Publications by authors named "Seung Mok Ryu"

26 Publications

  • Page 1 of 1

Clerodane Diterpenoids Identified from Showing Antifungal Activity against Plant Pathogens.

J Agric Food Chem 2021 Sep 1;69(36):10527-10535. Epub 2021 Sep 1.

Center for Eco-Friendly New Materials, Korea Research Institute of Chemical Technology, Daejeon 34114, Korea.

In the search for new natural resources showing plant disease control effects, we found that the methanol extract of suppressed fungal disease development in plants. To identify the bioactive substances, the methanol extract of was extracted by organic solvents, and consequently, four new 2-oxo-clerodane diterpenes (), a new 4(3 → 2)--clerodane diterpene (), together with ten known compounds () were isolated and identified from the extracts. Of the new compounds, compound showed a broad spectrum of antifungal activity with moderated minimum inhibitory concentration (MIC) values in a range of 50-100 μg/mL against tested fungal pathogens. Considering with the known compounds, compound showed the most potent antifungal activity with an MIC value in the range of 6.3-12.5 μg/mL. When compound was evaluated for an antifungal activity against rice blast, tomato late blight, and pepper anthracnose, compound reduced the plant disease by at least 60% compared to the untreated control at concentrations of 250 and 500 μg/mL. Together, our results suggested that the methanol extract of twigs and leaves of and its major compound could be used as a source for the development of eco-friendly plant protection agents.
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http://dx.doi.org/10.1021/acs.jafc.1c02200DOI Listing
September 2021

Gekko gecko extract attenuates airway inflammation and mucus hypersecretion in a murine model of ovalbumin-induced asthma.

J Ethnopharmacol 2021 Aug 27;282:114574. Epub 2021 Aug 27.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, 111, Geonjae-ro, Naju-si, 58245, South Korea. Electronic address:

Ethnopharmacological Relevance: Gekko gecko is used as a traditional medicine for various diseases including respiratory disorders in northeast Asian countries, mainly Korea, Japan, and China.

Aim Of The Study: Allergic asthma is a chronic respiratory disease caused by an inappropriate immune response. Due to the recent spread of coronavirus disease 2019, interest in the treatment of pulmonary disorders has rapidly increased. In this study, we investigated the anti-asthmatic effects of G. gecko extract (GGE) using an established mouse model of ovalbumin-induced asthma.

Materials And Methods: To evaluate the anti-asthmatic effects of GGE, we evaluated histological changes and the responses of inflammatory mediators related to allergic airway inflammation. Furthermore, we investigated the regulatory effects of GGE on type 2 helper T (Th2) cell activation.

Results: Administration of GGE attenuated asthmatic phenotypes, including inflammatory cell infiltration, mucus production, and expression of Th2 cytokines. Furthermore, GGE treatment reduced Th2 cell activation and differentiation.

Conclusions: These results indicate that GGE alleviates allergic airway inflammation by regulating Th2 cell activation and differentiation.
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http://dx.doi.org/10.1016/j.jep.2021.114574DOI Listing
August 2021

Phenolic constituents isolated from Senna tora sprouts and their neuroprotective effects against glutamate-induced oxidative stress in HT22 and R28 cells.

Bioorg Chem 2021 Sep 23;114:105112. Epub 2021 Jun 23.

KIST Gangneung Institute of Natural Products, Korea Institute of Science and Technology (KIST), Gangneung 25451, Republic of Korea. Electronic address:

The consumption of sprouts has been steadily increasing due to their being an excellent source of nutrition. It is known that the bioactive constituents of legumes can be increased after germination. In this study, the extract from Senna tora sprouts is shown to exhibit improved radical scavenging activities and better neuroprotective effects in HT22 hippocampal neuronal (HT22) and R28 retina precursor (R28) cells than those from seeds due to an increased content of phenolic constituents, especially compounds 1 and 3-6. A phytochemical investigation of S. tora sprouts resulted in the isolation of two new naphthopyrone glycosides (1-2) with 27 previously reported compounds. Their structures were determined via interpreting spectroscopic data. Compounds 1 and 3-6 were found to possess radical scavenging activities and neuroprotective effects against oxidative stress in both neuronal cells. Hence, Senna tora sprouts and their constituents may be developed as natural neuroprotective agents via antioxidative effects.
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http://dx.doi.org/10.1016/j.bioorg.2021.105112DOI Listing
September 2021

Chemical constituents from basidiomycete Basidioradulum radula culture medium and their cytotoxic effect on human prostate cancer DU-145 cells.

