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Mini-Reviews in Medicinal Chemistry

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ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

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Mini-Review Article

Medicinal Plant Centipeda Minima: A Resource of Bioactive Compounds

Author(s): Nguyen Thi Thuy Linh, Nguyen Thi Thu Ha, Nguyen Thanh Tra, Le Thi Tu Anh, Nguyen Van Tuyen* and Ninh The Son*

Volume 21, Issue 3, 2021

Published on: 21 October, 2020

Page: [273 - 287] Pages: 15

DOI: 10.2174/1389557520666201021143257

Price: $65

Abstract

Background: Centipeda minima (the family Asteraceae) is an annual herbaceous plant native to the tropical regions, especially in eastern tropical Asia. C. minima is well-known in the list of medicinal plants with capacities in treatment of whooping cough, nasal allergy, malaria, and asthma. More than sixty reports on phytochemical and pharmacological aspects of this plant are now available, but a supportive review is insufficient.

Objective: The current review aims to make a compilation of almost all of the isolated compounds from the title plant, together with their pharmacological activities.

Methodology: Centipeda minima is a meaningful keyword to search for previous references, while the reliable databases, such as Sci-Finder, Google Scholar, Pub Med, Science Direct, the Web of Science, Scopus, Bentham science, Taylor Francis, Springer, IOP Science were utilized at most.

Conclusion: More than one hundred secondary metabolites, classifying as terpenoids, flavonoids, mono-phenols, fatty acids, amides, and other types, were isolated from this plant. Among them, sesquiterpene lactones are dominant in either C. minima species or numerous plants of genus Centipeda. These phytochemical groups also possessed various biological results like anti-cancer, anti-bacteria, anti-allergy, anti-virus, anti-inflammation, and hepatoprotective activities. With many kinds of bioactive results such as anti-cancer and anti-inflammation, the use of C. minima plant extracts and isolated compounds for drug development seems to be a futuristic strategy.

Keywords: Asteraceae, Centipeda minima, sesquiterpene lactones, secondary metabolites, phytochemistry, pharmacology.

