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BY 4.0 license Open Access Published by De Gruyter July 21, 2022

Chemical constituents of plants from the genus Carpesium

  • Ning-Ning Shi , Cong-Cong Hou , Yan Liu , Kun-Yao Li , Sheng-Dan Mi , Bin-Liang Tong and Man-Li Zhang EMAIL logo
From the journal Heterocyclic Communications
https://doi.org/10.1515/hc-2022-0012
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Abstract

Carpesium (Family – Compositae) is a genus with 24 species of mainly perennial herbs. Several species of this genus have served as folk medicine in China and Korea for their antipyretic, anti-inflammatory, analgesic, antifungal, antibacterial, and cytotoxic activity properties. Chemical constituents are mostly sesquiterpenes, diterpenes, glycosides, and several other types of compounds. This article summarizes the literature on the isolated and identified constituents from various Carpesium species and their various biological activities.

Keywords: chemical constituents; Carpesium ; structure; biological activities

1 Introduction

The genus Carpesium belongs to the tribe Compositae and comprises 24 species distributed in Asia and Eurasia. Among them, 18 species are widespread in China, mainly in the southwestern mountainous regions. The seed, roots, leaves, and stems of some Carpesium species have long been used as Chinese traditional medicine for hemostatic, vermifuge, anti-inflammatory, and detoxication. Moreover, research has shown that Carpesium plants yielded structurally diverse compounds, including sesquiterpenes, monoterpenes, diterpenoids, phenolic compounds, etc. Sesquiterpene lactones are considered as the characteristic constituents of this genus, and these could be a promising bio-resource for the development of potential drugs and value-added products.

In this review, we summarize the latest and comprehensive information on the application of Carpesium plants in traditional medicine, phytochemistry, pharmacology, and toxicology, to reveal the potential therapeutic effects of Carpesium plants and establish a solid foundation for directing future research. Herein we reviewed the works published up to August 2021.

1.1 Chemical constituents

The chemical constituents of Carpesium genus include sesquiterpenes, diterpenoids, steroids, and others. Their structures are shown in Figure 1, and names and corresponding plant sources are listed in Table 1. Sesquiterpenoids are the predominant constituents within the Carpesium compounds reported here.

Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1 The chemical structures of constituents from the Genus Carpesium.
Figure 1

The chemical structures of constituents from the Genus Carpesium.

