Soft Coral Lobophytum Research Articles

Polyoxygenated Cembranoids from Soft Coral Lobophytum Crassum and Their Anti‐tumoral Activities

Main observation and conclusionFour new cembranoids, 6‐oxo‐cembrene‐A (1), lobocrassins G—H (2—3), and 14‐epi‐lobophytolide B (4), along with eight known related compounds (5—12), were isolated from the South China Sea soft coral Lobophytum crassum. Their structures were established by extensive spectroscopic analysis and by comparison of the spectral data with those reported in the literatures. The absolute stereochemistry of 14‐epi‐lobophytolide B (4) was established by time‐dependent density functional theory electronic circular dichroism (TDDFT‐ECD) calculations, whereas that of three known metabolites (6, 11 and 12) was also determined, for the first time, by using modified Mosher's method and/or X‐ray diffraction analyses. In bioassay, the cembranoids 6, 7 and 12 showed significant anti‐tumoral activity against A549, HT‐29, SNU‐398 and Capan‐1 tumor cell lines with IC50 values ranging from 1.5 to 7.4 μmol/L. A preliminary structure‐activity relationship was also discussed.

Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha soft coral Lobophytum sp

Seven new cembrane-type diterpenes, lobophytolins C–I (3–9), and one new prenylated-guiane-type diterpene, lobophytolin J (10), along with six known related ones (1, 2, 11–14), have been isolated from the soft coral Lobophytum sp. collected off the Xisha Island in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis and quantum mechanical (QM)-NMR methods. The absolute configuration of lobophytolin H (8) was determined by the application of the modified Mosher’s method and chemical transformation. Lobophytolin D (4) exhibited promising cytotoxicities in in vitro bioassays against HT-29, Capan-1, A549, and SNU-398 human cancer cell lines with IC50 values of 4.52, 6.62, 5.17, and 6.15 μM, respectively.

New Steroids from the South China Sea Soft Coral Lobophytum sp.

Two new steroids, (22R,23S)-3β-hydroxy-23-methyl-17,20-epoxyergost-5-en-22-yl acetate and (22R,23S)-5-hydroperoxy-23-methyl-5α-17,20-epoxyergost-6-ene-3β,22-diol, were isolated from the South China Sea soft coral Lobophytum sp., together with two related known ones. The structures of all compounds were elucidated by extensive spectroscopic analysis and by comparing their spectral data with those previously reported. The structure of (22R,23S)-3β-hydroxy-23-methyl-17,20-epoxyergost-5-en-22-yl acetate was further confirmed through chemical correlation. All the isolates were evaluated for the in vitro inhibitory activity against NF-κB, a potential target for the treatment of cancer, and (22R,23S)-5-hydroperoxy-23-methyl-5α-17,20-epoxyergost-6-ene-3β,22-diol exhibited moderate inhibition activity with IC50 value of 8.96 μg/mL.

Quantum Mechanical-NMR-Aided Configuration and Conformation of Two Unreported Macrocycles Isolated from the Soft Coral Lobophytum sp.: Energy Calculations versus Coupling Constants.

Two new macrocyclic cembranoids were isolated from the South China Sea soft coral Lobophytum sp. Quantum mechanical-nuclear magnetic resonance (QM-NMR) methods were decisive in their structural elucidation. Better performance in arriving at definitive structures was obtained by QM-NMR methods upon incorporation of 3JHH values. The validity of this approach also supported an alternative conformational proposal versus that obtained by X-ray crystallography.

Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium.

Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F–P (1–11) of lobane– and prenyleudesmane–types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher’s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium.

Skrining Fitokimia Ekstrak Metanol Karang Lunak Lobophytum sp.

Abstract. Soft corals produce several bioactive compounds that can be used. One of the soft corals that has the potential to produce bioactive compounds is lobophytum sp.. The purpose of this study was to determine the chemical component of the soft coral lobophytum sp. . Sample extraction was done by the using of macerationmethod with methanol solvent.Theobtainedextract then tested for its chemical component. The chemical component that tested in this study were alkaloids, flavonoids, triterpenoids/ steroids, tanins and saponins. The results showed that the soft coral lobophytum sp. contains some chemical componentssuch as alkaloids, flavonoids, triterpenoids and saponins.Keywords: soft coral, lobophytum, chemical component.

Anti-Inflammatory Cembrane-Type Diterpenoids and Prostaglandins from Soft Coral Lobophytum sarcophytoides.

