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Crystal Structures of Fsa2 and Phm7 Catalyzing [4 + 2] Cycloaddition Reactions with Reverse Stereoselectivities in Equisetin and Phomasetin Biosynthesis.
Chi C, Wang Z, Liu T, Zhang Z, Zhou H, Li A, Jin H, Jia H, Yin F, Yang D, Ma M. Chi C, et al. ACS Omega. 2021 May 6;6(19):12913-12922. doi: 10.1021/acsomega.1c01593. eCollection 2021 May 18. ACS Omega. 2021. PMID: 34056443 Free PMC article.
Fsa2 and Phm7 are a unique pair of pericyclases catalyzing [4 + 2] cycloaddition reactions with reverse stereoselectivities in the biosynthesis of equisetin and phomasetin, both of which are potent HIV-1 integrase inhibitors. We here solve the crystal structures of Fsa2 an …
Fsa2 and Phm7 are a unique pair of pericyclases catalyzing [4 + 2] cycloaddition reactions with reverse stereoselectivities in the biosynthe …
Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.
Fujiyama K, Kato N, Re S, Kinugasa K, Watanabe K, Takita R, Nogawa T, Hino T, Osada H, Sugita Y, Takahashi S, Nagano S. Fujiyama K, et al. Angew Chem Int Ed Engl. 2021 Oct 4;60(41):22401-22410. doi: 10.1002/anie.202106186. Epub 2021 Jul 5. Angew Chem Int Ed Engl. 2021. PMID: 34121297 Free PMC article.
Here, we solved the X-ray crystal structures of a pair of decalin synthases, Fsa2 and Phm7, that catalyze intramolecular [4+2] cycloadditions to form enantiomeric decalin scaffolds during biosynthesis of the HIV-1 integrase inhibitor equisetin and its stereochemical opposite, …
Here, we solved the X-ray crystal structures of a pair of decalin synthases, Fsa2 and Phm7, that catalyze intramolecular [4+2] cycloaddition …
Control of the Stereochemical Course of [4+2] Cycloaddition during trans-Decalin Formation by Fsa2-Family Enzymes.
Kato N, Nogawa T, Takita R, Kinugasa K, Kanai M, Uchiyama M, Osada H, Takahashi S. Kato N, et al. Angew Chem Int Ed Engl. 2018 Jul 26;57(31):9754-9758. doi: 10.1002/anie.201805050. Epub 2018 Jul 4. Angew Chem Int Ed Engl. 2018. PMID: 29972614
To understand the mechanisms by which fsa2 determines the stereochemistry of reaction products, we sought an fsa2 homologue that is involved in trans-decalin formation in the biosynthetic pathway of an enantiomerically opposite analogue, and we found phm7, which is involved in th …
To understand the mechanisms by which fsa2 determines the stereochemistry of reaction products, we sought an fsa2 homologue that is involved …
Phoma Saccardo: distribution, secondary metabolite production and biotechnological applications.
Rai M, Deshmukh P, Gade A, Ingle A, Kövics GJ, Irinyi L. Rai M, et al. Crit Rev Microbiol. 2009;35(3):182-96. doi: 10.1080/10408410902975992. Crit Rev Microbiol. 2009. PMID: 19624254 Review.
., Sirodesmins, Phomenoic acid, Phomenolactone, Phomadecalins, Phomactin A, Phomasetin, Squalestatin-1 (S1), and Squalestatin-2 (S2). The secondary metabolites secreted by some species of Phoma are antitumor, antimicrobial, and anti-HIV. Equisetin and Phomasetin obt …
., Sirodesmins, Phomenoic acid, Phomenolactone, Phomadecalins, Phomactin A, Phomasetin, Squalestatin-1 (S1), and Squalestatin-2 (S2). …
Natural products with anti-HIV activity from marine organisms.
Tziveleka LA, Vagias C, Roussis V. Tziveleka LA, et al. Curr Top Med Chem. 2003;3(13):1512-35. doi: 10.2174/1568026033451790. Curr Top Med Chem. 2003. PMID: 14529524 Review.
