Login Register Cart 0
Generic placeholder image

Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Bioactive Flavonoids from Verbenaceae

Author(s): Kui-Wu Wang* and Ting-Ting Zhang

Volume 17, Issue 6, 2020

Page: [754 - 766] Pages: 13

DOI: 10.2174/1570193X16666191007170602

Price: $65

Abstract

Flavonoids are widely distributed in the plant kingdom and possess a variety of biological activities, such as anti-oxidant, anti-inflammatory, and anti-viral activities. Due to the structural diversity and biological activity, flavonoid derivatives isolated from Verbenaceae family have received a lot of attention by the research scholars. In this paper, a total of 150 natural flavonoids isolated from Verbenaceae and their bioactivities were summarized.

Keywords: Anti-inflammatory, anti-oxidant, anti-virus, biological activities, flavonoids, structure, verbenaceae.

« Previous
Graphical Abstract

[1]
Kar, P.; Goyal, A.K.; Das, A.P.; Sen, A. Antioxidant and pharmaceutical potential of Clerodendrum L.: An overview. Int. J. Green Pharm., 2014, 8(4), 210-216.
[http://dx.doi.org/10.4103/0973-8258.142671]
[2]
Onofre, S.B.; Santos, Z.M.Q.; Kagimura, F.Y.; Mattiello, S.P. Antioxidant activity, total phenolic and flavonoids contents in Stachytarpheta cayennensis, (Rich.) Vahl. (Verbenaceae). J. Med. Plants Res., 2015, 9(17), 569-575.
[http://dx.doi.org/10.5897/JMPR2014.5751]
[3]
Bangou, M.J.; Méda, N.T.R.; Thiombiano, A.M.E.; Kiendrebéogo, M.; Zeba, B.; Millogo-Rasolodimby, J.; Nacoulma, O.G.; Coulidiaty, Y.D.; Yougbaré-Ziébrou, M. Antioxidant and antibacterial activities of five verbenaceae species from Burkina Faso. Curr. Res. J. Biol. Sci., 2012, 4(6), 665-672.
[4]
Khan, M.R.; Siddique, F. Antioxidant effects of Citharexylum spinosum in CCl4 induced nephrotoxicity in rat. Exp. Toxicol. Pathol., 2012, 64(4), 349-355.
[http://dx.doi.org/10.1016/j.etp.2010.09.009] [PMID: 21074979]
[5]
Soria, E.A.; Quiroga, P.L.; Albrecht, C.; Ramos Elizagaray, S.I.; Cantero, J.J.; Bongiovanni, G.A. Development of an antioxidant phytoextract of Lantana grisebachii with lymphoprotective activity against in vitro arsenic toxicity. Adv. Pharmacol. Sci., 2014, 2014, 416761-416767.
[http://dx.doi.org/10.1155/2014/416761] [PMID: 25002868]
[6]
Chantal, N.G.K.C.; Akhanovna, M.J.; Yvesalain, B. Effect of flavonoids of Gmelina arborea Roxb. (Verbenaceae) from Côte d’Ivoire on the antioxidant activity and osmotic. J. Appl. Biosci., 2016, 39, 2626-2634.
[7]
Kumar, S.; Sandhir, R.; Ojha, S. Evaluation of antioxidant activity and total phenol in different varieties of Lantana camara leaves. BMC Res. Notes, 2014, 7, 560-568.
[http://dx.doi.org/10.1186/1756-0500-7-560] [PMID: 25145266]
[8]