Bioorg Chem 2021 Sep 5;114:105064. Epub 2021 Jun 5.

Department of Plant Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea. Electronic address:

Eight new naphtho[1,2-c]furan derivatives (1-8) along with six known analogues (9-14) were isolated from culture medium of the basidiomycete Basidioradulum radula. The structures of these compounds were identified using spectroscopic analysis, and their absolute configurations were resolved using X-ray diffraction, ECD, and VCD. Compounds 7 and 14 inhibited the cell viability of human prostate cancer DU-145 cells with IC values of 7.54 ± 0.03 μM and 5.04 ± 0.03 μM, respectively. At 8 μM, compounds 7 and 14 increased the percentage of apoptotic cells and upregulated the protein expression related to the apoptosis caspase pathways in DU-145 cells. Furthermore, the hallmarks of cells undergoing apoptosis, such as chromatin condensation, were also observed at this concentration. However, compound 7 and 14 showed no effect on the proliferation of splenocytes isolated from cyclophosphamide-induce immunosuppressed mice.
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http://dx.doi.org/10.1016/j.bioorg.2021.105064DOI Listing
September 2021

Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense.

Bioorg Chem 2021 08 24;113:105012. Epub 2021 May 24.

Department of Plant Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea. Electronic address:

Inflammation is a vital process that maintains tissue homeostasis. However, it is widely known that uncontrolled inflammation can contribute to the development of various diseases. This study aimed to discover anti-inflammatory metabolites from Penicillium bialowiezense. Seven spiroditerpenoids, including two new compounds, breviones P and Q (1 and 2), were isolated and characterized by various spectroscopic and spectrometric methods. All isolated compounds were initially tested for their inhibitory effects against lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages. Of these, brevione A (3) exhibited this activity with a half-maximal inhibitory concentration value of 9.5 μM. Further mechanistic studies demonstrated that 3 could suppress the expression of pro-inflammatory cytokines and mediators, such as NO, prostaglandin E, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12 by inhibiting the activation of nuclear factor-kappa B and c-Jun N-terminal kinase.
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http://dx.doi.org/10.1016/j.bioorg.2021.105012DOI Listing
August 2021

Chemical Constituents of the Egg Cases of (Mantidis ootheca) with Intracellular Reactive Oxygen Species Scavenging Activity.

Biomolecules 2021 04 10;11(4). Epub 2021 Apr 10.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine (KIOM), Naju 58245, Korea.

As a traditional medicine with potential antioxidant effects, egg cases (Mantidis ootheca) are a potential source of new bioactive substances. Herein, three new -acetyldopamine derivatives, namely, (+)-tenoderin A (), (-)-tenoderin A (), and tenoderin B (), along with thirteen known compounds (-), were isolated from a 70% EtOH extract of . egg cases. Compound was isolated as a racemic mixture, and two enantiomers ( and ) were successfully separated by chiral-phase preparative HPLC. The chemical structures of the new compounds were established by NMR spectroscopy and high-resolution electrospray ionization mass spectrometry, and the absolute configurations of enantiomers and were determined by electronic circular dichroism spectroscopy. All the new compounds exhibited antioxidant activities with IC values of 19.45-81.98 μM, as evaluated using free-radical scavenging assays, with the highest activity observed for compound . In addition, compounds , , and exhibited inhibitory activities on intracellular reactive oxygen species generation.
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http://dx.doi.org/10.3390/biom11040556DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8068885PMC
April 2021

Cicadidae Periostracum Attenuates Atopic Dermatitis Symptoms and Pathology via the Regulation of NLRP3 Inflammasome Activation.

Oxid Med Cell Longev 2021 13;2021:8878153. Epub 2021 Jan 13.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, 111 Geonjae-ro, Naju-si 58245, Republic of Korea.

