Flavonoids Isolated from the genus Ficus and Their Biological Activities

doi:10.21127/yaoyimr20210004

Medicine Research ›› 2021, Vol. 5 ›› Issue (2): 210004-210004.DOI: 10.21127/yaoyimr20210004

Flavonoids Isolated from the genus Ficus and Their Biological Activities

Yaxian Zhao,^‡,a,b Jing Niu,^‡,a Qinru Zhou,^a,b Yan Chen,^a,b Shiquan Gan,^a,b Xiangchun Shen,^*,a,b and Nenling Zhang^*,a,b

a School of Pharmacy, Guizhou Medical University/Engineering Center of Efficient Utilization of Natural Medicinal Resources, Guiyang, Guizhou 550025, China;
b High Educational Key Laboratory of Guizhou Province for Natural Medicinal Pharmacology and Drug Druggability/Key Laboratory of Optimal Utilization of Natural Medicinal Resources, Guiyang, Guizhou 550025, China

收稿日期:2021-03-20 接受日期:2021-05-05 出版日期:2021-06-20 发布日期:2021-06-21
通讯作者: *, Email: shenxiangchun@126.com (X. S.); nenlingzhang@foxmail.com (N. Z.) ‡ Y. Z. and J. N. contributed equally to this work.

Flavonoids Isolated from the genus Ficus and Their Biological Activities

Yaxian Zhao,^‡,a,b Jing Niu,^‡,a Qinru Zhou,^a,b Yan Chen,^a,b Shiquan Gan,^a,b Xiangchun Shen,^*,a,b and Nenling Zhang^*,a,b

a School of Pharmacy, Guizhou Medical University/Engineering Center of Efficient Utilization of Natural Medicinal Resources, Guiyang, Guizhou 550025, China;
b High Educational Key Laboratory of Guizhou Province for Natural Medicinal Pharmacology and Drug Druggability/Key Laboratory of Optimal Utilization of Natural Medicinal Resources, Guiyang, Guizhou 550025, China

Received:2021-03-20 Accepted:2021-05-05 Online:2021-06-20 Published:2021-06-21
Contact: *, Email: shenxiangchun@126.com (X. S.); nenlingzhang@foxmail.com (N. Z.) ‡ Y. Z. and J. N. contributed equally to this work.

摘要/Abstract

摘要： There are about 1000 species in the genus Ficus and many can be used for medicinal purpose. The medicinal plants of this genus mainly contain terpenoids, flavonoids, alkaloids, and coumarins. In this paper, we summarized flavonoids isolated from the genus Ficus and their pharmacological effects including anti-bacterial, anti-inflammatory, antitumor, antioxidant, antiviral, protective activities on the cardiovascular system and other activities.

关键词: Ficus plants, chemical constituents, flavonoids, biological activity

Abstract: There are about 1000 species in the genus Ficus and many can be used for medicinal purpose. The medicinal plants of this genus mainly contain terpenoids, flavonoids, alkaloids, and coumarins. In this paper, we summarized flavonoids isolated from the genus Ficus and their pharmacological effects including anti-bacterial, anti-inflammatory, antitumor, antioxidant, antiviral, protective activities on the cardiovascular system and other activities.

Key words: Ficus plants, chemical constituents, flavonoids, biological activity

Yaxian Zhao, Jing Niu, Qinru Zhou, Yan Chen, Shiquan Gan, Xiangchun Shen, Nenling Zhang. Flavonoids Isolated from the genus Ficus and Their Biological Activities[J]. Medicine Research, 2021, 5(2): 210004-210004.

