0000000000364853
AUTHOR
Markus Rohr
Anti-inflammatory dihydroxanthones from a Diaporthe species
Abstract In a search for anti-inflammatory compounds from fungi inhibiting the promoter activity of the small chemokine CXCL10 (Interferon-inducible protein 10, IP-10) as a pro-inflammatory marker gene, the new dihydroxanthone methyl (1R, 2R)-1,2,8-trihydroxy-6-(hydroxymethyl)-9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate (2) and the previously described dihydroxanthone AGI-B4 (1) were isolated from fermentations of a Diaporthe species. The structures of the compounds were elucidated by a combination of one- and two-dimensional NMR spectroscopy, mass spectrometry, and calculations using density functional theory (DFT). Compounds 1 and 2 inhibited the LPS/IFNγ induced CXCL10 promoter activity …
ChemInform Abstract: Synthetic Approaches to Antiinflammatory Macrolactones of the Oxacyclododecindione Type.
A variety of attempts to synthesize oxacyclododecindione macrolactones through carbonylative ring-closure, intramolecular alkyne hydroacyalation, and Ru-catalyzed double bond isomerization fails.
Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type
An esterification/Friedel-Crafts-cyclization approach permitted the first successful synthetic entry into the oxacyclododecindione subclass of the dihydroxyphenylacetic acid lactone-type natural products. This route allowed the preparation of two highly active anti-inflammatory fungal secondary metabolites 14-deoxyoxacyclododecindione and 14-deoxy-4-dechlorooxacyclododecindione as well as their 14-desmethyl analogues.
A surprising switch in absolute configuration of anti-inflammatory macrolactones.
Oxacyclododecindione-type macrolactones exhibit highly potent anti-inflammatory activities even at nanomolar concentration. After the determination of the relative configuration of the stereocenters at C14 and C15 by total synthesis of 4-dechloro-14-deoxyoxacyclododecindione and 14-deoxyoxacyclododecindione, the absolute configuration has now been assigned by X-ray crystallography. Surprisingly, the absolute configuration is (14S,15R) which differs for C15 from that of the well-known derivatives of (S)-curvularin. The biological activities of both enantiomers of 14-deoxyoxacyclododecindione, obtained by racemic synthesis and optical resolution, were investigated and the ring conformation of…
Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclododecindione Type
Various synthetic approaches to the oxacyclododecindione-type macrolactones, known for their potent anti-inflammatory activity, are presented. These include an attempted carbonylative ring closure, a hydroacylation route, and an approach by ring-closing metathesis and double bond isomerization, as well as a strategy including ring-closing metathesis/unsaturation. The last route allowed the preparation of a bioactive analogue of the recently described 14-deoxyoxacyclododecindione.
Correction: Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type
Correction for ‘Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type’ by Johannes Tauber et al., Org. Biomol. Chem., 2015, 13, 7813–7821.
Anti-inflammatory tetraquinane diterpenoids from a Crinipellis species.
The small pro-inflammatory 10kDa chemokine CXCL10 (Interferon-inducible protein 10, IP-10) plays an important role in mediating immune responses through the activation and recruitment of leukocytes such as T cells, eosinophils, monocytes and NK cells to the sites of inflammation. Elevated levels of CXCL10 have been associated with chronic inflammatory and infectious diseases and therefore CXCL10 represents an attractive target for the development of new anti-inflammatory drugs. In a search for anti-inflammatory compounds from fungi inhibiting the inducible CXCL10 promoter activity, four new tetraquinane diterpenoids, crinipellin E (1), crinipellin F (2), crinipellin G (3) and crinipellin H …
CCDC 1454207: Experimental Crystal Structure Determination
Related Article: Johannes Tauber, Markus Rohr, Thorsten Walter, Dieter Schollmeyer, Karin Rahn-Hotze, Gerhard Erkel, Till Opatz|2016|Org.Biomol.Chem.|14|3695|doi:10.1039/C6OB00430J