Biotransformation of Benzaldehyde-Type and Acetophenone-Type Derivatives by Pharbitis nil Hairy Roots
スポンサーリンク
概要
- 論文の詳細を見る
The glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin and isovanillin were reduced to alcoholic derivatives and glucosylated at the phenolic and the alcoholic hydroxyl groups. In the case of 3, 4-dihydroxybenzaldehyde, the formyl group was reduced and the 3-hydroxyl or 4-hydroxyl groups were glucosylated to give monoglucosides. The 3-hydroxyl group was predominantly glucosylated to the 4-hydroxyl group. 4-β-D-Glucopyranosyloxy-3-methoxybenzylalco-hol was obtained in low yield. In time-course experiments with vanillin, it was found that the high-level reduction of the formyl group and glucosylation of the phenolic hydroxyl group occurred, and finally 4-O-β-D-glucopyra-nosylvanillylalcohol was obtained as the main product. In the case of 3, 4-dimethoxybenzaldehyde, 3, 4, 5-trimethoxybenzaldehyde, and salicylaldehyde, the formyl groups were reduced, and then the hydroxyl groups at the benyl position were glucosylated to give alcoholic glucosides in relatively high yields. In 4-hydroxy-3-methoxyacetophenone, the 4-hydroxyl group was glucosylated and two dimerized glucosides, biphenyl and biphenylether types, were obtained in low yields. In acetophenone, 1-β-D-glucopyranosyloxy-1-phenylethane and 2-β-D-glucopyranosyloxyacetophenone were obtained. As mentioned above P. nil hairy roots showed various biotransformative activities including glucosylation of phenolic and benzylic hydroxyl groups, reduction of the formyl group near the benzene ring, and phenol oxidation dimerization. The glucosylation reaction was especially interesting for the production of valuable glucosides.
- 公益社団法人日本薬学会の論文
- 2005-04-01
著者
-
KAWAHARA Nobuo
National Institute of Health Sciences
-
KUROYANAGI Masanori
School of Bioresources, Hiroshioma Prefectural University
-
NAKANE Takahisa
Showa Pharmaceutical University
-
MASUDA Kazuo
Showa Pharmaceutical University
-
Kuroyanagi M
Fac. Of Pharmaceutical Sciences At Kagawa Campus Tokushima Bunri Univ.
-
Masuda K
Showa Pharmaceutical Univ.
-
Masuda Kazuo
Showa College Of Pharmaceutical Sciences
-
Masuda K
Showa Pharmaceutical University
-
Nakane Takahisa
Biological Sci. Res. Lab. Lion Corp.
-
Nakane Takahisa
Showa Pharmaceutical Univ.
-
Kawahara N
National Institute Of Health Sciences
-
Takase Yoichi
Showa Pharmaceutical University
-
Kuroyanagi Masanori
Fac. Of Pharmaceutical Sciences At Kagawa Campus Tokushima Bunri Univ.
-
川原 信夫
National Institute Of Health Sciences
-
Takase Yoichi
Showa Pharmaceutical Univ.
-
KANHO Hideki
School of Bioresources, Hiroshima Prefectural University
-
YAOYA Sayaka
School of Bioresources, Hiroshima Prefectural University
-
Yaoya Sayaka
School Of Bioresources Hiroshima Prefectural University
-
Kanho Hideki
School Of Bioresources Hiroshima Prefectural University
-
Kuroyanagi Masanori
School Of Bioresources Hiroshima Prefectural University
-
Kimura Mariko
Fac. Of Food Culture Dep. Of Nutrition Kurashiki Sakuyo Univ.
