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Simultaneous Determination and Recognition Analysis of Coumarins in Angelica decursiva and Peucedanum praeruptorum by HPLC-DAD.

Hye Mi KIM ; Su Yang JEONG ; Sun Min KIM ; Kyu Ha LEE ; Jong Hwan KIM ; Rack Seon SEONG

Natural Product Sciences.2016;22(3):162-167. doi:10.20307/nps.2016.22.3.162

Peucedani Radix is the root of Angelica decursiva Franchet et Savatier (=Peucedanum decursivum Maximowicz) or Peucedanum praeruptorum Dunn in several Asian countries. The coumarins contained in Peucedani Radix were quantitatively analyzed using HPLC-DAD to develop a simultaneous determination for the quality control of A. decursiva and P. praeruptorum. For quantitative analysis, four major coumarins contained in these medicinal plants were assessed. Nodakenin (1), nodakenetin (2), praeruptorin A (3), and praeruptorin B (4) were separated with a Phenomenex Luna C18 column (5 µm, 4.6 × 250 mm) under the gradient conditions using distilled water with 0.1% phosphoric acid and acetonitrile with 0.1% phosphoric acid as the mobile phase, at a flow rate of 1.0 ml/min and a detection wavelength of 330 nm. This method was fully validated for linearity, accuracy, precision, recovery, and limit of detection and quantification. As a result, A. decursiva and P. praeruptorum were clearly classified by the quantification of four major coumarins in extracts. Also, the pattern recognition analysis based on HPLC indicates that all of the samples were largely clustered into two groups. Therefore, it is possible to distinguish between A. decursiva and P. praeruptorum and contribute to quality control.
Angelica* ; Asian Continental Ancestry Group ; Chromatography, High Pressure Liquid ; Coumarins* ; Humans ; Limit of Detection ; Methods ; Plants, Medicinal ; Quality Control ; Water

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Chemical Constituents from Leaves of Pileostegia viburnoides Hook.f.et Thoms.

Xiao Jun LI ; Zu Zhen LIU ; Kwan Woo KIM ; Xiang WANG ; Zhi LI ; Youn Chul KIM ; Chang Soo YOOK ; Xiang Qian LIU

Natural Product Sciences.2016;22(3):154-161. doi:10.20307/nps.2016.22.3.154

Phytochemical investigation on the leaves of Pileostegia viburnoides Hook.f.et Thoms led to the isolation of twenty-five compounds, and their structures were identified as n-dotriacontane (1), taraxeryl acetate (2), friedelin (3), epifriedelinol (4), canophyllal (5), stigmast-4-en-3-one (6), stigmasterol (7), (24R)-5A-stigmastane-3,6-dione (8), ursolic acid (9), pomolic acid (10), umbelliferone (11), 4-epifriedelin (12), n-octatriacontanol (13), β-amyrin (14), α-amyrin (15), taraxerol (16), nonadecanol (17), friedelane (18), arachic acid (19), protocatechuic acid (20), n-pentatriacontanol (21), hexadecanoic acid (22), vincosamide (23), daucosterol (24), and skimming (25), respectively. To our best knowledge, compounds 1, 2, 12, 13, 17 - 19 and 21-23 were new within Saxifragaceae family. Compounds 15, 16, and 20 were produced from this genus for the first time. Compounds 4, 14 and 25 were first obtained from species P. viburnoides and compounds 3, 5 - 11, and 24 were achieved from the leaves of P. viburnoides for the first time. Furthermore, the anti-neuroinflammatory activity of these isolates was evaluated.
Coumarins ; Humans ; Palmitic Acid ; Saxifragaceae ; Stigmasterol ; Triterpenes

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Anti-inflammatory Effect of Mangosteen (Garcinia mangostana L.) Peel Extract and its Compounds in LPS-induced RAW264.7 Cells.

Wahyu WIDOWATI ; Lusiana DARSONO ; Jo SUHERMAN ; Nurul FAUZIAH ; Maesaroh MAESAROH ; Pande Putu ERAWIJANTARI

Natural Product Sciences.2016;22(3):147-153. doi:10.20307/nps.2016.22.3.147

Inflammation plays an important role in host defense against external stimuli such as infection by pathogen, endotoxin or chemical exposure by the production of the inflammatory mediators that produced by macrophage. Anti-inflammatory factor is important to treat the dangers of chronic inflammation associated with chronic disease. This research aims to analyze the anti-inflammatory effects of Garcinia mangostana L. peel extract (GMPE), α-mangostin, and γ-mangostin in LPS-induced murine macrophage cell line (RAW 264.7) by inhibiting the production of inflammatory mediators. The cytotoxic assay of G. mangostana L. extract, α-mangostin, and γ-mangostin were performed by MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) to determine the safe and non-toxic concentration in RAW 264.7 for the further assay. The concentration of inflammatory mediators (COX-2, IL-6, and IL-1β) were measured by the ELISA-based assay and NO by the nitrate/nitrite colorimetric assay in treated LPS-induced RAW 264.7 cells. The inhibitory activity was determined by the reducing concentration of inflammatory mediators in treated LPS-induced RAW 264.7 over the untreated cells. This research revealed that GMPE, α-mangostin, and γ-mangostin possess the anti-inflammatory effect by reducing COX-2, IL-6, IL-1β, and NO production in LPS-induces RAW 264.7 cells.
Cell Line ; Chronic Disease ; Fibrinogen ; Garcinia mangostana* ; Inflammation ; Interleukin-6 ; Macrophages ; RAW 264.7 Cells

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Chemical Constituents from the Aerial Parts of Bupleurum falcatum L. and Biological Evidences.

Nguyen Huu TUNG ; Takuhiro UTO ; Osamu MORINAGA ; Yukihiro SHOYAMA

Natural Product Sciences.2015;21(2):71-75.

In this study, phytochemical investigation on the aerial parts of Bupleurum falcatum resulted in the isolation of fourteen compounds including three quinic acid derivatives (1 - 3), five flavonoids (4 - 8), three monoterpene glycosides (9 - 11), and three saikosaponins (12 - 14). Compound 1 was first isolated from nature and unambiguously determined to be 3-O-feruloyl 5-O-caffeoylquinic acid on the basis of the extensive spectroscopic evidence. Biological testing revealed that saikosaponin A (12) and saikosaponin D (13) showed moderate antiproliferative effects on HL-60 and HepG2 cancer cell lines.
Bupleurum* ; Cell Line ; Flavonoids ; Glycosides ; Quinic Acid

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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

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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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