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Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots

  • Penghua ShuEmail author
  • Junping Li
  • Yingying Fei
  • Huiqing Zhu
  • Mengzhu Yu
  • Anqi Liu
  • Haoying Niu
  • Simin Zou
  • Xialan Wei
  • Zhiyu Ju
  • Zhihong XuEmail author
Note
  • 136 Downloads

Abstract

Two undescribed phenolic compounds, angelicols A (1) and B (2) and one undescribed coumarin rhamnoside, angelicoside A (3), together with 17 known compounds (420) were isolated from the roots of Angelica dahurica. Their structures were characterized by physical data analyses such as NMR, HRESIMS, and X-ray diffraction. Compounds 2, 3, 5, 6 and L-ascorbic acid (positive control) exhibited obvious DPPH radical scavenging activities with IC50 values of 0.36 mM, 0.43 mM, 0.39 mM, 0.44 mM, 0.25 mM, respectively. At a concentration of 25 μM, all compounds showed weaker tyrosinase inhibition activities (%inhibition < 5%) than kojic acid (26.00 ± 0.67%, IC50 = 44.29 ± 0.06 μM).

Keywords

Angelica dahurica Tyrosinase X-ray diffraction Antioxidant 

Notes

Acknowledgements

We are grateful to Lanxiang Dai for the collection of Angelica dahurica roots and Prof. Lin Yang at Lanzhou University of Technology for the authentication of the plant material. This work was financially supported by National Natural Science Foundation of China (no. 21702178), Key Scientific Research Program in Universities of Henan Province (no. 18A350010), Undergraduate Training Program for Innovation and Entrepreneurship of Henan Province (nos. 201910480011, 201910480017), Science and Technology Project of Henan Province (no. 182102311108), and Excellent Young Key Teacher Funding Project of Xuchang University (no. 2017).

Supplementary material

11418_2019_1375_MOESM1_ESM.doc (1.9 mb)
Supplementary file1 (DOC 1983 kb)

References

  1. 1.
    Chinese Pharmacopoeia Commission (2015) Pharmacopoeia of the People’s Republic of China, vol I. Chemical Industry Press, Beijing, pp 105–106Google Scholar
  2. 2.
    Thanh PN, Jin WY, Song GY, Bae KH, Kang SS (2004) Cytotoxic coumarins from the root of Angelica dahurica. Arch Pharm Res 27:1211–1215CrossRefGoogle Scholar
  3. 3.
    Zhao XZ, Feng X, Jia XD, Wang M, Shan Y, Dong Y (2007) New coumarin glucoside from Angelica dahurica. Chem Nat Compd 43:399–401CrossRefGoogle Scholar
  4. 4.
    Seo WD, Kim JY, Ryu HW, Kim JH, Han SI, Ra JE, Seo KH, Jang KC, Lee JK (2013) Identification and characterisation of coumarins from the roots of Angelica dahurica and their inhibitory effects against cholinesterase. J Funct Foods 5:1421–1431CrossRefGoogle Scholar
  5. 5.
    Yang WQ, Song YL, Zhu ZX, Su C, Zhang X, Wang J, Shi SP, Tu PF (2015) Anti-inflammatory dimeric furanocoumarins from the roots of Angelica dahurica. Fitoterapia 105:187–193CrossRefGoogle Scholar
  6. 6.
    Bai Y, Li DH, Zhou TT, Qin NB, Li ZL, Yu ZG, Hua HM (2016) Coumarins from the roots of Angelica dahurica with antioxidant and antiproliferative activities. J Funct Foods 20:453–462CrossRefGoogle Scholar
  7. 7.
    Wei W, Wu XW, Deng GG, Yang XW (2016) Anti-inflammatory coumarins with short-and long-chain hydrophobic groups from roots of Angelica dahurica cv. Hangbaizhi. Phytochemistry 123:58–68CrossRefGoogle Scholar
  8. 8.
    Xie Q, Shun-Xiang L, Duan-Fang L, Wang W, Tekwani B, Hui-Yong H, Abbas ur Rehman AJ, Schrader KK, Duke SO (2016) Bio-pesticidal and antimicrobial coumarins from Angelica dahurica (Fisch. Ex Hoffm). Rec Nat Prod 10:294–306Google Scholar
  9. 9.
    Piao XL, Baek SH, Park MK, Park JH (2004) Tyrosinase-inhibitory furanocoumarin from Angelica dahurica. Biol Pharm Bull 27:1144–1146CrossRefGoogle Scholar
  10. 10.
    Qi B, Yang W, Ding N, Luo Y, Jia F, Liu X, Wang J, Wang X, Tu P, Shi S (2019) Pyrrole 2-carbaldehyde derived alkaloids from the roots of Angelica dahurica. J Nat Med 73:769–776CrossRefGoogle Scholar
  11. 11.
    Wang J, Lian P, Yu Q, Wei J, Kang WY (2017) Purification, characterization and procoagulant activity of polysaccharides from Angelica dahurice roots. Chem Cent J 11:17CrossRefGoogle Scholar
  12. 12.
    Zhao XZ, Feng X, Jia XD, Dong YF, Wang M (2007) Neolignan glycoside from Angelica dahurica. Chin Chem Lett 18:168–170CrossRefGoogle Scholar
  13. 13.
    Ishikawa T, Kondo K, Kitajima J (2003) Water-soluble constituents of coriander. Chem Pharm Bull 51:32–39CrossRefGoogle Scholar
  14. 14.
    Chang HS, Peng CJ, Cheng MJ, Wu HC, Chan HY, Hsieh SY, Yuan GF, Chen IS (2018) Chemical constituents of the endophytic fungus phomopsis asparagi isolated from the plant Peperomia sui. Chem Nat Compd 54:504–508CrossRefGoogle Scholar
  15. 15.
    Cheng MJ, Wu MD, Chan HY, Hsieh SY, Chen JJ, Chang HS, Kuo YH, Yuan GF, Chen IS (2018) A new benzenoid derivative from an endophytic fungus in Peperomia sui. Chem Nat Compd 54:625–627CrossRefGoogle Scholar
  16. 16.
    Ferraboschi P, Grisenti P, Manzocchi A, Santaniello E (1990) Bakers’ yeast-mediated preparation of optically active aryl alcohols and diols for the synthesis of chiral hydroxy acids. J Chem Soc Perkin Trans 1:2469–2474CrossRefGoogle Scholar
  17. 17.
    Kamal A, Chouhan G (2004) Chemoenzymatic synthesis of enantiomerically pure 1,2-diols employing immobilized lipase in the ionic liquid [bmim] PF6. Tetrahedron Lett 45:8801–8805CrossRefGoogle Scholar
  18. 18.
    Inoue A, Shibano M, Taniguchi M, Baba K, Wang NH (2011) Four novel furanocoumarin glucosides, candinosides A, B, C and D, from Heracleum candicans Wall. J Nat Med 65:116–121CrossRefGoogle Scholar
  19. 19.
    Cao SG, Wu XH, Sim KY, Tan BHK, Vittal JJ, Pereira JT, Goh SH (1998) Minor coumarins from Calophyllum teysmannii var. inophylloide and synthesis of cytotoxic calanone derivatives. Helv Chim Acta 81:1404–1416CrossRefGoogle Scholar
  20. 20.
    Zhang L, Lv J (2018) A new ferulic acid derivative and other anticoagulant compounds from Angelica sinensis. Chem Nat Compd 54:13–17CrossRefGoogle Scholar
  21. 21.
    Ishii H, Ishikawa T, Sekiguchi H, Hosoya K (1973) Xanthoarnol. New dihydrofuranocoumarin. Chem Pharm Bull 21:2346–2348CrossRefGoogle Scholar
  22. 22.
    Xin XL, Wang Y, Wang G, Wang C, Huang SS, Huo XK, Su DH, Tian XG (2018) Biotransformation of furanocoumarins by fungi: preparation of imperation analogs. J Asian Nat Prod Res 20:697–707CrossRefGoogle Scholar
  23. 23.
    Miyazawa M, Tsukamoto T, Anzai J, Ishikawa Y (2004) Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against drosophila melanogaster. J Agric Food Chem 52:4401–4405CrossRefGoogle Scholar
  24. 24.
    Abu-Mustafa EA, Fayez MBE (1967) Natural coumarins. VI. Nuclear magnetic resonance spectra of some coumarin and coumarilic acid derivatives. Can J Chem 45:325–327CrossRefGoogle Scholar
  25. 25.
    Di Stefano V, Pitonzo R, Schillaci D (2011) Chemical constituents and antiproliferative activity of Euphorbia bivonae. Chem Nat Compd 47:660–663CrossRefGoogle Scholar
  26. 26.
    Tavakoli S, Delnavazi MR, Hadjiaghaee R, Jafari-Nodooshan S, Khalighi-Sigaroodi F, Akhbari M, Hadjiakhoondi A, Yassa N (2018) Bioactive coumarins from the roots and fruits of Ferulago trifida Boiss., an endemic species to Iran. Nat Prod Res 32:2724–2728CrossRefGoogle Scholar
  27. 27.
    Geidarov IG, Serkerov SV (2017) Coumarins from roots of Angelica purpurascens. Chem Nat Compd 53:149–150CrossRefGoogle Scholar
  28. 28.
    Marumoto S, Miyazawa M (2012) Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor. Bioorg Med Chem Lett 20:784–788CrossRefGoogle Scholar
  29. 29.
    Zhao AH, Yang XB, Yang XW, Zhang YB, Xu W, Liu JX (2012) Biotransformation products of phellopterin by rat liver microsomes and the inhibition on NO production in LPS-activated RAW264.7 cells. J Asian Nat Prod Res 20:697–707Google Scholar
  30. 30.
    Marumoto S, Miyazawa M (2010) β-secretase inhibitory effects of furanocoumarins from the root of Angelica dahurica. Phytother Res 24:510–513PubMedGoogle Scholar
  31. 31.
    Naseri M, Monsef-Esfehani HR, Saeidnia S, Dastan D, Gohari AR (2013) Antioxidative coumarins from the roots of Ferulago subvelutina. Asian J Chem 25:1875–1878CrossRefGoogle Scholar
  32. 32.
    Ullah S, Park Y, Park C, Lee S, Kang D, Yang J, Akter J, Chun P, Moon HR (2019) Antioxidant, anti-tyrosinase and anti-melanogenic effects of (E)-2,3-diphenylacrylic acid derivatives. Bioorg Med Chem Lett 27:2192–2200CrossRefGoogle Scholar
  33. 33.
    Kim SJ, Yang J, Lee S, Park C, Kang D, Akter J, Ullah S, Kim YJ, Chun P, Moon HR (2018) The tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold. Bioorg Med Chem 26:3882–3889CrossRefGoogle Scholar
  34. 34.
    Heredia-Vieira SC, Simonet AM, Vilegas W, Macias FA (2015) Unusual C, O-fused glycosylapigenins from Serjania marginata Leaves. J Nat Prod 78:77–84CrossRefGoogle Scholar
  35. 35.
    Hyun SK, Lee WH, Jeong DM, Kim Y, Choi JS (2008) Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis. Biol Pharm Bull 31:154–158CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy 2019

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringXuchang UniversityXuchangPeople’s Republic of China
  2. 2.School of Information EngineeringXuchang UniversityXuchangPeople’s Republic of China

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