异阿魏酸酰胺类衍生物的合成及其美白活性的研究

doi:10.3969/j.issn.1001-1803.2021.11.010

Abstract

Abstract:

Using isoferulic acid and amino acid ethyl ester hydrochloride as raw materials, 1- （3-dimethylaminopropyl）-3-ethylcarbodiimide hydrochloride （EDC HCl） and 1-hydroxybenzotriazole （HOBt） as catalysts, isoferuloyl-alanine ethyl ester （a）, isoferuloyl-phenylalanine ethyl ester （b）, isoferuloyl-leucine ethyl ester （c）, isoferuloyl-isoleucine ethyl ester （d）, isoferuloyl-valine ethyl ester （e）, isoferuloyl-methionine ethyl ester （f） were synthesized by EDC condensation. The structure of the products was characterized by nuclear magnetic resonance （¹H NMR） and high performance liquid chromatography-mass spectrometry （HPLC-MS）. The whitening activity of ethyl isoferulyl-amino acid was detected by two in vitro non-cellular experiments of scavenging DPPH free radicals and inhibiting tyrosinase activity. It can be seen from the experimental results that the six isoferulyl amino acids have a good ability to scavenge DPPH free radicals, which are higher than that of isoferulic acid. Isoferulyl-alanine ethyl ester has the strongest ability to scavenge DPPH free radicals. Its IC₅₀ value reaches 1.13 mg/mL. It also has a certain inhibitory effect on tyrosinase activity, of which isoferulyl-alanine ethyl ester has the best effect, with the inhibition rate of 95.43%. The results of B16 melanoma cells show that isoferulyl-alanine ethyl ester, isoferulyl-phenylalanine ethyl ester and isoferulyl-methionine ethyl ester have better inhibitory effects on melanin than isoferulic acid at 2 mg/mL mass concentration and its irritation is reduced. The differences in the efficacy of the six products may be due to the different types of side chain amino acids on each substance. In the follow-up investigation, the biological activity of isoferulyl amino acid derivatives can be analyzed to clarify the relationship between the molecular structure of the substance and the physiological activity, and to increase the transdermal absorption effect and safety of the substance in animal experiments.

Key words: isoferulic acid, isoferulic acid ethyl ester, DPPH radical, tyrosinase, B16 melanoma cells

CLC Number:

TQ658

Luo Tianji,Mei Zikun,Song Jingjiu,Zhu Jun. Study on synthesis and whitening activity of isoferic acid amides[J].China Surfactant Detergent & Cosmetics, 2021, 51(11): 1102-1108.

Figures/Tables 5

Tab. 1

Tab. 2

Tab. 3

Tab. 4

Tab. 5

References 15

[1]	Jia Xiushan. Determination of ferulic acid and isoferulic acid in Rhizoma Nanchuan by RP-HPLC[D]. Chongqing: Southwest University, 2010.
[2]	Meeprom A, Sompong W, Chan C, et al. Isoferulic acid, a new anti-glycation agent, inhibits fructose- and glucose-mediated protein glycation in vitro[J]. Molecules, 2013, 18(6): 6439-6454. doi: 10.3390/molecules18066439
[3]	Liu Hongmei. Study on synthesis and hypoglycemic activity of isoferulic acid derivatives[D]. Guangzhou: Guangdong Institute of Pharmacy, 2007.
[4]	Liu I M, Hsu F L, Chen C F, et al. Antihyperglycemic action of isoferulic acid in streptozotocin-induced diabetic rats[J]. British Journal of Pharmacology, 2000, 129(4): 631-636. pmid: 10683186
[5]	Sakai S, Ochiai H, Mantani N, et al. Administration of isoferulic acid improved the survival rate of lethal influenza virus pneumonia in mice[J]. Mediators of Inflammation, 2001, 10(2): 93-96. pmid: 11405556
[6]	Aramsri, Meeprom, Weerachat, et al. Isoferulic acid prevents methylglyoxal-induced protein glycation and DNA damage by free radical scavenging activity[J]. BMC Complementary and Alternative Medicine, 2015, 15(1): 1-8. doi: 10.1186/s12906-015-0520-z
[7]	Yu Qijian. Synergistic effects of calycosin and isoferulic acid on antioxidant and inhibiting proliferation of HepG2 cells[D]. Taian: Shandong Agricultural University, 2016.
[8]	Sadaf A, Ahmed S G, Aabgeena N, et al. Inhibition of advanced glycation end products by isoferulic acid and its free radical scavenging capacity: An in vitro and molecular docking study[J]. International Journal of Biological Macromolecules, 2018, 118(PB):1479-1487. doi: 10.1016/j.ijbiomac.2018.06.182
[9]	Gong S, Yin M, Yun Z. Kinetics of inhibitory effect of isoferulic acid on mushroom tyrosinase[J]. Journal of Cosmetic Science, 2013, 64(4): 235-241.
[10]	Lu W, Wang F, Zhang T, et al. Search for novel histone deacetylase inhibitors. Part II: Design and synjournal of novel isoferulic acid derivatives[J]. Bioorg Med Chem, 2014, 22(9): 2707-2713. doi: 10.1016/j.bmc.2014.03.019
[11]	Takahashi T, Miyazawa M. Tyrosinase inhibitory activities of cinnamic acid analogues[J]. Die Pharmazie, 2010, 65(12): 913-918.
[12]	Chochkova M, Stoykova B, Ivanova G, et al. N-Hydroxycinnamoyl amides of fluorinated amino acids: Synjournal, anti-tyrosinase and DPPH scavenging activities[J]. Journal of Fluorine Chemistry, 2013, 156:203-208. doi: 10.1016/j.jfluchem.2013.09.013
[13]	Wei Q Y, Jiang H, Zhang J X, et al. Synjournal of N -hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities[J]. Medicinal Chemistry Research, 2012, 21(8): 1905-1911. doi: 10.1007/s00044-011-9713-2
[14]	Qin R L, Lv C N, Zhao Y, et al. Assessment of phenolics contents and antioxidant properties in Cimicifuga dahurica (Turcz.) Maxim during drying process[J]. Industrial Crops and Products, 2017, 107:288-296. doi: 10.1016/j.indcrop.2017.06.004
[15]	Niu Chao, Li Gen, Medina. Synjournal and tyrosinase activity of new chalcone derivatives[J]. Journal of Chemistry of Colleges and Universities, 2014, 35(6): 1204-1211.

编号	含量/μL
编号	PBS	L-酪氨酸	样品	1% DMSO	酪氨酸酶
A	35	40		40	25
B	60	40		40
C	35	40	40		25
D	60	40	40

物质	IC₅₀/（mg·mL^-1）
a	1.13±0.14^*
b	1.41±0.03^**
c	1.36±0.13^**
d	1.25±0.09^**
e	1.18±0.07^**
f	1.41±0.12^**
IFA	2.71±0.35^**
V_C	0.018 5±0.005

物质	抑制率/%
a	95.43±0.37^*
b	28.35±1.84^*
c	60.35±2.85^*
d	75.60±0.42^*
e	93.65±2.67^*
f	86.12±3.15^*
IFA	94.49±0.54^*
熊果苷	89.51±0.47

物质	细胞存活率/%
a	96.92±2.68^*
b	96.26±3.51^*
c	93.95±4.51^*
d	87.96±2.41^**
e	88.66±3.37^*
f	92.76±5.01^*
IFA	88.76±1.67^*
熊果苷	99.31±0.34

物质	黑素含量/%
a	81.10±2.33^*
b	83.18±4.07^**
c	85.52±2.14^*
d	90.83±1.07^**
e	94.67±1.86^*
f	84.05±4.60^*
IFA	84.56±2.67^**
熊果苷	82.91±8.08

