Secondary metabolites with fungicide potentials from the deep-sea seamount-derived fungus Talaromyces scorteus AS-242.

Marine natural products play an important role in biopesticides. Seven new secondary metabolites with different structural classes, including two cycloheptapeptides, scortide A (1) and scortide B (2), two 19-nor-diterpenoids, talascortene H (3) and talascortene I (4), two diterpenoid acids, talascortene J (5) and talascortene K (6), and one triterpenoid, talascortene L (7) were isolated and identified from the sea-anemone-derived endozoic fungus Talaromyces scorteus AS-242. Their structures were comprehensively assigned by spectroscopic data analysis, single-crystal X-ray diffraction, tandem mass spectrometry, and electronic circular dichroism (ECD) calculations.

Antifungal Pseuboyenes A-J, Bergamotene-Derived Sesquiterpenoids from a Cold-Seep-Derived .

A chemical investigation of a cold-seep-sediment-derived fungus, CS-793, resulted in characterization of 10 novel bergamotene-derived sesquiterpenoids, pseuboyenes A-J (-). Their structures were elucidated by spectroscopic and X-ray crystallographic analyses as well as using the modified Mosher's method. Compound represents the first example of a -bergamotene containing a 6-oxobicyclo[3.

Discovery of (±)-Penindolenes Reveals an Unusual Indole Ring Cleavage Pathway Catalyzed by P450 Monooxygenase.

(±)-Penindolenes A-D (1-4), the first representatives of indole terpenoids featuring a γ-lactam skeleton, were isolated from the mangrove-derived endophytic fungus Penicillium brocae MA-231. Our bioactivity tests revealed their potent antimicrobial and acetylcholinesterase inhibitory activities. The biosynthetic reactions by the five enzymes PbaABCDE leading to γ-lactam ring formation were identified with heterologous expression and in vitro enzymatic assays.

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus CS-793.

Pseudallenes A and B ( and ), the new and rare examples of sulfur-containing ovalicin derivatives, along with three known analogues -, were isolated and identified from the culture extract of CS-793, a fungus obtained from the deep-sea cold seep sediments. Their structures were established by detailed interpretation of NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis confirmed and established the structures and absolute configurations of compounds -, thus providing the first characterized crystal structure of an ovalicin-type sesquiterpenoid.

Curvularin derivatives from the marine mangrove derived fungus Penicillium sumatrense MA-325.

Sumalarins D-G (1-4), four previously undescribed curvularin derivatives, along with two known related metabolites, curvularin (5) and dehydrocurvularin (6), were isolated and identified from the mangrove-derived fungus Penicillium sumatrense MA-325. Among them, sumalarin D (1) represents a unique example of curvularin derivative featuring a 5-methylfuran-2-yl-methyl group. Their structures were elucidated based on analysis of NMR and MS data as well as comparison of ECD spectra and quantum chemical calculations of NMR, and compound 1 was confirmed by X-ray crystallographic analysis.

A new steroid with potent antimicrobial activities and two new polyketides from Penicillium variabile EN-394, a fungus obtained from the marine red alga Rhodomela confervoides.

Three new compounds, including one steroid named penivariod A (1) and two polyketides penivarides A and B (2 and 3), as well as six known derivatives (4-9) were isolated from Penicillium variabile EN-394, a fungus afforded from the marine red alga Rhodomela confervoides. Their structures were elucidated by analysis of the HRESIMS, 1D and 2D NMR. The absolute stereochemistry was determined by X-ray crystallographic data, gauge-independent atomic orbital (GIAO) NMR shift calculation followed by DP4+ analysis combined with calculated electronic circular dichroism (ECD).

Antimicrobial polyketides from Magellan Seamount-derived fungus Talaromyces scorteus AS-242.

