Publications by authors named "Toshihiro Murata"

60 Publications

Evaluation of Mongolian compound library for potential antimalarial and anti-Toxoplasma agents.

Parasitol Int 2021 Jul 22:102424. Epub 2021 Jul 22.

National Research Center for Protozoan Diseases, Obihiro University of Agriculture and Veterinary Medicine, Hokkaido 080-8555, Japan. Electronic address:

179 compounds in a Mongolian compound library were investigated for their inhibitory effect on the in vitro growth of Plasmodium falciparum and Toxoplasma gondii. Among these compounds, brachangobinan A at a half-maximal inhibition concentration (IC) of 2.62 μM and a selectivity index (SI) of 27.91; 2-(2'-hydroxy-5'-O-methylphenyl)-5-(2″,5″-dihydroxyphenyl)oxazole (IC 3.58 μM and SI 24.66); chrysosplenetin (IC 3.78 μM and SI 15.26); 4,11-di-O-galloylbergenin (IC 3.87 μM and SI 13.38); and 2-(2',5'-dihydroxyphenyl)-5-(2″-hydroxyphenyl)oxazole (IC 6.94 μM and SI 11.48) were identified as potential inhibitors of P. falciparum multiplication. Additionally, tricin (IC 12.94 μM and SI >23.40) was identified as a potential inhibitor of T. gondii multiplication. Our findings represent a good starting point for developing novel antimalarial and anti-Toxoplasma therapeutics from Mongolian compounds.
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http://dx.doi.org/10.1016/j.parint.2021.102424DOI Listing
July 2021

Preoperative prognostic nutritional index predicts postoperative infectious complications and oncological outcomes after hepatectomy in intrahepatic cholangiocarcinoma.

BMC Cancer 2021 Jun 16;21(1):708. Epub 2021 Jun 16.

Department of Gastroenterological Surgery, Okayama University Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, 2-5-1 Shikata-cho, Okayama City, 700-8558, Japan.

Background: In the surgical treatment of intrahepatic cholangiocarcinoma (ICC), postoperative complications may be predictive of long-term survival. This study aimed to identify an immune-nutritional index (INI) that can be used for preoperative prediction of complications.

Patients And Methods: Multi-institutional data from 316 patients with ICC who had undergone surgical resection were retrospectively analysed, with a focus on various preoperative INIs.

Results: Severe complications (Clavien-Dindo grade III-V) were identified in 66 patients (20.8%), including Grade V complications in 7 patients (2.2%). Comparison of areas under the receiver operating characteristic curve (AUCs) among various INIs identified the prognostic nutritional index (PNI) as offering the highest predictive value for severe complications (AUC = 0.609, cut-off = 50, P = 0.008). Multivariate analysis revealed PNI <  50 (odds ratio [OR] = 2.22, P = 0.013), hilar lesion (OR = 2.46, P = 0.026), and long operation time (OR = 1.003, P = 0.029) as independent risk factors for severe complications. In comparing a high-PNI group (PNI ≥ 50, n = 142) and a low-PNI group (PNI <  50, n = 174), the low-PNI group showed higher rates of both major complications (27% vs. 13.4%; P = 0.003) and infectious complications (14.9% vs. 3.5%; P = 0.0021). Furthermore, median survival time and 1- and 5-year overall survival rates were 34.2 months and 77.4 and 33.8% in the low-PNI group, respectively, and 52.4 months and 89.3 and 47.5% in the high-PNI group, respectively (P = 0.0017).

Conclusion: Preoperative PNI appears useful as an INI correlating with postoperative severe complications and as a prognostic indicator for ICC.
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http://dx.doi.org/10.1186/s12885-021-08424-0DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8207701PMC
June 2021

Synthesis and evaluation of trypanocidal activity of derivatives of naturally occurring 2,5-diphenyloxazoles.

Bioorg Med Chem 2021 Jul 12;42:116253. Epub 2021 Jun 12.

Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.

African trypanosomiasis is a zoonotic protozoan disease affecting the nervous system. Various natural products reportedly exhibit trypanocidal activity. Naturally occurring 2,5-diphenyloxazoles present in Oxytropis lanata, and their derivatives, were synthesized. The trypanocidal activities of the synthesized compounds were evaluated against Trypanosoma brucei brucei, T. b. gambiense, T. b. rhodesiense, T. congolense, and T. evansi. Natural product 1 exhibited trypanocidal activity against all the species/subspecies of trypanosomes, exhibiting half-maximal inhibitory concentrations (IC) of 1.1-13.5 μM. Modification of the oxazole core improved the trypanocidal activity. The 1,3,4-oxadiazole (7) and 2,4-diphenyloxazole (9) analogs exhibited potency superior to that of 1. However, these compounds exhibited cytotoxicity in Madin-Darby bovine kidney cells. The O-methylated analog of 1 (12) was non-cytotoxic and exhibited selective trypanocidal activity against T. congolense (IC = 0.78 µM). Structure-activity relationship studies of the 2,5-diphenyloxazole analogs revealed aspects of the molecular structure critical for maintaining selective trypanocidal activity against T. congolense.
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http://dx.doi.org/10.1016/j.bmc.2021.116253DOI Listing
July 2021

Biological activity evaluations of chemical constituents derived from Mongolian medicinal forage plants and their applications in combating infectious diseases and addressing health problems in humans and livestock.