Nothogenia fastigiata, Aghardhiella tenera); the peptides tachyplesin and polyphemusin, which are highly abundant in hemocyte debris of the horseshoe crabs Tachypleus tridentatus and Limulus polyphemus; sponge metabolites such as avarol, avarone, ilimaquinone and several phlorogl …
Nothogenia fastigiata, Aghardhiella tenera); the peptides tachyplesin and polyphemusin, which are highly abundant in hemocyte debris of the …
Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12.
Mao Z, Wang W, Su R, Gu G, Liu ZL, Lai D, Zhou L. Mao Z, et al. Molecules. 2019 Dec 27;25(1):114. doi: 10.3390/molecules25010114. Molecules. 2019. PMID: 31892246 Free PMC article.
The structures of the new compounds were elucidated by analysis of the spectroscopic data, including NMR, HRMS and ECD, and by chemical conversion. Compounds 1 and 2 were phomasetin analogues, and both showed potent larvicidal activity against the fourth-instar larvae of A …
The structures of the new compounds were elucidated by analysis of the spectroscopic data, including NMR, HRMS and ECD, and by chemical conv …
Pyrenosetins A-C, New Decalinoylspirotetramic Acid Derivatives Isolated by Bioactivity-Based Molecular Networking from the Seaweed-Derived Fungus Pyrenochaetopsis sp. FVE-001.
Fan B, Dewapriya P, Li F, Blümel M, Tasdemir D. Fan B, et al. Mar Drugs. 2020 Jan 11;18(1):47. doi: 10.3390/md18010047. Mar Drugs. 2020. PMID: 31940767 Free PMC article.
This approach led to a rapid isolation of three new decalinoylspirotetramic acid derivatives, pyrenosetins A-C (1-3) and the known decalin tetramic acid phomasetin (4). The structures of the compounds were elucidated by extensive NMR, HR-ESIMS, FT-IR spectroscopy, [alpha]( …
This approach led to a rapid isolation of three new decalinoylspirotetramic acid derivatives, pyrenosetins A-C (1-3) and the known decalin t …
Current lead natural products for the chemotherapy of human immunodeficiency virus (HIV) infection.
De Clercq E. De Clercq E. Med Res Rev. 2000 Sep;20(5):323-49. doi: 10.1002/1098-1128(200009)20:5<323::aid-med1>3.0.co;2-a. Med Res Rev. 2000. PMID: 10934347 Review.
Curcumin (diferuloylmethane, from turmeric, the roots/rhizomes of Curcuma spp), dicaffeoylquinic and dicaffeoylt artaric acids, L-chicoric acid, and a number of fungal metabolites (equisetin, phomasetin, oteromycin, and integric acid) have all been proposed as HIV-1 integr …
Curcumin (diferuloylmethane, from turmeric, the roots/rhizomes of Curcuma spp), dicaffeoylquinic and dicaffeoylt artaric acids, L-chicoric a …
Pyrrolocin A, a 3-Decalinoyltetramic Acid with Selective Biological Activity, Isolated from Amazonian Cultures of the Novel Endophyte Diaporthales sp. E6927E.
Patridge EV, Darnell A, Kucera K, Phillips GM, Bokesch HR, Gustafson KR, Spakowicz DJ, Zhou L, Hungerford WM, Plummer M, Hoyer D, Narváez-Trujillo A, Phillips AJ, Strobel SA. Patridge EV, et al. Nat Prod Commun. 2015 Oct;10(10):1649-54. Nat Prod Commun. 2015. PMID: 26669095 Free PMC article.
The structure of the natural product was solved using NMR and CD spectroscopy and it is structurally related to the fungal setins, equisetin and phomasetin, which are well-characterized tetramic acid antibiotics specific for Gram-positive organisms. ...
The structure of the natural product was solved using NMR and CD spectroscopy and it is structurally related to the fungal setins, equisetin …
A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis.
Kato N, Nogawa T, Hirota H, Jang JH, Takahashi S, Ahn JS, Osada H. Kato N, et al. Biochem Biophys Res Commun. 2015 May 1;460(2):210-5. doi: 10.1016/j.bbrc.2015.03.011. Epub 2015 Mar 11. Biochem Biophys Res Commun. 2015. PMID: 25770422
Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. ...
Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioac …
11 results