Atopic dermatitis (AD) is a multifactorial inflammatory skin disease of complex etiology. Despite its increasing prevalence, treatment for AD is still limited. Crude drugs, including herbal extracts or natural resources, are being used to treat AD symptoms, with minimum side effects. Cicadidae Periostracum (CP), derived from the slough of insects belonging to the family Cicadidae, is a commonly used crude drug in traditional Asian medicine to treat/control epilepsy, shock, and edema. However, the effect of CP on AD-like skin lesions is unknown. In this study, we examined the effect of a CP water extract on AD disease development , using a house dust mite-induced AD mouse model, and , using HaCaT keratinocytes and a 3D human skin equivalent system. Importantly, CP administration alleviated house dust mite-induced AD-like symptoms, suggested by the quantified dermatitis scores, animal scratching behaviors, skin moisture retention capacity, and skin lesion and ear thickness. Furthermore, histopathological analysis demonstrated that CP decreased intralesional mast cell infiltration. In addition, CP treatments decreased the systemic levels of immunoglobulin E, histamine, and thymic stromal lymphopoietin (TSLP) and the local mRNA expression of TSLP and several Th1/Th2 cytokines. Our data suggest that these effects were mediated by the inhibition of nucleotide-binding oligomerization domain-like receptor protein 3 (NLRP3) inflammasome activation. and CP treatments resulted in the downregulation of inflammasome components, such as ASC and cleaved caspase-1, as well as related mediators such as IL-1 and reactive oxygen species. Collectively, our results suggest that CP is a potential therapeutic agent for AD, controlling inflammatory responses through the suppression of NLRP3 inflammasome activation.
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http://dx.doi.org/10.1155/2021/8878153DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7817262PMC
September 2021

Therapeutic Effects of Licorice and Dried Ginger Decoction on Activity-Based Anorexia in BALB/c AnNCrl Mice.

Front Pharmacol 2020 8;11:594706. Epub 2020 Dec 8.

Department of Oriental Medicine, College of Oriental Medicine, Dongshin University, Naju, South Korea.

Licorice and dried ginger decoction (Gancao-ganjiang-tang, LGD) is used for nausea and anorexia, accompanied by excessive sweating in Traditional Chinese Medicine. Herein, we investigated the therapeutic effects of LGD using the activity-based anorexia (ABA) in a mouse model. Six-week-old female BALB/c AnNCrl mice were orally administered LGD, water, licorice decoction, dried ginger decoction, or chronic olanzapine, and their survival, body weight, food intake, and wheel activity were compared in ABA. Additionally, dopamine concentration in brain tissues was evaluated. LGD significantly reduced the number of ABA mice reaching the drop-out criterion of fatal body weight loss. However, LGD showed no significant effects on food intake and wheel activity. We found that in the LGD group the rise of the light phase activity rate inhibited body weight loss. Licorice or dried ginger alone did not improve survival rates, they only showed longer survival periods than chronic olanzapine when combined. In addition, LGD increased the dopamine concentration in the brain. The results from the present study showed that LGD improves the survival of ABA mice and its mechanism of action might be related to the alteration of dopamine concentration in the brain.
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http://dx.doi.org/10.3389/fphar.2020.594706DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7845735PMC
December 2020

Chemical Constituents from the Aerial Parts of and Their Protective Activities on Glutamate-Induced HT22 Cell Death.

J Nat Prod 2020 10 29;83(10):3149-3155. Epub 2020 Sep 29.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine (KIOM), Naju 58245, Republic of Korea.

A new phenolic glucoside, (7,9)-3-hydroxyavenalumic acid-3--[6'--()-caffeoyl]-β-d-glucopyranoside (), and three new acetylated flavone glycosides, acacetin-7--[β-d-glucopyranosyl(1″″→2″)-4‴--acetyl-α-l-rhamnopyranosyl(1‴→6″)]-β-d-glucopyranoside (), acacetin-7--[6″″--acetylβ-d-glucopyranosyl(1″″→2″)-3‴--acetyl-α-l-rhamnopyranosyl(1‴→6″)]-β-d-glucopyranoside (), and acacetin-7--[3″″,6″″-di--acetylβ-d-glucopyranosyl(1″″→2″)-4‴--acetyl-α-l-rhamnopyranosyl(1‴→6″)]-β-d-glucopyranoside (), as well as 34 known compounds (, , , and -) were isolated from the aerial parts of . The chemical structures of the new compounds were determined by spectroscopic/spectrometric data interpretation using NMR and HRESIMS. The neuroprotective effect of the isolated compounds was evaluated by a cell viability assay on HT22 murine hippocampal neuronal cells. Among them, 23 compounds, including new substances and , exhibited neuroprotective effects against glutamate-induced HT22 cell death. In particular, compounds , , , , , , , and presented potent neuroprotective effects with EC values of 1.5-8.3 μM.
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http://dx.doi.org/10.1021/acs.jnatprod.0c00756DOI Listing
October 2020

Pharmacological Effects of against Gastritis Using a Network Pharmacology Approach.