参考文献

[1] Editorial Committee of Chinese Flora of Chinese Academy of Sciences, Flora of China, Beijing, Science Press, 1998, Vol. 23, p. 66.
[2] Yan, C. C. Ph.D. Dissertation, Hainan University, Hainan, China, 2011.
[3] Fan, M. S.; Ye, G.; Huang, C. G. The advances of chemistry and pharmacological study of Ficus genus. Nat. Prod. Res. Dev. 2005, 17, 497–504.
[4] Li, C.; Bu, P. B.; Yue, D. K.; Sun, Y. F. Chemical constituents from roots of Ficus hirta. Chin. J. Chin. Mater. Med. 2006, 31, 131–133.
[5] Zhao, L. P.; Di, B.; Feng F. Chemical constituents from the roots of Ficus hirta. Pharm. Clin. Res. 2008, 16, 5–7.
[6] Jia, J.; Wang, Y.; Li, Y. L.; Ye, W. C. Study on the flavonoids and coumarins of Ficus simplicissima Lour. Chem. Ind. Forest Prod. 2008, 28, 52–55.
[7] Zheng, R. R.; Ji, J.; Wang, W. J.; Yang, H. B.; Zhang, Q. W. Study on the chemical constituents of Ficus simplicissima Lour. J. Chin. Med. Mater. 2013, 38, 3696–3701.
[8] Wu, W. M.; Hou, X. J.; Liu, L. M.; Tang, S. M.; Tong, L. F. Advance in chemical constituents and pharmacological activities of Ficus pumila. Chin. Med. J. Res. Prac. 2017, 31, 78–86.
[9] Luisa, P.; Elisabetta, E. C.; Ivano, M. Flavonoids from Ficus pumila. Biochem. Syst. Ecol. 2000, 28, 287–289.
[10] Zhang, F.; Zhang, J. Q.; Kong, L. Y. Research progress on chemical constituents of Ficus pumila. Chin. Tradit. Herbal. Drugs 2009, 40, 1554–1555.
[11] Fan, M.; S.; Ye, G.; Huang, C. G. Study on chemical constituents of Ficus pumila. Chin. Herb. Med. 2005, 36, 984–986. [12] Wei, C. L.; Fan, G. Y. Chemical constituents from Ficus pumila. Chin. Herb. Med. 2014, 45, 615–621. [13] Shao, T. M. Ph.D. Dissertation, Hainan Normal University, Hainan, China, 2013.
[14] Ya, L.; Zhang, X. Q.; Wang, Y.; Zhang, Q. W.; Chen, J. X.; Ye, W. C. Two new phenolic compounds from the roots of Ficus hirta. J. Nat. Prod. Res. 2010, 24, 621–625.
[15] Kiem, P. V.; Cuong, N. X.; Nhiem, N. X.; Thu, V. K.; Ban, N. K.; Minh, C. V.; Tai, B. H.; Hai, T. N.; Lee, S. H.; Jang, H. D.; Kim, Y. H. Antioxidant activity of a new C-glycosylflavone from the leaves of Ficus microcarpa. Bioorg. Med. Chem. Lett. 2011, 21, 633–637.
[16] Zaffer, B. M.; Mohd, A.; Rasool, S. New flavonol diesters from the stem bark of Ficus carical. Int. J. Clin. Pharm. Res. 2012, 3, 140–143.
[17] Zheng, F. S.; Chun, L.; Bang, W. Y. New Alkaloids and α-Glucosidase Inhibitory flavonoids from Ficus hispida. Chem. Mater. 2016, 4, 445–450.
[18] Ramadan, M. A.; Ahmad, A. S.; Nafady A M. Chemical composition of the stem bark and leaves of Ficus pandurata Hance. Nat. Prod. Res. 2009, 23, 1218–1230.
[19] Zhang, X. P.; Jiang, K. Z.; Lu, H. Q. Identification and characterization of major chemical compounds in the ethyl acetate extract from Ficus pandurata Hance. aerial roots by HPLC-Q-TOF MS. Chin. J. Mass Spectrom. Soc. 2015, 36, 310–320.
