27013-91-8

Basic information

• Product Name: ALPHA-HEDERIN
• Synonyms: ALPHA-HEDERIN;HELIXIN;HEDERIN, ALPHA-;(3-beta,4-alpha)-nopyranosyl)oxy)-23-hydroxy;akebiasaponinpd;akebosidestc;alpha-hederine;glycosidel-e1
• CAS NO: 27013-91-8
• Molecular Formula: C₄₁H₆₆O₁₂
• Molecular Weight: 764.98
• EINECS: 248-166-5
• Product Categories: Tri-Terpenoids;Saponins;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 27013-91-8.mol

Chemical Properties

• Melting Point: 215°C (dec.)
• Boiling Point: 849.6oC at 760 mmHg
• Flash Point: 250.7oC
• Appearance: /
• Density: 1.32
• Vapor Pressure: 1.4E-33mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• PKA: 4.63±0.70(Predicted)
• CAS DataBase Reference: ALPHA-HEDERIN(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-HEDERIN(27013-91-8)
• EPA Substance Registry System: ALPHA-HEDERIN(27013-91-8)

Safety Data

• Statements: 22
• Safety Statements: 22-45-24/25
• RIDADR: 1544
• WGK Germany: 3
• RTECS: RK0177800
• Hazardous Substances Data: 27013-91-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Alpha-Hederin is used as an inhibitor of β2-adrenergic receptor-GFP fusion proteins for its potential application in the development of drugs targeting adrenergic receptors.
Used in Toxicological Research:
Due to its potential to cause asphyxiation, alpha-Hederin is used in toxicological research to study the effects of saponins on respiratory systems and to develop countermeasures against their toxic effects.

InChI:InChI=1/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)/t21-,23?,24-,25?,26?,27-,28-,29-,30+,31+,32+,33?,34?,37-,38-,39+,40+,41-/m0/s1

Upstream product

• 84607-60-3 hederagenin 3-O-α-L-arabinofuranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside 
• 87733-77-5 mukurozi-saponin X 
• 29321-28-6 hederagenin?3?O?[β?D?xylopyranosyl?(1→3)]?[α?L?rhamnopyranosyl?(1→2)]?α?L?arabinopyranoside 
• 29781-27-9 hederagenin 3-O-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 76729-67-4 hederagenin 3-O-β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 29321-28-6 hederogenin 3-O-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 33289-85-9 Dipsacosid B 
• 29781-27-9 C₅₂H₈₄O₂₁ 
• 60213-75-4 C₅₃H₇₈O₁₈ 
• 76729-67-4 hederagenin 3-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-β-D-ribopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside 
• 128717-92-0 3-O-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl ester 
• 942997-00-4 3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin-28-O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl ester 
• 120481-41-6 3-O-<α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl>-28-O-<6-acetyl-β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl>hederagenin 
• 87781-65-5 mukurozi-saponin Y₂ 

Downstream Products

• 73-34-7 L-rhamnose 
• 87-72-9 L-(+)-arabinose 
• 465-99-6 hedaragenin 
• 465-99-6 3β,23-Dihydroxy-olean-12-en-28-oic acid 
• 17184-21-3 prosapogenin 
• 465-99-6 hederagenin 
• 128902-64-7 3-O-alpha-L-arabinopyranoside hederagenin 

Relevant articles and documents

Antifungal activity of modified hederagenin glycosides from the leaves of Kalopanax pictum var. chinense

Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryptococcus neoformans, and Candida albican

Antimicrobially active hederagenin glycosides from Cephalaria elmaliensis

A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their structures were identified by extensive spectroscopic techniques (1D and 2D NMR, HR ESIMS) and chemical evidence. The antimicrobial activity of the extracts and the pure compounds was evaluated by the MIC method. According to the results, all pure compounds including the new ones were found to be very active against both gram-positive and gram-negative bacteria. Georg Thieme Verlag KG Stuttgart · New York.

Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.

Triterpene glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea

Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2) -O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum. 2005 Springer Science + Business Media, Inc.

Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins

The synthesis of α-hederin (3-O-[α-L-rhamnopyranosyl-(1→2) -α-L-arabinopyranosyl]hederagenin, 1), δ-hederin (3-O-(α-L-arabinopyranosyl)hederagenin, 3), and three related triterpenoid saponins is described as part of a study of the structure-activity relationships between triterpenoid saponins and hemolytic activity. 4-Methoxybenzyl α-L-arabinopyranoside (11) was synthesized first and then used to prepare the different arabinose acceptors. Glycosylation between the acceptors and 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (20) was performed in excellent yield to give the desired disaccharides. Coupling of the trichloroacetimidate derivatives of the disaccharides to allyl- or methyl-hederagenin gave the protected saponosides in high yields. The saponins and their corresponding methyl esters were then obtained in good to moderate yields after deprotection. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Metabolism of kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites.

When kalopanaxsaponin K (KPK) from Kalopanax pictus was incubated for 24 h at 37 degrees C with human intestinal microflora, KPK was mainly metabolized to kalopanaxsaponin I (KPI) via kalopanaxsaponin H (KPH) rather than via kalopanaxsaponin J (KPJ), and then transformed to kalopanaxsaponin A (KPA) and hederagenin. Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. transformed KPK to KPI and KPA and hederagenin via KPH or KPJ. However, Lactobacillus sp. and Streptococcus sp. transformed KPK to KPI, KPA, and hederagenin only via KPJ. The metabolite KPA of KPK showed potent antirheumatoid arthritis activity.

Metabolism of kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites

To investigate the relationship between the intestinal bacterial metabolism of kalopanaxsaponin B and H from Kalopanax pictus (Araliaceae), and their antidiabetic effect, kalopanaxsaponin B and H were metabolized by human intestinal microflora and the antidiabetic activity of their metabolites was measured. Human intestinal microflora metabolized kalopanaxsaponin B to kalopanaxsaponin A, hederagenin 3-O-α-L- arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin B were kalopanaxsaponin A and hederagenin. Kalopanaxsaponin H was metabolized to kalopanaxsaponin A and I, hederagenin 3-O-α-L-arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin H were kalopanaxsaponin I and hederagenin. Among kalopanaxsaponin B, H and their metabolites, kalopanaxsaponin A showed the most potent antidiabetic activity, followed by hederagenin. However, the main components, kalopanaxsaponin B and H, in K. pictus were inactive.