Browse > Article
http://dx.doi.org/10.7783/KJMCS.2019.27.6.419

Purification and Identification of Antioxidant Compounds from Dolichos lablab L. Seeds  

Kwon, Nam Woo (Department of Industrial Plant Science & Technology, Chungbuk National University)
Kim, Jae Yeon (Department of Industrial Plant Science & Technology, Chungbuk National University)
Cho, Yong Beom (Department of Industrial Plant Science & Technology, Chungbuk National University)
Hwang, Bang Yeon (Department of Pharmacy, Chungbuk National University)
Kim, Jun Gu (Department of Pharmacy, Chungbuk National University)
Woo, Sun Hee (Department of Crop Science, Chungbuk National University)
Lee, Moon Soon (Department of Industrial Plant Science & Technology, Chungbuk National University)
Publication Information
Korean Journal of Medicinal Crop Science / v.27, no.6, 2019 , pp. 419-426 More about this Journal
Abstract
Background: This study aimed to identify antioxidant compounds from the seeds of Dolichos lablab L. by bioassay-guided isolation and recrystallization. Methods and Results: The water layer of D. lablab L. seed extract inhibits intracellular reactive oxygen species (ROS) expressing the 2',7'-dichlorofluorescein diacetate (DCF-DA), Cu/Zn superoxide dismutase (SOD) and catalase genes, as determined by quantitative real-time PCR (qRT-PCR). Two compounds were purified from the water layer of the seeds of D. lablab L. using column chromatography and prep-high performance liquid chromatography (HPLC). Using nuclear magnetic resonance (NMR) and electrospray Ionization mass spectrometry (ESI-MS), their chemical structures were identified as 5-[(2-acetyl-2,3-dihydro-1H-indazol-1-yl)carbonyl]-4,5-dihydro-3H-furan-2-one (C14H14N2O4) and stachyose. Conclusions: Two active antioxidant compounds were purified from the seed extract of D. lablab L. seed extract and the structures of these compounds were identified as C14H14O4N2 and stachyose.
Keywords
Dolichos lablab L.; Chemical Structures; Reactive Oxygen Species Inhibitory Effect; Seed Extract; $C_{14}H_{14}O_4N_2$; Stachyose;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Al-Snafi AE. (2017). The pharmacology and medical importance of Dolichos lablab(Lablab purpureus): A review. IOSR Journal of Pharmacy. 7:22-30.   DOI
2 Bedard K and Krause KH. (2007). The NOX family of ROSgenerating NADPH oxidases: Physiology and pathophysiology. Physiological Reviews. 87:245-313.   DOI
3 Brzozowski T, Konturek PC, Konturek SJ, Kwiecien S, Sliwowski Z, Pajdo R, Duda A, Ptak A and Hahn EG. (2003). Implications of reactive oxygen species and cytokines in gastroprotection against stress-induced gastric damage by nitric oxide releasing aspirin. International Journal of Colorectal Disease. 18:320-329.   DOI
4 Cerecetto H, Gerpe A, Gonzalez M, Aran VJ and de Ocariz CO. (2005). Pharmacological properties of indazole derivatives: Recent developments. Mini-Reviews in Medicinal Chemistry. 5:869-878.   DOI
5 Im AR, Kim YH, Lee HW and Song KH. (2016). Water extract of Dolichos lablab attenuates hepatic lipid accumulation in a cellular nonalcoholic fatty liver disease model. Journal of Medicinal Food. 19:495-503.   DOI
6 Gaikwad DD, Chapolikar AD, Devkate CG, Warad KD, Tayade AP, Pawar RP and Domb AJ. (2015). Synthesis of indazole motifs and their medicinal importance: An overview. European Journal of Medicinal Chemistry. 90:707-731.   DOI
7 Guzik TJ, Korbut R and Adamek-Guzik T. (2003). Nitric oxide and superoxide in inflammation. Journal of Physiology and Pharmacology. 54:469-487.
