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DOI: 10.1055/a-1939-7473
Phytochemical Characterization of Phitosia crocifolia, a Monotypic Representative of Greek Flora
Supported by: Hellenic Foundation for Research and Innovation 16274
Abstract
Within the large Compositae family, Phitosia is considered a monotypic genus of the Greek flora, with its only species P. crocifolia (Boiss. & Heldr.) Kamari & Greuter growing wild with limited distribution, exclusively on the mountains Taigetos and Parnonas in Peloponnese. P. crocifoliaʼs chemical profile was obtained, herein, for the first time and led to the isolation of 20 compounds, thirteen of which were characterized as sesquiterpene lactones and the rest mainly as phenolic derivatives. The isolates 1–3, 5 – 7 and 11 – 13 represent new chemical structures. Compounds 2 and 3 especially are substituted with a pentose moiety, a rare phenomenon in sesquiterpene lactone backbones. A series of spectrometric and spectroscopic techniques were used to elucidate their structures. The relative configurations of the unreported compounds were established via extensive analysis of NMR spectroscopic and HRESIMS data, assisted by CD spectroscopic measurements. Throughout the entire isolation procedure, selected fractions rich in sesquiterpene lactones were tested against HeLa cancerous cell line for their cytotoxic effects with the lowest IC50 values being 18.84 µg/mL. Accordingly, among the tested isolates, compounds 5 and 9 exerted IC50 values of 13.5 µM and 11.4 µM, respectively.
Key words
Phitosia crocifolia - Cichorieae - Compositae - sesquiterpene lactones - phenolics - NMR - HeLaSupporting Information
- Supporting Information
S1 – S46: NMR spectra of new compounds; S49: CD of new compounds; S50 – S51: Key COSY, NOESY and HMBC correlations of new compounds; S52: Cell survival curves on HeLa for fractions and compounds determined by MTT assay.
Publication History
Received: 25 March 2022
Accepted after revision: 06 September 2022
Article published online:
10 January 2023
© 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG
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References
- 1 Kougioumoutzis K, Kokkoris IP, Panitsa M, Kallimanis A, Strid A, Dimopoulos P. Plant endemism centres and biodiversity hotspots in Greece. Biology (Basel) 2021; 10: 72 DOI: 10.3390/biology10020072.
- 2 Dimopoulos P, Raus T, Bergmeier E, Constantinidis T, Iatrou G, Kokkini S, Strid A, Tzanoudakis D. Vascular plants of Greece: An annotated checklist. Willdenowia 2016; 46: 301-347 DOI: 10.3372/wi.46.46303.
- 3 Phitos D, Strid A, Snogerup S, Greuter W. The Red Data Book of Rare and threatened Plants of Greece. Athens: WWF Hellas; 1995
- 4 Babcock EB. The Genus Crepis. Part 2. Systematic treatment. Berkeley, Los Angeles: University California Publication Botany 1947; 22: 199-1030
- 5 Constantinidis T, Kamari G. (eds) The red data book of rare and threatened plants of Greece, vol. 1 (A – D) & vol.2 (E – Z), (in Greek). Patras: Hellenic Botanical Society; 2009
- 6 Kamari G, Greuter W. Phitosia, a new genus for Crepis crocifolia (Compositae, Cichorieae), a local endemic of Mount Taigetos (Greece). Bot Chron 2000; 13: 11-36
- 7 Kamari G, Kyriakopoulos C, Kofinas G. New finding of Phitosia crocifolia (Compositae) in E Peloponnisos. Flora Mediterranea 2010; 20: 235-238
- 8 Zidorn C, Ellmerer-Müller EP, Stuppner H. Eudesmanolides and inositol derivatives from Taraxacum linearisquameum . Phytochemistry 1999; 51: 991-994 DOI: 10.1016/S0031-9422(99)00163-6.
- 9 Dang T, Zheng G, Zhang Q, Jin P, Zhang H, Su L, Qin D, Yao G. Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities. Fitoterapia 2019; 136: 104170 DOI: 10.1016/j.fitote.2019.104170.
- 10 Gören N. Eudesmane-type sesquiterpenes from Tanacetum praeteritum subsp. praeteritum . Phytochemistry 1996; 42: 747-749 DOI: 10.1016/0031-9422(95)00933-7.
- 11 Kijjoa A, Vieira LMM, Cardoso JM, Werner H. A eudesmanolide from Picris spinifera . Phytochemistry 1992; 31: 3635-3636 DOI: 10.1016/0031-9422(92)83744-J.
- 12 Costa FLP, Fingolo CE, Boylan F, Amorim MBD. Isolation, identification, relative configuration and conformational analysis of loliolide by GIAO-HDFT 1H and 13C NMR chemical shifts calculations. Quantum Matter 2016; 5: 675-679 DOI: 10.1166/qm.2016.1362.
- 13 Hiraga Y, Taino K, Kurokawa M, Tagaki R, Ohkata K. (−)-Loliolide and other germination inhibitory active constituents in Equisetum Arvense . Nat Prod Lett 1997; 10: 181-186 DOI: 10.1080/10575639708041192.
- 14 Wang Z, Peng S, Peng M, Wang C. Isolation of polyphenol compounds from olive waste and inhibition of their derivatives for α-glucosidase and α-amylase. Nat Prod Res 2019; 34: 2398-2402 DOI: 10.1080/14786419.2018.1538217.
- 15 Warashina T, Ishino M, Miyase T, Ueno A. Sesquiterpene glycosides from Ixeris debilis and Ixeris repens . Phytochemistry 1990; 29: 3217-3224 DOI: 10.1016/0031-9422(90)80188-M.
- 16 Kisiel W, Michalska K. A new coumarin glucoside ester from Cichorium intybus . Fitoterapia 2002; 73: 544-546 DOI: 10.1016/S0367-326X(02)00172-7.
- 17 Moussouni S, Karakousi CV, Tsatalas P, Lazari D, Kokkalou E. Biological studies with phytochemical analysis of Cornus mas unripe fruits. Chem Nat Compd 2020; 56: 141-144 DOI: 10.1007/s10600-020-02966-8.
- 18 Hong SS, Choi CW, Choi YH, Oh JS. Coixlachryside A: A new lignan glycoside from the roots of Coix lachryma-jobi L. var. ma-yuen Stapf. Phytochem Lett 2016; 17: 152-157 DOI: 10.1016/j.phytol.2016.07.004.
- 19 Jung HA, Park JC, Chung YH, Kim J, Choi JS. Antioxidant flavonoids and chlorogenic acid from the leaves of Eriobotrya japonica . Arch Pharm Res 1999; 22: 213-218 DOI: 10.1007/BF02976549.
- 20 Zidorn C. Bioprospecting of plant natural products in Schleswig-Holstein (Germany) I: chemodiversity of the Cichorieae tribe (Compositae) in Schleswig-Holstein. Phytochem Rev 2019; 18: 1223-1253 DOI: 10.1007/s11101-019-09609-z.
- 21 White EH, Winter REK. Natural products from Achillea lanulosa . Tetrahedron Lett 1963; 4: 137-140 DOI: 10.1016/S0040-4039(01)90593-3.
- 22 Agrawal PK. NMR Spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 1992; 31: 3307-3330 DOI: 10.1016/0031-9422(92)83678-R.
- 23 Michalska K, Żylewski M, Kisiel W. Structure elucidation and complete NMR spectral assignments of two new sesquiterpene lactone xylosides from Lactuca triangulate . Magn Reson Chem 2008; 46: 1185-1187 DOI: 10.1002/mrc.2323.
- 24 Julianti E, Jang KH, Lee S, Lee D, Mar W, Oh KB, Shin J. Sesquiterpenes from the leaves of Laurus nobilis L. Phytochemistry 2012; 80: 70-76 DOI: 10.1016/j.phytochem.2012.05.013.
- 25 Wang XX, Gao X, Jia ZJ. Sesquiterpenoids from Lactuca tatarica . Fitoterapia 2010; 81: 42-44 DOI: 10.1016/j.fitote.2009.07.001.
- 26 Miyase T, Fukushima S. Studies on sesquiterpene glycosides from Sonchus oleraceus L. Chem Pharm Bull 1987; 35: 2869-2874 DOI: 10.1248/cpb.35.2869.
- 27 Boik J. Natural Compounds in Cancer Therapy. Princeton, MN, USA: Oregon Medical Press; 2001
- 28 Heilmann J, Wasescha MR, Schmidt TJ. The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells. Bioorg Med Chem 2001; 9: 2189-2194 DOI: 10.1016/s0968-0896(01)00131-6.