Osamu Muraoka

Summary

Affiliation: Kinki University
Country: Japan

Publications

  1. ncbi request reprint Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity
    Osamu Muraoka
    School of Pharmaceutical Sciences, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 14:500-9. 2006
  2. ncbi request reprint Medicinal flowers. XXVII. New flavanone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-alpha inhibitors from everlasting, flowers of Helichrysum arenarium
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan
    Chem Pharm Bull (Tokyo) 57:361-7. 2009
  3. doi request reprint Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2
    Genzoh Tanabe
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 20:6321-34. 2012
  4. doi request reprint Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 66:39-48. 2012
  5. doi request reprint Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 68:561-6. 2014
  6. doi request reprint In silico design, synthesis and evaluation of 3'-O-benzylated analogs of salacinol, a potent α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine "Salacia"
    Genzoh Tanabe
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Chem Commun (Camb) 48:8646-8. 2012
  7. doi request reprint Anti-hyperlipidemic constituents from the bark of Shorea roxburghii
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 66:516-24. 2012
  8. doi request reprint New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora
    Saowanee Chaipech
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 66:486-92. 2012
  9. ncbi request reprint Bioactive constituents from chinese natural medicines. XXXVI. Four new acylated phenylethanoid oligoglycosides, kankanosides J1, J2, K1, and K2, from stems of Cistanche tubulosa
    Yingni Pan
    Pharmaceutical Research and Technology Institute, Kinki University, Higashi Osaka, Osaka, Japan
    Chem Pharm Bull (Tokyo) 58:575-8. 2010
  10. doi request reprint Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Food Chem 140:353-60. 2013