J Nat Med 2021 May 21. Epub 2021 May 21.

School of Engineering and Applied Sciences, National University of Mongolia, POB-617/46A, Ulaanbaatar, 14201, Mongolia.

Mongolian nomadic people possess traditional knowledge of wild plants that grow in their areas of habitation. Many of these are forage plants in nature and are consumed by livestock. However, these plants are known to have medicinal and/or toxic properties. To establish a scientific understanding of the plants, and in turn, offer sound knowledge on their applications and effective use, it is essential to collect data pertaining to the chemical constituents of each plant. Therefore, the first objective of this study was to identify and determine the structural constituents of the forage plants that were available to our research group. Furthermore, in an attempt to demonstrate the biological activities of the isolated chemical compounds, we focused on solving some of the social issues affecting Mongolian communities, including protozoan diseases affecting livestock, vectors of infectious diseases, and the general health of humans and their livestock. The results of the chemical constituents derived from Mongolian medicinal plants and their biological activities that were studied in the recent decade are also described herein.
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http://dx.doi.org/10.1007/s11418-021-01529-7DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8137442PMC
May 2021

Hyaluronidase and degranulation inhibitors from the edible roots of Oenanthe javanica including seric acids F and G that were obtained by heating.

Biosci Biotechnol Biochem 2021 Feb;85(2):369-377

Department of Pharmacognosy, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai, Japan.

Oenanthe javanica is a vegetable grown in East Asia and Australia in which the roots and aerial parts are boiled together to make certain traditional dishes. Nineteen compounds (1-19) were isolated from O. javanica roots and the chemical structures of 2 new norlignans were determined. The inhibitory effects of the compounds on hyaluronidase and degranulation in RBL-2H3 cells were evaluated to determine antiallergic and antiinflammation activities. Saponins (2-4) and the new norlignan seric acid G (12) were among the active compounds identified. Seric acid G (12), a methoxy derivative of seric acid F (11), was obtained as an interconverting mixture of 3:1 trans-cis isomers. Seric acids F and G (11, 12) were derived from seric acids C (10) and E, respectively, by decarboxylation and dehydration reactions that occurred during heating. It was confirmed by HPLC analysis that all eleven of the O. javanica cultivars contained seric acid C (10).
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http://dx.doi.org/10.1093/bbb/zbaa042DOI Listing
February 2021

Biological Properties, Bioactive Constituents, and Pharmacokinetics of Some spp. and Capsaicinoids.

Int J Mol Sci 2020 Jul 22;21(15). Epub 2020 Jul 22.

Department of Medical Microbiology and Immunology, Faculty of Medicine, Assiut University, Assiut 71515, Egypt.

Pepper originated from the genus, which is recognized as one of the most predominant and globally distributed genera of the Solanaceae family. It is a diverse genus, consisting of more than 31 different species including five domesticated species, , , , , and Pepper is the most widely used spice in the world and is highly valued due to its pungency and unique flavor. Pepper is a good source of provitamin A; vitamins E and C; carotenoids; and phenolic compounds such as capsaicinoids, luteolin, and quercetin. All of these compounds are associated with their antioxidant as well as other biological activities. Interestingly, fruits have been used as food additives in the treatment of toothache, parasitic infections, coughs, wound healing, sore throat, and rheumatism. Moreover, it possesses antimicrobial, antiseptic, anticancer, counterirritant, appetite stimulator, antioxidant, and immunomodulator activities. Capsaicin and creams are accessible in numerous ways and have been utilized in HIV-linked neuropathy and intractable pain.
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http://dx.doi.org/10.3390/ijms21155179DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7432674PMC
July 2020

Isolation and evaluation of trypanocidal activity of sesquiterpenoids, flavonoids, and lignans in Artemisia sieversiana collected in Mongolia.

J Nat Med 2020 Sep 3;74(4):750-757. Epub 2020 Jul 3.

National University of Mongolia, Ulaanbaatar, Mongolia.

Artemisia sieversiana is an annual herbaceous plant distributed throughout Central and East Eurasia and is regarded as an undesirable forage plant in Mongolia. It affects livestock, so information about its chemical composition is needed. We isolated three new sesquiterpenoids (1-3) and known compounds from A. sieversiana and investigated their activities. The absolute configuration of 1 was established using single-crystal X-ray diffraction crystallography, and its configuration differed from those of reported compounds with similar structures. Two additional new sesquiterpenoids (2 and 3) with similar structures were identified, and their configurations were determined. The trypanocidal activities of the isolated compounds (1-18) against Trypanosoma congolense and the pathogen responsible for fatal trypanosomosis in animals were estimated. Flavonoids and lignans were identified as active compounds with IC values ranging from 2.9 to 90.2 µM.
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http://dx.doi.org/10.1007/s11418-020-01429-2DOI Listing
September 2020

Saxifraga spinulosa-Derived Components Rapidly Inactivate Multiple Viruses Including SARS-CoV-2.

