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479-98-1

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

CAS No: 479-98-1 Catalog No: AG0039PZ MDL No:MFCD00136026

Product Description

Catalog Number:
AG0039PZ
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
IUPAC Name:
(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
InChI:
InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
InChI Key:
RJWJHRPNHPHBRN-FKVJWERZSA-N
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
EC Number:
207-540-8
UNII:
2G52GS8UML

Properties

Complexity:
507  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
346.126g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
346.332g/mol
Monoisotopic Mass:
346.126g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
149A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3  

Literature

Title Journal
Involvement of bone morphogenetic protein-related pathways in the effect of aucubin on the promotion of osteoblast differentiation in MG63 cells. Chemico-biological interactions 20180301
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
Phytochemical analysis of Plantago sempervirens from Majella National Park. Natural product research 20121101
HPLC-APCI-MS/MS method for the determination of catalpol in rat plasma and cerebrospinal fluid: application to an in vivo pharmacokinetic study. Journal of pharmaceutical and biomedical analysis 20121101
Neuroprotective properties of aucubin in diabetic rats and diabetic encephalopathy rats. Molecular biology reports 20121001
A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application. Biomedical chromatography : BMC 20120901
The interplay between toxin-releasing β-glucosidase and plant iridoid glycosides impairs larval development in a generalist caterpillar, Grammia incorrupta (Arctiidae). Insect biochemistry and molecular biology 20120601
Antiinflammatory activities of Hungarian Stachys species and their iridoids. Phytotherapy research : PTR 20120401
Protective effects of aucubin on H₂O₂-induced apoptosis in PC12 cells. Phytotherapy research : PTR 20120301
[Enzymatic extraction and antibacterial activity of aucubin from Eucommia ulmoides leaves]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120201
Effect of high relative humidity on dried Plantago lanceolata L. leaves during long-term storage: effects on chemical composition, colour and microbiological quality. Phytochemical analysis : PCA 20120101
In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species. Phytotherapy research : PTR 20120101
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. Evidence-based complementary and alternative medicine : eCAM 20120101
Diet quality can play a critical role in defense efficacy against parasitoids and pathogens in the Glanville fritillary (Melitaea cinxia). Journal of chemical ecology 20120101
Anthelmintic and relaxant activities of Verbascum Thapsus Mullein. BMC complementary and alternative medicine 20120101
Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia. PloS one 20120101
Major phenolic compounds, antioxidant capacity and antidiabetic potential of rice bean (Vigna umbellata L.) in China. International journal of molecular sciences 20120101
Simultaneous determination of four bioactive compounds in Verbena officinalis L. by using high-performance liquid chromatography. Pharmacognosy magazine 20120101
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. Journal of pharmaceutical and biomedical analysis 20111215
Iridoid content and biological activities of Veronica cuneifolia subsp. cuneifolia and V. cymbalaria. Pharmaceutical biology 20111101
[Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum]. Yao xue xue bao = Acta pharmaceutica Sinica 20111001
Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam. Journal of ethnopharmacology 20110714
Differential performance of a specialist and two generalist herbivores and their parasitoids on Plantago lanceolata. Journal of chemical ecology 20110701
Aucubin modulates Bcl-2 family proteins expression and inhibits caspases cascade in H₂O₂-induced PC12 cells. Molecular biology reports 20110601
A comparison of sample preparation techniques for quantifying iridoid glycosides sequestered by lepidopteran larvae. Journal of chemical ecology 20110501
Antiprotozoal activity of Melampyrum arvense and its metabolites. Phytotherapy research : PTR 20110101
What's in a Name? Can Mullein Weed Beat TB Where Modern Drugs Are Failing? Evidence-based complementary and alternative medicine : eCAM 20110101
Anti-inflammatory and anti-infectious effects of Evodia rutaecarpa (Wuzhuyu) and its major bioactive components. Chinese medicine 20110101
The Association between Traditional Chinese Dietary and Herbal Therapies and Uterine Involution in Postpartum Women. Evidence-based complementary and alternative medicine : eCAM 20110101
Novel PI3K/Akt inhibitors screened by the cytoprotective function of human immunodeficiency virus type 1 Tat. PloS one 20110101
Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonica. Biological & pharmaceutical bulletin 20110101
Biological potential of sixteen legumes in China. International journal of molecular sciences 20110101
Antidiabetic activity of isoquercetin in diabetic KK -Ay mice. Nutrition & metabolism 20110101
Plant community diversity influences allocation to direct chemical defence in Plantago lanceolata. PloS one 20110101
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101201
A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships. European journal of medicinal chemistry 20100601
[Studies on the chemical constituents of Buddleja albiflora (II)]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100601
Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro. Evidence-based complementary and alternative medicine : eCAM 20100301
Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants. Journal of chemical ecology 20100201
Curcumin protects intestinal mucosal barrier function of rat enteritis via activation of MKP-1 and attenuation of p38 and NF-κB activation. PloS one 20100101
Chungsim-Yeunja-Tang decreases the inflammatory response in peripheral blood mononuclear cells from patients with cerebral infarction through an NF-κB dependent mechanism. Journal of neuroinflammation 20100101
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. Journal of ethnobiology and ethnomedicine 20100101
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites. Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101
Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity. Acta biologica Hungarica 20100101
[The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach]. Histoire des sciences medicales 20100101
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album. Journal of natural products 20091201
X-ray crystal structure of iridoid glucoside aucubin and its aglycone. Carbohydrate research 20091102
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091101
Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds. Journal of medicinal food 20090801
[Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090801
Aucubin prevents loss of hippocampal neurons and regulates antioxidative activity in diabetic encephalopathy rats. Phytotherapy research : PTR 20090701
Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory. Oecologia 20090701
