Medicinal Chemistry Research

, Volume 26, Issue 4, pp 849–855 | Cite as

α-Glucosidase inhibitory and antioxidant activity of furanocoumarins from Heracleum persicum

  • Hossein Dehghan
  • Yaghoub Sarrafi
  • Peyman Salehi
  • Samad Nejad Ebrahimi
Original Research


As a part of ongoing project on biological screening of about a hundred plant extracts from Iran, the significant inhibitory effect of n-hexane extract of roots of Heracleum persicum on α-glucosidase and its 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity were revealed. The present study was designed to evaluate the antidiabetic and antioxidant activities of various extracts of roots of Heracleum persicum and isolation of ten furanocoumarin and a rare furanocoumarin-dimer type compounds through “bioassay guided fractionation” method. The structures were elucidated by 1D and 2D NMR, EI-MS, and HRESI-MS data as psoralen (1), bergapten (2), xanthotoxin (3), isopimpinellin (4), angelicin (5), isobergapten (6), sphondin (7), pimpinellin (8), heratomin (9), 5-methoxyheratomin (10), moellendorffiline (11), and fraxetin (12). Moellendorffiline (11) with the IC50 value of 17.9 nM showed significant inhibitory activity against α-glucosidase, more potent than acarbose (IC50 = 23.5 nM) and also exhibited high antioxidant activity (IC50 = 0.2 μM), compared with butylated hydroxytoluene (IC50 = 0.1 μM).


Heracleum persicum α-Glucosidase inhibition DPPH Furanocoumarin Moellendorffiline 


Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.


  1. Asgarpanah J, Dadashzadeh Mehrabani G, Ahmadi M, Ranjbar R, Safi-Aldin Ardebily M (2012) Chemistry, pharmacology and medicinal properties of Heracleum persicum Desf. Ex Fischer: a review. J Med Plants Res 6:1813–1820Google Scholar
  2. Bastaki S (2005) Diabetes mellitus and its treatment. Int J Diabetes Metab 13:111–134Google Scholar
  3. Dehghan H, Sarrafi Y, Salehi P (2016) Antioxidant and antidiabetic activities of 11 herbal plants from Hyrcania region, Iran. J Food Drug Anal 24(1):179–188CrossRefGoogle Scholar
  4. Demet D, Seda Damla H, Ahmet Ceyhan G, Gulacti T (2013) Anticholinesterase furocoumarins from Heracleum platytaenium, a species endemic to the Ida Mountains. Turk J Chem 37:675–683Google Scholar
  5. De Oliveira P, Conserva L, Brito A, Lemos R (2005) Coumarin derivatives from Esenbeckia grandiflora and its larvicidal activity against Aedes aegypti. Pharm Biol 43(1):53–57CrossRefGoogle Scholar
  6. De Oliveira P, Conserva L, De Simone C, Pereira M, Malta V, Imbroisi D (2004) A pimpinellin monomer and dimer isolated from the roots of Esenbeckia grandiflora. Acta Crystallogr C 60(12):900–902Google Scholar
  7. Dewick PM (2002) Medicinal natural products: a biosynthetic approach, 2nd edn. Wiley, USAGoogle Scholar
  8. Firuzi O, Asadollahi M, Gholami M, Javidnia K (2010) Composition and biological activities of essential oils from four Heracleum species. Food Chem 122(1):117–122CrossRefGoogle Scholar
  9. Gupta BD, Banerjee SK, Handa KL, Atal CK (1976) Heratomin and heratomol, new coumarins from Heracleum thomsoni. Phytochemistry 15(8):1319–1320CrossRefGoogle Scholar
  10. Hajhashemi V, Sajjadi SE, Heshmati M (2009) Anti-inflammatory and analgesic properties of Heracleum persicum essential oil and hydroalcoholic extract in animal models. J Ethnopharmacol 124(3):475–480CrossRefPubMedGoogle Scholar
  11. Hemati A, Azarnia M, Angaji A (2010) Medicinal effects of Heracleum persicum (Golpar). Middle-East J Sci Res 5(3):174–176Google Scholar
  12. Hung H-Y, Qian K, Morris-Natschke SL, Hsu C-S, Lee K-H (2012) Recent discovery of plant-derived anti-diabetic natural products. Nat Prod Rep 29(5):580–606CrossRefPubMedGoogle Scholar
  13. Hwang IG, Kim HY, Woo KS et al. (2011) Isolation and characterisation of an α-glucosidase inhibitory substance from fructose–tyrosine Maillard reaction products. Food Chem 127(1):122–126CrossRefGoogle Scholar
  14. Johnson JA, Webster D, Gray CA (2013) The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. J Ethnopharmacol 147(1):232–237CrossRefPubMedGoogle Scholar
  15. Krentz AJ, Bailey CJ (2005) Oral antidiabetic agents. Drugs 65(3):385–411CrossRefPubMedGoogle Scholar
  16. Li W, Zheng H, Bukuru J, De Kimpe N (2004) Natural medicines used in the traditional Chinese medical system for therapy of diabetes mellitus. J Ethnopharmacol 92(1):1–21CrossRefPubMedGoogle Scholar
  17. Lin C, Huang Y, Chien M, Sheu S, Chen C (2007) Analysis of bakuchiol, psoralen and angelicin in crude drugs and commercial concentrated products of Fructus Psoraleae. J Food Drug Anal 15(4):433Google Scholar
  18. Liu R, Feng L, Sun A, Kong L (2004) Preparative isolation and purification of coumarins from Cnidium monnieri (L.) Cusson by high-speed counter-current chromatography. J Chromatogr A 1055(1):71–76CrossRefPubMedGoogle Scholar
  19. Liu R, Sun Q, Sun A, Cui J (2005) Isolation and purification of coumarin compounds from Cortex fraxinus by high-speed counter-current chromatography. J Chromatogr A 1072(2):195–199CrossRefPubMedGoogle Scholar
  20. Mozaffarian V (2012) Identification of medicinal and aromatic plants of Iran. Farhang Moaser, IranGoogle Scholar
  21. Niu X-M, Li S-H, Jiang B, Zhao Q-S, Sun H-D (2002) Constituents from the roots of Heracleum rapula Franch. J Asian Nat Prod Res 4(1):33–41CrossRefPubMedGoogle Scholar
  22. Noudeh GD, Sharififar F, Noodeh AD et al. (2010) Antitumor and antibacterial activity of four fractions from Heracleum persicum Desf. and Cinnamomum zeylanicum Blume. J Med Plants Res 4:2176–2180Google Scholar
  23. Omidbaigi R (2012) Production and processing of medicinal plants, 6th edn.. Astan Quds Publication, Tehran, vol 2Google Scholar
  24. Pazdro R, Burgess JR (2010) The role of vitamin E and oxidative stress in diabetes complications. Mech Ageing Dev 131(4):276–286CrossRefPubMedGoogle Scholar
  25. Rahimi R, Nikfar S, Larijani B, Abdollahi M (2005) A review on the role of antioxidants in the management of diabetes and its complications. Biomed Pharmacother 59(7):365–373CrossRefPubMedGoogle Scholar
  26. Ramesh B, Pugalendi KV (2006) Antihyperglycemic effect of umbelliferone in streptozotocin-diabetic rats. J Med Food 9(4):562–566CrossRefPubMedGoogle Scholar
  27. Rao G, Dai W, Yang Q, Dai Y, Liu Q, Sun H (1995) Chemical constituents of Pleurospermum govanianum (Wall ) Benth ex C. B. Clarke var. bicolor Wolff. China J Chinese Materia Medica 20(12):740–742Google Scholar
  28. Rawat A, Singh A, Singh D, Pandey M, Govindarajan R, Srivastava S (2013) Separation and identification of furocoumarin in fruits of Heracleum candicans DC. by HPTLC. J Chem 2013:1–4Google Scholar
  29. Shalaby NM, Abd-Alla HI, Aly HF, Albalawy MA, Shaker KH, Bouajila J (2014) Preliminary in vitro and in vivo evaluation of antidiabetic activity of Ducrosia anethifolia Boiss. and its linear furanocoumarins. BioMed Res Int 2014Google Scholar
  30. Shim SC, Jeong BM, Paik YH (1992) Photodimerization of 5,7-Dimethoxycoumarin. B Kor Chem Soc 13:684–688Google Scholar
  31. Shokri H, Sharifzadeh A, Tamai IA (2012) Anti-Candida zeylanoides activity of some Iranian plants used in traditional medicine. J Med Mycol 22(3):211–216CrossRefGoogle Scholar
  32. Stevenson PC, Simmonds MS, Yule MA et al. (2003) Insect antifeedant furanocoumarins from Tetradium daniellii. Phytochemistry 63(1):41–46CrossRefPubMedGoogle Scholar
  33. Surya S, Salam AD, Tomy DV, Carla B, Kumar RA, Sunil C (2014) Diabetes mellitus and medicinal plants-a review. Asian Pac J Trop Dis 4(5):337–347CrossRefGoogle Scholar
  34. Um YR, Kong C-S, Im Lee J, Kim YA, Nam TJ, Seo Y (2010) Evaluation of chemical constituents from Glehnia littoralis for antiproliferative activity against HT-29 human colon cancer cells. Process Biochem 45(1):114–119CrossRefGoogle Scholar
  35. Wulff WD, McCallum JS, Kunng FA (1988) Two regiocomplementary approaches to angular furanocoumarins with chromium carbene complexes: synthesis of sphondin, thiosphondin, heratomin, and angelicin. J Am Chem Soc 110(22):7419–7434CrossRefGoogle Scholar
  36. Xu X, Xie H, Wang Y, Wei X (2010) A-type proanthocyanidins from lychee seeds and their antioxidant and antiviral activities. J of Agr Food Chem 58(22):11667–11672CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Hossein Dehghan
    • 1
  • Yaghoub Sarrafi
    • 2
  • Peyman Salehi
    • 3
  • Samad Nejad Ebrahimi
    • 3
  1. 1.Medicinal Plants Research CenterShahed UniversityTehranIran
  2. 2.Department of Organic Chemistry, Faculty of ChemistryUniversity of MazandaranBabolsarIran
  3. 3.Department of PhytochemistryMedicinal Plants and Drugs Research Institute, Shahid Beheshti UniversityTehranIran

Personalised recommendations