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Frenolicins H and I from the caterpillar-associated Streptomyces sp. TBRC17107.
Supong K, Bunbamrung N, Tanasupawat S, Auncharoen P, Nithithanasilp S, Rachtawee P, Pittayakhajonwut P. Supong K, et al. Nat Prod Res. 2023 Oct 4:1-10. doi: 10.1080/14786419.2023.2263902. Online ahead of print. Nat Prod Res. 2023. PMID: 37791589
Frenolicins A (3) and B (4) showed antimalarial activity against Plasmodium falciparum (IC(50) 17.4 and 1.37 muM), antibacterial activity against Bacillus cereus and Staphylococcus aureus (MIC 50.0 and 0.20 mug/mL). Only frenolicin B had anti-plant pathogenic fungal …
Frenolicins A (3) and B (4) showed antimalarial activity against Plasmodium falciparum (IC(50) 17.4 and 1.37 muM), antibacterial activity ag …
A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.
Zhang Y, Wang X, Sunkara M, Ye Q, Ponomereva LV, She QB, Morris AJ, Thorson JS. Zhang Y, et al. Org Lett. 2013 Nov 1;15(21):5566-9. doi: 10.1021/ol4027649. Epub 2013 Oct 23. Org Lett. 2013. PMID: 24151973 Free PMC article.
The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. ...
The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)- …
Frenolicins C-G, pyranonaphthoquinones from Streptomyces sp. RM-4-15.
Wang X, Shaaban KA, Elshahawi SI, Ponomareva LV, Sunkara M, Zhang Y, Copley GC, Hower JC, Morris AJ, Kharel MK, Thorson JS. Wang X, et al. J Nat Prod. 2013 Aug 23;76(8):1441-7. doi: 10.1021/np400231r. Epub 2013 Aug 14. J Nat Prod. 2013. PMID: 23944931 Free PMC article.
Four new pyranonaphthoquinones, frenolicins C-F (1-4), along with three known analogues, frenolicin (6), frenolicin B (7), and UCF76-A (8), were isolated from the fermentation of this strain. ...
Four new pyranonaphthoquinones, frenolicins C-F (1-4), along with three known analogues, frenolicin (6), frenolicin B (7), and …
Discovery of Frenolicin B as Potential Agrochemical Fungicide for Controlling Fusarium Head Blight on Wheat.
Han C, Yu Z, Zhang Y, Wang Z, Zhao J, Huang SX, Ma Z, Wen Z, Liu C, Xiang W. Han C, et al. J Agric Food Chem. 2021 Feb 24;69(7):2108-2117. doi: 10.1021/acs.jafc.0c04277. Epub 2021 Feb 15. J Agric Food Chem. 2021. PMID: 33586974
Three known pyranonaphthoquinones were isolated by means of an activity-guided method, and frenolicin B was characterized as the main active ingredient. Frenolicin B displayed strong antifungal activity against F. graminearum strain PH-1 with an EC(50) …
Three known pyranonaphthoquinones were isolated by means of an activity-guided method, and frenolicin B was characterized as t …
Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds.
Nájera C, Foubelo F, Sansano JM, Yus M. Nájera C, et al. Org Biomol Chem. 2020 Feb 19;18(7):1279-1336. doi: 10.1039/c9ob02597a. Org Biomol Chem. 2020. PMID: 32025682 Review.
Natural products containing five-membered lactones like quercus lactones, muricatacins, goniofufuranones, methylenolactocins and frenolicin B have been synthesized using stereodivergent routes. Macrolides are very abundant lactones and have been mainly prepared from …
Natural products containing five-membered lactones like quercus lactones, muricatacins, goniofufuranones, methylenolactocins and frenolic
Frenolicin B Targets Peroxiredoxin 1 and Glutaredoxin 3 to Trigger ROS/4E-BP1-Mediated Antitumor Effects.
Ye Q, Zhang Y, Cao Y, Wang X, Guo Y, Chen J, Horn J, Ponomareva LV, Chaiswing L, Shaaban KA, Wei Q, Anderson BD, St Clair DK, Zhu H, Leggas M, Thorson JS, She QB. Ye Q, et al. Cell Chem Biol. 2019 Mar 21;26(3):366-377.e12. doi: 10.1016/j.chembiol.2018.11.013. Epub 2019 Jan 17. Cell Chem Biol. 2019. PMID: 30661989 Free PMC article.
Here, we identify the prototypical pyranonaphthoquinone natural product frenolicin B (FB) as a selective inhibitor of Prx1 and Grx3 through covalent modification of active-site cysteines. ...
Here, we identify the prototypical pyranonaphthoquinone natural product frenolicin B (FB) as a selective inhibitor of Prx1 and …
Engineered biosynthesis of the antiparasitic agent frenolicin B and rationally designed analogs in a heterologous host.
Fitzgerald JT, Ridley CP, Khosla C. Fitzgerald JT, et al. J Antibiot (Tokyo). 2011 Dec;64(12):759-62. doi: 10.1038/ja.2011.86. Epub 2011 Sep 21. J Antibiot (Tokyo). 2011. PMID: 21934692 Free PMC article.
The polyketide antibiotic frenolicin B harbors a biosynthetically intriguing benzoisochromanequinone core, and has been shown to exhibit promising antiparasitic activity against Eimeria tenella. To facilitate further exploration of its chemistry and biology, we cons …
The polyketide antibiotic frenolicin B harbors a biosynthetically intriguing benzoisochromanequinone core, and has been shown …
Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans-stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin.
Eid CN, Shim J, Bikker J, Lin M. Eid CN, et al. J Org Chem. 2009 Jan 2;74(1):423-6. doi: 10.1021/jo801945n. J Org Chem. 2009. PMID: 19053617
This outcome is in contrast to the unnatural (3a,5)-cis-substituted dihydronaphthopyrans reported under similar conditions for the syntheses of (+)-frenolicin B and (+)-kalafungin. Computational modeling is presented that provides insight into this unusual stereosel …
This outcome is in contrast to the unnatural (3a,5)-cis-substituted dihydronaphthopyrans reported under similar conditions for the syntheses …
A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin.
Fernandes RA, Chavan VP, Mulay SV, Manchoju A. Fernandes RA, et al. J Org Chem. 2012 Nov 16;77(22):10455-60. doi: 10.1021/jo3019939. Epub 2012 Oct 31. J Org Chem. 2012. PMID: 23088749
A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, D-gluco …
A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deo …
22 results