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Irregularly Bridged Epipolythiodioxopiperazines and Related Analogues: Sources, Structures, and Biological Activities

https://doi.org/10.1021/acs.jnatprod.9b01283

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/1521-3773(20001103)39:21<3866::aid-anie3866>3.0.co;2-eopenalex-snapshot

A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents

inferredcites →https://doi.org/10.1002/anie.201407624openalex-snapshot

Biosynthesis of the Halogenated Mycotoxin Aspirochlorine in Koji Mold Involves a Cryptic Amino Acid Conversion

inferredcites →https://doi.org/10.1002/anie.201806740openalex-snapshot

Enzymatic Amide Tailoring Promotes Retro‐Aldol Amino Acid Conversion To Form the Antifungal Agent Aspirochlorine

inferredcites →https://doi.org/10.1002/ijch.201100012openalex-snapshot

Epipolythiodiketopiperazine Alkaloids: Total Syntheses and Biological Activities

inferredcites →https://doi.org/10.1002/slct.201700262openalex-snapshot

Genomics‐Driven Discovery of the Gliovirin Biosynthesis Gene Cluster in the Plant Beneficial Fungus Trichoderma Virens

inferredcites →https://doi.org/10.1016/b978-0-12-179760-7.50016-4openalex-snapshot

Epipolythiopiperazine-3,6-diones

inferredcites →https://doi.org/10.1016/j.phytochem.2014.01.003openalex-snapshot

An antibacterial metabolite from Lasiodiplodia pseudotheobromae F2

inferredcites →https://doi.org/10.1016/j.phytochem.2018.11.007openalex-snapshot

Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L.

inferredcites →https://doi.org/10.1016/j.phytol.2014.12.010openalex-snapshot

Pretrichodermamide C and N-methylpretrichodermamide B, two new cytotoxic epidithiodiketopiperazines from hyper saline lake derived Penicillium sp.

inferredcites →https://doi.org/10.1016/j.tet.2012.11.047openalex-snapshot

Study on absolute configurations of α/α′ chiral carbons of thiodiketopiperazines by experimental and calculated circular dichroism spectra

inferredcites →https://doi.org/10.1016/j.tetlet.2015.09.113openalex-snapshot

Induced production of a new unprecedented epitrithiodiketopiperazine, chlorotrithiobrevamide, by a culture of the marine-derived Trichoderma cf. brevicompactum with dimethyl sulfoxide

inferredcites →https://doi.org/10.1016/j.tetlet.2016.11.028openalex-snapshot

Induced production of a new dipeptide with a disulfide bridge by long-term fermentation of marine-derived Trichoderma cf. brevicompactum

inferredcites →https://doi.org/10.1016/j.tetlet.2017.08.015openalex-snapshot

Eutypellazines N−S, new thiodiketopiperazines from a deep sea sediment derived fungus Eutypella sp. with anti-VRE activities

inferredcites →https://doi.org/10.1016/s0040-4039(00)87270-6openalex-snapshot

Isolation of aspirochlorine (=antibiotic A30641) possessing a novel dithiodiketopiperazine structure from

inferredcites →https://doi.org/10.1016/s0040-4039(00)96792-3openalex-snapshot

Structural revision of aspirochlorine (=antibiotic A30641), a novel epidithiopiperazine-2, 5-dione produced byaspergillus SPP.

inferredcites →https://doi.org/10.1016/s0168-8278(03)00178-8openalex-snapshot

Gliotoxin-mediated apoptosis of activated human hepatic stellate cells

inferredcites →https://doi.org/10.1021/acs.jnatprod.0c00046openalex-snapshot

Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii

inferredcites →https://doi.org/10.1021/acs.jnatprod.5b00102openalex-snapshot

Bisthiodiketopiperazines and Acorane Sesquiterpenes Produced by the Marine-Derived Fungus Penicillium adametzioides AS-53 on Different Culture Media

inferredcites →https://doi.org/10.1021/acs.jnatprod.5b00669openalex-snapshot

Induced Production of Halogenated Epidithiodiketopiperazines by a Marine-Derived Trichoderma cf. brevicompactum with Sodium Halides

inferredcites →https://doi.org/10.1021/acs.jnatprod.6b00483openalex-snapshot

Penicisulfuranols A–F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309

inferredcites →https://doi.org/10.1021/acs.jnatprod.9b01242openalex-snapshot

Amphiepicoccins A–J: Epipolythiodioxopiperazines from the Fish-Gill-Derived Fungus Epicoccum nigrum HDN17-88