Collaborators

Detail Information

Publications56

  1. ncbi request reprint Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity
    Osamu Muraoka
    School of Pharmaceutical Sciences, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 14:500-9. 2006
    ..A practical synthetic route to 3 starting from D-xylose is also described...
  2. ncbi request reprint Medicinal flowers. XXVII. New flavanone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-alpha inhibitors from everlasting, flowers of Helichrysum arenarium
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan
    Chem Pharm Bull (Tokyo) 57:361-7. 2009
    ....
  3. doi request reprint Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2
    Genzoh Tanabe
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 20:6321-34. 2012
    ..Against isomaltase, all four analogs showed potent inhibitory activity as well as 2, and 11b and 11d exhibited enzyme selectivity...
  4. doi request reprint Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 66:39-48. 2012
    ..In addition, simultaneous quantitative analysis of eight flavonoid constituents from the flower and leaf parts of P. hendersonii was developed...
  5. doi request reprint Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 68:561-6. 2014
    ..3 μM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 μM), a clinical aldose reductase inhibitor. ..
  6. doi request reprint In silico design, synthesis and evaluation of 3'-O-benzylated analogs of salacinol, a potent α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine "Salacia"
    Genzoh Tanabe
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Chem Commun (Camb) 48:8646-8. 2012
    ....
  7. doi request reprint Anti-hyperlipidemic constituents from the bark of Shorea roxburghii
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 66:516-24. 2012
    ..o. and pancreatic lipase inhibitory activity (IC(50) = 32.9 and 26.5 μM, respectively)...
  8. doi request reprint New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora
    Saowanee Chaipech
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 66:486-92. 2012
    ..ex Baker. Their structures were established mainly on the basis of 1D and 2D NMR spectral data...
  9. ncbi request reprint Bioactive constituents from chinese natural medicines. XXXVI. Four new acylated phenylethanoid oligoglycosides, kankanosides J1, J2, K1, and K2, from stems of Cistanche tubulosa
    Yingni Pan
    Pharmaceutical Research and Technology Institute, Kinki University, Higashi Osaka, Osaka, Japan
    Chem Pharm Bull (Tokyo) 58:575-8. 2010
    ..Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, 3-5 were found to inhibit D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes...
  10. doi request reprint Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Food Chem 140:353-60. 2013
    ..A new flavonol glycoside, chakaflavonoside B (17), which was isolated in the course of this analytical study, was found to show oleic acid-albumin-induced lipid accumulation inhibitory activity...
  11. ncbi request reprint Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from Cistanche tubulosa
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, Higashi Osaka, Osaka 577 8502, Japan
    Chem Pharm Bull (Tokyo) 58:1403-7. 2010
    ..Their structures were elucidated on the basis of chemical and physicochemical evidence...
  12. doi request reprint Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography
    Osamu Muraoka
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Med 65:142-8. 2011
    ..959 for maltase and 0.795 for sucrase) was achieved...
  13. doi request reprint Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor
    Weijia Xie
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 19:2252-62. 2011
    ....
  14. ncbi request reprint Inhibitory effects of acylated acyclic sesquiterpene oligoglycosides from the pericarps of Sapindus rarak on tumor necrosis factor-alpha-induced cytotoxicity
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, Higashi Osaka, Osaka 577 8502, Japan
    Chem Pharm Bull (Tokyo) 58:1276-80. 2010
    ..These newly isolated compounds (1-4) were found to show inhibitory effects on tumor necrosis factor-alpha-induced cytotoxicity in L929 cells at concentrations of 30-100 microM...
  15. ncbi request reprint Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum
    Yuanyuan Xie
    Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan
    Chem Pharm Bull (Tokyo) 56:1628-31. 2008
    ....
  16. ncbi request reprint Quantitative analysis of catechin, flavonoid, and saponin constituents in "tea flower", the flower buds of Camellia sinensis, from different regions in Taiwan
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Nat Prod Commun 8:1553-7. 2013
    ....
  17. doi request reprint Suppressive effects of coumarins from Mammea siamensis on inducible nitric oxide synthase expression in RAW264.7 cells
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 20:4968-77. 2012
    ..With regard to mechanism of action of these active constituents (1, 9, and 11), suppression of STAT1 activation is suggested to be mainly involved in their suppression of iNOS induction...
  18. ncbi request reprint Structures of two new phenolic glycosides, kaempferiaosides A and B, and hepatoprotective constituents from the rhizomes of Kaempferia parviflora
    Saowanee Chaipech
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Chem Pharm Bull (Tokyo) 60:62-9. 2012
    ..Among the isolates, 5,3'-dihydroxy-3,7,4'-trimethoxyflavone showed higher activity than silybin, a commercial hepatoprotective agent...
  19. doi request reprint Biological evaluation of 3'-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3' position in the side chain on the α-glucosidase inhibitory activity
    Genzoh Tanabe
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem Lett 21:3159-62. 2011
    ..Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes...
  20. doi request reprint Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors
    Weijia Xie
    School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 19:2015-22. 2011
    ..Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose...
  21. doi request reprint Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors
    Shinya Nakamura
    Faculty of Pharmacy, Kinki University, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem Lett 20:4420-3. 2010
    ..Salacinol bound to the protein with a similar binding mode as casuarine, and the predicted structures could explain most of the structure-activity relationships of salacinol derivatives...
  22. ncbi request reprint Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity
    Genzoh Tanabe
    School of Pharmaceutical Sciences, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 15:3926-37. 2007
    ..These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity...
  23. doi request reprint Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Molecules 21:. 2016
    ..Among the active alkaloids, nornuciferine (2) was found to give a carbamate salt (2'') via formation of an unstable carbamic acid (2') by absorption of carbon dioxide from the air. ..
  24. doi request reprint Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia'
    Genzoh Tanabe
    Faculty of Pharmacy, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 24:3705-15. 2016
    ..Among the designed compounds, the one with a 3'-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1. ..
  25. doi request reprint Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines
    Kiyofumi Ninomiya
    Pharmaceutical Research and Technology Institute, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 70:435-51. 2016
    ..Among them, perennisaponin O (2, IC50 = 11.2, 14.3, and 6.9 μM, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death. ..
  26. doi request reprint Quantitative analysis of acylated oleanane-type triterpene saponins, chakasaponins I-III and floratheasaponins A-F, in the flower buds of Camellia sinensis from different regional origins
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 66:608-13. 2012
    ..Optimum conditions for the extraction process were also established...
  27. doi request reprint Evaluation of Salacia species as anti-diabetic natural resources based on quantitative analysis of eight sulphonium constituents: a new class of α-glucosidase inhibitors
    Junji Akaki
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    Phytochem Anal 25:544-50. 2014
    ..Their desulphonates (2, 4, 6 and 8) were also isolated as active constituents. Two separate quantitative analytical protocols, that is, for 1 and 3 and for 2 and 4, have been developed recently...
  28. doi request reprint Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 68:539-49. 2014
    ..The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable. ..
  29. doi request reprint Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 20:832-40. 2012
    ....
  30. doi request reprint Facile synthesis of de-O-sulfated salacinols: revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor
    Genzoh Tanabe
    School of Pharmacy, Kinki University, Higashi Osaka, Osaka, Japan
    Bioorg Med Chem Lett 19:2195-8. 2009
    ..Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified...
  31. doi request reprint Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 18:1882-90. 2010
    ..2 microM), and cistantubuloside B(1) (11, 21.4 microM) also reduced TNF-alpha-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100mg/kg, po...
  32. doi request reprint Quantitative determination of potent alpha-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry
    Osamu Muraoka
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    J Pharm Biomed Anal 52:770-3. 2010
    ..reticulata had the highest contents of these compounds. The results indicated that the assay was reproducible and precise and could be readily utilized for the evaluation of Salacia species...
  33. doi request reprint Mangiferin induces apoptosis in multiple myeloma cell lines by suppressing the activation of nuclear factor kappa B-inducing kinase
    Tomoya Takeda
    Division of Pharmacotherapy, Kinki University School of Pharmacy, Kowakae, Higashi Osaka, Japan
    Chem Biol Interact 251:26-33. 2016
    ..Importantly, since the number of reported NIK inhibitors is limited, mangiferin, which targets NIK, may be a potential anticancer agent for the treatment of MM. ..
  34. doi request reprint Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit
    Yoshiaki Manse
    Pharmaceutical Research and Technology Institute, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 24:6215-6224. 2016
    ..Furthermore, the active compounds 1-3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity...
  35. doi request reprint Simultaneous quantitative analysis of 12 methoxyflavones with melanogenesis inhibitory activity from the rhizomes of Kaempferia parviflora
    Kiyofumi Ninomiya
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 70:179-89. 2016
    ..The results indicated that the assay was reproducible, precise, and could be readily utilized for the quality evaluation of the plant materials...
  36. pmc Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka, 577 8502, Japan
    J Nat Med 69:494-506. 2015
    ..Among them, chalconaringenin 2'-O-β-D-glucopyranoside (16, IC50 = 23.1 μM) and aureusidin 6-O-β-D-glucopyranoside (35, 24.3 μM) showed relatively strong inhibitory activities. ..
  37. pmc Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidates from the Thai traditional natural medicine Salacia chinensis
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Nutrients 7:1480-93. 2015
    ..In addition, 1-4 were hardly absorbed from the intestine in an experiment using the in situ rat ligated intestinal loop model. The results indicate that these sulfoniums are promising leads for a new type of anti-diabetic agents. ..
  38. ncbi request reprint [Pharmaceutical food science: search for anti-obese constituents from medicinal foods-anti-hyperlipidemic saponin constituents from the flowers of Bellis perennis]
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan
    Yakugaku Zasshi 130:673-8. 2010
    ..In this review, our recent studies on anti-hyperlipidemic saponin constituents from flowers of Bellis perennis are described...
  39. pmc The Antiproliferative Effect of Chakasaponins I and II, Floratheasaponin A, and Epigallocatechin 3-O-Gallate Isolated from Camellia sinensis on Human Digestive Tract Carcinoma Cell Lines
    Niichiro Kitagawa
    Pharmaceutical Research and Technology Institute, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Int J Mol Sci 17:. 2016
    ..DNA fragmentation and caspase-3/7 activation were also detected after 48 h. These results suggested that antiproliferative activities of 1-3 induce apoptotic cell death via activation of caspase-3/7...
  40. pmc Hepatoprotective Limonoids from Andiroba (Carapa guianensis)
    Kiyofumi Ninomiya
    Pharmaceutical Research and Technology Institute, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Int J Mol Sci 17:. 2016
    ..In addition, the structural requirements of limonoids (1-17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated. ..
  41. doi request reprint Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan Antiaging Centre, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan Electronic address
    Phytochemistry 116:203-12. 2015
    ....
  42. doi request reprint Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: role of the length of alditol side chain
    Nozomi Tsutsui
    Laboratory of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 23:3761-73. 2015
    ..The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity...
  43. doi request reprint Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua
    Genzoh Tanabe
    Faculty of Pharmacy and Pharmaceutical Research and Technology Institute, Kinki University, Higashi Osaka, Osaka 577 8502, Japan
    J Nat Prod 78:1536-42. 2015
    ..7 μM) of 6 was 40 times stronger than that of arbutin (174 μM), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor within this class of compounds. ..
  44. doi request reprint Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Phytochemistry 102:169-81. 2014
    ..o. The mode of action was ascribable to the reduction in cytotoxicity caused by d-GalN. ..
  45. doi request reprint Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Phytochemistry 70:1166-72. 2009
    ....
  46. doi request reprint Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 4: Role of acyl side chains on d-mannose
    Nozomi Tsutsui
    Laboratory of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Kindai University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Eur J Med Chem 121:250-71. 2016
    ..These results suggested that peracylated mannose structure is critical for calcium signal-modulating activity, and this activity is precisely dependent on the length of four acyl side chains on d-mannose. ..
  47. doi request reprint Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry
    Nozomi Tsutsui
    Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem 22:945-59. 2014
    ..All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating. ..
  48. doi request reprint Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum
    Reiko Sugiura
    Laboratory of Molecular Pharmacogenomics, School of Pharmacy, Kinki University, 3 4 1 Kowakae, Higashi Osaka, Osaka 577 8502, Japan
    Bioorg Med Chem Lett 22:6735-9. 2012
    ..The activity was so potent as to exert the effect at a concentration of 200 nM...
  49. doi request reprint Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga
    Tomohisa Yasuhara
    School of Pharmacy, Kinki University, Higashiosaka, Osaka, Japan
    Bioorg Med Chem Lett 19:2944-6. 2009
    ..The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production...
  50. ncbi request reprint Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium
    Toshio Morikawa
    Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan
    Chem Pharm Bull (Tokyo) 57:853-9. 2009
    ..Their structures were elucidated on the basis of chemical and physicochemical evidence...
  51. doi request reprint Mangiferin enhances the sensitivity of human multiple myeloma cells to anticancer drugs through suppression of the nuclear factor κB pathway
    Tomoya Takeda
    Division of Pharmacotherapy, Kinki University School of Pharmacy, Kowakae, Higashi Osaka, Japan
    Int J Oncol 48:2704-12. 2016
    ..Our findings suggest that the combination of mangiferin and an anticancer drug could be used as a new regime for the treatment of MM. ..
  52. doi request reprint Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with Reformatsky Reagents
    Mitsuhiro Yoshimatsu
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari Tobetsu, Hokkaido 061 0293, Japan
    J Org Chem 80:9480-94. 2015
    ..The copper-mediated reactions of isolable Blaise intermediates (enamino esters 3), uniquely underwent 5-endo cyclization to afford the β-2,5-dihydropyrrolyl α,β-unsaturated esters 5aa-5fc, which exhibit anticancer activity. ..
  53. doi request reprint Guianolides A and B, new carbon skeletal limonoids from the seeds of Carapa guianensis
    Takanobu Inoue
    Osaka University of Pharmaceutical Sciences, 4 20 1 Nasahara, Takatsuki, Osaka 569 1094, Japan, and Faculty of Pharmaceutical Sciences, Kinki University, 3 4 1 Kowakae, Higashiosaka, Osaka 577 8502, Japan
    Org Lett 15:3018-21. 2013
    ..Their structures were established by spectroscopic analyses and X-ray crystallography. Guianolides A (1) and B (2) featured an unprecedented carbon skeleton via the formation of a C-11-C-21 bond. ..
  54. doi request reprint Copper-catalyzed complete regio- and stereoselective cyclization of 1-aryl-3-sulfanyl-4-oxahepta-1,6-diynes triggered by alkynylation
    Mitsuhiro Yoshimatsu
    Department of Chemistry, Faculty of Education, Gifu University, Yanagido 1 1, Japan
    Org Lett 14:3190-3. 2012
    ....
  55. ncbi request reprint Absolute stereostructure of potent alpha-glucosidase inhibitor, Salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata
    Masayuki Yoshikawa
    Kyoto Pharmaceutical University, Misasagi, Yamashina ku, 607 8412, Kyoto, Japan
    Bioorg Med Chem 10:1547-54. 2002
    ....
  56. ncbi request reprint Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum
    Kiyofumi Ninomiya
    Kyoto Pharmaceutical University, Kyoto, Japan
    Chem Pharm Bull (Tokyo) 55:1185-91. 2007
    ..Among them, sedumoside F(1) (IC(50)=47 microM), (3S,5R,6S,9R)-megastigmane-3,9-diol (61 microM), and myrsinionosides A (52 microM) and D (62 microM) were found to show the strong hepatoprotective activity...