New Sesquiterpene Lactones from<i>Montanoa tomentosa</i>subsp.<i>xanthiifolia</i>*

Lidia-Pérez, Ana; Caballero, María Beda Aída; Ortega, Alfredo; Gaviño, Rubén; Vivar, Alfonso Romo de

doi:10.1055/s-2006-959472

Cited by 3 publications

(2 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Germacrolides have been mostly isolated from species within the genus Montanoa, 17 whereas in some species additionally heliangolides and guaianolides (e.g., in M. tomentosa 18 ) or eudesmanolides (e.g., in M. dumicola 2 ) have been found. The unusual montahibisciolides have been reported only from M. hibiscifolia and M. leucantha ssp.…”

Section: Resultsmentioning

confidence: 99%

Sesquiterpene Lactones from Montanoa hibiscifolia That Inhibit the Transcription Factor NF-κB

et al. 2004

View full text Add to dashboard Cite

The reinvestigation of the aerial parts of Montanoa hibiscifolia afforded four new eudesmanolides (1-4), three of them with a rare endoperoxide structural element and the fourth with a rare carbonyl function. It also afforded three unusual montabibisciolides (5-7), two (5 and 7) of which are new natural compounds. Additionally, seven germacrolides (8-10 and 12-15) and one melampolide (11) could be isolated, including two new germacrolides (8 and 9). Their structures were elucidated using 1D and 2D NMR measurement as well as ESI, CIMS, and HRMS analyses. Low-energy conformations were obtained by molecular mechanics calculations. The (13)C NMR data of five compounds are reported for the first time. Six sesquiterpene lactones (4, 6, 10, 11, 12, and 14) were investigated for their inhibitory activity on DNA binding of the transcription factor NF-kappa B using Jurkat T cells as well as RAW 264.7 cells. Besides the alpha-methylene-gamma-butyrolactone moiety the epoxy group in the acyl residue might take part in the NF-kappa B inhibitory activity of sesquiterpene lactones.

show abstract

Section: Resultsmentioning

confidence: 99%

Sesquiterpene Lactones from Montanoa hibiscifolia That Inhibit the Transcription Factor NF-κB

et al. 2004

View full text Add to dashboard Cite

show abstract

“…Diketone 39 is a new compound. Only one precedent of a natural compound possessing the [4+8] bicyclic skeleton present in 39 has been reported 45. Remarkably, the interannular junction of the natural compound was reported to be cis , contrary to that reported for 39 .…”

Section: Resultsmentioning

confidence: 90%

Structural Diversity from the Transannular Cyclizations of Natural Germacrone and Epoxy Derivatives: A Theoretical–Experimental Study

Morales

Catalán

Domingo

et al. 2013

Chemistry A European J

View full text Add to dashboard Cite

Treatment of germacrone (1) with different electrophiles, and of its epoxy derivatives germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3) and isogermacrone-4,5-epoxide (4) with Brönsted/Lewis acids and Ti(III), gives rise to a great structural diversity. Thus, by using a maximum of two steps, the production of more than 40 compounds corresponding to 14 skeletons is described. Computational calculations rationalizing the structural divergence produced are also described. Finally, since some of the compounds generated are bioactive natural sesquiterpenes, the mechanisms of formation of these substances will provide new insights in their biosynthesis.

show abstract

Chemical synthesis of terpenoids with participation of cyclizations plus rearrangements of carbocations: a current overview

2019

View full text Add to dashboard Cite

New Sesquiterpene Lactones fromMontanoa tomentosasubsp.xanthiifolia*

Cited by 3 publications

References 6 publications

Sesquiterpene Lactones from Montanoa hibiscifolia That Inhibit the Transcription Factor NF-κB

Sesquiterpene Lactones from Montanoa hibiscifolia That Inhibit the Transcription Factor NF-κB

Structural Diversity from the Transannular Cyclizations of Natural Germacrone and Epoxy Derivatives: A Theoretical–Experimental Study

Chemical synthesis of terpenoids with participation of cyclizations plus rearrangements of carbocations: a current overview

Contact Info

Product

Resources

About