New Toxic Metabolites from a Mushroom, Hebeloma vinosophyllum. II. Isolation and Structures of Hebevinosides VI, VII, VIII, IX, X, and XI(Organic,Chemical)
スポンサーリンク
概要
- 論文の詳細を見る
Four new triterpene glycosides, hebevinosides VI, VII, VIII, and IX, whose common aglycone is 3β,7β,16β-trihydroxycucurbita-5,24-diene (hydroxyhebevinogenin), have been isolated from the acetone extract of a poisonous mushroom, Hebeloma vinosophyllum, and deduced to have the structures of 3β,7β,16β-trihydroxycucurbita-5,24-diene-3-O-β-D-xylopyranoside-16-0-β-D-glucopyranoside, 3β7β,16β-trihydroxycucurbita-5,24-diene-3-O-β-D-xylopyranoside-16-O-(4,6-di-O-acetyl)-β-D-glucopyranβide, 3β,7β,16β-trihydroxycucurbita-5,24-diene-3-0-(4-0-acetyl)-β-D-xylopyranoside-16-0-(4,6-di-O-acetyl)-β-D-glucopyranoside, and 3β,7β,16β-trihydroxycucurbita-3-0-β-D-xylopyranoside, respectively. Two new glycosides, hebevinosides X and XI, whose common aglycone is 3β, 6β-dihydroxy-7β-methoxycucurbita-5,24-diene (methoxyhebevinogenin), have also been isolated from the aqueous methanolic extract of the mushroom in addition to hebevinosides I, II, III, IV, and V previously reported, and deduced to be 3β,16β-dihydroxy-7β-methoxycucurbita-5,24-diene-3-O-β-D-xylopyranoside-16-O-β-D-glucopyranoside and 3β,16β-di-hydroxy-7β-mcthoxycucurbita-5,24-diene-3-O-β-D-xylopyranoside-16-O-(4,6-di-O-acetyl)-β-D-glucopyranoside, respectively. Among these eleven hebevinosides, I, IV, V, X, and XI, whose common aglycone is methoxyhebevinogenin, have been proved to be artifacts formed from the genuine metabolites III, IX, II, VI, and VII, whose common aglycone is hydroxyhebevinogenin, during extraction of the mushroom with aqueous methanol, respectively, and VIII, whose aglycone is hydroxyhebevinogenin, has also been proved to be a genuine metabolite of this mushroom. The relationship between the structure and toxicity of hebevinosides was also investigated.
- 社団法人日本薬学会の論文
- 1987-06-25
著者
-
鈴木 久美子
千葉大学薬学部
-
藤本 治宏
Research Institute for Chemobiodynamics, Chiba University
-
萩原 秀美
Research Institute for Chemobiodynamics, Chiba University
-
鈴木 久美子
Research Institute for Chemobiodynamics, Chiba University
-
山崎 幹夫
Research Institute for Chemobiodynamics, Chiba University
-
藤本 治宏
千葉大院薬
-
萩原 秀美
Research Institute For Chemobiodynamics Chiba University
-
Yamazaki M
School Of Pharmaceutical Sciences Kinki University
関連論文
- Brazilian Natural Medicines. III. Structures of Triterpene Oligoglycosides and Lipase Inhibitors from Mate, Leaves of Ilex paraguariensis
- Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of Camellia oleifera : Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects
- Medicinal Flowers. XXI. : Structures of Perennisaponins A, B, C, D, E, and F, Acylated Oleanane-Type Triterpene Oligoglycosides, from the Flowers of Bellis perennis
- Medicinal Flowers. XXVII : New Flavanone and Chalcone Glycosides, Arenariumosides I, II, III, and IV, and Tumor Necrosis Factor-α Inhibitors from Everlasting, Flowers of Helichrysum arenarium
- Structures of Acetylated Oleanane-Type Triterpene Saponins, Rarasaponins IV, V, and VI, and Anti-hyperlipidemic Constituents from the Pericarps of Sapindus rarak
- Absolute Stereostructures of Olibanumols A, B, C, H, I, and J from Olibanum, Gum-Resin of Boswellia carterii, and Inhibitors of Nitric Oxide Production in Lipopolysaccharide-Activated Mouse Peritoneal Macrophages
- Medicinal Flowers. XXIV. Chemical Structures and Hepatoprotective Effects of Constituents from Flowers of Hedychium coronarium
