2,253
Views
39
CrossRef citations to date
0
Altmetric
Research Article

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

, , , , , , , , & show all
Pages 1173-1179 | Received 11 Feb 2011, Accepted 24 Mar 2011, Published online: 21 Oct 2011

References

  • Atsumi T, Fujisawa S, Satoh K, Sakagami H, Iwakura I, Ueha T, Sugita Y, Yokoe I. (2000). Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimers. Anticancer Res, 20, 2519–2524.
  • Baker DD, Chu M, Oza U, Rajgarhia V. (2007). The value of natural products to future pharmaceutical discovery. Nat Prod Rep, 24, 1225–1244.
  • Barreiro EJ, Fraga CAM. A. (1999). A utilização do safrol, principal componente químico do óleo de sassafráz, na síntese de substâncias bioativas na cascata do ácido araquidônico: antiinflamatórios, analgésicos e antitrombóticos. Quím Nova, 22, 744–759.
  • Bastos CN. (1997). Efeito do óleo de P. aduncum sobre Crinipellis perniciosa e outros fungos fitopatogênicos. Fitopatol Bras, 3, 441–443.
  • Belzile AS, Majerus SL, Podeszfinski C, Guillet G, Durst T, Arnason JT. (2000). Dillapiol derivatives as synergists: Structure-activity relationship analysis. Pestic Biochem Physiol, 66, 33–36.
  • Bernard CB, Krishinamurty HG, Chauret D, Durst T, Philogene BJR, Sanchés-Vindas P, Hasbaun C, Poveda L, Roman LS, Arnason JT. (1995). Insecticidal defenses of Piperaceae from the neotropics. J Chem Ecol, 21, 801–814.
  • Bonthrone W, Cornforth JW. (1969). The methylenation of catechols. J Chem Soc, 1, 1202–1204.
  • Cicció JF, Ballestero CM. (1997). Constituyntes volátiles de las hojas y espigas de Piper aduncum (Piperaceae) da Costa Rica. Rev Biol Trop, 45, 783–793.
  • Costa PRR. (2000). Safrol e eugenol: Estudo da reatividade química e uso em síntese de produtos naturais biologicamente ativos e seus derivados. Quím Nova, 23, 357–369.
  • Diaz PP, Ramos BC, Matta GE. (1986). New C6-C3 and C6-C1 compounds from Piper lenticellosum. J Nat Prod, 49, 690–691.
  • Duke JA. (1985). Handbook of medicinal herbs. New York: CRC Press.
  • Fazolin M, Estrela JLV, Catani V, Alécio MR, Lima MS. (2007). Propriedade inseticida dos óleos essenciais de Piper hispidinervum C. DC.; Piper aduncum L. e Tanaecium nocturnum (Barb. Rodr.) Bur. & K. Shum sobre Tenebrio molitor L., 1758. Cienc Agrotec, 31, 113–115.
  • Fazolin M, Estrela JLV, Catani V, Lima MS, Alécio, MR. (2005). Toxicidade do óleo de Piper aduncum L. a adultos de Cerotoma tingomarianus Bechyné (Coleóptera: Chrysomelidae). Neotrop Entomol, 34, 485–489.
  • Gaia JMD, Mota MGC, Conceição CCC, Costa MR, Maia JGS. (2004). Similaridade genética de populações naturais de pimenta-de-macaco por análise RAPD. Horticult Bras, 22, 686–689.
  • Green TP, Treadwell EM, Wiemer DF. (1999). Arieianal, a prenylated benzoic acid from Piper arieianum. J Nat Prod, 62, 367–368.
  • Hanessian S. (2006). Structure-based organic synthesis of drug prototypes: A personal odyssey. Chemmedchem, 1, 1301–1330.
  • Lago JH, Soares MG, Batista-Pereira LG, Silva MF, Corrêa AG, Fernandes JB, Vieira PC, Roque NF. (2006). Volatile oil from Guarea macrophylla ssp. tuberculata: Seasonal variation and electroantennographic detection by Hypsipyla grandella. Phytochemistry, 67, 589–594.
  • Lago JH, Ramos CS, Casanova DC, Morandim Ade A, Bergamo DC, Cavalheiro AJ, Bolzani Vda S, Furlan M, Guimarães EF, Young MC, Kato MJ. (2004). Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum. J Nat Prod, 67, 1783–1788.
  • Lago JHG, Tanizaki TM, Young MCM, Guimarães EF, Kato MJ. (2005). Antifungal piperolides from Piper malacophyllum (Prels) C. DC. J Braz Chem Soc, 16, 153–156.
