroid nucleus can occur in the presence of a ring-D lactone functionality. Full article
(This article belongs to the Special Issue Biosynthesis and Biotransformation)
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Review

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Open AccessReview The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
Molecules 2014, 19(2), 1856-1886; doi:10.3390/molecules19021856
Received: 24 December 2013 / Revised: 5 February 2014 / Accepted: 6 February 2014 / Published: 10 February 2014
Cited by 2 | PDF Full-text (423 KB) | HTML Full-text | XML Full-text
Abstract
The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several [...] Read more.
The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several plant species and a myriad of biological activities has been related to these compounds. Studies on structure versus activity have showed that, in most cases, in kaurane diterpenes, activity increases with the increase of functionalization. Since naturally occurring kaurane diterpenes usually have limited functional groups to be used as targets for semi-synthetic modifications, production of more polar derivatives from kaurane diterpenes have been achieved mostly through the use of fungal biotransformations. In this review, selected examples the wonderful chemical diversity produced by fungi in kaurane diterpenes is presented. This diversity includes mainly hydroxylation of nearly all carbon atoms of the kaurane molecule, many of them carried out stereoselectively, as well as ring rearrangements, among other chemical modifications. Sources of starting materials, general biotransformation protocols employed, fungi with most consistent regioselectivity towards kaurane skeleton, as well as biological activities associated with starting materials and products are also described. Full article
(This article belongs to the Special Issue Biosynthesis and Biotransformation)

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