- Medicinal Flowers. XXIII. New Taraxastane-Type Triterpene, Punicanolic Acid, with Tumor Necrosis Factor-α Inhibitory Activity from the Flowers of Punica granatum
- Bioactive Constituents from Chinese Natural Medicines. XXXII : Aminopeptidase N and Aldose Reductase Inhibitors from Sinocrassula indica: Structures of Sinocrassosides B_4, B_5, C_1, and D_1-D_3
- Medicinal Foodstuffs. XXXIV. : Structures of New Prenylchalcones and Prenylflavanones with TNF-α and Aminopeptidase N Inhibitory Activities from Boesenbergia rotunda
- Bioactive Constituents from Chinese Natural Medicines. XXVI : Chemical Structures and Hepatoprotective Effects of Constituents from Roots of Rhodiola sachalinensis
- Bioactive Constituents from Chinese Natural Medicines. XXIV. : Hypoglycemic Effects of Sinocrassula indica in Sugar-Loaded Rats and Genetically Diabetic KK-A^y Mice and Structures of New Acylated Flavonol Glycosides, Sinocrassosides A_1, A_2, B_1, and B_2
- クサウラベニタケの毒性成分の研究(第2報) : 溶血素の精製と溶血条件の検討
- クサウラベニタケの毒性成分の研究(第1報)生物活性と毒性成分の探索
- New Toxic Metabolites from a Mushroom, Hebeloma vinosophyllum. II. Isolation and Structures of Hebevinosides VI, VII, VIII, IX, X, and XI(Organic,Chemical)
- New Toxic Metabolites from a Mushroom, Hebeloma vinosophyllum. I. : Structures of Hebevinosides I, II, III, IV, and V
- 69 アカヒダワカフサタケの毒性代謝産物hebevinoside類の単離と構造(その2)
- 9 アカヒダワカフサタケの毒性代謝産物hebevinoside類の単離と構造
- THE TOXIC PRINCIPLES OF NAEMATOLOMA FASCICULARE
- Chemistry of Tremorogenic Metabolites. II. Structure Determination of Fumitremorgin B, a Tremorogenic Metabolite from Aspergillus fumigatus
- 78(P-35) 子嚢菌Chaetomium quadrangulatumのモノアミン酸化酵素阻害活性成分(ポスター発表の部)
- Apoptosis-Inducing Effects of Sterols from the Dried Powder of Cultured Mycelium of Cordyceps sinensis
- Application of High-Performance Liquid Chromatography Using Water-Containing Silica Gel Columns for Large-Scale Preparation of Cerebroside
- The Principles of Tetragonia tetragonoides having Anti-ulcerogenic Activity. II. Isolation and Structure of Cerebrosides
- STRUCTURE OF ED-1 ISOLATED FROM EMERICELLA DENTATA
- Isolation and Structures of Oxaphenalenone Dimers from Talaromyces bacillosporus
- Isolation of Some New Tryptoquivaline-related Metabolites from Aspergillus fumigatus
- 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
- Bioactive Constituents from Chinese Natural Medicines. XXII. Absolute Structures of New Megastigmane Glycosides, Sedumosides E_1, E_2, E_3, F_1, F_2, and G, from Sedum sarmentosum (Crassulaceae)
- Bioactive Saponins and Glycosides. XXVIII. New Triterpene Saponins, Foliatheasaponins I, II, III, IV, and V, from Tencha (the Leaves of Camellia sinensis)
- P-469 ANTI-ALLERGIC AND ANTI-INFLAMMATORY ACTIVITIES OF 1'S-1'-ACETOXYCHAVICOL ACETATE AND RELATED COMPOUNDS
- P-466 ACYLATED PHENETHYLGLYCOSIDES WITH VASORELAXANT ACTIVITY FROM CISTANCHE TUBULOSA
- P-298 SYNTHESIS OF 1,5-ANHYDRO-5-AZA-D-GLUCITOL ANALOGS OF SALACINOL AND THEIR α-GLUCOSIDASE INHIBITORY ACTIVITIES
- Monoterpene Constituents from Cistanche tubulosa : Chemical Structures of Kankanosides A-E and Kankanol
- Inhibitors of Nitric Oxide Production from the Rhizomes of Alpinia galanga : Structures of New 8-9' Linked Neolignans and Sesquineolignan
- Antidiabetogenic constituents from Salacia species(Chemical & Pharmacological study)
- Synthesis of a Nitrogen Analogue of Salacinol and Its α-Glucosidase Inhibitory Activity
- Saponins of Plants of Panax Species Collected in Central Nepal, and Their Chemotaxonomical Significance. III.