Table 1

Chemical constituents from the genus Carpesium

No. Compound class and name Source Ref.
Germacranolides
1 Ivaxillin C. abrotanoides [1]
2 11(13)-Dehydroivaxillin C. abrotanoides [1]
3 Eriolin C. abrotanoides [1]
4 11,13-Didehydroivaxillin C. abrotanoides [2]
5 Carabrolactone A C. abrotanoides [3]
6 6,10-Dimethyl-2,9-dioxo-3α,4,4′,5,5′,6,7,8,9,10,11,11α-dodecahydro-2H-spiro[cyclodeca[b]furan-3,3′-pyrazol]-5-yl (E)-2-methylbut-2-enoate C. lipskyi [4]
7 (Z)-9-Acetoxy-6,10-dimethyl-2-oxo-3α,4,4′,5,5′,6,7,8,9,11α-decahydro-2H-spiro[cyclodeca[b]furan-3,3′-pyrazol]-5-yl (E)-2-methylbut-2-enoate C. lipskyi [5]
8 Carpelipine A C. lipskyi [5]
9 Carpelipine B C. lipskyi [5]
10 Carlipsine A C. lipskyi [6]
11 Carlipsine B C. lipskyi [6]
12 Carlipsine C C. lipskyi [6]
13 Carlipsine D C. lipskyi [6]
14 Carlipsine E C. lipskyi [6]
15 Carlipsine F C. lipskyi [6]
16 Carlipsine G C. lipskyi [6]
17 Carlipsine H C. lipskyi [6]
18 Carlipsine I C. lipskyi [6]
19 Carlipsine J C. lipskyi [6]
20 2β,5-Epoxy-5,10-Dihydroxy-6α,9β-Diangeloyloxy-Germacran-8α,12-Olide C. rosulatum [7]
21 2α,5-Epoxy-5,10-dihydroxy-6α-angeloyloxy-9β-isobutyloxy-germacran-8α,12-olide C. triste [8]
22 2α,5-Epoxy-5,10-dihydroxy-6α,9β-diangeloyloxy-germacran-8α,12-olide C. triste [8]
23 2α,5-Epoxy-5,10-dihydroxy-6α-angeloyloxy-9β-(2-methylbutyloxy)-germacran-8α,12-olide C. triste [8]
24 2α,5-Epoxy-5,10-dihydroxy-6α-angeloyloxy-9β-(3-methylbutanoyloxy)-germacran-8α,12-olide C. triste [8]
25 2β,5-Epoxy-5,10-dihydroxy-6α-angeloyloxy-9β-isobutyloxy-germacran-8α,12-olide C. divaricatum [9]
26 4β,8α-Dihydroxy-5β-2-methylbutyryloxy-9β-3-methylbutyryloxy-3-oxo-germacran-7β,12α-olide C. triste [10]
27 4β,8α-Dihydroxy-5β-isobutyryloxy-9β-3-methylbutyryloxy-3-oxo-germacran-7β,12α-olide C. triste [10]
28 4β,9β-Dihydroxy-5β,8α-di(isobutyryloxy)-3-oxo-germacran-7β,12α-olide C. triste [10]
29 8α-Angeloyloxy-4β-hydroxy-5β-isobutyryloxy-9-oxo-germacran-7β,12α-olide C. triste [10]
30 Incaspitolide A C. triste [10]
31 Incaspitolide B C. triste [10]
32 8α-Isobutyryloxy-ineupatorolide B C. triste [10]
33 Epoxyineupatorolide B C. triste [10]
34 Incaspitolide D C. triste [10]
35 Divaricin A C. divaricatum [11]
36 Divaricin B C. divaricatum [11]
37 Divaricin C C. divaricatum [11]
38 Cardivin A C. divaricatum [13]
39 Cardivin B C. divaricatum [13]
40 Cardivin C C. divaricatum [13]
41 Cardivin D C. divaricatum [13]
42 Divarolide A C. divaricatum [14]
43 Divarolide B C. divaricatum [14]
44 Divarolide C C. divaricatum [14]
45 Divarolide D C. divaricatum [14]
46 Incaspitolide B1 C. divaricatum [14]
47 Incaspitolide B2 C. divaricatum [14]
48 (4S, 5R, 6S, 7S, 8R, 10R)-8-angeloyloxy-4-hydroxy-5-isobutyryloxy-9-oxo-germacran-7, 12-olide C. divaricatum [14]
49 Ineupatorolide C C. divaricatum [15]
50 4β,8α-dihydroxy-5β-angeloyloxy-9β-2-methylbutyryloxy-3-oxo-germacran-6α,12-olide C. divaricatum [16]
51 Divarolide E C. divaricatum [17]
52 Divarolide F C. divaricatum [17]
53 Divarolide G C. divaricatum [17]
54 8-isodivarolide C C. divaricatum [18]
55 Cardivarolide H C. divaricatum [18]
56 Cardivarolide I C. divaricatum [18]
57 Cardivarolide J C. divaricatum [18]
58 Cardivarolide K C. divaricatum [18]
59 Cardivarolide L C. divaricatum [18]
60 Ineupatorolide A C. glossophyllum [12]
61 Ineupatorolide B C. glossophyllum [12]
62 Nepalolides A C. nepalense [19]
63 Nepalolides B C. nepalense [19]
64 Nepalolides C C. nepalense [19]
65 Nepalolides D C. nepalense [19]
66 Carcerlane A C. nepalense [20]
67 Cernuumolide A C. cernuum [21]
68 Cernuumolide B C. cernuum [21]
69 Cernuumolide C C. cernuum [21]
70 Cernuumolide D C. cernuum [21]
71 Cernuumolide E C. cernuum [21]
72 Cernuumolide F C. cernuum [21]
73 Cernuumolide G C. cernuum [21]
74 Cernuumolide H C. cernuum [21]
75 Cernuumolide I C. cernuum [21]
76 Cernuumolide J C. cernuum [21]
77 Carpescernolide A C. cernuum [22]
78 Carpescernolide B C. cernuum [22]
79 Carpehumine A C. humile [23]
80 Carpehumine B C. humile [23]
81 Carpabrotalactone A C. abrotanoides [24]
