Publications by authors named "Hiroyuki Miyashita"

49 Publications

Sézary Syndrome with CD4/CD8 Double-Negative Neoplastic T Cells in Peripheral Blood.

Case Rep Hematol 2021 1;2021:5527725. Epub 2021 Jun 1.

Department of Hematology, Yokkaichi Municipal Hospital, 2-2-37 Shibata, Yokkaichi 510-8567, Japan.

Sézary syndrome is a rare leukemic type of cutaneous T-cell lymphoma characterized by the presence of neoplastic T cells with cerebriform nuclei (Sézary cells) in the skin, lymph nodes, and peripheral blood. Typical Sézary cells have a CD3CD4CD8 phenotype; however, in cases of the aberrant loss of antigens on Sézary cells, especially the loss of critically important T-cell antigens such as CD4, there is a possibility of misdiagnosing the disease or underestimating the tumor burden of the disease. Here, we report a rare case of Sézary syndrome with CD4/CD8 double-negative Sézary cells in the peripheral blood. Most of the Sézary cells in the peripheral blood had lost CD4 expression, and we diagnosed the disease and evaluated the tumor burden by multicolor flow cytometry. Intriguingly, the Sézary cells showed a typical CD4CD8CD7 phenotype in the skin even though the cells in the peripheral blood lacked CD4. The patient responded well to treatment with bexarotene and narrow-band ultraviolet B therapy. Analysis by multicolor flow cytometry is essential to diagnose this rare type of Sézary syndrome and evaluate the tumor burden.
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http://dx.doi.org/10.1155/2021/5527725DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8189774PMC
June 2021

A New Glycosidic Acid, Muricatic Acid D, and Resin Glycosides, Muricatins X and XI, from the Crude Resin Glycoside Fraction of the Seeds of Ipomoea muricata.

Chem Pharm Bull (Tokyo) 2021 ;69(3):291-297

Faculty of Pharmaceutical Sciences, Sojo University.

Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3S-hydroxybutyric acid. Two new genuine resin glycosides with macrolactone structures (jalapins), muricatins X and XI, were also isolated from the fraction. Their structures were determined using spectroscopic data and chemical evidence.
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http://dx.doi.org/10.1248/cpb.c20-00905DOI Listing
July 2021

A new steroidal glycoside from the fruits of .

Nat Prod Res 2020 Jun 19:1-8. Epub 2020 Jun 19.

Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan.

A new cholestane-type steroidal glycoside, solamyriaside A (), was isolated from the fruits of Dunal (Solanaceae), along with two known steroidal glycosides, namely, solaviaside A () and aculeatiside A (), and three known steroidal alkaloid glycosides, namely, solamargine (), khasianine () and solasonine (), which were isolated for the first time from this plant. Based on spectroscopic data as well as chemical evidence, was determined to be 3--α-L-rhamnopyranosyl-(1→2)--[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-22,25-cholest-5-ene-3β,16α,22,26-tetraol 26--β-D-glucopyranoside. The cytotoxic activity of - against HL-60 human promyelocytic leukaemia cells was examined. Compounds - showed cytotoxic activity. Among them, exhibited the strongest activity with an IC value of 4.64 ± 0.17 μM, similar to the activity of cisplatin, a positive control.
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http://dx.doi.org/10.1080/14786419.2020.1781117DOI Listing
June 2020

Two new glycosidic acids, calyhedic acids E and F, in crude resin glycoside fraction from .

Nat Prod Res 2020 May 6:1-8. Epub 2020 May 6.

Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan.

Two new glycosidic acids, calyhedic acids E () and F (), were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the crude resin glycoside fraction obtained from whole plants of Wall. Compounds and were characterised as 11-hydroxyhexadecanoic acid 11--β-D-glucopyranosyl-(1→6)--β-D-glucopyranosyl-(1→6)--β-D-glucopyranosyl-(1→3)-[-α-L-rhamnopyranosyl-(1→2)]--β-D-glucopyranosyl-(1→2)-β-D-quinovopyranoside and an isomer of , in which the 11-hydroxyhexadecanoyl residue of was replaced by a 12-hydroxyhexadecanoyl residue, respectively, on the basis of spectroscopic data.
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http://dx.doi.org/10.1080/14786419.2020.1761362DOI Listing
May 2020

Identification and characterization of organic and glycosidic acids in crude resin glycoside fraction from Calystegia hederacea.

