Skip to main content
. 2019 Nov 1;10:1234. doi: 10.3389/fphar.2019.01234

Table 2.

Secondary metabolites isolated from members of the genus Echinops.

No. Name of secondary metabolites Species Plant part Pharmacological activity Ref.
Thiophenes
1. 5-(but-3-en-1-ynyl)-2,2'-bithiophene E. macrochaetus R Abegaz et al., 1991
E. pappii Chiov. R Abegaz et al., 1991; Abegaz, 1991
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. ritro AP
E. latifolius R Wang et al., 2006
E. grijsii R Zhang and Ma, 2010; Chang et al., 2015
E. grijsii R Cytotoxic Jin et al., 2008
E. grijsii R Insecticidal Zhao et al., 2017
E. nanus Bunge R Nakano et al., 2012
E. albicaulis AP Kiyekbayeva et al., 2017
E. albicaulis WP Termicidal Fokialakis et al., 2006b
E. spinosissimus subsp. spinosissimus WP Termicidal Fokialakis et al., 2006b
2. α-terthiophene E. ellenbeckii R Abegaz et al., 1991
E. pappii R Abegaz et al., 1991
E. macrochaetus R
E. grijsii R Cytotoxic Jin et al., 2008
E. grijsii R Liu et al., 2002; Zhang and Ma, 2010; Chang et al., 2015
E. grijsii R Insecticidal Zhao et al., 2017
E. latifolius R Wang et al., 2006
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. ritro AP Termicidal Fokialakis et al., 2006b
E. nanus R Nakano et al., 2012
E. albicaulis R Kiyekbayeva et al., 2017
E. albicaulis WP Termicidal Fokialakis et al., 2006b
E. albicaulis WP Termicidal Fokialakis et al., 2006b
E. albicaulis WP Termicidal Fokialakis et al., 2006b
E. transiliensis R Insecticidal Nakano et al., 2014
3. 5-(penta-1,3-diynyl)-2-(3-chloro-4-hydoxy-but-1-ynyl)-thiophene E. ellenbeckii R Abegaz et al., 1991
E. giganteus R
E. hispidus Fresen. R
E. longisetus R
E. macrochaetus R
4. Cis or trans-2-(pent-3-en-1-ynyl)-5-(4-hydroxybut-1-ynyl)-thiophenes E. pappii R Abegaz, 1991
5. 5-(4-hydroxybut-1-ynyl)-2-(pent-1,3-diynyl)-thiophene E. pappii R Abegaz, 1991
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. ritro AP Termicidal Fokialakis et al., 2006b
E. grijsii R Chang et al., 2015
E. grijsii R Cytotoxic Zhang et al., 2009;
E. grijsii R NQO1-inducing Zhang and Ma, 2010
E. giganteus Rz Cytotoxic Kuete et al., 2013
E. giganteus Rz Cytotoxic Sandjo et al., 2016
6. 5-(penta-1,3-diynyl)-2-(but-3-en-1-ynyl)-thiophene E. ellenbeckii R Hymete et al., 2005b
7. 5-(penta-1,3-diynyl)-2-(4-acetoxy-but-1-ynyl)-thiophene E. ellenbeckii R Hymete et al., 2005b
8. 5-(penta-1,3-diynyl)-2-(3-hydroxy-4-acetoxy-but-1-ynyl)-thiophene E. ellenbeckii R Hymete et al., 2005b
E. hoehnelii R Bitew et al., 2017
E. transiliensis R Insecticidal Nakano et al., 2014
9. 5-(penta-1,3-diynyl)-2-(3,4-diacetoxy-but-1-ynyl)-thiophene E. ellenbeckii R Hymete et al., 2005a
E. grijsii R Jin et al., 2008
E. grijsii R NQO1-inducing Zhang and Ma, 2010
E. transiliensis R Insecticidal Nakano et al., 2014
