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Epi-Leptosphaerin: A New L-Isoascorbic Acid Derivative from Marine Sponges.

Roshan R KULKARNI ; A Reum JO ; Young Ho KIM ; MinKyun NA

Natural Product Sciences.2015;21(4):293-296. doi:10.20307/nps.2015.21.4.293

A new L-isoascorbic acid derivative epi-leptosphaerin (1) and two known compounds leptosphaerin (2), and verongamine (3) were isolated from sponges of the orders Verongida and Thorectidae. Compounds 1 and 2 are most likely of sponge-associated fungal origin. In the present study, isolated compounds were investigated for their inhibition of soluble epoxide hydrolase (sEH), which is considered a promising target for the management of pain, inflammation, and comorbidities associated with diabetes. Compound 3, verongamine, displayed weak inhibitory activity against sEH with an IC50 value 51.5 +/- 1.0 microM.
Comorbidity ; Inflammation ; Inhibitory Concentration 50 ; Porifera*

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Two New Scalaranes from a Korean Marine Sponge Spongia sp..

Inho YANG ; Sang Jip NAM ; Heonjoong KANG

Natural Product Sciences.2015;21(4):289-292. doi:10.20307/nps.2015.21.4.289

Intensive chemical investigation of Korean marine sponge Spongia sp. has led to the isolation of two new scalaranes. The planar structures of the new compounds 1 and 2 were determined through 1D and 2D NMR spectral data analysis, while the relative stereochemistry of the compounds was determined based on the analysis of 1H-1H coupling constants and NOESY spectroscopic data. Compounds 1 and 2 did not display any significant biological activities on farnesoid X-activated receptor (FXR) in co-transfection assay.
Porifera* ; Statistics as Topic

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Viriditoxin Induces G2/M Cell Cycle Arrest and Apoptosis in A549 Human Lung Cancer Cells.

Ju Hee PARK ; Tae Hwan NOH ; Haibo WANG ; Nam Deuk KIM ; Jee H JUNG

Natural Product Sciences.2015;21(4):282-288. doi:10.20307/nps.2015.21.4.282

Viriditoxin is a fungal metabolite isolated from Paecilomyces variotii, which was derived from the giant jellyfish Nemopilema nomurai. Viriditoxin was reported to inhibit polymerization of FtsZ, which is a key protein for bacterial cell division and a structural homologue of eukaryotic tubulin. Both tubulin and FtsZ contain a GTP-binding domain, have GTPase activity, assemble into protofilaments, two-dimensional sheets, and protofilament rings, and share substantial structural identities. Accordingly, we hypothesized that viriditoxin may inhibit eukaryotic cell division by inhibiting tubulin polymerization as in the case of bacterial FtsZ inhibition. Docking simulation of viriditoxin to beta-tubulin indicated that it binds to the paclitaxel-binding domain and makes hydrogen bonds with Thr276 and Gly370 in the same manner as paclitaxel. Viriditoxin suppressed growth of A549 human lung cancer cells, and inhibited cell division with G2/M cell cycle arrest, leading to apoptotic cell death.
Apoptosis* ; Cell Cycle Checkpoints* ; Cell Cycle* ; Cell Death ; Cell Division ; Eukaryotic Cells ; GTP Phosphohydrolases ; Humans* ; Hydrogen ; Lung Neoplasms* ; Lung* ; Paclitaxel ; Paecilomyces ; Polymerization ; Polymers ; Tubulin

4

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A Novel Bromoindole Alkaloid from a Korean Colonial Tunicate Didemnum sp..

Dongyup HAHN ; Geum Jin KIM ; Hyukjae CHOI ; Heonjoong KANG

Natural Product Sciences.2015;21(4):278-281. doi:10.20307/nps.2015.21.4.278

Chemical investigation on a colonial marine tunicate, Didemnum sp. led to the isolation of a series of indole alkaloids including a new (1) and two known metabolites (2-3). Based on the spectroscopic analysis including 1D and 2D NMR along with MS spectra, the structure of 1 (16-epi-18-acetyl herdmanine D) was elucidated as a new amino acid derivative. The absolute configuration of 1 was determined by comparison of specific rotation with the known compound. The structures of compounds 2 and 3 were also identified as bromoindole containing compounds N-(6-bromo-1H-indole-3-carbonyl)-L-arginine and (6-bromo-1H-indol-3-yl) oxoacetamide, respectively, based on 1H and 13C NMR data, MS data and specific rotation value. Their pharmacological potentials as antibacterial agents and FXR antagonists were investigated, but no significant activity was found. However, the structural similarity of compound 1 to compound 4 suggested the antiinflammatory potential of compound 1.
Anti-Bacterial Agents ; Indole Alkaloids ; Urochordata*

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Salternamide E from a Saltern-derived Marine Actinomycete Streptomyces sp..