Two new nonadride derivatives, namely, talarodrides G and H (1 and 2), and one new depsidone derivative, botryorhodine K (3), together with a known nonadride analogue (4), were characterized from the Magellan Seamount-derived fungus Talaromyces scorteus AS-242. Their structures were established by detailed interpretation of NMR spectroscopic and mass spectrometry data analysis. X-ray crystallographic analysis of compounds 1 and 3 confirmed their structures and absolute configurations, representing the first characterized crystal structure of a nonadride-type polyketide.

Molecular insights into the catalytic promiscuity of a bacterial diterpene synthase.

Diterpene synthase VenA is responsible for assembling venezuelaene A with a unique 5-5-6-7 tetracyclic skeleton from geranylgeranyl pyrophosphate. VenA also demonstrates substrate promiscuity by accepting geranyl pyrophosphate and farnesyl pyrophosphate as alternative substrates. Herein, we report the crystal structures of VenA in both apo form and holo form in complex with a trinuclear magnesium cluster and pyrophosphate group.

Isolation and characterization of three pairs of verrucosidin epimers from the marine sediment-derived fungus and configuration revision of penicyrone A and related analogues.

Unlabelled: Verrucosidins, a methylated α-pyrone class of polyketides rarely reported upon, have been implicated in one or more neurological diseases. Despite the significance of verrucosidins as neurotoxins, the absolute configurations of most of the derivatives have not been accurately characterized yet. In this study, three pairs of C-9 epimeric verrucosidin derivatives, including the known compounds penicyrones A and B () and 9--methylpenicyrones A and B (), the new compounds 9-ethylpenicyrones A and B (), together with the related known derivative verrucosidin (), were isolated and identified from the culture extract of SD-413, which was obtained from the marine sediment collected from the East China sea.

Oxepine-containing pyrazinopyrimidine alkaloids and quinolinone derivatives produced by Aspergillus versicolor AS-212, a deep-sea-derived endozoic fungus.

Four new oxepine-containing pyrazinopyrimidine alkaloids, versicoxepines A - D (1-4), two quinolinone alkaloid analogs including 3-hydroxy-6-methoxy-4-phenylquinolin-2(1H)-one (5) and 3-methoxy-6-hydroxy-4-phenylquinolin-2(1H)-one (6) which were new naturally occurring compounds, together with two known compounds (7 and 8) were isolated from Aspergillus versicolor AS-212, an endozoic fungus isolated from the deep-sea coral Hemicorallium cf. imperiale, which was collected from the Magellan Seamounts in the Western Pacific Ocean. Their structures were determined by extensive analysis of the spectroscopic and X-ray crystallographic data as well as by chiral HPLC analysis, ECD calculation, and DP4+ probability prediction.

Rubensteroid A, a new steroid with antibacterial activity from Penicillium rubens AS-130.

A new steroid with strong antibacterial activity, rubensteroid A (1), along with its decarboxylic analogue, solitumergosterol A (2), were isolated and identified from the Magellan Seamount-derived fungus Penicillium rubens AS-130. The structure and absolute configuration of compound 1 were established by detailed interpretation of NMR spectroscopic analysis, mass spectrometry data, and TDDFT-ECD calculations. Compound 1 had a rare 6/6/6/6/5 pentacyclic system, which might be the [4 + 2] Diels-Alder adduct of 14,15-didehydroergosterol (14-DHE) cycloaddition with maleic acid or maleimide, followed by decarboxylation.

Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts.

Two new quinazolinone diketopiperazine alkaloids, including versicomide E () and cottoquinazoline H (), together with ten known compounds (, , and -) were isolated and identified from AS-212, an endozoic fungus associated with the deep-sea coral cf. , which was collected from the Magellan Seamounts. Their chemical structures were determined by an extensive interpretation of the spectroscopic and X-ray crystallographic data as well as specific rotation calculation, ECD calculation, and comparison of their ECD spectra.

Antimicrobial polyketides and sesquiterpene lactones from the deep-sea cold-seep-derived fungus CS-113 triggered by the histone deacetylase inhibitor SAHA.