Biomolecules 2020 09 9;10(9). Epub 2020 Sep 9.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, 111 Geonjae-ro, Jeollanam-do 58245, Korea.

is used as a Korean traditional medicine to treat gastric diseases. However, the active ingredients and pharmacological targets of are unknown. In this study, we aimed to reveal the pharmacological effects of on gastritis by combining a mice model and a network pharmacology method. The macrophage and gastritis-induced models were used to evaluate the pharmacological effects of . The results show that relieved mucosal damage induced by HCl/EtOH in vivo. Network analysis identified 99 components in ; six components were selected through systematic screening, and five components were linked to 45 gastritis-related genes. The main components were acacetin and luteolin, and the identified core genes were AKT serine/threonine kinase 1 (AKT1), nuclear factor kappa B inhibitor alpha (NFKBIA), and mitogen-activated protein kinase-3 (MAPK3) etc. in this network. The network of components, target genes, protein-protein interactions, and the Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway was closely connected with chemokines and with phosphoinositide 3-kinase-Akt (PI3K/AKT), tumor-necrosis-factor alpha (TNFα), mitogen-activated protein kinase, nuclear factor kappa B, and Toll-like receptor (TLR) pathways. In conclusion, exerts gastro-protective effects through a multi-compound and multi-pathway regulatory network and holds potential for treating inflammatory gastric diseases.
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http://dx.doi.org/10.3390/biom10091298DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7565599PMC
September 2020

Anti-inflammatory Metabolites from .

J Nat Prod 2020 04 12;83(4):881-887. Epub 2020 Mar 12.

Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea.

Twelve metabolites were obtained from the culture media of , including a new furan derivative, methyl succinyl Sumiki's acid (), and two new atropisomers of the previously reported bis-naphtho-γ-pyrones, (a)-asperpyrone A and (a)-fonsecinone A ( and ). The structures were elucidated by spectroscopic, chemical, and chiroptical techniques. Compounds and inhibited nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Compound was found to inhibit nuclear factor-kappa B and c-Jun N-terminal kinase activation, in turn suppressing pro-inflammatory mediators and cytokines including nitric oxide, prostaglandin E, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12.
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http://dx.doi.org/10.1021/acs.jnatprod.9b00560DOI Listing
April 2020

Chemical Constituents of the Leaves of Butterbur () and Their Anti-Inflammatory Effects.

Biomolecules 2019 11 29;9(12). Epub 2019 Nov 29.

Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, Korea.

Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur () along with six known compounds. The chemical structures of lignans and were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound in RAW264.7 cells. Furthermore, compounds and exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.
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http://dx.doi.org/10.3390/biom9120806DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6995602PMC
November 2019

Cicadidae Periostracum, the Cast-Off Skin of Cicada, Protects Dopaminergic Neurons in a Model of Parkinson's Disease.

Oxid Med Cell Longev 2019 24;2019:5797512. Epub 2019 Oct 24.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, 111 Geonjae-ro, Naju-si, Jeollanam-do 58245, Republic of Korea.

Parkinson's disease (PD) is characterized by dopaminergic neuronal loss in the substantia nigra pars compacta (SNPC) and the striatum. Nuclear receptor-related 1 protein (Nurr1) is a nuclear hormone receptor implicated in limiting mitochondrial dysfunction, apoptosis, and inflammation in the central nervous system and protecting dopaminergic neurons and a promising therapeutic target for PD. Cicadidae Periostracum (CP), the cast-off skin of Fabricius, has been used in traditional medicine for its many clinical pharmacological effects, including the treatment of psychological symptoms in PD. However, scientific evidence for the use of CP in neurodegenerative diseases, including PD, is lacking. Here, we investigated the protective effects of CP on 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine- (MPTP-) induced PD in mice and explored the underlying mechanisms of action, focusing on Nurr1. CP increased the expression levels of Nurr1, tyrosine hydroxylase, DOPA decarboxylase, dopamine transporter, and vesicular monoamine transporter 2 via extracellular signal-regulated kinase phosphorylation in differentiated PC12 cells and the mouse SNPC. In MPTP-induced PD, CP promoted recovery from movement impairments. CP prevented dopamine depletion and protected against dopaminergic neuronal degradation via mitochondria-mediated apoptotic proteins such as B-cell lymphoma 2 (Bcl-2), Bcl-2-associated X, cytochrome c, and cleaved caspase-9 and caspase-3 by inhibiting MPTP-induced neuroinflammatory cytokines, inducible nitric oxide synthase, cyclooxygenase 2, and glial/microglial activation. Moreover, CP inhibited lipopolysaccharide-induced neuroinflammatory cytokines and response levels and glial/microglial activation in BV2 microglia and the mouse brain. Our findings suggest that CP might contribute to neuroprotective signaling by regulating neurotrophic factors primarily via Nurr1 signaling, neuroinflammation, and mitochondria-mediated apoptosis.
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http://dx.doi.org/10.1155/2019/5797512DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6854990PMC
April 2020