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Graphical Abstract

[1]
Shi, Z.; Gilbert, M.G. Centipeda Loureiro. Fl. Conchinch. Flora of China, 2011, 20-21, 892.
[2]
Centipeda. Theplantlist.org (Accessed March 12, 2020).
[3]
Beattie, K.D. Phytochemical studies and bioactivity of Centipeda and Eremophila species.PhD thesis. Souhthern Cross University,, 2009.
[4]
Liang, H.X.; Bao, F.K.; Dong, X.P.; Zhu, H.J.; Lu, X.J.; Shi, M.; Lu, Q.; Cheng, Y.X. Two new antibacterial sesquiterpenoids from Centipeda minima. Chem. Biodivers., 2007, 4(12), 2810-2816.
[http://dx.doi.org/10.1002/cbdv.200790230] [PMID: 18081091]
[5]
Nguyen, N.Y.T.; Nguyen, T.H.; Dang, P.H.; Tran, Q.L. Three terpenoid glycosides of Centipeda minima. Phytochem. Lett., 2017, 21, 21-24.
[http://dx.doi.org/10.1016/j.phytol.2017.05.012]
[6]
Huang, W.; Yu, X.; Liang, N.; Ge, W.; Kwok, H.F.; Lau, C.B.S.; Li, Y.; Chung, H.Y. Anti-angiogenic activity and mechanism of sesquiterpene lactones from Centipeda minima. Nat. Prod. Commun., 2016, 11(4), 435-438.
[http://dx.doi.org/10.1177/1934578X1601100402] [PMID: 27396185]
[7]
Liu, R.; Dow Chan, B.; Mok, D.K.W.; Lee, C.S.; Tai, W.C.S.; Chen, S. Arnicolide D, from the herb Centipeda minima is a therapeutic candidate against nasopharyngeal carcinoma. Molecules, 2019, 24(10), 1908.
[http://dx.doi.org/10.3390/molecules24101908] [PMID: 31108969]
[8]
Huang, X.; Awano, Y.; Maeda, E.; Asada, Y.; Takemoto, H.; Watanabe, T.; Kojima-Yuasa, A.; Kobayashi, Y. Cytotoxic activity of two natural sesquiterpene lactones, isobutyroylplenolin and arnicolide D, on human colon cancer cell line HT-29. Nat. Prod. Res., 2014, 28(12), 914-916.
[http://dx.doi.org/10.1080/14786419.2014.889133] [PMID: 24588282]
[9]
Son, N.T. An overview of the genus Prismatomeris: Phytochemistry and biological activity. Bull. Fac. Pharm. Cairo Univ., 2017, 55, 11-18.
[http://dx.doi.org/10.1016/j.bfopcu.2017.03.003]
[10]
Ninh The. S. A review on the medicinal plant Dalbergia odorifera species: Phytochemistry and biological activity. Evid. Based Complement. Alternat. Med., 2017.20177142370
[http://dx.doi.org/10.1155/2017/7142370] [PMID: 29348771]
[11]
Son, N.T. Notes on the genus Paramignya: Phytochemistry and biological activity. Bull. Fac. Pharm. Cairo Univ., 2018, 56, 1-10.
[http://dx.doi.org/10.1016/j.bfopcu.2017.12.001]
[12]
Son, N.T. Genus Miliusa: A review of phytochemistry and pharmacology; Evid. Based Complement. Altern. Med, 2019, p. 8314693.
[13]
Son, N.T. Genus Erythrophleum: Botanical description, traditional use, phytochemistry and pharmacology. Phytochem. Rev., 2019, 18, 571-599.
[http://dx.doi.org/10.1007/s11101-019-09640-0]
[14]
Son, N.T. Secondary metabolites of genus Pandanus-An aspect of phytochemistry. Mini Rev. Org. Chem., 2019, 16, 689-710.
[http://dx.doi.org/10.2174/1570193X16666181206102740]
[15]
Pu, S.; Guo, Y.; Gao, W. Chemical constituents from Centipeda minima. Zhongguo Zhongyao Zazhi, 2009, 34(12), 1520-1522.
[PMID: 19777837]
[16]
Pu, S.C.; Guo, Y.Q.; Gao, W.Y.; Man, S.L.; Liu, C.X.; Xiao, P.G. Secondary metabolites and biosynthetic pathway approach in medicinal plant Centipeda minima. Asian J. Pharmacodynam. Pharmacokinet., 2009, 9, 233-238.
[17]
Liang, H.; Bao, F.; Dong, X.; Tan, R.; Zhang, C.; Lu, Q.; Cheng, Y. Antibacterial thymol derivatives isolated from Centipeda minima. Molecules, 2007, 12(8), 1606-1613.
[http://dx.doi.org/10.3390/12081606] [PMID: 17960076]
[18]
Bohlmann, F.; Zhongliang, C. New guaiannolides from Centipeda minima. Chin. Sci. Bull., 1984, 29, 900.
[19]
Iwakami, S.; Wu, J.B.; Ebizuka, Y.; Sankawa, U. Platelet activating factor (PAF) antagonists contained in medicinal plants: Lignans and sesquiterpenes. Chem. Pharm. Bull. (Tokyo), 1992, 40(5), 1196-1198.
[http://dx.doi.org/10.1248/cpb.40.1196] [PMID: 1394633]
[20]
Ding, L.F.; Liu, Y.; Liang, H.X.; Liu, D.P.; Zhou, G.B.; Cheng, Y.X. Two new terpene glucosides and antitumor agents from Centipeda minima. J. Asian Nat. Prod. Res., 2009, 11(8), 732-736.
[http://dx.doi.org/10.1080/10286020903029231] [PMID: 20183316]
[21]
Gupta, D.; Singh, J. Triterpenoid saponins from Centipeda minima. Phytochemistry, 1990, 29, 1945-1950.
[http://dx.doi.org/10.1016/0031-9422(90)85045-H]
[22]
Shanghi, R.; Srivastava, P.; Singh, J. Hydroquinone O-β-D-xylopiranoside from Centipeda minima. Indian J. Chem., 2001, 40B, 857-859.
[23]
Cheng, P.S.; Qiang, G.Y.; Yuan, G.W.; Jun, Z.T. New thymol derivate from Centipeda minima. Chem. Res. Chin. Univ., 2009, 25, 125-126.
[24]
Wu, L.; Liu, Y.; Chen, M.; Bi, Z.; Wang, H.; Liu, E. Chemical constituents of Centipeda minima. Zhongnan Yaoxue, 2016, 14, 351-354.
[25]
Zhang, X.; He, J.; Huang, W.; Huang, H.; Zhang, Z.; Wang, J.; Yang, L.; Wang, G.; Wang, Y.; Li, Y. Antiviral activity of the sesquiterpene lactones from Centipeda minima against influenza A virus in vitro. Nat. Prod. Commun., 2018, 13, 115-119.
[http://dx.doi.org/10.1177/1934578X1801300201]
[26]
Cheng, P.S. Study on anti-tumor activity of Centipeda minima. Anhui Nongye Kexue, 2013, 41, 13833-13834.
[27]
Taylor, R.S.; Towers, G.H.N. Antibacterial constituents of the Nepalese medicinal herb, Centipeda minima. Phytochemistry, 1998, 47(4), 631-634.
[http://dx.doi.org/10.1016/S0031-9422(97)00534-7] [PMID: 9461679]
[28]
Wu, J.B.; Chun, Y.T.; Ebizuka, Y.; Sankawa, U. Biologically active constituents of Centipeda minima: Isolation of a new plenolin ester and the antiallergy activity of sesquiterpene lactones. Chem. Pharm. Bull. (Tokyo), 1985, 33(9), 4091-4094.
[http://dx.doi.org/10.1248/cpb.33.4091] [PMID: 2418993]
[29]
Wu, J.B.; Chun, Y.T.; Ebizuka, Y.; Sankawa, U. Biologically active constituents of Centipeda minima: Sesquiterpenes of potential anti-allergy activity. Chem. Pharm. Bull. (Tokyo), 1991, 39(12), 3272-3275.
[http://dx.doi.org/10.1248/cpb.39.3272] [PMID: 1726075]
[30]
Wu, P.; Su, M.X.; Wang, Y.; Wang, G.C.; Ye, W.C.; Chung, H.Y.; Li, J.; Jiang, R.W.; Li, Y.L. Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima. Phytochemistry, 2012, 76, 133-140.