Eudesmanolides
82 Granilin C. abrotanoides [25]
83 Granilin acetate C. abrotanoides [25]
84 (3aR,4aS,6R,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylene-2-oxododecahydronaphtho[2,3-b] furan-6-ylacetate C. abrotanoides [25]
85 11α,13-Dihydrotelekin C. abrotanoides [26]
86 5α-Hydroxy-4α,15-epoxy-11αH-eudesman-12,8β-olide C. abrotanoides [27]
87 Carpabrotalactone C C. abrotanoides [28]
88 (5α)-5-Hydroxyasperilin C. abrotanoides [24]
89 Carpabrotalactone B C. abrotanoides [24]
90 11,13-Dihydroisoalantolactone C. divaricatum [29]
91 11α,13-Dihydropinnatifidin C. divaricatum [29]
92 Pinnatifidin C. divaricatum [29]
93 1-Oxoeudesm-11(13)-eno-12,8a-lactone C. divaricatum [29]
94 5α,6α-Epoxyeudesman-12,8β-lactone C. divaricatum [29]
95 5α-Hydroxy-13-methoxy-7αH,11αH-eudesm-4(15)-en-12,8β-lactone C. divaricatum [29]
96 1β-Hydroxy-7αH,11αH-eudesm-4(15)-en-12,8β-lactone C. divaricatum [29]
97 11αH-Eudesman-4(15)-en-12,8β-olide C. divaricatum [30]
98 2α-Acetoxy-5α-hydroxy-11αH-eudesma-4(15)-en-12,8β-olide C. macrocephalum [31]
99 2α,5α-Dihydroxy-11αH-eudesma-4(15)-en-12,8β-olide C. macrocephalum [31]
100 11α,13-Dihydroivalin C. macrocephalum [31]
101 5α-Eudesma-4(15), 11(13)-dien-12,8β-olide C. macrocephalum [31]
102 5α,11αH-Eudesma-4(15)-en-12,8β-olide [31]
103 2α- O -β-d-Glucopyranosyl-5α,11αH-eudesma-4(15)-en-12,8β-olide C. macrocephalum [31]
104 2α-O-β-d-Glucopyranosyl-5αH-eudesma-4(15),11(13) dien-12,8-olide C. macrocephalum [31]
105 2a-Acetoxy-11aH-eudesma-4-en-12,8b-olide C. macrocephalum [32]
106 5α,6α-Dihydroxy-4α,11αH-eudesma-12,8β-olide C. macrocephalum [32]
107 5α-Epoxyalantolactone C. macrocephalum [33]
108 13-Hydroxy-4αH-eudesman-5,7(11)-dien-12,8β-olide C. cernuum [34]
109 13-Hydroxy-5,7(11)-eudesmadien-12,8-olide C. cernuum [35]
110 2α-Hydroxy-eudesman-4(15)-en-12,8β-olide C. cernuum [36]
111 4(15)-β-Epoxyisotelekin C. cernuum [37]
112 Isoalantolactone C. cernuum [37]
113 Ivalin C. cernuum [37]
114 6β-Hydroxy-8α-ethoxyeremophil-7(11)-en-12,8β-olide C. cernuum [37]
115 Alantolactone C. cernuum [37]
116 11(13)-Dihydroalantolactone [37]
117 Carpesin C. eximium [38]
118 Telekine C. eximium [38]
119 6,8-Dihydroxy-8α-methyl-3,5-dimethyl-idenedecahydronaphtho[2,3-b] furan-2(3H)-one C. triste [39]
120 1-Oxo-11αH-eudesma-2,4(14)-dien-12,8β-olide C. triste [40]
121 1α,3α-Dihydroxy-5,7,8,11αH-eudesm-4(15)-en-8β,12-olide C. triste [41]
122 2α-Hydroxy-5αH-eudesm-4(15),11(13)-dien-8β,12-olide C. minus [42]
123 3-Epi-isotelekin C. fructus [43]
Guaianolides
124 7-Hydroxy-3,6,9-trimethyldecahydroazuleno[4,5-b] furan-2(3H)-one C. abrotanoides [44]
125 Carpesialactone C. abrotanoides [45]
126 Vetivazulen C. abrotanoides [45]
127 Ethyl(E)-2-(4-acetoxy-3,8-dimethyloctahydroazulen-5(1H)-ylidene) acetate C. abrotanoides [46]
128 Ethyl 2-(4-acetoxy-5-hydroxy-3,8-dimethyldecahydroazulen-5-yl) propanoate C. abrotanoides [46]
129 3,6,9-Trimethyldecahydroazuleno[4,5-b] furan-2(3H)-one C. abrotanoides [46]
130 Ethyl (E)-2-(3,8-dimethyloctahydroazulen-5(1H)-ylidene) propanoate C. abrotanoides [46]
131 (3S,3aS,6S,6aS,9S,9aS,9bS)-3,6,9-Trimethyldecahydroazuleno[4,5-b] furan-2,7-dione C. abrotanoides [47]
132 3,6,9-Trimethyl-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b] furan-2,7-dione C. abrotanoides [47]
133 (3aS,4R,4aS,7aR,8S,9aR)-4a,8-Dimethyl-3-methylene-2,5-dioxododecahydroazuleno[6,5-b] furan-4-yl acetate C. abrotanoides [47]
134 (3aS,4S,4aR,7aS,8R,9aS)-4-Hydroxy-4a,8-dimethyl-3-methylenedecahydroazuleno[6,5-b] furan-2,5-dione C. abrotanoides [48]
135 4α,5α-Epoxy-10α,14-dihydro-inuviscolide C. abrotanoides [2]
136 4-Epi-Isoinuviscolide C. abrotanoides [3]
137 9β-Hydroxy-1βH,11αH-guaia-4,10(14)-dien-12,8α-olide C. abrotanoides [49]
138 9β-Hydroxy-1βH,11βH-guaia-4,10(14)-dien-12,8α-olide C. abrotanoides [49]
139 Caroguaianolide A C. abrotanoides [50]
140 Caroguaianolide B C. abrotanoides [50]
141 Caroguaianolide C C. abrotanoides [50]
142 Caroguaianolide D C. abrotanoides [50]
143 Caroguaianolide E C. abrotanoides [50]
144 Akihalin C. abrotanoides [50]
145 4β-Hydroxy,10β-hydroperoxyl,5αH,7αH,8βH-guaia-1,11(13)-dien-8α,12-olide C. abrotanoides [50]
146 4α-Hydroxy-9β,10β-epoxy-1βH,5αH-guaia-11(13)-en-8α,12-olide C. abrotanoides [50]
147 4α-Hydroxy-1βH-guaia-9,11(13)-dien-12,8α-olide C. abrotanoides [50]
148 (3aR,4a-S,5S,7aS,8S,9aR)-5-hydroxy-4a,8-dimethyl-3-methylene-decahydro-azuleno[6,5-b] furan-2(3H)-one C. abrotanoides [50]
149 Inuviscolide C. abrotanoides [50]
150 4β,10β-Dihydroxy-1αH,5αH,11αH-guaian-12,8β-olide C. cernuum [37]
151 4β,10β-Dihydroxy-1αH,5αH-guai-11(13)-en-12,8α-olide C. cernuum [37]
152 4α,5α-Epoxy-10αH,1-epi-inuviscolide C. cernuum [37]
153 1-Epi-inuviscolide C. cernuum [37]
154 4α,10α-dihydroxy-1βH,5βH-guai-11(13)-en-12,8α-olide C. cernuum [37]
155 (4aR,5S,7aR,8S,9aS)-5,8-Dihydroxy-5,8-dimethyl-3-methylenedecahydroazuleno[6,5-b] furan-2(3H)-one C. cernuum [37]
156 4α,5α-Dihydroxy-guaia-11(13)-en-12,8α-lactone C. divaricatum [29]
157 5β-Hydroxy-10α,14H-4-epi-inuviscolide C. divaricatum [30]
158 9β,10β-Epoxy-4α-hydroxy-1βH,11αH-guaian-12,8α-olide C. triste [40]
159 9β,10β-Epoxy-4α-hydroxy-1βH,11βH-guaian-12,8β-olide C. triste [40]
160 4α,9α-Dihydroxy-1βH,11αH-guai-10(14)-en-12,8α-olide C. triste [40]
161 4α,9α-Dihydroxy-1βH,11βH-guai-10(14)-en-12,8α-olide C. triste [40]
162 4β,10β-dihydroxy-5α(H)-1,11(13)-guaidien-8α,12-olide C. macrocephalum [51]
163 4β,10α-Dihydroxy-guaia-8α,12-olide C. rosulatum [7]
164 4β,10α-Dihydroxy-1(2),11 (13)-guaiadien-8α,12-olide C. rosulatum [7]
165 3β,8β-Dihydroxy-1α,5α-guaian-10(14)-ene-6α C. rosulatum [7]
166 11β,13-Dihydro-1-epi-inuviscolide C. fructus [43]
167 4β,10α-Dihydroxy-5α(H)-1,11(13)-guaidien-8α,12-olide C. faberi [52]
168 4α,10β-Dihydroxy-5α(H)-1,11(13)-guaidien-8β,12-olide C. faberi [52]
169 2′-Hydroxy-4′,6′-dimethoxy-benzoylcarpesiolin C. lipskyi [53]
　 Pseudoguaianes 　
170 2,3-Dihydroaromomaticin C. abrotanoides [2]
171 Carpesiolin C. abrotanoides [2]
172 Carabrolactone B C. abrotanoides [3]
173 2-Desoxy-4-epi-pulchellin C. abrotanoides [3]
174 Pesudoguaian-1α(H)-8α,12-olide-4β-O-β-d-glucropyranoside C. faberi [52]
175 (3aR,4aS,5S,7aS,8S,9aR)-5-Hydroxy-4a,8-dimethyl-3-methylen-decahydroazuleno[6,5-b] furan-2(3H)-on C. abrotanoides [50]
176 8-Epi-Confertin C. cernuum [37]
177 Confertin C. cernuum [37]
178 4β-Acetoxy-11(13)-pseudoguaien-12,8α-olide C. minus [42]
　 Carabranolides 　
179 2-(2-(2,4-Dinitrophenyl) hydrazineylidene)-3,5a-dimethyloctahydro-2H-cyclopropa[f]benzofuran-5-carbaldehyde C. abrotanoides [54]
180 4-(2-(2-(2,4-Dinitrophenyl) hydrazineylidene)-3,5a-dimethyl-4,4a,5,5a,6,6a-hexahydro-2H-cyclopropa[f]benzofuran-4-yl) butan-2-one C. abrotanoides [54]
181 (E)-5-(3-(2-(2,4-dinitrophenyl) hydrazineylidene) butyl)-3,5a-dimethyl-4,4a,5,5a,6,6a-hexahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
182 (E)-5-((2-(2,4-dinitrophenyl) hydrazineylidene) methyl)-3,5a-dimethyloctahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
183 (E)-5-(2-(2-(2,4-dinitrophenyl) hydrazineylidene) ethyl)-3,5a-dimethyloctahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
184 (3aR,4aS,5aR,6aR)-5-((E)-3-(2-(2,4-dinitrophenyl) hydrazineylidene) butyl)-5a-methyl-3-methyleneoctahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
185 3,5a-Dimethyl-5-(3-oxobutyl)-4,4a,5,5a,6,6a-hexahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
186 5-(2-(Dimethylamino) ethyl)-3,5a-dimethyloctahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
187 5-(2-Hydroxyethyl)-3,5a-dimethyloctahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
188 2-(3,5a-Dimethyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-yl) acetaldehyde C. abrotanoides [54]
189 3,5a-Dimethyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carbaldehyde C. abrotanoides [54]
190 3,5a-Dimethyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carboxylic acid C. abrotanoides [54]
191 3,5a-Dimethyl-5-vinyloctahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
