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alpha-hederin hydrate
23-hydroxy-3b-[(O-a-L-rhamnopyranosyl-(1->2)-a-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid

Supplier Sponsors

CAS Number: 27013-91-8Picture of molecule3D/inchi
Other(deleted CASRN):104748-88-1
ECHA EINECS - REACH Pre-Reg:248-166-5
FDA UNII: 4H15F0GLV2
Nikkaji Web:J17.197B
Beilstein Number:0076156
MDL:MFCD00010665
XlogP3-AA:3.60 (est)
Molecular Weight:750.96742000
Formula:C41 H66 O12
BioActivity Summary:listing
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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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 261.00 °C. @ 760.00 mm Hg
Boiling Point: 849.60 °C. @ 760.00 mm Hg (est)
Flash Point: 483.00 °F. TCC ( 250.70 °C. ) (est)
logP (o/w): 8.370 (est)
Soluble in:
 water, 0.006577 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Hederin, alpha- 98%
BOC Sciences
For experimental / research use only.
a-Hederin >=98%
Odor: characteristic
Use: à-Hederin isolated from the herbs of Hedera nepalensis. It is a haemolytic agent. anti-inflammatory activity; molluscicidal activity and antifungal activity
Coompo
For experimental / research use only.
alpha-Hederin from Plants ≥96%
ExtraSynthese
For experimental / research use only.
alpha-Hederin (HPLC) ≥98%
Sigma-Aldrich
For experimental / research use only.
a-Hederin analytical standard
 
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:
intraperitoneal-mouse LD50 1800 mg/kg
Annales Pharmaceutiques Francaises. Vol. 38, Pg. 545, 1980.

oral-mouse LD50 > 4000 mg/kg
Annales Pharmaceutiques Francaises. Vol. 38, Pg. 545, 1980.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for alpha-hederin hydrate usage levels up to:
 not for fragrance use.
 
Recommendation for alpha-hederin hydrate 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 :73296
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0027013918
RTECS:RK0177800 for cas# 27013-91-8
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73296
Pubchem (sid):135030199
 
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):C08954
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 ivy
Search PMC Picture
 
Synonyms:
(4a)-3b-((2-O-(6-deoxy-a-L-mannopyranosyl)-a-L-arabinopyranosyl)oxy)-23-hydroxyolean-12-en-28-oic acid
(4a)-3b-[[2-O-(6-deoxy-a-L-mannopyranosyl)-a-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid
(3b)-3-{[2-O-(6-deoxy-a-L-mannopyranosyl)-a-L-arabinopyranosyl]oxy}-23-hydroxyolean-12-en-28-oic acid
(4alpha)-3beta-((2-O-(6-deoxy-alpha-laevo-mannopyranosyl)-alpha-laevo-arabinopyranosyl)oxy)-23-hydroxyolean-12-en-28-oic acid
 glycoside L-E1
a-hederin (8CI)
alpha-hederin hydrate
 hederoside C
23-hydroxy-3b-[(O-a-L-rhamnopyranosyl-(1->2)-a-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid
 kalopanaxsaponin A
 koronaroside A
 nepalin 2
 olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-a-L-mannopyranosyl)-a-L-arabinopyranosyl]oxy]-23-hydroxy-, (3b)-
 pulsatilla saponin A
 sapindoside A
 tauroside e
 

Articles:

