New Antibacterial Chloro-Containing Polyketides from the Alga-Derived Fungus Asteromyces cruciatus KMM 4696

Zhuravleva, Olesya I.; Oleinikova, G. K.; Антонов, А. С.; Киричук, Н. Н.; Pelageev, Dmitry N.; Rasin, Anton B.; Menshov, Alexander S.; Popov, Roman S.; Kim, Natalya Yu.; Chingizova, Ekaterina A.; Chingizov, Artur R.; Volchkova, Olga O.; Amsberg, Gunhild von; Dyshlovoy, Sergey A.; Yurchenko, Ekaterina A.; Guzhova, Irina V.; Yurchenko, Anton N.

doi:10.3390/jof8050454

Cited by 11 publications

(15 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…83 Five new chlorinated polyketides, acrucipentynes A−E (189− 193), are found in the fungus Asteromyces cruciatus KMM 4696, which is associated with an unnamed alga from Vostok Bay in the Sea of Japan. 84 The epoxide acrucipentyne F corresponding to D and E is also present in this fungus. To varying degrees, the new acrucipentynes inhibit sortase A activity, bacterial growth, and biofilm formation, and decrease LDH release from human keratinocytes.…”

Section: ■ Marine Fungimentioning

confidence: 84%

See 1 more Smart Citation

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

Gribble

2024

J. Nat. Prod.

View full text Add to dashboard Cite

The discovery of naturally occurring organohalogen compounds has increased astronomically in the 55 years since they were first discovered�from fewer than 50 in 1968 to a combined 7,958 described examples in three comprehensive reviews. The present survey, which covers the period 2021−2023, brings the number of known natural organohalogens to approximately 8,400. The organization is according to species origin, and coverage includes marine and terrestrial plants, fungi, bacteria, marine sponges, corals, cyanobacteria, tunicates, and other marine organisms.

show abstract

Section: ■ Marine Fungimentioning

confidence: 84%

“…Five new chlorinated polyketides, acrucipentynes A–E ( 189 – 193 ), are found in the fungus Asteromyces cruciatus KMM 4696, which is associated with an unnamed alga from Vostok Bay in the Sea of Japan . The epoxide acrucipentyne F corresponding to D and E is also present in this fungus.…”

Section: Marine Fungimentioning

confidence: 99%

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

Gribble

2024

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…It was previously shown that strain A. cruciatus KMM 4696 can produce the first chlorine-contained monocyclic cyclohexanols containing a 3-methylbutenynyl unit that obviously originated from a tetraketide precursor [ 7 ]. Benzopyranes 10 and 11 obviously originated from the same precursor.…”

Section: Discussionmentioning

confidence: 99%

“…Recently, chlorine-containing compounds acrucipentyns A–F were isolated by us from Asteromyces cruciatus KMM4696 fungus associated with brown alga Sargassum pallidum , and these compounds showed significant antibacterial activity against Staphylococcus aureus [ 7 ]. The detailed separation of the non-polar part of this fungal extract resulted in the isolation of a number of new and known anthraquinone derivatives.…”

Section: Introductionmentioning

confidence: 99%

Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus

Zhuravleva,

Chingizova,

Oleinikova

et al. 2023

Marine Drugs

Self Cite

View full text Add to dashboard Cite

New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds 1–4 and 6–13 showed a significant antimicrobial effects against Staphylococcus aureus growth, and acruciquinone A (1), dendryol B (4), coniothyrinone B (7), and ω-hydroxypachybasin (9) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding 4, inhibited urease activity. We studied the effects of anthraquinones 1, 4, 7, and 9 and coniothyrinone D (6) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with S. aureus. Anthraquinones significantly reduce the negative impact of S. aureus on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (1) revealed the most pronounced effect.

show abstract

“…As the most active compound, 210 also showed moderate cytotoxicity (IC 50 = 14.8 μM) [ 97 ]. Some other new antibacterial chloro-containing polyketides were identified from alga-derived fungus [ 98 ]. Furthermore, isochromophilone IX ( 212 ) presented outstanding antibacterial activity against MRSA (MIC = 50 μg/mL) [ 99 ].…”

Section: Aromaticsmentioning

confidence: 99%

Secondary Metabolites from Coral-Associated Fungi: Source, Chemistry and Bioactivities

Chen

Pang

et al. 2022

JoF

View full text Add to dashboard Cite

Our study of the secondary metabolites of coral-associated fungi produced a valuable and extra-large chemical database. Many of them exhibit strong biological activity and can be used for promising drug lead compounds. Serving as an epitome of the most promising compounds, which take the ultra-new skeletons and/or remarkable bioactivities, this review presents an overview of new compounds and bioactive compounds isolated from coral-associated fungi, covering the literature from 2010 to 2021. Its scope included 423 metabolites, focusing on the bioactivity and structure diversity of these compounds. According to structure, these compounds can be roughly classified as terpenes, alkaloids, peptides, aromatics, lactones, steroids, and other compounds. Some of them described in this review possess a wide range of bioactivities, such as anticancer, antimicrobial, antifouling, and other activities. This review aims to provide some significant chemical and/or biological enlightenment for the study of marine natural products and marine drug development in the future.

show abstract

New Antibacterial Chloro-Containing Polyketides from the Alga-Derived Fungus Asteromyces cruciatus KMM 4696

Cited by 11 publications

References 36 publications

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus

Secondary Metabolites from Coral-Associated Fungi: Source, Chemistry and Bioactivities

Contact Info

Product

Resources

About