192 3,5a-Dimethyl-4-(3-oxobutyl)-4,4a,5,5a,6,6a-hexahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [54]
193 (3aS,4aR,5R,5aS,6aS)-5a-methyl-5-(2-(2-methyl-1,3-dioxolan-2-yl) ethyl) octahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [55]
194 Ethyl (3aR,4aR,5R,5aS,6aS)-4a-methyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carboxylate C. abrotanoides [55]
195 S-ethyl (3aS,4aR,5R,5aR,6aR)-5a-methyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carbothioate C. abrotanoides [55]
196 (3aS,4aR,5R,5aS,6aR)-5a-methyl-5-(3-oxobutyl) octahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [55]
197 (3aS,4aR,5R,5aS,6aS)-5a-methyl-5-(3-oxobutyl) octahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [55]
198 (3aS,4aR,5R,5aR,6aR)-5a-methyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carbaldehyde C. abrotanoides [55]
199 (3aS,4aR,5R,5aR,6aR)-5a-methyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carboxylic acid C. abrotanoides [55]
200 Ethyl 5a-methyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-carboxylate C. abrotanoides [55]
201 4-(5a-methyl-3-methylene-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-yl) butan-2-yl 2,4-dinitrobenzoate C. abrotanoides [1]
202 4-(3,5a-dimethyl-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-yl) butan-2-yl 2,4-dinitrobenzoate C. abrotanoides [56]
203 (3aR,4aS,5S,5aR,6aR)-3,5a-dimethyl-5-(3-oxobutyl) octahydro-2H-cyclopropa[f]benzofuran-2-one C. abrotanoides [56]
204 Dihydrocarabrone C. abrotanoides [56]
205 Carabrol-4-O-palmitate C. abrotanoides [27]
206 Carabrol-4-O-linoleate C. abrotanoides [27]
207 Carabrol isovalerate C. lipskyi [53]
208 (4S)-acetyloxyl-11(13)-carabren-8β,12-olide C. faberi [52]
209 Carabrone C. faberi [52]
210 Carabrol C. faberi [52]
211 11α,13-Dihydrocarabrol C. divaricatum [29]
212 4R-carabrol C. divaricatum [57]
　 Xanthanolides 　
213 1β,4β-Epoxy-5β-hydroxy-10αH-xantha-11(13)-en-12,8β-olide C. longifolium [58]
214 1β,4β,4α,5β-Diepoxy-10αH,11αH-xantha-12,8β-olide C. longifolium [58]
215 4-Acetoxy-1β,5β-epoxy-10αH-xantha-11(13)-en-12,8β-olide C. longifolium [58]
216 Tomentosin C. macrocephalum [59]
217 4H-tomentosin C. macrocephalum [59]
218 4H-xanthalongia C. cernuum [37]
219 Xanthalongia C. cernuum [37]
220 11α,13-Dihydro-4H-xanthalongin C. divaricatum [29]
221 4-(2-Methybutyryl)-4H-tomentosin C. macrocephalum [33]
　 Eremophilanes 　
222 6β-Hydroxy-8α-ethoxyeremophil-7(11)-en-12,8β-olide C. cernuum [37]
223 Carperemophilanes A C. abrotanoides [60]
224 Carperemophilanes B C. abrotanoides [60]
　 Dimer 　
225 Carpedilactone A C. faberi [61]
226 Carpedilactone B C. faberi [61]
227 Carpedilactone C C. faberi [61]
228 Carpedilactone D C. faberi [61]
229 Guaianodilactone A C. faberi [62]
230 Guaianodilactone C C. faberi [62]
231 Guaianodilactone B C. faberi [62]
232 Guaianodilactone D C. faberi [62]
233 Faberidilactone A C. faberi [63]
234 Faberidilactone B C. faberi [63]
235 Faberidilactone C C. faberi [63]
236 Faberidilactone D C. faberi [63]
237 Faberidilactone E C. faberi [63]
238 Endodischkuhriolin C. faberi [63]
239 Faberidilactone F C. faberi [64]
240 Faberidilactone G C. faberi [64]
241 Faberidilactone H C. faberi [64]
242 Dicarabrol C. abrotanoides [65]
243 Dicarabrones A C. abrotanoides [66]
244 Dicarabrones B C. abrotanoides [66]
245 Dicarabrol A C. abrotanoides [67]
246 Dicarabrone C C. abrotanoides [67]
247 Dipulchellin A C. abrotanoides [67]
248 Carabrodilactones A C. abrotanoides [68]
249 Carabrodilactones B C. abrotanoides [68]
250 Carabrodilactones C C. abrotanoides [68]
251 Carabrodilactones D C. abrotanoides [68]
252 Carabrodilactones E C. abrotanoides [68]
253 Carpedilactone E C. macrocephalum [69]
254 Carpedilactone F C. macrocephalum [69]
255 Carpedilactone G C. macrocephalum [69]
　 Sesquiterpenes without lactonic ring 　
256 1β,6α-Dihydroxy-4(15)-eudesmene C. divaricatum [70]
257 β-Dictyopterol C. divaricatum [70]
258 α-Costic acid C. abrotanoides [33]
259 Grasshopper ketone C. abrotanoides [71]