-
Kawahara Nobuo
Tsukuba Div. Res. Center For Medicinal Plant Resources National Inst. Of Biomedical Innovation
-
Kawahara Nobuo
National Inst. Health Sci. Tokyo Jpn
-
Nakane Takahisa
Showa Parmaceutical University
関連論文
- In Vitro Leishmanicidal Activity of Benzophenanthridine Alkaloids from Bocconia pearcei and Related Compounds
- Production of Sesquiterpene-Type Phytoalexins by Hairy Roots of Hyoscyamus albus Co-treated with Cupper Sulfate and Methyl Jasmonate
- Enzymatic preparation of 1-O-hydroxycinnamoyl-β-D-glucoses and their application to the study of 1-O-hydroxycinnamoyl-β-D-glucose-dependent acyltransferase in anthocyanin-producing cultured cells of Daucus carota and Glehnia littoralis
- Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement
- Studies on Constituents from Chamaecyparis pisifera and Antibacterial Activity of Diterpenes
- Simultaneous determination of seven saponins in the roots of Codonopsis lanceolata by liquid chromatography-mass spectrometry
- Rapid identification of triterpenoid saponins in the roots of Codonopsis lanceolata by liquid chromatography-mass spectrometry
- Codonopsis lanceolata Ameliorate Plasma Testosterone Reduction Induced by Immobilization Stress in Middle-Aged Mice
- Codonopsis lanceolata Accelerates Recovery from the Reproductive Dysfunction Induced by Hyperthermic Treatment in Male Mice
- Triterpene Glycosides from the Roots of Codonopsis lanceolata
- Evaluation of the crude drugs by means of colorimeter. Part 6. : Correlation between the color and total polyphenol content of Geranium Herb
- Identification of N-Methyl-4-(3,4-Methylenedioxyphenyl) Butan-2-Amine, Distributed as MBDB
- Chemical Phenotypes of the hmg1 and hmg2 Mutants of Arabidopsis Demonstrate the In-planta Role of HMG-CoA Reductase in Triterpene Biosynthesis
- Leishmanicidal Active Constituents from Nepalese Medicinal Plant Tulsi (Ocimum sanctum L.)
- Fern Constituents: Dryocrassy Formate, Sitostanyl Formate and 12α-Hydroxyfern-9(11)-ene from Cyathea podophylla
- Study on Aquatic Fern : Terpenoids of Azolla japonica
- Fern Constituents : Triterpenoids from Adiantum capillus-veneris
- Study on Constituents of Latex : Triterpenoids of Euphorbia tirucalli
- Rearranged Lanostane Triterpenoids from Abies sachalinensis (III)
- Beyerane Derivatives and a Sesquiterpene Dimer from Japanese Cypress : Chamaecyparis obtusa
- Novel Lanostane and Rearranged Lanostane-Type Triterpenoids from Abies sachalinensis-II-
- A New Leishmanicidal Saponin from Brunfelsia grandiflora
- Neurite Outgrowth-Promoting Active Constituents of the Japanese Cypress (Chamaecyparis obtusa)
- New Diarylheptanoids from Alnus japonica and Their Antioxidative Activity
- A guanidine derivative from seeds of Plantago asiatica
- P-517 Leishmanicidal Constituents from Brunfelsia grandiflora
- Tumor Antigen Occurs in N-Glycan of Royal Jelly Glycoproteins : Honeybee Cells Synthesize T-Antigen Unit in N-Glycan Moiety
- Structural Features of N-Glycans Linked to Glycoproteins from Oil Palm Pollen, an Allergenic Pollen(Biochemistry & Molecular Biology)
- Purification and Characterization of 31-kDa Palm Pollen Glycoprotein (Ela g Bd 31 K), Which is Recognized by IgE from Palm Pollinosis Patients(Biochemistry & Molecular Biology)
- Authentication and Chemical Study of Isodonis Herba and Isodonis Extracts
- Malycorins A-C, New Lycopodium Alkaloids from Lycopodium phlegmaria
- Antitumor-Promoting Constituents from Chaenomeles sinensis KOEHNE and Their Activities in JB6 Mouse Epidermal Cells
- Seven Glycosides from Dioscorea bulbifera L
- Antitumor-Promoting Constituents from Dioscorea bulbifera L. in JB6 Mouse Epidermal Cells
- Seven Compounds from Dioscorea bulbifera L.