Tadesse, E.; Engidawork, E.; Nedi, T.; Mengistu, G. Evaluation of the anti-diarrheal activity of the aqueous stem extract of Lantana camara Linn (Verbenaceae) in mice. BMC Complement. Altern. Med., 2017, 17(1), 190-197.
[http://dx.doi.org/10.1186/s12906-017-1696-1] [PMID: 28376868]
[9]
Suleiman, M.M.; Yusuf, S. Antidiarrheal activity of the fruits of Vitex doniana in laboratory animals. Pharm. Biol., 2008, 46(6), 387-392.
[http://dx.doi.org/10.1080/13880200802055826]
[10]
Iwueke, A.V.; Nwodo, O.F.C.; Okoli, C.O. Evaluation of the antiinflammatory and analgesic activities of Vitex doniana leaves. Afr. J. Biotechnol., 2006, 5(20), 1929-1935.
[11]
Marcial, G.; Sendker, J.; Brandt, S.; de Lampasona, M.P.; Catalán, C.A.N.; de Valdez, G.F.; Hensel, A. Gastroprotection as an example: Antiadhesion against Helicobacter pylori, anti-inflammatory and antioxidant activities of aqueous extracts from the aerial parts of Lippia integrifolia Hieron. J. Ethnopharmacol., 2014, 155(2), 1125-1133.
[http://dx.doi.org/10.1016/j.jep.2014.06.039] [PMID: 24993887]
[12]
Morales, G.; Paredes, A.; Olivares, A.; Bravo, J. Acute oral toxicity and anti-inflammatory activity of hydroalcoholic extract from Lampaya medicinalis Phil in rats. Biol. Res., 2014, 47(1), 6-12.
[http://dx.doi.org/10.1186/0717-6287-47-6]
[13]
Kilimozhi, D.; Parthasarathy, V.; Jayanth, M.N.V.; Manavalan, R. Antinociceptive, antipyretic and anti-inflammatory effects of Clerodendrum phlomidis in mice and rats. Int. J. Biol. Chem. Sci., 2009, 3(3), 504-512.
[http://dx.doi.org/10.4314/ijbcs.v3i3.45343]
[14]
Zétola, M.; De Lima, T.C.M.; Sonaglio, D.; González-Ortega, G.; Limberger, R.P.; Petrovick, P.R.; Bassani, V.L. CNS activities of liquid and spray-dried extracts from Lippia alba-Verbenaceae (Brazilian false melissa). J. Ethnopharmacol., 2002, 82(2-3), 207-215.
[http://dx.doi.org/10.1016/S0378-8741(02)00187-3] [PMID: 12241997]
[15]
Roldão Ede.F.; Witaicenis, A.; Seito, L.N.; Hiruma-Lima, C.A.; Di Stasi, L.C. Evaluation of the antiulcerogenic and analgesic activities of Cordia verbenacea DC. (Boraginaceae). J. Ethnopharmacol., 2008, 119(1), 94-98.
[http://dx.doi.org/10.1016/j.jep.2008.06.001] [PMID: 18588967]
[16]
Okoye, T.C.; Akah, P.A.; Ezike, A.C.; Uzor, P.F.; Odoh, U.E.; Igboeme, S.O.; Onwuka, U.B.; Okafor, S.N. Immunomodulatory effects of Stachytarpheta cayennensis leaf extract and its synergistic effect with artesunate. BMC Complement. Altern. Med., 2014, 14, 376.
[http://dx.doi.org/10.1186/1472-6882-14-376] [PMID: 25283179]
[17]
Gonçalves, J.L.S.; Leitão, S.G.; Monache, F.D.; Miranda, M.M.; Santos, M.G.; Romanos, M.T.; Wigg, M.D. In vitro antiviral effect of flavonoid-rich extracts of Vitex polygama (Verbenaceae) against acyclovir-resistant herpes simplex virus type 1. Phytomedicine, 2001, 8(6), 477-480.
[http://dx.doi.org/10.1078/S0944-7113(04)70069-0] [PMID: 11824525]
[18]