J Nat Med 2020 Jan 5;74(1):200-211. Epub 2019 Nov 5.

Faculty of Pharmaceutical Sciences, Sojo University, 4-22-2 Ikeda, Nishi-ku, Kumamoto, 860-0082, Japan.

Resin glycosides are well known as the purgative ingredients, which are characteristic of convolvulaceous plants. Calystegia hederacea Wall. is a perennial herbaceous vine that is widespread throughout India and East Asia. All parts of this plant are used for the treatment of menoxenia, gonorrhea, etc. Alkaline hydrolysis of the crude resin glycoside fraction of the whole plants of C. hederacea yielded four new glycosidic acids, calyhedic acids A, B, C, and D, along with two known glycosidic acids, calysolic acids A and C, and three known organic acids, 2S-methylbutyric, tiglic, and 2R,3R-nilic acids. Their structures were characterized on the basis of spectroscopic data and chemical evidence. Calyhedic acids A, B, and D were penta-, hexa-, and hepta-glycosides of 12S-hydroxyhexadecanoic acid, respectively, and cayhedic acid C was an isomer of calyhedic acid D, in which the 12S-hydroxyhexadecanoyl residue of calyhedic acid D was replaced by a 11S-hydroxyhexadecanoyl residue. Additionally, cytotoxic activity toward HL-60 human promyelocytic leukemia cells of the crude resin glycoside fraction, the glycosidic acid fraction, calyhedic acid A, and calysolic acid A from C. hederacea was evaluated. Furthermore, to clarify the structure-activity relationship of resin glycosides, the activities of six genuine resin glycosides with calysolic acid A or calysolic acid C as the glycosidic acid, which were isolated from C. soldanella, were examined. Among them, the crude resin glycoside fraction and five genuine resin glycosides with macrolactone structures demonstrated clear cytotoxic activities, while the glycosidic acid fraction, calyhedric acid A, calysolic acid A, and a genuine non-macrolactone-type resin glycoside were either inactive or exhibited weaker activity than the tested macrolactone-type resin glycosides.
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http://dx.doi.org/10.1007/s11418-019-01366-9DOI Listing
January 2020

A new resin glycoside from Calystegia soldanella and its antiviral activity towards herpes.

Nat Prod Res 2017 Nov 20;31(22):2660-2664. Epub 2017 Jan 20.

c Faculty of Pharmaceutical Sciences , Sojo University , Kumamoto , Japan.

A new resin glycoside, named calysolin XVIII (1), was isolated from the leaves, stems and roots of Calystegia soldanella Roem. et Schult. (Convolvulaceae). The structure of 1 was defined as 11S-jalapinolic acid 11-O-β-d-glucopyranosyl-(1 → 3)-O-(2-O-2S-methylbutyryl,4-O-3-hydroxy-2-methylenebutyryl)-α-l-rhamnopyranosyl-(1 → 2)-[O-β-d-glucopyranosyl-(1 → 6)-O-(34-di-O-2S-methylbutyryl)-β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 2)-β-d-quinovopyranoside, intramolecular 1,2″'″'-ester on the basis of spectroscopic data. Compound 1 is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, 1 demonstrated an antiviral activity against herpes simplex virus type 1, with an IC value 2.3 μM.
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http://dx.doi.org/10.1080/14786419.2017.1280492DOI Listing
November 2017

Acylated Glycosidic Acid Methyl Esters Generated from the Convolvulin Fraction of Rhizoma Jalapae Braziliensis by Treatment with Indium(III) Chloride in Methanol.

Chem Pharm Bull (Tokyo) 2017 ;65(1):107-111

School of Agriculture, Tokai University.

