Terpenoids from the Liverwort Plagiochila fruticosa and Their Antivirulence Activity against Candida albicans.

Fourteen new terpenoids plagicosins A-N (1-14), including seven sesquiterpenoids (1-7) consisting of six ent-bicyclogermacrenes and one ent-2,3-seco-aromadendrane, as well as seven diterpenoids (8-14) comprising five fusicoccanes, a eunicellane, and a rare gersemiane, were isolated from the Chinese liverwort Plagiochila fruticosa Mitt. The structures of these terpenoids were determined on the basis of comprehensive analysis of MS and NMR spectroscopic data coupled with electronic circular dichroism (ECD) and coupling constant calculations. Plagicosin F (6) displayed potent antivirulence activity through inhibiting the hyphal morphogenesis, adhesion, and biofilm formation of Candida albicans. The genes related to hyphal formation were regulated by 6.

• Publication year

  2020

• Venue

  Journal of Natural Products

• Publication date

  2020-06-01

• Fields of study

  Biology, Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1021/acs.jnatprod.9b00895PMID 32479076
• 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.

• Efflux pump-mediated resistance to antifungal compounds can be prevented by conjugation with triphenylphosphonium cation

  2018cited by this paper
• Biatriosporin D displays anti‐virulence activity through decreasing the intracellular cAMP levels

  2017cited by this paper
• Eudesmane sesquiterpenes from Chinese liverwort are substrates of Cdrs and display antifungal activity by targeting Erg6 and Erg11 of Candida albicans.

  2017cited by this paper
• Candidalysin is a fungal peptide toxin critical for mucosal infection

  2016cited by this paper
• Preparative Scale MS-Guided Isolation of Bioactive Compounds Using High-Resolution Flash Chromatography: Antifungals from Chiloscyphus polyanthos as a Case Study

  2016cited by this paper
• Gersemiols A-C and Eunicellol A, Diterpenoids from the Arctic Soft Coral Gersemia fruticosa.

  2016cited by this paper
• Diorcinol D Exerts Fungicidal Action against Candida albicans through Cytoplasm Membrane Destruction and ROS Accumulation

  2015cited by this paper
• Relativistic force field: parametric computations of proton-proton coupling constants in (1)H NMR spectra.

  2014cited by this paper
• Activation of Defense Mechanisms against Pathogens in Mosses and Flowering Plants

  2013cited by this paper
• Retigeric acid B enhances the efficacy of azoles combating the virulence and biofilm formation of Candida albicans.

  2012cited by this paper
• Growth of Candida albicans hyphae

  2011cited by this paper
• Bisbibenzyls, a New Type of Antifungal Agent, Inhibit Morphogenesis Switch and Biofilm Formation through Upregulation of DPP3 in Candida albicans

  2011cited by this paper
• Bioactive sesqui- and diterpenoids from the Argentine liverwort Porella chilensis.

  2011cited by this paper
• The origin and evolution of lignin biosynthesis.

  2010cited by this paper
• Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods.

  2007cited by this paper
• Three ent-eudesmenones from the liverwort Plagiochila bifaria.

  2006cited by this paper
• Candida albicans biofilm development, modeling a host-pathogen interaction.

  2006cited by this paper
• Chemosystematics of the hepaticae.

  2004cited by this paper
• Sesquiterpene constituents from the essential oils of the liverworts Mylia taylorii and Mylia nuda.

  2004cited by this paper
• Attributable mortality of nosocomial candidemia, revisited.

  2003cited by this paper
• Cytotoxic 2,3-Secoaromadendrane-Type Sesquiterpenoids from the Liverwort Plagiochila ovalifolia

  1998cited by this paper
• Gymnomitrane-type sesquiterpenoids from the liverwort Plagiochila trabeculata

  1988cited by this paper
• Lower Devonian Gametophytes: Relation to the Phylogeny of Land Plants

  1982cited by this paper

• Natural product-derived antifungals against Candida albicans: Chemical diversity and mechanisms of action.

  2025cites this paper
• Phytochemistry of Bryophytes: Biologically Active Compounds and Their Uses as Cosmetics, Foods, and in Drug Development.

  2025cites this paper
• A new verrucosane diterpenoid from the Vietnamese liverwort Plagiochila bantamensis.

  2025cites this paper
• Natural Inhibitors Against Severe Acute Respiratory Syndrome Coronavirus 2 Main Protease From Three Vietnamese Bryophytes

  2025cites this paper
• Inhibitory effects and mode of antifungal action of isobavachalcone on Candida albicans growth and virulence factors.

  2024cites this paper
• Computation-guided scaffold exploration of 2E,6E-1,10-trans/cis-eunicellanes

  2024cites this paper
• Insights into the anti‐Candida albicans properties of natural phytochemicals: An in vitro and in vivo investigation

  2024cites this paper
• Structural-model-based genome mining can efficiently discover novel non-canonical terpene synthases hidden in genomes of diverse species

  2024cites this paper
• Ent-eudesmane sesquiterpenoids from the Chinese liverwort Chiloscyphus polyanthus.

  2023cites this paper
• Discovery and Anticancer Activity of the Plagiochilins from the Liverwort Genus Plagiochila

  2023cites this paper
• Natural products as antifungal agents against invasive fungi.

  2023cites this paper
• The Plagiochilins from Plagiochila Liverworts: Binding to α-Tubulin and Drug Design Perspectives

  2023cites this paper
• Aquilaria sinensis (Lour.) Spreng: Phytochemical review and Chemotaxonomic values

  2022cites this paper
• Recent progress on anti-Candida natural products.

  2021cites this paper
• Suppression of hyphal formation and virulence of Candida albicans by natural and synthetic compounds

  2021cites this paper
• Phloretin inhibited the pathogenicity and virulence factors against Candida albicans

  2021cites this paper
• Recent literature on bryophytes — 124(2)

  2021cites this paper
• Campafungins: Inhibitors of Candida albicans and Cryptococcus neoformans Hyphal Growth.

  2020cites this paper