Two New Cerebroside Metabolites from the Marine Fungus Hortaea werneckii.

Two new cerebroside metabolites were isolated from the fermented sponge-derived fungus extract of Hortaea werneckii. They were hortacerebroside A (1) ((2R,3E)-N-[(2S,3R,4E,8E)-1-(ß-D-glucopyranosyloxy)-3-hydroxy-9-methylhenicosa-4,8-dien-2-yl]-2-hydroxypentadec-3-enamide) and hortacerebroside B (2) ((2R)-N-[(2S,3R,4E,8E)-1-(ß-D-glucopyranosyloxy)-3-hydroxy-9-methylhenicosa-4,8-dien-2-yl]-2-hydroxypentadecanamide). Their structures were elucidated by spectroscopic analysis and by comparison of the spectroscopic data with those of related cerebroside analogs. These two compounds showed significant inhibitory effect on NO produced by lipopolysaccharide (LPS) stimulated RAW 264.7 macrophages. The IC50 values of hortacerebroside A (1) and hortacerebroside B (2) were 7 and 5 µM, respectively. These results suggested the potential application of these cerebrosides as drug leads targeting inflammatory-related disorders.

Natural Products from Octocorals of the Genus Dendronephthya (Family Nephtheidae).

In this review, 170 natural substances, including steroid, diterpenoid, sesquiterpenoid, peptide, prostaglandin, base, chlorolipid, bicyclolactone, amide, piperazine, polyketide, glycerol, benzoic acid, glycyrrhetyl amino acid, hexitol, pentanoic acid, aminoethyl ester, octadecanone, alkaloid, and a 53-kD allergenic component from octocorals belonging to genus Dendronephthya, were listed. Some of these compounds displayed potential bioactivities.

Study on Chemical Profile and Neuroprotective Activity of Myrica rubra Leaf Extract.

The chemical profile of Myrica rubra (a native species in China) leaf extract was investigated by UPLC-PDA-HRMS, and the neuroprotective activity of two characteristic constituents, myricanol and myricetrin, was evaluated with N2a cells using H2O2-inducedoxidative challenge through a series of methods, e.g., MTT assay, ROS assay and [Ca2+]i assay. Among the 188 constituents detected in the extract of Myrica rubra leaf, 116 were identified definitely or tentatively by the comprehensive utilization of precise molecular weight and abundant multistage fragmentation information obtained by quadrupole orbitrap mass spectrometry. In addition, 14 potential new compounds were reported for the first time. This work established an example for the research of microconstituents in a complex analyte and revealed that suppression of H2O2-induced cytotoxicity in N2a cells was achieved by the pretreatment with myricanol. The evidence suggested myricanol may potentially serve as a remedy for prevention and therapy of neurodegenerative diseases induced by oxidative stress.

Briarane diterpenoids isolated from gorgonian corals between 2011 and 2013.

The structures, names, bioactivities and references of 138 briarane-type diterpenoids, including 87 new compounds, are summarized in this review. All the briarane-type compounds mentioned in this review article were obtained from gorgonian corals including the genus Briareum, Dichotella, Junceella and Verrucella. Some of these compounds showed potential bioactivities.

Three new clerodane diterpenes from Polyalthia longifolia var. pendula.

Three new clerodane diterpenes, (4→2)-abeo-cleroda-2,13E-dien-2,14-dioic acid (1), (4→2)-abeo-2,13-diformyl-cleroda-2,13E-dien-14-oic acid (2), and 16(R&S)- methoxycleroda-4(18),13-dien-15,16-olide (3), were isolated from the unripe fruit of Polyalthia longifolia var. pendula (Annonaceae) together with five known compounds (4-8). The structures of all isolates were determined by spectroscopic analysis. The anti-inflammatory activity of the isolates was evaluated by testing their inhibitory effect on NO production in LPS-stimulated RAW 264.7 macrophages. Among the isolated compounds, 16-hydroxycleroda-3,13-dien-15,16-olide (6) and 16-oxocleroda-3,13-dien-15-oic acid (7) showed promising NO inhibitory activity at 10 µg/mL, with 81.1% and 86.3%, inhibition, respectively.

Optimization of Fermentation Process for New Anti-Inflammatory Glycosylceramide Metabolite from Aspergillus sp.