Seven new highly oxygenated natural products with diverse chemical structural types, including three new glucosidic polyketides, talaminiosides A-C (1-3), a pair of racemic aromatic polyketides, (±)-talaminone A (4a and 4b), two new azaphilone polyketides, (+)-5-chloromitorubrinic acid (5) and 7--purpurquinone C (7), and one new drimane sesquiterpene lactone, 11-hydroxyminioluteumide B (8), together with a pinazaphilone B sodium salt (6) and 10 known compounds (9-18), were isolated and identified from the culture extract of CS-113, a fungus obtained from deep-sea cold-seep sediments collected from the South China Sea. LCMS results indicated that compounds 3 and 4 might be produced by the real activation of silent BGCs triggered by the histone deacetylase inhibitor SAHA, and some of the other compounds were enhanced minor components. Their structures were elucidated by the detailed interpretation of NMR spectroscopic and mass spectrometric data, X-ray crystallographic analysis, ECD and specific rotation (SR) calculations, and DP4+ probability analysis.

New Polyketide and Sesquiterpenoid Derivatives from the Magellan Seamount-Derived Fungus Penicillium rubens AS-130.

Rubenpolyketone A (1), a polyketide featuring a new carbon skeleton having cyclohexenone condensed with a methyl octenone chain and a new linear sesquiterpenoid, chermesiterpenoid D (2), together with seven known secondary metabolites (3-9) were isolated and identified from the Magellan Seamount-derived fungus Penicillium rubens AS-130. Their structures were determined based on detailed analysis of NMR and mass spectroscopic data and the absolute configurations of these two new compounds were elucidated by the combination of quantum mechanical (QM)-NMR and time-dependent density functional (TDDFT) ECD calculation approaches. Chermesiterpenoids B (3) and C (4) showed potent inhibitory activities against the aquatic pathogen Vibrio anguillarum with MIC values of 0.

Mining new meroterpenoids from the marine red alga-derived endophytic Penicillium chermesinum EN-480 by comparative transcriptome analysis.

As the development of genetic and bioinformatic, the strategy of "bottom-up", combined with genome and transcriptome techniques, was considered as an efficient and practical method to break through the limitation of traditional discovery of natural products. Generally, comparative transcriptome analysis could be useful to guide the optimization of fungal cultivation conditions in which the transcriptional level of interesting compounds is higher. The transcriptome analysis of the algal endophytic fungus Penicillium chermesinum EN-480 indicated that fermentation of this fungus in modified rice solid medium could produce some metabolites different from those cultivated in other media.

New Cytochalasin Derivatives from Deep-Sea Cold Seep-Derived Endozoic Fungus Curvularia verruculosa CS-129.

Two new antimicrobial cytochalasin derivatives, 6β,7β-epoxydeoxaphomin C (1) and 12-hydroxydeoxaphomin C (2), a new natural occurring product 24-nor-cytochalasin B (3), together with two related known analogs (4-5) were isolated and identified from an endozoic fungus Curvularia verruculosa CS-129, isolated from the deep-sea squat lobster Shinkaia crosnieri which was collected in cold seep region of south China sea. The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis and ECD calculation. The spectroscopic data of 24-nor-cytochalasin B (3) were reported for the first time.

Uncommon Polyketides from AS-324, a Marine Endozoic Fungus Isolated from Deep-Sea Coral in the Magellan Seamount.

Four unusual steckwaic acids E-H (-), possessing a rarely described acrylic acid unit at C-4 (-) or a double bond between C-12 and C-13 () are reported for the first time, along with four new analogues (-) and two known congeners ( and ). They were purified from the organic extract of AS-324, an endozoic fungus obtained from a deep-sea coral sp., which was collected from the Magellan Seamount at a depth of 1458 m.

Tanzawaic Acid Derivatives: Fungal Polyketides from the Deep-Sea Coral-Derived Endozoic AS-324.

