Synthesis of the Natural Product 5,6,7,3',4'-Pentamethoxyisoflavone

NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2010, Vol. 23 ›› Issue (6): 956-960.

• Article • Previous Articles Next Articles

Synthesis of the Natural Product 5,6,7,3',4'-Pentamethoxyisoflavone

REN Wan-li¹，CHEN Rui²，JIN Ye²，ZHANG Tao²，LI Hong-qi^2*

¹Medical School, Baoji Vocational and Technological College, Baoji 721006, China; ²Key Laboratory of Science & Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China

Received:2009-05-27 Online:2011-01-10 Published:2011-10-19
Supported by:
This work was supported by Program for Changjiang Scholars and Innovative Research Team in University (No. IRT0526) and Shanghai Natural Science Foundation (No. 06ZR14001).

Abstract

Abstract:

The natural product 5,6,7,3',4'-pentamethoxyisoflavone was synthesized by a 5-step synthetic protocol including esterification, Fries transformation, and Vilsmeier-Haack reaction with 3,4-dimethoxyphenylacetic acid and 3,4,5-trimethoxyphenol as the starting materials. The overall yield of the target compound was 76% based on 3,4,5-trimethoxyphenol. The structure of the natural isoflavone 5,6,7,3',4'-pentamethoxyisoflavone was confirmed by NMR and elemental analysis.

Key words: 5,6,7,3',4'-pentamethoxyisoflavone, 3,4,5-trimethoxyphenol, fries transformation, Vilsmeier-Haack reaction, synthesis

REN Wan-Li, CHEN Rui, JIN Ye, ZHANG Tao, LI Hong-Qi. Synthesis of the Natural Product 5,6,7,3',4'-Pentamethoxyisoflavone[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2010, 23(6): 956-960.

References

1 Yokosuka A,Haraguchi M,Usui T,et al.Glaziovianin A,a new isoflavone, from the leaves of Ateleia glazioviana and its cytotoxic activity against human cancer cells.Bioorg Med Chem Lett,2007,17:3091-3094.
2 Deesamer S,Kokpol U,Chavasiri W,et al.Synthesis and biological evaluation of isoflavone analogues from Dalbergia oliveri.Tetrahedron,2007,63:12986-12993.
3 Zhang EJ,Ng KM,Luo KQ.Extraction and purification of isoflavones from soybeans and characterization of their estrogenic activities.J Agric Food Chem,2007,55:6940-6950.
4 Swami S,Krishnan AV,Moreno J,et al.Inhibition of prostaglandin synthesis and actions by genistein in human prostate cancer cells and by soy isoflavones in prostate cancer patients.Int J Cancer,2009,124: 2050-2059.
5 Gandhi Dasan R,Nagarajan NS,Narayanan V,et al.Dalspinin and Dalspinosin, two new isoflavones from Dalbergia spinosa roots.Indian J Chem,1982,21B:385-386.
6 Sethi ML,Taneja SC,Dhar KL,et al.Three isoflavone glycosides from Juniperus macropoda.Phytochemistry, 1983,22:289-292.
7 Veitch NC,Sutton PSE,Kite GC,et al.Six new isoflavones and a 5-deoxyflavonol glycoside from the leaves of Ateleia herbert-smithii.J Nat Prod,2003,66:210-216.
8 Chimura H,Sawa T,Kumada Y,et al.New isoflavones,inhibiting catechol-O-methyltransferase, produced by Streptomyces.J Antibiotics,1975,28:619-626.
9 Sethi ML,Taneja SC,Dhar KL,et al.Two isoflavones from Juniperus macropoda.Phytochemistry,1981,20: 341-342.
10 Agarwal VK,Thappa RK,Agarwal SG,et al.Isoflavones of two Iris species.Phytochemistry,1984,23: 2703-2704.
11 Rani M,Kalidhar SB.Trioxygenation sites in the A-ring of naturally occuring flavanones and isoflavones using 1H NMR spectroscopy.J Med Aromatic Plant Sci,1996,18:473-476.
12 Wang CL,Li HQ,Meng WD,et al.Trifluoromethylation of flavonoids and anti-tumor activity of the trifluoromethylated flavonoid derivatives.Bioorg Med Chem Lett,2005,15:4456-4458.
13 Jin Y,Li H.Synthesis and characterization of novel isoflavonoids containing perfluoroalkylsulfonyl group. Chem Res Appl (in Chinese),2007,19:928-932.
14 Wang CL,Zheng X,Meng WD,et al.Formation of the unexpected 3-alkylated flavonoids in the alkylation of B-ring substituted 5,7-dihydroxy flavones.Tetrahedron Lett,2005,46:5399-5402.
15 Jetter MC,Youngman MA,McNally JJ,et al.Heteroaryl β-tetralin ureas as antigonists of human TRPV1. Bioorg Med Chem Lett,2007,17:6160-6163.