Seong Hwan KIM ; Yoonho SHIN ; Sang Kook LEE ; Jongheon SHIN ; Dong Chan OH

Natural Product Sciences.2015;21(4):273-277. doi:10.20307/nps.2015.21.4.273

Comprehensive chemical analysis of extracts and fractions of marine actinomycete strains led to the discovery of a new minor secondary metabolite, salternamide E (1), from a saltern-derived halophilic Streptomyces strain. The planar structure of salternamide E (1) was elucidated by a combinational analysis of spectroscopic data including NMR, MS, UV, and IR. The absolute configuration of salternamide E (1) was determined by circular dichroism spectroscopic analysis. Salternamide E displayed weak cytotoxicity against various human carcinoma cell lines.
Cell Line ; Circular Dichroism ; Humans ; Streptomyces*

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Anti-inflammatory Effect of Dactyloquinone B and Cyclospongiaquinone-1 Mixture in RAW264.7 Macrophage and ICR Mice.

Dong Sung LEE ; In Hyun HWANG ; Nam Kyung IM ; Gil Saeng JEONG ; Minkyun NA

Natural Product Sciences.2015;21(4):268-272. doi:10.20307/nps.2015.21.4.268

Sesquiterpene-quinone is a class of secondary metabolites frequently encountered from marine sponge. The present study was designed to examine the anti-inflammatory action of sponge-derived dactyloquinone B (DQB) and cyclospongiaquinone-1 (CSQ1) mixture using lipopolysaccharide (LPS)-induced inflammatory responses. We measured the production of nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta), and interleukin-6 (IL-6) and expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein. TNF-alpha, IL-1beta, and IL-6 production, which increased by treatment with LPS, were significantly inhibited by DQB and CSQ1 mixture. It also decreased the production of NO production, and iNOS and COX-2 expression. Furthermore, it reduced 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ear edema of ICR mice. These results demonstrate that sesquiterpene-quinone, DQB and CSQ1 mixture, might serve as a chemical pipeline for the development of anti-inflammatory agent.
Animals ; Cyclooxygenase 2 ; Ear ; Edema ; Interleukin-1beta ; Interleukin-6 ; Macrophages* ; Mice ; Mice, Inbred ICR* ; Nitric Oxide ; Nitric Oxide Synthase Type II ; Porifera ; Tumor Necrosis Factor-alpha

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Deuteromethylactin B from a Freshwater-derived Streptomyces sp..

Anam F SHAIKH ; Maryam ELFEKI ; Samantha LANDOLFA ; Urszula TANOUYE ; Stefan J GREEN ; Brian T MURPHY

Natural Product Sciences.2015;21(4):261-267. doi:10.20307/nps.2015.21.4.261

Compared to their terrestrial and marine counterparts, little is known about the capacity of freshwater-derived actinomycete bacteria to produce novel secondary metabolites. In the current study, we highlight the disparities that exist between cultivation-independent and -dependent analyses of actinomycete communities from four locations in Lake Michigan sediment. Furthermore, through phylogenetic analysis of strains isolated from these locations, we identified a Streptomyces sp., strain B025, as being distinct from other Streptomyces spp. isolated from sediment. Upon fermentation this strain produced a rare class of eight-membered lactone secondary metabolites, which have been for their antitumor properties. We used spectroscopic and chemical derivitization techniques to characterize octalactin B (1) in addition to its corresponding novel, unnatural degradation product (2).
Bacteria ; Fermentation ; Fresh Water ; Lakes ; Michigan ; Streptomyces*

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Graphiumins I and J, New Thiodiketopiperazines from the Marine-derived Fungus Graphium sp. OPMF00224.