Two new cembrane-type diterpenoids, lobophytins A (1) and B (3), and four new prostaglandins, (5E)-PGB2 (10), (5E)-13,14-dihydro-PGB2 (11), 13,14-dihydro-PGB2 (12) and 13,14-dihydro-PGB2-Me (13), together with ten known compounds were isolated from the soft coral Lobophytum sarcophytoides. The structures of these new secondary metabolites were identified by high resolution mass spectrometry (HR-ESIMS), nuclear magnetic resonance (NMR) and electron circular dichroism (ECD) analyses, as well as the modified Mosher’s method. Compounds 6, 7, 9, 10, 12, 13, 15 and 16 showed potential anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in RAW264.7 cells that were activated by lipopolysaccharide, with IC50 values ranging from 7.1 to 32.1 μM and were better than the positive control indomethacin, IC50 = 39.8 μM.

Bacterial Symbionts of Soft Coral Lobophytum Sp. From Panjang Island, Jepara, Indonesia With Antimicrobial MDR TB Potency

Tubercolusis is a disease that attacks the lungs. The disease is caused by the bacterium mycobacterium tubercolusis. The bacteria mycobacterium tubercolusis can be killed by antibiotics. However, continuous use of antibiotics can cause bacterial resistance. So we need to find new drugs that can prevent multi-drug resistant tuberculosis. This study aims to determine the antibacterial activity of MDR TB from soft coral symbiont bacteria Lobophytum sp. There were 6 bacterial isolates obtained from soft coral Lobophytum sp. One isolate from Lobophytum-associated bacteria were successfully screened for antimycobacterial against MDR TB bacteria. PLO2 was found to inhibit the growth of MDR TB (MDR TB strain SIRE and R). Based on the results of identification with PCR, soft coral symbionts of PLO2 was closely related to Virgibacillus marismortui with homology of 99%.

Three new capnosane-type diterpenoids from the South China Sea soft coral Lobophytum sp.

Three new diterpenoids with an unusual capnosane skeleton named lobophytrols A–C (1–3) were isolated from the South China Sea soft coral Lobophytum sp. along with one known related diterpene, (11S,12S,1E,3E,7E)-11,12-epoxycembra-1,3,7-triene (7). Their structures were elucidated on the basis of spectroscopic analysis and by comparison with those reported in the literature.

Cytotoxic polyhydroxylated steroids from the South China Sea soft coral Lobophytum sp.

Four new polyhydroxylated steroids lobophysterols A–D (1–4), together with two known related compounds sarcophytosterol (5) and klyflaccisteroid B (6), were isolated from the South China Sea soft coral Lobophytum sp. Their structures were elucidated on the basis of spectroscopic analysis and by comparison with those reported in the literature. In bioassay, compound 4 showed weak cytotoxicities against HT-29, SNU-398, and Capan-1 cells.

Quorum Sensing Interference and Structural Variation of Quorum Sensing Mimics in Australian Soft Coral

Bacterial Quorum Sensing (QS), the indirect regulation of gene expression through production and detection of small diffusible molecules, has emerged as a point of interaction between eukaryotic host organisms and their associated microbial communities. The extracellular nature of QS molecules enables interference in QS systems, in many cases via mimicry. This study targeted QS induction and inhibition in soft coral holobionts, as many soft coral species commonly contain compounds with structural similarities to the well-studied bacterial QS molecules acyl homoserine lactones. Screening with two bacterial biosensors, Agrobacterium tumefaciens A136 and Chromobacterium violaceum CV026, demonstrated that QS interference differed between the two biosensor strains and extended across the soft coral families Alcyoniidae, Clavulariidae, Nephtheidae, and Xeniidae. Bioassay-guided fractionation revealed chemical activity patterns, particularly in the induction of QS. Cembranoid diterpenes from active fractions were purified and tested for QS interference activity. Interestingly, the type of QS activity (induction or inhibition) in A. tumefaciens A136 correlated with structural variability of the secondary oxygen ring; cembranoid diterpeneswith a furan ring or five-membered lactone induced QS, while compounds with larger (six or seven membered) lactone rings inhibited QS. Addition of the dominant cembranoid diterpene in the soft coral Lobophytum compactum, isolobophytolide, to bacterial culture media increased the number and morphological diversity of bacteria recovered from the mucosal layer of this soft coral, demonstrating a selective effect on certain members of the soft coral bacterial community. The identity and QS activity of recovered isolates differed between the mucosal layers of L. compactum and Sinularia flexibilis. In conclusion, this study provides information on the complexity of the interaction between soft corals and their associated bacteria, as well as, a structural understanding of how QS mimic compounds are able to interfere with a bacterial communication system.