[20] Liu, M.; He, M. G.; Mei, Y.; Chen, X. Q.; Wang, J. H. Research progress in medicinal plant of Ficus microcarpa. Guangdong Agric. Sci. 2020, 47, 15–22.
[21] Yang, S. B.; Zhang, R. Z.; Jiang, Z. Y. Chemical constituents from root of Ficus tikoua Bur. Chin. Tradit. Pat. Med. 2014, 36, 554–558.
[22] Qi, C. C.; Chen, W. H.; Chen, G. Y.; Song, X. P.; Han, C. R. Chemical constituents from roots of Ficus auriculata. Chin. Herb. Med. 2013, 22, 3127–3130.
[23] Qi, C. C.; Han, C. R.; Chen, W. H.; Wu, Z. Y.; Ran, X. CCS 9th National Symposium on Natural Organic Chemistry, Chinese Chemical Society, Shanghai, 2012, p. 89.
[24] Shao, T. M.; Song, X, P.; Chen, G. Y.; Han, C. R.; Li, X. B. CCS 11th National Symposium on Natural Organic Chemistry, Chinese Chemical Society, Shanghai, 2016, p. 270.
[25] Hu, Y. J.; Wu, X. P.; Liu, N.; Zhang, F. X.; Lu, Y. Y. Flavan components with anti-HSV activity in the leaves of Ficus microcarpa. Trop. Subtrop. Botany 2010, 18, 559–563.
[26] Chen, S. F.; Liu, Y. C.; Long, F. L. Advances in study on chemical constituents of Ficus genus. J. Yangling. Vocat. Tech. Coll. 2010, 9, 15–19.
[27] Wang, X. G.; Shen, L. T.; Zeng, Y. Y.; Tian, Y. Q.; Xu, H. H. Flavonoids in Ficus sarmentosa var. Chin. Herb. Med. 2010, 41, 526–529.
[28] Wang, Y. L.; Duan, S. L.; Zhang, Q. Q.; Cheng, W.; Liang, H. Chemical constituents from stems of Ficus tsiangii. Chin. Herb. Med. 2014, 45, 333–336.
[29] Zhang, X. Q.; Jiang, W. W.; Wang, Y.; Li, Y. L.; Ye, W. C. A new phenylpropionate in the root of Ficus stenophylla. Acta Pharmacol. Sin. 2008, 43, 281–283.
[30] Xu, Z. S.; Li, S. M.; Feng, G. X. Studies on Chemical Constituents from Stem of Ficus ischnopoda. Chin. J. Exp. Tradit. Med. Form. 2013, 19, 152–155.
[31] Zhang, W. P.; Zhang, X. P.; Liu, N.; Rao, G. X. A review on ethnic medicine Ficus tikoua Bur.. Mod. Chin. Med. 2016, 18, 531–534.
[32] Wei, S. P.; Lu, L. N.; Ji, Z. Q. Chemical constituents from Ficus tikoua. Chem. Nat. Compd. 2012, 48, 484–485.
[33] Fu, G. M.; Li, W. J.; Huang, X. Z.; Zhang, R. Z.; Tian, K.; Hou, S. Q; Li, Y. K. Antioxidant and alpha-glucosidase inhibitory activities of isoflavonoids from the rhizomes of Ficus tikoua Bur. Nat. Prod. Res. 2018, 32, 399–405.
[34] Xu, W.; Wang, P.; Li, S. Z. Study on the chemical constituents of the rhizomes of Ficus tikoua Bur. Nat. Prod. Res. Dev. 2011, 23, 270–272. [35] Yannick, S. F.; Bankeu, J. J. K.; Ali, M. S. Flavonoids and other bioactive constituents from Ficus thonningii Blume. (Moraceae). Phytochem. Lett. 2015, 11,139–145.
[36] Shao, M. H.; Zhang, W. H.; Zhang, M. M.; Liu, Y. P.; Zhao, F.; Fu, Y. H. Chemical constituents from fruits of Ficus carica. Chin. Tradit. Herbal. Drugs 2019, 50, 2425–2528.
[37] Bankeu, J. K.; Bankeu, R.; Khayala, B. N. Isoflavone dimers and other bioactive constituents from the figs of Ficus mucuso. J. Nat. Prod. 2011, 74, 1370–1378.