Four hexaglycosides of methyl 3S,12S-dihydroxyhexadecanoate (1-4) were provided after treatment of the crude convolvulin fraction from Rhizoma Jalapae Braziliensis (the root of Ipomoea operculata (GOMES) MART., Convolvulaceae) with indium(III) chloride in methanol. The structures of 1-4 were elucidated on the basis of spectroscopic and chemical methods. Their sugar moieties were partially acylated with organic acids including (3S,9R)-3,6:6,9-diepoxydecanoic (exogonic) acid, (E)-2-methylbut-2-enoic (tiglic) acid, and isovaleric acid.
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http://dx.doi.org/10.1248/cpb.c16-00673DOI Listing
February 2017

Two new prenylflavonoids from Epimedii Herba and their inhibitory effects on advanced glycation end-products.

J Nat Med 2016 Apr 12;70(2):290-5. Epub 2016 Jan 12.

Faculty of Pharmaceutical Sciences, Sojo University, 4-22-1 Ikeda, Nishi-ku, Kumamoto, 860-0082, Japan.

Because inhibitors of advanced glycation end-products (AGEs), for example pyridoxamine, significantly inhibit the development of retinopathy and neuropathy in rats with streptozotocin-induced diabetes, treatment with AGE inhibitors is believed to be a potential strategy for the prevention of lifestyle-related diseases such as diabetic complications. In the present study, the MeOH extract of Epimedii Herba (EH; aerial parts of Epimedium spp.) was found to inhibit the formation of N (ε) -(carboxymethyl)lysine (CML) and N (ω) -(carboxymethyl)arginine (CMA) during incubation of collagen-derived gelatin with ribose. Furthermore, compounds with inhibitory effects against CML and CMA formation were isolated from EH. Two new prenylflavonoids (compounds 1 and 2) and two known compounds (3 and 4) were found to significantly inhibit the formation of both CML and CMA; compound 4 (epimedokoreanin B) had the strongest inhibitory effect of the isolated compounds. These data suggest that epimedokoreanin B could prevent clinical complications of diabetes by inhibiting AGEs.
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http://dx.doi.org/10.1007/s11418-015-0962-0DOI Listing
April 2016

A new triterpenoid glycoside from the leaves and stems of Duranta repens.

Nat Prod Res 2016 2;30(2):246-50. Epub 2015 Jul 2.

a School of Agriculture, Tokai University , Minamiaso 5435, Aso, Kumamoto 869-1404 , Japan.

A new triterpenoid glycoside (1) was isolated from the methanol extract of the leaves and stems of Duranta repens L. (Verbenaceae) along with 14 known compounds consisting of eight triterpenoids, four iridoids, one phenylethanoid glycoside and one flavonoid. The chemical structure of 1 was determined to be bayogenin 3-O-[β-D-glucopyranoside]-28-O-[α-L-rhamnopyranosyl-(1→5)-O-β-D-apiofuranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl] ester, based on spectroscopic data. In addition, the inhibitory effects of the isolates on lipoxygenase activity were examined. Among them, acteoside and apigenin resulted in 94 ± 3.6% and 82 ± 4.7% inhibition, respectively, at 0.5 mM.
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http://dx.doi.org/10.1080/14786419.2015.1046870DOI Listing
August 2016

Four new acylated glycosidic acid methyl esters isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol.

Chem Pharm Bull (Tokyo) 2014 ;62(8):830-5

School of Agriculture, Tokai University.

Four new acylated glycosidic acid methyl esters were isolated after treatment of the crude ether-insoluble resin glycoside (convolvulin) fraction obtained from the seeds of Quamoclit pennata BOJER (Convolvulaceae) with indium(III) chloride in methanol. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.
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http://dx.doi.org/10.1248/cpb.c14-00277DOI Listing
March 2015

Three acylated glycosidic acid methyl esters and two acylated methyl glycosides generated from the convolvulin fraction of seeds of Quamoclit pennata by treatment with indium(III) chloride in methanol.

Chem Pharm Bull (Tokyo) 2013 ;61(9):952-61

School of Agriculture, Tokai University.