Batryticatus Bombyx Protects Dopaminergic Neurons Against MPTP-Induced Neurotoxicity by Inhibiting Oxidative Damage.

Antioxidants (Basel) 2019 Nov 21;8(12). Epub 2019 Nov 21.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, 111 Geonjae-ro, Naju-si 58245, Korea.

Oxidative stress plays an important role in the degeneration of dopaminergic neurons in Parkinson's disease (PD). Altered redox homeostasis in neurons interferes with several biological processes, ultimately leading to neuronal death. Oxidative damage has been identified as one of the principal mechanisms underlying the progression of PD. Several studies highlight the key role of superoxide radicals in inducing neuronal toxicity. Batryticatus Bombyx (BB), the dried larva of L. infected by (Bals.) Vuill., has been used in traditional medicine for its various pharmacological effects. In the present study, BB showed a beneficial effect on 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity by directly targeting dopaminergic neurons. Treatment with BB improved behavioral impairments, protected dopaminergic neurons, and maintained dopamine levels in PD mouse models. Here, we investigated the protective effects of BB on MPTP-induced PD in mice and explored the underlying mechanisms of action, focusing on oxidative signaling. In MPTP-induced PD, BB promoted recovery from impaired movement, prevented dopamine depletion, and protected against dopaminergic neuronal degradation in the substantia nigra pars compacta (SNpc) or the striatum (ST). Moreover, BB upregulated mediators of antioxidative response such as superoxidase dismutase (SOD), catalase (CAT), glutathione (GSH), Heme oxygenase 1 (HO-1), and NAD(P)H (nicotinamide adenine dinucleotide phosphate) dehydrogenase (NQO1). Thus, treatment with BB reduced the oxidative stress, improved behavioral impairments, and protected against dopamine depletion in MPTP-induced toxicity.
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http://dx.doi.org/10.3390/antiox8120574DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943627PMC
November 2019

-Derived Drimane Sesquiterpenoids That Inhibit Osteoclast Differentiation.

J Nat Prod 2019 10 10;82(10):2835-2841. Epub 2019 Oct 10.

Laboratory Animal Resource Center , Korea Research Institute of Bioscience and Biotechnology , Cheongju 28116 , Republic of Korea.

The presence of excessive osteoclasts is a major factor in skeletal diseases. The present study aimed to discover osteoclast differentiation inhibitors from the basidiomycete . Seven new drimane sesquiterpenoids (-) and 7-ketoisodrimenin-5-ene () were obtained and characterized by various spectroscopic methods. The isolated compounds were evaluated for their inhibitory effects against receptor activator of nuclear factor-kappa-B ligand-induced osteoclastogenesis in mouse bone marrow macrophages. Compounds , , and showed potent activities with IC values of 1.6, 0.9, and 2.1 μM, respectively, while , , and exhibited relatively weak activities with IC values of 10.7, 10.1, and 8.5 μM, respectively.
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http://dx.doi.org/10.1021/acs.jnatprod.9b00559DOI Listing
October 2019

Furanocoumarins from the Roots of with Inhibitory Activity against Intracellular Reactive Oxygen Species Accumulation.

J Nat Prod 2019 09 29;82(9):2601-2607. Epub 2019 Aug 29.

College of Pharmacy, Graduate School of Pharmaceutical Sciences , Ewha Womans University , Seoul 03760 , Korea.