Matias, E.F.F.; Alves, E.F.; do Nascimento Silva, M.K.; de Alencar Carvalho, V.R.; Medeiros, C.R.; dos Santos, F.A.V.; de Carvalho Nilo Bitu, V.; de Souza, C.E.S.; Figueredo, F.G.; Menezes, I.R.A.; Coutinho, H.D.M.; de Alencar Ferreira, J.V.; de Lima, L.F.; da Costa, J.G.M. Phytochemical characterization by HPLC and evaluation of antibacterial and aminoglycoside resistance-modifying activity of chloroform fractions of Cordia verbenacea DC leaf extracts. Eur. J. Integr. Med., 2015, 7, 251-257.
[http://dx.doi.org/10.1016/j.eujim.2015.03.007]
[19]
Prusti, A.; Mishra, S.R.; Sahoo, S.; Mishra, S.K. Antibacterial activity of some Indian medicinal plants. Ethnobot. Leaflets, 2008, 12, 227-230.
[20]
M. C. H Ibarrola, D. A.; Montalbetti, Y.; Kennedy, M. L. Heinichen, O.; Campuzano, M.; Ferro, E. A.; Alvarenga, N.; Tortoriello, J.; De Lima, T. C. M.; Mora, S. The antidepressant-like effects of Aloysia polystachya (Griseb.) Moldenke (Verbenaceae) in mice. Phytomedicine, 2008, 15, 478-483.
[http://dx.doi.org/10.1016/j.phymed.2007.11.018]
[21]
Hu, Z.; Xue, Y.; Yao, G.; Luo, Z.; Wang, Y.; Zhang, Y. Chemical constituents from the leaves of Premna microphylla Turcz. J. Chin. Pharm. Sci., 2013, 22(5), 431-434.
[http://dx.doi.org/10.5246/jcps.2013.05.063]
[22]
Chen, G.; Dai, C.; Wang, T.; Jiang, C.; Han, C.; Song, X. A new flavonol from the stem-bark of Premna fulva. Arkivoc, 2010, 2, 179-185.
[23]
Li, Q.; Shen, Y.M.; Li, P. Study oil flavanoids in the leaves of Premna szemaoensis Pei. Chung Kuo Yao Hsueh Tsa Chih, 2008, 43(6), 417-419.
[24]
Zheng, Z.Z.; Xu, S.Y.; Wang, D.Y. Chemical constituents in root of Premna microphylla. Yaredai Zhiwu Kexue, 2002, 31(3), 9-11.
[25]
Hu, Y.; Li, X.; Ma, N.; Zhang, X.; Mao, Y.; Chen, L.; Xiong, S.; Xue, C. Extraction, purification and antioxidant activity of total flavonoids from Premna microphylla Turcz leaves. Sci. Tech. Food Ind., 2016, 37(20), 268-273.
[26]
de Oliveira, F.C.; Barbosa, F.G.; Mafezoli, J.; de Oliveira, M.C.F.; Neto, M.A.; Guedes, M.L.S. Chemical constituents of Lippia rigida Schauer (Verbenaceae). Biochem. Syst. Ecol., 2013, 51, 328-330.
[http://dx.doi.org/10.1016/j.bse.2013.09.009]
[27]
Morales, G.; Paredes, A. Antioxidant activities of Lampaya medicinalis extracts and their main chemical constituents. BMC Complement. Altern. Med., 2014, 14, 259.
[http://dx.doi.org/10.1186/1472-6882-14-259] [PMID: 25047047]
[28]
Nagao, T.; Abe, F.; Kinjo, J.; Okabe, H. Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. Biol. Pharm. Bull., 2002, 25(7), 875-879.
[http://dx.doi.org/10.1248/bpb.25.875] [PMID: 12132661]
[29]
El-Hela, A.A.; Al-Amier, H.A.; Ibrahim, T.A. Comparative study of the flavonoids of some Verbena species cultivated in Egypt by using High-Performance Liquid Chromatography coupled with ultraviolet spectroscopy and atmospheric pressure chemical ionization mass spectrometry. J. Chromatogr. A, 2010, 1217(41), 6388-6393.