260 (3S,5R,6S)-3-hydroxy-5,6-epoxy-β-ionone C. abrotanoides [71]
261 4-Hydroxy-4-(3-oxo-1-butenyl)-3,5,5-trimethylcyclohex-2-en-1-one C. abrotanoides [71]
　 Monoterpene 　
262 2,5-Dimethoxythymol C. divaricatum [72]
263 2-Methoxythymol isobutyrate C. divaricatum [72]
264 10-Isobutyloxy-8,9-epoxythymol isobutyrate C. divaricatum [72]
265 10-(2-Methyl-butyloxy)-8,9-epoxythymolisobutyrate C. divaricatum [72]
266 2-(2′-Methoxy-p-tolyl) glyceryl 1,3-diisobutyrate C. lipskyi [73]
267 2-(2′-Methoxy-p-tolyl) glyceryl 1-isobutyrate-3-acetate C. lipskyi [73]
268 3-Methyl-8-acetoxy-9,10-diisobutyryloxy-p-cymene C. cernuum [35]
269 (1R,2S,4S,5R)-2,5-dihydroxy-p-menthane C. minum [74]
270 (1S,2S,4R,5S)-2,5-dihydroxy-p-menthane C. minum [74]
271 (3R,4R,6S)-3,6-dihydroxy-p-l-menthene C. minum [74]
　 Diterpenoids 　
272 12(S)-hydroxygeranylgeraniol C. divaricatum [75]
273 (2E,10E)-1,12-dihydroxy-18-acetoxy-3,7,15-trimethylhexadeca-2,10,14-triene C. divaricatum [75]
274 (2E,6E,11S,12R)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-1,12-diol C. triste [10]
275 (2E,6Z,11S,12R)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-7-[(acetylox)methy]-1,12,19-triol C. triste [10]
276 (2E,6Z,11S,12R)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-7-[(acetylox)methy]-12,19-diol-1-acetate C. triste [10]
277 (2E,6Z)-3,7,11,15-tetramethylhexadeca-2,6,14-trien-7-[(acetyloxy)-methyl]-12-oxo-1,19-diol C. triste [10]
278 (2E,6Z,10E,12R)-7-[(acetyloxy)methyl]-3,11,15-trimethylhexadeca-2,6,10,14-tetraene-1,12-diol C. triste [76]
279 (2E,6Z,10E,12R)-7-[(acetyloxy)methyl]-12-hydroxy-3,11,15-trimethylhexadeca-2,6,10,14-tetraenal C. triste [76]
280 (2E,6Z,12S,13E)-7-[(acetyloxy)methyl]-3,11,15-trimethylhexadeca-2,6,13-triene-1,12,15-triol C. triste [76]
281 (2E,6Z,12R,14S)-7-[(acetyloxy)methyl]-3,11,15-trimethylhexadeca-2,6,15-triene-1,12,14-triol C. triste [76]
282 Rel-(3R,5S)-5-{(1R,5Z,9E)-5-[(acetyloxy)methyl]-11-hydroxy-1,9-dimethylundeca-5,9-dien-1-yl} tetrahydro-2,2-dimethylfuran-3-ol C. triste [76]
283 Trans-phytol C. faberi [52]
284 8α,15-Dihydroxy-13E-labdene C. faberi [52]
285 (6E,10E,14E)-3,7,11,15-teramethylhexadecane-1,6,10,14-teraene-3α,5α,16-triol C. humile [23]
286 α-Tocopherylquinone C. humile [23]
287 Dehydroabietic acid C. humile [23]
288 Atractyligenin C. humile [23]
　 Glycosidic 　
289 Carpeside A C. cernuum [77]
290 Carpeside B C. cernuum [77]
291 Eupatriol 9-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside C. cernuum [77]
292 Kaempferol-3-O-β-d-glucopyranoside C. cernuum [77]
293 Isoquercetin C. cernuum [77]
294 Luteolin-7-O-β-d-glucopyranoside C. cernuum [77]
295 Kaempferol-3-O-rutinoside C. cernuum [77]
296 (−)-Syringaresinol-4,4′-bis-O-β-d-glucopyranoside C. cernuum [77]
297 Citrusin A C. cernuum [77]
298 (+)-Angelicoidenol 2-O-β-d-apiofuranosyl(1 → 6)-β-d-glucopyranoside C. cernuum [77]
299 (3R,9R)-3-hydroxy-7,8-dihydro-β-ionyl 6-O-β-d-apiofuranosyl-β-d-glucopyranoside C. cernuum [77]
300 Eugenyl-O-b-d-apiofuranosyl-(1 → 6)-b-D-glucopyranoside C. cernuum [77]
　 Others 　
301 Carpesiumaleimides A C. abrotanoides [60]
302 Carpesiumaleimides B C. abrotanoides [60]
303 Carpesiumaleimides C C. abrotanoides [60]
304 2-isopropenyl-6-acetyl-8-methoxy-1,3-benzodioxin-4-one C. divaricatum [70]
305 (3E,6E, 10E,14E,18E)-2,6,10,15,19,23-hexamethyl-3,6,10,14,18,22-tetracosahexaen-2-ol C. divaricatum [70]
306 Neophytadiene C. divaricatum [70]
307 β-Daucosterol C. triste [30]
308 β-Sitosterol C. triste [30]
309 Stigmasterol C. triste [30]
310 3,4,5-Trimethylcyclopent-2-en-1-one C. abrotanoides [54]
311 (E)-2-(3,4,5-trimethylcyclopent-2-en-1-ylidene) hydrazine-1-carboxamide C. abrotanoides [54]
312 4-Ethyl-1-methyl-2-pentylbenzene C. abrotanoides [54]
313 5-(5-Ethyl-2-methylphenyl) pentan-2-one C. abrotanoides [45]
314 1-(5-Ethyl-2-methylphenyl) pentan-1-one C. abrotanoides [37]
315 (4Z,7Z,9Z)-5-Ethyl-3,9-dimethyl-6H-cyclopenta [8] annulene C. abrotanoides [44]
316 (+)-(S)-Dehydrovomifoliol C. cernuum [36]

