465-99-6

Usage

Uses

Used in Cancer Therapy:
Hederagenin is used as an anticancer agent for its ability to increase ROS production, reduce colony formation, and induce apoptosis in cisplatin-resistant HNC cells. In vivo, it has been shown to suppress tumor growth in a cisplatin-resistant HNC mouse xenograft model.
Used in Cardiovascular Disease Management:
Hederagenin is used in the management of cardiovascular diseases as it has been demonstrated to reduce aortic atherosclerotic lesion area, serum cholesterol and LDL levels, and iNOS protein levels in a rat model of atherosclerosis.
Used in Alcohol-Induced Hepatotoxicity Treatment:
Hederagenin is used in the treatment of alcohol-induced hepatotoxicity as it has been shown to reduce ethanol-induced production of TNF-α, IL-6, and COX-2, ALDH2 mRNA expression, and liver damage in a rat model.
Used in Neurodegenerative Disease Management:
Hederagenin is used in the management of neurodegenerative diseases, specifically Parkinson's disease, as it induces autophagy and inhibits oligomerization of α-synuclein in a mouse model induced by MPTP.
Used in Leukemia Treatment:
Hederagenin is used as a triterpenoid to inhibit the proliferation of leukemia HL-60 cells.

InChI:InChI=1/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27+,28+,29+,30-/m0/s1

Upstream product

• 639-14-5 gypsogenin 
• 85889-27-6 3-O-β-D-glucuronopyranoside of hederagenin 
• 107241-23-6 3-O-[α-L-arabinopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-α-L-arabinopyranosyl]-28-O-[β-D-glucopyranoside] hederagenin 
• 38631-44-6 hederagenin 3-O-<β-D-xylopyranosyl-(1-2)-α-L-arabinopyranoside> 
• 20853-58-1 hederagenin 3-O-β-D-glucopyranosyl-(1->2)-O-α-L-arabinopyranoside 
• 68027-14-5 hederacolchiside F 
• 121449-76-1 kalopanax-saponin C (3-O-α-rhamnopyranosyl-(1->2)-<β-glucopyranosyl-(1->3)>-α-arabinopyranosyl hederagenin 28-O-α-rhamnopyranosyl-(1->4)-β-glucopyranosyl-(1->6)-β-glucopyranosyl ester 
• 83864-75-9 hederagenin 23-O-α-arabinopyranoside (CP₀) 
• 89837-88-7 C₄₁H₆₄O₁₄ 
• 89355-07-7 C₄₆H₇₂O₁₈ 
• 89789-08-2 salsoloside D 
• 27013-91-8 α-Hederin 
• 27013-91-8 alpha-Hederin 
• 64-17-5 ethanol 

Downstream Products

• 56820-58-7 7-chloro-[1]naphthol 
• 486-34-0 1,2,7-trimethylnaphthalene 
• 1679-02-3 2,9-dimethyl-picene 
• 5811-87-0 1,8-naphthalaldehydic acid 
• 466-01-3 23-hydroxy-3-oxo-olean-12-en-28-oic acid 
• 582-16-1 2,7-dimethylnaphthalene 
• 488-23-3 1,2,3,4-Tetramethylbenzene 
• 597-43-3 2,2-dimethylsuccinic acid 
• 1375560-61-4 tert-butyl diphenyl silyl 23-O-benzoylhederagenate 
• 219550-95-5 benzyl (3β,4α)-3,23-dihydroxy-olean-12-en-28-oate 

Relevant academic research and scientific papers

Symphytoxide A, a triterpenoid saponin from the roots of Symphytum officinale.

A new triterpenoidal saponin of hederagenin named symphytoxide A has been isolated from the ethanolic extract of the roots of Symphytum officinale and characterized on the basis of chemical investigations and spectroscopic studies as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)- alpha-L-arabinopyranosyl] hederagenin. The structure of this new saponin was established on the basis of 1D and 2D NMR experiments including heteroCOSY, COSY-45 degrees as well as HMBC measurements and other spectroscopic techniques. The saponin exhibited hypotensive activity in anesthetized rats.