Viruses 2020 06 28;12(7). Epub 2020 Jun 28.

Department of Veterinary Medicine, Obihiro University of Agriculture and Veterinary Medicine, 2-11 Inada, Obihiro, Hokkaido 080-8555, Japan.

Novel severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), influenza A virus (IAV), and norovirus (NV) are highly contagious pathogens that threaten human health. Here we focused on the antiviral potential of the medicinal herb, Saxifraga spinulosa (SS). Water-soluble extracts of SS were prepared, and their virus-inactivating activity was evaluated against the human virus pathogens SARS-CoV-2 and IAV; we also examined virucidal activity against feline calicivirus and murine norovirus, which are surrogates for human NV. Among our findings, we found that SS-derived gallocatechin gallate compounds were capable of inactivating all viruses tested. Interestingly, a pyrogallol-enriched fraction (Fr 1C) inactivated all viruses more rapidly and effectively than did any of the component compounds used alone. We found that 25 µg/mL of Fr 1C inactivated >99.6% of SARS-CoV-2 within 10 s (reduction of ≥2.33 log TCID/mL). Fr 1C resulted in the disruption of viral genomes and proteins as determined by gel electrophoresis, electron microscopy, and reverse transcription-PCR. Taken together, our results reveal the potential of Fr 1C for development as a novel antiviral disinfectant.
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http://dx.doi.org/10.3390/v12070699DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7411974PMC
June 2020

Bioactive Compounds, Pharmacological Actions, and Pharmacokinetics of Wormwood ().

Antibiotics (Basel) 2020 Jun 23;9(6). Epub 2020 Jun 23.

Área Académica de Medicina Veterinaria y Zootecnia, Instituto de Ciencias Agropecuarias, Universidad Autónoma del Estado de Hidalgo, Rancho Universitario Av. Universidad km 1, EX-Hda de Aquetzalpa, 43600 Tulancingo, Hgo, Mexico.

Plants have been used since ancient times to cure certain infectious diseases, and some of them are now standard treatments for several diseases. Due to the side effects and resistance of pathogenic microorganisms to antibiotics and most drugs on the market, a great deal of attention has been paid to extracts and biologically active compounds isolated from plant species used in herbal medicine. is an important perennial shrubby plant that has been widely used for the treatment of several ailments. Traditionally, has always been of pharmaceutical and botanical importance and used to manage several disorders including hepatocyte enlargement, hepatitis, gastritis, jaundice, wound healing, splenomegaly, dyspepsia, indigestion, flatulence, gastric pain, anemia, and anorexia. It has also been documented to possess antioxidant, antifungal, antimicrobial, anthelmintic, anti-ulcer, anticarcinogenic, hepatoprotective, neuroprotective, antidepressant, analgesic, immunomodulatory, and cytotoxic activity. Long-term use of A. absinthium essential oil may cause toxic and mental disorders in humans with clinical manifestations including convulsions, sleeplessness, and hallucinations. Combination chemotherapies of artemisia extract or its isolated active constituents with the currently available antibabesial or anti-malarial drugs are now documented to relieve malaria and piroplasmosis infections. The current review examines the phytoconstituents, toxic and biological activities of
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http://dx.doi.org/10.3390/antibiotics9060353DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7345338PMC
June 2020

A new hexenoic acid glycoside with cytotoxic activity from the leaves of .

Nat Prod Res 2020 May 13:1-6. Epub 2020 May 13.

Pharmacognosy Department, Tohoku Medical and Pharmaceutical University, Sendai, Japan.

A new hexenoic acid glycoside () together with known compounds, flavonol glycosides (-), iridoid glycoside (), megastigmane glycoside (), and amino acid () were isolated from the leaves of . by resin column chromatography and preparative HPLC. Their structures were determined based on spectroscopic analysis, including HRFABMS and NMR (H and C, H-H COSY, HMQC, and HMBC) data. All compounds tested for cytotoxicity were active (IC < 50 μM) with IC values ranging from 1.97 to 32.85 μM against human colon adenocarcinoma cell line, compared to etoposide (IC 1.19 μM).
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http://dx.doi.org/10.1080/14786419.2020.1765345DOI Listing
May 2020

Hyaluronidase inhibitory saponins and a trypanocidal isoflavonoid from the aerial parts of Oxytropis lanata.

Fitoterapia 2020 Sep 6;145:104608. Epub 2020 May 6.

Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.