PubMed:Determination of Saponins and Flavonoids in Ivy Leaf Extracts Using HPLC-DAD.
PubMed:The anticancer effect and mechanism of α-hederin on breast cancer cells.
PubMed:Domain formation and permeabilization induced by the saponin α-hederin and its aglycone hederagenin in a cholesterol-containing bilayer.
PubMed:The apoptotic effect of D Rhamnose β-Hederin, a novel oleanane-type triterpenoid saponin on breast cancer cells.
PubMed:Cytotoxicity and modes of action of five Cameroonian medicinal plants against multi-factorial drug resistance of tumor cells.
PubMed:The haploinsufficiency profile of α-hederin suggests a caspofungin-like antifungal mode of action.
PubMed:Kalopanaxsaponin A Exerts Anti-Inflammatory Effects in Lipopolysaccharide-Stimulated Microglia via Inhibition of JNK and NF-κB/AP-1 Pathways.
PubMed:Induction of highly curved structures in relation to membrane permeabilization and budding by the triterpenoid saponins, α- and δ-Hederin.
PubMed:Participation of extracellular calcium in α-hederin-induced contractions of rat isolated stomach strips.
PubMed:Methyl syringate, a low-molecular-weight phenolic ester, as an activator of the chemosensory ion channel TRPA1.
PubMed:Synthesis of novel diosgenyl saponin analogues and apoptosis-inducing activity on A549 human lung adenocarcinoma.
PubMed:Distribution of primary and specialized metabolites in Nigella sativa seeds, a spice with vast traditional and historical uses.
PubMed:Participation of cholinergic pathways in α-hederin-induced contraction of rat isolated stomach strips.
PubMed:Kalopanaxsaponin A inhibits the invasion of human oral squamous cell carcinoma by reducing metalloproteinase-9 mRNA stability and protein trafficking.
PubMed:[Mass spectrometry of triterpene glycosides molecular complexation with purine bases of nucleic acids].
PubMed:HPLC-PDA method for quinovic acid glycosides assay in Cat's claw (Uncaria tomentosa) associated with UPLC/Q-TOF-MS analysis.
PubMed:Anticancer activity of Nigella sativa (black seed) - a review.
PubMed:The effect of the whole extract of common ivy (Hedera helix) leaves and selected active substances on the motoric activity of rat isolated stomach strips.
PubMed:Kalopanaxsaponin A ameliorates experimental colitis in mice by inhibiting IRAK-1 activation in the NF-κB and MAPK pathways.
PubMed:Synthesis and tumor cytotoxicity of novel amide derivatives of β-hederin.
PubMed:Nigella sativa: reduces the risk of various maladies.
PubMed:Pre-treatment with α-hederin increases β-adrenoceptor mediated relaxation of airway smooth muscle.
PubMed:African descents are more sensitive than European descents to the antitumor compounds α-hederin and kalopanaxsaponin I.
PubMed:Rapid quantification of 14 saponins of Maesa lanceolata by UPLC-MS/MS.
PubMed:Resistance in the plant, Barbarea vulgaris, and counter-adaptations in flea beetles mediated by saponins.
PubMed:Triterpenoid saponins from the stems of Clematis parviloba.
PubMed:Kalopanaxsaponin A inhibits PMA-induced invasion by reducing matrix metalloproteinase-9 via PI3K/Akt- and PKCdelta-mediated signaling in MCF-7 human breast cancer cells.
PubMed:Methyl jasmonate induced accumulation of kalopanaxsaponin I in Nigella sativa.
PubMed:Alpha-hederin, but not hederacoside C and hederagenin from Hedera helix, affects the binding behavior, dynamics, and regulation of beta 2-adrenergic receptors.
PubMed:Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.
PubMed:Biologically active triterpenoids from Cephalaria ambrosioides.
PubMed:Kalopanaxsaponin A induces apoptosis in human leukemia U937 cells through extracellular Ca2+ influx and caspase-8 dependent pathways.
PubMed:Alpha-hederin potentiates 5-FU antitumor activity in human colon adenocarcinoma cells.
PubMed:A convenient preparation of a disaccharide motif and its role in the cytotoxicity of the triterpenoid saponin, alpha-hederin.
PubMed:Structure-activity relationships of some hederagenin diglycosides: haemolysis, cytotoxicity and apoptosis induction.
PubMed:Modes of action of alpha-hederin and thymoquinone, active constituents of Nigella sativa, against HEp-2 cancer cells.
PubMed:Synthesis of beta-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety.
PubMed:[Studies on chemical constituents in the seeds of Nigella glandulifera].
PubMed:Effects of alpha-hederin and thymoquinone, constituents of Nigella sativa, on human cancer cell lines.
PubMed:Involvement of cytokines in the hepatic metallothionein expression by alpha-hederin.
PubMed:Acute anti-inflammatory activity of four saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F in carrageenan-induced rat paw edema.
PubMed:Saponins and other constituents from the leaves of Aralia elata.
PubMed:Antinociceptive and anti-inflammatory effects of the saponin and sapogenins obtained from the stem of Akebia quinata.
PubMed:Simultaneous determination of glycyrrhizin, a marker component in radix Glycyrrhizae, and its major metabolite glycyrrhetic acid in human plasma by LC-MS/MS.
PubMed:HPLC profiling and quantification of active principles in leaves of Hedera helix L.
PubMed:Evaluation of bioactive saponins and triterpenoidal aglycons for their binding properties on human endothelin ETA and angiotensin AT1 receptors.
PubMed:Antioxidant activity of saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F.
PubMed:Dynamics of beta2-adrenergic receptor-ligand complexes on living cells.
PubMed:Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition.
PubMed:An unusual case of death: suffocation caused by leaves of common ivy (Hedera helix). Detection of hederacoside C, alpha-hederin, and hederagenin by LC-EI/MS-MS.
PubMed:Intracellular glutathione depletion and reactive oxygen species generation are important in alpha-hederin-induced apoptosis of P388 cells.
PubMed:Antiinflammatory activity of alpha-hederin methyl ester from the alkaline hydrolysate of the butanol fraction of Kalopanax pictus bark extract.
PubMed:Activity-guided isolation of saponins from Kalopanax pictus with anti-inflammatory activity.
PubMed:Expression of inducible nitric oxide synthase by alpha-hederin in macrophages.
PubMed:In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells.
PubMed:Metabolism of kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites.
PubMed:Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals.
PubMed:Anti-lipid peroxidative principles from the stem bark of Kalopanax pictus Nakai.
PubMed:Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent.
PubMed:Triterpenoid saponins from Clematis tangutica.
PubMed:In vitro antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A(1), in association with pentamidine and amphotericin B.
PubMed:[In vitro study of the antimutagenic activity of alphahederin].
PubMed:Triterpenoid saponins from the stem bark of Elattostachys apetala.
PubMed:Toxicology of Kalopanax pictus extract and hematological effect of the isolated anti-rheumatoidal kalopanaxsaponin A on the Freunds complete adjuvant reagent-treated rat.
PubMed:Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides.
PubMed:Extraction, isolation and characterisation of antitumor principle, alpha-hederin, from the seeds of Nigella sativa.
PubMed:Antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A1, as compared to their action on mammalian cells cultured in vitro.
PubMed:Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides and bisdesmosides isolated from the stem bark of Kalopanax pictus.
PubMed:The protective activity of alpha-hederine against H2O2 genotoxicity in HepG2 cells by alkaline comet assay.
PubMed:Suppressive effects of alpha-Hederin on 2,3,7,8-tetrachlorodibenzo-p-dioxin-mediated murine Cyp1a-1 expression in the mouse hepatoma Hepa-1c1c7 cells.
PubMed:Chitin synthase II inhibitory activity of ursolic acid, isolated from Crataegus pinnatifida.
PubMed:Study of the action of alpha-hederin on the ultrastructure of Candida albicans.
PubMed:A potent anti-diabetic agent from Kalopanax pictus.
PubMed:Growth inhibitory activities of kalopanaxsaponins A and I against human pathogenic fungi.
PubMed:Suppression of constitutive and inducible cytochrome P450 gene expression by alpha-hederin in mice.
PubMed:The prevention of carbon tetrachloride-induced hepatotoxicity in mice by alpha-hederin: inhibiton of cytochrome P450 2E1 expression.
PubMed:Metabolism of kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites.
PubMed:Repeated administration of alpha-hederin results in alterations in maternal zinc status and adverse developmental outcome in the rat.
PubMed:In vitro antispasmodic compounds of the dry extract obtained from Hedera helix.
PubMed:Effect of alpha-hederin on hepatic detoxifying systems in mice.
PubMed:Effect of alpha-hederin and sapindoside B on hepatic microsomal cytochrome P-450 in mice.
PubMed:Protective effects of alpha-hederin, chlorophyllin and ascorbic acid towards the induction of micronuclei by doxorubicin in cultured human lymphocytes.
PubMed:Effect of several metallothionein inducers on oxidative stress defense mechanisms in rats.
PubMed:Anti-elastase and anti-hyaluronidase activities of saponins and sapogenins from Hedera helix, Aesculus hippocastanum, and Ruscus aculeatus: factors contributing to their efficacy in the treatment of venous insufficiency.
PubMed:Suppression of liver cytochrome P450 by alpha-hederin: relevance to hepatoprotection.
PubMed:[Protective effect of the fulvotomentosides on paracetamol-induced hepatotoxicity in mice].
PubMed:Zinc-induced arsenite tolerance in mice.
PubMed:In vitro antifungal activity of triterpenoid saponins.
PubMed:Effects of alpha-hederin, a saponin extracted from Hedera helix, on cells cultured in vitro.
PubMed:Altered maternal zinc metabolism following exposure to diverse developmental toxicants.
PubMed:Altered Zn status by alpha-hederin in the pregnant rat and its relationship to adverse developmental outcome.
PubMed:The effects of 10 triterpenoid compounds on experimental liver injury in mice.
PubMed:Induction of metallothionein by alpha-hederin.
PubMed:Saponins of the ivy plant, Hedera helix, and their leishmanicidic activity.
PubMed:[Studies on the saponin constituents of Kalopanax septemlobus (Thunb.) koidz].
PubMed:[Studies on the chemical constituents of Lonicera fulvotomentosa Hsu et S.C. Cheng].
PubMed:Rapid analysis of alpha-hederin in a crude plant extract by collisional mass spectrometry (CAD MIKES).
PubMed:Role of glycosidases in the membranlytic, antifungal action of Saponins.
PubMed:Letter: Antiviral activity of hederin.
PubMed:Isolation of a saponin, hederin, and its sapogenin, hederagenin, from bur clover (Medicago hispida).
 
Notes:
derived from beta-amyrin; other hederigenin based saponins are available.
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