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479-98-1,MFCD00136026
Catalog No.:AA0039N7

479-98-1 | (1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl β-D-glucopyranoside

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0039N7
Chemical Name:
(1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl β-D-glucopyranoside
CAS Number:
479-98-1
Molecular Formula:
C15H22O9
Molecular Weight:
346.3298
MDL Number:
MFCD00136026
SMILES:
OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
Properties
Computed Properties
 
Complexity:
507  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
4  
XLogP3:
-3  

Downstream Synthesis Route

[1]Matsueda[NipponKagakuZasshi,1961,vol.82,p.222][Chem.Abstr.,1962,vol.57,p.16428]Fujiseetal.[Chemistryandindustry,1959,p.954][Chem.Abstr.,1962,vol.57,#16428]Fujiseetal.[NipponKagakuZasshi,1961,vol.82,p.221,222][Chem.Abstr.,1962,vol.57,#16428]

[1]Carnevale,Giuseppe;Davini,Enrico;Iavarone,Carlo;Trogolo,Corrado[JournaloftheChemicalSociety.PerkintransactionsI,1990,#4,p.989-992]

[1]Carnevale,Giuseppe;Davini,Enrico;Iavarone,Carlo;Trogolo,Corrado[JournaloftheChemicalSociety.PerkintransactionsI,1990,#4,p.989-992]

[1]Carnevale,Giuseppe;Davini,Enrico;Iavarone,Carlo;Trogolo,Corrado[JournaloftheChemicalSociety.PerkintransactionsI,1990,#4,p.989-992]

[1]Isiguro;Yamaki;Takagi;Ikeda;Kawakami;Ito;Nose[ChemicalandPharmaceuticalBulletin,1986,vol.34,#6,p.2375-2379]

Literature

Title: Involvement of bone morphogenetic protein-related pathways in the effect of aucubin on the promotion of osteoblast differentiation in MG63 cells.

Journal: Chemico-biological interactions 20180301

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Phytochemical analysis of Plantago sempervirens from Majella National Park.

Journal: Natural product research 20121101

Title: HPLC-APCI-MS/MS method for the determination of catalpol in rat plasma and cerebrospinal fluid: application to an in vivo pharmacokinetic study.

Journal: Journal of pharmaceutical and biomedical analysis 20121101

Title: Neuroprotective properties of aucubin in diabetic rats and diabetic encephalopathy rats.

Journal: Molecular biology reports 20121001

Title: A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application.

Journal: Biomedical chromatography : BMC 20120901

Title: The interplay between toxin-releasing β-glucosidase and plant iridoid glycosides impairs larval development in a generalist caterpillar, Grammia incorrupta (Arctiidae).

Journal: Insect biochemistry and molecular biology 20120601

Title: Antiinflammatory activities of Hungarian Stachys species and their iridoids.

Journal: Phytotherapy research : PTR 20120401

Title: Protective effects of aucubin on H₂O₂-induced apoptosis in PC12 cells.

Journal: Phytotherapy research : PTR 20120301

Title: [Enzymatic extraction and antibacterial activity of aucubin from Eucommia ulmoides leaves].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120201

Title: Effect of high relative humidity on dried Plantago lanceolata L. leaves during long-term storage: effects on chemical composition, colour and microbiological quality.

Journal: Phytochemical analysis : PCA 20120101

Title: In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species.

Journal: Phytotherapy research : PTR 20120101

Title: Ixora parviflora Protects against UVB-Induced Photoaging by Inhibiting the Expression of MMPs, MAP Kinases, and COX-2 and by Promoting Type I Procollagen Synthesis.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Diet quality can play a critical role in defense efficacy against parasitoids and pathogens in the Glanville fritillary (Melitaea cinxia).

Journal: Journal of chemical ecology 20120101

Title: Anthelmintic and relaxant activities of Verbascum Thapsus Mullein.

Journal: BMC complementary and alternative medicine 20120101

Title: Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia.

Journal: PloS one 20120101

Title: Major phenolic compounds, antioxidant capacity and antidiabetic potential of rice bean (Vigna umbellata L.) in China.

Journal: International journal of molecular sciences 20120101

Title: Simultaneous determination of four bioactive compounds in Verbena officinalis L. by using high-performance liquid chromatography.

Journal: Pharmacognosy magazine 20120101

Title: Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.

Journal: Journal of pharmaceutical and biomedical analysis 20111215

Title: Iridoid content and biological activities of Veronica cuneifolia subsp. cuneifolia and V. cymbalaria.

Journal: Pharmaceutical biology 20111101

Title: [Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20111001

Title: Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam.

Journal: Journal of ethnopharmacology 20110714

Title: Differential performance of a specialist and two generalist herbivores and their parasitoids on Plantago lanceolata.

Journal: Journal of chemical ecology 20110701

Title: Aucubin modulates Bcl-2 family proteins expression and inhibits caspases cascade in H₂O₂-induced PC12 cells.

Journal: Molecular biology reports 20110601

Title: A comparison of sample preparation techniques for quantifying iridoid glycosides sequestered by lepidopteran larvae.

