84692-91-1

Basic information

• Product Name: arglabin
• Synonyms: arglabin;(3aR,4aS)-1,4aα-Dimethyl-7-methylene-4a,5,6,6aα,9aβ,9bα-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(7H)-one;(3aS)-2,3,3aβ,4,5β,6,6a,7,9aβ,9bα-Decahydro-6α,6aα-epoxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2-one;3H-Oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one, 5,6,6a,7,9a,9b-hexahydro-1,4a-diMethyl-7-Methylene-, [4aS-(3aS*,4aα,6aα,9aβ,9bα)]-;Arglabine;(3aR,4aS,6aS,9aS,9bR)-5,6,6a,7,9a,9b-Hexahydro-1,4a-dimethyl-7-methylene-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one;3H-Oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one,5,6,6a,7,9a,9b-hexahydro-1,4a-dimethyl-7-methylene-, (3aR,4aS,6aS,9aS,9bR)
• CAS NO: 84692-91-1
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.304
• Mol File: 84692-91-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 100-102 °C
• Boiling Point: 404.6°C at 760 mmHg
• Flash Point: 171.3°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 9.34E-07mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly)
• CAS DataBase Reference: arglabin(CAS DataBase Reference)
• NIST Chemistry Reference: arglabin(84692-91-1)
• EPA Substance Registry System: arglabin(84692-91-1)

Safety Data

• Hazardous Substances Data: 84692-91-1(Hazardous Substances Data)

Usage

Description

Arglabin is a sesquiterpene gamma-lactone, an organic heterotetracyclic compound and guaianolide sesquiterpene lactone, extracted from Artemisia glabella, a plant native to Kazakhstan. It is a potent and selective inhibitor of farnesyl transferase, an enzyme critical to the function of the Ras oncogene in cancer cell reproduction. Arglabin is characterized by its unique structure, with an epoxidised double bond in the 7-membered ring and a gamma-lactone formed through formal condensation of the hydroxy and carboxy groups.

Uses

Used in Anticancer Applications:
Arglabin is used as an antineoplastic agent for the treatment of a variety of cancers. It exhibits a strong inhibitory effect against tumor cells proliferation in in vitro models of transformed mouse hepatocytes and splenocytes. The cytotoxic effect against tumor cells is 50-100 times higher than that on intact cells. In many patients with various cancers, Arglabin has been shown to stop or inhibit tumor development, either alone or in combination with other anticancer agents. It is reportedly well-tolerated with few side effects and has demonstrated promising response rates in treating difficult-to-treat cancers such as breast, ovarian, lung, or colon cancers.
Used in Diabetic Nephropathy Treatment:
Arglabin is used in the inhibition of glucose-induced NF-kB activation and MCP-1/TGF-β1 expression for treating diabetic nephropathy. Its cytotoxic properties make it a potential therapeutic agent in managing this condition.
Used in Pharmaceutical Industry:
Arglabin is used as an ethical pharmaceutical, first developed in Kazakhstan and later in the US and other countries. It can be obtained through resin extraction from A. glabella, followed by purification by chromatography and finally recrystallization. Arglabin-DMA HCl, the hydrochloride salt of the adduct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Kazakhstan for the treatment of breast, colon, ovarian, and lung cancers.

Originator

NuOncology Labs (Kazakstan)

InChI:InChI=1/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11-,12-,14-,15+/m0/s1

Upstream product

• 68370-47-8 (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one 
• 81066-45-7 kauniolide 
• 503551-53-9 parthenolide 
• 1343403-10-0 (1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one 

Downstream Products

• 1370045-04-7 2-({[(3aR,4aS,6aS,7S,9aS,9bR)-1,4a-dimethyl-8-oxo-4a,5,6,6a,7,8,9a,9b-octahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-7-yl]methyl}thio)benzoic acid 
• 6831-14-7 arborescin 
• 36416-50-9 3α,4α-epoxyarglabin 
• 36416-50-9 3β,4β-epoxyarglabin 

Relevant articles and documents

Chamomile lactone derivative as well as preparation method and application thereof (by machine translation)

The invention relates to the technical field of organic synthesis, in particular to a small white chrysanthemum lactone derivative and a preparation method and application thereof. To the invention, small white chrysanthemum is used as the original main raw material, 11 small white chrysanthemum lactone derivatives are synthesized through a series of chemical reactions, and the derivatives have certain anti-proliferative activity on glioblastoma cells. The invention also proves that the deuterated derivative DMAPAPAPAPAPT-D6 can significantly induce accumulation of active oxygen of glioblastoma cells, thereby leading DNA damage in glioblastoma cells. Furthermore, DMAPAPAPAPAPT-D6 promotes exogenous apoptosis mediated by the death receptor of caspase, indicating DNA damage induced by DMAPAPAPAPAPT-D6 inducible glioblastoma apoptosis. , ROS accumulation caused by DMAPAPAPAPAPT-D6 treatment leads DNA damage and death receptor-mediated apoptosis, which indicates that DMAPAPAPAPAPT-D6 with novel ingredients has therapeutic potential for treating glioblastoma and can be applied to preparation of drugs for treating glioblastoma. (by machine translation)

USES OF SESQUITERPENE LACTONE COMPOUNDS AND THEIR DERIVATIVES IN DRUGS PREPARATION

The present invention relates to the uses of sesquiterpene lactone compounds and their derivatives in preparing drugs. It belongs to the field of drug technology, specifically relates to the uses of the compounds of Formula (I) in preparing the drugs, especially the uses in preparing the drugs to treat rheumatoid arthritis and treat cancers through inhibiting cancer stem cells.

Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-κB activation and MCP-1 and TGF-β1 expression in rat mesangial cells

Diabetic nephropathy (DN) is one of the most common and serious chronic complications of diabetes mellitus, however, no efficient clinical drugs exist for the treatment of DN. We selected and synthesized several sesquiterpene lactones (SLs), and then used the MTT assay to detect rat mesangial cells (MCs) proliferation, ELISA to measure the expression level of monocyte chemoattractant protein-1 (MCP-1), transforming growth factor beta (TGF-β1) and fibronectin(FN), real-time fluorescent quantitative PCR analysis to measure the MCP-1 and TGF-β1 gene expression, western blot to detect the level of IκBα protein and EMSA to measure the activation of nuclear factor kappa B (NF-κB). We discovered that SLs, including parthenolide (PTL), micheliolide (MCL), arglabin, and isoalantolactone (IAL), as well as several synthetic analogs of these molecules, could effectively attenuate the high glucose-stimulated activation of NF-κB, the degradation of IκBα, and the expression of MCP-1, TGF-β1 and FN in rat mesangial cells (MCs). These findings suggest that SLs and their derivatives have potential as candidate drugs for the treatment of DN.