[1]	CHEN Hui-juan, ZHANG Xing-ping, LI Ming-ming, WANG Kou. Total synthesis of broussonin C with tyrosinase inhibitory activity and its structural simplification [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2024, 36(7): 1226-1230.
[2]	ZHANG Wen-ting, YANG Min-jing, MEI Yu, WANG Ji-hua. Research status of kinsenoside [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2024, 36(2): 348-356.
[3]	ZHANG Tian-tian, ZHENG Bing-song, YUAN Hu-wei, YAN Dao-liang. Research progress on synthetic and metabolic pathways of plant volatile organic compounds and their release and sensing regulatory mechanisms [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2023, 35(6): 1068-1080.
[4]	CAI Chang-chun, FENG Ji, CHENG Ling, RAO Xiong-fei, ZHANG Jian-feng. Research progress and prospects on synthesis of taxol [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(增刊2): 155-162.
[5]	WANG Jun, FU Jian-hong, WANG Yu-miao, RUAN Wen-wei, NIE Hui-lin, CUI Feng-zhen, . Identification of a Streptomyces setonii from Lop Nur and inhibition effects of its metabolites on tyrosinase activity and melanin synthesis [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(9): 1548-1556.
[6]	MUKAIDAISI·Maihemuti, CHEN Jian, JIAO Chun-wei, XIE Yi-zhen. Progress in biosynthesis and application of L-ergothioneine [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(4): 713-721.
[7]	LIU Tian-fu, DU Xiao-nian, ZHANG Yi-fu, ZHANG Jian. Research progress on synthesis and activity of andrographolide derivatives [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2022, 34(12): 2142-2161.
[8]	CHEN Xiao-min, ZHOU Jun-jie, LI Jia-wei, CHEN Hao-xin, LIU Wen-li, XIE Guo. Research progress on synthesis and transformation of ginsenoside Rg₃ [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(增刊2): 155-164.
[9]	QIAO Miao, ZHU Peng-yan, LI Jing, LI Lu-jing, LI Guo-dong, DING Xiao, YUAN Wen-juan, WANG Xuan-jun. Steroidal alkaloids from Veratrum grandiflorum Loes. and their promoting activities for lysosomal biosynthesis [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(10): 1701-1706.
[10]	XIE Li-yuan, YIN Wen-Bing, LI Wei , GAO Wei. Advance on natural products and their pharmacological activities and biosynthesis from Beauveria species [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2021, 33(1): 150-164.
[11]	QU Shang-lan1,2#,REN Wei-wei1,2#,SONG Liu-dong2,FENG Wei-yang1*. The effects of retinoic acid on the expression of γ-butyrobetaine dioxygenase and carnitine biosynthesis in rat hepatocellular carcinoma cells [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2019, 31(10): 1791-1798.
[12]	CEN Bo,SHI Xian-chun,DUAN Wen-gui*,WANG Xiao-yu,LIN Gui-shan. Synthesis and Antifungal Activity of Maleated Rosin-based Dithiourea-amide Compounds [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2018, 30(9): 1526-1533.
[13]	JIANG Xiao-fei1,2*, ZHANG Wei3, XIONG Nan-qian1. Synthesis and Biological Evaluation of Novel Jatrorrhizine Triazoles as Potential Antimicrobial Reagents and Acetylcholinesterase Inhibitor [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2018, 30(4): 535-540.
[14]	WU Xiao-ying1, AN Ting-ting2, GAO Bing-miao3*. Chemical Synthesis and Insecticidal Activity of Conotoxin ImI [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2018, 30(12): 2203-2206.
[15]	LIU Can1,2, MA Lan-qing1, SUN Yuan-xia2. Hypoglycemic Mechanisms and Biosynthesis of Mogrosides from Siraitia grosvenorii Fruit:A Review [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2018, 30(11): 2023-2031.

Synthesis of the Natural Product 5,6,7,3',4'-Pentamethoxyisoflavone

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments