EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(-)-maackiain

Supplier Sponsors

CAS Number: 2035-15-6Picture of molecule3D/inchi
FDA UNII: TF360D25IJ
Nikkaji Web:J14.944F
XlogP3:2.50 (est)
Molecular Weight:284.26764000
Formula:C16 H12 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 339.9 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Maackiain > 95%
Odor: characteristic
Use: Maackiain isolated from the flowers of Maackia amurensis Rupr.et Maxim. antifungal;
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (-)-maackiain usage levels up to:
 not for fragrance use.
 
Recommendation for (-)-maackiain flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91510
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0002035156
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):91510
Pubchem (cas):2035-15-6
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10502
HMDB (The Human Metabolome Database):HMDB36629
FooDB:FDB015548
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 trifolium pratense
Search Trop Picture
 
Synonyms:
6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-
 

Articles:

PubMed:[Simultaneous determination of seven alkaloids and three flavonoids in Sophorae Tonkinensis Radix et Rhizoma by HPLC].
PubMed:SKI3301, a purified herbal extract from Sophora tonkinensis, inhibited airway inflammation and bronchospasm in allergic asthma animal models in vivo.
PubMed:Chemical constituents from Sophora tonkinensis and their glucose transporter 4 translocation activities.
PubMed:In vitro and in silico characterization of angiogenic inhibitors from Sophora interrupta.
PubMed:Chemical profiling of anti-hepatocellular carcinoma constituents from Caragana tangutica Maxim. by off-line semi-preparative HPLC-NMR.
PubMed:Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens.
PubMed:Flavonoids from Cyclopia genistoides and Their Xanthine Oxidase Inhibitory Activity.
PubMed:[Chemical constituents from EtOAc fraction of Sophora dunnii].
PubMed:[Molecular pharmacology of (-)maackiain, from Kujin, an anti-allergic Kampo medicine].
PubMed:Chemical study of the Chinese medicine Pi Han Yao.
PubMed:Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC-MS/MS and NMR.
PubMed:Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes.
PubMed:Improvement of androgenetic alopecia with topical Sophora flavescens Aiton extract, and identification of the two active compounds in the extract that stimulate proliferation of human hair keratinocytes.
PubMed:Disruption of Heat Shock Protein 90 (Hsp90)-Protein Kinase Cδ (PKCδ) Interaction by (-)-Maackiain Suppresses Histamine H1 Receptor Gene Transcription in HeLa Cells.
PubMed:Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
PubMed:Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B).
PubMed:Pharmacokinetic properties of trifolirhizin, (-)-maackiain, (-)-sophoranone and 2-(2,4-dihydroxyphenyl)-5,6-methylenedioxybenzofuran after intravenous and oral administration of Sophora tonkinensis extract in rats.
PubMed:Ultrasound-assisted dynamic extraction coupled with parallel countercurrent chromatography for simultaneous extraction, purification, and isolation of phytochemicals: application to isoflavones from red clover.
PubMed:Extract of Bowdichia virgilioides and maackiain as larvicidal agent against Aedes aegypti mosquito.
PubMed:Inhibitory constituents of Sophora tonkinensis on nitric oxide production in RAW 264.7 macrophages.
PubMed:Antitumor and apoptotic activities of the chemical constituents from the ethyl acetate extract of Artemisia indica.
PubMed:Simultaneous determination of trifolirhizin, (-)-maackiain, (-)-sophoranone, and 2-(2,4-dihydroxyphenyl)-5,6-methylenedioxybenzofuran from Sophora tonkinensis in rat plasma by liquid chromatography with tandem mass spectrometry and its application to a pharmacokinetic study.
PubMed:[Simultaneous determination of 4 alkaloids and a flavonoid in Picrasmae Ramulus et Folium by RP-HPLC].
PubMed:Qualitative and quantitative analysis of flavonoids in Sophora tonkinensis by LC/MS and HPLC.
PubMed:(+)-Pisatin biosynthesis: from (-) enantiomeric intermediates via an achiral 7,2'-dihydroxy-4',5'-methylenedioxyisoflav-3-ene.
PubMed:[HPLC fingerprint of flavonoids in Sophora flavescens and determination of five components].
PubMed:[Chemical constituents from aerial part of Rumex patientia].
PubMed:Phytotoxic allelochemicals from roots and root exudates of Trifolium pratense.
PubMed:Chemopreventive effect of a mixture of Chinese Herbs (antitumor B) on chemically induced oral carcinogenesis.
PubMed:LC-ESI-MS characterisation of phytoalexins induced in chickpea and pea tissues in response to a biotic elicitor of Hypnea musciformis (red algae).
PubMed:[Chemical constituents of Ammopiptanthus mongolicus].
PubMed:[Study on chemical constituents of Picrasma quassioides].
PubMed:Validated LC-MS/MS method for the determination of maackiain and its sulfate and glucuronide in blood: application to pharmacokinetic and disposition studies.