[http://dx.doi.org/10.1016/j.phytochem.2012.01.003] [PMID: 22277736]
[31]
Oh, H.M.; Kwon, B.M.; Baek, N.I.; Kim, S.H.; Lee, J.H.; Eun, J.S.; Yang, J.H.; Kim, D.K. Inhibitory activity of 6-O-angeloylprenolin from Centipeda minima on farnesyl protein transferase. Arch. Pharm. Res., 2006, 29(1), 64-66.
[http://dx.doi.org/10.1007/BF02977470] [PMID: 16491845]
[32]
Yu, H.W.; Wright, C.W.; Cai, Y.; Yang, S.L.; Phillipson, J.D.; Kirby, G.C.; Warhurst, D.C. Antiprotozoal activities of Centipeda minima. Phytother. Res., 1994, 8, 436-438.
[http://dx.doi.org/10.1002/ptr.2650080713]
[33]
Wu, H.; Liu, Y.; Yang, Y.; Xiao, M. Chemical constituents from ethyl acetate fraction of Centipeda minima. Shizhen Guoyi Guoyao, 2010, 21, 1096-1098.
[34]
Su, M.; Li, Y.; Chung, H.Y.; Ye, W. 2β-(Isobutyryloxy)florilenalin, a sesquiterpene lactone isolated from the medicinal plant Centipeda minima, induces apoptosis in human nasopharyngeal carcinoma CNE cells. Molecules, 2009, 14(6), 2135-2146.
[http://dx.doi.org/10.3390/molecules14062135] [PMID: 19553887]
[35]
Wu, P.; Li, X.G.; Liang, N.; Wang, G.C.; Ye, W.C.; Zhou, G.X.; Li, Y.L. Two new sesquiterpene lactones from the supercritical fluid extract of Centipeda minima. J. Asian Nat. Prod. Res., 2012, 14(6), 515-520.
[http://dx.doi.org/10.1080/10286020.2012.670222] [PMID: 22428717]
[36]
Sen, A.B.; Shukla, Y.N. Chemical constituents of Centipeda minima. J. Indian Chem. Soc., 1970, 47, 96.
[37]
Murakami, T.; Chen, C.M. Studies on the constituents of Centipeda minima O. Kuntze. I. Yakugaku Zasshi, 1970, 90(7), 846-849.
[http://dx.doi.org/10.1248/yakushi1947.90.7_846] [PMID: 5465397]
[38]
Rai, N.; Siddiqui, I.R.; Singh, J. Two new triterpenoids from Centipeda minima. Pharm. Biol., 1999, 37, 314-317.
[http://dx.doi.org/10.1076/phbi.37.4.314.5797]
[39]
Gupta, D.; Singh, J. Triterpenoid saponins from Centipeda minima. Phytochemistry, 1989, 28, 1197-1201.
[http://dx.doi.org/10.1016/0031-9422(89)80208-0]
[40]
Rai, N.; Singh, J. Two new triterpenoid glucosides from Centipeda minima. Indian J. Chem., 2001, 40B, 320-323.
[41]
Yang, Y.F.; Zhang, B.W.; Yan, B.; Zhang, Y.Q.; Wu, H.Z. Study on the chemical constituents of n-butanol extract fraction from Centipeda minima. Shizhen Guoyi Guoyao, 2013, 24, 2358-2359.
[42]
Cao, J.; Li, G. Chemical constituents of Centipeda minima. Zhongguo Zhongyao Zazhi, 2012, 37(15), 2301-2303.
[PMID: 23189738]
[43]
Liu, R.; Dow Chan, B.; Mok, D.K.W.; Lee, C.S.; Tai, W.C.S.; Chen, S. Arnicolide D, from the herb Centipeda minima, is a therapeutic candidate against nasopharyngeal carcinoma. Molecules, 2019, 24(10), 1908.
[http://dx.doi.org/10.3390/molecules24101908] [PMID: 31108969]
[44]
Liu, R.; Qu, Z.; Lin, Y.; Lee, C.S.; Tai, W.C.S.; Chen, S. Brevilin A induces cell cycle arrest and apoptosis in nasopharyngeal carcinoma. Front. Pharmacol., 2019, 10, 594.
[http://dx.doi.org/10.3389/fphar.2019.00594] [PMID: 31178739]
[45]