A novel ceramide compound, named Aspercerebroside A (AcA), was successfully isolated from the ethyl acetate layer of the marine symbiotic fungus Aspergillus sp. AcA exhibited notable anti-inflammatory activity by effectively inhibiting the production of nitric oxide (NO) in RAW 264.7 cells at concentrations of 30 µg/mL and 40 µg/mL, offering a promising avenue for the treatment of inflammatory diseases. To optimize the yield of glycosylceramide (AcA), a series of techniques, including single-factor experiments, orthogonal experiments, and response surface optimization, were systematically employed to fine-tune the composition of the fermentation medium. Initially, the optimal carbon source (sucrose), nitrogen source (yeast extract powder), and the most suitable medium salinity (14 ppt) were identified through single-factor experiments. Subsequently, orthogonal experiments, employing an orthogonal table for planning and analyzing multifactor experiments, were conducted. Finally, a mathematical model, established using a Box-Behnken design, comprehensively analyzed the interactions between the various factors to determine the optimal composition of the fermentation medium. According to the model's prediction, when the sucrose concentration was set at 37.47 g/L, yeast extract powder concentration at 19.66 g/L, and medium salinity at 13.31 ppt, the predicted concentration of glycosylceramide was 171.084 µg/mL. The experimental results confirmed the model's accuracy, with the actual average concentration of glycosylceramide under these conditions measured at 171.670 µg/mL, aligning closely with the predicted value.

Identification of bioactive compounds and inhibitory effects of TNF-α and COX-2 in the extract from cultured three-spot seahorse (H. trimaculatus).

Three-spot seahorse (Hippocampus trimaculatus) has been consumed as traditional Chinese medicine in Asian society. This study was designed to analyze the bioactive compounds of the solvent extracts from cultured three-spot seahorse by high pressure liquid chromatography coupled with electrospray ionization tandem mass spectrometry (HPLC-ESI/MS/MS). Subsequently, their biological activities were evaluated and confirmed by cell modes and Western blot analysis. Experimental results indicated that taurine and arginine were the primary bioactive compounds identified and quantified without pre- or post-column derivatization within 20 min retention time. The analytical method was established and validated with intraday/interday RSD from 0.25% to 3.34% and with recovery from 87.8% to 91.2%. As compared to other extracts, water layer extract (WLE) contained the most taurine and arginine contents of 6.807 and 0.437 mg/g (dry basis), respectively. In the meanwhile, WLE also showed anti-inflammatory activity on LPS-induced NO production and inhibited the protein expression of TNF-α and COX-2 by Western blot analysis with better cell viability.

Cembrane derivatives from the soft corals, Sinularia gaweli and Sinularia flexibilis.

A new norcembranoidal diterpene, 1-epi-sinulanorcembranolide A (1), and a new cembranoidal diterpene, flexibilin D (2), were isolated from the soft corals, Sinularia gaweli and Sinularia flexibilis, respectively. The structures of new metabolites 1 and 2 were elucidated by spectroscopic methods, and compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 proteins of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. In addition, S. flexibilis yielded a known cembrane, 5-dehydrosinulariolide (3); the structure, including its absolute stereochemistry, was further confirmed by single-crystal X-ray diffraction analysis.

Flexibilins A-C, new cembrane-type diterpenoids from the Formosan soft coral, Sinularia flexibilis.

Three new cembrane-type diterpenoids, flexibilins A-C (1-3), along with a known cembrane, (-)-sandensolide (4), were isolated from the soft coral, Sinularia flexibilis. The structures of cembranes 1-4 were elucidated by spectroscopic methods. The structure of 4, including its absolute stereochemistry, was further confirmed by single-crystal X-ray diffraction analysis. Cembrane 2 displayed a moderate inhibitory effect on the release of elastase by human neutrophils.

A new 5α,8α-Epidioxysterol from the soft coral Sinularia gaweli.

A new sterol, (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methyl-cholest-6,9(11)-dien-3ß-ol (1), and two known sterols, (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methylcholest-6-en-3ß-ol (2) and 24-methylenecholestane-1α,3ß,5α, 6ß,11α-pentol (3), were isolated from the soft coral Sinularia gaweli. The structure of sterol 1 was established by spectroscopic methods and by comparison of the spectral data with those of known analogues. The cytotoxicity of sterols 1-3 towards various tumor cells is reported.

Pseudoalteromone B: a novel 15C compound from a marine bacterium Pseudoalteromonas sp. CGH2XX.

A novel 15C compound, pseudoalteromone B (1), possessing a novel carbon skeleton, was obtained from a marine bacterium Pseudoalteromonas sp. CGH2XX. This bacterium was originally isolated from a cultured-type octocoral Lobophytum crassum, that was growing in cultivating tanks equipped with a flow-through sea water system. The structure of 1 was established by spectroscopic methods. Pseudoalteromone B (1) displayed a modestly inhibitory effect on the release of elastase by human neutrophils.