Triterpenoid saponins of pulsatilla koreana root have inhibition effects of tumor necrosis factor-α secretion in lipopolysaccharide-induced RAW264.7 cells

In the present study, a new oleanane-type triterpenoid saponin, pulsatilloside F (1), along with 21 known compounds (2-22), were isolated from the root of Pulsatilla koreana. Their chemical structures were elucidated by mass, 1H-, 13C-NMR, correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) spectroscopy. Anti-inflammatory effects of the compounds were evaluated in terms of inhibitory of tumor necrosis factor a (TNF-α) secretion in the lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cell line. Compounds 19 and 20 exhibited particularly inhibitory effects with respective IC50 values of 0.32 and 0.65 μm. Compounds 1-4, 7 and 10-13 exhibited inhibitory effects with inhibition rates up to 41.55-73.76% at a concentration of 5 μm, respectively.

A BISDESMOSIDIC TRITERPENE SAPONIN FROM CEPHALARIA TRANSSYLVANICA

The structure of cephalaria saponin B, isolated from Cephalaria transsylvanica was eluciated as 3-O-4)-α-L-rhamnopyranosyl(1->2)-β-D-xylopyranosyl>->-3β,24-dihydroxy-12(13)-oleanene-28-oic acid. - Key words: Cephalaria transsylvanica; Dipsacaceae; flowers; cephalaria saponin B; hederagenin.

Triterpene glucosides from the leaves of aralia elata and their cytotoxic activities

Three new triterpene glucosides, named congmuyenosides C-E (1-3, resp.), along with four known ones, were isolated from an EtOH extract of Aralia elata (Miq.) Seem. leaves. The structures of the new compounds were identified as 3-O-{β-D-glucopyranosyl-(1→

TRITERPENE GLYCOSIDES OF Hedera colchica. STRUCTURE OF HEDERACOLCHISIDES E AND F

The leaves of Colchis ivy (family Araliaceae) have yielded polar glycosides - hederacolchisides E and F - and their structures have been established.It has been shown on the basis of the results of methylation and of acid and alkaline hydrolysis that these glycosides are hexaosides of oleanolic acid and of hederagenin.

Interconversion of hederagenin and gypsogenin and accessing 4-epi-hedragonic acid

Gypsogenin (1) and hederagenin (2) were isolated by extracting the powdered roots of Saponaria officinalis and the pericarp of Sapindus saponaria, respectively. While the gypsophila derived saponin can be obtained easily and in large quantities as a technical product, the plant material from Sapindus saponaria is difficult to obtain in Europe and the North-Americas, whereas in Latin America it is readily available (unlike the gypsophila saponin). In order to achieve a better accessibility of both aglycones, gypsogenin (1) and hederagenin (2), a simple synthesis for their interconversion was developed. Modification of the reaction conditions led to the first synthesis of 4-epi-hedragonic acid (3).

Eranthisaponins A and B, two new bisdesmosidic triterpene saponins from the tubers of Eranthis cilicica

The present investigation aimed at the glycoside constituents of the tubers of Eranthis cilicica has resulted in the isolation of two new bisdesmosidic triterpene saponins based upon hederagenin, named eranthisaponins A (1) and B (2), along with four known triterpene saponins. The structures of the new saponins 1 and 2 were determined on the basis of spectroscopic analysis, including extensive 1D and 2D NMR data, and acid hydrolysis followed by chromatographic analysis. This is the first report concerning the secondary metabolites of E. cilicica.

TRITERPENE GLYCOSIDES OF Climacoptera transoxana. I.

Two tripene glycosides - copterosides B and C -have been isolated from the epigeal part of Climacoptera transoxana (Iljin) Botsch.On the basis of chemical transformations and physicochemical characteristics, copteroside B has been identified as hedaragenin 3-O-β-D-glucopyranosiduric acid while copteroside C has the structure of hederagenin 3-O-.

Utility of coupled-HSQC experiments in the intact structural elucidation of three complex saponins from Blighia sapida

The structures of three complex saponins from the fruit pods of Blighia sapida have been elucidated and their 1H and 13C NMR spectra assigned employing a variety of one- and two-dimensional NMR techniques without degradative chemistry. The saponins have either four or six monosaccharide units linked to a triterpene aglycone. High-resolution, proton-coupled-HSQC spectra were important for determining both the identities of the intact monosaccharide units and coupling constants in strongly coupled proton spin systems. These NMR experiments will prove crucial as the complexity of saponin structures reaches the limit that can be determined solely by NMR.

Triterpene glycosides from the whole plant of Anemone hupehensis var. japonica and their cytotoxic activity

Three new triterpene glycosides (1-3), together with eight known triterpene glycosides (4-11), were isolated from the whole plant of Anemone hupehensis var. japonica (Ranunculaceae). The structures of the new compounds were determined on the basis of spec