Carneusones A-F, Benzophenone Derivatives from Sponge-Derived Fungus Aspergillus carneus GXIMD00543.

Six benzophenone derivatives, carneusones A-F (1-6), along with seven known compounds (7-13) were isolated from a strain of sponge-derived marine fungus Aspergillus carneus GXIMD00543. Their chemical structures were elucidated by detailed spectroscopic data and quantum chemical calculations. Compounds 5, 6, and 8 exhibited moderate anti-inflammatory activity on NO secretion using lipopolysaccharide (LPS)-induced RAW 264.7 cells with EC50 values of 34.6 ± 0.9, 20.2 ± 1.8, and 26.8 ± 1.7 µM, while 11 showed potent effect with an EC50 value of 2.9 ± 0.1 µM.

Secofumitremorgins C and D, a pair of atropisomers from saltern-derived fungus Aspergillus fumigatus GXIMD00544.

A pair of atropisomers secofumitremorgins C (1a) and D (1b), together with fifteen known alkaloids (2-16), were isolated from a saltern-derived fungus Aspergillus fumigatus GXIMD00544. The structures of atropisomers 1a and 1b were elucidated by the detailed spectroscopic data, chemical reaction and quantum chemical calculations. Compounds 1 and 8 displayed antifungal spore germination effects against plant pathogenic fungus associated with sugarcane Fusarium sp. with inhibitory rates of 53% and 77% at the concentration of 100 µM, repectively. Atropisomers 1 also exhibited antifouling potential against Balanus amphitrite larval settlement with an inhibitory rate of 96% at the concentration of 100 µM.

Sonneradon A Extends Lifespan of Caenorhabditis elegans by Modulating Mitochondrial and IIS Signaling Pathways.

Aging is related to the lowered overall functioning and increased risk for various age-related diseases in humans. Sonneradon A (SDA), a new compound first extracted from the edible fruits of mangrove Sonneratia apetala, showed remarkable antiaging activity. However, the role of SDA in antiaging remains unclear. In this article, we studied the function of SDA in antiaging by using the animal model Caenorhabditis elegans. Results showed that SDA inhibited production of reactive oxygen species (ROS) by 53%, and reduced the accumulation of aging markers such as lipids and lipofuscins. Moreover, SDA also enhanced the innate immune response to Pseudomonas aeruginosa infection. Genetic analysis of a series of mutants showed that SDA extended the lifespan of the mutants of eat-2 and glp-1. Together, this effect may be related to the enhanced resistance to oxidative stress via mitochondrial and insulin/insulin-like growth factor-1 signaling (IIS) pathways. The results of this study provided new evidence for an antiaging effect of SDA in C. elegans, as well as insights into the implication of antiaging activity of SDA in higher organisms.

HPLC-DAD-Guided Isolation of Diversified Chaetoglobosins from the Coral-Associated Fungus Chaetomium globosum C2F17.

Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium globosum C2F17. Their structures were accomplished by extensive spectroscopic analysis combined with single-crystal X-ray crystallography and ECD calculations. Meanwhile, the structures and absolute configurations of the previously reported compounds 6, 12, and 13 were confirmed by single-crystal X-ray analysis for the first time. Chaetoglobosins E (6) and Fex (11) showed significant cytotoxicity against a panel of cancer cell lines, K562, A549, Huh7, H1975, MCF-7, U937, BGC823, HL60, Hela, and MOLT-4, with the IC50 values ranging from 1.4 µM to 9.2 µM.

Marinoid J, a phenylglycoside from Avicennia marina fruit, ameliorates cognitive impairment in rat vascular dementia: a quantitative iTRAQ proteomic study.

CONTEXT: Fruit of Avicennia marina (Forsk.) Vierh. (Acanthaceae) is used as a Chinese herb. Studies have found that it contains marinoid J, a novel phenylethanoid glycoside (PG) compound, but its neuroprotective functions are largely unknown. OBJECTIVE: This study evaluated the effects of marinoid J on vascular dementia (VD) and determined its potential mechanisms of action. MATERIALS AND METHODS: The VD model was established by the ligation of the bilateral common carotid artery in Sprague-Dawley rats, who received daily intragastrically administration of saline, marinoid J (125 or 500 mg/kg body weight/d), or oxiracetam (250 mg/kg body weight/d) for 14 days (20 rats in each group). The Morris water maze (MWM) was used to evaluate cognitive performance. The hippocampus was subjected to histological and proteomic analyses. RESULTS: Marinoid J shortened the escape latency of VD rats (31.07 ± 3.74 s, p < 0.05). It also decreased malondialdehyde (MDA) (27.53%) and nitric oxide (NO) (20.41%) while increasing superoxide dismutase (SOD) (11.26%) and glutathione peroxidase (GSH-Px) (20.38%) content in hippocampus tissues. Proteomic analysis revealed 45 differentially expressed proteins (DEPs) in marinoid J-treated VD rats, which included angiotensin-converting enzyme (ACE), keratin 18 (KRT18), cluster of differentiation 34 (CD34), and synaptotagmin II (SYT2). CONCLUSIONS: Marinoid J played a role in protecting hippocampal neurons by regulating a set of proteins that influence oxidative stress and apoptosis, this effect may thereby alleviate the symptoms of VD rats. Thus, pharmacological manipulation of marinoid J may offer a novel opportunity for VD treatment.

Nocardioides sonneratiae sp. nov., an endophytic actinomycete isolated from a branch of Sonneratia apetala.

A Gram-staining-positive, aerobic non-spore-forming and short-rod-shaped endophytic actinomycete was isolated from a branch of Sonneratia apetala, designated strain BGMRC0092T and investigated in detail data to determine its taxonomic position. On the basis of the 16S rRNA gene sequence analysis, the results of the phylogenetic analyses indicated that BGMRC0092T was most closely related to Nocardioides alpinus Cr7-14T (96.9 %), Nocardioides oleivorans DSM16090T (96.4 %) and Nocardiodes exalbidus RC825T (96.3 %). The predominant cellular fatty acids of BGMRC0092T were iso-C16 : 0 and C18 : 1ω8c. The major menaquinone was MK-8(H4). The diagnostic diamino acid in the cell-wall peptidoglycan was ll-2,6-diaminopimelic acid. The predominant cell-wall sugars were composed of galactose, mannose, rhamnose and xylose. The polar lipid pattern contained diphosphatidylglycerol, phosphatidylglycerol, phosphatidylcholine, one unknown phospholipid and three unknown polar lipids. The DNA G+C content was 69.3 mol%. On the basis of phenotypic and chemotaxonomic characteristics and the results of phylogenetic analysis, BGMRC0092T represents a novel species of the genus Nocardioides, for which the name Nocardioides sonneratiae sp. nov. is proposed. The type strain is Nocardioides sonneratiae BGMRC0092T (=KCTC 39565T=NBRC 110251 T=DSM 100390T).

Nocardioides kandeliae sp. nov., an endophytic actinomycete isolated from leaves of Kandelia candel.

A Gram-stain-positive, aerobic, non-spore-forming, atrichous and short rod-shaped endophytic actinomycete, designated strain BGMRC 2075T, was isolated from the leaves of Kandelia candel, and was subjected to polyphasic characterization to unravel its taxonomic position. Phylogenetic analyses based on 16S rRNA gene sequences indicated that strain BGMRC 2075T belongs to the genus Nocardioides ,showing the highest 16S rRNA gene sequence similarity to Nocardioides aestuarii JC2056T (96.1 %), Nocardioides agariphilus MSL-28T (95.1 %) andNocardioides islandiensis MSL-26T (95.1 %). The predominant cellular fatty acids of strain BGMRC 2075T were iso-C16 : 0, C17 : 1ω8c and C17 : 0. The major menaquinone was MK-8(H4). The diagnostic diamino acid in the cell-wall peptidoglycan was ll-2,6-diaminopimelic acid. The predominant cell-wall sugars were composed of ribose and glucose. The polar lipid pattern contained diphosphatidylglycerol, phosphatidylglycerol, phosphatidylmethylethanolamine, phosphatidylcholine, five unknown phospholipids, one phospholipid of unknown structure containing glucosamine, and an unknown polar lipid. The DNA G+C content was 70.8 mol%. All these data support the allocation of the novel strain to the genus Nocardioides. The results of physiological and biochemical characterization allow the phenotypic differentiation of strain BGMRC 2075T from N. aestuarii JC2056T, N. agariphilus MSL-28T and N. islandiensis MSL-26T. Strain BGMRC 2075T represents a novel species of the genus Nocardioides, for which we propose the name Nocardioides kandeliae sp. nov. The type strain is BGMRC 2075T (=KCTC 39886T=DSM 104480T).

Four New Cyclohexylideneacetonitrile Derivatives from the Hypocotyl of Mangrove (Bruguiera gymnorrhiza).