A chemical examination of an extract from the aerial part of Oxytropis lanata led to the isolation and identification of 36 compounds, including saponins, isoflavonoids, oxazoles, and glycosides. The three among them were previously unreported oleanane-type saponins. In trypanocidal screening, 5,7,4'-trihydroxyisoflavone showed inhibitory activity against Trypanosoma congolense (IC = 10.5 μM), the causative agent of African trypanosomosis in animals; this activity was similar to that of active compounds from the roots of this plant. O. lanata is known to be a traditional medicinal plant in Mongolia for the treatment of inflammatory diseases. The anti-hyaluronidase effect of saponins 3, 5, 8, and 9, (IC = 0.15-0.22 mM) was stronger than that of sodium cromoglicate, which was used as a reference drug (IC = 0.37 mM). The chemical structures of the new saponins were determined based on HRFABMS, H and C NMR, H-H COSY, HMQC, HMBC, and ROESY spectroscopic data along with chemical procedures.
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http://dx.doi.org/10.1016/j.fitote.2020.104608DOI Listing
September 2020

Constituents of the Fruiting Body of Poisonous Mushroom Omphalotus japonicus.

Chem Pharm Bull (Tokyo) 2020 ;68(5):436-442

The United Graduate School of Agricultural Science, Iwate University.

Six new sesquiterpenes, tsukiyols A-C, neoilludin C, and 4-O-methylneoilludins A and B, were isolated from the fruiting body of Omphalotus japonicus (Kawam.) Kirchm. & O. K. Mill. Additionally, six known compounds, illudin S, neoilludins A-B, 5-hydroxydichomitol, ergosterolperoxide, and 3β,5α,9α-trihydroxyergosta-7,22-diene-6-one, were also obtained. Their chemical structures were determined with MS, IR, and NMR spectra and the absolute configurations of neoilludins A-C, 4-O-methylneoilludins A, and B were determined with electronic circular dichroism (ECD). Illudin S and 3β,5α,9α-trihydroxyergosta-7,22-diene-6-one showed cytotoxicity against human acute promyelocytic leukemia HL60 cells. Illudin S, 4-O-methylneoilludin A, B, and tsukiyol C showed growth-restoring activity against mutant yeast via Ca-signal transduction.
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http://dx.doi.org/10.1248/cpb.c19-01009DOI Listing
January 2021

Inhibitory activities of phenylpropanoids from Lycopus lucidus on amyloid aggregation related to Alzheimer's disease and type 2 diabetes.

J Nat Med 2020 Jun 26;74(3):579-583. Epub 2020 Mar 26.

Faculty of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8572, Japan.

The number of patients with Alzheimer's disease (AD) and type 2 diabetes (T2D) is increasing rapidly, and thus more research has been focused on the relationship between these two age-related chronic diseases. According to the amyloid hypothesis, prevention of the aggregation of amyloid β (Aβ) and human islet amyloid polypeptide (hIAPP) is a promising strategy for AD and T2D. In this study, thioflavin-T assay and transmission electron microscopy were performed to evaluate the inhibitory effect of three phenylpropanoids isolated from Lycopus lucidus-schizotenuin A and lycopic acids A and B-on both Aβ and hIAPP fibrillization. All tested compounds exhibited similarly strong inhibitory activity toward amyloid aggregation. These results suggested that catechol moieties play important roles in the inhibition of amyloid plaque formation.
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http://dx.doi.org/10.1007/s11418-020-01398-6DOI Listing
June 2020

Indirubin promotes adipocyte differentiation and reduces lipid accumulation in 3T3‑L1 cells via peroxisome proliferator‑activated receptor γ activation.

Mol Med Rep 2020 Mar 16;21(3):1552-1560. Epub 2020 Jan 16.

Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, Miyagi 981‑8558, Japan.

The peroxisome proliferator‑activated receptor γ (PPARγ) plays an important role in insulin sensitivity and adipocyte differentiation. It is known as ligand‑receptor that improves insulin sensitivity in type 2 diabetes mellitus. Several kinds of indigo plant have been already used to treat diabetes in oriental traditional medicine, but its mechanism has not been clarified yet. To investigate the effect of indirubin, which is a component of Polygonum tinctorium on the cell differentiation and adipprocess in 3T3‑L1 cells, 3T3‑L1 cells were cultured to determine the effect of cell differentiation and glucose uptake with indirubin. As a result, Indirubin compound enhanced adipocyte differentiation in 3T3‑L1 cells similar to rosiglitazone. This effect was terminated by cotreatment with GW9662, a PPARγ antagonist. In mature 3T3‑L1 adipocytes, the lipid droplet size and accumulation were reduced by this compound. The basal and insulin‑stimulated glucose uptakes were also significantly increased. In addition, indirubin treatment significantly enhanced estrogen level by 1.64‑fold with mature adipocytes which can be attributed to its aromatase activity. Conclutionaly, this finding suggested that indirubin is a potential anti‑diabetic compound for type 2 diabetes mellitus by promoting adipocyte differentiation and glucose uptake via PPARγ.
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http://dx.doi.org/10.3892/mmr.2020.10946DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7003043PMC
March 2020

[Complete Remission of Advanced Gastric Cancer with Tumor Embolism in the Right Gastric Vein Treated with Radical Resection after Chemotherapy].

Gan To Kagaku Ryoho 2019 Apr;46(4):823-825

Dept. of Surgery, Onomichi Municipal Hospital.