Study on synthesis and whitening activity of isoferic acid amides

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 5

References 15

Related Articles 15

Metrics

Comments

Recommended 10

[1]	Ning Li, Ennian Li, Hongbo Chen, Fang Cheng, Hengfang Zou, Hongpeng Chen. Advances of functional components in whitening cosmetic [J]. China Surfactant Detergent & Cosmetics, 2024, 54(1): 80-89.
[2]	Guo Fangyu, Han Tingting, Wang Xiaona, Chen Yurong, Wang Xiaomei, Yang Suzhen. Process optimization and anti-aging, moisturizing and whitening effects of traditional Chinese medicine bi-directional fermentation broth [J]. China Surfactant Detergent & Cosmetics, 2023, 53(5): 523-531.
[3]	Zhang Kaiqiang,Xu Hujun. Study on the synthesis and performance of diglucosyl gallic acid [J]. China Surfactant Detergent & Cosmetics, 2022, 52(2): 140-146.
[4]	Zha Yufeng,Huang Jiawen,Zhan Yi,Li Ting,Yan Hong,Wu Desong. Evaluation of antioxidant and whitening efficacy of Prunus mume extract [J]. China Surfactant Detergent & Cosmetics, 2022, 52(2): 172-179.
[5]	He Ruiyuan,Wang Shuo,Wei Guili,Gong Xiaomei,Wu Peiying,Miao Jianhua. Study of whitening effect and the mechanism of Zhuang medicine Poecilobdella manillensis extract [J]. China Surfactant Detergent & Cosmetics, 2022, 52(1): 35-43.
[6]	REN Qian-qian,WU Hua,JIN Jian-ming. Botanical cosmetic ingredient （Ⅱ）Research and development of tyrosinase inhibitors from plant extracts in skin whitening [J]. China Surfactant Detergent & Cosmetics, 2021, 51(3): 178-185.
[7]	WANG Ying,TANG Yin,WU Ya-ni. Effects of blend essential oil on melanogenesis in B16 cells of mice [J]. China Surfactant Detergent & Cosmetics, 2021, 51(3): 214-219.
[8]	GUO Xiao-dan,SONG Jing-jiu,ZHU Jun. Synthesis and anti-oxidant activity of feruloylamino acid ethyl ester [J]. China Surfactant Detergent & Cosmetics, 2020, 50(9): 624-628.
[9]	WANG Yong-heng,LIANG Yan-hui,SUN Pei-dong. Study on the dual-target whitening activities of Ligusticum chuanxiong Hort. extracts [J]. China Surfactant Detergent & Cosmetics, 2020, 50(4): 249-254.
[10]	ZHENG Xi,CHEN Zhi-duo,ZHANG De-meng,QIN Yi-min,YI Cai-xia,HUANG Xiao. Inhibitory effect of sodium alginate on the activity of tyrosinase [J]. China Surfactant Detergent & Cosmetics, 2019, 49(6): 388-392.
[11]	WANG Fei-fei,WANG Min-zhu,WANG Han,HUANG Shan,DANZENG Jiang-bai,LI Bin. The effect of extract of Nepeta angustifolia C.Y.Wu on tyrosinase activity and kinetics [J]. China Surfactant Detergent & Cosmetics, 2019, 49(5): 315-319.
[12]	LI Zhi-ying,WANG Xue-han,GAO Rui-yuan. Microwave-assisted extraction technology of skin-whitening agent in white Poria cocos [J]. China Surfactant Detergent & Cosmetics, 2019, 49(4): 238-243.
[13]	Dong WANG,Xue ZHAO,Jing-jiu SONG,Jun ZHU. Synthesis and the antioxidation study of the chemically modified derivatives of caffeic acid [J]. China Surfactant Detergent & Cosmetics, 2019, 49(2): 98-102.
[14]	HAO Mi-mi, WANG Yan, LIU Yuan-yuan, BAO Yan, LI Hong-yan, ZHENG Lin. Study on the mechanism of inhibition of melanin by phenethyl resorcinol [J]. China Surfactant Detergent & Cosmetics, 2018, 48(5): 293-298.
[15]	ZHANG Qing, XU Yong-wei, LIU Wei, GONG Sheng-zhao. Study on scavenging effect for hydroxyl radicals and inhibitory effect on tyrosinase in water soluble extracts fromChinese kiwifruit [J]. China Surfactant Detergent & Cosmetics, 2018, 48(3): 162-165.