1.2 Sesquiterpenoids

Sesquiterpenoids account for a large proportion relative to the other types of compounds, 316 sesquiterpenes were isolated from Carpesium plants in the past few decades, characterized, and identified. Sesquiterpenoid lactones can be divided into several main classes due to their structural variations, germacranolides, eudesmanolides, guaianolides, pseudoguaianes, carabranolides, xanthanolides, sesquiterpene dimers, eremophilane, and sesquiterpenes without lactone types were found in the Carpesium genus.

1.2.1 Germacranolides

Germacranolides account for the most significant proportion of sesquiterpenes in the genus Carpesium, and its mother nucleus contains a ten-member ring, setting up a complex and diverse structure. So far, 81 germacranolides-type sesquiterpenes, 1–81, have been reported. Since the first germacranolide, 1 named Ivaxillin, was reported from C. abrotanoides by Maruyama, the unique structural patterns of germacranolides have attracted wide attention. At the same time, Maruyama found compounds 2 and 3 are structurally similar to Ivaxillin [1]. In 2002, Lee repeated column chromatography of the MeOH extract of C. abrotanoides, which led to the isolation of Compound 4 [2]. Compound 5 was isolated from the ethanol extract of the aerial parts of C. abrotanoides in 2009 [3]. C. lipskyi yielded four new germacranolides (6–9) in 1998 and 1999 [4,5]. Ten new sesquiterpene lactones, Carlipsines A-J (10–19) were isolated from the whole plant of C. lipskyi through an in-house LC–MS method in 2019. Compounds 10–13 are 2,5-hemiacetal-linked germacranolides. Compounds 14 and 15 possess a 1,2-epoxy moiety. Compounds 16 and 17 represent unusual 1,5-hemiacetal-linked germacranolides. Compounds 18 and 19 contain tetrahydrofuran units with the oxygen atom bridging C-1 and C-8 [6]. Compounds 20–25 are structurally similar, and the differences between the germacranolide structures are primarily found in the carboxylic acid esters formed at the hydroxyl group at C-9. In addition, the diversity among their carboxylate esters may lead to different biological activities [7,8,9]. Several cytotoxic germacranolides 26–34 were separated from the seed of C. triste [10]. Maruyama M and his groups have reported the isolation and structure elucidation of 5 new germacranolides from C. divaricatum (35–37) in 1990 and C. glossophyllum (60,61) in 1995 [11,12]. Seven years later, 4 new sesquiterpenes of the germacranolide type, named Cardivins A (38), B (39), C (40), and D (41), have been isolated from the aerial parts of C. divaricatum in searching for cytotoxic compounds derived from higher plants [13]. In the ongoing search for new/novel and bioactive products from medicinal plants in China, 18 new germacranolides (42–59) were isolated from the whole plant of C. divaricatum [14,15,16,17,18]. Nepalolides A (62), B (63), C (64), and D (65) were isolated from C. nepalense in 1996 [19]. A new highly oxygenated germacranolide was isolated from C. nepalense, which was named Carcerlane A (66) in 2020 [20]. Between 2016 and 2018, 12 new highly oxygenated germacranolides (67–78) were isolated from C. cernuum [21,22]. Notably, Cernuumolide E–G (71–73) are 2,9-hemiacetal-linked germacranolides that possess two possible diastereomers [21]. Carpescernolides A (77) was rare oxygen bridge-containing sesquiterpene lactone from C. cernuum. Absolute configurations were an oxygen bridge unit (C-2–O-C-5) and a 4, 8-ketal system at C-8 [22]. Carpehumine A (79) and B (80) were isolated from the aerial parts of C. humile [23]. As part of the ongoing efforts to discover structurally novel bioactive natural compounds, especially those possessing anti-influenza A (H1N1) virus and cytotoxic activities, Carpabrotalactone A (81) were isolated from the herbs of C. abrotanoides [24].

