638-96-0

Usage

InChI:InChI=1/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-23,25H,10-18H2,1-8H3/t19-,20+,22+,23?,25+,27-,28+,29-,30-/m1/s1

Upstream product

• 638-95-9 α‐amyrin 
• 638-95-9 urs-12-en-3-ol 
• 22255-10-3 (3β)-urs-12-en-3-yl palmitate 
• 638-95-9 α-amyrin 

Downstream Products

• 638-95-9 α-amyrin 
• 5937-48-4 3α-hydroxyurs-12-ene 
• 464-97-1 urs-12-ene 
• 1146582-69-5 (E)-1-(2,4-dinitrophenyl)-2-(4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,6a,7,8,8a,9,10,11,12,12a,14,14a-hexadecahydropicen-3-(4H,6bH,14bH)-ylidene)-hydrazine 
• 40768-63-6 3-Benzylthio-ursa-2,12-dien 

Relevant academic research and scientific papers

New derivatives of 11-keto-β-boswellic acid (KBA) induce apoptosis in breast and prostate cancers cells

A series of new 11-keto-β-boswellic acid were partially-synthesized by modifying the hydroxyl and carboxylic acid functional groups of ring A. The structures of the new analogs were confirmed by detailed spectral data analysis. Compounds 4, 5 and 9 exhibi

UPLC-ESI-QTOF-MS2 characterisation of Cola nitida resin fractions with inhibitory effects on NO and TNF-α released by LPS-activated J774 macrophage and on Trypanosoma cruzi and Leishmania amazonensis

Introduction: The resin of Cola nitida is used in western Cameroon as incense for spiritual protection and during ritual ceremonies. This plant secretion has never been investigated although previous chemical and biological studies on other resins have drawn many attentions. Objective: The resin fractions which revealed inhibitory effect on nitric oxide (NO) and tumour necrosis factor alpha (TNF-α) released by lipopolysaccharide (LPS)-activated J774 macrophage as well as on intracellular forms of Leishmania amazonensis and Trypanosoma cruzi amastigote were chemically characterised. Moreover, their antiparasitic activities were compared to those of semi-synthetic triterpenes. Methodology: The anti-inflammatory activity was evaluated by measuring the nitrite production and the TNF-α concentration in the supernatants of LPS-activated macrophages by antigen capture enzyme-linked immunosorbent assay. Moreover, the antiparasitic assay was performed by infecting the host cells (THP-1) in a ratio parasite/cell 10:1 (L. amazonensis) and 2:1 (T. cruzi) and then exposed to the samples. The resin was separated in vacuo by liquid chromatography because of its sticky behaviour and the chemical profiles of the obtained fractions (F1–F4) were established by dereplication based on UPLC-ESI-MS2 data while semi-synthetic triterpenes were prepared from α-amyrin by oxidation reactions. Results: Fractions F1–F4 inhibited NO and TNF-α almost similarly. However, only F1, F3 and F4 showed promising antiparasitic activities while F2 was moderately active against both parasites. Hence, F1–F4 were exclusively composed of pentacyclic triterpenes bearing oleanane and ursane skeletons. Semi-synthetic compounds revealed no to moderate antiparasitic activity compared to the fractions. Conclusion: Although it will be difficult to prove the interaction resin-spirit, interesting bioactivities were found in the resin fractions.

Chemical constituents of Psychotria nemorosa gardner and antinociceptive activity

Through dereplication strategies using gas chromatography-mass spectrometry (GC-MS) and ultra fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS), the ethanol extract from Psycotria nemorosa leaves (Rubiaceae) showed to be composed of: cinnamic acid, dihydroactinidiolide, 4-hydroxy-β-ionone, phytol, isophytol, 4,8,12,16-tetramethylheptadecan- 4-olide, lupeol, a mixture of α/β-amyrin, the keto and acetylated derivatives, besides stigmast- 4-en-3-one, campesterol, stigmasterol and γ-sitosterol by GC-MS. Likewise, by UFLC-MS/MS, the main compounds identified were: butin, resveratrol, rutin, kaempferol 7-O-β-D-glucopyranoside, deacetylasperuloside, epiloganin, hordenine, strictosidine, N-methyl-1,2,3,4-tetrahydro-β-carboline and N-formyl-tryptamine. The antinociceptive activity of the crude extract ant its fractions was reported.