8 Huang G, Mao J, Ji Z and Ailati A. (2015). Stachyose-induced apoptosis of caco-2 cells via the caspase-dependent mitochondrial pathway. Food and Function. 6.3:765-771.   DOI
9 Kante K and Reddy CS. (2013). Anti diabetic activity of Dolichos lablab(seeds) in streptozotocin-nicotinamide induced diabetic rats. Hygeia Journal for Drugs and Medicines. 5:32-40.
10 Michiels C, Raes M, Toussaint O and Remacle J. (1994). Importance of Se-glutathione peroxidase, catalase, and Cu/Zn-SOD for cell survival against oxidative stress. Free radical Biology and Medicine. 17:235-248.   DOI
11 Rahman A, Malik S, Hasan SS, Choudhary MI, Ni CZ and Clardy J. (1995). Nigellidine: A new indazole alkaloid from the seeds of Nigella sativa. Tetrahedron Letters. 36:1993-1996.   DOI
12 Nishizawa-Yokoi A, Yabuta Y and Shigeoka S. (2008). The contribution of carbohydrates including raffinose family oligosaccharides and sugar alcohol to protection of plant cells from oxidative damage. Plant Signaling and Behavior. 3:1016-1018.   DOI
13 Niu XF, Smith CW and Kubes P. (1994). Intracellular oxidative stress induced by nitric oxide synthesis inhibition increases endothelial cell adhesion to neutrophils. Circulation Research. 74:1133-1140.   DOI
14 Osman MA. (2007). Effect of different processing methods, on nutrient composition, antinutrional factors, and in vitro protein digestibility of Dolichos lablab bean[Lablab purpuresus (L) Sweet]. Pakistan Journal of Nutrition. 6:299-303.   DOI
15 Peterbauer T and Richter A. (2001). Biochemistry and physiology of raffinose family oligosaccharides and galactosyl cyclitols in seeds. Seed Science Research. 11:185-197.
16 Priya S and Jenifer S. (2014). Antibacterial activity of leaf and flower extract of Lablab purpureus against clinical isolates of Staphylococcus aureus. Research and Reviews: A Journal of Drug Design and Discovery. 1:5-7.
17 Ramakrishna V, Jhansi Rani P and Pao RR. (2007). Hypocholesterolemic effect of diet supplemented with Indian bean (Dolichos lablab L. var lignosus) seeds. Nutrition and Food Science. 37:452-456.   DOI
18 Takeuchi A, Hori M, Sato S, Ban HS, Kuchimaru T, Kizaka-Kondoh S, Yamori T and Nakamura H. (2012). Synthesis and biological activity of furanylindazoles as inhibitors of hypoxia inducible factor(HIF)-1 transcriptional activity. Medicinal Chemistry. Communication. 3:1455-1461.   DOI
19 Salvemini D, Ischiropoulos H and Cuzzocrea S. (2003). Roles of nitric oxide and superoxide in inflammation. In Winyard PG and Willoughby DA (ed.). In Inflammation Protocols. Methods in Molecular Biology. vol 225. Humana Press. Totowa, NJ, USA. p.291-303.
20 Stoyanova S, Geuns J, Hideg E and Van Den Ende W. (2011). The food additives inulin and stevioside counteract oxidative stress. International Journal of Food Sciences and Nutrition. 62:207-214.   DOI
21 Tiidus PM. (1998). Radical species in inflammation and overtraining. Canadian Journal of Physiology and Pharmacology. 76:533-538.   DOI
22 Warleta F, Quesada CS, Campos M, Allouche Y, Beltran G and Gaforio JJ. (2011). Hydroxytyrosol protects against oxidative DNA damage in human breast cells. Nutrients. 3:839-857.   DOI
23 Ye XY, Wang HX and Ng TB. (2000). Dolichin, a new chitinaselike antifungal protein isolated from field beans(Dolichos lablab). Biochemical and Biophysical Research Communications. 269:155-159.   DOI