4290-13-5

Basic information

• Product Name: santamarine
• Synonyms: Balchanin;(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g]benzofuran-2-one;(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one;santamarine;SANTAMARIN;(3aS)-2,3,3aβ,4,5,5a,6,7,9aβ,9bα-Decahydro-6α-hydroxy-5aα,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one
• CAS NO: 4290-13-5
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Product Categories: Sesquiterpenoids
• Mol File: 4290-13-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 142 °C
• Boiling Point: 415.6°Cat760mmHg
• Flash Point: 176.5°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.54±0.60(Predicted)
• CAS DataBase Reference: santamarine(CAS DataBase Reference)
• NIST Chemistry Reference: santamarine(4290-13-5)
• EPA Substance Registry System: santamarine(4290-13-5)

Safety Data

• Hazardous Substances Data: 4290-13-5(Hazardous Substances Data)

Usage

Description

Santamarine is a sesquiterpene lactone belonging to the eudesmanolide group, which is a type of organic compound derived from plants. It possesses significant anticancer properties, making it a promising candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
Santamarine is used as an anticancer agent for its ability to inhibit the proliferation of cancer cells and induce apoptosis, leading to the programmed cell death of these cells. This makes it a valuable compound in the development of new cancer treatments and therapies.
Used in Cancer Research:
In addition to its direct application as an anticancer agent, santamarine is also used in cancer research to better understand the mechanisms behind its antiproliferative and apoptotic effects. This knowledge can contribute to the development of more effective and targeted cancer treatments in the future.

InChI:InChI=1/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1

Upstream product

• 69075-77-0 gallicin 
• 553-21-9 costunolide 
• 29484-23-9 costunolide-1,10-epoxide 

Downstream Products

• 3668-04-0 epoxysantamarin 
• 7715-89-1 11,13-dihydrosantamarin 
• 481-06-1 santonin 

Relevant articles and documents

Acyl Derivatives of Eudesmanolides To Boost their Bioactivity: An Explanation of Behavior in the Cell Membrane Using a Molecular Dynamics Approach

Semisynthetic analogs of natural products provide an important approach to obtain safer and more active drugs and they can also have enhanced physicochemical properties such as persistence, cross-membrane processes and bioactivity. Acyl derivatives of different natural product families, from sesquiterpene lactones to benzoxazinoids, have been synthesized and tested in our laboratories. These compounds were evaluated against tumoral and nontumoral cell lines to identify selective derivatives with a reduced negative impact upon application. The mode of action of these compounds was analyzed by anti-caspase-3 assays and molecular dynamics simulations with cell membrane re-creation were also carried out. Aryl derivatives of eudesmanolide stand out from the other compounds and are better than current anticancer drugs such as etoposide in terms of selectivity and activity. Computational studies provide evidence that lipophilicity plays a key role and the 4-fluorobenzoyl derivative can pass easily through the cell membrane.

Inhibition of TNF- α -Induced Inflammation by Sesquiterpene Lactones from Saussurea lappa and Semi-Synthetic Analogues

We investigated the tumor necrosis factor-alpha (TNF- α) inhibitory activity of sesquiterpenes from Saussurea lappa root extracts. According to the hexane and EtOAc extracts showing significant activity with IC 50 values of 0.5 and 1.0 μg/mL, respectively, chromatographic fractionation of the extracts was performed and led to the isolation of 10 sesquiterpenes (1 - 10). Costunolide (1), a major compound, and dehydrocostus lactone (4) exhibited high efficiency in decreasing TNF- α levels, with IC 50 values of 2.05 and 2.06 μM, respectively. In addition, sesquiterpene analogues were synthesized to establish their structure-activity relationship (SAR) profile. Among the semi-synthetic analogues, compounds 6a and 16 showed the most potent activity with IC 50 values of 1.84 and 1.97 μM, respectively. More importantly, compound 6a showed less toxicity than costunolide and 16. These results provided the first SAR profile of sesquiterpene lactones and indicated that the α -methylene- γ -lactone moiety plays a crucial role in TNF- α inhibition. Additionally, the epoxide derivative 6a might represent a lead compound for further anti-TNF- α therapies, owing to its potent activity and reduced toxicity.

Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae

Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)- salonitenolide (3), (-)-dehydrocostuslactone (4), (-)-lychnopholide (5), and (-)-eremantholide C (6) were performed. Incubation of 1 with C. echinulata afforded Δ(11(13))-dihydrogenation and Δ(1(10))-epoxidation products (7- 10). C. echinulata also hydrolyzed the side chain of 2, and transformed 4 into (+)-11α,13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Δ(11(13))-dihydrogenation and Δ(10(14))- epoxidation products (16 and 17). Both fungi transformed 5 into (-)-16-(1- methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions.