Iridoids and flavonoids of four Siberian gentians: Chemical profile and gastric stimulatory effect

Molecules

Volumn 20, Issue 10, 2015, Pages 19172-19188

  Olennikov, Daniil N ^a   Kashchenko, Nina I ^a   Chirikova, Nadezhda K ^b   Tankhaeva, Larisa M ^a  

^a INSTITUTE OF GENERAL AND EXPERIMENTAL BIOLOGY   (Russian Federation)

^b NORTH EASTERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

Flavonoids; Gastric secretion stimulation; Gentiana algida; Gentiana decumbens; Gentiana macrophylla; Gentiana triflora; HPLC; Iridoids

Indexed keywords

FLAVONOID; IRIDOID; PLANT EXTRACT;

ANIMAL; CHEMISTRY; DRUG EFFECTS; ELECTROSPRAY MASS SPECTROMETRY; FLOWER; GASTRIC MUCOSA; GENTIAN; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MALE; PLANT ROOT; PRECLINICAL STUDY; RUSSIAN FEDERATION; SECRETION (PROCESS); SPRAGUE DAWLEY RAT; STOMACH;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG EVALUATION, PRECLINICAL; FLAVONOIDS; FLOWERS; GASTRIC MUCOSA; GENTIANA; IRIDOIDS; MALE; PLANT EXTRACTS; PLANT ROOTS; RATS, SPRAGUE-DAWLEY; SIBERIA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STOMACH;

EID: 84947562662     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules201019172     Document Type: Article

References (44)