Five new furanocoumarins, dahuribirin H (), dahuribirin I (), (2')-(+)-5-(2'-hydroxy-3'-methylbut-3'-enyloxy)-8-(3''-methylbut-2″-enyloxy)psoralen (), (2')-(+)-5-(2',3'-epoxy-3'-methylbutoxy)-8-(3″-methylbut-2″-enyloxy)psoralen (), and 5-methoxy-8-(()-4'-(3″-methylbutanoate)-3'-methylbut-2'-enyloxy)psoralen (), along with 15 known compounds (-), were isolated from the roots of . The structures of the new compounds were elucidated by spectroscopic analysis, along with electronic circular dichroism calculations and Mosher ester analysis. Compounds , , , , and reduced HO-induced cell death in HepG2 cells and attenuated reactive oxygen species (ROS) formation without showing cytotoxicity, suggesting that these compounds might have cytoprotective effects against HO-induced oxidative damage via ROS scavenging activities.
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http://dx.doi.org/10.1021/acs.jnatprod.9b00547DOI Listing
September 2019

Identification of Two New Phenanthrenes from Dendrobii Herba and Their Cytotoxicity towards Human Hypopharynx Squamous Carcinoma Cell (FaDu).

Molecules 2019 Jun 25;24(12). Epub 2019 Jun 25.

Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup-si, Jeollabuk-do 56212, Korea.

Two new phenanthrenes, (1,2)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1)-one () and 2,7-dihydroxy-phenanthrene-1,4-dione (), were isolated from the ethyl acetate-soluble fraction of Dendrobii Herba, together with seven known phenanthrenes (-), two bibenzyls (-), and a lignan (). Structures of and were elucidated by analyzing one-dimensional (1D) and two-dimensional (2D)-NMR and High-resolution electrospray ionization mass spectra (HR-ESI-MS) data. The absolute configuration of compound was confirmed by the circular dichroism (CD) spectroscopic method. In cytotoxicity assay using FaDu human hypopharynx squamous carcinoma cell line, compounds -, , , and showed activities, with IC values that ranged from 2.55 to 17.70 μM.
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http://dx.doi.org/10.3390/molecules24122339DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631096PMC
June 2019

Gentisyl Alcohol Inhibits Proliferation and Induces Apoptosis via Mitochondrial Dysfunction and Regulation of MAPK and PI3K/AKT Pathways in Epithelial Ovarian Cancer Cells.

Mar Drugs 2019 Jun 3;17(6). Epub 2019 Jun 3.

Department of Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Korea.

Ovarian cancer is one of the prevalent gynecological cancers occurring in women. In particular, the efficiency of standard therapeutic methods decreases when recurrence and chemoresistance ensue. To assist standard anti-cancer agents in the cure of ovarian cancer, development and application of new compounds such as small molecules or natural products are required. Gentisyl alcohol is one of the secondary metabolites that can be obtained by purification from bacteria or fungi and is known to have antibacterial, antifungal, antiviral, and anti-cancer effects. In the present study, we verified the effect of gentisyl alcohol derived from marine sp. on suppressing proliferation and inducing apoptosis via DNA fragmentation in human ovarian cancers cells (ES2 and OV90 cells). We also confirmed that there was an accumulation of sub-G1 cells and a loss of mitochondrial membrane potential with calcium dysregulation in gentisyl alcohol-treated ovarian cancer cells. Moreover, gentisyl alcohol up-regulated signal transduction of MAPK and PI3K/AKT pathways. Collectively, our results demonstrated the possibility of gentisyl alcohol as a novel therapeutic agent for human ovarian cancer.
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http://dx.doi.org/10.3390/md17060331DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6627157PMC
June 2019

Two-Week Repeated Oral Dose Toxicity Study of Mantidis Ootheca Water Extract in C57BL/6 Mice.

Evid Based Complement Alternat Med 2019 7;2019:6180236. Epub 2019 Apr 7.

Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, 111Geonjae-ro, Naju-si, Jeollanam-do 58245, Republic of Korea.

Mantidis Ootheca (MO), described as the ootheca of Serville, 1839, (Saussure, 1869), or (Thunberg, 1784) in Korean Herbal Pharmacopoeia, is an important herbal material that has been traditionally used for treating several medical conditions including renal failure, spermatorrhea, and pediatric enuresis in Korea. The present study investigated the potential subacute toxicity of MO water extract during a 2-week repeated oral administration of doses of 0, 50, 150, or 450 mg/kg/day to C57BL/6 male mice by gavage. The following parameters were examined during the study period: mortality, clinical signs, body weight, hematology, serum biochemistry, gross findings, organ weight, and histopathology. All the mice were euthanized at the end of the treatment period. No treatment-related changes in mortalities, clinical signs, body weight, gross finding, and organ weight change were detected after 14 days of oral MO extract administration. In addition, no meaningful MO extract treatment-related changes were observed in the hematological, serum biochemical, and histopathological parameters compared with the normal control group following treatment with doses of up to 450 mg/kg/day. Based on these findings, we concluded that treatment of mice with the water extract of MO did not result in significant toxicity and, therefore, it could be considered safe for further pharmacological studies.
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http://dx.doi.org/10.1155/2019/6180236DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6475539PMC
April 2019

Non-glycosidic iridoids from the roots of Patrinia scabra and their nitric oxide production inhibitory effects.