[http://dx.doi.org/10.1016/j.chroma.2010.08.025] [PMID: 20817165]
[30]
Ono, M.; Oda, E.; Tanaka, T.; Iida, Y.; Yamasaki, T.; Masuoka, C.; Ikeda, T.; Nohara, T. DPPH radical-scavenging effect on some constituents from the aerial parts of Lippia triphylla. J. Nat. Med., 2008, 62(1), 101-106.
[http://dx.doi.org/10.1007/s11418-007-0197-9] [PMID: 18404353]
[31]
Momeni, J.; Tsopmejio, J.P.; Nkouam, F.T.; Ngassoum, M.B. Antioxidant activity of the natural flavonoid 7-hydroxy-5,6,4′-trimethoxyflavone isolated from the leaves of Lippia rugosa A. Chev. Nat. Sci., 2016, 8, 70-78.
[32]
Leitão, S.G.; dos Santos, T.C.; Monache, F.D.; Matheus, M.E.; Fernandes, P.D.; Marinho, B.G. Phytochemical profile and analgesic evaluation of Vitex cymosa leaf extracts. Rev. Bras. Farmacogn., 2011, 21(5), 874-883.
[http://dx.doi.org/10.1590/S0102-695X2011005000160]
[33]
Rammohan, A.; Munikishore, R.; Gunasekar, D.; Blond, A.; Bodo, B. Two new chalcones from Clerodendrum phlomidis. J. Asian Nat. Prod. Res., 2015, 17(4), 343-347.
[http://dx.doi.org/10.1080/10286020.2014.968561] [PMID: 25315345]
[34]
Tu, Y.; Sun, L.; Guo, M.; Chen, W. The medicinal uses of Callicarpa L. in traditional Chinese medicine: An ethnopharmacological, phytochemical and pharmacological review. J. Ethnopharmacol., 2013, 146(2), 465-481.
[http://dx.doi.org/10.1016/j.jep.2012.12.051] [PMID: 23313870]
[35]
Raha, P.; Das, A.K.; Adityachaudhuri, N.; Majumder, P.L. Cleroinermin, aneo-clerodane diterpenoid from Clerodendron inermi. Phytochemistry, 1991, 30(11), 3812-3814.
[http://dx.doi.org/10.1016/0031-9422(91)80120-P]
[36]
Etti, S.; Shanmugam, G.; Ponnuswamy, M.N.; Balakrishna, K.; Vasanth, S. 5,3′-Dihydroxy- 3,7,4′,5′-tetramethoxy flavone. Acta Crystal. Section E, 2005, 61(4), o846-o848.
[http://dx.doi.org/10.1107/S1600536805006161]
[37]
Habtemariam, S.; Gray, A.I.; Waterman, P.G. Flavonoids from three Ethiopian species of Premna. Z. Naturforsch. B, 2014, 47(1), 144-147.
[http://dx.doi.org/10.1515/znb-1992-0125]
[38]
Anis, I.; Ahmed, S.; Malik, A.; Yasin, A.; Choudary, M.I. Enzyme inhibitory constituents from Duranta repens. Chem. Pharm. Bull. (Tokyo), 2002, 50(4), 515-518.
[http://dx.doi.org/10.1248/cpb.50.515] [PMID: 11964000]
[39]
Nwodo, N.; Okoye, F.; Lai, D.; Debbab, A.; Kaiser, M.; Brun, R.; Proksch, P. Evaluation of the in vitro trypanocidal activity of methylated flavonoid constituents of Vitex simplicifolia leaves. BMC Complement. Altern. Med., 2015, 15, 82-86.
[http://dx.doi.org/10.1186/s12906-015-0562-2] [PMID: 25886869]
[40]
Li, W.X.; Cui, C.B.; Cai, B.; Wang, H.Y.; Yao, X.S. Flavonoids from Vitex trifolia L. inhibit cell cycle progression at G2/M phase and induce apoptosis in mammalian cancer cells. J. Asian Nat. Prod. Res., 2005, 7(4), 615-626.