Natural product chemistry of gorgonian corals of the family Plexauridae distributed in the Indo-Pacific Ocean.

The structures, names, bioactivities and references of 105 natural products obtained from gorgonian corals belonging to the family Plexauridae with an Indo-Pacific distribution are described in this review. All compounds mentioned in this review were obtained from gorgonian corals belonging to the genera Astrogorgia, Bebryce, Echinomuricea, Euplexaura and Menella.

Briarenolides F and G, new briarane diterpenoids from a Briareum sp. octocoral.

Two new briarane diterpenoids, briarenolides, F (1) and G (2), were isolated from an octocoral identified as Briareum sp. The structures of briaranes 1 and 2 were established by spectroscopic methods and by comparison of the spectroscopic data with those of known briarane analogues. Briarenolide F was proven to be the first 6-hydroperoxybriarane derivative and this compound displayed a significant inhibitory effect on the generation of superoxide anion by human neutrophils.

New 6-hydroxyeunicellins from a soft coral Cladiella sp.

Two new 6-hydroxyeunicellin diterpenoids, cladieunicellin G (1) and 6-epi-cladieunicellin F (2), were isolated from an Indonesian octocoral Cladiella sp. The structures of eunicellins 1 and 2 were established by spectroscopic methods and 2 was found to be an epimer of the known eunicellin cladieunicellin F (3). Eunicellin 2 displayed inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

Discovery of new eunicellins from an Indonesian octocoral Cladiella sp.

Two new 11-hydroxyeunicellin diterpenoids, cladieunicellin F (1) and (-)-solenopodin C (2), were isolated from an Indonesian octocoral Cladiella sp. The structures of eunicellins 1 and 2 were established by spectroscopic methods, and eunicellin 2 was found to be an enantiomer of the known eunicellin solenopodin C (3). Eunicellin 2 displayed inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils. The previously reported structures of two eunicellin-based compounds, cladielloides A and B, are corrected in this study.

Cladieunicellins A-E, new eunicellins from an Indonesian soft coral Cladiella sp.

Five new eunicellin-type diterpenoids, cladieunicellins A-E (1-5), were isolated from an Indonesian soft coral identified as Cladiella sp. The structures of diterpenoids 1-5 were established using spectroscopic methods. Eunicellins 2 and 5 were found to be cytotoxic against DLD-1 and HL-60 tumor cells, respectively, and 3 displayed inhibitory effects against superoxide anion generation by human neutrophils.

(-)-Hydroxylindestrenolide, a new sesquiterpenoid from a gorgonian coral Menella sp. (Plexauridae).

(-)-Hydroxylindestrenolide (1), an enantiomer of the known sesquiterpenoid, (+)-hydroxylindestrenolide (2), was isolated from a gorgonian coral identified as Menella sp. The structure, including the relative stereochemistry of 1 was established by spectroscopic methods and by comparison the spectral and physical data with those of 2. Sesquiterpenoid 1 exhibited marginal cytotoxicity toward HL-60 and K562 leukemia tumor cells, and displayed a weak inhibitory effect on superoxide anion generation at a concentration of 10 µg/ml by human neutrophils.

Cladielloides A and B: new eunicellin-type diterpenoids from an Indonesian octocoral Cladiella sp.

Two new eunicellin-type diterpenoids, cladielloides A (1) and B (2), which were found to possess a 2-hydroxybutyroxy group in their structures, were isolated from an Indonesian octocoral identified as Cladiella sp. The structures of eunicellins 1 and 2 were elucidated by spectroscopic methods. Cladielloide B (2) exhibited moderate cytotoxicity toward CCRF-CEM tumor cells and this compound displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils.

Carijoside A, a bioactive sterol glycoside from an octocoral Carijoa sp. (Clavulariidae).

A new bioactive sterol glycoside, 3beta-O-(3',4'-di-O-acetyl-beta-D-arabinopyranosyl)-25xi-cholestane-3beta,5alpha,6beta,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside 1 was established by spectroscopic methods and by comparison with spectral data for the other known glycosides. Carijoside A (1) displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils and this compound exhibited moderate cytotoxicity toward DLD-1, P388D1, HL-60, and CCRF-CEM tumor cells.

Excavatoids O and P, new 12-hydroxybriaranes from the octocoral Briareum excavatum.

Two new 12-hydroxybriarane diterpenoids, designated as excavatoids O (1) and P (2), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1 and 2 were established on the basis of extensive spectral data analysis. Excavatoid P (2) is the first metabolite which possesses a 6ß -chlorine atom in briarane analogues.