Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 33, 2019 - Issue 19
379
Views
6
CrossRef citations to date
0
Altmetric
Research Articles

An indole diterpenoid isolated from the fungus Drechmeria sp. and its antimicrobial activity

, , , , , , , , , , & show all
Pages 2770-2776 | Received 22 May 2018, Accepted 09 Jul 2018, Published online: 17 Sep 2018

References

  • Apfel CM, Evers S, Hubschwerlen C, Pirson W, Page MG, Keck W. 2001. Peptide deformylase as an antibacterial drug target: assays for detection of its inhibition in Escherichia coli cell homogenates and intact cells. Antimicrob Agents Chemother. 45:1053–1057.
  • Byrne KM, Smith SK, Ondeyka JG. 2002. Biosynthesis of nodulisporic acid A: precursor studies. J Am Chem Soc. 124:7055–7060.
  • Calvo AM, Cary JW. 2015. Association of fungal secondary metabolism and sclerotial biology. Front Microbiol. 6:62.
  • Dowd PF, Cole RJ, Vesonder RF. 1988. Toxicity of selected tremorgenic mycotoxins and related compounds to Spodoptera frugiperda and Heliothis zea. J Antibiot. 41:1868–1872.
  • Fan Y, Wang Y, Liu P, Fu P, Zhu T, Wang W, Zhu W. 2013. Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492. J Nat Prod. 76:1328–1336.
  • Gao SS, Li XM, Williams K, Proksch P, Ji NY, Wang BG. 2016. Rhizovarins A-F, indole-diterpenes from the mangrove-derived endophytic fungus Mucor irregularis QEN-189. J Nat Prod. 79:2066–2074.
  • Huang XH, Nishida H, Tomoda H, Tabata N, Shiomi K, Yang DJ, Takayanagi H, Omura S. 1995. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. II. Structure elucidation of terpendoles A, B, C and D. J Antibiot. 48:5–11.
  • Ji H, Wang FP. 2006. Structure of lasiansine from Aconitum nagarum var. lasiandrum. J Asian Nat Prod Res. 8:619–624.
  • Kyriakidis N, Waight ES, Day JB, Mantle PG. 1981. Novel metabolites from Penicillium crustosum, including penitrem E, a tremorgenic mycotoxin. Appl Environ Microbiol. 42:61–62.
  • Lee HY, Jang EJ, Bae SY, Jeon JE, Park HJ, Shin J, Lee SK. 2016. Anti-melanogenic activity of gagunin D, a highly oxygenated diterpenoid from the marine sponge Phorbas sp., via modulating tyrosinase expression and degradation. Mar Drugs. 14:212.
  • Li SM. 2010. Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis. Nat Prod Rep. 27:57–78. Jan
  • Lu Z, Li H, Bian M, Li A. 2015. Total synthesis of epoxyeujindole A. J Am Chem Soc. 137:13764–13767.
  • Munday-Finch SC, Wilkins AL, Miles CO. 1996. Isolation of paspaline B, an indole-diterpenoid from Penicillium paxill. Phytochemistry. 41:327–332.
  • Saikia S, Nicholson MJ, Young C, Parker EJ, Scott B. 2008. The genetic basis for indole-diterpene chemical diversity in filamentous fungi. Mycol Res. 112:184–199.
  • Sharpe RJ, Johnson JS. 2015. Asymmetric total synthesis of the indole diterpene alkaloid paspaline. J Org Chem. 80:9740–9766.
  • Shoop WL, Gregory LM, Zakson-Aiken M, Michael BF, Haines HW, Ondeyka JG, Meinke PT, Schmatz DM. 2001. Systemic efficacy of nodulisporic acid against fleas on dogs. J Parasitol. 87:419–423.
  • Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Ha SN, Dahl-Roshak A, Greene J, Kim JA, Smith HM, Shoop W, Tkacz JS. 2004. Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships. J Nat Prod. 67:1496–1506.
  • Smith AB, 3rd, Davulcu AH, Cho YS, Ohmoto K, Kurti L, Ishiyama H. 2007. Indole diterpene synthetic studies. Total synthesis of (+)-nodulisporic acid F and construction of the heptacyclic cores of (+)-nodulisporic acids A and B and (-)-nodulisporic acid D. J Org Chem. 72:4596–4610.
  • Springer JP, Clardy J. 1980. Paspaline and paspalicine, two indole-mevalqnate metabolite from Claviceps paspali. Tetrahedron Lett. 21:231–234.
  • Sun CP, Nie XF, Kang N, Zhao F, Chen LX, Qiu F. 2017. A new phenol glycoside from Physalis angulata. Nat Prod Res. 31:1059–1065.
  • Sun CP, Qiu CY, Zhao F, Kang N, Chen LX, Qiu F. 2017. Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their anti-proliferative and anti-inflammatory activities. Sci Rep. 7:4057.
  • Sun C-P, Qiu C-Y, Yuan T, Nie X-F, Sun H-X, Zhang Q, Li H-X, Ding L-Q, Zhao F, Chen L-X, Qiu F. 2016. Antiproliferative and anti-inflammatory withanolides from Physalis angulata. J Nat Prod. 79:1586–1597.
  • Wang C, Huo X-K, Luan Z-L, Cao F, Tian X-G, Zhao X-Y, Sun C-P, Feng L, Ning J, Zhang B-J, Ma X-C. 2017. Alismanin A, a triterpenoid with a C34 skeleton from Alisma orientale as a natural agonist of human pregnane X receptor. Org Lett. 19:5645–5648.
  • Yu X, Li SM. 2012. Prenyltransferases of the dimethylallyltryptophan synthase superfamily. Meth Enzymol. 516:259–278.
  • Yu Z-L, Peng Y-L, Wang C, Cao F, Huo X-K, Tian X-G, Feng L, Ning J, Zhang B-J, Sun C-P, Ma X-C. 2017. Alismanoid A, an unprecedented 1,2-seco bisabolene from Alisma orientale and the protective activity on H2O2-induced damage in SH-SY5Y cells. New J Chem. 41:12664–12670.
  • Zhang Z-J, Huo X-K, Tian X-G, Feng L, Ning J, Zhao X-Y, Sun C-P, Wang C, Deng S, Zhang B-J, et al. 2017. Novel protostane-type triterpenoids with inhibitory human carboxylesterase 2 activities. Rsc Adv. 7:28702–28710.
  • Zhao JC, Wang YL, Zhang TY, Chen ZJ, Yang TM, Wu YY, Sun CP, Ma XC, Zhang YX. 2018. Indole diterpenoids from the endophytic fungus Drechmeria sp. as natural antimicrobial agents. Phytochemistry. 148:21–28.
  • Zhao JC, Luan ZL, Liang JH, Cheng ZB, Sun CP, Wang YL, Zhang MY, Zhang TY, Wang Y, Yang TM. 2018. Drechmerin H, a novel 1(2), 2(18)-diseco indole diterpenoid from the fungus Drechmeria sp. as a natural agonist of human pregnane X receptor. Bioorg Chem. 79:250–256.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.