[http://dx.doi.org/10.1080/10286020310001625085] [PMID: 16087636]
[41]
Rudrapaul, P.; Sarma, I.S.; Das, N.; De, U.C.; Bhattacharjee, S.; Dinda, B. New flavonol methyl ether from the leaves of Vitex peduncularis exhibits potential inhibitory activity against Leishmania donovani through activation of iNOS expression. Eur. J. Med. Chem., 2014, 87, 328-335.
[http://dx.doi.org/10.1016/j.ejmech.2014.09.076] [PMID: 25264585]
[42]
Leitão, S.G.; Leitão, G.G.; Vicco, D.K.T.; Pereira, J.P.B.; de Morais Simão, G.; Oliveira, D.R.; Celano, R.; Campone, L.; Piccinelli, A.L.; Rastrelli, L. Counter-current chromatography with off-line detection by ultra high performance liquid chromatography/high resolution mass spectrometry in the study of the phenolic profile of Lippia origanoides. J. Chromatogr. A, 2017, 1520, 83-90.
[http://dx.doi.org/10.1016/j.chroma.2017.09.004] [PMID: 28939231]
[43]
Ijaz, F.; Ahmad, N.; Ahmad, I. ul Haq, A.; Wang, F. Two new anti-plasmodial flavonoid glycosides from Duranta repens. J. Enzyme Inhib. Med. Chem., 2010, 25(6), 773-778.
[http://dx.doi.org/10.3109/14756360903433365] [PMID: 20565340]
[44]
Yamasaki, T.; Kawabata, T.; Masuoka, C.; Kinjo, J.; Ikeda, T.; Nohara, T.; Ono, M. Two new lignan glucosides from the fruit of Vitex cannabifolia. J. Nat. Med., 2008, 62(1), 47-51.
[http://dx.doi.org/10.1007/s11418-007-0184-1] [PMID: 18404341]
[45]
Yu, H.; Hua, J.; Qing, L.; Xu, Q. Chemical constituents of Premna yunnanensis. Chin. Trad. Pat. Med., 2012, 34(2), 300-302.
[46]
Kawashty, S.A.; El-Garf, I.A. The flavonoid chemosystematics of Egyptian Verbena species. Biochem. Syst. Ecol., 2000, 28(9), 919-921.
[http://dx.doi.org/10.1016/S0305-1978(99)00114-3] [PMID: 10913856]
[47]
Stashenko, E.E.; Martínez, J.R.; Cala, M.P.; Durán, D.C.; Caballero, D. Chromatographic and mass spectrometric characterization of essential oils and extracts from Lippia (Verbenaceae) aromatic plants. J. Sep. Sci., 2013, 36(1), 192-202.
[http://dx.doi.org/10.1002/jssc.201200877] [PMID: 23292852]
[48]
de Almeida, M.C.S.; Alves, L.A.; da Souza, L.G.; Machado, L.L.; de Matos, M.C. de Oliveira e Telma L.G.; Lemos, M.C.F. Flavonoids and other substances from Lippia sidoides and their antioxidant activities. Quim. Nova, 2010, 33(9), 1877-1881.
[49]
Funari, C.S.; de Almeida, L.; Passalacqua, T.G.; Martinez, I.; Ambrosio, D.L.; Cicarelli, R.M.B.; Silva, D.H.S.; Graminha, M.A.S. Oleanonic acid from Lippia lupulina (Verbenaceae) shows strong in vitro antileishmanial and antitrypanosomal activity. Acta Amazon., 2016, 46(4), 411-416.
[http://dx.doi.org/10.1590/1809-4392201600204]
[50]
Zhong, C.; Wang, D. Four new isoflavones from Premna microphylla. Indian J. Heterocycl. Chem., 2002, 12, 143-148.