Treatment of the ether-insoluble resin glycoside (convolvulin) fraction from seeds of Quamoclit pennata (Convolvulaceae) with indium(III) chloride in methanol provided three oligoglycosides of hydroxy fatty acid (glycosidic acid) methyl esters and two methyl glycosides, which were partially acylated by a glycosidic acid, 7S-hydroxydecanoic acid 7-O-β-D-quinovopyranoside (quamoclinic acid B) and/or two organic acids, (E)-2-methylbut-2-enoic (tiglic) acid and/or 3R-hydroxy-2R-methylbutyric (nilic) acid. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.
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http://dx.doi.org/10.1248/cpb.c13-00355DOI Listing
March 2014

Three new resin glycosides and a new tetrahydropyran derivative from the seeds of Quamoclit pennata.

Chem Pharm Bull (Tokyo) 2012 ;60(8):1083-7

School of Agriculture, Tokai University, 5435 Minamiaso, Aso, Kumamoto 869-1404, Japan.

Three new resin glycosides, quamoclins V (1), VI (2), and VII (3) and a new tetrahydropyran derivative, quamopyran (4), were isolated from the seeds of Quamoclit pennata BOJER (Convolvulaceae). The chemical structures of these compounds were determined primarily on the basis of spectroscopic data. The carboxyl group of the aglycone, 11S-convolvulinolic acid, of 1 and 2 was linked intermoleculary with a hydroxy group of the sugar moiety to form a macrocyclic ester structure, as in already known jalapins, and 3 was an acylated glycosidic acid methyl ester. All of the sugar moieties of 1-3 were acylated by one 2S-methylbutyric acid. Compound 4 was a diketone having a tetrahydropyran ring.
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http://dx.doi.org/10.1248/cpb.c12-00334DOI Listing
December 2012

[Localization of language function in the brain].

Brain Nerve 2011 Dec;63(12):1339-45

Department of Basic Science, The University of Tokyo, Tokyo, Japan.

Since the first report of an aphasic patient by Paul Broca, the localization of brain function has been disputed for 150 years. In lesion studies, double dissociation has been a key concept to show the localization of particular cognitive functions. The advancement of non-invasive brain imaging methods enables us to investigate the brain activities under well-controlled conditions, further promoting the studies on the localization of the cognitive functions, including language function. Brain imaging studies, together with subtraction and correlation analyses, have accumulated evidence that syntax, phonology, and sentence comprehension are separately processed by modules in different cortical regions. More specifically, it has been clarified that the module for syntax localizes in the left lateral premotor cortex and the opercular/triangular parts of the left inferior frontal gyrus. This modular structure further suggests that aphasia is interpreted as deficits in either syntactic or phonological processing. Therefore, the classical model of contrasting speech production and comprehension should be updated. According to theoretical linguistics, on the other hand, the recursive computation of syntactic structures is an essential feature of human language faculty. One direction of research would be to contrast human beings and animals for the abilities of processing symbolic sequences. Another direction is to clarify that the human brain is indeed specialized in language processing, which can be revealed by well-controlled language tasks and functional imaging techniques. Here we will review recent studies that demonstrate the existence of grammar center in the left frontal cortex. The future studies in the neuroscience of language will eventually elucidate the cortical localization of language function in a more precise way, i.e., what is really computed in the human brain.
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December 2011

Garlicnin A from the fraction regulating macrophage activation of Allium sativum.

Chem Pharm Bull (Tokyo) 2011 ;59(11):1340-3

Faculty of Pharmacy, Tanta University, Egypt.

Garlicnin A (1), a new stable, sulfur-containing compound isolated from a fraction of the acetone extracts of Allium sativum L. garlic bulbs, showed the potential to suppress tumor cell proliferation by inhibiting the polarization of M2 alternatively activated macrophages, and its structure was characterized as 3,4-dimethyl-5-(4,5-dithia-1E,7-octadiene)-tetrahydrothiophene-2-sulfoxide-S-oxide, on the basis of the results of spectroscopic analysis results.
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http://dx.doi.org/10.1248/cpb.59.1340DOI Listing
March 2012

Identification and characterization of component organic and glycosidic acids of crude resin glycoside fraction from Calystegia soldanella.