Arch Pharm Res 2019 Sep 5;42(9):766-772. Epub 2019 Feb 5.

Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul, 02447, Republic of Korea.

Phytochemical investigation on the 70% aqueous EtOH extract from the roots of Patrinia scabra led to the isolation and characterization of five new non-glycosidic iridoids, patriscabrins F-J (1-5), along with a known iridoid 11-ethoxyviburtinal (6). The structures of the new compounds 1-5 were determined by interpretation of spectroscopic data, particularly by 1D- and 2D-NMR and ECD studies. Thereafter, the isolates 1-6 were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. Of these, patriscabrin F (1) exhibited the most potent inhibitory effect with observed IC value of 14.1 μM. In addition, patriscabrin G (2) and 11-ethoxyviburtinal (6) showed IC values 24.6 and 35.5 μM, respectively.
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http://dx.doi.org/10.1007/s12272-019-01117-0DOI Listing
September 2019

Diversity and Ecology of Marine Algicolous Arthrinium Species as a Source of Bioactive Natural Products.

Mar Drugs 2018 Dec 14;16(12). Epub 2018 Dec 14.

Division of Environmental Science & Ecological Engineering, College of Life Sciences & Biotechnology, Korea University, Seoul 02841, Korea.

In our previous study, all Arthrinium isolates from Sargassum sp. showed high bioactivities, but studies on marine spp. are insufficient. In this study, a phylogenetic analysis of 28 Arthrinium isolates from seaweeds and egg masses of Arctoscopus japonicus was conducted using internal transcribed spacers, nuclear large subunit rDNA, β-tubulin, and translation elongation factor region sequences, and their bioactivities were investigated. They were analyzed as 15 species, and 11 of them were found to be new species. Most of the extracts exhibited radical-scavenging activity, and some showed antifungal activities, tyrosinase inhibition, and quorum sensing inhibition. It was implied that marine algicolous Arthrinium spp. support the regulation of reactive oxygen species in symbiotic algae and protect against pathogens and bacterial biofilm formation. The antioxidant from Arthrinium sp. 10 KUC21332 was separated by bioassay-guided isolation and identified to be gentisyl alcohol, and the antioxidant of KUC21221 was identical. These results demonstrate that many unexploited Arthrinium species still exist in marine environments and that they are a great source of bioactive compounds.
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http://dx.doi.org/10.3390/md16120508DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6315899PMC
December 2018

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages.

J Nat Prod 2018 07 22;81(7):1598-1603. Epub 2018 Jun 22.

Herbal Medicine Research Division , Korea Institute of Oriental Medicine , Daejeon 34054 , Republic of Korea.

Apios americana is an important food crop producing edible tubers with high nutritional and medicinal values and is widely cultivated in many countries. Despite its usefulness, research on its secondary metabolites and biological activities has been limited. In the present study, a new coumaronochromone, (2 R,3 S)-3,7,4'-trihydroxy-5-methoxycoumaronochromone (1), and two new isoflavone glucosides, 7,2',4'-trihydroxy-5-methoxyisoflavone-4'- O-β-d-glucopyranoside (3) and 5,7,4'-trihydroxyisoflavone-7- O-β-d-gentiotrioside (5), were isolated from the tubers of A. americana via chromatographic separation. Seventeen known compounds (2, 4, and 6-20) were also obtained from this plant part. The chemical structures of 1, 3, and 5 were determined by the interpretation of spectroscopic data. The absolute structure of the new compound 1 was established from experimental and calculated electronic circular dichroism spectra. This is the first study to determine the absolute configuration of a 3-hydroxycoumaronochromone derivative. The potential anti-inflammatory activity of the 20 isolates obtained was evaluated by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Among the isolates, seven compounds (1, 3, 6-8, 15, and 20) showed substantial inhibition of nitric oxide production in RAW 264.7 cells, with the most active being compound 1 (IC value of 0.38 ± 0.04 μM).
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http://dx.doi.org/10.1021/acs.jnatprod.8b00182DOI Listing
July 2018

Iridoids from the Roots of Patrinia scabra and Their Inhibitory Potential on LPS-Induced Nitric Oxide Production.