Qin, Y.; Lu, H. In vitro evaluation of anti-hepatoma activity of brevilin A: involvement of Stat3/Snail and Wnt/β-catenin pathways. RSC Advances, 2019, 9, 4390.
[http://dx.doi.org/10.1039/C8RA08574A]
[46]
Wang, Y.; Yu, R.Y.; Zhang, J.; Zhang, W.X.; Huang, Z.H.; Hu, H.F.; Li, Y.L.; Li, B.; He, Q.Y. Inhibition of Nrf2 enhances the anticancer effect of 6-O-angeloylenolin in lung adenocarcinoma 2017..
[47]
Yadav, V.R.; Prasad, S.; Sung, B.; Kannappan, R.; Aggarwal, B.B. Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins (Basel), 2010, 2(10), 2428-2466.
[http://dx.doi.org/10.3390/toxins2102428] [PMID: 22069560]
[48]
Jing, B.; Liu, M.; Yang, L.; Cai, H.Y.; Chen, J.B.; Li, Z.X.; Kou, X.; Wu, Y.Z.; Qin, D.J.; Zhou, L.; Jin, J.; Lei, H.; Xu, H.Z.; Wang, W.W.; Wu, Y.L. Characterization of naturally occurring pentacyclic triterpenes as novel inhibitors of deubiquitinating protease USP7 with anticancer activity in vitro. Acta Pharmacol. Sin., 2018, 39(3), 492-498.
[http://dx.doi.org/10.1038/aps.2017.119] [PMID: 29168472]
[49]
Chan, C.O.; Jin, D.P.; Dong, N.P.; Chen, S.B.; Mok, D.K.W. Qualitative and quantitative analysis of chemical constituents of Centipeda minima by HPLC-QTOF-MS & HPLC-DAD. J. Pharm. Biomed. Anal., 2016, 125, 400-407.
[http://dx.doi.org/10.1016/j.jpba.2016.04.029] [PMID: 27131150]
[50]
Chan, C.; Xie, X.; Wan, S.; Zhou, G.; Yuen, A.C.; Mok, D.K.; Chen, S. Qualitative and quantitative analysis of sesquiterpene lactones in Centipeda minima by UPLC-orbitrap-MS and UPLCQQQ- MS. J. Pharmaceut. Biomed.,. 2019.
[51]
Soetardjo, S., Jr; Jong, P.C.; Ahmad, M.N.; Lachimanan, Y.L.; Sreenivasan, S. Chemical composition and biological activity of the Centipeda minima (Asteraceae). Malays. J. Nutr., 2007, 13(1), 81-87.
[PMID: 22692191]
[52]
Zhang, X.; Xia, Y.; Yang, L.; He, J.; Li, Y.; Xia, C. Brevilin A, a sesquiterpene lactone, inhibits the replication of influenza A virus in vitro and in vivo. Viruses, 2019, 11(9), 835.
[http://dx.doi.org/10.3390/v11090835] [PMID: 31500389]
[53]
Zhou, Y.; Yan, Y.; Li, S.; He, D.; Xiong, S.; Wei, S.; Liu, W.; Hu, L.; Wang, Q.; Pan, H.; Cheng, Y.; Liu, Y. 6-O-Angeloylplenolin exerts neuroprotection against lipopolysaccharide-induced neuroinflammation in vitro and in vivo. Acta Pharmacol. Sin., 2019, 0, 1-12.
[PMID: 31213669]
[54]
Lin, X.; Zhang, S.; Huang, R.; Wei, L.; Tan, S.; Liang, S.; Tian, Y.; Wu, X.; Lu, Z.; Huang, Q. Helenalin attenuates alcohol-induced hepatic fibrosis by enhancing ethanol metabolism, inhibiting oxidative stress and suppressing HSC activation. Fitoterapia, 2014, 95, 203-213.
[http://dx.doi.org/10.1016/j.fitote.2014.03.020] [PMID: 24704336]
[55]
Li, Y.; Zeng, Y.; Huang, Q.; Wen, S.; Wei, Y.; Chen, Y.; Zhang, X.; Bai, F.; Lu, Z.; Wei, J.; Lin, X. Helenalin from Centipeda minima ameliorates acute hepatic injury by protecting mitochondria function, activating Nrf2 pathway and inhibiting NF-κB activation. Biomed. Pharmacother., 2019, 119109435
[http://dx.doi.org/10.1016/j.biopha.2019.109435] [PMID: 31520915]
[56]