Chem Pharm Bull (Tokyo) 2011 ;59(9):1163-8

School of Agriculture, Tokai University, Japan.

Alkaline hydrolysis of the crude resin glycoside fraction of the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae) gave four new glycosidic acids, named calysolic acids A, B, C, and D, along with one known glycosidic acid, soldanellic acid B, and three organic acids, 2S-methylbutyric, tiglic, and 2S,3S-nilic acids. The structures of the new glycosidic acids were characterized on the basis of spectroscopic data and chemical evidence.
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http://dx.doi.org/10.1248/cpb.59.1163DOI Listing
January 2012

Four new iridoid glucosides from Ajuga reptans.

Chem Pharm Bull (Tokyo) 2011 ;59(8):1065-8

Tokai University School of Agriculture, Japan.

Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid glycoside exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and H₂O₂ scavenging activities.
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http://dx.doi.org/10.1248/cpb.59.1065DOI Listing
December 2011

Three-dimensional structure of the signal peptide peptidase.

J Biol Chem 2011 Jul 2;286(29):26188-97. Epub 2011 Jun 2.

Department of Neuropathology and Neuroscience, Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.

Signal peptide peptidase (SPP) is an atypical aspartic protease that hydrolyzes peptide bonds within the transmembrane domain of substrates and is implicated in several biological and pathological functions. Here, we analyzed the structure of human SPP by electron microscopy and reconstructed the three-dimensional structure at a resolution of 22 Å. Enzymatically active SPP forms a slender, bullet-shaped homotetramer with dimensions of 85 × 85 × 130 Å. The SPP complex has four concaves on the rhombus-like sides, connected to a large chamber inside the molecule. Intriguingly, the N-terminal region of SPP is sufficient for the tetrameric assembly. Moreover, overexpression of the N-terminal region inhibited the formation of the endogenous SPP tetramer and the proteolytic activity within cells. These data suggest that the homotetramer is the functional unit of SPP and that its N-terminal region, which works as the structural scaffold, has a novel modulatory function for the intramembrane-cleaving activity of SPP.
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http://dx.doi.org/10.1074/jbc.M111.260273DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3138278PMC
July 2011

Dolabellane diterpene and three cycloartane glycosides from Thalictrum squarrosum.

Chem Pharm Bull (Tokyo) 2010 Aug;58(8):1043-6

Faculty of Pharmaceutical Sciences, Sojo University, Ikeda, Kumamoto, Japan.

A new dolabellane diterpene glycoside, named squoside A, and three new cycloartane glycosides, named squarrosides V, VI, and VII, have been isolated from the dried aerial parts of Thalictrum squarrosum (Ranunculaceae). Their structures were determined by two dimensional (2D) NMR spectroscopic analysis and chemical evidence.
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http://dx.doi.org/10.1248/cpb.58.1043DOI Listing
August 2010

Study of constituents of Veronicastrum villosulum.

J Nat Med 2010 Oct 25;64(4):510-3. Epub 2010 Jun 25.

Faculty of Pharmaceutical Sciences, Sojo University, 22-1, 4-chome, Ikeda, Kumamoto, 860-0082, Japan.

We investigated the constituents of Veronicastrum villosulum (Miquel) Yamazaki (Scrophulariaceae), an endangered species belonging to the IA group. From the aerial parts of this plant cultivated at the botanical garden of Sojo University, we isolated two new cucurbitacine-type glycosides, 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranosides of 3beta,25-dihydroxycucurbit-5,23(E)-diene-7-one-25-methyl ether and 3beta,23-dihydroxycucurbit-5,24-diene-7-one-23-methyl ether.
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http://dx.doi.org/10.1007/s11418-010-0439-0DOI Listing
October 2010

[Fascination with natural glycosides].

Yakugaku Zasshi 2010 May;130(5):679-86

Faculty of Medical & Pharmaceutical Sciences, Kumamoto University, Kumamot, Japan.