10. 5-(penta-1,3-diynyl)-2-(3-chloro-4-acetoxy-but-1-ynyl)-thiophene E. ellenbeckii R Hymete et al., 2005b
E. transiliensis R Insecticidal Nakano et al., 2014
E. albicaulis WP Termicidal Fokialakis et al., 2006b
E. hoehnelii R Anti-malarial Bitew et al., 2017
11. 5-(penta-1,3-diynyl)-2-(3,4-epoxy-but-1-ynyl)-thiophene E. ellenbeckii R Hymete et al., 2005b
12. 5-[-(5-acetoxymethyl-2-trienyl)-2-(but-3-ene-1-ynyl)]-thiophene E. ellenbeckii R Hymete et al., 2005b
13. 5-(5,6-dihydroxy-hexa-1,3-diynyl)-2-(prop-1-ynyl)-thiophene (echinoynethiophene A) E. grijsii R Liu et al., 2002; Dong et al., 2008a
E. grijsii R Cytotoxic Zhang et al., 2009
14. 5-(penta-1,3-diynyl)-2-(3,4-dihydroxybut-1-ynyl)-thiophene E. grijsii R Liu et al., 2002; Dong et al., 2008a; Chang et al., 2015
E. ritro WP Li et al., 2019
E. grijsii R NQO1-inducing Shi et al., 2010; Zhang and Ma, 2010
E. grijsii R Cytotoxic Zhang et al., 2009
E. giganteus Rz Cytotoxic Sandjo et al., 2016
E. transiliensis R Insecticidal Nakano et al., 2014
E. hoehnelii R Anti-malarial Bitew et al., 2017
15. 5-(3,4-dihydroxybut-1-ynyl)-2,2′-bithiophene E. grijsii R Liu et al., 2002; Dong et al., 2008a; Zhang et al., 2009; Zhang and Ma, 2010; Chang et al., 2015
E. ritro WP Li et al., 2019
E. latifolius R Cytotoxic Wang et al., 2007
E. transiliensis R Insecticidal Nakano et al., 2014
16. 2,2'-bithiophene-5-carboxylic acid E. grijsii R Liu et al., 2002; Chang et al., 2015
E. ritro WP Li et al., 2019
17. 5-(3-buten-1-ynyl)-2,2'-bithiophene E. grijsii R Liu et al., 2002
18. 5-(4-isovaleroyloxybut-1-ynyl)-2,2'-bithiophene E. grijsii R Liu et al., 2002; Chang et al., 2015
E. grijsii R Wang et al., 2006
E. grijsii R Cytotoxic Jin et al., 2008
E. grijsii R Insecticidal Zhao et al., 2017
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. ritro AP Termicidal Fokialakis et al., 2006b
19. 5-chloro- α-terthiophene E. grijsii R Liu et al., 2002
20. 5-acetyl α-terthiophene E. grijsii R Liu et al., 2002
21. 5,5'-dichloro-α-terthiophene E. grijsii R Liu et al., 2002
22. Cardopatine E. grijsii R Liu et al., 2002; Chang et al., 2015
E. latifolius R Wang et al., 2006
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. ritro AP Termicidal Fokialakis et al., 2006b
23. Isocardopatine E. grijsii R Liu et al., 2002; Zhang and Ma, 2010; Chang et al., 2015
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. grijsii R Cytotoxic Jin et al., 2008
24. Grijisyne A E. grijsii R Zhang et al., 2008
25. Grijisone A E. grijsii R Zhang et al., 2008
26. 5-(4-hydroxy-3-methoxy-1-butyny)-2,2'-bithiophene E. grijsii R Chang et al., 2015
27. 5-acetyl-2,2'-bithiophene E. latifolius R Wang et al., 2008
E. grijsii R Chang et al., 2015
E. ritro WP Li et al., 2019
28. 5-formyl-2,2'-bithiophene E. grijsii R Chang et al., 2015
29. Methyl 2,2'-bithiophene-5-carboxylate E. grijsii R Chang et al., 2015
30. 5-(3-hydroxymethyl-3-isovaleroyloxyprop-1-ynyl)-2,2'-bithiophene E. latifolius R Wang et al., 2006
E. grijsii R Chang et al., 2015
31. 5-(4-hydroxy-1-butynyl)-2,2'-bithiophene E. latifolius R Wang et al., 2008
E. ritro Rd Antifungal Fokialakis et al., 2006a
E. latifolius R Cytotoxic Wang et al., 2007
E. grijsii R Zhang et al., 2009; Chang et al., 2015
E. ritro WP Antibacterial, Antifungal Li et al., 2019
E. ritro AP Termicidal Fokialakis et al., 2006b
32. 5-(4-acetoxy-1-butynl)-2,2'-bithiophene E. grijsii R Chang et al., 2015
33. 5-(3-hydroxy-4-isovaleroyloxybut-1-ynyl)-2,2'-bithiophene E. latifolius R Wang et al., 2006
34. 5-(3-acetoxy-4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene E. latifolius R Wang et al., 2006
E. grijsii R Cytotoxic Jin et al., 2008
35. Echinopsacetylenes A E. transiliensis R Nakano et al., 2011
36. Echinopsacetylenes B E. transiliensis R Nakano et al., 2011
37. Echinothiophenegenol E. grijsii R Zhang et al., 2009
E. nanus R Nakano et al., 2012
38. 5-(4-acetoxy-3-chlorobut-1-ynyl)-2-(pent-1,3-diynyl)-thiophene E. ritro Rd Antifungal Fokialakis et al., 2006a
39. 5-(3,4-diacetoxybut-1-ynyl)-2,2′-bithiophene E. ritro Rd Antifungal Fokialakis et al., 2006a
E. ritro AP Termicidal Fokialakis et al., 2006b
E. grijsii R Zhang and Ma, 2010
E. grijsii R Cytotoxic Jin et al., 2008
E. transiliensis R Insecticidal Nakano et al., 2014
40. 5-{4-[4-(5-pent-1,3-diynylthiophene-2-yl)-but-3-yny}-2,2'-bithiophene E. latifolius R Cytotoxic Wang et al., 2007
41. 5-(4-hydroxybut-1-one)-2,2'-bithiophene E. latifolius R Cytotoxic Wang et al., 2007
E. ritro WP Li et al., 2019
42. 5-(prop-1-ynyl)- 2-(3,4-diacetoxybut-1-ynyl)-thiophene E. latifolius R Wang et al., 2007
E. grijsii R Cytotoxic Jin et al., 2008
43. 5-(1,2-dihydroxy-ethyl)-2-(Z)-hept-5-ene-1,3-diynylthiophene E. latifolius R Anti-inflammatory Jin et al., 2016
44. 5-(1,2-dihydroxyethyl)-2-(E)-hept-5-ene-1,3-diynylthiophene E. latifolius R Anti-inflammatory Jin et al., 2016
45. 6-Methoxy-arctinol-b E. latifolius R Anti-inflammatory Jin et al., 2016
46. Arctinol-b E. grijsii R Zhang et al., 2009
E. latifolius R Anti-inflammatory Jin et al., 2016
E. ritro WP Antibacterial, Antifungal Li et al., 2019
47. Arctinol E. latifolius R Anti-inflammatory Jin et al., 2016
E. ritro WP Li et al., 2019
E. ritro WP Li et al., 2019
48. Methyl [5'-(1-propynyf)-2,2'-bithienyl-5-yl] carboxylate E. latifolius R Anti-inflammatory Jin et al., 2016
49. 5-(penta-1,3-diynyl)-2-(3-methoxy-4-hydroxy-but-1-ynyl)-thiophene E. hoehnelii R Bitew et al., 2017
50. 5-(penta-1,3-diynyl)-2-(3-methoxy-4-acetoxy-but-1-ynyl)-thiophene E. hoehnelii R Bitew et al., 2017
51. 5-(3-hydroxy-4-acetoxybut-1-ynyl)-2,2′-bithiophene E. transiliensis R Nakano et al., 2014
E. transiliensis R Insecticidal Nakano et al., 2014