inferredcites →https://doi.org/10.1021/acs.orglett.5b02311openalex-snapshot

Pseudellones A–C, Three Alkaloids from the Marine-Derived Fungus Pseudallescheria ellipsoidea F42–3

inferredcites →https://doi.org/10.1021/acs.orglett.8b00304openalex-snapshot

Highly Photosensitive Poly-Sulfur-Bridged Chetomin Analogues from Chaetomium cochliodes

inferredcites →https://doi.org/10.1021/cr200173zopenalex-snapshot

Disulfide- and Multisulfide-Containing Metabolites from Marine Organisms

inferredcites →https://doi.org/10.1021/ja00055a025openalex-snapshot

Total synthesis of (.+-.)-aspirochlorine

inferredcites →https://doi.org/10.1021/jm00254a010openalex-snapshot

Antiviral agents. Chemical modifications of a disulfide antibiotic, acetylaranotin

inferredcites →https://doi.org/10.1021/np0204390openalex-snapshot

Trichodermamides A and B, Cytotoxic Modified Dipeptides from the Marine-Derived Fungus Trichoderma virens

inferredcites →https://doi.org/10.1021/np0302201openalex-snapshot

Immunomodulatory Constituents from an Ascomycete, Chaetomium s eminudum

inferredcites →https://doi.org/10.1021/np050141kopenalex-snapshot

Aspirochlorine Class Compounds from Aspergillus flavus Inhibit Azole-Resistant Candida albicans

inferredcites →https://doi.org/10.1021/np070239uopenalex-snapshot

Epicoccins A–D, Epipolythiodioxopiperazines from a Cordyceps-Colonizing Isolate of Epicoccum nigrum

inferredcites →https://doi.org/10.1021/np1000895openalex-snapshot

Thiodiketopiperazines Produced by the Endophytic Fungus Epicoccum nigrum

inferredcites →https://doi.org/10.1021/np400802dopenalex-snapshot

Thiodiketopiperazines from the Marine-Derived Fungus Phoma sp. OUCMDZ-1847

inferredcites →https://doi.org/10.1021/np5007235openalex-snapshot

Indole Alkaloids from Chaetomium globosum

inferredcites →https://doi.org/10.1021/np500822kopenalex-snapshot

Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja

inferredcites →https://doi.org/10.1021/np900654aopenalex-snapshot

Diketopiperazines from the Cordyceps-Colonizing Fungus Epicoccum nigrum

inferredcites →https://doi.org/10.1021/ol061046lopenalex-snapshot

Transformation of an Irregularly Bridged Epidithiodiketopiperazine to Trichodermamide A

inferredcites →https://doi.org/10.1038/nchembio.1187openalex-snapshot

Chaetocin is a nonspecific inhibitor of histone lysine methyltransferases

inferredcites →https://doi.org/10.1039/b413440kopenalex-snapshot

Aspergillazines A–E: novel heterocyclic dipeptides from an Australian strain of Aspergillus unilateralis

inferredcites →https://doi.org/10.1039/c3np70097fopenalex-snapshot

Epidithiodioxopiperazines. occurrence, synthesis and biogenesis

inferredcites →https://doi.org/10.1039/c7ra05774aopenalex-snapshot

Eutypellazines A–M, thiodiketopiperazine-type alkaloids from deep sea derived fungus Eutypella sp. MCCC 3A00281

inferredcites →https://doi.org/10.1039/c7ra10389aopenalex-snapshot

Trichodermamides D–F, heterocyclic dipeptides with a highly functionalized 1,2-oxazadecaline core isolated from the endophytic fungus Penicillium janthinellum HDN13-309

inferredcites →https://doi.org/10.1039/c7ra12081hopenalex-snapshot

Antimicrobial alkaloids produced by the mangrove endophyte Penicillium brocae MA-231 using the OSMAC approach

inferredcites →https://doi.org/10.1074/jbc.m002278200openalex-snapshot

Inactivation of Rabbit Muscle Creatine Kinase by Reversible Formation of an Internal Disulfide Bond Induced by the Fungal Toxin Gliotoxin

inferredcites →https://doi.org/10.1074/jbc.m109.009498openalex-snapshot

Epidithiodiketopiperazines Block the Interaction between Hypoxia-inducible Factor-1α (HIF-1α) and p300 by a Zinc Ejection Mechanism

