Chermesins I-N: Bioactive spiromeroterpenoids from the marine-sourced fungus Penicillium chermesinum AS-400.

Six previously undescribed spiromeroterpenoids, chermesins I-N (1-6), were isolated and identified from the marine-sourced fungus Penicillium chermesinum AS-400. Their structures were determined by nuclear magnetic resonance and mass spectroscopic data, and the relative and absolute configurations were confirmed based on nuclear Overhauser effect spectroscopic experiments, electronic circular dichroism (ECD) calculations and X-ray crystallographic analysis, and by comparisons of ECD Cotton effects with those of known congeners as well. Structurally, compound 1 represents the first example of spiromeroterpenoid demethylated at C-4.

Absolute Configuration of 12-Deoxynortryptoquivaline from Ascidian-Derived Fungus Determined by Anisotropic NMR and Chiroptical Spectroscopy.

Tryptoquivalines are highly toxic metabolites initially isolated from the fungus . The relative and absolute configuration of tryptoquivaline derivates was primarily established by comparison of the chemical shifts, NOE data, and ECD calculations. A de novo determination of the complete relative configuration using NMR spectroscopy was challenging due to multiple spatially separated stereocenters, including one nonprotonated carbon.

Control effect of root exudates from mycorrhizal watermelon seedlings on Fusarium wilt and the bacterial community in continuously cropped soil.

Watermelon () is susceptible to wilt disease caused by f. sp (FON). AMF colonization alleviates watermelon wilt and regulates the composition of root exudates, but the effects of mycorrhizal watermelon root exudates on watermelon Fusarium wilt is not well understood.

Aromatic Polyketides from the Deep-Sea Cold-Seep Mussel Associated Endozoic Fungus CS-138.

Five new aromatic polyketides, including a unique benzofuran derivative, talarominine A (), and four chromone analogs talamins A-D (-), along with one known related metabolite, 5-hydroxy-7-methoxy-2,3-dimethylchromone (), were isolated and identified from the CS-138, an endozoic fungus obtained from the deep-sea cold seep mussel . Their chemical structures were elucidated by detailed analysis of their NMR spectra, HRESIMS and X-ray crystallographic data, and by comparison with literature data as well. The antibacterial and DPPH scavenging activities of compounds - were evaluated.

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.

Molecular Design and Structure-Property Investigation of -Dodecylbenzyloxy Ethoxylates.

Nonylphenol ethoxylates (NPEO) exhibit outstanding application performances, especially in stabilizing silicone oil emulsions, but have been globally banned or use-restricted for serious ecological toxicity. A homologous series of nonionic surfactants, -dodecylbenzyloxy ethoxylates (DBEO), are molecularly designed and synthesized as alternatives to NPEO, where the phenolic group of NPEO was replaced by a benzyloxy group to counteract the harmful characteristics of NPEO, while retaining the benefits. Based on computational studies, we propose a hypothesis that has a conjugation reduction effect (CRE) of DBEO relative to NPEO on the surfactant structure and properties that solves the biodegradation problem while maintaining the outstanding emulsifying capacity of NPEO.

Three New Sesquiterpenoids from the Algal-Derived Fungus EN-480.

Secondary metabolites obtained from marine-derived fungi are rich sources of drug candidates. Three new sesquiterpenoids, chermesiterpenoids A-C (-), along with four known alkaloids (-), were isolated and identified from the marine red algal-derived fungus EN-480. The structures of these new sesquiterpenoids were elucidated using detailed analysis of the NMR data and their relative configurations were elucidated using nuclear overhauser effect spectroscopy (NOESY) spectra as well as gauge-independent atomic orbital (GIAO) NMR shift calculations and DP4+ probability analysis.

What dominates the interfacial properties of extended surfactants: Amphipathicity or surfactant shape?

Hypothesis: The properties of conventional surfactants (c-surfactants) are generally accepted to be amphipathicity-dominated, but extended surfactants (e-surfactants) are additionally polypropylene oxide (PPO)-dependent; this additional property makes us wonder how an intramolecular PPO spacer would be "extended" at various interfaces and what is responsible for the excellent all-round properties of e-surfactants.

