79950-85-9Relevant articles and documents
Synthesis of sorbicillinoid analogues with anti-inflammation activities
Ding, Wenjuan,Li, Xiaosan,Tang, Jinshan,Tian, Danmei,Wang, Fangfang,Xu, Zhipeng,Zhang, Meng,Zhang, Youwei
, (2022/01/06)
Recently, we demonstrated potential anti-inflammatory effects of sorbicillinoids isolated from marine fungi. Here, we report the synthesis of a series of new sorbicillinoid analogues and assessed their anti-inflammatory activities. Our results reveal that side chain substitution with (E)-2-butenoyl, (E)-3-(4-fluorophenyl)-2-propenoyl, and (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl significantly enhanced the inhibitory effects of the derivatives on nitric oxide (NO) production and inducible NO synthesis (iNOS) expression stimulated by lipopolysaccharides (LPS) in mouse macrophage. Further chemical derivatization shows that the monomethylresorcinol skeleton worked better than the dimethylresorcinol skeleton in inhibiting LPS-induced inflammatory response in cultured cells. Among the 29 synthesized sorbicillinoid analogues, compounds 4b and 12b exhibited the strongest anti-inflammatory activities, holding the promise of being developed into lead compounds that can be explored as potent anti-inflammation agents.
Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization
Sib, Anna,Gulder, Tobias A. M.
supporting information, p. 12888 - 12891 (2017/09/14)
Natural products are a virtually inexhaustible source of small molecules with spectacular molecular architectures and biomedical potential. Their structural complexity generates formidable challenges to total synthesis but often also precludes time- and resource-efficient, stereoselective synthetic access. Biosynthetically, nature frequently uses dimerization and oligomerization reactions to produce highly challenging frameworks from simple starting materials. Impressive examples are the bisorbicillinoids, a family of fungal natural products thought to originate from the polyketide precursor sorbicillin. Utilizing the recombinant oxidoreductase SorbC from the sorbicillin biosynthetic gene cluster, a robust, fully stereoselective synthesis of bisorbicillinoid natural products and unnatural side-chain analogues was developed.
Biomimetic explorations towards the bisorbicillinoids: Total synthesis of bisorbicillinol, bisorbibutenolide, and trichodimerol
Nicolaou,Simonsen, Klaus B.,Vassilikogiannakis, Georgios,Baran, Phil S.,Vidali, Veroniki P.,Pitsinos, Emmanuel N.,Couladouros, Elias A.
, p. 3555 - 3559 (2007/10/03)
Strikingly simple cascade dimerization sequences can be used to assemble the complex frameworks of bisorbicillinoids such as bisorbicillinol (1), bisorbibutenolide (2), and trichodimerol (3). The mechanistic facets of the biomimetic total syntheses of these bioactive natural products were also explored. Inspection of the unique molecular architecture of these compounds reveals that they are likely to be assembled in nature by a dimerization of two oxidized forms of sorbicillin.