Journal: Journal of chemical ecology 20110501

Title: Antiprotozoal activity of Melampyrum arvense and its metabolites.

Journal: Phytotherapy research : PTR 20110101

Title: What's in a Name? Can Mullein Weed Beat TB Where Modern Drugs Are Failing?

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Anti-inflammatory and anti-infectious effects of Evodia rutaecarpa (Wuzhuyu) and its major bioactive components.

Journal: Chinese medicine 20110101

Title: The Association between Traditional Chinese Dietary and Herbal Therapies and Uterine Involution in Postpartum Women.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Novel PI3K/Akt inhibitors screened by the cytoprotective function of human immunodeficiency virus type 1 Tat.

Journal: PloS one 20110101

Title: Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonica.

Journal: Biological & pharmaceutical bulletin 20110101

Title: Biological potential of sixteen legumes in China.

Journal: International journal of molecular sciences 20110101

Title: Antidiabetic activity of isoquercetin in diabetic KK -Ay mice.

Journal: Nutrition & metabolism 20110101

Title: Plant community diversity influences allocation to direct chemical defence in Plantago lanceolata.

Journal: PloS one 20110101

Title: [Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101201

Title: A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.

Journal: European journal of medicinal chemistry 20100601

Title: [Studies on the chemical constituents of Buddleja albiflora (II)].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100601

Title: Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro.

Journal: Evidence-based complementary and alternative medicine : eCAM 20100301

Title: Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.

Journal: Journal of chemical ecology 20100201

Title: Curcumin protects intestinal mucosal barrier function of rat enteritis via activation of MKP-1 and attenuation of p38 and NF-κB activation.

Journal: PloS one 20100101

Title: Chungsim-Yeunja-Tang decreases the inflammatory response in peripheral blood mononuclear cells from patients with cerebral infarction through an NF-κB dependent mechanism.

Journal: Journal of neuroinflammation 20100101

Title: Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.

Journal: Journal of ethnobiology and ethnomedicine 20100101

Title: Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101

Title: Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.

Journal: Acta biologica Hungarica 20100101

Title: [The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach].

Journal: Histoire des sciences medicales 20100101

Title: Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.

Journal: Journal of natural products 20091201

Title: X-ray crystal structure of iridoid glucoside aucubin and its aglycone.

Journal: Carbohydrate research 20091102

Title: Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091101

Title: Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds.

Journal: Journal of medicinal food 20090801

Title: [Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090801

Title: Aucubin prevents loss of hippocampal neurons and regulates antioxidative activity in diabetic encephalopathy rats.

Journal: Phytotherapy research : PTR 20090701

Title: Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory.

Journal: Oecologia 20090701

Title: The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L.

Journal: Journal of chemical ecology 20090701

Title: Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.

Journal: Oecologia 20090601

Title: The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells.

Journal: Neurotoxicology 20090501

Title: Iridoids from Euphrasia genargentea, a rare Sardinian endemism.

Journal: Natural product research 20090101

Title: Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20090101

Title: Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.

Journal: Journal of AOAC International 20090101

Title: Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.

Journal: Natural product research 20090101

Title: Chinese medicines as a resource for liver fibrosis treatment.

Journal: Chinese medicine 20090101

Title: A new iridoid glycoside from Scrophularia ningpoensis.

Journal: Natural product research 20090101

Title: Free Radical Scavenging Activity of Calotropis gigantea on Streptozotocin-Induced Diabetic Rats.

Journal: Indian journal of pharmaceutical sciences 20090101

Title: Cytotoxic activities of Stachys species.

Journal: Fitoterapia 20081201

Title: Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.

Journal: Clinical and experimental pharmacology & physiology 20080901

Title: Oviposition cues for a specialist butterfly--plant chemistry and size.

Journal: Journal of chemical ecology 20080901

Title: A potential agent for treating non-small cell lung cancer.

Journal: Clinical and experimental pharmacology & physiology 20080901

Title: Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).

Journal: Phytochemistry 20080801

Title: Neuroprotection of aucubin in primary diabetic encephalopathy.

Journal: Science in China. Series C, Life sciences 20080601

Title: Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.

Journal: Natural product research 20080415

Title: Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.

Journal: European journal of pharmacology 20080317

Title: The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.

Journal: Journal of pharmaceutical and biomedical analysis 20080122

Title: [Research advances in pharmacology of aucubin and aucubigenin].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071201

Title: [Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071101

Title: Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20070601

Title: Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.

Journal: Phytochemistry 20070501

Title: Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.

Journal: Journal of ethnopharmacology 20070404

Title: Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.

Journal: Plant cell reports 20070301

Title: Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.

Journal: Journal of natural products 20070101

Title: Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.

Journal: BMC complementary and alternative medicine 20070101

Title: Overexpression of selenoprotein H reduces Ht22 neuronal cell death after UVB irradiation by preventing superoxide formation.

Journal: International journal of biological sciences 20070101

Title: Effects of aucubin on the healing of oral wounds.