The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L. Journal of chemical ecology 20090701
Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L. Oecologia 20090601
The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. Neurotoxicology 20090501
Iridoids from Euphrasia genargentea, a rare Sardinian endemism. Natural product research 20090101
Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour. Zeitschrift fur Naturforschung. C, Journal of biosciences 20090101
Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide. Journal of AOAC International 20090101
Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis. Natural product research 20090101
Chinese medicines as a resource for liver fibrosis treatment. Chinese medicine 20090101
A new iridoid glycoside from Scrophularia ningpoensis. Natural product research 20090101
Free Radical Scavenging Activity of Calotropis gigantea on Streptozotocin-Induced Diabetic Rats. Indian journal of pharmaceutical sciences 20090101
Cytotoxic activities of Stachys species. Fitoterapia 20081201
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells. Clinical and experimental pharmacology & physiology 20080901
Oviposition cues for a specialist butterfly--plant chemistry and size. Journal of chemical ecology 20080901
A potential agent for treating non-small cell lung cancer. Clinical and experimental pharmacology & physiology 20080901
Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae). Phytochemistry 20080801
Neuroprotection of aucubin in primary diabetic encephalopathy. Science in China. Series C, Life sciences 20080601
Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt. Natural product research 20080415
Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes. European journal of pharmacology 20080317
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues. Journal of pharmaceutical and biomedical analysis 20080122
[Research advances in pharmacology of aucubin and aucubigenin]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071201
[Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071101
Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds. Phytomedicine : international journal of phytotherapy and phytopharmacology 20070601
Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana. Phytochemistry 20070501
Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham. Journal of ethnopharmacology 20070404
Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L. Plant cell reports 20070301
Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues. Journal of natural products 20070101
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides. BMC complementary and alternative medicine 20070101
Overexpression of selenoprotein H reduces Ht22 neuronal cell death after UVB irradiation by preventing superoxide formation. International journal of biological sciences 20070101
Effects of aucubin on the healing of oral wounds. In vivo (Athens, Greece) 20070101
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts. Nutrition research and practice 20070101
Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata. Natural product research 20060510
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
A validation protocol for the HPTLC standardization of herbal products: application to the determination of acteoside in leaves of Plantago palmata Hook. f.s. Talanta 20060415
Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae. Phytochemistry 20060201
Antioxidant activity of Plantago bellardii All. Phytotherapy research : PTR 20051201
Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts. Bioscience, biotechnology, and biochemistry 20051101
[Study on the chemical constituents of Buddleja purdomii]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20051101
Iridoids as DNA topoisomerase I poisons. Journal of enzyme inhibition and medicinal chemistry 20050801
Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts. Biological & pharmaceutical bulletin 20050701
Chemotaxonomic markers in Digitalideae (Plantaginaceae). Phytochemistry 20050601
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin. Chemistry & biodiversity 20050501
Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots. Phytochemistry 20050201
On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR. Phytochemical analysis : PCA 20050101
[Study on optimizing the analysis condition for active compound in Eucommia olive]. Guang pu xue yu guang pu fen xi = Guang pu 20041201
Patterns of iridoid glycoside production and induction in Plantago lanceolata and the importance of plant age. Journal of chemical ecology 20040901
Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs? Oecologia 20040801
Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells. Planta medica 20040801
Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica. Phytochemistry 20040701
Earthworms and litter distribution affect plant-defensive chemistry. Journal of chemical ecology 20040401
Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography. Zeitschrift fur Naturforschung. C, Journal of biosciences 20040101
Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition. Archives of pharmacal research 20031101
Aragoside and iridoid glucosides from Aragoa cundinamarcensis. Phytochemistry 20030901
Determination of iridoid glycosides in larvae and adults of butterfly Melitaea cinxia by partial filling micellar electrokinetic capillary chromatography-electrospray ionisation mass spectrometry. Analytical and bioanalytical chemistry 20030701
Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. Planta medica 20030701
Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore. Journal of chemical ecology 20030401
Complement-inhibiting iridoids from Morinda morindoides. Journal of natural products 20030101
Iridoids from Globularia dumulosa. Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101
Antileukemic activity of selected natural products in Taiwan. The American journal of Chinese medicine 20030101
Iridoid and bisiridoid glycosides from Globularia cordifolia. Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101
Iridoid glucosides from Veronica pectinata var. glandulosa. Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101
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 of chemical ecology 20021201
Iridoid glucosides from Veronica hederifolia. Chemical & pharmaceutical bulletin 20020801
Antiviral activity of Plantago major extracts and related compounds in vitro. Antiviral research 20020701
Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells. Cytokine 20020607
Phenylethanoid and iridoid glycosides from Veronica persica. Chemical & pharmaceutical bulletin 20020601
Changes in the concentrations of bioactive compounds in plantain leaves. Journal of agricultural and food chemistry 20020424
Iridoid patterns of genus Plantago L. and their systematic significance. Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101
Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique. Electrophoresis 20010801
Studies on the possible mechanisms of protective activity against alpha-amanitin poisoning by aucubin. Archives of pharmacal research 20010201
Iridoid glycosides from Globularia trichosantha. Journal of natural products 20010101

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