[38] Shao, T. M.; Li, X. B.; Qi, C. C.; Chen, G. Y. ChemicaI constituents of isoflavonoids from roots of Ficus auriculata. Chin. J. Org. Chem. 2018, 38, 710–714.
[39] Shao, T. M.; Song, X. P.; Han, C. R.; Chen, G. Y.; Chen, W. H. Chemical constituents of the stems of Ficus auriculata Lour. J. Asian Nat. Prod. Res. 2013, 25, 624–627.
[40] Chiang, Y. M.; Kuo, Y. H. Novel triterpenoids from the aerial roots of Ficus auriculata Lour. Nat. Prod. Res. 2017, 34, 7656–7661.
[41] Gan, C. Y.; Zhu, W. F.; Su, S. Z.; Pang, B. A review on chemical constituents and pharmacological activities of Ficus hispida Linn. Strait. Pharm. China 2018, 30, 31–36.
[42] Susan, D. R.; Mathew, B. C.; Dev, K. S.; Augusti, K. T. Antioxidant effect of two flavonoids from the bark of Ficus bengalensis Linn in hyperlipidemic rats. Indian J. Exp. Biol. 1998, 36, 902–906.
[43] Ase, B. D.; Warjeet, S. Isolation and antimicrobial studies of the compounds isolated from the stem bark of Ficus hispida Linn. Asian J. Chem. 2008, 20, 6027–6032.
[44] Guo, S.; Zhang, W. X.; Yu, W. Research progress on the pharmacological effects of apigenin. Hubei Univ. Sci. Technol. 2016, 30, 273–276.
[45] Ghorbani, A. Mechanisms of antidiabetic effects of flavonoid rutin. Biochem. Pharmacol. 2017,10, 305-312.
[46] Jang, Y. H.; Park, R. Y.; Kim, K. M. Antimicrobial activity of chrysoeriol 7 and chochlioquinone 9, white-backed planthopper- resistant compounds, against rice pathogenic strains. J. Biol. Basel 2020, 9, 382.
[47] Edziri, H.; Mastouri, M. H.; Mahjoub, M. A. Antibacterial, antifungal and cytotoxic activities of two flavonoids from Retama raetam flowers. Mol. Phys. 2012, 17, 7284–7293.
[48] Kim, J. Y.; Shim, S. H. Rotundifolia anti-atherosclerotic effects of fruits of and their isolated compounds via inhibition of human LDL and HDL oxidation. Biomol. Eng. 2019, 9, 727–744.
[49] He, J.; Chen, L.; David, H.; Shi, W. Y.; Lu, Q. Y. Antibacterial compounds from Glycyrrhiza uralensis. J. Nat. Prod. 2006, 69, 121–124.
[50] Qi, C. C.; Fu, Y. H.; Chen, W. H. A new isoflavone from the roots of Ficus auriculata. Nat. Prod. Res. 2018, 32, 43–47.
[51] Anthonia, A. A.; Angus, N. O.; Ugochukwu, M. O. Secondary metabolites of endophytic fungi from Newbouldia laevis and Cassia tora leaves: prospecting for new antimicrobial agents. Rec. Pat. Antiinfect Drug Discov. 2021, 12, 22.
[52] Zhang, B. B. Research on plant flavonoids. J. Vision. 2018, 8, 155–157.
[53] Xie, Q.; Wang, Q.; Gao, S. Q. Advances on the biological activity and mechanism of hesperidin. Electron. J. Metab. Nutr. Cancer 2020, 7, 13–17. [54] Han, W.; Xing, Y.; Kang, T. G. Research progress on the biological activity of luteolin. Yunnan J. Tradi. Chin. Med. 2010, 31, 60–62.
[55] Yan, J.; Zheng, M. D.; Cui, Y. H. Shandong Med. J. 2017, 57, 110–112.
[56] Nie, L.; Peng, L.; Li, Y. F.; Wang, Q. X. Research advances in the biological activities and mechanism of astragalin. Chin. J. Trop. Agr. 2020, 40, 64–70.
