Characterisation of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis

被引:131
作者
Lee, Jin Hwan [1 ]
Kang, Nam Suk [1 ]
Shin, Sang-Ouk [1 ]
Shin, Seong-Hyu [1 ]
Lim, Sea-Gyu [1 ]
Suh, Duck-Yong [1 ]
Baek, In-Youl [1 ]
Park, Keum-Yong [1 ]
Ha, Tae Joung [1 ]
机构
[1] RDA, Natl Inst Crop Sci, Yeongnarn Agr Res Inst, Milyang 627803, South Korea
关键词
anthocyanins; Glycine max; NMR; HPLC-ESI/MS; black soybean; CONDENSED PIGMENTS; ALPHA;
D O I
10.1016/j.foodchem.2008.05.056
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The aim of this study was to isolate and identify the anthocyanins in the black seed coated soybean (cv. Cheongja 3, Glycine max (L.) Merr.) using reverse phase C-18 open column chromatography and high-performance liquid chromatography (HPLC) with diode array detection and electro spray ionization/mass spectrometry (DAD-ESI/MS) analysis, respectively. Anthocyanins were extracted from the coat of black soybeans with 1% TFA in methanol, isolated by RP-C-18 column chromatography, and their structures elucidated by ID and 2D NMR spectroscopy. The isolated anthocyanins were characterised as delphinidin-3-O-glucoside (3), cyanidin-3-O-glucoside (5), petunidin-3-O-glucoside (6), pelargonidin-3-O-glucoside (7) and cyanidin (9). Furthermore, four minor anthocyanins were detected and identified as catechin-cyanidin-3-O-glucoside (1), delphinidin-3-O-galactoside (2), cyanidin-3-O-galactoside (4), and peonidin-3-O-glucoside (8) based on the fragmentation patterns of HPLC-DAD-ESI/MS analysis. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:226 / 231
页数:6
相关论文
共 31 条
[1]   In vitro anticancer activity of fruit extracts from Vaccinium species [J].
Bomser, J ;
Madhavi, DL ;
Singletary, K ;
Smith, MAL .
PLANTA MEDICA, 1996, 62 (03) :212-216
[2]   Isolation and determination of anthocyanins in seed coats of black soybean (Glycine max (L.) merr.) [J].
Choung, MG ;
Baek, IY ;
Kang, ST ;
Han, WY ;
Shin, DC ;
Moon, HP ;
Kang, KH .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (12) :5848-5851
[3]  
Clifford MN, 2000, J SCI FOOD AGR, V80, P1118, DOI [10.1002/(SICI)1097-0010(20000515)80:7<1118::AID-JSFA570>3.0.CO
[4]  
2-9, 10.1002/(SICI)1097-0010(20000515)80:7<1063::AID-JSFA605>3.0.CO
[5]  
2-Q]
[6]  
COLANTUONI A, 1991, ARZNEIMITTELFORSCH, V41-2, P905
[7]   Dimeric anthocyanins from strawberry (Fragaria ananassa) consisting of pelargonidin 3-glucoside covalently linked to four flavan-3-ols [J].
Fossen, T ;
Rayyan, S ;
Andersen, OM .
PHYTOCHEMISTRY, 2004, 65 (10) :1421-1428
[8]   Anthocyanins from maize (Zea mays) and reed canarygrass (Phalaris arundinacea) [J].
Fossen, T ;
Slimestad, R ;
Andersen, OM .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (05) :2318-2321
[9]   Flavanol-anthocyanin condensed pigments in plant extracts [J].
González-Paramás, AM ;
da Silva, FL ;
Martin-López, P ;
Macz-Pop, G ;
González-Manzano, S ;
Alcalde-Eon, C ;
Pérez-Alonso, JJ ;
Escribano-Bailón, MT ;
Rivas-Gonzalo, JC ;
Santos-Buelga, C .
FOOD CHEMISTRY, 2006, 94 (03) :428-436
[10]   Potential mechanisms of cancer chemoprevention by anthocyanins [J].
Hou, DX .
CURRENT MOLECULAR MEDICINE, 2003, 3 (02) :149-159