A 74-year-old man presented to our hospital with the chief complaint of epigastric pain; upper gastrointestinal endoscopy revealed a 7-cm-sized type 3 gastric cancer in the lesser curvature of the lower part of the stomach. Abdominal contrast computed tomography revealed a tumor embolus in the right gastric vein; the preoperative diagnosis was cT4a(SE) N3aH0P0M0, cStage ⅢC. Because the cancer could spread during surgical manipulation, performing a safe radical resection was difficult; therefore, we decided to initiate chemotherapy. The patient received 3 courses of trastuzumab plus CapeOX, which led to reduction of the primarylesion, peri-gastric lymph node, and right gastric vein tumor embolus. Partial remission was achieved after chemotherapy; therefore, distal gastrectomy, D2 lymph node dissection, and Roux-en-Y reconstruction were performed. Histopathological examination did not reveal viable tumor cells in the primarylesion, lymph nodes, or tumor embolus, and the histological effect was Grade 3. Currently, the patient is alive without relapse at 9 months post operation. Advanced gastric cancer accompanied with tumor embolism in the gastric vein is commonly observed in patients with liver metastasis and in those with severely progressed state of cancer; many of these patients have poor prognosis. Preoperative chemotherapymaybe effective in cases in which tumor embolism in the gastric vein is identified through preoperative diagnostic imaging.
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April 2019

Inhibitory Effects of Phenylpropanoid Derivatives from Oenanthe javanica on Antigen-Stimulated Degranulation in RBL-2H3 Cells.

J Nat Prod 2019 06 24;82(6):1518-1526. Epub 2019 May 24.

Department of Pharmacognosy , Tohoku Medical and Pharmaceutical University , Aoba-ku, Sendai 981-8558 , Japan.

Two diacyldaucic acids (1 and 2), an α,β-unsaturated γ-lactone-type lignan (3) and its derivatives (4-6), and 12 known compounds were isolated from a traditional East Asian vegetable, Oenanthe javanica. The absolute configuration of 1 was validated by obtaining (+)-osbeckic acid through acid hydrolysis. The absolute configurations of 3-5 were determined by comparing their experimental and computed ECD data. The conclusion was supported by applying the phenylglycine methyl ester method to 3. Compound 6 was obtained as an interconverting mixture of isomers in a 3:1 trans- cis ratio. Several water-soluble components (1, 3, and 6) showed concentration-dependent inhibitory effects on antigen-stimulated degranulation in RBL-2H3 cells without producing any direct cytotoxicity against RBL-2H3 or HeLa cells.
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http://dx.doi.org/10.1021/acs.jnatprod.8b01054DOI Listing
June 2019

Acylated Lignans Isolated from Brachanthemum gobicum and Their Trypanocidal Activity.

J Nat Prod 2019 04 21;82(4):774-784. Epub 2019 Mar 21.

Department of Pharmacognosy , Tohoku Medical and Pharmaceutical University , Aoba-ku, Sendai 981-8558 , Japan.

Eight isovaleryllignans (1-4 and 8-11), three isovalerylphenylpropanoids (5-7), three known lignans (12-14), and four known compounds were isolated from an extract of the aerial part of Brachanthemum gobicum. The structures of the isolated compounds were elucidated based on NMR and MS data analyses. The enantiomers of compounds 1-3, 5, 8, and 9 were isolated using chiral-phase HPLC, and the absolute configurations of 1a/1b-3a/3b, 5a/5b, 8a/8b, and 9a/9b were elucidated from their optical rotations and ECD spectra; the other lignans were assumed to be racemic or scalemic by chiral-phase HPLC analyses and optical rotation data. Some of the acylated lignans (racemic mixtures) (1-4, 8, 9, and 12-14) exhibited moderate inhibitory activities against Trypanosoma congolense, the causative agent of nagana disease in animals.
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http://dx.doi.org/10.1021/acs.jnatprod.8b00670DOI Listing
April 2019

Flavonoids isolated from the flowers of Pulsatilla flavescens and their anti-piroplasm activity.

J Nat Med 2019 Jun 7;73(3):633-640. Epub 2019 Mar 7.

School of Engineering and Applied Sciences, National University of Mongolia, P.O.B.-617/46A, Ulaanbaatar, 14201, Mongolia.

Pulsatilla species are known as "Yargui", and their flowers are traditionally used in Mongolia as a tonic and for the treatment of inflammatory diseases. By chemical investigation of P. flavescens flowers, 21 flavonoids, including a new chalcone C-glucoside, chalconaringenin 2'-O-β-D-glucopyranosyl-5'-β-D-glucopyranoside, and two new flavanone C-glucosides, (2R)- and (2S)-naringenin 8-β-D-glucopyranosyl-4'-O-β-D-glucopyranoside, were isolated. The absolute configurations of the seven flavanone glucosides were elucidated by ECD spectra. For the isolated compounds, inhibitory activity against Babesia caballi and Theileria equi, which cause fatal diseases in horses, was estimated. Although most of the isolated chalcone and flavanone derivatives did not show any anti-piroplasm activity, all the isolated flavone and flavonol derivatives showed moderate effects against B. caballi and/or T. equi.
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http://dx.doi.org/10.1007/s11418-019-01294-8DOI Listing
June 2019

[Bilateral Metastatic Lung Tumor with Different Primary Organs].

