Download PDF
Planta Med 2016; 82(11/12): 1105-1109
DOI: 10.1055/s-0042-108738
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Efficient Isolation of Dihydropyranocoumarins and Simple Coumarins from Mutellina purpurea Fruits[*]

Krystyna Skalicka-Woźniak
1   Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, Lublin, Poland
,
Tomasz Mroczek
1   Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, Lublin, Poland
,
Magdalena Walasek
1   Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, Lublin, Poland
,
Kazimierz Głowniak
1   Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, Lublin, Poland
2   Department of Cosmetology, University of Information Technology and Management in Rzeszow, Rzeszow, Poland
› Author Affiliations
Further Information

Publication History

received 26 February 2016
revised 23 April 2016

accepted 02 May 2016

Publication Date:
10 June 2016 (online)

    Permissions and Reprints

Abstract

For the first time, the separation of coumarin derivatives from the petroleum ether extract of the fruits of Mutellina purpurea through high-performance countercurrent chromatography (HPCCC) is described. Four compounds, pteryxin (1; 2.72 mg), hyuganin C (2; 7.94 mg), osthol (3; 4.30 mg), and hyuganin A (4; 3.09 mg), were obtained in a single run following the injection of crude extract (300 mg). Additionally, auraptenol (5) and hyuganin D (6) were identified using LC-ESI-(Q)TOF-MS. The structures of the isolated compounds were elucidated through spectroscopic (NMR and MS) methods. This is apparently the first report of the identification of dihydropyranocoumarins in this plant, and the first time that HPCCC was used to separate them.

Key words

Mutellina purpurea - Apiaceae - high-performance countercurrent chromatography - dihydropyranocoumarins - coumarins - spectroscopic analysis

* Dedicated to Professor Dr. Dr. h. c. mult. Kurt Hostettmann in recognition of his outstanding contribution to natural product research.


Supporting Information

 