- NITIDASIN, A NOVEL SESTERTERPENOID, FROM THE PERUVIAN FOLK MEDICINE "HERCAMPURI" (GENTIANELLA NITIDA)
- 350-kDa Royal Jelly Glycoprotein (Apisin), Which Stimulates Proliferation of Human Monocytes, Bears the β1-3Galactosylated N-Glycan : Analysis of the N-Glycosylation Site(Biochemistry & Molecular Biology)
- First Evidence for Occurrence of Galβ1-3GlcNAcβ1-4Man Unit in N-Glycans of Insect Glycoprotein : β1-3Gal and β1-4GlcNAc Transferases Are Involved in N-Glycan Processing of Royal Jelly Glycoproteins(Biochemistry & Molecular Biology)
- Antiviral Activity of a Hot Water Extract of Black Soybean against a Human Respiratory Illness Virus(Food & Nutrition Science)
- Occurrence of GalNAcβ1-4GlcNAc Unit in N-Glycan of Royal Jelly Glycoprotein(Biochemistry & Molecular Biology)
- Structural Features of N-Glycans Linked to Royal Jelly Glycoproteins : Structures of high-mannose type, hybrid type, and biantennary type glycans
- Differentiation Inducing Activities of Isocoumarins from Hydrangea Dulcis Folium
- Studies on Differentiation Inducers. VI.Lignan Derivatives from Arctium Fructus. (2)
- P-127 Leishmanicidal constituents from a Myanmar plant Cordia fragrantissima
- Two New Cucurbitacin Glucosides, Opercurins A and B, from the Brazilian Folk Medicine "Buchinha" (Luffa operculata)
- Two Novel Cucurbitacins, Neocucrbitacins A and B, from the Brazilian Folk Medicine "Buchinha" (Luffa operculata)and Their Effect on PEBP2αA and OCIF Gene Expression in a Human Osteoblast-Like Saos-2 Cell Line
- Anti-androgenic Triterpenoids from the Brazilian Medicinal Plant, Cordia multispicata
- A New Secoiridoid Glucoside, Amaronitidin, from the Peruvian Folk Medicine "Hercampuri" (Gentianella nitida)
- A Novel Sesterterpenoid, Nitiol, as a potent Enhancer of IL-2 Gene Expression in a Human T Cell Line, from the Peruvian Folk Medicine"Hercumpuri" (Gentianella nitida)
- Anti-carcinogenic Activity of Taraxacum Plant. I
- Anti-tumor-Promoting Activities of Triterpenoids from Ferns. I
- Flavonoid glycosides and limonoids from Citrus molasses
- Biotransformation of Benzaldehyde-Type and Acetophenone-Type Derivatives by Pharbitis nil Hairy Roots
- Glucosylation of Phenolic Compounds by Pharbitis nil Hairy Roots : I. Glucosylation of Coumarin and Flavone Derivatives
- Antioxidant Effects of Caesalpinia paraensis Extract on Human Skin Lipid Peroxidation
- The constituents of the roots of Ampelopsis japonica
- Two Phenylpropanoid Glycosides from Neopicrorhiza scrophulariiflora
- Novel A-Seco-Rearranged Lanostane Triterpenoids from Abies sachalinensis
- Fern Constituents : Six New Triterpenoid Alcohols from Adiantum capillus-veneris
- Fern Constituents : Adiantum cuneatum. III. Four New Triterpenoids, 4,23-Bisnor-3,4-secofilic-5(24)-en-3-al, 4,23-Bisnor-3,3-dimethoxy-3,4-secofilic-5(24)-ene, 7β, 25-Epoxyfern-9(11)-en-8α-ol and 7α, 8α-Epoxyfernan-25-ol
- Fern Constituents : Adiantum cuneatum. II. Six New Triterpenoids, Neohop-18-en-12α-ol, 13-Epineohop-18-en-12α-ol, Neohop-13(18)-en-19α-ol, Fern-7-en-25-ol, Fern-9(11)-en-25-ol, and Adian-5-en-25-ol
- Fern Constituents : Adiantum cuneatum. I. Three New Triterpenoids, Glaucanol B Acetate, 7β, 25-Epoxyfern-8-ene and 25-Norfern-7-en-10β-yl Formate
- FERN CONSTITUENTS : TWO NEW SECOFILICANE TRITERPENOIDS FROM ADIANTUM CUNEATUM
- Anti-carcinogenic Activity of Taraxacum Plant. II
- 天然ガムベースサンダラック樹脂の主成分の確認
- Bacopasides III-V : Three New Triterpenoid Glycosides from Bacopa monniera
- New Phenylethanoid Glycosides from Bacopa monniera
- GLYCORIC ACID POSSESSING A NEW 10-NORMEGASTIGMANE SKELETON FROM GLYCOSMIS ARBOREA
- P-445 Molecular Cloning of Squalene Cyclases from Ferns
- Inhibitory effects of terpenes on the growth of Staphylococcus aureus
- Five New Triterpene Saponins, Polygalasaponins XXVIII-XXXII from the Root of Polygala japonica HOUTT.
