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      Two New Terpenoids from Talaromyces purpurogenus

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          Abstract

          A new sesquiterpenoid 9,10-diolhinokiic acid ( 1) and a new diterpenoid roussoellol C ( 2), together with 4 known compounds, were isolated from the extracts of laboratory cultures of marine-derived fungus Talaromyces purpurogenus. 9,10-diolhinokiic acid is the first thujopsene-type sesquiterpenoid containing a 9,10-diol moiety, and roussoellol C possesses a novel tetracyclic fusicoccane framework with an unexpected hydroxyl at C-4. These new structures were confirmed by spectroscopic data, chemical method, NMR data calculations and electronic circular dichroism (ECD) calculations. The selected compounds were evaluated for cytotoxicities against five human cancer cell lines, including SW480, HL-60, A549, MCF-7, and SMMC-7721 and the IC 50 values of compound 2 against MCF-7 and 3 against HL-60 cells were 6.5 and 7.9 μM, respectively.

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          Most cited references30

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          Generating conformer ensembles using a multiobjective genetic algorithm.

          The task of generating a nonredundant set of low-energy conformations for small molecules is of fundamental importance for many molecular modeling and drug-design methodologies. Several approaches to conformer generation have been published. Exhaustive searches suffer from the exponential growth of the search space with increasing degrees of conformational freedom (number of rotatable bonds). Stochastic algorithms do not suffer as much from the exponential increase of search space and provide a good coverage of the energy minima. Here, the use of a multiobjective genetic algorithm in the generation of conformer ensembles is investigated. Distance geometry is used to generate an initial conformer, which is then subject to geometric modifications encoded by the individuals of the genetic algorithm. The geometric modifications apply to torsion angles about rotatable bonds, stereochemistry of double bonds and tetrahedral chiral centers, and ring conformations. The geometric diversity of the evolving conformer ensemble is preserved by a fitness-sharing mechanism based on the root-mean-square distance of the atomic coordinates. Molecular symmetry is taken into account in the distance calculation. The geometric modifications introduce strain into the structures. The strain is relaxed using an MMFF94-like force field in a postprocessing step that also removes conformational duplicates and structures whose strain energy remains above a predefined window from the minimum energy value found in the set. The implementation, called Balloon, is available free of charge on the Internet ( http://www.abo.fi/~mivainio/balloon/).
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            Fungal metabolites with anticancer activity.

            Covering: 1964 to 2013. Natural products from bacteria and plants have played a leading role in cancer drug discovery resulting in a large number of clinically useful agents. In contrast, the investigations of fungal metabolites and their derivatives have not led to a clinical cancer drug in spite of significant research efforts revealing a large number of fungi-derived natural products with promising anticancer activity. Many of these natural products have displayed notable in vitro growth-inhibitory properties in human cancer cell lines and select compounds have been demonstrated to provide therapeutic benefits in mouse models of human cancer. Many of these compounds are expected to enter human clinical trials in the near future. The present review discusses the reported sources, structures and biochemical studies aimed at the elucidation of the anticancer potential of these promising fungal metabolites.
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              Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi.

              Three new diketopiperazine alkaloids, 6-methoxyspirotryprostatin B (1), 18-oxotryprostatin A (2), and 14-hydroxyterezine D (3), with an oxaspiro[4.4]lactam moiety, 14-norpseurotin A (4), and the 29-nordammarane triterpenoid 6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (5), as well as 12 known compounds (6- 17), were isolated from the ethyl acetate extract of a marine-derived fungal strain, Aspergillus sydowi PFW1-13. The structures of compounds 1- 5 were elucidated by comprehensive spectroscopic analysis. Compounds 1- 3 exhibit weak cytotoxicity against A-549 cells, with IC 50 values of 8.29, 1.28, and 7.31 microM, respectively. Compound 1 also shows slight cytotoxicity against HL-60 cells, with an IC 50 value of 9.71 microM. Compounds 4 and 5 display significant antimicrobial activities against Escherichia coli, Bacillus subtilis, and Micrococcus lysoleikticus with MICs of 3.74, 14.97, and 7.49 microM and 10.65, 5.33, and 10.65 microM, respectively.
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                Author and article information

                Journal
                Mar Drugs
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                02 May 2018
                May 2018
                : 16
                : 5
                : 150
                Affiliations
                Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China; wangwj0122@ 123456163.com (W.W.); marina.wanx@ 123456gmail.com (X.W.); junjun.liu@ 123456hust.edu.cn (J.L.); jpwang1001@ 123456163.com (J.W.); zhuhucheng@ 123456hust.edu.cn (H.Z.)
                Author notes
                [* ]Correspondence: chenchunmei@ 123456hust.edu.cn (C.C.); zhangyh@ 123456mails.tjmu.edu.cn (Y.Z.); Tel.: +86-27-8369-2892 (C.C.); +86-27-8369-2892 (Y.Z.)
                Author information
                https://orcid.org/0000-0001-9953-8633
                https://orcid.org/0000-0002-7222-2142
                Article
                marinedrugs-16-00150
                10.3390/md16050150
                5983281
                29724060
                8e7e4764-777f-4552-a6ac-581f5135cb86
                © 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
                : 30 March 2018
                : 27 April 2018
                Categories
                Communication

                Pharmacology & Pharmaceutical medicine
                sesquiterpenoid,diterpenoid,talaromyces purpurogenus,nmr data calculations,ecd calculations,cytotoxicities

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