  • References

  • 1 Sieniawska E, Baj T, Dudka J, Gieroba R, Swiatek L, Rajtar B, Glowniak K, Polz-Dacewicz M. Cytotoxicity, antioxidant activity and an effect on CYP3A4 and CYP2D6 of Mutellina purpurea L. extracts. Food Chem Toxicol 2013; 52: 188-192
    CrossrefPubMedGoogle Scholar
  • 2 Sieniawska E, Głowniak K. Identification of the coumarin compounds in the Mutellina purpurea extracts. Annales UMCS Sectio DDD 2011; 2: 97-104
    PubMedGoogle Scholar
  • 3 Sieniawska E, Swatko-Ossor M, Sawicki R, Ginalska G. Morphological changes in the overall Mycobacterium tuberculosis H37 Ra cell shape and cytoplasm homogeneity due to Mutellina purpurea L. essential oil and its main constituents. Med Princ Pract 2015; 24: 527-532
    CrossrefPubMedGoogle Scholar
  • 4 Sieniawska E, Los R, Baj T, Malm A, Glowniak K. Antimicrobial efficacy of Mutellina purpurea essential oil and pinene against Staphylococcus epidermidis grown in planktonic and biofilm cultures. Ind Crop Prod 2013; 51: 152-157
    CrossrefPubMedGoogle Scholar
  • 5 Jędrzejko K. Medicinal Plants and herbal Materials in Use in Poland: a Check List. Katowice: Silesian Medical University; 2001
    Google Scholar
  • 6 Passreiter CM, Akhtar Y, Isman MB. Insecticidal activity of the essential oil of Ligusticum mutellina roots. Z Naturforsch C 2005; 60: 411-414
    PubMedGoogle Scholar
  • 7 Baj T, Sieniawska E, Kowalski R, Wesolowski M, Ulewicz-Magulska B. Effectiveness of the Deryng and Clevenger-type apparatus in isolation of various types of components of essential oil from the Mutellina purpurea Thell. flowers. Acta Pol Pharm 2015; 72: 507-515
    PubMedGoogle Scholar
  • 8 Sieniawska E, Skalicka-Woźniak K. Isolation of chlorogenic acid from Mutellina purpurea L. herb using high-performance counter-current chromatography. Nat Prod Res 2014; 28: 1936-1939
    CrossrefPubMedGoogle Scholar
  • 9 Skalicka-Woźniak K, Orhan IE, Cordell GA, Nabavi SM, Budzyńska B. Implication of coumarins towards central nervous system disorders. Pharmacol Res 2016; 103: 188-203
    CrossrefPubMedGoogle Scholar
  • 10 Sutherland IA. Recent progress on the industrial scale-up of counter-current chromatography. J Chromatogr A 2007; 1151: 6-13
    CrossrefPubMedGoogle Scholar
  • 11 Skalicka-Woźniak K, Garrard I. A comprehensive classification of solvent systems used for natural product purifications in counter-current and centrifugal partition chromatography. Nat Prod Rep 2015; 32: 1556-1561
    CrossrefPubMedGoogle Scholar
  • 12 Jarząb A, Grabarska A, Kiełbus M, Jeleniewicz W, Dmoszyńska-Graniczka M, Skalicka-Woźniak K, Sieniawska E, Polberg K, Stepulak A. Osthole induces apoptosis, suppresses cell-cycle progression and proliferation of cancer cells. Anticancer Res 2014; 34: 6473-6480
    PubMedGoogle Scholar
  • 13 Chen IS, Changa CT, Sheena WS, Teng CM, Tsai IL, Duh CY, Ko FN. Coumarins and antiplatelet aggregation constituents from Formosan Peucedanum japonicum . Phytochemistry 1996; 41: 525-530
    CrossrefPubMedGoogle Scholar
  • 14 Matsuda H, Murakami T, Nishida N, Kageura T, Yoshikawa M. Medicinal foodstuffs. XX. Vasorelaxant active constituents from the roots of Angelica furcijuga Kitagawa: structures of hyuganins A, B, C, and D. Chem Pharm Bull (Tokyo) 2000; 48: 1429-1435
    CrossrefPubMedGoogle Scholar
  • 15 Naseri M, Monsef-Esfehani HR, Saeidnia S, Dastan D, Gohari AR. Antioxidative coumarins from the roots of Ferulago subvelutina . Asian J Chem 2013; 4: 1875-1878
    PubMedGoogle Scholar
  • 16 Imai F, Kinoshita T, Sankawa U. Constituents of the leaves of Murraya paniculata collected in Taiwan. Chem Pharm Bull 1989; 37: 358-362
    CrossrefPubMedGoogle Scholar
  • 17 Zhou P, Takaishi Y, Duan H, Chen B, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Lee KH. Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry 2000; 53: 689-697
    CrossrefPubMedGoogle Scholar
  • 18 Matsuda H, Murakami T, Kageura T, Ninomiya K, Toguchida I, Nishida N, Yoshikawa M. Hepatoprotective and nitric oxide production of coumarin and polyethylene constituents Angelica furcijuga inhibitory activities from the roots of Hisashi. Bioorg Med Chem Lett 1998; 8: 2191-2196
    CrossrefPubMedGoogle Scholar
  • 19 Jang KC, Kim SC, Song EY, Um YC, Kim SC, Lee YJ. Isolation and identification of anticancer and anti-inflammatory substances in Peucedanum japonicum Thunb. Acta Hortic 2008; 765: 49-53
    PubMedGoogle Scholar
  • 20 Mohammadi M, Yousefi M, Habibi Z, Shafiee A. Two new coumarins from the chloroform extract of Angelica urumiensis from Iran. Chem Pharm Bull (Tokyo) 2010; 58: 546-548
    CrossrefPubMedGoogle Scholar
  • 21 Farooq S, Shakeel-u-Rehman. Dangroo NA, Priya D, Banday JA, Sangwan PL, Qurishi MA, Koul S, Saxena AK. Isolation, cytotoxicity evaluation and HPLC-quantification of the chemical constituents from Prangos pabularia . PLoS One 2014; 9: e0108713
    PubMedGoogle Scholar
  • 22 Nugara RN, Inafuku M, Takara K, Iwasaki H, Oku H. Pteryxin: a coumarin in Peucedanum japonicum Thunb. leaves exerts antiobesity activity through modulation of adipogenic gene network. Nutrition 2014; 10: 1177-1184
    PubMedGoogle Scholar
  • 23 Akihisa T, Tokud H, Ukiya M, Iizuka M, Schneider S, Ogasawara K, Mukainaka T, Iwatsuki K, Suzuki T, Nishino H. Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects. Cancer Lett 2003; 201: 133-137
    CrossrefPubMedGoogle Scholar