52. 5-(penta-1,3-diynyl)-2-(3-acetoxy-4-hydroxy-but-1-ynyl)-thiophene E. transiliensis R Insecticidal Nakano et al., 2014
53. 5'-(3,4-dihydroxybut-1-yn-1-yl)-[2,2'-bithiophene]-5-carbaldehyde. E. ritro WP Li et al., 2019
54. 5'-(3,4-dihydroxybut-1-yn-1-yl)-[2,2'-bithiophene]-5-carboxylic acid E. ritro WP Antibacterial Li et al., 2019
55. 4-hydroxy-1-(5'-methyl-[2,2'-bithiophen]-5-yl)butan-1-one E. ritro WP Antibacterial, Antifungal Li et al., 2019
56. Junipic acid E. ritro WP Li et al., 2019
57. Arctinal E. ritro WP Antibacterial Li et al., 2019
58. 4-(5'-methyl-[2,2'-bithiophen]-5-yl)but-3-yn-1-ol E. ritro WP Li et al., 2019
59. Arctinol A E. ritro WP Antibacterial Li et al., 2019
Terpenes
60. Dehydrocostus lactone E. amplexicauli R Abegaz et al., 1991
E. kebericho
61. Costunolide E. amplexicaulis, Abegaz et al., 1991,Abegaz, 1991
E. kebericho,
E. pappii
62. Dihydrocostunolide E. amplexicaulis R Abegaz et al., 1991
63. Echinopines A E. spinosus R Dong et al., 2008b
64. Echinopines B E. spinosus R Dong et al., 2008b
Terpenes
65. (3α,4α,6α)-3,13-dihydroxyguaia-7(11),10(14)-dieno-12,6-lactone) E. ritro WP Li et al., 2010
66. (3α,4α,6α,11ß)-3-hydroxyguai-1(10)-eno-12,6-lactone) E. ritro WP Li et al., 2010
67. (11α)-11,13-dihydroarglanilic acid methyl ester E. ritro WP Li et al., 2010
68. Vulgarin E. ritro WP Li et al., 2010
69. (3R,3aS,6aR,9S,9aR,9bS)-octahydro-3,9-dimethyl-6-methyleneazuleno[4,5-b]furan2,8(3H,9bH)-d ione E. ritro WP Li et al., 2010
70. (3aS,6aR,8S,9S,9aR,9bR)-decahydro-8-hydroxy-9-methyl-3,6 dimethyleneazuleno[4,5-b]furan-2(9bH)-one E. ritro WP Li et al., 2010
71. (3aS,6aR,8R,9R,9aR,9bR)-decahydro-8-hydroxy-3,3,9-trimethyl-6-methyleneazuleno[4,5-b]furan-2(9bH)-one E. ritro WP Li et al., 2010
72. (3R,3aS,6aR,8S,9S,9aR,9bS)-decahydro-8-hydroxy-3,9-dimethyl-6-methyleneazuleno[4,5-b]furan-2(9bH)-one E. ritro WP Li et al., 2010
73. Santamarin E. pappii Abegaz, 1991
E. ritro WP Li et al., 2010
74. Reynosin E. pappii R Abegaz, 1991
75. Caryophyllene epoxide E. giganteus R Abegaz et al., 1991
E. hispidus
76. Echusoside E. hussoni Boiss. AP Ka, 2001
77. (3S,3aS,5aR,6R,8R,9bS)-decahydro-6,8-dihydroxy-3,5a-dimethyl-9-methylenenaphtho[1,2-b]furan-2(9bH)-one E. ritro WP Li et al., 2010
78. (3S,3aS,5aR,6S,9bS)-3,3a,4,5,5a,6-hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,7(9aH,9bH)-dione E. ritro WP Li et al., 2010
79. 2,6,10-trimethyldodeca-2,6,10-triene E. albicaulis AP Kiyekbayeva et al., 2017
80. Macrochaetosides A E. macrochaetus AP Cytotoxic Zamzami et al., 2019
81. Macrochaetosides B E. macrochaetus AP Cytotoxic Zamzami et al., 2019
82. Latifolanone A E. latifolius R Jin et al., 2016
83. Atractylenolide-II E. latifolius R Anti-inflammatory Jin et al., 2016
84. ß-amyrin E. niveus WP Singh et al., 1990
85. Betulinic acid E. niveus WP
