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      Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor

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          Abstract

          Asperversins A ( 1) and B ( 2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues ( 37) and a known compound asperdemin ( 8), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures and absolute configurations were confirmed by extensive spectroscopic analyses, single-crystal X-ray diffraction studies, and electronic circular dichroism (ECD) calculation. All new compounds were tested for their acetylcholinesterase enzyme (AChE) inhibitory activities and cytotoxic activities, of which compound 7 displayed moderate inhibitory activity against the AChE with an IC 50 value of 13.6 μM.

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          Most cited references24

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          Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms.

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            Biosynthesis of fungal meroterpenoids.

            Covering: up to September 2015. Meroterpenoids are hybrid natural products that partially originate from the terpenoid pathway. The meroterpenoids derived from fungi display quite diverse structures, with a wide range of biological properties. This review summarizes the molecular bases for their biosyntheses, which were recently elucidated with modern techniques, and also discusses the plausible biosynthetic pathways of other related natural products lacking genetic information. (Complementary to the coverage of literature by Geris and Simpson in Nat. Prod. Rep., 2009, 26, 1063-1094.).
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              Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases.

              Meroterpenoids are hybrid natural products of both terpenoid and polyketide origin. We identified a biosynthetic gene cluster that is responsible for the production of the meroterpenoid pyripyropene in the fungus Aspergillus fumigatus through reconstituted biosynthesis of up to five steps in a heterologous fungal expression system. The cluster revealed a previously unknown terpene cyclase with an unusual sequence and protein primary structure. The wide occurrence of this sequence in other meroterpenoid and indole-diterpene biosynthetic gene clusters indicates the involvement of these enzymes in the biosynthesis of various terpenoid-bearing metabolites produced by fungi and bacteria. In addition, a novel polyketide synthase that incorporated nicotinyl-CoA as the starter unit and a prenyltransferase, similar to that in ubiquinone biosynthesis, was found to be involved in the pyripyropene biosynthesis. The successful production of a pyripyropene analogue illustrates the catalytic versatility of these enzymes for the production of novel analogues with useful biological activities.
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                Author and article information

                Journal
                Mar Drugs
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                23 May 2018
                June 2018
                : 16
                : 6
                : 177
                Affiliations
                Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China; lihuaqiang2009@ 123456126.com (H.L.); weiguang_s@ 123456hust.edu.cn (W.S.); DengMengyi222@ 123456163.com (M.D.); kingqcx@ 123456sina.cn (C.Q.); chenchunmei@ 123456hust.edu.cn (C.C.); zhuhucheng@ 123456hust.edu.cn (H.Z.); luozengwei@ 123456hust.edu.cn (Z.L.)
                Author notes
                [* ]Correspondence: jpwang1001@ 123456163.com (J.W.); yongboxue@ 123456hust.edu.cn (Y.X.); zhangyh@ 123456mails.tjmu.edu.cn (Y.Z.); Tel.: +86-027-8369-2892 (Y.Z.)
                Author information
                https://orcid.org/0000-0001-9133-6439
                https://orcid.org/0000-0002-7222-2142
                Article
                marinedrugs-16-00177
                10.3390/md16060177
                6025407
                29882867
                b11da282-ffd7-4809-93cf-803dec6134ed
                © 2018 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 17 April 2018
                : 14 May 2018
                Categories
                Communication

                Pharmacology & Pharmaceutical medicine
                aspergillus versicolor,meroterpenoids,asperversins,acetylcholinesterase enzyme

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