Four new cyclohexylideneacetonitrile derivatives 1-4, named menisdaurins B-E, as well as three known cyclohexylideneacetonitrile derivatives--menisdaurin (5), coclauril (6), and menisdaurilide (7)--were isolated from the hypocotyl of a mangrove (Bruguiera gymnorrhiza). The structures of the isolates were elucidated on the basis of extensive spectroscopic analysis. Compounds 1-7 showed anti-Hepatitis B virus (HBV) activities, with EC50 values ranging from 5.1 ± 0.2 µg/mL to 87.7 ± 5.8 µg/mL.

[Study on Chemical Constituents from Hypocotyls of Mangrove Bruguiera gymnorrhiza].

OBJECTIVE: To study the chemical constituents from the hypocotyls of mangrove Bruguiera gymnorrhiza. METHODS: The chemical constituents were isolated and purified by recrystallization, silica gel column chromatography and semi-preparative HPLC. Their structures were identified by spectroscopic analysis and comparison with literatures. RESULTS: Seven compounds were isolated and their structures were identified as 3-ß-(Z)-coumaroyllupeol (1), dioslupecin (2), cholesterol (3), menisdaurillide (4), aquilegiolide (5) vomifoliol (6) and roseoside II (7). CONCLUSION: Compounds 1,2 and 4 - 7 are isolated from this plant for the first time.

Marine nucleosides: structure, bioactivity, synthesis and biosynthesis.

Nucleosides are glycosylamines that structurally form part of nucleotide molecules, the building block of DNA and RNA. Both nucleosides and nucleotides are vital components of all living cells and involved in several key biological processes. Some of these nucleosides have been obtained from a variety of marine resources. Because of the biological importance of these compounds, this review covers 68 marine originated nucleosides and their synthetic analogs published up to June 2014. The review will focus on the structures, bioactivities, synthesis and biosynthetic processes of these compounds.

An update on 2,5-diketopiperazines from marine organisms.

2,5-Diketopiperazines (2,5-DKPs) are an important category of structurally diverse cyclic dipeptides with prominent biological properties. These 2,5-DKPs have been obtained from a variety of natural resources, including marine organisms. Because of the increasing numbers and biological importance of these compounds, this review covers 90 marine originated 2,5-DKPs that were reported from 2009 to the first half-year of 2014. The review will focus on the structure characterizations, biological properties and proposed biosynthetic processes of these compounds.

Four new Jacaranone analogs from the fruits of a Beibu Gulf mangrove Avicennia marina.

Four new jacaranone analogs, marinoids F-I (1-4), were isolated from the fruits of a Beibu Gulf mangrove Avicennia marina. The structures were elucidated based on analysis of spectroscopic data. Marinoids F and G are shown to be diastereoisomers of chlorocornoside, a new halogen containing marine secondary metabolite. The antioxidant activity of the isolates was evaluated using a cellular antioxidant assay, and 4 showed good antioxidant activity (EC50 = 26 µM).

New antioxidative secondary metabolites from the fruits of a Beibu Gulf mangrove, Avicennia marina.

Further chemical investigation of the fruits of the mangrove, Avicennia marina, afforded three new phenylethyl glycosides, marinoids J-L (1-3), and a new cinnamoyl glycoside, marinoid M (4). The structures of isolates were elucidated on the basis of extensive spectroscopic analysis and by comparison of the data with those of related secondary metabolites. The antioxidant activity of the isolates was evaluated using the cellular antioxidant assay (CAA), and compounds 1-4 showed antioxidant activities, with EC50 values ranging from 23.0 ± 0.71 µM to 247.8 ± 2.47 µM.

Mauritone A, a new polyketide from a fungal-bacterial symbiont Aspergillus spelaeus GXIMD 04541/Sphingomonas echinoides GXIMD 04532.

A new polyketide, mauritone A (1) with six known polyketides curvulone B (2), curvularin (3), 12-oxocurvularin (4), (10E,15S)-10,11-dehydrocurvularin (5), (11R,15S)-11-hydroxycurvularin (6), and (11S,15S)-11-hydroxycurvularin (7) were isolated from the fungal-bacterial symbiont Aspergillus spelaeus GXIMD 04541/Sphingomonas echinoides GXIMD 04532 derived from Mauritia arabica. Their structures were elucidated by extensive spectral analysis. All compounds (1-7) were evaluated for their anti-inflammatory effects. The inhibitory effects of 4, 5, and 7 on nitric oxide (NO) production were found to be significant, with IC50 values of 5.5 ± 0.26, 2.0 ± 0.31, and 8.3 ± 0.62 µM, respectively, surpassing that of the positive control quercetin (10.6 ± 0.64 µM). Compounds 3 and 6 exhibited moderate inhibition of NO, with IC50 values of 18.6 ± 0.53 and 12.7 ± 0.45 µM, respectively.