86. Lupeol E. niveus WP Singh et al., 1990
E. giganteus R Tene et al., 2004
E. integrifolius WP Senejoux et al., 2013
E. echinatus R Patel, 2016
87. Taraxasterol E. niveus WP Singh et al., 1990
88. Taraxasterol acetate E. niveus WP Singh et al., 1990
E. echinatus WP Anti-inflammatory Singh et al., 1989
89. ß-sitosterol E. niveus WP Singh et al., 1990
E. transiliensis R Nakano et al., 2012
E. giganteus Rz Kuete et al., 2013
E. orientalis Sd Antioxidant Erenler et al., 2014
90. ß-sitosterol glucoside E. niveus WP Singh et al., 1990
E. giganteus R Tene et al., 2004
E. integrifolius WP Senejoux et al., 2013
E. albicaulis AP Kiyekbayeva et al., 2017
91. Reynosin E. pappii R Abegaz, 1991
92. Gmeliniin A E. gmelinii AP He et al., 2000
93. Stigmasterol E. transiliensis R Nakano et al., 2012
E. macrochaetus AP Zamzami et al., 2019
E. integrifolius WP Senejoux et al., 2013
E. giganteus Rz Kuete et al., 2013
94. Lupeol acetate E. integrifolius WP Senejoux et al., 2013
E. echinatus R Patel, 2016
E. albicaulis AP Kiyekbayeva et al., 2017
95. Lupeol linoleate E. albicaulis AP Kiyekbayeva et al., 2017
96. Ajugasterone C E. grijisii R Dong et al., 2008a
97. Ursolic acid E. giganteus Rz Cytotoxic Kuete et al., 2013
98. Echinopsolide A (3ß-acetoxy-15α-bromoolean-13ß,28-olide) E. giganteus Rz Cytotoxic Sandjo et al., 2016
99. ß-amyrin acetate E. giganteus Rz Sandjo et al., 2016
100. 3ß-acetoxy-taraxast-12,20(30)-diene-11α-21α-diol E. galalensis AP Hepato-protective Abdallah et al., 2013
101. α-amyrin E. galalensis Rz Hepato-protective
102. Erythrodiol E. galalensis Rz Hepato-protective
Terpenes
103. Lup-20(29)-ene-1,3-diol E. galalensis Rz Hepato-protective
104. Cyclostenol E. macrochaetus AP Cytotoxic Zamzami et al., 2019
Flavonoids and other phenolic compounds
105. Apigenin E. niveus WP Singh et al., 1990
E. echinatus Ram et al., 1995
E. integrifolius AP Senejoux et al., 2013
E. spinosus AP Boumaraf et al., 2016
E. albicaulis AP Kiyekbayeva et al., 2017
106. Luteolin E. niveus WP Singh et al., 1990
E. grijisii R Dong et al., 2008a
107. Nivegin E. niveus WP Singh et al., 1990
108. Nivetin E. niveus AP Singh and Pandey, 1990
109. Apigenin 7-O-glucoside E. echinatus F Ram et al., 1995
E. spinosus AP Boumaraf et al., 2016
E. orientalis Sd Antioxidant Erenler et al., 2014
110. Echitin E. echinatus F Ram et al., 1995
111. Echinoside E. echinatus WP Singh et al., 2006
112. 7-hydroxyisoflavone E. echinatus WP Singh et al., 2006
113. Kaempferol E. echinatus WP Singh et al., 2006
114. Kaempferol-4'-methylether E. echinatus WP Singh et al., 2006
115. Kaempferol-7-methylether E. echinatus WP Singh et al., 2006
116. Kaempferol-3-O-α-L-rhamnoside E. echinatus WP Singh et al., 2006
E. heterophyllus AP Mahmood and Khadeem, 2013
117. Myrecetin-3-O-α-L-rhamnoside E. echinatus WP Singh et al., 2006