inferredcites →https://doi.org/10.1080/00021369.1983.10866014openalex-snapshot

Isolation of Aspirochlorine (═Antibiotic A30641) as a True Antimicrobial Constituent of the Antibiotic, Oryzachlorin, fromAspergillus oryzae

inferredcites →https://doi.org/10.1080/14786419.2016.1274894openalex-snapshot

Two new diketopiperazines from the tin mine tailings-derived fungus Schizophyllum commune YIM DT 10058

inferredcites →https://doi.org/10.1080/14786419.2019.1627348openalex-snapshot

Dithiodiketopiperazine derivatives from endophytic fungi Trichoderma harzianum and Epicoccum nigrum

inferredcites →https://doi.org/10.1099/mic.0.27847-0openalex-snapshot

The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis

inferredcites →https://doi.org/10.1111/j.1364-3703.2007.00433.xopenalex-snapshot

Production of the toxin sirodesmin PL by Leptosphaeria maculans during infection of Brassica napus

inferredcites →https://doi.org/10.1139/m83-053openalex-snapshot

Gliovirin, a new antibiotic from Gliocladium virens, and its role in the biological control of Pythium ultimum

inferredcites →https://doi.org/10.1179/135100000101535799openalex-snapshot

Redox sensitive epidithiodioxopiperazines in biological mechanisms of toxicity

inferredcites →https://doi.org/10.1182/blood-2006-07-027326openalex-snapshot

Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress

inferredcites →https://doi.org/10.1515/bc.2007.066openalex-snapshot

Inhibition of inducible tumor necrosis factor-α expression by the fungal epipolythiodiketopiperazine gliovirin

inferredcites →https://doi.org/10.3390/md13063640openalex-snapshot

Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides

inferredcites →https://doi.org/10.3390/md14070122openalex-snapshot

Pretrichodermamides D–F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

inferredcites →https://doi.org/10.7164/antibiotics.29.394openalex-snapshot

A30641, a new epidithiodiketopiperazine with antifungal activity.

inferredcites →https://doi.org/10.7164/antibiotics.35.374openalex-snapshot

A new epidithiodiketopiperazine group antibiotic, FA-2097.

inferredcites →https://doi.org/10.7164/antibiotics.37.667openalex-snapshot

Structure of FA-2097, a new member of the dioxopiperazine antibiotics.

inferredcites →https://doi.org/10.7164/antibiotics.47.942openalex-snapshot

Biosynthesis of gliovirin: Incorporation of L-phenylalanine (1-13C).

inferredcites →https://doi.org/10.7164/antibiotics.52.311openalex-snapshot

Aspirochlorine: A Highly Selective and Potent Inhibitor of Fungal Protein Synthesis.

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Incoming claims: where this work appears in other papers’ reference lists and arguments.

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inferred← citeshttps://doi.org/10.1002/anie.202217212openalex-snapshot

Pretrichodermamide A Biosynthesis Reveals the Hidden Diversity of Epidithiodiketopiperazines

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An ortho‐Quinone Methide Mediates Disulfide Migration in the Biosynthesis of Epidithiodiketopiperazines

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Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways

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Asperstrins A−H: Epipolythiodioxopiperazines from the endophytic fungus Aspergillus nidulans

inferred← citeshttps://doi.org/10.1021/acs.jnatprod.3c00534openalex-snapshot

Cytotoxic Epipolythiodioxopiperazines from the Deep-Sea-Derived Fungus Exophiala mesophila MCCC 3A00939

inferred← citeshttps://doi.org/10.1021/acs.joc.3c01061openalex-snapshot

Mechanistic Investigation of the Degradation Pathways of α–β/α–α Bridged Epipolythiodioxopiperazines (ETPs)

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Prenylemestrins A and B: Two Unexpected Epipolythiodioxopiperazines with a Thioethanothio Bridge from Emericella sp. Isolated by Genomic Analysis

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Unexpected Noremestrin with a Sulfur-Bearing 15-Membered Macrocyclic Lactone from Emericella sp. 1454

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Reconstitution of the Early Stage of Chetomin Biosynthesis in Aspergillus fumigatus Leads to the Production of Epipolythiodioxopiperazines

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Specialized Flavoprotein Promotes Sulfur Migration and Spiroaminal Formation in Aspirochlorine Biosynthesis

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