Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 36, 2022 - Issue 9
547
Views
2
CrossRef citations to date
0
Altmetric
Short Communications

Adiantic acid, a new unsaturated fatty acid with a cyclopropane moiety from Adiantum flabellulatum L.

, , , , , & ORCID Icon show all
Pages 2386-2392 | Received 23 Jun 2020, Accepted 06 Sep 2020, Published online: 05 Oct 2020

References

  • Aïssa C, Crépin D, Tetlow DJ, Ho KYT. 2013. Multiple Rhodium-catalyzed cleavages of single C-C bonds. Org Lett. 15(6):1322–1325.
  • Anselmi C, Centini M, Fedeli P, Paoli ML, Sega A, Scesa C, Pelosi P. 2000. Unsaturated hydrocarbons with fruity and floral odors. J Agric Food Chem. 48(4):1285–1289.
  • Bailey ML, Nixon JE, Hendricks JD, Pawlowski NE, Loveland PM, Sinnhuber RO. 1979. Comparative effects of sterculic and malvalic acids on the hepatic cytochrome-P-450 system and tumor induction in rainbow-trout. Fed Proc. 38(3):394–394.
  • Cao H, Chai T-T, Wang X, Morais-Braga MFB, Yang J-H, Wong F-C, Wang R, Yao H, Cao J, Cornara L, et al. 2017. Phytochemicals from fern species: potential for medicine applications. Phytochem Rev. 16(3):379–440.
  • Castellucci NT, Griffin CE. 1960. Synthesis of sterculic acid. J Am Chem Soc. 82(15):4107–4107.
  • Clark JR, Kircher HW. 1972. Synthesis and biological characterization of 10,11-methylene-9-nonadecene - analog of sterculic acid. Lipids. 7(12):769–772.
  • Della GM, Della GM. 1990. Stigmasterols from Typha latifolia. J Nat Prod. 53(6):1430–1435.
  • Fermor BF, Masters JRW, Wood CB, Miller J, Apostolov K, Habib NA. 1992. Fatty acid composition of normal and malignant cells and cytotoxicity of stearic, oleic and sterculic acids in vitro. Eur J Cancer. 28A(6–7):1143–1147.
  • Gensler WJ, Floyd MB, Yanase R, Pober KW. 1969. Synthesis of methyl sterculate. J. Am. Chem. Soc. 91(9), 2397–2398.
  • Hernando J, Matia MP, Novella JL, Alvarez-Builla J. 2002. Synthesis of sterculic acid. Arkivoc. 2002(5):27–31.
  • Huang J-D, Amaral J, Lee JW, Larrayoz IM, Rodriguez IR. 2012. Sterculic acid antagonizes 7-ketocholesterol-mediated inflammation and inhibits choroidal neovascularization. BBA - Mol Cell Biol Lipids. 1821(4):637–646.
  • Kang WY, Ji ZQ, Wang JM. 2009. Composition of the essential oil of Adiantum flabellulatum. Chem Nat Compd. 45(4):575–577.
  • Kapat A, Nyfeler E, Giuffredi GT, Renaud P. 2009. Intramolecular Schmidt reaction involving primary azidoalcohols under nonacidic conditions: synthesis of indolizidine (-)-167B. J Am Chem Soc. 131(49):17746–17747.
  • Khoo DE, Fermor B, Miller J, Wood CB, Apostolov K, Barker W, Williamson RCN, Habib NA. 1991. Manipulation of body fat composition with sterculic acid can inhibit mammary carcinomas in vivo. Br J Cancer. 63(1):97–101.
  • Li FW, Brouwer P, Carretero-Paulet L, Cheng S, de Vries J, Delaux PM, Eily A, Koppers N, Kuo LY, Li Z, et al. 2018. Fern genomes elucidate land plant evolution and cyanobacterial symbioses. Nat Plants. 4(7):460–472.
  • Macfarlane JJ, Shenstone FS, Vickery JR. 1957. Malvalic acid and its structure. Nature. 179(4564):830–831.
  • MacMillan JB, Molinski TF. 2005. Majusculoic acid, a brominated cyclopropyl fatty acid from a marine cyanobacterial mat assemblage. J Nat Prod. 68(4):604–606.
  • Mccarthy FO, Chopra J, Ford A, Hogan SA, Kerry JP, O'Brien NM, Ryan E, Maguire AR. 2005. Synthesis, isolation and characterisation of beta-sitosterol and beta-sitosterol oxide derivatives. Org Biomol Chem. 3(16):3059–3065.
  • Nemoto T, Ojika M, Sakagami Y. 1997. Amphimic acids, novel unsaturated C28 fatty acids as DNA topoisomerase I inhibitors from an Australian sponge Amphimedon sp. Tetrahedron Lett. 38(32):5667–5670.
  • Nemoto T, Yoshino G, Ojika M, Sakagami Y. 1997. Amphimic acids and related long-chain fatty acids as DNA topoisomerase I inhibitors from an Australian sponge, Amphimedon sp.: isolation, structure, synthesis, and biological evaluation. Tetrahedron. 53(49):16699–16710.
  • Pagar VV, RajanBabu TV. 2018. Tandem catalysis for asymmetric coupling of ethylene and enynes to functionalized cyclobutanes. Science. 361(6397):68–72.
  • Pan C, Chen YG, Ma XY, Jiang JH, He F, Zhang Y. 2012. Phytochemical constituents and pharmacological activities of plants from the genus Adiantum: a review. Trop J Pharma Res. 10(5):681–692.
  • Pelaez R, Pariente A, Perez-Sala A, Larrayoz IM. 2020. Sterculic acid: the mechanisms of action beyond stearoyl-CoA desaturase inhibition and therapeutic opportunities in human diseases. Cells-Basel. 9(1):140.
  • Samuel W, Kutty RK, Duncan T, Redmond TM. 2010. Inhibition of N-(4-Hydroxyphenyl)retinamide-induced apoptosis in human retinal pigment epithelial cells by sterculic acid, a stearoyl coenzyme a desaturase inhibitor. Invest Ophth Vis Sci. 51(13):4815.
  • Shahriar M, Kabir S. 2011. Analgesic activity of Adiantum flabellulatum. Dhaka Univ J Biol Sci. 20(1):91–93.
  • Shea KJ, Wise S. 1978. Synthesis and thermal rearrangements of methylenecyclobutanes. J Org Chem. 43(13):2710–2711.
  • Shibamoto S, Murata T, Yamamoto K. 2016. Determination of double bond positions and geometry of methyl linoleate isomers with dimethyl disulfide adducts by GC/MS. Lipids. 51(9):1077–1081.
  • Shiojima K, Arai Y, Kasama T, Ageta H. 1993. Fern constituents: triterpenoids isolated from the leaves of Adiantum monochlamys. Filicenol A, filicenol B, isoadiantol B, hakonanediol and epihakonanediol. Chem Pharm Bull. 41(2):262–267.
  • Subha R, Mohan PM, Singh RAK. 2018. Ethnopharmacological uses, phytochemistry and pharmacology of genus Adiantum: a comprehensive review. J Ethnopharmacol. 215:101–119.
  • Tomer KB, Crow FW, Gross ML. 1983. Location of double bond position in unsaturated fatty acids by negative ion MS/MS. J Am Chem Soc. 105(16):5487–5488.
  • Verma JP, Nath B, Aggarwal JS. 1955. Structure of sterculic acid. Nature. 175(4445):84–85.

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.