[57] Wu, J. Y.; Chen, Y. J.; Bai, L. Chrysoeriol ameliorates TPA-induced acute skin inflammation in mice and inhibits NF-κB and STAT3 pathways. Phytomedicine 2020, 68, 153173.
[58] Jiao, B.; Xu, C. T.; Li, Qi. Chemical constituents of camellia cumin flavonoids and their in vitro anti-inflammatory activities. Chin. J. Chem. 2019, 41, 89–95.
[59] Wu, J.; Liu, K.; Shi, X. H. The anti-inflammatory activity of several flavonoids isolated from Murraya paniculata on murine macrophage cell line and gastric epithelial cell (GES-1). Pharm. Biol. 2016, 54, 868–881.
[60] Qi, Z.; Fang, X.; Xie, Y.; Wang, L.; Zhao, Y.; Zhao, L. Bioassay-guided isolation of anti-inflammatory constituents from Celtis sinensis leaves. J. Food Biochem. 2021, 45, 13580–13591.
[61] Guo, H.; Xu, J. Pharmacological Effects of Orientin. Chin. J. Ethnomed. Ethnopharm. 2014, 10, 5–6.
[62] An, M.; Kim, H.; Moon, J. M.; Ko, H. S.; Clayton, P.; Lim, Y. H. Enzyme-treated Zizania iatifolia ethanol extract protects from UVA irradiation-induced wrinkle formation via inhibition of iysosome exocytosis and reactive oxygen species generation. Antioxidants Res. 2020, 9, 912.
[63] Muramatsu, D.; Uchiyama, H.; Kida, H.; Iwai, A. In vitro anti-inflammatory and anti-lipid accumulation properties of taxifolin-rich extract from the Japanese larch, Larix kaempferiIn. J. Heliyon. 2020, 6, 5505–5556.
[64] Shui, L.; Wang, W.; Xie, M.; Ye, B.; Li, X.; Liu, Y.; Zheng, M. Isoquercitrin induces apoptosis and autophagy in hepatocellular carcinoma cells via AMPK/mTOR/p70S6K signaling pathway. J. Aging (Albany NY), 2020, 12, 24318–24332.
[65] Pereira, C. V.; Duarte, M.; Silva, P, L. Polymethoxylated flavones target cancer stemness and improve the antiproliferative effect of 5-fluorouracil in a 3D cell model of colorectal cancer. Nutr. J. 2019, 11, 326–336.
[66] Borah, N.; Gunawardana, S.; Torres, H. ; McDonnell, S.; Van Slambrouck, S. 5,6,7,3',4',5'-Hexamethoxyflavone inhibits growth of triple-negative breast cancer cells via suppression of MAPK and Akt signaling pathways and arresting cell cycle. Int. J. Oncol. 2017, 51, 1685–1693.
[67] Chen, S.; Ma, J.; Yang, L.; Teng, M.; Lai, Z. Q.; Chen, X.; He, J. Anti-glioblastoma activity of kaempferol via programmed cell death induction: involvement of autophagy and pyroptosis. Front Bioeng Biotech. 2020, 8, 614419–614429.
[68] Kuete, V.; Ngnintedo, D. Fotso, G. W.; Ngadjui, B. T.; Keumedjjo, F.; Yeboah, S. O.; Andrae-Marobela, K.; Sivas, H. Cytotoxicity of seputhecarpan D, thonningiol and 12 other phytochemicals from African flora towards human carcinoma cells. BMC Complem. Altern. Med. 2018, 18, 36–48.
[69] Won, Y. S.; Seo, K. L. Lupiwighteone induces caspase-dependent and independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway. Food Chem. 2020, 135, 110863.