Vishwanath, P.B.; Laxmi, V.; Madhavi, Y.M.; Ramya, L.P. Phytochemical Screening, antimicrobial and antiproliferative properties of Centipeda minima (Asteraceae) on prostate epithelial cancer cells. J. Pharm. Res., 2012, 5, 4804-4807.
[57]
Guo, Y.Q.; Sun, H.Y.; Chan, C.O.; Liu, B.B.; Wu, J.H.; Chan, S.W.; Mok, D.K.; Tse, A.K.; Yu, Z.L.; Chen, S.B. Centipeda minima (Ebushicao) extract inhibits PI3K-Akt-mTOR signaling in nasopharyngeal carcinoma CNE-1 cells. Chin. Med., 2015, 10, 26.
[http://dx.doi.org/10.1186/s13020-015-0058-5] [PMID: 26388933]
[58]
Sohn, S.H.; Lee, H.; Nam, J.Y.; Kim, S.H.; Jung, H.J.; Kim, Y.; Shin, M.; Hong, M.; Bae, H. Screening of herbal medicines for the recovery of cisplatin-induced nephrotoxicity. Environ. Toxicol. Pharmacol., 2009, 28(2), 206-212.
[http://dx.doi.org/10.1016/j.etap.2009.04.005] [PMID: 21784004]
[59]
Lee, M.M.; Chan, B.D.; Wong, W.Y.; Qu, Z.; Chan, M.S.; Leung, T.W.; Lin, Y.; Mok, D.K.; Chen, S.; Tai, W.C. Anticancer activity of Centipeda minima extract in triple negative breast cancer via inhibition of AKT, NF-kB, and STAT3 signaling pathways. Front. Oncol., 2020, 10, 491.
[http://dx.doi.org/10.3389/fonc.2020.00491] [PMID: 32328465]
[60]
Mazzio, E.A.; Li, N.; Bauer, D.; Mendonca, P.; Taka, E.; Darb, M.; Thomas, L.; Williams, H.; Soliman, K.F.A. Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis. BMC Complement. Altern. Med., 2016, 16(1), 467.
[http://dx.doi.org/10.1186/s12906-016-1429-x] [PMID: 27846826]
[61]
Taylor, R.S.L.; Manandhar, N.P.; Hudson, J.B.; Towers, G.H.N. Antiviral activities of Nepalese medicinal plants. J. Ethnopharmacol., 1996, 52(3), 157-163.
[http://dx.doi.org/10.1016/0378-8741(96)01409-2] [PMID: 8771457]
[62]
Lee, H.; Lin, J.Y. Antimutagenic activity of extracts from anticancer drugs in Chinese medicine. Mutat. Res., 1988, 204(2), 229-234.
[http://dx.doi.org/10.1016/0165-1218(88)90093-6] [PMID: 3278214]
[63]
Kim, H.P.; Son, K.H.; Chang, H.W.; Kang, S.S. Anti-inflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol. Sci., 2004, 96(3), 229-245.
[http://dx.doi.org/10.1254/jphs.CRJ04003X] [PMID: 15539763]
[64]
Sarkar, A.; Tripathi, V.D.; Sahu, R.K; Faller, E.M. Pharmacognostic and preliminary phytochemical evaluation of Centipeda minima and Bauhinia purpurea leaves. UK. J. Pharm. Biosci, 2017, 5, 08-16..
[65]
Li, S.Y.; Zhou, Y.L.; He, D.H.; Liu, W.; Fan, X.Z.; Wang, Q.; Pan, H.F.; Cheng, Y.X.; Liu, Y.Q. Centipeda minima extract exerts antineuroinflammatory effects via the inhibition of NF-κB signaling pathway. Phytomedicine, 2020.67153164
[http://dx.doi.org/10.1016/j.phymed.2019.153164] [PMID: 31954258]
[66]
Wang, Y.J.; Wang, X.Y.; Hao, X.Y.; Yan, Y.M.; Hong, M.; Wei, S.F.; Zhou, Y.L.; Wang, Q.; Cheng, Y.X.; Liu, Y.Q. Ethanol extract of Centipeda minima exerts antioxidant and neuroprotective effects via activation of the Nrf2 signaling pathway; Oxid. Med. Cel. Longev, 2019, pp. 1-16.
[http://dx.doi.org/10.1155/2019/9421037]

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