Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058

Nogawa, Toshihiko; Kato, Naoki; Shimizu, Takeshi; Okano, Akiko; Futamura, Yushi; Takahashi, Shunji; Osada, Hiroyuki

doi:10.1038/ja.2017.103

Cited by 18 publications

(21 citation statements)

References 26 publications

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“…To this end, we searched for fungal strains that produce metabolites containing a decalin that is enantiomerically opposite to that of 1 and found a phomasetin ( 2 )‐producing fungus, Pyrenochaetopsis sp. RK10‐F058 . It should be noted that, although all the stereocenters of 2 are opposite to those of 1 , they have been reported as an HIV‐1 integrase inhibitors .…”

Section: Figurementioning

confidence: 99%

Control of the Stereochemical Course of [4+2] Cycloaddition during trans‐Decalin Formation by Fsa2‐Family Enzymes

et al. 2018

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Enzyme-catalyzed [4+ +2] cycloaddition has been proposed to be akey transformation process in various natural product biosynthetic pathways. Recently Fsa2 was found to be involved in stereospecific trans-decalin formation during the biosynthesis of equisetin, apotent HIV-1 integrase inhibitor.T o understand the mechanisms by which fsa2 determines the stereochemistry of reaction products,w es ought an fsa2 homologue that is involved in trans-decalin formation in the biosynthetic pathway of an enantiomerically opposite analogue,a nd we found phm7, which is involved in the biosynthesis of phomasetin. Ad ecalin skeleton with an unnatural configuration was successfully constructed by gene replacement of phm7 with fsa2, thus demonstrating enzymatic control of all stereochemistry in the [4+ +2] cycloaddition. Our findings highlight enzyme-catalyzed [4+ +2] cycloaddition as as tereochemically divergent step in natural product biosynthetic pathwaysa nd open new avenues for generating derivatives with different stereochemistry.

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Section: Figurementioning

confidence: 99%

Control of the Stereochemical Course of [4+2] Cycloaddition during trans‐Decalin Formation by Fsa2‐Family Enzymes

et al. 2018

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“…It seems that the configuration at C-5 has strong correlation with the larvicidal activities, as the epimer of 1 (i.e., 2) was two times less active than that of 1. Decalin-type tetramic acid metabolites were found to display diverse activities, such as HIV-1 integrase inhibiting activity [19], antibacterial activity [18,[20][21][22], antimalarial activity [23] and anti-parasite activity against Trichomonas vaginalis [24]. Our research revealed these type of compounds also have larvicidal function.…”

Section: Larvicidal Activitiesmentioning

confidence: 69%

Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12

Mao

Wang

et al. 2019

Molecules

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Two new decalin/tetramic acid hybrid metabolites, hyalodendrins A (1) and B (2) were isolated from plant endophytic fungus Hyalodendriella sp. Ponipodef12. 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 Aedes aegypti with the median lethal dose (LC50) values of 10.31 and 5.93 μg/mL, respectively.

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“…To our knowledge, the very first chemical study was published in 2017 by Nogawa et al on a Pyrenochaetopsis sp. isolated from a soil sample collected in Japan [29]. This work reported wakodecalines A, B, two new tricyclic decalin derivatives with a spiro pentanone ring (C) and N-methylated terminal serine moiety as well as phomasetin, a known decalin compound with a terminal tetramic acid function [29].…”

Section: Discussionmentioning

confidence: 99%

“…isolated from a soil sample collected in Japan [29]. This work reported wakodecalines A, B, two new tricyclic decalin derivatives with a spiro pentanone ring (C) and N-methylated terminal serine moiety as well as phomasetin, a known decalin compound with a terminal tetramic acid function [29]. The lack of any other investigation in the literature on chemical constituents or biological activity has initiated our interest into this unexplored fungal taxon.…”

Section: Discussionmentioning

confidence: 99%

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Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087

Fan

Dewapriya

et al. 2020

Marine Drugs

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The fungal genus Pyrenochaetopsis is commonly found in soil, terrestrial, and marine environments, however, has received little attention as a source of bioactive secondary metabolites so far. In a recent work, we reported the isolation and characterization of three new anticancer decalinoyltetramic acid derivatives, pyrenosetins A–C, from the Baltic Fucus vesiculosus-derived endophytic fungus Pyrenochaetopsis sp. FVE-001. Herein we report a new pentacyclic decalinoylspirotetramic acid derivative, pyrenosetin D (1), along with two known decalin derivatives wakodecalines A (2) and B (3) from another endophytic strain Pyrenochaetopsis FVE-087 isolated from the same seaweed and showed anticancer activity in initial screenings. The chemical structures of the purified compounds were elucidated by comprehensive analysis of HR-ESIMS, FT-IR, [α]D, 1D and 2D NMR data coupled with DFT calculations of NMR parameters and optical rotation. Compounds 1–3 were evaluated for their anticancer and toxic potentials against the human malignant melanoma cell line (A-375) and the non-cancerous keratinocyte cell line (HaCaT). Pyrenosetin D (1) showed toxicity towards both A-375 and HaCaT cells with IC50 values of 77.5 and 39.3 μM, respectively, while 2 and 3 were inactive. This is the third chemical study performed on the fungal genus Pyrenochaetopsis and the first report of a pentacyclic decalin ring system from the fungal genus Pyrenochaetopsis.

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Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058

Cited by 18 publications

References 26 publications

Control of the Stereochemical Course of [4+2] Cycloaddition during trans‐Decalin Formation by Fsa2‐Family Enzymes

Control of the Stereochemical Course of [4+2] Cycloaddition during trans‐Decalin Formation by Fsa2‐Family Enzymes

Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12

Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087

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