Lobohedleolide suppresses hepatitis C virus replication via JNK/c-Jun-C/EBP-mediated down-regulation of cyclooxygenase-2 expression

Hepatitis C virus (HCV) chronically infects 2–3% people of the global population, which leads to liver cirrhosis and hepatocellular carcinoma. Drug resistance remains a serious problem that limits the effectiveness of US Food and Drug Administration (FDA)-approved direct-acting antiviral (DAA) drugs against HCV proteins. The objective of our study was to discover new antivirals from natural products to supplement current therapeutics. We demonstrated that lobohedleolide, isolated from the Formosan soft coral Lobophytum crassum, significantly reduced HCV replication in replicon cells and JFH-1 infection system, with EC50 values of 10 ± 0.56 and 22 ± 0.75 μM, respectively, at non-toxic concentrations. We further observed that the inhibitory effect of lobohedleolide on HCV replication is due to suppression of HCV-induced cyclooxygenase-2 (COX-2) expression. Based on deletion-mutant analysis of the COX-2 promoter, we identified CCAAT/enhancer-binding protein (C/EBP) as a key transcription factor for the down-regulation of COX-2 by lobohedleolide, through which lobohedleolide decreased the phosphorylation of c-Jun NH2-terminal protein kinase and c-Jun to suppress HCV-induced C/EBP expression. The combination treatment of lobohedleolide with clinically used HCV drugs synergistically reduced HCV RNA replication, indicating that lobohedleolide exhibited a high biomedical potential to be used as a supplementary therapeutic agent to control HCV infection.

Release of dissolved and particulate organic matter by the soft coral Lobophytum and subsequent microbial degradation

Understanding the release and remineralization of organic matter by benthic macroorganisms provides insight into nutrient cycling and microbial metabolism in coral reef environments. The release rate of particulate (POC) and dissolved organic carbon (DOC) by the soft coral Lobophytum crassum was quantified and subsequent bacterial growth rates determined in response to this resource, and compared with results from those of the common hard coral Acropora intermedia. The results of this study show that the soft coral released more DOC than POC into the surrounding seawater, similar to what was measured for the hard coral species. However, the soft coral-derived organic matter fostered a lower microbial growth rate with a lower growth efficiency compared to DOC and POC of hard corals, likely due to the lower C:N ratio of the organic matter derived from soft corals. These results suggest that soft coral exudates are relatively refractory compared to the mucus of hard corals. Possible phase shifts from hard to soft corals on degraded reefs may represent very different changes in microbial community dynamics and metabolism as compared to the widely studied coral-algal phase shifts.

Endophyte microbial characteristic of soft corals Lobophytum sp and Sinularia sp collected from Maspari Island waters, South Sumatera

Soft corals have bioactive compounds to potential as marine natural products, but the over exploitive to destroy of that ecosystem. Therefor endophyte microbial isolation can be effort to prevent that matters. This research aimed to isolate and characteristic on the entophyte microbial of soft coral Lobophytum sp and Sinularia sp that collated from Maspari island waters. Methodology of research were establishing growth of microbial samples (bacterial and fungal), isolation and characterization. Total of bacteria colony of Lobophytum sp were obtained about 5 isolates, and Sinularia sp were about 4 isolates. The macroscopic characteristic showed that whole bacteria had white colors. That colonies had undulate, entire and curl (the edge of colony) and circular and irregular (for colony shape). For fungal of Lobophytum sp were obtained about 3 isolates, while Sinularia sp had only one isolate. The fungal colonies macroscopic characteristic showed yellow, green and white color, while shaped and edges colonies were thickened. spread, thin, round, dark, and the whole of isolates had filamentous hyphae.

Anti-Inflammatory Polyoxygenated Steroids from the Soft Coral Lobophytum michaelae

Three new polyoxygenated steroids, michosterols A–C (1–3), and four known compounds (4–7) were isolated from the ethyl acetate (EtOAc) extract of the soft coral Lobophytum michaelae, collected off the coast of Taitung. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and comparison of the nuclear magnetic resonance (NMR) data with related steroids. The cytotoxicity of compounds 1–3 against the proliferation of a limited panel of cancer cell lines was assayed. Compound 1 was found to display moderate cytotoxicity against adenocarcinomic human alveolar basal epithelial (A549) cancer cells. It also exhibited potent anti-inflammatory activity by suppressing superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-stimulated human neutrophils. Furthermore, 3 could effectively inhibit elastase release, as well.

Lobocrassin B Induces Apoptosis of Human Lung Cancer and Inhibits Tumor Xenograft Growth.

Lobocrassin B, a natural cembrane-type compound isolated from the soft coral Lobophytum crassum, has been shown to have significant biological effects, including anticancer activity. As the most common cause of cancer mortality worldwide, lung cancer remains a major concern threatening human health. In the current study, we conducted in vitro experiments to demonstrate the inhibiting effect of Lobocrassin B on CL1-5 and H520 human lung cancer cells growth and to explore the underlying mechanisms, as well as in nude mice bearing CL1-5 tumor xenografts. Lobocrassin B exerted cytotoxic effects on lung cancer cells, as shown by decreasing cell viability, and inducing apoptosis, oxidative stress and mitochondrial dysfunction. In addition, the increased level of Bax, cleaved caspase-3, -9 and -8, and the suppression of Bcl-2 were observed in the Lobocrassin B treated cells. Moreover, in vivo assays verified the significance of these results, revealing that Lobocrassin B inhibited CL1-5 tumor xenograft growth and that inhibitory effects were accompanied by a marked increase in tumor cell apoptosis. In conclusion, the results suggested that Lobocrassin B could be a potential anticancer compound for its propensity to inhibit growth and induce apoptosis in human lung cancer cells.