Austin-Type Meroterpenoids from Fungi Reported in the Last Five Decades: A Review.

Austin was first isolated as a novel polyisoprenoid mycotoxin from Aspergillus ustus in 1976. Subsequently, some new austin-type meroterpenoids (ATMTs) have been continually found. This review attempts to give a comprehensive summary of progress on the isolation, chemical structural features, biological activities, and fungal biodiversity of 104 novel ATMTs from 5 genera of terrestrial- and marine-derived fungi reported from October 1976 to January 2023. The genera of Penicillium and Aspergillus are the two dominant producers, producing 63.5% and 30.8% of ATMTs, respectively. Moreover, about 26.9% of ATMTs display various pronounced bioactivities, including insecticidal, anti-inflammatory, cytotoxicity, antibacterial, and PTP1B inhibitory activities. The chemical diversity and potential activities of these novel fungal ATMTs are reviewed for a better understanding, and a relevant summary focusing on the source fungi and their taxonomy is provided to shed light on the future development and research of austin-type meroterpenoids.

Sonneralignan A, a new lignan from the fruit of mangrove Sonneratia apetala.

A new lignan, sonneralignan A (1), along with two known lignan compounds, (+)-lariciresinol-9-O-ß-D-glucopyranoside (2) and (-)isolariciresinol-9-O-ß-D-glucopyranoside (3) were isolated from the n-butanol extract of the mangrove Sonneratia apetala fruit. The structures of the compounds were elucidated on the basis of extensive spectral analysis. The evaluation of activity showed that compound 1 exhibited significant anti-aging activity, which extended the mean lifespan of Caenorhabditis elegans by up to 19.13% (p < 0.05) and 55.29% (p < 0.01) under normal and heat stress cultivation conditions, respectively. Molecular docking studies showed that compound 1 was bound to the DNA binding domain of DAF-16 and promoted the conformation of DAF-16, thus strengthening the interaction between the DAF-16 and related DNA. TRP-252, SER-250 and SER-249 of the binding region might be the key amino residues during the interaction.

Penicixanthene E, a new xanthene isolated from a mangrove-derived fungus Penicillium sp.

One new xanthene derivative, named penicixanthene E (1), together with one known compound 2, was isolated from the EtOAc extract of the endophytic fungus Penicillium sp. GXIMD 03101, which was identified from the mangrove Acanthus ilicifolius L. collected in the South China Sea. The structure of 1 was elucidated by 1D and 2D NMR spectral interpretation and HREISMS data. The absolute configurations of C-9 and C-11 in 1 were proposed based on electronic circular dichroism (ECD), but the configuration at C-3 in 1 was unassigned. Compound 1 represents a xanthene derivative that was first reported, in which carbon-carbon double bond has been reduced. The cytotoxic activities of all compounds were evaluated, the result showed that compound 1 has weak activity against pancreatic cancer SW1990.

Alkaloids and sesquiterpenes from the South China Sea gorgonian Echinogorgia pseudossapo.

Five zoanthoxanthin alkaloids (1-5) and four sesquiterpenes (6-9) were isolated from the South China Sea gorgonian Echinogorgia pseudossapo. Their structures were determined on the bases of extensive spectroscopic analyses, including 1D and 2D NMR data. Among them, pseudozoanthoxanthins III and IV (1-2), 8-hydroxy-6ß-methoxy-14- oxooplop-6,12-olide (6) and 3ß-methoxyguaian-10(14)-en-2ß-ol (7) were new, 1 and 3 showed mild anti-HSV-1 activity, and 7 showed significant antilarval activity towards Balanus amphitrite larvae.

Two new benzophenones isolated from a mangrove-derived fungus Penicillium sp.

One new benzophenone derivative, named penibenzophenone C (1), and a new benzophenone natural product, neamed penibenzophenone D (2), together with two known compounds (3, 4) were isolated from the EtOAc extract of the endophytic fungus Penicillium sp. isolated from the mangrove Acanthus ilicifolius L. collected in the South China Sea. The structures of 1-4 were elucidated by extensive NMR spectral interpretation and MS data. The new compounds 1 and 2 showed moderate antibacterial activities against methicillin-resistant Staphylococcus aureus with the MIC values of 3.12 and 6.25 µg ml-1, respectively.