Hederacoside CCAS# 14216-03-6 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 14216-03-6 | SDF | Download SDF |
| PubChem ID | 11491905 | Appearance | White powder |
| Formula | C59H96O26 | M.Wt | 1221.38 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Synonyms | Kalopanaxsaponin B | ||
| Solubility | DMSO : 100 mg/mL (81.87 mM; Need ultrasonic) | ||
| Chemical Name | [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate | ||
| SMILES | CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)(C)C)O)O)O)CO)O)O)O | ||
| Standard InChIKey | RYHDIBJJJRNDSX-MCGLQMIESA-N | ||
| Standard InChI | InChI=1S/C59H96O26/c1-24-34(63)38(67)42(71)49(78-24)83-46-29(20-60)80-48(45(74)41(46)70)77-22-30-37(66)40(69)44(73)51(81-30)85-53(75)59-17-15-54(3,4)19-27(59)26-9-10-32-55(5)13-12-33(56(6,23-61)31(55)11-14-58(32,8)57(26,7)16-18-59)82-52-47(36(65)28(62)21-76-52)84-50-43(72)39(68)35(64)25(2)79-50/h9,24-25,27-52,60-74H,10-23H2,1-8H3/t24-,25-,27-,28-,29+,30+,31+,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Hederacoside C is one of the active ingredients in Hedera helix leaf extract (Ivy Ex.) and AG NPP709, a new botanical drug to treat acute respiratory infection and chronic inflammatory bronchitis. Hederacoside C has antispasmodic activity. Hederacoside C is a potent competitive inhibitor for serine protease porcine pancreatic elastase, shows comparable IC 50 value is 40.6 uM; it also non-competitively inhibits hyaluronidase activity in a dose- dependent fashion, shows comparable IC 50 value is 280.4 uM. |
| In vitro | Pre-treatment with α-hederin increases β-adrenoceptor mediated relaxation of airway smooth muscle.[Pubmed: 20637581]Phytomedicine. 2011 Jan 15;18(2-3):214-8.Preparations of ivy leaves dry extract with secretolytic and bronchiolytic efficacy are widely used for the treatment of acute and chronic obstructive airway diseases. The mechanism by which ivy preparations improve lung functions is not fully understood. 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: 21291987]J Ethnopharmacol. 2011 Apr 12;134(3):796-802.The long tradition of using the dry extract of Hedera helix (common ivy) leaves in traditional and contemporary alternative medicine caused that many biological and pharmacological studies have been aimed at evaluating the effects of ivy. Some of the results suggest that Hedera helix extract possesses bronchodilatatory and antispasmodic activity. On the other hand, the symptoms of ivy intoxication in human and animals, as well as adverse-reactions observed during the therapy with ivy-based pharmaceuticals, indicate rather stimulant effect of the plant on smooth muscle. Thus, the aim of this study was to evaluate the effect of two main active substances extracted from the plant (α-hederin and Hederacoside C) and the whole dry extract of Hedera helix on the gut motility. In vitro antispasmodic compounds of the dry extract obtained from Hedera helix.[Pubmed: 9140224]Planta Med. 1997 Apr;63(2):125-9.Commercial dry extract of Hedera helix L. is used for the treatment of disorders of the respiratory tract; it is standardized towards papaverine (papaverine equivalent value, PE, activity of 1 g test substance equivalent to the activity of x mg papaverine) by in vitro antispasmodic activity on isolated guinea-pig ileum with acetylcholine as spasmogen. |
| In vivo | Pharmacokinetics of hederacoside C, an active ingredient in AG NPP709, in rats.[Pubmed: 23607546 ]Xenobiotica. 2013 Nov;43(11):985-92.1. Hederacoside C (HDC) is one of the active ingredients in Hedera helix leaf extract (Ivy Ex.) and AG NPP709, a new botanical drug to treat acute respiratory infection and chronic inflammatory bronchitis. However, information regarding its pharmacokinetic properties remains limited. |
| Kinase Assay | 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: 8554461]Arch Pharm (Weinheim). 1995 Oct;328(10):720-4.Triterpene and steroid saponins and sapogenins of medicinal plants (Aesculus hippocastanum L., Hedera helix L., Ruscus aculeatus L.) are claimed to be effective for the treatment/prevention of venous insufficiency. |
Hederacoside C Dilution Calculator
Hederacoside C Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.8187 mL | 4.0937 mL | 8.1875 mL | 16.3749 mL | 20.4687 mL |
| 5 mM | 0.1637 mL | 0.8187 mL | 1.6375 mL | 3.275 mL | 4.0937 mL |
| 10 mM | 0.0819 mL | 0.4094 mL | 0.8187 mL | 1.6375 mL | 2.0469 mL |
| 50 mM | 0.0164 mL | 0.0819 mL | 0.1637 mL | 0.3275 mL | 0.4094 mL |
| 100 mM | 0.0082 mL | 0.0409 mL | 0.0819 mL | 0.1637 mL | 0.2047 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Hederacoside C is a principal bioactive pharmaceutical ingredient of Hedera helix leaf that can treat respiratory disorders, because of its expectorant, bronchodilator, antibacterial, and bronchospasmolytic effects.