[51]
Asthana, J.; Yadav, D.; Pant, A.; Yadav, A.K.; Gupta, M.M.; Pandey, R. Acacetin 7-O-α-l-rhamnopyranosyl (1-2) β-D-xylopyrano-side elicits life-span extension and stress resistance in Caenorhabditis elegans. J. Gerontol. A Biol. Sci. Med. Sci., 2016, 71(9), 1160-1168.
[http://dx.doi.org/10.1093/gerona/glv173] [PMID: 26433219]
[52]
Ghosh, P.S.; Das, N.; Dinda, B. Antioxidant flavone glycosides and other constituents from Premna latifolia leaves. Indian J. Chem., 2014, 53B, 746-749.
[53]
Ono, M.; Chikuba, T.; Mishima, K.; Yamasaki, T.; Ikeda, T.; Yoshimitsu, H.; Nohara, T. A new diterpenoid and a new triterpenoid glucosyl ester from the leaves of Callicarpa japonica Thunb. var. luxurians Rehd. J. Nat. Med., 2009, 63(3), 318-322.
[http://dx.doi.org/10.1007/s11418-009-0316-x] [PMID: 19184273]
[54]
Timóteo, P.; Karioti, A.; Leitão, S.G.; Vincieri, F.F.; Bilia, A.R. A validated HPLC method for the analysis of herbal teas from three chemotypes of Brazilian Lippia alba. Food Chem., 2015, 175, 366-373.
[http://dx.doi.org/10.1016/j.foodchem.2014.11.129] [PMID: 25577093]
[55]
Iwashina, T.; Setoguchi, H.; Kitajima, J. Flavonoids from the Leaves of Vitex rotundifolia (Verbenaceae), and their qualitative and quantitative comparison between coastal and inland populations. Bull. Natl. Mus. Nat. Sci., 2011, 37, 87-94.
[56]
Park, S.; Son, M.J.; Yook, C.S.; Jin, C.; Lee, Y.S.; Kim, H.J. Chemical constituents from aerial parts of Caryopteris incana and cytoprotective effects in human HepG2 cells. Phytochemistry, 2014, 101, 83-90.
[http://dx.doi.org/10.1016/j.phytochem.2014.02.008] [PMID: 24582277]
[57]
El-Hawary, S.S.; Yousif, M.F.; Motaal, A.A.A.; Abd-Hameed, L.M. Bioactivities, phenolic compounds and in vitro propagation of Lippia citriodora Kunth cultivated in Egypt. Bull. Fac. Pharm. Cairo Univ., 2012, 50(1), 1-6.
[http://dx.doi.org/10.1016/j.bfopcu.2011.12.001]
[58]
Umber, R.E. The Flavonoid Chemistry of Glandularia bipinnatifida (Verbenaceae) and Allied Species. Am. J. Bot., 1980, 67(6), 935-941.
[http://dx.doi.org/10.1002/j.1537-2197.1980.tb07723.x]
[59]
Gallo, M.B.C.; Rocha, W.C.; da Cunha, U.S.; Diogo, F.A.; da Silva, F.C.; Vieira, P.C.; Vendramim, J.D.; Fernandes, J.B.; da Silva, M.F.; Batista-Pereira, L.G. Bioactivity of extracts and isolated compounds from Vitex polygama (Verbenaceae) and Siphoneugena densiflora (Myrtaceae) against Spodoptera frugiperda (Lepidoptera: Noctuidae). Pest Manag. Sci., 2006, 62(11), 1072-1081.
[http://dx.doi.org/10.1002/ps.1278] [PMID: 16953496]
[60]
Michael, H.N.; Salib, J.Y.; Ishak, M.S. New methoxyflavone glycosides from Verbena bipinnatifida Nutt. Pharmazie, 2001, 56(4), 348-349.
[PMID: 11338679]

Rights & Permissions Print Cite
Article Metrics
26
© 2024 Bentham Science Publishers | Privacy Policy