Phytochemical investigation of the flowers of Anthemis odontostephana Boiss. var. odontostephana (Asteraceae) resulted in the isolation of a natural cyclohexenone sesquiterpenoid with a bisabolene skeleton, 1-hydroxydelobanone (1), for the first time as a natural product, and a previously reported cyclohexenone derivative, antheminone A (2), along with two known flavonoids, pectolinaringenin (3), and salvigenin (4). The stereochemistry at positions C-4 and C-5 of the cyclohexenone ring of compound 2 was established based on 1H–1H spin-spin coupling constants and ROESY spectra. Compounds 2 and 3 were reported previously as antileishmanial and cytotoxic agents by other authors. The structures of the compounds were elucidated using NMR spectroscopic methods including 1H NMR, 13C NMR, APT, COSY, HSQC, and HMBC, and mass spectrometry.
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References
W. C. Evans, Trease and Evans’ Pharmacognosy, 14 Ed., Saunders, London, 1996.
V. Mozaffarian, A Dictionary of Iranian Plant Names, Farhang Moaser, Tehran, 1996, p. 45.
H. Samsam-Shariat, Collection of Medicinal Plants, Mani, Tehran, 2007.
M. Quarenghi, M. Tereschuk, M. Baigori, and L. Abdala, Fitoterapia, 71, 710 (2000).
I. Uysal, S. Celik, and M. Oldacay, J. App. Sci., 5, 639 (2005).
A. Kurtulmus, T. Fafal, T. Mert, H. Saglam, B. Kivcak, T. Ozturk, B. Demirci, and K. H. C. Baser, Chem. Nat. Compd., 45, 900 (2009).
T. Rossi, M. Melegari, A. Bianchi, A. Albasini, and G. Vampa, Pharmacol. Res. Commun., 20, 71 (1988).
A. Karioti, H. Skaltsa, A. Linden, R. Perozzo, R. Brun, and D. Tasdemir, J. Org. Chem., 72, 8103 (2007).
S. E. Sajjadi, N. Ghassemi, Y. Shokoohinia, and H. Moradi, J. Essent. Oil Bear. Plants, 16, 247 (2013).
N. S. Radulovic, P. D. Blagojevic, B. K. Zlatkovic, and R. M. Palic, J. Chin. Chem. Soc., 56, 642 (2010).
G. Asghari, Res. Pharm. Sci., 7, S800 (2012).
F. Collu, L. Bonsignore, M. Casu, C. Floris, J. Gertsch, and F. Cottiglia, Bioorg. Med. Chem. Lett., 18, 1559 (2008).
K. Takeda, K. Sakurawi, and H. Ishii, Tetrahedron, 27, 6049 (1971).
Acknowledgment
The financial support from Isfahan and Kermanshah Universities of Medical Sciences and Alexander von Humboldt foundation is gratefully acknowledged. We are grateful to Dr. Renate Ellinger and Sybille Lorenz for recording NMR and MS spectra. We are also grateful to Prof. Asghar Mosleh-Arani for identification of plant material.
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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2015, pp. 427–429.
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Shokoohinia, Y., Sajjadi, SE., Jassbi, A.R. et al. Sesquiterpenes and Flavonoids of Anthemis odontostephana var. odontostephana . Chem Nat Compd 51, 491–494 (2015). https://doi.org/10.1007/s10600-015-1322-8
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DOI: https://doi.org/10.1007/s10600-015-1322-8