- Studies on the Constituents of Polygala japonica HOUTT. III. Structures of Polygalasaponins XX-XXVII
- STUDIES ON DIFFERENTIATION INDUCERS FROM PLANTS
- PC84 Isolation of Differentiation Inducers from Plant Sources
- Cell Differentiation Inducers and Antiandrogenic Active Compounds from Zingiberis Rhizoma
- FERN CONSTITUENTS : CYCLOHOPENOL AND CYCLOHOPANEDIOL, NOVEL SKELETAL TRITERPENOIDS FROM RHIZOMES OF PYRROSIA LINGUA
- Fern Constituents : Triterpenoids Isolated from Rhizomes of Pyrrosia lingua. I
- Nine New Triterpene Saponins, Polygalasaponins XXXIII-XLI from the Roots of Polygala fallax HEMSL.
- Cell Differentiation Inducing Steroids from Withania somnifera L. (DUN.)
- Umbelliferone Released from Hairy Root Cultures of Pharbitis nil Treated with Copper Sulfate and Its Subsequent Glucosylation
- Fern Constituents : Sesterterpenoids Isolated from Fronds of Aleuritopteris agetae
- Fern Constituents : Sesterterpenoids Isolated from Fronds of Aleuritopteris mexicana
- Anthocyanin-dimer synthesis in suspension-cultured cells of mutant line of carrot
- Determination of (R)-Xanthoanthrafil, a Phosphodiesterase-5 Inhibitor, in a Dietary Supplement Promoted for Sexual Enhancement
- A New Antifungal Macrolide, Eushearilide, Isolated from Eupenicillium shearii
- Salt-Adaptation of Tobacco BY2 Cells Induces Change in Glycoform of N-Glycans : Enhancement of Exo- and Endo-Glycosidase Activities by Salt-Adaptation
- Composite Constituent: Lactucenyl Acetate, a Novel Migrated Lupane Triterpenoid from Lactuca indica Revision of Structure of Tarolupenyl Acetate
- Identification of a Cannabinoid Analog as a New Type of Designer Drug in a Herbal Product(Communications to the Editor)
- Intracellular and extracellular free N-glycans produced by plant cells : occurrence of unusual plant complex-type free N-glycans in extracellular spaces
- Murine metabolism and absorption of lancemaside A, an active compound in the roots of Codonopsis lanceolata
- A New Acylated Flavonol Glycoside from the Leaves of Eriobotrya japonica
- Inhibitory effects of terpenes on the growth of Staphylococcus aureus
- Anti-Androgen Active Constituents from Dalbergia cochinchinensis PIERRE
- Evaluation of the taste of crude drug and Kampo formula by a taste-sensing system (4) : taste of Processed Aconite Root
- Three new triterpenyl esters, codonopilates A-C, isolated from Codonopsis pilosula
- Study on Aquatic Fern : Terpenoids of Azolla japonica
- Study on Constituents of Latex : Triterpenoids of Euphorbia tirucalli(Natural Medicine Note)
- Chemotaxonomy of Ferns : Triterpenoids and rbcL gene Sequences of Polypodium, Polypodiodes and Goniophlebium
- Fern Constituents : Triterpenoids of Polypodiodes amoena
- Leishmanicidal Active Withanolides from a Pakistani Medicinal Plant, Withania coagulans