- Study on Anti-Oketsu Activity of Rhubarb II. Anti-allergic Effects of Stillbene Components from Rhei undulati Rhizoma(Dried Rhizome of Rheum undulatum Cultivated in Korea)
- Studies on Alismatis Rhizoma. III. Stereostructures of New Protostane-Type Triterpenes, Alisols H, I, J-23-Acetate, K-23-Acetate, L-23-Acetate, M-23-Acetate, and N-23-Acetate, from the Dried Rhizome of Alisma orientale
- Hepatoprotective and Antioxidative Properties of Salacia reticulata : Preventive Effects of Phenolic Constituents on CCl_4-Induced Liver Injury in Mice
- Medicinal Foodstuffs. XVIII. Phytoestrogens from the Aerial Part of Petroselinum crispum MILL. (PARSLEY) and Structures of 6"-Acetylapiin and a New Monoterpene Glycoside, Petroside
- Medicinal Flowers. II. Inhibitors of Nitric Oxide Production and Absolute Stereostructurs of Five New Germacrane-Type Sesquiterpenes, Kikkanols D, D Monoacetate, E, F, and F Monoacetate from the Flowers of Chrysanthemum indicum L.
- Chemical Constituents from the Leaves of Hydrangea macrophylla var. thunbergii(III) : Absolute Stereostructures of Hydramacrosides A and B, Secoiridoid Glucoside Complexes with Inhibitory Activity on Histamine Release
- The Role of Thunberginol A, an Isocoumarin Constituent of Hydrangeae Dulcis Folium, on the Signal Transmission Pathway for Rat Mast Cell Degranulation
- Effects of Phyllodulcin, Hydrangenol, and Their 8-O-Glucosides, and Thunberginols A and F from Hydrangea macrophylla SERINGE var. thunbergii MAKINO on Passive Cutaneous Anaphylaxis Reaction in Rats
- Medicinal Foodstuffs. XXIV.^ Chemical Constituents of the Processed Leaves of Apocynum venetum L. : Absolute Stereostructures of Apocynosides I and II
- Syntheses of Antifungal Isocoumarins. III. Synthesis and Antifungal Activity of 3-Aryl-3,4-dihydro-4-substituted-isocoumarins
- Antifungal Activity of Oosponol, Oospolactone, Phyllodulcin, Hydrangenol, and Some Other Related Compounds
- Syntheses of Antifungal Isocoumarins. II. Synthesis and Antifungal Activity of 3-Substituted Isocoumarins
- マイコトキシンの一種,デオキシニバレノールの土壌細菌による毒性低減化 : 微生物
- 111(P-58) 真菌由来α-ピロン環型天然物の立体化学(ポスター発表の部)
- 81(P-79) マユハキタケ科子嚢菌2種からの免疫調節活性成分の単離とその絶対配置(ポスター発表の部)
- 子嚢菌 Sordaria gondaensis の免疫抑制活性成分
- P-41 防風の鎮痛活性成分 II.
