The purpose of this study was to isolate Monascus yellow pigments and to study its chemical structure. Components of Monascus yellow pigments from fermentation broth were isolated, purified and identified by high-performance liquid chromatography (HPLC), mass spectrometry (MS) and Nuclear magnetic resonance (NMR). Two major components showed on HPLC spectrum as two adjacent peaks, namely A and B. Resolution between A and B was 2.51. Then A and B were isolated using preparative HPLC with a few adjustments. High purity of A (98.95%) and B (99.02%) were obtained. Combing data from MS with 1D and 2D NMR analysis, A and B were elucidated as Monascin (C21H26O5, molecular weight 358) and Monaphilone B (C20H28O4, molecular weight 332), respectively. The yellow pigment comes from its α, β-unsaturated ketone structures.
XU Feifei
,
XU Haixiao
,
LIANG Rong
,
ZHONG Fang
. Isolation, purification and evaluation of Monascus yellow pigments from fermentation broth[J]. Food and Fermentation Industries, 2020
, 46(1)
: 91
-98
.
DOI: 10.13995/j.cnki.11-1802/ts.021662
[1] JUZLOVAP,MARTINKOVA L,KREN V. Secondary metabolites of the fungus Monascus: A review[J]. Journal of Industrial Microbiology,1996,16(3): 163-170.
[2] HSU L C,HSU Y W,LIANG Y H,et al. Anti-tumor and anti-inflammatory properties of ankaflavin and monaphilone A from Monascus purpureus NTU 568[J]. Journal of Agricultural and Food Chemistry,2011,59(4): 1 124-1 130.
[3] LEE C L,KUNG Y H,WU C L,et al. Monascin and ankaflavin act as novel hypolipidemic and high-density lipoprotein cholesterol-raising agents in red mold dioscorea[J]. Journal of Agricultural and Food Chemistry,2010,58(16): 9 013-9 019.
[4] LEE C L,HUNG Y P,HSU Y W,et al. Monascin and ankaflavin have more anti-atherosclerosis effect and less side effect involving increasing creatinine phosphokinase activity than Monacolin K under the same dosages[J]. Journal of Agricultural and Food Chemistry,2013,61(1): 143-150.
[5] LEE C L,WEN J Y,HSU Y W,et al. Monascus-fermented yellow pigments monascin and ankaflavin showed antiobesity effect via the suppression of differentiation and lipogenesis in obese rats fed a high-fat diet[J]. Journal of Agricultural and Food Chemistry,2013,61(7): 1 493-1 500.
[6] HSU W H,LEE B H,Lu I J,et al. Ankaflavin and monascin regulate endothelial adhesion molecules and endothelial NO synthase (eNOS) expression induced by tumor necrosis factor-alpha (TNF-alpha) in human umbilical vein endothelial cells (HUVECs)[J]. Journal of Agricultural and Food Chemistry,2012,60(7): 1 666-1 672.
[7] HSU W H,PAN T M. A novel PPARgamma agonist Monascin's potential application in diabetes prevention[J]. Food & Function,2014,5(7): 1 334-1 340.
[8] CHANG Y Y,HSU W H,PAN T M. Monascus secondary metabolites monascin and ankaflavin inhibit activation of RBL-2H3 cells[J]. Journal of Agricultural and Food Chemistry,2015,63(1): 192-199.
[9] HSU W H,PAN T M. Treatment of metabolic syndrome with ankaflavin,a secondary metabolite isolated from the edible fungus Monascus spp.[J]. Applied Microbiology and Biotechnology,2014,98(11): 4 853-4 863.
[10] HSU L C,LIANG Y H,HSU Y W,et al. Anti-inflammatory properties of yellow and orange pigments from Monascus purpureus NTU 568[J]. Journal of Agricultural and Food Chemistry,2013,61(11): 2 796-2 802.
[11] 毛鹏. 红曲黄色素液态发酵技术研究[D].无锡:江南大学,2015.
[12] PATRA P. Monascus secondary metabolites: production and biological activity[J]. Journal of Industrial Microbiology & Biotechnology,2013,40(2): 169-181.
[13] MARIE O L, SANDRINE M. Isolation and structural characterization of two new metabolites from Monascus[J]. Journal of Agricultural and Food Chemistry,2010,58(3): 1 800-1 803.
[14] 杨强,郎天丹,岳建明,等. 红曲黄色素的分离纯化与表征[J]. 食品工业科技,2015,36(16): 308-312.
[15] 夏明,杜琪珍. 高速逆流色谱提取分离红曲色素的研究[J]. 广州食品工业科技,2002(4): 5-6.
[16] 郑允权,李泳宁,王阿万,等. 高速逆流色谱法分离纯化红曲色素组分[J]. 食品科学,2010,31(20): 192-195.
[17] 崔莉,胡晓丹,张德权. HPLC法同时测定红曲色素中的红曲素和安卡红曲黄素[J]. 食品科学,2009,30(8): 163-166.
[18] 李明起. 红曲色素的制备、分离及黄色素结构表征[D].武汉:武汉工业学院,2011.
[19] 王丽峰. 高效液相色谱在中草药质量控制中的应用[D].重庆:西南大学,2009.
[20] 冼燕萍,郭新东,罗海英,等. 固相萃取-超高效液相色谱分离测定洗涤用品中4种荧光增白剂[J]. 色谱,2013,31(2): 162-169.
[21] 黄艳,王璐,毛鹏,等. 红曲液态发酵生产橙、黄色素及其色调研究[J]. 食品工业科技,2014,35(19): 142-145.
[22] BUSABA Y,SOMCHAI K,RAPEEPOL B. Production of yellow pigments in submerged culture of a mutant of Monascus spp.[J]. Journal of Fermentation and Bioengineering,1994,78(3): 223-228.
[23] BUSABA Y,PANIDA T,WORAWAN K,et al. Fermentation and quality of yellow pigments from golden brown rice solid culture by a selected Monascus mutant[J]. Applied Microbiology and Biotechnology,2013,97(20): 8 895-8 902.
[24] HSU Y W,HSU L C,LIANG Y H,et al. Monaphilones A-C,three new antiproliferative azaphilone derivatives from Monascuspurpureus NTU 568[J]. Journal of Agricultural and Food Chemistry,2010,58(14): 8 211-8 216.
[25] 刘约权.现代仪器分析第3版[M].北京:高等教育出版社,2015.