465-00-9

Basic information

• Product Name: Arjunolic acid
• Synonyms: arjunolic acid;2,3,23-Trihydroxyolean-12-en-28-oic acid;(2alpha,3beta,4alpha)-2,3,23-Trihydroxy-olean-12-en-28-oic acid;Arjulic acid;Olean-12-en-28-oicacid, 2,3,23-trihydroxy-, (2a,3b,4a)-
• CAS NO: 465-00-9
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.7
• Product Categories: Pentacyclic Triterpenes
• Mol File: 465-00-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: 332-334 °C
• Boiling Point: 606°C at 760mmHg
• Flash Point: 334.3°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 3.26E-17mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: ?20°C
• PKA: 4.62±0.70(Predicted)
• CAS DataBase Reference: Arjunolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Arjunolic acid(465-00-9)
• EPA Substance Registry System: Arjunolic acid(465-00-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 465-00-9(Hazardous Substances Data)

Usage

Description

Arjunolic acid is a triterpene that has been found in T. arjuna and has diverse biological activities, including antioxidant, anticancer, and anti-inflammatory properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay when used at a concentration of 0.8 mM. Arjunolic acid (20 mg/kg for four days) prevents arsenic-induced decreases in the activity of superoxide dismutase (SOD1), catalase, GST, and glutathione reductase in mouse brain. It reduces tumor growth in an Ehrlich murine spontaneous adenocarcinoma model when administered at doses of 100 and 250 mg/kg for 20 days. Arjunolic acid reduces renal fibrosis and increases in kidney TNF-α and IL-1β levels induced by cisplatin in mice when administered at doses of 100 and 250 mg/kg per day for 10 days.

Uses

Arjunolic Acid is a naturally occurring terpenoid which displays anti-inflammatory activity as well as protective effects during chemical induced organ pathophysiology.

Definition

ChEBI: A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensi , it exhibits antioxidant and antimicrobial activities.

InChI:InChI=1/C30H48O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1

Upstream product

• 118041-50-2 lobatoside C 
• 120057-47-8 undeca-acetate of medicoside J 
• 1189348-34-2 3-β-[(O-β-D-glucopyranosyl-(1->4)-O-[α-L-rhamnopyranosyl-(1->2)]-α-L-arabinopyranosyl)oxy]-2β,23-dihydroxyolean-12-en-28-oic acid 
• 1191300-09-0 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-[α-L-arabinopyranosyl-(1->3)]-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-10-3 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-[β-D-apio-D-furanosyl-(1->3)]-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-11-4 β-D-xylopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->3)]-α-L-rhamnopyranosyl-(1->2)-[α-L-arabinopyranosyl-(1->3)]-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-12-5 β-D-xylopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->3)]-α-L-rhamnopyranosyl-(1->2)-[α-L-arabinopyranosyl-(1->3)]-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-13-6 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-{[β-D-apio-D-furanosyl-(1->3)]-4-O-(8-oxo-16-β-[(D-xylopyranosyl)oxy]hexadecanoyl)}-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-14-7 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-{[β-D-apio-D-furanosyl-(1->3)]-4-O-(9-oxo-16-β-[(D-xylopyranosyl)oxy]hexadecanoyl)}-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1412872-18-4 2β,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-xylopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranoside 
• 1412872-19-5 2β,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-xylopyranosyl-(1→6)-O-β-D-glucopyranoside 
• 123714-90-9 lobatoside B 
• 124961-78-0 C₅₉H₉₆O₂₈ 
• 124961-76-8 C₅₃H₈₆O₂₃ 

Downstream Products

• 22452-82-0 2α,3β,23-trihydroxyolean-12-en-28-oic acid methyl ester 
• 22425-81-6 Methyl 2β,3β-dihydroxy-23α-hydroxymethyl-Δ¹²-oleanene-28β-carboxylate 
• 60393-68-2 2α,3β,23-trihydroxyolean-12-en-28-oic acid triacetate 
• 1382469-50-2 C₃₂H₄₈O₆ 
• 1382469-49-9 C₃₀H₄₆O₅ 
• 26553-62-8 olean-12-ene-2β,3β,23,28-tetraol 
• 471-59-0 Barringtogenol 
• 89503-62-8 arjunolic bromo lactone triacetate 
• 106861-86-3 bayogenin triacetate 

Relevant articles and documents

New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.

Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.

A new biologically active triterpenoid saponin from the aerial parts of Neanotis wightiana

Phytochemical investigation of the aerial parts of Neanotis wightiana for the first time has led to the isolation of one new triterpenoid saponin, neanoside A (1), along with seven known compounds, oleanolic acid (2), ursolic acid (3), β-sitosterol (4) and its glucoside (5), stigmasterol (6) and its glucoside (7) and hexacosanoic acid (8). The structures of these compounds were elucidated by means of spectroscopic (NMR, MS and other) and chemical techniques as well as comparison with literature data. The structure of 1 was elucidated as 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl (1 → 3)-β-d-glucopyranosyl bayogenin. The in vitro biochemical analysis of compound 1 against the activity of human serum liposomal enzymes, SGOT (serum glutamate oxaloacetate transaminase), SGPT (serum glutamate pyruvate transaminase) and ALP (alkaline phosphatase) and glycerol kinase showed significant reduction of their activity.

Oleanane saponins from Bellis sylvestris Cyr. and evaluation of their phytotoxicity on Aegilops geniculata Roth

Six oleanane saponins were isolated for the first time from leaves of Bellis sylvestris Cyr., the southern daisy. Their structures were established by the extensive use of 2D-NMR experiments, including COSY, TOCSY, NOESY, HSQC, HMBC, CIGAR, H2BC, and HSQC-TOCSY, along with Q-TOF HRMS2 analysis. All of the compounds are constituted by bayogenin as aglycone, and characterized by the presence of an oligosaccharide moiety, consisting of two to four sugar unities esterified at the C-28 carboxyl carbon. One of the isolated compounds is a bisdesmoside containing an additional sugar moiety at the C-3 carbon. The phytotoxic activity assayed against Aegilops geniculata Roth., a coexisting test species, has been evaluated revealing that all the compounds, at the highest concentrations, showed strong phytotoxicity against the leaf development.