- 72(P47) Gelasinospora属子嚢菌3種からの免疫調節活性成分(ポスター発表の部)
- 子嚢菌 Emericella corrugata からの新毒性代謝産物
- 61(P31) 子嚢菌Diplogelasinospora grovesii及び関連菌からの新免疫抑制活性成分(ポスター発表の部)
- P-60 子嚢菌Gelasinospora multiforis及びG. kobiからの新免疫抑制活性成分(ポスター発表の部)
- Isolation of Some Immunosuppressive Components from an Ascomycete, Gelasinospora multiforis
- NEW FUNGAL METABOLITES AVELLANINS A AND B FROM HAMIGERA AVELLANEA, WITH PRESSOR EFFECT(Communication to the Editor)
- Four New Immunosuppressive Components, Kobiin and Kobifuranones A, B, and C, from an Ascomycete, Gelasinospora kobi
- 子のう菌 Talaromyces luteus より得られた新MAO阻害物質 Luteusin A と可逆的MAO-B阻害薬Ro16-6491との ex vivo におけるMAO阻害活性の比較検討
- Four New Chlorinated Azaphilones, Helicusins A-D, Closely Related to 7-epi-Sclerotiorin, from an Ascomycetous Fungus, Talaromyces helicus
- 子嚢菌 Gelasinospora pseudoreticulata 由来 Mycelia Sterilia からのモノアミン酸化酵素阻害活性成分
- Isolation and Characterization of Immunosuppressive Components of Three Mushrooms, Pisolithus tinctorius, Microporus flabelliformis and Lenzites betulina
- 38 子のう菌Talaromyces luteus、T. helicusより得られた新azaphilone代謝産物(口頭発表の部)
- Identification of Immunosuppressive Components of a Mushroom, Lactarius flavidulus
- Isolation, Identification and Pharmacological Studies on Three Toxic Metabolites from a Mushroom, Hebeloma spoliatum
- New Toxic Metabolites from a Mushroom, Hebeloma vinosophyllum. III. Isolation and Structures of Three New Glycosides, Hebevinosides XII, XIII and XIV, and Productivity of the Hebevinosides at Three Growth Stages of the Mushroom
- Biosynthesis of Silvaticamide, a Toxin from Aspergillus silvaticus
- Structure Determination of Violaceol-I and -II, New Fungal Metabolites from a Strain of Emericella violacea
- The Isolation and Structure Determination of Violaceic Acid, A New biphenyl Ether Type Metabolite from Emericella violacea
- The Absolute Configuration of Desacetylaustin isolated from Emericella nidulans var. dentata
- Isolation and Structure of Red Pigment from Aspergillus ochraceus WILH
- きのこの生理活性物質 (きのこの生物工学)
- 子嚢菌由来のxanthone系免疫抑制活性成分について (第14回天然薬物の開発と応用シンポジウム 講演要旨集) -- (一般講演 天然資源と医薬品開発2)
- Wrightiamines A and B, Two New Cytotoxic Pregnane Alkaloids from Wrightia javanica
- Analgesic Components of Saposhnikovia Root : Saposhnikovia divaricata
- Chemistry of Tremorogenic Metabolites. I. Fumitremorgin A from Aspergillus fumigatus
- Six New Constituents from an Ascomycete, Chaetomlum quadrangulatum, Found in a Screening Study Focused on Monoamine Oxidase Inhibitory Activity
- Monoamine Oxidase Inhibitory Naphthoquinone and/or Naphthalene Dimers from Lemuni Hitam (Diospyros sp.), a Malaysian Herbal Medicine
- Immunomodulatory Constituents from an Ascomycete, Microascus tardifaciens
- Immunomodulatory Constituents from Three Ascomycetes, Gelasinospora heterospora, G. multiforis, and G. longispora
- Manoamine Oxidase Inhibitory constituents from Anixiella micropertusa
- Immunosuppressive Components from an Ascomycete, Diplogelasinospora grovesii
- Isolation of New Tremorgenic Metabolites from an Ascomycete, Corynascus setosus
- REVISED STEREOSTRUCTURES OF LUTEUSINS C AND D
- Separation of Leucas aspera, a Medicinal Plant of Bangladesh, Guided by Prostaglandin Inhibitory and Antioxidant Activities
- Monoamine Oxidase-Inhibitory Components from an Ascomycete, Coniochaeta tetraspora
- Isolation of Three New Azaphilones, Luteusins C, D, and E, from an Ascomycete, Talaromyces luteus
- Five New Chromones Possessing Monoamine Oxidase Inhibitory Activity from an Ascomycete, Chaetomium quadrangulatum
- Novel Syntheses of Murrayaquinone A and Furostifoline through 4-Oxygenated Carbazoles by Allene-Mediated Electrocyclic Reactions Starting from 2-Chloroindole-3-carbaldehyde
- Six Immunosuppressive Features from an Ascomycete, Zopfiella longicaudata. Found in a Screening Study Monitored by Immunomodulatory Activity
- Immunomodulatory Constituents from an Ascomycete, Emericella aurantio-brunnea
- New Syntheses of Murrayaquinone A and Furostifoline
- Structure Determination of Six Fungal Metabolites, Tryptoquivaline E, F, G, H, I and J from Aspergillus fumigatus
- Structure of Tryptoquivaline C (FTC) and D (FTD). Novel Fungal Metabolites from Aspergillus fumigatus
- Analgesic Components of Glehnia Root (Glehnia littoralis)
- 子のう菌Talaromyces luteusより得られた新MAO阻害物質Luteusin Aと可逆的MAO-B阻害薬Ro16-6491とのex vivoにおけるMAO阻害活性の比較検討