Fitoterapia 78 (2007) 448 – 449 www.elsevier.com/locate/fitote
Phytochemical communication
Coumarins from Peucedanum luxurians Ioanna Chinou a,⁎, Jaroslaw Widelski a,b , Nikolas Fokialakis a , Prokopios Magiatis a , Kazimierz Glowniak b a
Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, University of Athens, Athens 15771, Greece b Department of Pharmacognosy with Medicinal Plant Laboratory, Skubiszewski Medicinal University of Lublin, Poland Received 18 November 2005; accepted 3 April 2007 Available online 24 May 2007
Abstract Ten coumarins were isolated from Peucedanum luxurians. The rare coumarins stenocarpin, stenocarpin isobutyrate, officinalin, officinalin isobutyrate, 8-methoxypeucedanin and the known xanthotoxin, isoimperatorin, bergaptene, peucedanin and cnidilin were isolated. All isolated compound were identified by means of spectral data. © 2007 Elsevier B.V. All rights reserved. Keywords: Peucedanum luxurians; Coumarins; Spectral data
1. Plant Aerial parts of Peucedanum luxurians Tamam (Apiaceae) were collected from the Botanical Garden of the Department of Pharmacognosy (Medical University of Lublin, Poland). The seeds for cultivation came from the Hortus Botanicus, Universitatis, Posnaniensis, Poznan, Poland (Voucher specimen n. 2534). 2. Uses in traditional medicine Several plants of Peucedanum spp. are used, in Mediterranean area traditional medicine, for the treatment of asthma and angina [1]. 3. Previously isolated constituents Terpenes from the roots [2].
⁎ Corresponding author. Tel.: +30 210 7274595; fax: +30 210 7274115. E-mail address:
[email protected] (I. Chinou). 0367-326X/$ - see front matter © 2007 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2007.04.004
I. Chinou et al. / Fitoterapia 78 (2007) 448–449
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Fig. 1. The structures of compounds 1–10.
4. New isolated constituents 8-Methoxypeucedanin (1, 6 mg) [3], stenocarpin isobutyrate (2, 22 mg) [4], peucedanin (3, 4.3 mg) [5], officinalin isobutyrate (4, 7.4 mg) [5], isoimperatorin (5, 3.7 mg) [6], cnidilin (6, 5.7 mg) [7], bergapten (7, 4 mg) [8], xanthotoxin (8, 6 mg) [8], stenocarpin(9, 1 mg [4], and officinalin (10, 1 mg) [5] (Fig. 1). 8-Methoxypeucedanin (1). 1H NMR (CDCl3, 400 MHz): δ 7.74 (1H, d, J 9.7 Hz, H-4), 7.22 (1H, s, H-5), 6.34 (1H, d, J 9.7 Hz, H-3), 4.26 (3H, s, CH3O-8), 3.91 (3H, s, CH3O-6), 3.25 (1H, sept, J 7.0 Hz, H-1′), 1.35 (6H, d, J 7.0 Hz, H2′,3′). 13C NMR (CDCl3 50 MHz): δ 160.9 (C-2), 151.2 (C-7), 146.3 (C-7a), 144.0 (C-4), 142.3 (C-8a), 136.2 (C-6), 133.8 (C-8), 122.1 (C-5a), 117.3 (C-4a), 116.1 (C-3), 110.6 (C-5), 62.5 (C6-CH3O), 61.9 (C8-CH3O), 26.0 (C-1′), 21.1 (C-2′), 21.0 (C-3′). EIMS m/z (rel. int.): 288 [M+] (40), 273 (100), 258 (20). Stenocarpin isobutyrate (2) 1 H NMR (CDCl3, 400 MHz): δ 7.89 (1H, s, H-5), 7.68 (1H, d, J 9.8 Hz, H-4), 6.43 (1H, d, J 9.8 Hz, H-3), 3.99 (3H, s, CH3O-1″), 3.86 (3H, s, CH3O-8), 2.93 (1H, sept, J 7.0 Hz, H-2′), 1.37 (6H, d, J 7.0 Hz, H-3′,4′). 13 C NMR (CDCl3, 50 MHz): δ 174.6 (C-1′), 163.8 (C-1″), 158.9 (C-2), 150.4 (C-8a), 146.6 (C-7), 143.1 (C-4), 140.5 (C-8), 125.2 (C-5), 120.7 (C-6), 117.1 (C-4a), 116.8 (C-3), 61.7 (C1″-CH3O), 52.5 (C8-CH3O), 34.2 (C-2′), 18.8 (C-3′,4′). EIMS m/z (rel. int.): 320 [M + ] (5), 250 (100), 218(58), 190 (50). References [1] [2] [3] [4] [5] [6] [7] [8]
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