Anti-Inflammatory Dembranoids from the Soft Coral Lobophytum crassum.

Cembrane-type diterpenoids are among the most frequently encountered natural products from the soft corals of the genus Lobophytum. In the course of our investigation to identify anti-inflammatory constituents from a wild-type soft coral Lobophytum crassum, two new cembranoids, lobophyolide A (1) and B (2), along with five known compounds (3–7), were isolated. The structures of these natural products were identified using NMR and MS spectroscopic analyses. Compound 1 was found to possess the first identified α-epoxylactone group among all cembrane-type diterpenoids. The in vitro anti-inflammatory effect of compounds 1–5 was evaluated. The results showed that compounds 1–5 not only reduced IL-12 release, but also attenuated NO production in LPS-activated dendritic cells. Our data indicated that the isolated series of cembrane-type diterpenoids demonstrated interesting structural features and anti-inflammatory activity which could be further developed into therapeutic entities.

Anti-Inflammatory Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium.

New lobane-based diterpenoids lobovarols A–D (1–4) and a prenyleudesmane-type diterpenoid lobovarol E (5) along with seven known related diterpenoids (6–12) were isolated from the ethyl acetate extract of a Taiwanese soft coral Lobophytum varium. Their structures were identified on the basis of multiple spectroscopic analyses and spectral comparison. The absolute configuration at C-16 of the known compound 11 is reported herein for the first time. The anti-inflammatory activities of compounds 1–12 were assessed by measuring their inhibitory effect on N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils. Metabolites 2, 5, and 11 were found to show moderate inhibitory activity on the generation of superoxide anion, while compounds 5, 8, 11, and 12 could effectively suppress elastase release in fMLP/CB-stimulated human neutrophil cells at 10 μM. All of the isolated diterpenoids did not exhibit cytotoxic activity (IC50 > 50 μM) towards a limited panel of cancer cell lines.

Altered acrylic acid concentrations in hard and soft corals exposed to deteriorating water conditions

A reliable marker of early coral response to environmental stressors can help guide decision-making to mitigate global coral reef decline by detecting problems before the development of clinically observable disease. We document the accumulation of acrylic acid in two divergent coral taxa, stony small polyp coral ( Acropora sp.) and soft coral ( Lobophytum sp.), in response to deteriorating water quality characterized by moderately increased ammonia (0.25 ppm) and phosphate (0.15 ppm) concentrations and decreased calcium (360 ppm) concentration, using nuclear magnetic resonance spectroscopy (NMR)-based metabolomic techniques. Changes in acrylic acid concentration in polyp tissues free of zooxanthellae suggest that acrylic acid could be a product of animal metabolism and not exclusively a metabolic by-product of the osmolyte dimethylsulfoniopropionate (DMSP) in marine algae or bacteria. Our findings build on previously documented depletions of acrylic acid in wild coral potentially correlated to temperature stress and provide additional insight into approaches to further characterize the nature of the metabolic accumulation of acrylic acid under controlled experimental conditions.

PENGARUH CAHAYA TERHADAP TINGKAT KELANGSUNGAN HIDUP DAN PERTUMBUHAN KARANG LUNAK LOBOPHYTUM STRICTUM (OCTOCORALIA: ALCYONACEA) HASIL TRANSPLANTASI PADA SISTEM RESIRKULASI

Penelitian yang dilakukan untuk mengetahui pengaruh cahaya terhadap pertumbuhan karang lunak Lobophytum strictum hasil transplantasi dilakukan dengan pemeliharaan karang lunak pada dua buah kolam, yaitu kolam terbuka (cahaya) dan kolam tertutup (tanpa cahaya). Pada masing-masing kolam ditempatkan 16 fragmen karang lunak yang sudah ditransplantasikan. Kelangsungan hidup dan pertumbuhan karang lunak berbeda signifikan antar perlakuan cahaya (P<0,05). Karang lunak yang dipelihara di kolam terbuka mampu bertahan hidup 100% (12 minggu), dengan disertai peningkatan panjang (5,95-10,04 cm) dan lebar (5,27-6,84 cm) fragmen karang. Hal yang berbeda ditunjukkan karang lunak yang dipelihara di kolam tertutup, hanya mampu bertahan hidup hingga minggu ke-8 (62,5%). Hal ini disertai dengan penurunan panjang (8,25-5,25 cm) dan lebar (9,14-4,86 cm) fragmen setiap minggunya.