Hexabromocyclododecane in sediments from riverine, port, and coastal areas of Kaohsiung, Taiwan: levels, spatial distribution, and potential ecological risk.

The widespread use of hexabromocyclododecane (HBCD), a brominated flame retardant, is a major public health concern because of the toxic, persistent, and bioaccumulative nature of HBCD. However, there is limited information available regarding the distribution and transportation of HBCD in sediments across various environmental settings, spanning from riverine to marine environments in the Kaohsiung area of Taiwan. In this study, we comprehensively investigated the level and distribution of and potential ecological risk posed by HBCD in surface sediments in the Kaohsiung area of Taiwan. In sediment samples from stations on the Love River and Kaohsiung Port area, the concentrations of HBCD ranged from 10.6 to 320.1 µg/kg dry weight (dw) and nondetectable (n.d.) to 58.4 µg/kg dw, respectively. The concentrations of HBCD in sediment collected from the M1, M2, and M3 sites, located in the Cijin coastal area, were 896.2 µg/kg dw, 3.2 µg/kg dw ( 1. The M1 site had the highest risk level (RQ = 5.27). These data suggest that domestic sewage and industrial wastewater discharge pose a potential risk to marine environments. Consequently, timely measures to control HBCD-related risks are required. Our study offers insight into the environmental effects of HBCD contamination of sediment and provides valuable information that can be used to guide environmental policy and safety measures.

Capnellenes from Capnella imbricata: Deciphering Their Anti-Inflammatory-Associated Chemical Features.

Through our ongoing research on investigating new anti-inflammatory terpenoids derived from soft corals, seven capnellenes sourced from Capnella imbricata were discovered. Among these, three were previously unknown compounds named Δ9(12)-capnellene-6α,8ß-diol (1), Δ9(12)-capnellene-6α,8ß,10α-triol (2), and Δ9(12)-capnellene-2ß,8ß,10α-triol (3). The structures of all compounds were determined by spectroscopic analysis (IR, MS, 1D-, and 2D-NMR) and a comparison with the existing literature data. The compounds 1 and 2 were found to be the first-ever identified 6-hydroxy capnellenes. In the inflammation inhibitory assessments, compounds 1-7 were tested for their in vitro activities against inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expressions in LPS-induced RAW264.7 cells. Capnellenes 2 and 5 demonstrated significant reductions in iNOS levels (27.73% and 47.61%) at a concentration of 10 µM. Additionally, capnellenes 1, 5, and 7 (at 10 µM) exhibited statistically significant inhibitions (ranging from 7.64% to 12.57%) against COX-2 protein expressions. Our findings indicated that the oxygen-bearing functionalities at C-8 and C-10 play critical roles in inhibiting iNOS protein induction, which can promote inflammation in LPS-induced RAW264.7 cells. Furthermore, a principal component analysis tool, the chemical global positioning system for natural products (ChemGPS-NP), was applied to confirm these capnellane-based sesquiterpenes as promising candidates for future anti-inflammatory agents targeting iNOS-related targets.

Norsesquiterpenoids from the octocoral Paralemnalia thyrsoides (Ehrenberg 1834).

Three norsesquiterpenoids, pathyspirolactones A (1) and B (2), and napalilactone (3), featuring a γ-spirolactone moiety, were isolated from the cultured octocoral Paralemnalia thyrsoides. The structures of 1-3 were determined by analyzing spectroscopic data, DP4+ computation, specific optical rotation, and X-ray diffraction. In addition, we explored the absolute configurations of pathyspirolactone A (1) and its conformation of the cyclohexane ring to resolve the stereochemical confusion of those of norsesquiterpenoid compounds. Furthermore, we proved that pathyspirolactone B (2) was the first bromine-containing norsesquiterpenoid reported from octocorals.

Distribution patterns and transportation behavior of alkylphenol polyethoxylate degradation metabolites among river, port area, and coastal water bodies of Kaohsiung City, Taiwan.

In this study, we conducted a comprehensive study of the distribution, transportation behavior and potential ecological risk of alkylphenol polyethoxylates (APnEOs) in the aquatic environments of Kaohsiung City, Taiwan because little information is available regarding the fate of APnEOs in the water bodies of a total environment. At Love River, APnEOs concentrations were much higher at upstream of interception stations L15 (27.33 ± 1.22 µg/L) and L16 (6.31 ± 0.14 µg/L) than at downstream of interception stations L1-L14 (0.69-2.54 µg/L). Additionally, the average ethoxy (EO) chain lengths of APnEOs at L15 and L16 were longer than at L1-L14. These observations were attributed to the sluice between L14 and L15 that intercepts and accumulates untreated sewage from upstream areas and to the infrastructure of the sewage system that prevents domestic sewage from flowing downstream in the river and to the Kaohsiung Port Area. At Kaohsiung Port Area, APnEO concentrations ranging from 0.63 to 6.50 µg/L were measured. The concentration range and average EO chain length of these APnEOs were similar to those of the downstream stretch of the river, which was attributed to the mixing efficiency of the Kaohsiung Port Area and Love River through tidal exchange. At Cijin Coastal Area, APnEO concentrations ranged from 0.14 to 18.77 µg/L. Notably, the APnEO concentration of surface waters was much higher than that of bottom waters. This observation was attributed to the sewage discharged from the ocean outfall buoying up to the surface instead of mixing with surrounding bottom waters. In potential ecological risk, 19 of 39 sampling points exceeded toxic equivalency of 1 µg/L, and approximately 48.7% of the sampling points would exceed the threshold. The result provides insight into the environmental implications of APnEOs contamination in aquatic environments and useful information for environmental policy and ecological risk assessments.

Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758).

Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2ß,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC50 values of 11.22 and 23.53 µM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC50 value of 7.63 µM.

Natural Product Chemistry of Gorgonian Corals of Genus Junceella⁻Part III.

The structures, names, bioactivities, and references of 82 natural products, including 48 new metabolites, purified from the gorgonian corals belonging to the genus Junceella are described in this review. All compounds mentioned in this review were obtained from Junceella fragilis, Junceella gemmacea, Junceella juncea, and Junceella sp., collected from tropical Indo-Pacific Ocean. Some of these compounds exhibited potential biomedical activities.

Natural Caryophyllane Sesquiterpenoids from Rumphella antipathies.

Two new natural caryophyllane-type sesquiterpenoids, 1 and 2, were isolated from the gorgonian coral Rumphella antipathies. Standard spectroscopic techniques were used to determine the structures of caryophyllanes 1 and 2.

Rumphellaoic acid A, a novel sesquiterpenoid from the formosan gorgonian coral Rumphella antipathies.

A novel sesquiterpenoid, rumphellaoic acid A (1), was isolated from the gorgonian coral Rumphella antipathies, and was found to possess a carbon skeleton that was obtained for the first time from a natural sources. The structure of 1 was elucidated by spectroscopic methods and this compound and was found to exert a moderate inhibitory effect on the release of elastase by human neutrophils.

Rumphellols A and B, new caryophyllene sesquiterpenoids from a Formosan gorgonian coral, Rumphella antipathies.

Two new marine-derived caryophyllene-type sesquiterpenoids, rumphellols A and B (1 and 2), were obtained from the gorgonian coral, Rumphella antipathies, collected off the waters of Taiwan. Although caryophyllene-type sesquiterpenes are rarely found in marine organisms, compounds of this type could be principal components of R. antipathies. The structures of new Compounds 1 and 2 were determined by analysis of their spectroscopic data, including 1D and 2D NMR experiments. Caryophyllene 1 and 2 were evaluated in terms of their anti-inflammatory activity by examining their inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.

Rumphellaones B and C, new 4,5-seco-caryophyllane sesquiterpenoids from Rumphellan antipathies.

Two new 4,5-seco-caryophyllane sesquiterpenoids, rumphellaones B (1) and C (2), which were found to possess unprecedented γ-lactone moieties, were obtained from the gorgonian coral Rumphella antipathies. The structures of 1 and 2 were elucidated by spectroscopic methods and compound 2 was found to display modest inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils at a concentration of 10 µg/mL.

Natural clovanes from the gorgonian coral Rumphella antipathies.

Three natural clovane-related sesquiterpenoids, 2beta-acetoxyclovan-9alpha-ol (1), 9alpha-acetoxyclovan-2beta-ol (2) and clovan-2beta,9beta-diol (3), were isolated from the gorgonian coral Rumphella antipathies. The structures of clovanes 1-3 were elucidated by spectroscopic methods and by comparison of the spectral data with those of known clovane analogues. This is the first time that clovanes 1-3 have been isolated from a natural source. Clovanes 1 and 2 displayed inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.

Echinohalimane A, a bioactive halimane-type diterpenoid from a Formosan gorgonian Echinomuricea sp. (Plexauridae).

A new halimane-type diterpenoid, echinohalimane A (1), was isolated from a gorgonian, identified as Echinomuricea sp. The structure of 1 was determined by spectroscopic methods and this compound was found to exhibit cytotoxicity toward various tumor cells and display an inhibitory effect on the release of elastase by human neutrophils. Echinohalimane A (1) is the first halimane analogue from the marine organisms belonging to phylum Cnidaria.

Echinoclerodane A: a new bioactive clerodane-type diterpenoid from a gorgonian coral Echinomuricea sp.

A new clerodane-type diterpenoid, echinoclerodane A (1), was isolated from a Formosan gorgonian coral Echinomuricea sp. The structure of 1 was elucidated by spectroscopic methods. Echinoclerodane A (1) is the first clerodane-type compound obtained from the marine organisms belonging to the phylum Cnidaria. Echinoclerodane A (1) exhibited moderate cytotoxicity toward MOLT-4, HL-60, DLD-1 and LoVo tumor cells and inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

Bioactive compounds from a gorgonian coral Echinomuricea sp. (Plexauridae).

A new labdane-type diterpenoid, echinolabdane A (1), and a new sterol, 6-epi-yonarasterol B (2), were isolated from a gorgonian coral identified as Echinomuricea sp. The structures of metabolites 1 and 2 were elucidated by spectroscopic methods. Echinolabdane A (1) possesses a novel tetracyclic skeleton with an oxepane ring jointed to an α,ß-unsaturated-γ-lactone ring by a hemiketal moiety, and this compound is the first labdane-type diterpenoid to be obtained from marine organisms belonging to the phylum Cnidaria. 6-epi-Yonarasterol B (2) is the first steroid derivative to be isolated from gorgonian coral belonging to the genus Echinomuricea, and this compound displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.