82462-67-7Relevant academic research and scientific papers
Dehydrohispanolone Derivatives Attenuate the Inflammatory Response through the Modulation of Inflammasome Activation
González-Cofrade, Laura,Oramas-Royo, Sandra,Cuadrado, Irene,Amesty, ángel,Hortelano, Sonsoles,Estevez-Braun, Ana,De Las Heras, Beatriz
, p. 2155 - 2164 (2020)
The NLRP3 inflammasome plays a critical role in inflammation-mediated human diseases and represents a promising drug target for novel anti-inflammatory therapies. Hispanolone is a labdane diterpenoid isolated from the aerial parts of Ballota species. This diterpenoid and some derivatives have demonstrated anti-inflammatory effects in classical inflammatory pathways. In the present study, a series of dehydrohispanolone derivatives (1-19) was synthesized, and their anti-inflammatory activities toward NLRP3 inflammasome activation were evaluated. The structures of the dehydrohispanolone analogues produced were elucidated by NMR spectroscopy and mass spectrometry. Four derivatives significantly inhibited IL-1β secretion, with 15 and 18 being the most active (IC50 = 18.7 and 13.8 μM, respectively). Analysis of IL-1β and caspase-1 expression revealed that the new diterpenoids 15 and 18 are selective inhibitors of the NLRP3 inflammasome, reinforcing the previously demonstrated anti-inflammatory properties of hispanolone derivatives.
Transformations of hispanolone. Novel Michael adducts with in planta activity against rice blast
Van Wyk, Albert W.W.,Gray, Christopher A.,Keyzers, Robert A.,Rivett, Douglas E.A.,Caira, Mino R.,Nader, Bassam S.,Davis, George E.,Werk, Todd L.,Davies-Coleman, Michael T.
, p. 8493 - 8498 (2007/10/03)
Two novel Michael adducts 9α-cyano-15,16-epoxy-7β-hydroxylabda- 13(16),14-dien-6-one (2) and 9α-cyano-15,16-epoxy-7-hydroxylabda-7,13(16), 14-trien-6-one (3) and the reduction product of 2, 9α-cyano-15,16-epoxy- 6β,7β-dihydroxylabda-13(16),14-diene (4), w
The absolute stereochemistry of a diterpene from Ballota aucheri
Gray, Christopher A.,Rivett, Douglas E.A.,Davies-Coleman, Michael T.
, p. 409 - 413 (2007/10/03)
The semi-synthetic transformation of hispanolone, isolated from Ballota africana, into βp-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one has established an ent-labdane absolute stereochemistry for a diterpene metabolite originally isolated from B. aucheri.
A new route to 2,7- and 7-functionalized labdanes
Hersel, Ulrich,Steck, Melanie,Seifert, Karlheinz
, p. 1609 - 1615 (2007/10/03)
A new route for the synthesis of 2,7- and 7-functionalized labdanes starts from (R)-carvone (1). 11-Nordrim-7-en-9-one (15) is an appropriate starting material for the total synthesis of hispanone (21), a biologically active furolabdane isolated from the
Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone
Cheung, Wing Shun,Wong, Henry N. C.
, p. 11001 - 11016 (2007/10/03)
On the basis of the recently reported construction of (±)-hispanolone (2), the enantiomerically pure form of (-),2, employed in our partial synthesis of the specific platelet activating factor receptor antagonist prehispanolone (3), was prepared from (S)-
Total syntheses of naturally occurring molecules possessing 1,7- dioxaspiro[4.4]nonane skeletons
Wong, Henry N. C.
, p. 1757 - 1765 (2007/10/03)
The syntheses of several naturally occurring molecules, namely prehispanolone, sphydrofuran, secosyrins, and syringolides are reviewed. Interestingly, these compounds are all structurally related, possessing a 1,7-dioxaspiro[4.4]nonane framework. The pivotal step in these synthetic endeavors involves the peracid oxidation of substituted 2- trimethylsilylfurans to but-2-en-4-olides. A subsequent intramolecular Michael addition procedure was also essential in the construction of the spiro skeleton. Two significant issues concerning regioselectivity and stereoselectivity are also addressed.
