Cytotoxic anthrone-cyclopentenone heterodimers from the fungus Penicillium sp. guided by molecular networking.

(±)-Penicithrones A-D (1a/1b-4a/4b), four novel pairs of anthrone-cyclopentenone heterodimers characterized by a distinctive bridged 6/6/6-5 tetracyclic core skeleton, together with three previously identified compounds (5-7), were isolated from the crude extract of the mangrove-derived fungus Penicillium sp., guided by heteronuclear single quantum correlation (HSQC)-based small molecule accurate recognition technology (SMART 2.0) and liquid chromatography-tandem mass spectrometry (LC-MS/MS)-based molecular networking. The structural elucidation of new compounds was accomplished through comprehensive spectroscopic analysis, and their absolute configurations were determined using DP4+ 13C nuclear magnetic resonance (NMR) calculations and electronic circular dichroism (ECD) calculations. Compounds 1a/1b-4a/4b demonstrated moderate cytotoxicity against three human cancer cell lines HeLa, HCT116 and MCF-7 with half maximal inhibitory concentration (IC50) values ranging from 15.95 ± 1.64 to 28.56 ± 2.59 μmol·L-1.

• Publication year

  2025

• Venue

  Chinese Journal of Natural Medicines

• Publication date

  2025-10-01

• Fields of study

  Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1016/s1875-5364(25)60858-2PMID 41073065
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• New bioactive secondary metabolites from fungi: 2023

  2024cited by this paper
• Multioxidized polyketides from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata.

  2024cited by this paper
• New Cytotoxic γ-Lactam Alkaloids from the Mangrove-Derived Fungus Talaromyces hainanensis sp. nov. Guided by Molecular Networking Strategy.

  2024cited by this paper
• Progress in approved drugs from natural product resources.

  2024cited by this paper
• Marine natural products.

  2024cited by this paper
• Comparative genomic study of the Penicillium genus elucidates a diverse pangenome and 15 lateral gene transfer events

  2023cited by this paper
• New prenylated indole-benzodiazepine-2,5-diones with α-glucosidase inhibitory activities from the mangrove-derived Aspergillus spinosus.

  2023cited by this paper
• Structures and bioactivities of secondary metabolites from Penicillium genus since 2010.

  2022cited by this paper
• New prenylated indole diketopiperazine alkaloids and polyketides from the mangrove-derived fungus Penicillium sp

  2022cited by this paper
• Four new diphenyl ether derivatives from a mangrove endophytic fungus Epicoccum sorghinum.

  2022cited by this paper
• Intertwined Biosynthesis of Skyrin and Rugulosin A Underlies the Formation of Cage-Structured Bisanthraquinones.

  2021cited by this paper
• Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities.

  2021cited by this paper
• Neobulgarones Revisited: Anti and Syn Bianthrones from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD22.

  2021cited by this paper
• Natural Products as Sources of New Drugs over the Nearly Four Decades from 01/1981 to 09/2019.

  2020cited by this paper
• Halogenated Bianthrones From Penicillium roseopurpureum: a Fungal Endophyte of the Marine Alga Petalonia fascia

  2020cited by this paper
• A Convolutional Neural Network-Based Approach for the Rapid Characterization of Molecularly Diverse Natural Products.

  2020cited by this paper
• Three new isocoumarin derivatives from the mangrove endophytic fungus Penicillium sp. YYSJ-3.

  2020cited by this paper
• Penicimeroterpenoids A-C, Meroterpenoids with Rearrangement Skeletons from the Marine-Derived Fungus Penicillium sp. SCSIO 41512.

  2020cited by this paper
• Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

  2020cited by this paper
• Endophytic Paraconiothyrium sp. from Zingiber officinale Rosc. Displays Broad-Spectrum Antimicrobial Activity by Production of Danthron

  2018cited by this paper
• Variecolortins A-C, Three Pairs of Spirocyclic Diketopiperazine Enantiomers from the Marine-Derived Fungus Eurotium sp. SCSIO F452.

  2018cited by this paper
• Simpterpenoid A, a Meroterpenoid with a Highly Functionalized Cyclohexadiene Moiety Featuring gem-Propane-1,2-dione and Methylformate Groups, from the Mangrove-Derived Penicillium simplicissimum MA-332.

  2018cited by this paper
• An Anti-Inflammatory PPAR-γ Agonist from the Jellyfish-Derived Fungus Penicillium chrysogenum J08NF-4.

  2018cited by this paper
• Three Diketopiperazine Alkaloids with Spirocyclic Skeletons and One Bisthiodiketopiperazine Derivative from the Mangrove-Derived Endophytic Fungus Penicillium brocae MA-231.

  2016cited by this paper
• Three pairs of variecolortide enantiomers from Eurotium sp. with caspase-3 inhibitory activity.

  2014cited by this paper
• Mass spectral molecular networking of living microbial colonies

  2012cited by this paper
• A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

  2012cited by this paper
• Albopunctatone, an antiplasmodial anthrone-anthraquinone from the Australian ascidian Didemnum albopunctatum.

  2012cited by this paper
• Total synthesis and structure assignment of the anthrone C-glycoside cassialoin.

  2008cited by this paper
• Aspergiolide A, a novel anthraquinone derivative with naphtho [1,2,3 -de]chromene -2,7 -dione skeleton isolated from a marine-derived fungus Aspergillus glaucus

  2007cited by this paper
• Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species.

  2003cited by this paper
• Cytotoxicity of Rhamnosylanthraquinones and Rhamnosylanthrones from Rhamnus nepalensis.

  2001cited by this paper
• Studies on the metabolic products of Aspergillus fumigatus (J-4). Chemical structure of metabolic products.

  1968cited by this paper

• Indole alkaloids exhibiting hCE2 inhibitory activity from the roots of Paeonia lactiflora using a feature-based molecular network strategy.

  2026cites this paper
• New Pyridinone Alkaloid and Polyketide from the Cordyceps-Colonizing Fungus Pseudogymnoascus roseus.

  2026cites this paper
• Discovery of Meroterpenoids with Antifungal Activity from Deep-Sea-Derived Fungus Acremonium sclerotigenum LW14.

  2025cites this paper