1. Anonymous. Buryats; Abaeva, L.L., Zhukovskaya, N.L., Eds.; Nauka: Moscow, Russia, 2004; p. 633.
2. Anonymous. Traditions of the Buryat Cuisine; Mikhailova, V.T., Ed.; Printhouse L.T.: Ulan-Ude, Bria, 2010; p. 93.
3. Makarov, A.A. Plant Remedies of the Traditional Yakutian Medicine; Yakutian Scientific Center: Yakutsk, Russia, 1974; p. 64.
4. Anonymous. Traditions and Innovations in Life and Culture of the Siberian Peoples; Rusakova, L.M., Ed.; SD RAS: Novosibirsk, Russia, 1983; p. 138.
5. Tankhaeva, L.M.; Nikolaeva, G.G.; Glyzin, V.I.; Pinchuk, I.N. γ-Pyrone derivatives from Halenia corniculata. Chem. Nat. Compd. 1984, 20, 747.
6. Purev, O.; Odontyuya, G.; Oyun, H.; Tankhaeva, L.M.; Nasreen, A. Atta-ur-ranman. Xanthones of Halenia corniculata. Nat. Prod. Lett. 1995, 5, 261-268.
7. Mikhailova, T.M.; Shul'ts, E.E.; Komarova, N.I.; Tankhaeva, L.M.; Nikolaeva, G.G.; Sambueva, Z.G.; Nikolaev, S.M.; Bodoev, N.V.; Tolstikov, G.A. Xanthones from Halenia corniculata. Synthesis and cholagogic action of certain derivatives. Chem. Nat. Compd. 2004, 40, 451-456.
8. Mikhailova, T.M.; Olennikov, D.N.; Tankhaeva, L.M.; Nikolaeva, G.G. Xanthones from Halenia corniculata. 2. Quantitative determination of total γ-pyrone content in the aerial part. Chem. Nat. Compd. 2005, 41, 303-306.
9. Nikolaev, S.M.; Sambueva, Z.G.; Tsyrenzhapov, A.V.; Nikolaeva, G.G.; Tankhaeva, L.M.; Glyzin, V.I.; Dargaeva, T.D. Comparative choleretic properties of natural xanthone compounds from Gentianopsis barbata. Eksp. Klin. Farmakol. 2003, 66, 29-31.
10. Olennikov, D.N. Chemical investigation of Anagallidium dichotomum and anticholinesterase activity of its constituents. Chem. Nat. Compd. 2013, 49, 1137-1139.
11. Hostettmann-Kaldas, M.; Hostettmann, K.; Sticher, O. Xanthones, flavones and secoiridoids of American Gentiana species. Phytochemistry 1981, 20, 443-446.
12. Tan, R.X.; Wolfender, J.-L.; Ma, W.G.; Zhang, L.X.; Hostettmann, K. Secoiridoids and antifungal aromatic acids from Gentiana algida. Phytochemistry 1996, 41, 111-116.
13. Tan, R.X.; Hu, J.; Kong, L.D.; Wolfender, J.-L.; Hostettmann, K. Two new secoiridoid glucosides Gentiana algida. Planta Med. 1997, 63, 567-569.
14. Yang, A.M.; Li, H.; Liu, J.L.; Han, H.; Sun, J. Chemical constituents of Gentiana algida. Chem. Nat. Compd. 2013, 49, 755-756.
15. Yang, A.M.; Shi, X.L.; Han, H.; Men, Y.; Wu, R. Flavonoids and cytotoxic activity of Gentiana algida Pall. Adv. Mater. Res. 2014, 852, 278-281.
16. Cao, X.-Y.; Wang, Z.-Z. Simultaneous determination of four iridoids and secoiridoid glycosides and comparative analysis of Radix Gentianae Macrophyllae and their related substituents by HPLC. Phytochem. Anal. 2010, 21, 348-354.
17. Tan, R.X.; Wolfender, J.-L.; Zhang, L.X.; Ma, W.G.; Fuzzati, N.; Marston, A.; Hostettmann, K. Acyl secoiridoids and antifungal constituents from Gentiana macrophylla. Phytochemistry 1996, 42, 1305-1313.
18. Jia, N.; Li, Y.; Wu, Y.; Xi, M.; Hur, G.; Zhang, X.; Cui, J.; Sun, W.; Wen, A. Comparison of the anti-inflammatory and analgetic effects of Gentiana macrophylla pall. and Gentiana straminea Maxim., and identification of their active constituents. J. Ethnopharmacol. 2012, 144, 638-645.
19. Wang, S.; Xu, Y.; Jiang, W.; Zhang, Y. Isolation and identification of constituents with activity of inhibiting nitric oxide production in raw 264.7 macrophages from Gentiana triflora. Planta Med. 2013, 79, 680-686.
20. Sasaki, N.; Nishizaki, Y.; Yamada, E.; Tatsuzawa, F.; Nakatsuka, T.; Takahashi, H.; Nishihara, M. Identification of the glucosyltransferase that mediates direct flavone C-glucosylation in Gentiana triflora. FEBS Lett. 2015, 589, 182-187.
21. Yang, J.L.; Liu, L.L.; Shi, Y.P. Phytochemicals and biological activities of Gentiana species. Nat. Prod. Commun. 2010, 5, 649-664.
22. Jensen, S.R.; Schripsema, J. Chemotaxonomy and pharmacology of Gentianaceae. In Gentianaceae: Systematics and Natural History; Struwe, L., Albert, V.A., Eds.; Cambridge University Press: Cambridge, UK, 2002; pp. 573-631.
23. Yeung, M.F.; Che, C.T. A review on presence of oleanolic acid in natural products. Nat. Prod. Med. 2009, 2, 77-290.
24. Liu, B.; Yue, M.-E.; Yang, S.-R.; Shi, Y.-P. Determination of phenolic glycosides in Gentiana piasezkii by capillary zone electrophoresis. Chromatographia 2005, 62, 643-647.
25. Burret, F.; Chulia, A.J.; Debelmas, A.M.; Hostettmann, K. Presence of isoscoparine, isoscoparine-7-O-glucoside and saponarine in Gentiana pneumonanthe L. Planta Med. 1978, 34, 176-179.
26. Bergeron, C.; Marston, A.; Gauthier, R.; Hostettmann, K. Iridoids and secoiridoids from Gentiana linearis. Phytochemistry 1997, 44, 633-637.
27. Xu, M.; Wang, D.; Zhang, Y.J.; Yang, C.R. Iridoidal glucosides from Gentiana rhodantha. J. Asian Nat. Prod. Res. 2008, 10, 491-498.
28. Wang, Y.-M.; Xu, M.; Wang, D.; Zhu, H.-T.; Yang, C.-R.; Zhang, Y.-J. Review on "Long-Dan", one of the traditional Chinese medicinal herbs reordered in Chinese Pharmacopoeia. Nat. Prod. Bioprospect. 2012, 2, 1-10.
29. Goetz, M.; Jacot-Guillarmond, A. Phytochemistry of genus Gentiana. XXII. Identification of new O-glucosides of mangiferin in Gentiana asclepiadea L. Helv. Chim. Acta 1977, 60, 2104-2106.
30. Wang, Y.S. Pharmacology and Applications of Chinese Materia Medica; People's Health Publisher: Beijing, China, 1983; pp. 295-299.
31. Abdallah, I.Z.A.; Khattab, H.A.H.; Heeba, G.H. Gastroprotective effect of Cordia myxa L. fruit extract against indomethacin-induced gastric ulceration in rats. Life Sci. J. 2011, 8, 433-445.
32. Olennikov, D.N.; Tankhaeva, L.M. Biologically active substances from Cacalia hastata leaves. 5. Coumarins and triterpenes. Chem. Nat. Comp. 2005, 41, 600-601.
33. Dinda, B.; Debnath, S.; Harigaya, Y. Naturally occurring iridoids. A review, part I. Chem. Pharm. Bull. 2007, 55, 159-222.
34. El-Naggar, L.J.; Beal, J.L. Iridoids. A review. J. Nat. Prod. 1980, 43, 649-707.
35. Popovici, G.; Weissenböck, G.; Bouillant, M.-L.; Dellamonica, G.; Chopin, J. Isolation and characterization of flavonoids from Avena sativa L. Z. Pflanzenphysiol. 1977, 85, 103-115.
36. Hostettmann, K.; Bellmann, G.; Tabacchi, R.; Jacot-Guillarmod, A. Contribution á la phytochimie du genre Gentiana. III. Etude des composés flavoniques et xanthiniques dans les feulles fe Gentiana lutea. Helv. Chim. Acta 1973, 56, 3050-3054.
37. Markham, K.R.; Mitchell, K.A. The mis-identification of the major antioxidant flavonoids in young barley (Hordeum vulgare) leaves. Z. Naturforsch. 2003, 58c, 53-56.
38. Peng, J.; Fan, G.; Hong, Z.; Chai, Y.; Wu, Y. Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss by high-speed counter-current chromatography. J. Chrom. A 2005, 1074, 111-115.
39. Shay, H.; Komarov, S.A.; Fels, S.S.; Meranze, D.; Gruenstein, M.; Siplet, H. A simple method for the uniform production of gastric ulceration. Gastroenterology 1945, 5, 43-61.
40. Kurasawa, T.; Chikaraichi, Y.; Naito, A.; Toyoda, Y.; Notsu, Y. Effect of Humulus lupulus on gastric secretion in a rat pylorus-ligated model. Biol. Pharm. Bull. 2005, 28, 353-357.
41. Hara, N.; Hara, Y.; Natsume, Y.; Goto, Y. Gastric hyperacidity and mucosal damage caused by hypothermia correlate with increase in GABA concentrations of the rat brain. Eur. J. Pharmacol. 1991, 194, 77-81.
42. Feldman, M. Gastric secretion, normal and abnormal. In Gastrointestinal and Liver Disease: Pathophysiology/Diagnosis/Management; Feldman, M., Scharschmidt, B.F., Sleisenger, M.H., Eds.; WB Saunders Co: Philadelphia, PA, USA, 1998; pp. 587-603.
43. Sanyal, A.R.; Denath, O.K.; Bhattacharya, S.K.; Gode, K.D. The effect of cyproheptadine on gastric acidity. In Peptic Ulcer; Pfeiffer, C.J., Ed.; Scandinavian University Books: Copenhagen, Denmark, 1971; pp. 312-318.
44. Winzler, R.J. Determination of serum glycoproteins. Meth. Biochem. Anal. 1955, 2, 279-311.