Abstract
Nodulisporic acids D, E, and F are the newest members of a family of nontremorogenic indole-diterpenoids that are potent, orally bioavailable, antiflea agents derived from a fungus belonging to the genus Nodulisporium. The four members of the D series are each devoid of an isoprene residue that is present at C-26 in the three nodulisporic acids described originally (the A series). Nodulisporic acid E (11a) has a simpler structure, which lacks not only the isoprene residue at C-26 but also two that form the A/B rings. Nodulisporic acid F is the simplest of all nodulisporic acids and is devoid of all three isoprene residues of the indole unit; as such, it represents the earliest biosynthetic intermediate in this series. A biogenetic grid based on mutation studies is proposed that encompasses all the known nodulisporic acids. Structure-activity relationships of the known natural nodulisporic acids have been elucidated. Within a series the most active compound possesses a dienoic acid chain, and overall, the end product of the biogenetic grid, i.e., nodulisporic acid A, exhibits the most potent antiflea activity. Additionally, the stereochemistries of C-3' ' and C-4' ' of nodulisporic acid D(2) and therefore of nodulisporic acids A...Continue Reading
References
Jan 16, 1998·Medical and Veterinary Entomology·D A OstlindW Mickle
Oct 31, 2000·Bioorganic & Medicinal Chemistry Letters·P T MeinkeM H Fisher
Feb 13, 2001·Molecular Microbiology·C YoungB Scott
Nov 7, 2001·The Journal of Parasitology·W L ShoopD M Schmatz
Nov 9, 2001·Organic Letters·R BergerS L Colletti
Apr 13, 2002·Organic Letters·Prasun K ChakravartyPeter T Meinke
May 16, 2002·Biochemistry·Steven W LudmererMcHardy M Smith
Jun 8, 2002·Current Topics in Medicinal Chemistry·Peter T MeinkeWesley L Shoop
Jun 11, 2002·The Journal of Parasitology·T FelcettoW L Shoop
Jun 13, 2002·Journal of the American Chemical Society·Kevin M ByrneJohn G Ondeyka
Sep 25, 2002·Bioorganic & Medicinal Chemistry Letters·John G OndeykaSheo B Singh
Dec 7, 2002·Bioorganic & Medicinal Chemistry Letters·Prasun K ChakravartyPeter T Meinke
Jan 25, 2003·Journal of Natural Products·John G OndeykaSheo B Singh
Jul 29, 2003·Molecular Genetics and Genomics : MGG·L K McMillanB Scott
Nov 5, 2003·The Alkaloids. Chemistry and Biology·Heather Sings, Sheo Singh
Citations
Mar 26, 2013·Applied Microbiology and Biotechnology·Chengwei LiuTohru Dairi
Jun 15, 2011·ACS Combinatorial Science·Paul D ThorntonKeith R Buszek
Oct 5, 2007·Journal of the American Chemical Society·Yang S Tran, Ohyun Kwon
Apr 7, 2006·Organic Letters·Amos B SmithLaszló Kürti
Mar 15, 2013·Organic Letters·Ronald BesandreJeremy A May
Oct 12, 2012·PloS One·Gerald F BillsMarc Stadler
Jun 5, 2014·The Journal of Antibiotics·Chino MatsuiKazuo Umezawa
Sep 17, 2013·Applied and Environmental Microbiology·Chengwei LiuTohru Dairi
Aug 28, 2014·Critical Reviews in Microbiology·Monika Sharma, Rohit Sharma
Jul 2, 2014·Marine Drugs·Kunlai SunWeiming Zhu
Feb 12, 2008·Mycological Research·Sanjay SaikiaBarry Scott
May 21, 2013·Steroids·Qi-Chang ZhengHao Gao
Jul 19, 2014·Bioscience, Biotechnology, and Biochemistry·Chengwei LiuTohru Dairi
Sep 16, 2016·Organic Letters·Chengwei LiuHideaki Oikawa
Jul 30, 2016·Chemical Communications : Chem Comm·Guohua WangJing Peng
Jan 13, 2018·Genome Announcements·Matthew J NicholsonEmily J Parker
Sep 18, 2018·Natural Product Research·Jia-Hao LiangYi-Xuan Zhang
Oct 30, 2007·The Journal of Antibiotics·Masahiro OgataKazuo Shin-ya
Dec 22, 2009·Natural Product Reports·Shu-Ming Li
Aug 31, 2017·The Journal of Antibiotics·Yike Zou, Amos B Smith
Mar 7, 2020·Natural Product Reports·Ryo TanifujiHideaki Oikawa
Aug 9, 2019·MedChemComm·Kyle C Van de BittnerEmily J Parker
Nov 8, 2020·Phytochemistry·You QinShui-Han Zhang
Feb 13, 2021·Bioscience, Biotechnology, and Biochemistry·Masaru Enomoto
May 19, 2009·Journal of Medicinal Chemistry·Peter T MeinkeWesley L Shoop
Jun 2, 2015·Journal of the American Chemical Society·Yike ZouAmos B Smith
May 24, 2019·Journal of Natural Products·Ni P AriantariPeter Proksch
Sep 29, 2018·Journal of the American Chemical Society·Nicole A GodfreySergey V Pronin
Jul 22, 2018·Journal of the American Chemical Society·Yike ZouAmos B Smith
May 22, 2007·The Journal of Organic Chemistry·Amos B SmithHaruaki Ishiyama