Takashi FUKUDA ; Kenichiro NAGAI ; Yuko KURIHARA ; Akihiko KANAMOTO ; Hiroshi TOMODA

Natural Product Sciences.2015;21(4):255-260. doi:10.20307/nps.2015.21.4.255

Two new thiodiketopiperazines (TDKPs), designated graphiumins I (1) and J (2), were isolated from the culture broth of the marine-derived fungus Graphium sp. OPMF00224 by solvent extraction, silica gel column chromatography, and HPLC. Their absolute structures were elucidated by spectroscopic analyses (1D and 2D NMR data, ROESY correlations, and CD data) and chemical methods. They were found to be structurally rare TDKPs with a phenylalanine-derived indolin substructure. Compounds 1 and 2 inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus (MRSA) with IC50 values of 63.5 and 76.5 microg/ml, respectively, without inhibiting its growth, even at 250 microg/ml.
Chromatography ; Chromatography, High Pressure Liquid ; Fungi* ; Inhibitory Concentration 50 ; Methicillin-Resistant Staphylococcus aureus ; Silica Gel

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Anti-Inflammatory Effect of Violapyrones B and C from a Marine-derived Streptomyces sp..

Hwa Sun LEE ; Bong Jeun AN ; Hyeon Jeong KIM ; Yong Hun CHO ; Dong In KIM ; Jae Yoon JANG ; Jae Hoon KWAK ; Hyi Seung LEE ; Yeon Ju LEE ; Jong Seok LEE ; Hee Jae SHIN

Natural Product Sciences.2015;21(4):251-254. doi:10.20307/nps.2015.21.4.251

Recently, we reported violapyrones B, C, H and I, unusual 3, 4, 6-trisubstituted alpha-pyrone derivatives, from the culture broth of the marine Streptomyces sp. 112CH148. In previous studies, violapyrones have been shown to have antibacterial and antitumor activities. However, the anti-inflammatory effect of violapyrones has not been reported yet. As part of our ongoing study for the discovery of bioactive metabolites from marine microorganisms, we found that violapyrones also have anti-inflammatory activity. In this study, we investigated the effect of violapyrones on LPS-induced inflammatory responses in vitro. Violapyrones B and C did not affect the viability of RAW 264.7 cells at concentrations up to 25 microM. However, violapyrones B and C inhibited the production of NO compared to the LPS-induced control. In addition, violapyrones B and C down-regulated the expression of iNOS protein in LPS-stimulated RAW 264.7 cells. To the best of our knowledge, this is the first report on the anti-inflammatory activity of violapyrones B and C.
Streptomyces*

10

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The New Phytoformula Containing Morus alba, Schizandra sinensis and Asparagus cochinchinensis Inhibits Lung Inflammation in vitro and in vivo.

Hyeon Gun JEONG ; Chan Woo LEE ; Ju Hee LEE ; So Joong KIM ; Yong Soo KWON ; Yisu HEO ; Hyun Pyo KIM

Natural Product Sciences.2016;22(1):70-75. doi:10.20307/nps.2016.22.1.70

A phytoformula containing the root barks of Morus alba, the fructus of Schizandra sinensis and the roots of Asparagus cochinchinensis (MSA) was prepared as a potential new herbal remedy, and its therapeutic potential for alleviating inflammatory lung conditions was examined. For in vivo evaluation, an animal model of lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice was used. With oral administration of 6 - 60 mg/kg, MSA potently and dose-dependently inhibited bronchitis-like symptoms in acute lung injury induced by intranasal treatment of LPS as judged by the number of cells in the bronchoalveolar lavage fluid (BALF) and histological observation. The inhibitory potency was comparable with that of dexamethasone. For in vitro assay, the effects on the production of proinflammatory molecules in lung epithelial cells and alveolar macrophages were examined. Although MSA inhibited IL-6 production in IL-1β-treated lung epithelial cells (A549) only at a high concentration (300 µg/ml), the formula strongly and concentration-dependently inhibited NO production in LPS-treated alveolar macrophages (MH-S) at 20 - 300 µg/ml. Based on all of these findings, the new phytoformula MSA is suggested to have the potential to control inflammatory lung diseases including bronchitis, at least in part, by inhibiting inducible nitric oxide synthase-catalyzed NO production.
Acute Lung Injury ; Administration, Oral ; Animals ; Bronchitis ; Bronchoalveolar Lavage Fluid ; Dexamethasone ; Epithelial Cells ; Interleukin-6 ; Lung Diseases ; Lung* ; Macrophages, Alveolar ; Mice ; Models, Animal ; Morus* ; Nitric Oxide ; Pneumonia* ; Schisandra*

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