J Nat Prod 2018 06 25;81(6):1468-1473. Epub 2018 May 25.

Department of Life and Nanopharmaceutical Sciences, Graduate School , Kyung Hee University , Seoul 136-713 , Korea.

An activity-guided fractionation procedure of the 70% aqueous EtOH extract from the roots of Patrinia scabra led to the isolation and characterization of five new iridoids, patriscabrins A-E (1-5), along with 13 known compounds. The structures of 1-5 were determined by interpretation of spectroscopic data, particularly by 1D and 2D NMR, ECD, and VCD studies. Thereafter, isolates were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. Of these, the new iridoids 2 and 5 and the known lignan patrineolignan B (6) exhibited IC values of 14.7 to 17.8 μM.
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http://dx.doi.org/10.1021/acs.jnatprod.8b00229DOI Listing
June 2018

Antiviral Activities of Trichothecenes Isolated from Trichoderma albolutescens against Pepper Mottle Virus.

J Agric Food Chem 2017 May 19;65(21):4273-4279. Epub 2017 May 19.

Plant Virus GenBank, Department of Horticulture, Biotechnology and Landscape Architecture, Seoul Women's University , Seoul 01797, Republic of Korea.

A bioassay-guided isolation using a green fluorescence protein (GFP)-tagged pepper mottle virus (PepMoV-GFP) based leaf-disk method to obtain new antiviral agents led to the isolation of trichodermin, 1, and a new compound trichoderminol, 2, from EtOAc extract of Trichoderma albolutescens culture medium. The structures of compounds 1 and 2 were determined by MS and NMR experiments, and the absolute configurations of the compounds were established by experimental and calculated vibrational circular dichroism spectra. Compounds 1 and 2 were evaluated for their anti-PepMoV potential in systemic host plants, such as tobacco and pepper, by PepMoV-GFP based systemic host method. All compounds exhibited inactivation effects against PepMoV. Furthermore, compound 1 showed protective effects against PepMoV.
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http://dx.doi.org/10.1021/acs.jafc.7b01028DOI Listing
May 2017

Quassinoids isolated from Brucea javanica inhibit pepper mottle virus in pepper.

Virus Res 2017 01 26;227:49-56. Epub 2016 Sep 26.

Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul, 02841, Republic of Korea. Electronic address:

A green fluorescent protein (GFP)-tagged pepper mottle virus (PepMoV) based leaf-disc method and systemic host method were developed to identify antiviral agents. Preliminary experiments using a PepMoV-GFP based leaf-disc method led to the isolation of five quassinoids, including brusatol (1), bruceantin (2), brucein A (3), bruceantinol (4), and brucein B (5), from the CHOH extract of Brucea javanica. All isolated compounds exhibited inactivation effects in systemic host plants, and compounds 3 and 4 were potent, with a minimum inhibitory concentration of 10μM. Furthermore, compound 3 was found to have a protective effect at the tested concentration of 40μM.
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http://dx.doi.org/10.1016/j.virusres.2016.09.013DOI Listing
January 2017

A metabolomic approach to determine the geographical origins of Anemarrhena asphodeloides by using UPLC-QTOF MS.

J Pharm Biomed Anal 2014 Apr 8;92:47-52. Epub 2014 Jan 8.

Department of Biosystems and Biotechnology, Korea University, Seoul 136-713, Republic of Korea. Electronic address:

An ultraperformance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF MS) method was developed for metabolite profiling of Anemarrhena asphodeloides Bunge from two different geographical origins. In this study, the metabolite profile data obtained using UPLC-QTOF MS was subjected to multivariate statistical analyses, such as the principal component analysis and the hierarchical clustering analysis, to compare metabolite patterns among A. asphodeloides samples. Furthermore, a metabolite selection method known as significance analysis of microarrays (SAM) was applied to further select metabolites and to identify key constituents to efficiently distinguish between geographical origins. The UPLC-QTOF MS analysis successfully classified 21 samples into two distinct groups according to their geographical origins. The validation method used to assess the analytical stability and accuracy of these data is also described. These results suggest that this proposed method is reliable, accurate, and effective for geographic classification of A. asphodeloides, thus guiding its proper use for therapeutic purposes.
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http://dx.doi.org/10.1016/j.jpba.2013.12.040DOI Listing
April 2014
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