References:
[1]. Rehman SU et al. An ultra-high-performance liquid chromatography-tandem mass spectrometric method for the determination ofhederacoside C, a drug candidate for respiratory disorder, in rat plasma. J Pharm Biomed Anal. 2016 Jun 24;129:90-95.
[2]. Kim JM et al. Pharmacokinetics of hederacoside C, an active ingredient in AG NPP709, in rats. Xenobiotica. 2013 Nov;43(11):985-92.
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In vitro antispasmodic compounds of the dry extract obtained from Hedera helix.[Pubmed:9140224]
Planta Med. 1997 Apr;63(2):125-9.
Commercial dry extract of Hedera helix L. is used for the treatment of disorders of the respiratory tract; it is standardized towards papaverine (papaverine equivalent value, PE, activity of 1 g test substance equivalent to the activity of x mg papaverine) by in vitro antispasmodic activity on isolated guinea-pig ileum with acetylcholine as spasmogen. In order to determine the phytochemical basis for the antispasmodic activity, bioassay guided fractionation and subsequent isolation of phenolic compounds (flavonols, caffeoylquinic acids) and saponins (Hederacoside C, alpha-hederin, hederagenin) was carried out. Fractions and isolates obtained were investigated for antispasmodic activity and their contribution to the activity of the extract was calculated. Significant activity was found for both saponins and phenolic compounds, the PE values being approx. 55 and 49 for alpha-hederin and hederagenin, 54 and 143 for quercetin and kaempferol, and 22 for 3,5-dicaffeoylquinic acid, respectively. In view of their relative high concentration the saponins contribute most to the anti-spasmodic activity, followed by dicaffeoylquinic acids and the flavonol derivatives. The results indicate that the summed PE value of the compounds mentioned is an acceptable agreement with the PE value of the whole extract determined biologically.
Pharmacokinetics of hederacoside C, an active ingredient in AG NPP709, in rats.[Pubmed:23607546]
Xenobiotica. 2013 Nov;43(11):985-92.
1. Hederacoside C (HDC) is one of the active ingredients in Hedera helix leaf extract (Ivy Ex.) and AG NPP709, a new botanical drug to treat acute respiratory infection and chronic inflammatory bronchitis. However, information regarding its pharmacokinetic properties remains limited. 2. Here, we report the pharmacokinetics of HDC in rats after intravenous administration of HDC (3, 12.5, and 25 mg/kg) and after oral administration of HDC, Ivy Ex., and AG NPP709 (equivalent to 12.5, 25, and 50 mg/kg HDC). 3. Linear pharmacokinetics of HDC were identified upon its intravenous administration at doses of 3-25 mg/kg. Intravenous administration of HDC results in relatively slow clearance (1.46-2.08 mL/min/kg) and a small volume of distribution at steady state (138-222 mL/kg), while oral administration results in a low absolute oral bioavailability (F) of 0.118-0.250%. The extremely low F of HDC may be due to poor absorption of HDC from the gastrointestinal (GI) tract and/or its decomposition therein. 4. The oral pharmacokinetics of HDC did not differ significantly among pure HDC, Ivy Ex., and AG NPP709.
Pre-treatment with alpha-hederin increases beta-adrenoceptor mediated relaxation of airway smooth muscle.[Pubmed:20637581]
Phytomedicine. 2011 Jan 15;18(2-3):214-8.
