2221-82-1

Usage

InChI:InChI=1/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15+/m0/s1

Upstream product

• 553-21-9 costunolide 
• 108-24-7 acetic anhydride 
• 553-21-9 costunolide 
• 553-21-9 costunolide 

Downstream Products

• 2221-81-0 α-cyclocostunolide 
• 81373-87-7 6α-hydroxycostic acid methyl ester 
• 90933-58-7 2-((1S,2S,4aR,8R,8aS)-1-Hydroxy-8-methoxy-4a,8-dimethyl-decahydro-naphthalen-2-yl)-acrylic acid methyl ester 

Relevant academic research and scientific papers

(+)-β-FRULLANOLIDE AND (+)-BROTHENOLIDE, TWO NEW SESQUITERPENE LACTONES FROM THE LIVERWORT FRULLANIA BROTHERI STEPH.

Two new sesquiterpene lactones, named (+)-β-frullanolide and (+)-brothenolide, were isolated from liverwort Frullania brotheri Steph.The absolute structures of these lactones have been established.

Sesquiterpenoid Constituents of the Liverwort Frullania brotheri STEPH.

Two new sesquiterpene lactones, (+)-β-frullanolide and (+)-brothenolide, have been isolated from the liverwort Frullania brotheri STEPH. One of them, (+)-brothenolide, has an allergenic property. The absolute structures of these lactones have been established by spectroscopic analysis and chemical transformation.

Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome

Parthenolide (PTL) can target NLRP3 inflammasome to treat inflammation and its related disease, but its cytotoxicity limits further development as an anti-inflammatory drug. A series of PTL analogs and their Michael-type adducts were designed and synthesi

Synthesis of Active Strigolactone Analogues Based on Eudesmane- And Guaiane-Type Sesquiterpene Lactones

Strigolactones are natural products that are exuded by plants and stimulate parasitic weed germination. Their use in herbicides is limited since they are produced in small quantities, but the synthesis of bioactive analogues provides an alternative source. In this work, eleven analogues have been synthesized. Among them, nine compounds belong to a novel family named eudesmanestrigolactones. The procedure is short (3-6 steps), the starting materials are isolated on a multigram scale, and global yields are up to 8%, which significantly enhance isolated yields. In bioassay, the compounds germinated high percentages of Phelipanche ramosa, Orobanche cumana, and Orobanche crenata seeds, even at nanogram doses (100 nM). Bioactivity was stereochemistry-dependent, and it was discussed in terms of the presence and geometry of the enol ether, orientation of the butenolide, and unsaturation of ring A. The reported compounds provide a set of readily obtained allelochemicals with potential applications as preventive herbicides.

Easy Access to Alkoxy, Amino, Carbamoyl, Hydroxy, and Thiol Derivatives of Sesquiterpene Lactones and Evaluation of Their Bioactivity on Parasitic Weeds

It has been hypothesized that the α-methylene-?-lactone moiety of sesquiterpene lactones is a key unit for their bioactivity. As a consequence, modifications of these compounds have been focused on this fragment. In the work reported here, two sesquiterpene lactones, namely, dehydrocostuslactone and β-cyclocostunolide, a eudesmanolide obtained by controlled cyclization of costunolide, were chosen for modification by Michael addition at C-13. On applying this reaction to both compounds, it was possible to introduce the functional groups alkoxy, amino, carbamoyl, hydroxy, and thiol to give products in good to high yields, depending on the base and solvent employed. In particular, the introduction of a thiol group at C-13 in both compounds was achieved with outstanding yields (>90%) and this is unprecedented for these sesquiterpene lactones. The bioactivities of the products were evaluated on etiolated wheat coleoptile elongation and germination of seeds of parasitic weeds, with significant activity observed on Orobanche cumana and Phelipanche ramosa. The structure-activity relationships are discussed.

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.

Genepolide, a sesterpene γ-lactone with a novel carbon skeleton from mountain wormwood (Artemisia umbelliformis)

The sesterpene γ-lactone genepolide (5) has been isolated from a Swiss horticultural variety of mountain wormwood (Artemisia umbelliformis) developed as a thujones-free alternative to native Western Alps wormwoods for the production of liqueurs. Genepolid

Palladium II promoted rearrangement of germacranolides. Synthesis of (+)-stoebenolide and (+)-dehydromelitensin

Catalytic amounts of bis(benzonitrile)palladium (II) chloride enhanced reaction rates of germacranolides Cope rearrangement to elemanolides. On the other hand, equimolecular amounts of the palladium complex transformed germacranolides into eudesmanolides. These phenomena provide a versatile procedure for the synthesis of eudesmanolides and elemanolides under relatively mild experimental conditions. Thus, (+)-stoebenolide and (+)-dehydromelitensin were alternatively synthesized starting out from (+)-salonitenolide.

Olefin Acylation Reactions on Sesquiterpene Lactones

The olefin acylation of a variety of sesquiterpene lactones with acetic anhydride in the presence of zinc chloride as a catalyst in methylene chloride affords β,γ-unsaturated ketones of any α,β-isomers.The 1,5-cyclodecadiene system present in constunolide (XII) undergoes cyclization followed by acylation and in 11-spirocyclopropyl system cleavage of the cyclopropane occurs.

Chemistry of costunolide and biological activity of the derived lactones

Costunolide and its derived C-16 germacranolides on oxidation with selenium dioxide-t-butyl hydroperoxide afforded two melampolides, an aldehydolactone and the corresponding hydroxylactone, in each case. Structures were assigned to these melampolides on the basis of spectral data and chemical correlation. The aldehydolactones were significantly more active root promotors than their parent lactones. Costunolide and related germacranolides underwent cyclization on treatment with iodine and pyridinium chlorochromate to afford interesting products. (-)-β-Frullanolide has been synthesized and shown to be biologically more active when compared with its parent trans-lactone.