alpha-hederin hydrate

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

CAS: 27013-91-8 C41 H66 O12 MW: 750.96742000

Identification

Namealpha-hederin hydrate
CAS Number27013-91-8
EINECS248-166-5
FDA UNII4H15F0GLV2
Molecular FormulaC41 H66 O12
Molecular Weight750.96742000
MDL NumberMFCD00010665
Nikkaji NumberJ17.197B
Beilstein0076156

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-mouse LD50 1800 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for alpha-hederin hydrate usage levels up tonot for fragrance use.
Recommendation for alpha-hederin hydrate flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

ivy PMC

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 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).