Journal: In vivo (Athens, Greece) 20070101

Title: Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts.

Journal: Nutrition research and practice 20070101

Title: Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.

Journal: Natural product research 20060510

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: A validation protocol for the HPTLC standardization of herbal products: application to the determination of acteoside in leaves of Plantago palmata Hook. f.s.

Journal: Talanta 20060415

Title: Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.

Journal: Phytochemistry 20060201

Title: Antioxidant activity of Plantago bellardii All.

Journal: Phytotherapy research : PTR 20051201

Title: Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts.

Journal: Bioscience, biotechnology, and biochemistry 20051101

Title: [Study on the chemical constituents of Buddleja purdomii].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20051101

Title: Iridoids as DNA topoisomerase I poisons.

Journal: Journal of enzyme inhibition and medicinal chemistry 20050801

Title: Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.

Journal: Biological & pharmaceutical bulletin 20050701

Title: Chemotaxonomic markers in Digitalideae (Plantaginaceae).

Journal: Phytochemistry 20050601

Title: Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.

Journal: Chemistry & biodiversity 20050501

Title: Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.

Journal: Phytochemistry 20050201

Title: On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR.

Journal: Phytochemical analysis : PCA 20050101

Title: [Study on optimizing the analysis condition for active compound in Eucommia olive].

Journal: Guang pu xue yu guang pu fen xi = Guang pu 20041201

Title: Patterns of iridoid glycoside production and induction in Plantago lanceolata and the importance of plant age.

Journal: Journal of chemical ecology 20040901

Title: Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?

Journal: Oecologia 20040801

Title: Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells.

Journal: Planta medica 20040801

Title: Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.

Journal: Phytochemistry 20040701

Title: Earthworms and litter distribution affect plant-defensive chemistry.

Journal: Journal of chemical ecology 20040401

Title: Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20040101

Title: Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition.

Journal: Archives of pharmacal research 20031101

Title: Aragoside and iridoid glucosides from Aragoa cundinamarcensis.

Journal: Phytochemistry 20030901

Title: Determination of iridoid glycosides in larvae and adults of butterfly Melitaea cinxia by partial filling micellar electrokinetic capillary chromatography-electrospray ionisation mass spectrometry.

Journal: Analytical and bioanalytical chemistry 20030701

Title: Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.

Journal: Planta medica 20030701

Title: Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.

Journal: Journal of chemical ecology 20030401

Title: Complement-inhibiting iridoids from Morinda morindoides.

Journal: Journal of natural products 20030101

Title: Iridoids from Globularia dumulosa.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: Antileukemic activity of selected natural products in Taiwan.

Journal: The American journal of Chinese medicine 20030101

Title: Iridoid and bisiridoid glycosides from Globularia cordifolia.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: Iridoid glucosides from Veronica pectinata var. glandulosa.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: Systemic, genotype-specific induction of two herbivore-deterrent iridoid glycosides in Plantago lanceolata L. in response to fungal infection by Diaporthe adunca (Rob.) Niessel.

Journal: Journal of chemical ecology 20021201

Title: Iridoid glucosides from Veronica hederifolia.

Journal: Chemical & pharmaceutical bulletin 20020801

Title: Antiviral activity of Plantago major extracts and related compounds in vitro.

Journal: Antiviral research 20020701

Title: Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells.

Journal: Cytokine 20020607

Title: Phenylethanoid and iridoid glycosides from Veronica persica.

Journal: Chemical & pharmaceutical bulletin 20020601

Title: Changes in the concentrations of bioactive compounds in plantain leaves.

Journal: Journal of agricultural and food chemistry 20020424

Title: Iridoid patterns of genus Plantago L. and their systematic significance.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

Title: Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique.

Journal: Electrophoresis 20010801

Title: Studies on the possible mechanisms of protective activity against alpha-amanitin poisoning by aucubin.

Journal: Archives of pharmacal research 20010201

Title: Iridoid glycosides from Globularia trichosantha.

Journal: Journal of natural products 20010101

Title: Jin l, et, al. Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes. Eur J Pharmacol. 2008 Mar 17;582(1-3):162-7.

Title: Jeong HJ, et, al. Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells. Cytokine. 2002 Jun 7;18(5):252-9.

Title: Zeng X, et, al. A review of the pharmacology and toxicology of aucubin. Fitoterapia. 2020 Jan;140:104443.

Title: Xue HY, et, al. Protective effects of aucubin on H₂O₂-induced apoptosis in PC12 cells. Phytother Res. 2012 Mar;26(3):369-74.

Title: Chang LM, et, al. Aucubin: potential antidote for alpha-amanitin poisoning. J Toxicol Clin Toxicol. 1984 Jul;22(1):77-85.

Title: Zhou Y, et, al. Aucubin Alleviates Bleomycin-Induced Pulmonary Fibrosis in a Mouse Model. Inflammation. 2017 Dec;40(6):2062-2073.

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SDS
Tags:479-98-1 Molecular Formula|479-98-1 MDL|479-98-1 SMILES|479-98-1 (1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl β-D-glucopyranoside