New Quinolinone Alkaloids from Chestnut (Castanea crenata Sieb) Honey

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 13, 2015, Pages 3587-3592

  Cho, Jeong Yong ^a   Bae, Sun Hee ^a   Kim, Hye Kyung ^b   Lee, Myeong Lyeol ^b   Choi, Yong Soo ^b   Jin, Byung Rae ^c   Lee, Hyoung Jae ^a   Jeong, Hang Yeon ^a   Lee, Yu Geon ^a   Moon, Jae Hak ^a  

^a Chonnam National University   (South Korea)

^b National Institute of Animal Science   (South Korea)

^c Dong A University   (South Korea)

Author keywords

alkaloid; Castanea crenata; chestnut honey; kynurenic acid; quinolinone

Indexed keywords

ALKALOIDS; CHEMICAL COMPOUNDS; ELECTROSPRAY IONIZATION; FOOD PRODUCTS; MASS SPECTROMETRY; METABOLITES; NITROGEN COMPOUNDS;

CASTANEA CRENATA; CHESTNUT HONEY; ELECTROSPRAY IONIZATION MASS SPECTROSCOPY; EXTERNAL STANDARDS; ISOLATED COMPOUNDS; MULTIPLE REACTION MONITORING; QUINAZOLINES; QUINOLINONE;

FRUITS;

CASTANEA CRENATA;

ALKALOID; QUINOLONE DERIVATIVE;

ANALYSIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FAGACEAE; HONEY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKALOIDS; FAGACEAE; HONEY; MAGNETIC RESONANCE SPECTROSCOPY; QUINOLONES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84926512998     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b01027     Document Type: Article

References (24)

1. Schievano, E.; Moelato, E.; Fachin, C.; Mammi, S. Characterization of markers of botanical origin and other compounds extracted from unifloral honeys J. Agric. Food Chem. 2013, 61, 1747 - 1755
2. Gharzouli, K.; Amira, S.; Gharzouli, A.; Khennouf, S. Gastroprotective effects of honey and glucose-fructose-sucrose-maltose mixture against ethanol-, indomethacin-, and acidified aspirin-induced lesions in the rat Exp. Toxicol. Pathol. 2002, 54, 217 - 221
3. Kassim, M.; Achoui, M.; Mustafa, M. R.; Mohd, M. A.; Yusoff, K. M. Ellagic acid, phenolic acids, and flavonoids in Malaysian honey extracts demonstrate in vitro anti-inflammatory activity Nutr. Res. (N.Y.) 2010, 30, 650 - 659
4. Al-Wailli, N. S. Natural honey lowers plasma glucose, C-reactive protein, homocysteine, and blood lipids in healthy, diabetic, and hyperlipidemic subjects: Comparison with dextrose and sucrose J. Med. Food 2004, 7, 100 - 107
5. Koc, A. N.; Silici, S.; Kasap, F.; Hormet-Oz, H. T.; Mavus-Buldu, H.; Ercal, B. D. Antifungal activity of the honey bee products against Candida spp. and Trichosporon spp J. Med. Food 2011, 14, 128 - 134
6. Othman, N. H. Honey and cancer: Substainable inverse relationship particularly for developing nations-A review J. Evidence-Based Complementary Altern. Med. 2012, 2012 410406
7. Erejuwa, O. O.; Sulaiman, S. A.; Ab Wahab, M. S. Honey: A novel antioxidant Molecules 2012, 17, 4400 - 4423
8. Ball, D. W. The chemical composition of honey J. Chem. Educ. 2007, 84, 1643 - 1646
9. Beretta, G.; Caneva, E.; Facino, R. M. Kynurenic acid in honey from arboreal plants: MS and NMR evidence Planta Med. 2007, 73, 1592 - 1595
10. Beretta, G.; Caneva, E.; Regazzoni, L.; Bakhtyari, N. G.; Facino, R. M. A solid-phase extraction procedure coupled to 1H NMR, with chemometric analysis, to seek reliable markers of the botanical origin of honey Anal. Chim. Acta 2008, 620, 176 - 182
11. Beretta, G.; Artali, R.; Caneva, E.; Orlandini, S.; Centini, M.; Facino, R. M. Quinoline alkaloids in honey: Further analytical (HPLC-DAD-ESI-MS, multidimensional diffusion-ordered NMR spectroscopy), theoretical, and chemometric studies J. Pharm. Biomed. Anal. 2009, 50, 432 - 439
12. Beretta, G.; Vistoli, G.; Caneva, E.; Anselmi, C.; Facino, R. M. Structure elucidation and NMR assignments of two new pyrrolidinyl quinolone alkaloids from chestnut Magn. Reson. Chem. 2009, 47, 456 - 459
13. Gasic, U.; Keckes, S.; Dabic, D.; Trifkovic, J.; Milojkovic-Opsenica, D.; Natic, M.; Tesic, Z. Phenolic profile and antioxidant activity of Serbian polyfloral honeys Food Chem. 2014, 145, 599 - 607
14. Alissandrakis, E.; Kibaris, A. C.; Tarantilis, P. A.; Harizanis, P. C.; Polissiou, M. Flavour compounds of Greek cotton honey J. Sci. Food Agric. 2005, 85, 1444 - 1452
15. Jerković, I.; Marijanović, Z.; Kezić, J.; Gugić, M. Headspace, volatile, and semi-volatile organic compounds diversity and radical scavenging activity of ultrasonic solvent extracts from Amorpha fruticosa honey samples Molecules 2009, 14, 2717 - 2728
16. Stephens, J. M.; Schlothauer, R. C.; Morris, B. D.; Yang, D.; Fearnley, L.; Greenwood, D. R.; Loomes, K. M. Phenolic compounds and methylglyoxal in some New Zealand manuka and kanuka honeys Food Chem. 2010, 120, 78 - 86
17. Tuberoso, C. I. G.; Bifulco, E.; Caboni, P.; Cottiglia, F.; Cabras, P.; Floris, I. Floral markers of strawberry tree (Arbutus unedo L.) honey J. Agric. Food Chem. 2010, 58, 384 - 389
18. Azimvand, J. Synthesis of novel 1,2,3,5-tetrahydropyrrole[2,1-b]quinazoline-5-one analogs by using lithiation-intramolecular electrophilic reaction J. Chem. Pharm. Res. 2012, 4, 3924 - 3928
19. Arya, V. P.; Dave, K. G.; Khadse, V. G.; Shenoy, S. J. Synthesis of new heterocycles: Part XXI. Synthesis of some quinazolones Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1976, 14B, 879 - 882
20. Eun, S. M. Synthesis of quinazolin-4-one derivatives from 2-aminobenzamide. II. Reaction with γ-lactone and diketones Yakhak Hoechi 1986, 30, 203 - 207
21. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids Nat. Prod. Rep. 2008, 25, 166 - 187
22. Marella, A.; Tanwar, O. P.; Saha, R.; Ali, M. R.; Srivastava, S.; Akhter, M.; Shaquiquzzaman, M.; Alam, M. M. Quinoline: A versatile heterocyclic Saudi Pharm. J. 2013, 21, 1 - 12
23. Souto, A. L.; Tavares, J. F.; da Silva, M. S.; Diniz, M. F. F. M.; de Athayde-Filho, P. F.; Filho, J. M. B. Anti-inflammatory activity of alkaloids: An update from 2000 to 2010 Molecules 2011, 16, 8515 - 8534
24. Stone, T. W. Development and therapeutic potential of kyrurenic acid and kynurenine derivatives from neuroprotection Trends Pharmacol. Sci. 2000, 21, 149 - 154