Experiments: A series of novel sodium medium alkyl chain PPO-b-PEO sulfates (2-ethylhexyl polypropylene oxide-block-polyethylene oxide sulfates, CPES) were designed, synthesized and structurally identified. Tensiometry was applied to estimate the surfactant shape at the air/water surface.

Comparative Study of Conventional/Ethoxylated/Extended n-Alkylsulfate Surfactants.

A series of novel anionic e-surfactants n-C P S was molecular designed and synthesized from long-chain fatty alcohols by polypropoxylation and sulfation followed by neutralization. Excellent all-round performance of extended surfactants (e-surfactants) interests us how a simple polypropylene oxide (PPO) spacer has great effects on properties. By a comparative study of conventional/ethoxylated/extended n-alkylsulfate surfactants, we were surprised to find that e-surfactants are in an obvious rugby shape at the air/water surface according to molecular surface area ( a), and it comes down to the intramolecular PPO spacer coiling and surface-induced collapse.

Three New Indole Diterpenoids from the Sea-Anemone-Derived Fungus Penicillium sp. AS-79.

Three new indolediterpenoids, namely, 22-hydroxylshearinine F (), 6-hydroxylpaspalinine (), and 7--acetylemindole SB (), along with eight related known analogs (-), were isolated from the sea-anemone-derived fungus sp. AS-79. The structures and relative configurations of these compounds were determined by a detailed interpretation of the spectroscopic data, and their absolute configurations were determined by ECD calculations ( and ) and single-crystal X-ray diffraction ().

Three Diketopiperazine Alkaloids with Spirocyclic Skeletons and One Bisthiodiketopiperazine Derivative from the Mangrove-Derived Endophytic Fungus Penicillium brocae MA-231.

Four new diketopiperazines including spirobrocazines A-C (1-3) and brocazine G (4) were characterized from the mangrove-derived Penicillium brocae MA-231. Compounds 1 and 2 had a 6/5/6/5/6 cyclic system with a rare spirocyclic center at C-2. Their structures and absolute configurations were determined by spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction.

Complete mitochondrial genome of the orange clownfish Amphiprion percula (Pisces: Perciformes, Pomacentridae).

In this study we determined the complete mitochondrial (mt) genome of the orange clownfish Amphiprion percula. The circular mtDNA molecule was 16,645 bp in size and the overall nucleotide composition of the H-strand was 29.20% A, 25.

Complete mitochondrial genome of the yellowtail clownfish Amphiprion clarkii (Pisces: Perciformes, Pomacentridae).

In this study we determined the complete mitochondrial (mt) genome of the yellowtail clownfish Amphiprion clarkii using eight consensus primer pairs with a long PCR technique. The circular mtDNA molecule was 16,976 bp in size and the overall nucleotide composition of the H-strand was 29.15% A, 26.

Complete mitochondrial genome of the saddleback clownfish Amphiprion polymnus (Pisces: Perciformes, Pomacentridae).

The complete mitochondrial (mt) genome of the saddleback clownfish Amphiprion polymnus was obtained in this study. The circular mtDNA molecule was 16,804 bp in size and the overall nucleotide composition of the H-strand was 29.59% A, 25.

Nonthermal effect of microwave irradiation in nonaqueous enzymatic esterification.

Microwave has nonthermal effects on enzymatic reactions, mainly caused by the polarities of the solvents and substrates. In this experiment, a model reaction with caprylic acid and butanol that was catalyzed by lipase from Mucor miehei in alkanes or arenes was employed to investigate the nonthermal effect in nonaqueous enzymatic esterification. With the comparison of the esterification carried by conventional heating and consecutive microwave irradiation, the positive nonthermal effect on the initial reaction rates was found substrate concentration-dependent and could be vanished ostensibly when the substrate concentration was over 2.