Ten new tanzawaic acids, namely, steckwaic acids A-D (-), 11-ketotanzawaic acid D (), 6,15-dihydroxytanzawaic acid M (), 15-methoxytanzawaic acid M (), 15-methoxytanzawaic acid M (), 8-hydroxytanzawaic acid M (), and 8-hydroxytanzawaic acid B (), together with four known analogues (-), were isolated and identified from the endozoic fungus AS-324, which was obtained from a deep-sea sp. coral that was collected from the Magellan seamount in the Western Pacific Ocean. Structurally, steckwaic acids A-D (-) represent the first tanzawaic acid derivatives containing a naphthalene ring.

Sesquiterpene and Sorbicillinoid Glycosides from the Endophytic Fungus EN-586 Derived from the Marine Red Alga .

An unusual sesquiterpene glycoside trichoacorside A () and two novel sorbicillinoid glycosides sorbicillisides A () and B (), together with a known compound sorbicillin (), were isolated and identified from the culture extract of an endophytic fungus EN-586, obtained from the marine red alga . Trichoacorside A () is the first representative of a glucosamine-coupled acorane-type sesquiterpenoid. Their structures were elucidated based on detailed interpretation of NMR and mass spectroscopic data.

Effect of wound irrigation on the prevention of surgical site infections: A meta-analysis.

We performed a meta-analysis to evaluate the effect of wound irrigation on the prevention of surgical site infections. A systematic literature search up to January 2022 was done and 24 studies included 4967 subjects under surgery at the start of the study; antibiotic irrigation was used with 1372 of them, 1261 were aqueous povidone-iodine irrigation, and 2334 were saline irrigation or no irrigation for surgical site infections prevention in all surgical populations. We calculated the odds ratio (OR) with 95% confidence intervals (CIs) to evaluate the effect of different wound irrigation on the prevention of surgical site infections by the dichotomous method with a random or fixed-influence model.

Isolation and Characterization of Antibacterial Carotane Sesquiterpenes from Associated Endophytic QA-8.

Carotane sesquiterpenes are commonly found in plants but are infrequently reported in the fungal kingdom. Chemical investigation of QA-8, an endophytic fungus associated with the inner root tissue of the grown medicinal herb H. Lév.

Secondary Metabolites with Agricultural Antagonistic Potentials from , a Marine-Derived Entomopathogenic Fungus.

Soil-borne pathogens and weeds could synergistically affect vegetable growth and result in serious losses. The investigation of antagonistic metabolites from a marine-derived entomopathogenic fungus, , obtained polyhydroxy steroid (), tricyclic diterpenoid (), isaridin (), and destruxin cyclodepsipeptides (). The structures and absolute configurations of new were elucidated by extensive spectroscopic and X-ray crystallographic analyses, as well as electronic circular dichroism (ECD) calculations.

Progress in Research on Bioactive Secondary Metabolites from Deep-Sea Derived Microorganisms.

Deep sea has an extreme environment which leads to biodiversity of microorganisms and their unique physical and biochemical mechanisms. Deep-sea derived microorganisms are more likely to produce novel bioactive substances with special mechanism of action for drug discovery. This article reviews secondary metabolites with biological activities such as anti-tumor, anti-bacterial, anti-viral, and anti-inflammatory isolated from deep-sea fungi and bacteria during 2018-2020.

Polyketides and Terpenoids with Potent Antibacterial Activities from the Artemisia argyi-Derived Fungus Trichoderma koningiopsis QA-3.

The AcOEt extract of Artemisia argyi-derived fungus Trichoderma koningiopsis QA-3 showed potent inhibitory activity against pathogenic bacteria. Fractionation of the extract resulted in the isolation of three new polyketides (1-3) and two new terpenoids (4 and 5), together with three known metabolites (6-8). Their chemical structures were analyzed by NMR spectra, ECD, HR-ESI-MS or HR-EI-MS, optical rotation, and X-ray crystallographic data, as well as by comparison with literature reports.