Recent progress in glycobiology reveals that sugar-chains play a crucial role in cell-cell recognition among immunity, inflammation, and malignant tumor in the living body. To study the mechanism of action requires a sample of sufficient quantity. However, isolating a sugar chain and a glycoside in pure form, difficulty follows sugar chain composition again, and studies have been limited to a few sugar chains. Glycosides are a group of compounds known to be the active principle of a natural drug. We have isolated triterpene glycosides from a Leguminosae plant, which improved liver disorder, and steroid glycosides from a plant of the Solanaceous with cytotoxic activity against human cancer cell lines. A biological activity test suggested an important role of the aglycone part and the sugar chain part of those glycosides. Although many studies of sugar chains of glycoprotein and glycolipid are known, there are few examples of studies of the sugar chain function of a glycoside of a natural drug, and the role of a sugar chain of a glycoside for its pharmacologic action expression is unknown. Therefore, as a biological tool investigating the function of a sugar chain of a natural glycoside, we have begun to synthesize a useful "glycoside" which can be utilized as a lead compound having activity.
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http://dx.doi.org/10.1248/yakushi.130.679DOI Listing
May 2010

Four new ent-kaurane diterpenoids from the fruits of Annona cherimola.

Chem Pharm Bull (Tokyo) 2010 May;58(5):765-8

Faculty of Pharmaceutical Sciences, Sojo University, 4-22-1 Ikeda, Kumamoto 862-0082, Japan.

Four new ent-kaurane diterpenoids (16R)-ent-kauran-17,19-diol (1), (16R)-17-hydroxy-ent-kauran-19-oic acid (2), (16S)-17-hydroxy-ent-kauran-19-oic acid (3), and (16R)-17-dimethoxy-ent-kauran-19-oic acid (4) have been isolated from the fresh fruits of Annona cherimola together with eight known compounds. Their structures are determined on the basis of spectroscopic data and optical rotation.
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http://dx.doi.org/10.1248/cpb.58.765DOI Listing
May 2010

Two new cucurbitane-type glycosides obtained from roots of Siraitia grosvenori SWINGLE.

Chem Pharm Bull (Tokyo) 2009 Aug;57(8):870-2

Guangxi Institute of Botany, Guangxi Zhuangzu Autonomous Region and Chinese Academy of Science, Guilin, China.

Novel Cucurbitane-type glycosides, 5beta,19beta-epoxy-29-nor-3,11-dioxo-cucurbit-24-ene-27-oic acid 27-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1) and 19,29-nor-3,11-dioxo-cucurbit-4,24-diene-27-oic acid 27-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2) were isolated from the roots of Siraitia grosvenori SWINGLE.
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http://dx.doi.org/10.1248/cpb.57.870DOI Listing
August 2009

A new spirostanol glycoside from fruits of Solanum indicum L.

Chem Pharm Bull (Tokyo) 2009 Jul;57(7):747-8

Faculty of Medical and Pharmaceutical Sciences, Kumamoto University.

A new characteristic steroidal glycoside of the 23S,26R-hydroxylated spirostanol-type named indioside F was isolated from the fruit of Solanum indicum, along with indioside A and protodioscin. On the basis of spectroscopic analysis, the structure of indioside F was found to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranosyl (beta-chacotriosyl) (22R,23S,25R,26R)-spirost-5-ene-3beta,23,26-triol.
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http://dx.doi.org/10.1248/cpb.57.747DOI Listing
July 2009

Two new acyclic diterpene glycosides from fruits of Habanero, Capsicum chinense.

Chem Pharm Bull (Tokyo) 2009 Jul;57(7):730-3

Faculty of Pharmaceutical Sciences, Sojo University.

Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV. The other two were new ones and were characterized as 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 17,19-dihydroxy-6E,10E,14Z-(3S)-geranyllinalool 17-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside and 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 6E,10E,14Z-(3S)-17-hydroxy-geranyllinalool 17-O-[3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 6'E,10'E,14'Z-(3'S)-13'R,19'-dihydroxy-geranyllinalool-16'-oyl (16'-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside.
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http://dx.doi.org/10.1248/cpb.57.730DOI Listing
July 2009

Steroidal glycosides from the fruits of Solanum viarum.