PubMed:[Chemical constituents of Indigofera pseudotinctoria].
PubMed:Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707.
PubMed:Red clover (Trifolium pratense L.) isoflavones: root phenolic compounds affected by biotic and abiotic stress factors.
PubMed:[Studies on chemical constituents of root of Millettia speciosa].
PubMed:[Chemical constituents of Oxytropis falcate].
PubMed:Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.
PubMed:Bioassay-guided fractionation of pterocarpans from roots of Harpalyce brasiliana Benth.
PubMed:Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry.
PubMed:A novel isoflavonoid from Millettia puguensis.
PubMed:Studies on the late steps of (+) pisatin biosynthesis: evidence for (-) enantiomeric intermediates.
PubMed:Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.
PubMed:Binding of flavonoids from Sophora flavescens to the rat uterine estrogen receptor.
PubMed:In vitro free radical and ONOO- scavengers from Sophora flavescens.
PubMed:Maackiain 3-O-(6'-O-malonyl-beta-D-glucopyranoside) from Oudneya africana, a powerful inhibitor of porcine kidney acylase I.
PubMed:Induction of apoptosis by maackiain and trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) in human promyelotic leukemia HL-60 cells.
PubMed:Flavonoids from Spatholobus suberectus.
PubMed:A new pterocarpan, (-)-maackiain sulfate, from the roots of Sophora subprostrata.
PubMed:A new prenylisoflavone from Ulex jussiaei.
PubMed:A new coumaronochromone from Sophora japonica.
PubMed:Macharistol, a new cytotoxic cinnamylphenol from the stems of Machaerium aristulatum.
PubMed:Anti-amoebic activity of plant compounds from Virgilia oroboides and Chlorophora excelsa.
PubMed:Functional expression and subcellular localization of the Nectria haematococca Mak1 phytoalexin detoxification enzyme in transgenic tobacco.
PubMed:Effects of isoflavonoids from Cicer on larvae of Heliocoverpa armigera.
PubMed:Phenolic constituents of Ononis vaginalis roots.
PubMed:Elicitor-induced changes in isoflavonoid metabolism in red clover roots.
PubMed:Induction of clovamide by jasmonic acid in red clover.
PubMed:Antimalarial principles from Artemisia indica.
PubMed:Effects of pisatin on Dictyostelium discoideum: its relationship to inducible resistance to nystatin and extension to other isoflavonoid phytoalexins.
PubMed:Manuifolins D, E, and F: new isoflavonoids from Maackia tenuifolia.
PubMed:Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase.
PubMed:Oxidation of the phytoalexin maackiain to 6,6-dihydroxy-maackiain by Colletotrichum gloeosporioides.
PubMed:A gene for maackiain detoxification from a dispensable chromosome of Nectria haematococca.
PubMed:Isolation and structure identification of an active DNA strand-scission agent, (+)-3,4-di-hydroxy-8,9-methylenedioxypterocarpan.
PubMed:Genetic Analysis of the Role of Phytoalexin Detoxification in Virulence of the Fungus Nectria haematococca on Chickpea (Cicer arietinum).
PubMed:Three Genes for Metabolism of the Phytoalexin Maackiain in the Plant Pathogen Nectria haematococca: Meiotic Instability and Relationship to a New Gene for Pisatin Demethylase.
PubMed:Medicarpin and maackiain 3-O-glucoside-6'-O-malonate conjugates are constitutive compounds in chickpea (Cicer arietinum L.) cell cultures.
PubMed:Biosynthesis of the Phytoalexin Pisatin : Isoflavone Reduction and Further Metabolism of the Product Sophorol by Extracts of Pisum sativum.
PubMed:Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabiei : II. Differential induction of chalcone-synthase-mRNA activity and analysis of in-vitro-translated protein patterns.
PubMed:Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabiei : I. Investigations of enzyme activities involved in isoflavone and pterocarpan phytoalexin biosynthesis.
PubMed:Accumulation of isoflavones and pterocarpan phytoalexins in cell suspension cultures of different cultivars of chickpea (Cicer arietinum).
PubMed:Role of oxygenases in pisatin biosynthesis and in the fungal degradation of maackiain.
PubMed:The effect of the phytoalexins, lubimin, (-)-maackiain, pinosylvin, and the related compounds dehydroloroglossol and hordatine M on human lymphoblastoid cell lines.
PubMed:Synthesis of the phytoalexin pisatin by a methyltransferase from pea.
PubMed:Flavone modulators of rat hepatic aryl hydrocarbon hydroxylase.
PubMed:Specificity of medicarpin and related isoflavonoids in inhibition of rat hepatic mixed function oxidase activity.
PubMed:(-)Maackiain acetate specifically inhibits different forms of aryl hydrocarbon hydroxylase in rat and man.
PubMed:Sensitivity of Rhizobium to selected isoflavonoids.
PubMed:Susceptibility of zoopathogenic fungi to phytoalexins.
PubMed:The presence of L-maackiain and pterocarpin in callus tissue of Sophora angustifolia.
PubMed:Oxygen heterocycles. Maackiain, a new naturally occuring chromanocoumaran.
 
Notes:
None found
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