Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 32, 2018 - Issue 23
218
Views
9
CrossRef citations to date
0
Altmetric
Research Articles

Biotransformation of (-)-cubebin by Aspergillus spp. into (-)-hinokinin and (-)-parabenzlactone, and their evaluation against oral pathogenic bacteria

ORCID Icon, , , , , , , , & show all
Pages 2803-2816 | Received 12 Jun 2017, Accepted 02 Sep 2017, Published online: 06 Oct 2017

References

  • Albuquerque S, Bastos JK, Calefi PS, Ciuffi kJ, Cunha WR, Laurentiz RS, Lucarini R, Nassar EJ, Da Silva Filho AA, Silva MLA, et al. 2009. Cubebina, lignana dibenzilbutirolactólica, seus derivados semi-sintéticos e sintéticos, bem como outras lignanas e neolignanas como agente vasodilatador na terapia da disfunção erétil. Brazil: WHO. 2011075801 A1. JP 2012-545026 correspondent to PCT/BR2009/000433.
  • Ali S, Nawaz W. 2017. Optimisation of nutritional requirements for dopamine synthesis by calcium alginate-entrapped mutant strain of Aspergillus oryzae EMS-6. Nat Prod Res. 31(3):281–288.10.1080/14786419.2016.1233408
  • ANVISA. 2003. National health surveillance agency. RE- 899.
  • Asano Y, Kamikawa T, Tokoroyama T. 1976. A simple method for the synthesis of lignan skeleton. Syntheses of (±)-Parabenzlactone and (±)-Hinokinin. Bull Chem Soc Jap. 49(11):3232–3235.10.1246/bcsj.49.3232
  • Bardají DKR, da Silva JJM, Bianchi TC, Eugenio DS, Oliveira PF, Leandro LF, Rogez HLG, Veneziani RCS, Ambrosio SR, Tavares DC, et al. 2016. Copaifera reticulata oleoresin: chemical characterization and antibacterial properties against oral pathogens. Anaerobe. 40(1):18–27.10.1016/j.anaerobe.2016.04.017
  • Bastos JK, Albuquerque S, Silva MLA. 1999. Evaluation of the trypanocidal activity of lignans isolated from the leaves of Zanthoxylum naranjillo. Planta Med. 65(6):541–544.10.1055/s-1999-14012
  • Bastos JK, Carvalho JCT, de Souza GHB, Pedrazzi AHP, Sarti SJ. 2001. Anti-inflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo Griseb. J Ethnopharmacol. 75(2-3):279–282.10.1016/S0378-8741(01)00171-4
  • Bodiwala HS, Singh G, Singh R, Dey CS, Sharma SS, Bhutani KK, Singh IP. 2007. Antileishmanial amides and lignans from Piper cubeba and Piper retro-fractum. J Nat Med. 61(4):418–421.10.1007/s11418-007-0159-2
  • Cabanillas BJ, Le Lamer AC, Castillo D, Arevalo J, Rojas R, Odonne G, Bourdy G, Moukarzel B, Sauvain M, Fabre N. 2010. Caffeic acid esters and lignans from Piper sanguineispicum. J Nat Prod. 73(11):1884–1890.10.1021/np1005357
  • Choudhary MI, Gondal HY, Abbaskhan A, Rahman A. 2005. Microbial transformations of gelomulide g: a member of the rare class of diterpene lactones. Chem Biodivers. 2(10):1401–1408.10.1002/(ISSN)1612-1880
  • Clinical and Laboratory Standards Institute. 2007. Methods for antimicrobial susceptibility testing of anaerobic bacteria, approved standard M11eA7. 7th ed. Wayne, PA: CLSI.
  • Clinical and Laboratory Standards Institute. 2009. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, approved standard M7eA8. 8th ed. Wayne, PA: CLSI.
  • De Souza VA, da Silva R, Pereira AC, Royo VA, Saraiva J, Montanheiro M, de Souza GHB, da Silva Filho AAS, Grando MD, Donate PM, et al. 2005. Trypanocidal activity of (-)-cubebin derivatives against free amastigote forms of Trypanosoma cruzi. Bioorg Med Chem. 15(2):303–307.10.1016/j.bmcl.2004.10.079
  • França VC, Vieira KVM, Lima EO, Barbosa-Filho JMB, da-Cunha EVL, Silva MS. 2005. Phytochemical study of the aerial parts of Aristolochia birostris Ducht. (Aristolochiaceae). Braz J Pharcog. 15(4):326–330.10.1590/S0102-695X2005000400012
  • Hirano T, Wakasugi A, Oohara M, Oka K, Sashida Y. 1991. Suppression of mitogen-induced proliferation of human peripheral blood lymphocytes by plant lignans. Planta Med. 57(04):331–334.10.1055/s-2006-960110
  • ICH. 2005. Harmonised tripartite guideline Validation of analytical procedures: text and methodology Q2(R1). Geneva: International Conference on Harmonization (ICH).
  • Jackson M, Karwoswski JP, Humphrey PE, Kohl WL, Barlow GJ, Tanaka S. 1993. Calbistrins, novel antifungal agents produced by Penicillium restrictum. I. Production, taxonomy of the producing organism and biological activity. J Antibiot. 46(1):34–38.10.7164/antibiotics.46.34
  • Lamb DC, Waterman MR, Zhao B. 2013. Streptomyces cytochromes P450: applications in drug metabolism. Expert Opin Drug Metab Toxicol. 9(10):1279–1294.10.1517/17425255.2013.806485
  • Lisowska K, Bizukojc M, Długoński J. 2006. An unstructured model for studies on phenanthrene bioconversion by filamentous fungus Cunninghamella elegans. Enzyme Microb Technol. 39(7):1464–1470.10.1016/j.enzmictec.2006.03.039
  • Messiano GB, Vieira L, Machado MB, Lopes LM, de Bortoli SA, Zukerman-Schpector J. 2008. Evaluation of insecticidal activity of diterpenes and lignans from Aristolochia malmeana against Anticarsia gemmatalis. J Agric Food Chem. 56(8):2655–2659.10.1021/jf703594z
  • Meyer HP, Turner NJ. 2009. Biotechnological manufacturing options for organic chemistry. Mini-Rev Org Chem. 6(4):300–306.10.2174/157019309789371550
  • Miyake Y, Fukumoto S, Okada M, Sakaida K, Nakamura Y, Osawa T. 2005. Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. J Agric Food Chem. 53(1):22–27.10.1021/jf048743 h
  • Miyazawa M. 2001. Biotransformation of lignans and neolignans. Curr Org Chem. 5(9):975–986.10.2174/1385272013375021
  • Moreira MR, Souza AB, Moreira MA, Bianchi TC, Carneiro LJ, Estrela FT, dos Santos RA, Januário AH, Martins CHG, Ambrosio SR, Veneziani RCS. 2013. RP-HPLC analysis of manool-rich Salvia officinalis extract and its antimicrobial activity against bacteria associated with dental caries. Braz J Pharmcog. 23(6):870–876.10.1590/S0102-695X2013000600003
  • Pascoli IC, Nascimento IR, Lopes LMX. 2006. Configurational analysis of cubebins and bicubebin from Aristolochia lagesiana and Aristolochia pubescens. Phytochem. 67(7):735–742.10.1016/j.phytochem.2006.01.019
  • Porto TS, Simão MR, Carlos LZ, Martins CHG, Furtado NAJC, Said S, Arakawa NS, Santos RA, Veneziani RCS, Ambrósio SR. 2013. Pimarane-type diterpenes obtained by biotransformation: antimicrobial properties against clinically isolated gram-positive multidrug-resistant bacteria. Phytother Res. 27(1):1502–1507.
  • Qi-He C, Jing L, Hai-Feng Z, Guo-Qing H, Ming-Liang F. 2009. The betulinic acid production from betulin through biotransformation by fungi. Enzyme Microb Technol. 45(1):175–180.
  • Raffaelli B, Wahala K. 2005. Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7 -hydroxylignano-9,9 -lactones. Org Biomol Chem. 4(1):331–341.
  • Rezende AAA, Munari CC, Oliveira PF, Ferreira NH, Tavares DC, Silva MLA, Rezende KCS, Spano MAA. 2013. Comparative study of the modulatory effects of (-)-cubebin on the mutagenicity/recombinogenicity induced by different chemical agents. Food Chem Toxicol. 55(1):645–652.10.1016/j.fct.2013.01.050
  • Ríos JL, Recio MC. 2005. Medicinal plants and antimicrobial activity. J Ethnopharmacol. 100(1–2):80–84.10.1016/j.jep.2005.04.025
  • Sallam LA, El-Abyad MS, El-Refai AH, El-Menofi HA, Adham NZ. 1995. Bioconversion of 19-nortestosterone by Rhodococcus sp. DSM 92-344. I: optimization of transformation parameters. Process Biochem. 30(1):25–34.10.1016/0032-9592(95)87004-0
  • Severiano ME, Simão MR, Ramos HP, Parreira RLT, Arakawa NS, Said S, Furtado NAJC, de Oliveira DCR, Gregório LE, Tirapelli CR, et al. 2013. Biotransformation of ent-pimaradienoic acid by cell cultures of Aspergillus niger. Bioorg Med Chem. 21(18):5870–5875.10.1016/j.bmc.2013.07.009
  • Shanmugaprakash M, Kirthika J, Ragupathy J, Nilanee K, Manickam A. 2014. Statistical based media optimization and production of naringinase using Aspergillus brasiliensis 1344. Int J Biol Macromol. 64(1):443–452.10.1016/j.ijbiomac.2013.12.033
  • Silva MLA, Coímbra HS, Pereira AC, Almeida VA, Lima TC, Costa ES, Vinhólis AHC, Royo VA, Silva R, Filho AAS, et al. 2007. Evaluation of piper cubeba extract, (-)-cubebin and its semi-synthetic derivatives against oral pathogens. Phytother Res. 21(5):420–422.10.1002/(ISSN)1099-1573
  • Srisilam K, Veeresham C. 2003. Biotransformation of drugs by microbial cultures for predicting mammalian drug metabolism. Biotechnol Adv. 21(1):3–39.10.1016/S0734-9750(02)00096-4
  • Sura MB, Ankireddy M, Ponnapalli MG. 2015. Biotransformation of agallochaexcoerin A by Aspergillus flavus. Nat Prod Res. 29(9):838–841.10.1080/14786419.2014.989845
  • Vander Heyden Y, Nijhuis A, Smeyers-Verbeke J, Vandeginste BGM, Massart DL. 2001. Guidance for robustness/ruggedness tests in method validation. J Pharm Biomed Anal. 24(5–6):723–753.10.1016/S0731-7085(00)00529-X
  • Wada K, Munakata K. 1970. (-)-Parabenzlactone, a new piperolignanolide isolated from parabenzoin Trilobum nakai. Tetrahedron Lett. 11(23):2017–2019.10.1016/S0040-4039(01)98142-0
  • Yam J, Kreuter M, Drewe J. 2008. Piper cubeba targets multiple aspects of the androgen-signalling pathway. A potential phytotherapy against prostate cancer growth. Planta Med. 74(1):33–38.10.1055/s-2007-993758
  • Zhang J, Guo H, Tian Y, Liu P, Li N, Zhou J, Guo D. 2007. Production of gastrodin through biotransformation of p - 2- hydroxybenzyl alcohol by cultured cells of Armillaria luteo-virens Sacc. Phytochemistry. 68(20):2523–2530.10.1016/j.phytochem.2007.05.028
  • Zhao W, Li H, Tang Y, Liang X, Wan D, Tang Y. 2012. Optimization of a biotransformation process to produce 4- (2, 3, 5, 6-tetramethylpyrazine-1) -4′-demethylepipodophyllotoxin. Process Biochem. 47(11):1522–1531.10.1016/j.procbio.2012.04.016

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.