Preparations of ivy leaves dry extract with secretolytic and bronchiolytic efficacy are widely used for the treatment of acute and chronic obstructive airway diseases. The mechanism by which ivy preparations improve lung functions is not fully understood. Here, we tested the influence of the three main saponins of ivy, alpha-hederin, Hederacoside C and hederagenin, on the contraction and relaxation behaviour of isolated bovine tracheal smooth muscle strips by isometric tension measurements. None of the tested compounds altered histamine or methacholine-induced contraction of the smooth muscle strips. In contrast, the isoprenaline-induced relaxation of 100muM methacholine precontracted muscle strips was significantly enhanced when pre-treated with 1muM of alpha-hederin for 18h. The pre-treatment with Hederacoside C or hederagenin had no effect on isoprenaline-induced relaxation. For the first time the bronchiolytic effect of alpha-hederin was demonstrated by isometric tension measurements using bovine tracheal smooth muscle strips. alpha-Hederin increases isoprenaline-induced relaxation indirectly, probably by inhibiting heterologous desensitization induced by high concentrations of muscarinic ligands like methacholine.
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:21291987]
J Ethnopharmacol. 2011 Apr 12;134(3):796-802.
ETHNOPHARMACOLOGICAL RELEVANCE: The long tradition of using the dry extract of Hedera helix (common ivy) leaves in traditional and contemporary alternative medicine caused that many biological and pharmacological studies have been aimed at evaluating the effects of ivy. Some of the results suggest that Hedera helix extract possesses bronchodilatatory and antispasmodic activity. On the other hand, the symptoms of ivy intoxication in human and animals, as well as adverse-reactions observed during the therapy with ivy-based pharmaceuticals, indicate rather stimulant effect of the plant on smooth muscle. Thus, the aim of this study was to evaluate the effect of two main active substances extracted from the plant (alpha-hederin and Hederacoside C) and the whole dry extract of Hedera helix on the gut motility. MATERIALS AND METHODS: The experiments were carried out on isolated stomach corpus and fundus strips. The tissues were isolated from rats. The experiments were performed in isotonic conditions. The results are expressed as the percent of the reaction caused by a reference contractile substance, acetylcholine. RESULTS AND CONCLUSIONS: The obtained results revealed that alpha-hederin applied in the concentration ranged from 25 to 320muM significantly changed the spontaneous motoric activity of rat stomach smooth muscle. The observed reaction had always the same character, a contraction, and its force was concentration dependent. The second tested saponin, Hederacoside C, did not alter the motility of rat isolated stomach corpus and fundus strips when administered in the concentration up to 100 muM, however, if applied in the concentration of 350 muM it induced a remarkable concentration of smooth muscle. Eventually, the whole extract of Hedera helix in a dose containing 60 muM of Hederacoside C produced a strong contraction which strength was comparable with the reaction generated by acetylcholine. According to the results, it is very likely that alpha-hederin, but not Hederacoside C contributes to the contractile response of isolated stomach corpus and fundus strips to the application of Hedera helix leaves' extract.
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:8554461]
Arch Pharm (Weinheim). 1995 Oct;328(10):720-4.
Triterpene and steroid saponins and sapogenins of medicinal plants (Aesculus hippocastanum L., Hedera helix L., Ruscus aculeatus L.) are claimed to be effective for the treatment/prevention of venous insufficiency. In this work we evaluated the inhibitory effects of these plant constituents on the activity of elastase and hyaluronidase, the enzyme systems involved in the turnover of the main components of the perivascular amorphous substance. The results evidence that for Hedera helix L., the sapogenins only non-competitively inhibit hyaluronidase activity in a dose-dependent fashion, showing comparable IC50 values (hederagenin IC50 = 280.4 microM; oleanolic acid IC50 = 300.2 microM); both the saponins Hederacoside C and alpha-hederin are very weak inhibitors. The same behaviour is observed for serine protease porcine pancreatic elastase: the glycosides are devoid of inhibitory action, while genins are potent competitive inhibitors (oleanolic acid IC50 = 5.1 microM; hederagenin IC50 = 40.6 microM). Constituents from Aesculus hippocastanum L. show inhibitory effects only on hyaluronidase, and this activity is mainly linked to the saponin escin (IC50 = 149.9 microM), less to its genin escinol (IC50 = 1.65 mM). By contrast, ruscogenins from Ruscus aculeatus L., ineffective on hyaluronidase activity, exhibit remarkable anti-elastase activity (IC50 = 119.9 microM; competitive inhibition). The mechanism of elastase inhibition by triterpene and steroid aglycones, with a nitroanilide derivative as substrate, is discussed.