Kyobu Geka 2018 Jun;71(6):430-433

Department of Surgery, Onomichi Municipal Hospital, Onomichi, Japan.

A 72-year-old woman with a history of surgery for left breast cancer was found to have sigmoid colon cancer and solitary pulmonary tumor of left upper lobe. We diagnosed adenocarcinoma of the unknown origin by a transbronchial biopsy. We performed left upper segmentectomy and sigmoidectomy. Left pulmonary tumor was diagnosed metastatic lung tumor from breast cancer. A right pulmonary tumor was confirmed by chest computed tomography(CT) after sigmoidectomy. It was also considered to be metastasis from breast cancer and treated with vinorelbine ditartrate. Since no effect was observed by chemotherapy, tumor was surgically removed by wedge resection. Right pulmonary tumor was pathologically diagnosed as metastasis from sigmoid colon cancer. In suspicious case of pulmonary metastases from double cancer, the possibility of different lesions from different primary site should be kept in mind.
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June 2018

[Pulmonary Pleomorphic Carcinoma Relapsed after Surgery Surviving Long-term by Chemotherapy and Nivolumab].

Kyobu Geka 2018 May;71(5):329-333

Department of Surgery, Onomichi Municipal Hospital, Onomichi, Japan.

A 60'-year-old man was referred to our hospital because of nodular shadow found at mass screening. We diagnosed the tumor as non-small cell lung cancer by transbronchial biopsy. Chest computed tomography showed a tumor shadow of 3 cm in diameter with cavity. Right middle lobectomy was performed and the pathological diagnosis was pleomorphic carcinoma of the lung. The tumor recurrence was found at 10 months after surgery, and was treated with cisplatin, docetaxel plus bevacizumab for 6 cycles. A complete remission was achieved, but regrowth at 5 months after chemotherapy was noted. The patient was treated with nivolumab following carboplatin, gemcitabine plus bevacizumab 3 cycles. A good partial response is continuing 2 years and 5 months after confirming recurrence.
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May 2018

A case of small intestinal neuroendocrine carcinoma diagnosed using double-balloon endoscopy with long-term survival.

Clin J Gastroenterol 2018 Jun 15;11(3):240-244. Epub 2018 Feb 15.

Department of Gastroenterology and Hepatology, Okayama University Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama, Japan.

Neuroendocrine neoplasms, including neuroendocrine tumors (NETs) and neuroendocrine carcinomas (NECs), are rare epithelial tumors with a predominant neuroendocrine differentiation. Compared with NETs, NECs have been reported to be rarer and have a poorer prognosis. We present a rare case of small bowel NEC diagnosed using double-balloon endoscopy (DBE) and the long-term survival accomplished via intensive therapy. DBE revealed an ulcerative tumor in the deep jejunum, and biopsy specimens showed large and highly dysplastic tumor cells; immuno-histological synaptophysin and chromogranin A tests were positive, and the Ki-67 index was more than 90%. Partial intestinal resection without complete lymph node dissection was performed and, postoperatively, chemotherapy was administered. The patient was observed for 3 years after chemotherapy, and complete remission was maintained.
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http://dx.doi.org/10.1007/s12328-018-0834-8DOI Listing
June 2018

Lanostane triterpenoids from Fomitopsis officinalis and their trypanocidal activity.

J Nat Med 2018 Mar 7;72(2):523-529. Epub 2018 Feb 7.

Department of Pharmacognosy, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai, 981-8558, Japan.

Fomitopsis officinalis is a medicinal fungus, known as 'Agarikon', and is used traditionally in the treatment of asthma and rheumatism in Mongolia. The investigation of the chemical constituents of F. officinalis led to the isolation of 4 new lanostane triterpenoids together with 4 known triterpenoids. Inhibitory activity against Trypanosoma congolense, which causes fatal diseases in animals including livestock, was estimated for the isolated compounds. Compounds 2-5 and 8 exhibited moderate inhibition activities with IC values ranging from 7.0-27.1 µM.
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http://dx.doi.org/10.1007/s11418-018-1182-1DOI Listing
March 2018

Flavonoid and Galloyl Glycosides Isolated from Saxifraga spinulosa and Their Antioxidative and Inhibitory Activities against Species That Cause Piroplasmosis.

J Nat Prod 2017 09 23;80(9):2416-2423. Epub 2017 Aug 23.

School of Engineering and Applied Sciences, National University of Mongolia , Ulaanbaatar 14201, Mongolia.