[70] Kang, M. J.; Kim, S. Y.; Kwon, E. B.; Jo, Y. H.; Lee, M. K.; Lee, H. S.; Moon, D. O.; Kim, M. O. Derrone induces autophagic cell death through induction of ROS and ERK in A549 cells. Plos One. 2019, 14, 218659–218674.
[71] Daveri, E.; Adamo, A. M.; Alfine, E.; Zhu, W.; Oteiza, P. I. Hexameric procyanidins inhibit colorectal cancer cell growth through both redox and non-redox regulation of the epidermal growth factor signaling pathway. Redox. Biol. 2021, 38, 101830–101841.
[72] Kamalakkannan, N.; Prince, P. S. Antihyperglycaemic and antioxidant effect of rutin, a polyphenolic flavonoid, in streptozotocin-induced diabetic wistar rats. Basic Clin. Pharmacol. Toxicol. 2006, 98, 97–103.
[73] Du, Q. Z.; Zhao, Y. H.; Li, Bo. The structure identification and antioxidant activity analysis of flavonoids from the flowers of Evergreen oilseed cane. J. Food Sci. 2011, 32, 111–115.
[74] Mendez, P. P.; Alday, E.; Valdez, J.; Hernandez, J.; Valencia, D.; Velazquez, C. Seasonality modulates the cellular antioxidant activity and antiproliferative effect of sonoran desert propolis. Antioxidants Basel. 2020, 9, 1294–1309.
[75] Phan, V. K.; Nguyen, X. C.; Nguyen, X. N. Antioxidant activity of a new C-glycosyl flavone from the leaves of Ficus microcarpa. Bioorg. Med. Chem. Lett. 2011, 21, 633–637.
[76] Tang, L.; Qin, Y.; Ling, K.; Wan, H. Eriodictyol inhibits the growth of CNE1 human nasopharyngeal cancer growth by targeting MEK/ERK signalling pathway, inducing cellular autophagy and inhibition of cell migration and invasion. J. BUON. 2020, 25, 2389–2394.
[77] Jin, Y.; Lu, Y.; Han, G. Z.; Sun, H. J.;Yu, H. S.; Jin, F. X. Comparative study on the anti-free radical activities of quercetin, isoquercetin and rutin. Chin. Tradit. Herbal. Drugs. 2007, 38, 408–412.
[78] Guo, Y. M. Ph.D. Dissertation, Dalian Medical University, Liaoning, China, 2011.
[79] Jiang, H. W.; Li, C. Y.; Zhao, C. J.; Ren, X. T. The chemical constituents, pharmacological effects and clinical application of figs. Heilongjiang Sci. J. 2019, 10, 12–15.
[80] Lin, J. Clinical pharmaceutical special of rutin. Chin. J. Clini. Pharmacol. 2009, 3, 256–263.
[81] Xu, L.; Sun, P. Ph.D. Dissertation, Jiangxi University of Traditional Chinese Medicine, Jiangxi, China, 2015.
[82] Geng, G. X.; Huang, Y. W.; Guo, F. J. The research progress of isopentenyl flavonoids in psoralen and their pharmacological effects. Nat. Prod. Res. Dev. 2013, 25, 1297–1301.
[83] Xu, M. J. Wu, B.; Ding, T.; Chu, J. H.; Li. C.Y.; Zhang, J.; Wu, T.; Wu, J.; Liu, S. J.; Liu, S. L. Simultaneous characterization of prenylated fla-vonoids and isoflavonoids in Psoralea corylifolia L. by liquid chromatography with diode-array detection and quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2012, 26, 2343–2358.

Flavonoids Isolated from the genus Ficus and Their Biological Activities

Flavonoids Isolated from the genus Ficus and Their Biological Activities

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