  • Lima MEF, Gabriel AJA, Castro RN. (2000). Synthesis of a new strigol analogue from natural safrole. J Braz Chem Soc, 11, 371–375.
  • Lobato AKS, Santos DGC, Oliveira FC, Gouvêa DDS, Torres GIOS, Lima-Junior JA, Oliveira-Neto CF, Silva MHL. (2007). Ação do óleo essencial de Piper aduncum L. utilizada como fungicida natural no tratamento de sementes de Vigna unguiculata (L.) Walp. Rev Bras Biocien, 5, 915–919.
  • Maia JGS, Zoghbi MGS, Andrade EHA, Santos AS, Silva ML, Luz AIR, Bastos CN. (1998). Constituintes of the essential oil of Piper aduncum L. growing in the Amazon Region. Flav Frag J, 13, 269–272.
  • Majerus SL, Alibhai N, Tripathy S, Durst T. (2000). New syntheses of dillapiol [4,5-dimethoxy-6-(2-propenyl)-1,3-benzodioxole], its 4-methylthio and other analogs. Can J Chem, 78, 1345–1351.
  • Masuda T, Inazumi A, Yamada Y, Padolina WG, Kikuzaki H, Nakatani N. (1991). Constituints of Piperaceae 4. Antimicrobial phenylpropanoids from Piper sarmentosum. Phytochemistry, 30, 3227–3228.
  • Maxwell A, Rampersad D. (1989). A new amide from Piper demeraranum. J Nat Prod, 52, 891–892.
  • Meléndez PA, Capriles VA. (2006). Antibacterial properties of tropical plants from Puerto Rico. Phytomedicine, 13, 272–276.
  • Montanari CA, Bolzani VS. (2001). Planejamento racional de fármacos baseado em produtos naturais. Quím Nova, 24, 105–111.
  • Monteiro GM, Lira DS, Maia JGS, Barros CAL, Sousa PJC. (2001). Acute and subacute toxicity of the essential oil of Piper aduncum. Eur J Pharm Sci, 13, S153–S160.
  • Moreira DL, Souza PO, Kaplan MA, Pereira NA, Cardoso GL, Guimarães EF. (2001). Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour. An Acad Bras Cienc, 73, 33–37.
  • Narisada M, Horibe I, Watanabe F, Takeda F. (1989). Selective reduction of aryl halides and α,β-unsaturated esters with sodium borohydride-cuprous chloride in methanol and its application to deuterium labeling. J Org Chem, 54, 5308–5311.
  • Newman DJ, Cragg GM, Snader KM. (2000). The influence of natural products upon drug discovery. Nat Prod Rep, 17, 215–234.
  • Okunade AL, Hufford CD, Clark AM, Lentz D. (1997). Antimicrobial properties of the constituents of Piper aduncum. Phytother Res, 11, 142–144.
  • Orjala J, Erdelmeier CAJ, Wright AD, Rali T, Sticher O. (1993). Chromenes and prenylated benzoic-acid derivative from Piper aduncum. Phytochemistry, 34, 818–821.
  • Orjala J, Erdelmeier CAJ, Wright AD, Rali T, Sticher O. (1994). Cytotoxic and antibacterial dihydrochalcones from Piper aduncum. J Nat Prod, 57, 18–22.
  • Parmar V, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, Tyagi OD, Prasad AK, Wengel J, Olsen CE, Boll PM. (1997). Phytochemistry of the genus Piper. Phytochemistry, 46, 597–673.
  • Sengupta S, Ray AB. (1987). The chemistry of Piper species: A review. Fitoterapia, 63, 147–166.
  • Shulgin AT. (1966). Possible implication of myristicin as a psychotropic substance. Nature, 210, 380–384.
  • Sousa PJC, Barros CAL, Rocha JCS, Lira SS, Monteiro GM, Maia JGS. (2008). Avaliação toxicológica do óleo essencial de Piper aduncum L. Rev Bras Farmacogn, 18, 10–13.
  • Viegas-Junior C, Bolzani VS, Barreiro EJ. (2006). Os produtos naturais e a química medicinal moderna. Quím Nova, 29, 326–337.
  • Winter CA, Risley EA, Nuss GW. (1962). Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med, 111, 544–547.
  • Yunker TG. (1972). The Piperaceae of Brazil: I- Piper- Group I, II, III, IV. Hohenia, 2, 19–366.

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.