Eight new flavonoid-based 3'-O-β-d-glucopyranosides (1-8) and three new galloyl glucosides (9, 11, 12), were isolated from the aerial parts of Saxifraga spinulosa, along with 25 known compounds. The structures of the new compounds were elucidated by spectroscopic methods. Most of the isolated compounds exhibited potent DPPH radical-scavenging activities. Further, their inhibitory activities were evaluated against Babesia bovis, Babesia bigemina, Babesia caballi, and Theileria equi, protozoan parasites that cause piroplasmosis in livestock. The results indicated that several of these compounds showed growth-inhibitory effects on such organisms that cause piroplasmosis.
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http://dx.doi.org/10.1021/acs.jnatprod.7b00142DOI Listing
September 2017

Antioxidant Flavonols and Phenolic Compounds from Atraphaxis frutescens and Their Inhibitory Activities against Insect Phenoloxidase and Mushroom Tyrosinase.

J Nat Prod 2016 Dec 8;79(12):3065-3071. Epub 2016 Dec 8.

Department of Pharmacognosy, Tohoku Medical and Pharmaceutical University , 4-1 Komatsushima 4-chome, Aoba-ku, Sendai 981-8558, Japan.

Chemical investigation of the aerial parts of Atraphaxis frutescens resulted in the isolation of five 7-methoxyflavonols with pyrogallol B-ring moieties (1-5), a fisetinidol glucoside (13), and a benzyl glycoside (18), together with 26 known compounds including flavonoids, phenylpropanoid amides, anthraquinone glycosides, lignans, and a benzyl derivative. The principal chemical structural feature of the isolated compounds was either a pyrogallol or catechol B-ring moiety, and they showed potent 1,1-diphenyl-2-picrylhydrazyl radical scavenging activities. To assess the effects of these antioxidants on biological enzymes, their inhibitory effects against an insect phenoloxidase and a mushroom tyrosinase were evaluated. This study indicated that insect phenoloxidase was inhibited by phenylpropanoid amides and that mushroom tyrosinase was inhibited by the characteristic 7-methoxyflavonol 3-O-rhamnopyranosides.
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http://dx.doi.org/10.1021/acs.jnatprod.6b00720DOI Listing
December 2016

Trypanocidal Activity of 2,5-Diphenyloxazoles Isolated from the Roots of Oxytropis lanata.

J Nat Prod 2016 11 31;79(11):2933-2940. Epub 2016 Oct 31.

Department of Pharmacognosy, Tohoku Medical and Pharmaceutical University , 4-1 Komatsushima 4-chome, Aoba-ku, Sendai 981-8558, Japan.

Eleven 2,5-diphenyloxazole derivatives (1-11), together with six known isoflavonoid derivatives, were isolated from the roots of Oxytropis lanata. The 2,5-diphenyloxazole (1) obtained proved to be identical to a standard sample used as a scintillator and liquid laser dye. The other oxazole derivatives isolated were found to have one to four hydroxy and/or O-methyl groups in their phenyl rings. Seven of the oxazole derivatives obtained are new (3-9). The inhibitory activity of the isolated compounds was evaluated against Trypanosoma congolense, the causative agent of African trypanosomosis in animals. Oxazoles with di- and trihydroxy groups showed trypanocidal activity, and 2-(2',3'-dihydroxyphenyl)-5-(2″-hydroxyphenyl)oxazole (4) exhibited the most potent inhibitory activity (IC 1.0 μM).
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http://dx.doi.org/10.1021/acs.jnatprod.6b00778DOI Listing
November 2016

Abietane-type diterpenoids from the roots of Caryopteris mongolica and their cholinesterase inhibitory activities.

Phytochemistry 2016 Oct 10;130:152-8. Epub 2016 Jun 10.

School of Engineering and Applied Sciences, National University of Mongolia, POB-617, Ulaanbaatar-46A, 14201, Mongolia.

Eleven abietane-type diterpenoids and two known abietanes were isolated from the roots of Caryopteris mongolica, and their structures were characterized. The absolute configurations at C-5 and C-10 were determined from the NMR data, including from the nuclear Overhauser effect and CD spectra, and the absolute configuration of C-16 in the hydroxypropyl group was determined via a modified Mosher's method. Furthermore, the previously unknown absolute configuration of the C-15 of cyrtophyllone B was determined to be in an R-configuration using X-ray crystallography. To estimate the preventive effects of the isolates for neurodegenerative disease development, their inhibitory activities against acetylcholinesterase (AChE) from human erythrocytes and butyrylcholinesterase (BChE) from horse serum were evaluated.
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http://dx.doi.org/10.1016/j.phytochem.2016.05.011DOI Listing
October 2016

An antibacterial ortho-quinone diterpenoid and its derivatives from Caryopteris mongolica.

Bioorg Med Chem Lett 2015 Jun 24;25(12):2555-8. Epub 2015 Apr 24.

School of Engineering and Applied Sciences, National University of Mongolia, POB-617, Ulaanbaatar-46A, Mongolia.