Chem Pharm Bull (Tokyo) 2009 Jun;57(6):632-5

School of Agriculture, Tokai University, 5435 Minamiaso, Aso, Kumamoto 869-1404, Japan.

Three new steroidal glycosides, named solaviasides A, B, and C, have been isolated from the fruits of Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae), along with seven known ones. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence.
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http://dx.doi.org/10.1248/cpb.57.632DOI Listing
June 2009

New C(28) steroidal glycosides from Tubocapsicum anomalum.

Chem Pharm Bull (Tokyo) 2008 Jul;56(7):1038-40

Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.

Two new C(28) steroidal glycosides, tuboanosides A (1) and B (2), were isolated from the fruit of Tubocapsicum anomalum MAKINO. Their chemical structures were elucidated on the basis of spectroscopic and X-ray diffraction analysis of the p-bromobenzoyl derivative (4) of tuboanosigenin (3), the sapogenol derivative of these two glycosides. Tuboanosides have the structural peculiarity of an unusual side chain carrying an unusual linkage with a C-21 bound to C-25 on the lactone ring.
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http://dx.doi.org/10.1248/cpb.56.1038DOI Listing
July 2008

A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides.

Chem Pharm Bull (Tokyo) 2008 Jul;56(7):1022-5

Aso Pharmaceutical Co Ltd, Kumamoto, Japan.

A new homostilbene, named scillabene A (2), and two new homoisoflavones, named scillavones A (3) and B (4), were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae) along with 13 known compounds comprising a homostilbene, seven homoisoflavones, a xanthone, a lignan, and three nortriterpenes. The structures of 2-4 were characterized as 3,5,4'-trihydroxy-3'-methoxy-4-methyl-trans-stilbene, (3R)-5,7,2'-trihydroxy-3',4'-dimethoxyspiro{2H-1-benzopyran-7'-bicyclo[4,2,0]octa[1,3,5]-trien}-4-one and (3S)-3-(3,4-dihydroxybenzyl)-5-hydroxy-6,7-dimethoxychroman-4-one, respectively, on the basis of spectroscopic data and X-ray crystallographic analysis.
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http://dx.doi.org/10.1248/cpb.56.1022DOI Listing
July 2008

Mechanism for conversion of spirosolane derivative into pregnane.

Chem Pharm Bull (Tokyo) 2008 Jul;56(7):1015-7

Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan.

Previously, we reported an interesting reaction by which esculeogenin A [(5alpha,22S,23S,25S)-3beta,23,27-trihydroxyspirosolane], a sapogenol of tomato-saponin, esculeoside A, was easily converted into a pregnane derivative, 5alpha-pregn-16-en-3beta-ol-20-one, merely by refluxing with pyridine and water. Its chemical mechanism including air oxidation is here described.
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http://dx.doi.org/10.1248/cpb.56.1015DOI Listing
July 2008

A pregnane glycoside from overripe tomato.

Chem Pharm Bull (Tokyo) 2008 Jul;56(7):1013-4

Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan.

A new pregnane glycoside, 3-O-beta-lycotetraosyl 5alpha-pregna-3beta,26beta-diol-20-one was isolated from overripe tomato, the fruit of Lycopersicon esculentum MILL.
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http://dx.doi.org/10.1248/cpb.56.1013DOI Listing
July 2008

Conversion of esculeoside A into esculeogenin B.

Chem Pharm Bull (Tokyo) 2008 Jul;56(7):926-9

Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.

Conversion of the spirosolane-type glycoside, esculeoside A, a major component contained in the ripe tomato Lycopersicon esculentum fruits, into a solanocapsine-type sapogenol, esculeogenin B-2, (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, and esculeogenin B-1, (5alpha,22R,23S,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, which are rare naturally occurring compounds was attained by acid hydrolysis with 2 N HCl in dioxane and water (1 : 1).
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http://dx.doi.org/10.1248/cpb.56.926DOI Listing
July 2008
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