New 8-Hydroxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae).
ABSTRACT: Three new 8-hydroxybriaranes-fragilides R-T (1-3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1-3 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8?-hydroxy and 17?-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.
Project description:Two new briarane metabolites—fragilides K (<b>1</b>) and L (<b>2</b>)—along with five known analogues—gemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (<b>3</b>?<b>7</b>)—were extracted and purified from <i>Junceella fragilis</i>, a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes <b>1</b> and <b>2</b> were determined and the cyclohexane rings in <b>1</b> and <b><i>2</i></b> were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes <b>2</b>, <b>3</b>, and <b>6</b> inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes <b>3</b> and <b>7</b> suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells.
Project description:Two new 11,20-epoxybriaranes, fragilides P (<b>1</b>) and Q (<b>2</b>), as well as two known analogues, robustolide F (<b>3</b>) and juncin Z (<b>4</b>), were obtained from the gorgonian coral <i>Junceella fragilis</i>. The structures, including the absolute configurations of briaranes <b>1</b> and <b>2</b>, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane <b>4</b> decreased the generation of superoxide anions by human neutrophils. The propionate group in <b>1</b> is rarely found.
Project description:Gorgonian corals are slowly declining due to human interaction and environmental impacts. Cryopreservation of gorgonian corals is an ex-situ method of conservation, ensuring future reproduction. The present study assessed the vitrification properties of cryoprotectant (CPT) mixtures using the cryotop, cryoloop and open pulled straw (OPS) cryopereservation methods prior to experimentation on gorgonian (Junceella juncea) oocytes. Investigations of the equilibration and vitrification solutions' (ES and VS) effect on oocytes throughout different incubation periods were conducted. The cryotop method was found to be the most successful in ensuring vitrification. The most favourable VS was composed of propylene glycol (PG), ethylene glycol (EG) and methanol with concentrations of 3.5 M, 1.5 M and 2 M respectively. Experiments were performed using the cryotop method to cryopreserve Junceella juncea oocytes using VS2, the solution had the least impact on oocytes at 5°C rather than at 26°C. The success of the vitrification procedures was determined by adenosine triphosphate (ATP) levels in cooled-thaw oocytes and the highest viability obtained from the present study was 76.6 ± 6.2%. This study provides information regarding gorgonian corals' tolerance and viability throughout vitrification to further advance the vitrification protocol on whip corals.
Project description:Two 11,20-epoxybriaranes, including a known compound, juncenolide K (<b>1</b>), as well as a new metabolite, fragilide X (<b>2</b>), have been isolated from gorgonian <i>Junceella fragilis</i> collected off the waters of Taiwan. The absolute configuration of juncenolide K (<b>1</b>) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane <b>2</b> was established on the basis of spectroscopic analysis and compared with that of model compound <b>1</b>. One aspect of the stereochemistry of the known compound <b>1</b> was revised. Briarane <b>2</b> was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.
Project description:Four new 8-hydroxybriarane diterpenoids, frajunolides L-O (1-4), were isolated from the Taiwanese gorgonian Junceella fragilis. The structures of compounds 1-4 were elucidated based on spectroscopic analysis, especially 2D NMR ((1)H-(1)H COSY, HSQC, HMBC and NOESY) and HRMS. Compounds 1 and 4 showed weak anti-inflammatory activity as tested by superoxide anion generation and elastase release by human neutrophil in response to fMLP/CB. Compound 3 showed selective inhibition on elastase release in vitro.
Project description:Four new 8-hydroxybriarane diterpenoids, frajunolides P-S (1-4), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 contains an unusual pivaloyloxy group at C-2, while 3 is a rare compound having a chlorine atom on the olefinic carbon (C-6). The structures of the isolated compounds were established by extensive spectroscopic analysis, including 1D- and 2D-NMR, as well as HRMS data. Compound 1 was further confirmed by X-ray crystallographic analysis. In the anti-inflammatory test, compounds 1 and 2 exhibited moderate inhibition on superoxide anion generation and elastase release by human neutrophils in response to formylmethionylleucyl-phenylalanine/dihydrocytochalasin B (fMLP/CB).
Project description:Three new 11,20-epoxybriaranes-fragilides U-W (<b>1</b>-<b>3</b>), as well as two known metabolites, junceellonoid D (<b>4</b>) and junceellin (<b>5</b>), were obtained from the octocoral <i>Junceella fragilis</i>. The structures of briaranes <b>1</b>-<b>3</b> were elucidated by spectroscopic methods and briaranes <b>3</b> and <b>5</b> displayed inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW264.7.
Project description:Two new briarane diterpenoids briareolate esters J (1) and K (2) were isolated from the methanolic extract of the octocoral Briareum asbestinum collected off the coast of Boca Raton, Florida. The structures of briaranes 1 and 2 were elucidated by interpretation of spectroscopic data. Briareolate ester K (2) showed weak growth inhibition activity against human embryonic stem cells (BG02).
Project description:Seven new briarane diterpenoids, gemmacolides AS-AY (1-7), were isolated together with ten known analogues (8-17) from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data and comparison with reported data. The absolute configuration of compounds was determined based on electronic circular dichroism (ECD) experiments and genetic correlations as well. Compounds 15 and 16 were reported for the first time for the gorgonian. In the preliminary in vitro bioassays, compound 5 showed potential growth inhibitory activity against MG63 cells.
Project description:The four new briarane diterpenoids 2-butyryloxybriarane B-3 (2), 9-acetylbriarenolide S (3), briarenolide W (4), and 12-isobriarenolide P (5), along with briarane B-3 (1) and the five known diterpenes 6-10 were isolated from the gorgonian coral Briareum asbestinum collected from the Mexican Caribbean Sea. The structures were elucidated by 1D and 2D NMR and MS measurements. Since the structure of briarane B-3 (1) was only suggested and published without any spectroscopic support, it was herein confirmed, and the supporting data are now provided. In addition, 1 provided the opportunity to explore the sensitivity of vibrational circular dichroism (VCD) to determine the configuration of a single stereogenic center in the presence of eight other stereogenic centers in a molecule possessing a highly flexible ten-member ring. A single-crystal X-ray diffraction study, in which the Flack and Hooft parameters of 1 were determined, further confirmed that briarane B-3 is (1S,2S,6S,7R,8R,9S,10S,11R,17R)-1. This paper reports for first time the use of VCD in briarane diterpenes and with the presence of chlorine atoms. Biological evaluation of seven isolated compounds evidenced a moderate anti-inflammatory activity for compounds 6 and 9 but it did not show any cytotoxic, antiviral, antibacterial, and topoisomerase inhibitory activity.