To identify antibacterial components in traditional Mongolian medicinal plant Caryopteris mongolica, an ortho-quinone abietane caryopteron A (1) and three its derivatives caryopteron B-D (2-4) were isolated from the roots of the plant together with three known abietanes demethylcryptojaponol (5), 6α-hydroxydemethyl cryptojaponol (6), and 14-deoxycoleon U (7). The chemical structures of these abietane derivatives were elucidated on the basis of spectroscopic data. Compounds 1-4 had C-13 methylcyclopropane substructures, and 2-4 had a hexanedioic anhydride ring C instead of ortho-quinone in 1. The stereochemistry of these compound was assumed from NOE spectra and ECD Cotton effects. Compounds 1 and 5-7 showed antibacterial activities against the Gram-positive bacteria Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, and Micrococcus luteus, being 1 the more potent.
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http://dx.doi.org/10.1016/j.bmcl.2015.04.048DOI Listing
June 2015

Cholinesterase-inhibitory diterpenoids and chemical constituents from aerial parts of Caryopteris mongolica.

J Nat Med 2015 Oct 22;69(4):471-8. Epub 2015 Apr 22.

Department of Pharmacognosy, Tohoku Pharmaceutical University, 4-1 Komatsushima 4-chome, Aoba-ku, Sendai, 981-8558, Japan,

A diterpenoid diglucoside (12,19-di-O-β-D-glucopyranosyl-11-hydroxyabieta-8,11,13-triene-19-one), isoscutellarein 7-O-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranoside, isoscutellarein 7-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7-O-[6″-O-(p-E-coumaroyl)]-β-D-glucopyranoside, hypolaetin 7-O-[6″-O-(E-caffeoyl)]-β-D-glucopyranoside, and 15 known compounds were isolated from aerial parts of the Mongolian medicinal plant Caryopteris mongolica. The cholinesterase-inhibitory activities of the constituents were estimated. The abietane diterpenoids (12-O-demethylcryptojaponol and 6α-hydroxydemethylcryptojaponol) showed potent inhibitory activity against acetylcholinesterase from human erythrocytes and electric eel, and against butyrylcholinesterase from horse serum.
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http://dx.doi.org/10.1007/s11418-015-0908-6DOI Listing
October 2015

Ultrastructural analysis of an enterolith composed of deoxycholic acid.

Acta Med Okayama 2014 Dec;68(6):369-74

Department of Gastroenterology, Onomichi Municipal Hospital, Onomichi, Hiroshima 722-8503,

A 67-year-old Japanese man underwent enterotomy because of enterolith ileus. Component analysis by infrared spectroscopy revealed that the enterolith was composed of a high concentration of deoxycholic acid. We further analyzed and compared the ultrastructure of the enterolith and a commercially available powdered form of deoxycholic acid by means of scanning electron microscopy and energy dispersive X-ray spectroscopy. Energy dispersive X-ray spectroscopy analysis revealed that the ratios of carbon and oxygen in the enterolith were equal to those in the deoxycholic acid powder. Scanning electron microscopy analysis showed rectangular prism-shaped particles on the surface of the enterolith. This structure was similar to that of the deoxycholic acid powder. The surgically removed enterolith had a twisted and coiled appearance. Possible mechanisms underlying the formation of this unique form are discussed.
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http://dx.doi.org/10.18926/AMO/53026DOI Listing
December 2014

Clinical characteristics and treatment outcomes of nineteen Japanese patients with gastrointestinal bezoars.

Intern Med 2014 1;53(11):1099-105. Epub 2014 Jun 1.

Department of Gastroenterology and Hepatology, Okayama University Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Japan.

Objective: To analyze the clinical characteristics of patients with gastrointestinal bezoars and their response to therapy. Patients We retrospectively reviewed the cases of 19 patients diagnosed with gastrointestinal bezoars at the Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences or one of 15 collaborating institutions between December 2004 and August 2013. We investigated the epidemiology and etiology of the gastrointestinal bezoars by determining the gender, age at diagnosis, medical history, symptoms, complications, modalities used for diagnosis, treatments, outcomes and bezoar location, color and contents.

Results: There were 17 patients with gastric bezoars and two patients with small intestinal bezoars. All patients were 62 years of age or older, except for one case of a trichobezoar in a 10-year-old patient. Some of the patients had a history of surgery of any part of the gastrointestinal tract (n=5) and/or diabetes mellitus (n=2). The two patients with small intestinal bezoars required surgical removal in order to relieve ileus. Approximately one-half of the patients with gastric bezoars had ulcerations in the stomach (9/17 patients, 52.9%) and/or gastrointestinal bleeding (8/17, 47.1%). Endoscopic fragmentation was performed in 10 patients, whereas bezoar dissolution was achieved with a gastroprokinetic agent (n=1) and without any treatment (n=3) in the remaining cases.

Conclusion: As previously reported, elderly individuals with a positive history of surgery and/or diabetes mellitus were observed in this bezoar patient series. Gastric ulcers and gastrointestinal bleeding were frequently observed. The majority of patients underwent endoscopic fragmentation, while spontaneous resolution of the gastric bezoar was observed in several cases.
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http://dx.doi.org/10.2169/internalmedicine.53.2114DOI Listing
May 2015
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