118. Chrysoeriol E. integrifolius WP Senejoux et al., 2013
119. Hispidulin E. integrifolius WP Senejoux et al., 2013
120. Jaceidin E. integrifolius WP Senejoux et al., 2013
121. Centaureidin E. integrifolius WP Senejoux et al., 2013
122. Axillarin E. integrifolius WP Senejoux et al., 2013
123. Genkwanin E. albicaulis AP Kiyekbayeva et al., 2017
124. Apigenin-7-O-(6"-trans-pcoumaroyl- ß -D-glucopyranoside E. orientalis L Antioxidant Erenler et al., 2014
E. spinosus AP Boumaraf et al., 2016
125. 5,7-dihydroxy-8,4'-dimethoxyflavanone-5-O-α-L-rhamno-pyranosyl-7-O-ß-D-arabinopyranosyl (1→4)-O-ß-D-glucopyranoside E. echinatus WP Anti-inflammatory Yadava and Singh, 2006
126. Candidone E. giganteus Rz Cytotoxic Kuete et al., 2013
127. Chlorogenic acid E. grijisii R Dong et al., 2008a
128. Cynarin E. grijisii R Dong et al., 2008a
129. Rutin E. heterophyllus AP Mahmood and Khadeem, 2013
E. albicaulis AP Kiyekbayeva et al., 2017
130. (+)-4-(3-methylbutanoyl)-2,6-di(3,4-dimethoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane E. giganteus R Tene et al., 2004
131. (+)-4-hydroxy-2,6- di(3,4-dimethoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane E. giganteus R Tene et al., 2004
E. giganteus Rz Sandjo et al., 2016
E. giganteus Rz Cytotoxic Kuete et al., 2013
132. Hexacosyl-(E)-ferulate E. nanus R Nakano et al., 2012
133. Umbelliferone E. integrifolius WP Senejoux et al., 2013
134. Syringin E. grijisii R Dong et al., 2008a
135. 1,5-dicaffeoylquinic acid E. galalensis AP Hepato-protective Abdallah et al., 2013
136. 3,5-dicaffeoylquinic acid Hepato-protective
137. 3,4-dicaffeoylquinic acid Hepato-protective
138. 4,5-dicaffeoylquinic acid Hepato-protective
Alkaloids
139. Echinopsine (1-methyl-4-quinolone) E. echinatus AP Chaudhuri, 1987
E. nanus R Nakano et al., 2012
E. albicaulis AP Kiyekbayeva et al., 2017
E. orientalis Sd Antioxidant Erenler et al., 2014
140. Echinozolinone E. echinatus AP Chaudhuri, 1987
Alkaloids
141. Echinopsidine E. echinatus AP Chaudhuri, 1987
142. 7-hydroxyechinozolinone E. echinatus F Chaudhuri, 1992
143. 1-Methyl-4(1H)-quinolinone E. heterophyllus Sd Khadim et al., 2014
144. 1-methyl-4-methoxy-8-(ß-D-glucopyranosyloxy)-2(1H)-quinolinone E. gmelinii Turcz. AP Su et al., 2004
145. 4-methoxy-8-(-D-glucopyranosyloxy)-2(1H)-quinolinone E. gmelinii AP Su et al., 2004
146. Echinorine E. albicaulis AP Kiyekbayeva et al., 2017
Lipids
147. Triacontane E. integrifolius R Karimov and Aisa, 2013
148. Heptacosane E. integrifolius R Karimov and Aisa, 2013
149. Lignoceric acid E. integrifolius R Karimov and Aisa, 2013
150. Tetrahydrofurano-ceramide E. giganteus Rz Cytotoxic Sandjo et al., 2016
151. Ritroyne A E. ritro R Li et al., 2019

AP, Aerial part; F, Flower; L, Leaf; R, Root; Rd, Radix; Rz, Rhizome; Sd, Seed; WP, Whole plant.