Synthesis of α-amyrin derivatives and their in vivo antihyperglycemic activity

Ficus racemosa belongs to the family of Moraceae and is commonly known as 'Gular' in north India. Bio-activity guided isolation work on the fruits of F. racemosa resulted in the identification of antidiabetic active principle, α-amyrin acetate 7. Compound 7 lowered the blood glucose levels by 18.4 and 17.0% at 5 and 24 h, respectively, in sucrose challenged streptozotocin induced diabetic rat (STZ-S) model at the dose of 100 mg/kg body weight. Fifteen novel derivatives viz, 9-21, 24, 25 of α-amyrin 8 were prepared and their antihyperglycemic activity profile was assessed. The p-chlorobenzoic acid derivative 9 and nicotinic acid derivative 14 showed potent antihyperglycemic activity at 100 mg/kg body weight.

Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line

In a study to investigate the relationship between the chemical structure and the differentiation-inducing activity of pentacyclic triterpenes, several lupane, oleanane, and ursane triterpenes were prepared and their effects on B16 2F2 melanoma cell differentiation and growth were examined. Eleven lupane triterpenes used in this study acted on the melanoma cells as a melanogen, but no induction of melanogenesis of B16 2F2 cells by oleanane and ursane was detected. The differences at C-17 of the lupane series and acetylation of the OH group at C-3 did not markedly influence their activities. However, the ED50 value for up-regulation of melanin biosynthesis was markedly decreased by the oxidation of the OH group at C-3 of lupeol (1). Betulinic acid (11), its methyl ester (12), lup-28-al-20(29)-ene-3β-ol (9), and lup-28-al-20(29)-en-3-one (10) inhibited B16 2F2 cell proliferation by induction of apoptosis. These findings suggested that the carbonyl group at C-17 might be essential for the apoptotic effects of these compounds on B16 2F2 cells.

Constituents of Pyrolytic Products obtained from Gum Resin of Boswellia carteri Birdw. (Incense "Aden")

The pyrolytic products obtained from Incense "Aden" (gum resin of Boswellia carteri Birdw.) were separated by Girard-P reagent.Prefractionation of the carbonylic portion was achieved by column chromatography on silica gel by gradient-elution.Subsequent GLC/MS-analysis of the resulting fractions allowed the identification of following substances: α-campholenaldehyde, cuminaldehyde, carvotacetone, phellandral, o-methylacetophenone, carvone, perilla-aldehyde, eucarvone, 1-acetyl-4-isopropenylcyclopentene, piperitone, nopinone, cryptone, verbenone, γ-campholenaldehyde, thujone, myrtenoic acid, p-menth-4-en-3-one, 3,6,6-trimethylnorpinan-2-one, myrtenal, 2,4-dimethylacetophenone, pinocamphone or isopinocamphone, isopropylidencyclohexane, α-amyrenone (2) and 11-keto-α-amyrenone (4) - Keywords: Carbonylic compounds of pyrolytic products; GLC/MS-Identification; Gum resin of Boswellia carteri Birdw.; Incense

TERPENOIDS OF CANARIUM ZEYLANICUM

The following terpenoids were identified in the oleoresin, bark and timber of Canarium zeylanicum: 3β-hydroxyurs-12-en-11-one, 3β-hydroxyolean-12-en-11-one, olean-12-en-3,11-dione, urs-12-en-3,11-dione, α- and β-amyrin, α- and β-amyrenone, taraxerol, sitosterol, canaric acid, elemene, elemol, α-pinene, α- and β-phellandrene, limonene, terpineol, and cavrone. - Key Word Index - Canarium zeylanicum; Burseraceae; oleoresin; bark; timber; monoterpenoids; sesquiterpenoids; triterpenoids; 3β-hydroxyurs-12-en-11-one (neoilexonol); 3β-hydroxyolean-12-en-11-one; olean-12-en-3,11-dione; urs-12-en-3,11-dione; elemene; elemol; α-amyrine and β-amyrine; α- and β-amyrenone; canaric acid; taraxerol; sitosterol.

INSECT GROWTH INHIBITOR FROM THE BARK OF SANTALUM ALBUM

Key Word Index -- Santalum album; Santalaceae; bark; insect growth inhibitor; triterpene; urs-12-en-3β-yl palmitate