1.2.2 Eudesmanolides

Forty-two eudesmanolides (82–123) were isolated and identified from the Carpesium plants. Eudesmanolides are tricyclic sesquiterpenoid lactones containing a 5-membered γ-butyrolactone ring. According to the lactone ring annulation, they can be divided into 2 structural classes: 6,12- and 8,12-olides. Granilin (82) and two other eudesmanolides (83, 84) were found in C. abrotanoides by Maruyama M in 1975 [25]. 11(13)-Dihydrotelekin (85) had been isolated from the whole herb of C. abrotanoides in 1988 [26]. Recently, 4 new eudesmanolides (86–89) were reported and determined by spectroscopic analyses [24,27,28]. Several eudesmanolides (90–97) were isolated from C. divaricatum in 2012 [29,30]. Moreover, Eudesmanolides (98–106) were isolated from the aerial parts of C. macrocephalum by Yang. C in 2002 and 2003 [31,32]. Two rare eudesmanolide glycosides (103,104) were isolated from the seeds of C. macrocephalum by a spectral method [31]. 5α-Epoxyalantolactone (107) which showed the inhibitory effect on albicans biofilm formation and dimorphism was isolated and identified in 2015 [33]. Until now, C. cernuum yielded a series of eudesmanolides (108–118) [34,35,36,37,38]. Carpesin (117) and Telekine (118) were found in C. eximium [38]. In this genus, most of the eudesmanolide structures possess an exocyclic double bond or methyl group at the C-11 position. In addition, 3 new eudesmanolides (119–121) from C. triste [39,40,41] were identified. A known eudesmanolide (122) from C. minum and another eudesmanolide (123) from C. fructus were isolated and identified based on spectroscopic data [42,43].

1.2.3 Guaianolides and pseudoguaianes

The guaianolides are regular tricyclic sesquiterpene lactone with prominent structural characteristics. One ring of guaiacane is connected to a five-membered carbocycle at positions C-1 and C-5, and C-7 forms a five-membered γ-lactone carbocycle with C-6 or C-8. Pseudoguaiane lactone has a highly functional structure, which is similar to guaianolides. The difference lies in the methyl connection mode on C-15, the pseudoguaianes are connected to C-5, the guaianolides are connected to C-4. In the 20th century, the guaianolides (124–134) were found primarily in C. abrotanoides [44,45,46,47,48]. Up to now, the guaianolides (135–149) were isolated from the whole plant of C. abrotanoides. Their structures were elucidated based on spectroscopic data and HR-ESI-MS analysis [2,3,49,50]. In the 21st century, the guaianolides (150–169) were found in C. divaricatum, C. triste, C. macrocephalum, C. faberi, and C. rosulatum [7,29,30,37,40,43,51,52,53]. The pseudoguaianes (170–178) were found in C. abrotanoides, C. faberi, C. cernuum, and C. minus [2,3,37,42,50,52].

1.2.4 Carabranolides

Carabranolides are not rich in this genus, which can be biosynthesized from a xanthanolide carbon skeleton by connecting C-5 and C-10, forming a ring. Most of the carbon on the 11 positions have a double annular bond. In 1960s, Minato and his team found 33 Carabranolides (179–200) from C. abrotanoides [54,55]. In the next 20 years, 4 Carabranolides (201–204) were isolated from the same plate [1,56]. Two new Carabranolides (205 and 206) were found in C. abrotanoides by extensive spectroscopic analysis [27]. The Carabranolides (207–212) were isolated and identified from C. lipskyi, C. divaricatum, and C. faberi [29,52,53,57].

1.2.5 Xanthanolides

The xanthanolides are similar to the guaianolides in structure. In Carpesium genus, xanthane-type compounds are relatively rare, and only nine xanthanolides were isolated and characterized. Three xanthanolides (213–215) were isolated from the aerial parts of C. longifolium [58]. Structures of compounds 213 and 214 are more unique. The most notable feature is that the secoregular long-chain is fused to the hydroxyl group at C-1 or C-5, forming an epoxide. Tomentosin (216) and 4H-tomentosin (217) were isolated from C. macrocephalum in 2004 [59]. 4H-Xanthalongia (218) and xanthalongia (219) were isolated from C. cernuum in 2010 [37]. 11α,13-dihydro-4H-xanthalongin (220) were isolated from C. divaricatum in 2012 [29]. A new xanthanolide (221) was found from C. macrocephalum in 2015 [33].

1.2.6 Eremophilanes

The structure of eremophilanes lactone is comparable to that of the eudesmanolides, which is characterized by 2 methyl groups at positions 14 and 15. There are three sesquiterpenes of this type in Carpesium genus. One eremophilane (222) was found from C. cernuum in 2010 [37]. Carperemophilanes A (223) and Carperemophilanes B (224) were isolated from C. abrotanoides in 2019 [60].

1.2.7 Sesquiterpene lactone dimer (SLD)

SLD represents natural products with C30 skeleton synthesized by two homologous or heterologous sesquiterpene monomers. In recent years, 31 sesquiterpene dimers have been found from the Carpesium genus. The biosynthetic pathways of different sesquiterpene dimers are different, which can be divided into the following four types: Diels–Alder reaction, exo–Diels–Alder reaction, cycloaddition, and free radical coupling reaction. Sesquiterpene dimers exhibit more potent biological activity than sesquiterpene monomers through different complex chiral centers. Four new isomeric SLDs, Carpedilactones A–D (225–228), were isolated from the acetonic extract from C. faberi. Among them, 225–227 are the first three 2,4-linked exo-Diels−Alder adducts between a eudesmanolide dienophile and a guaianolide diene [61]. Ten SLDs (229–238) were found from C. faberi in 2015 [62,63]. 229–232 were Diels–Alder adducts between 2 homo guaianolide units. Guaianodilactones A–C (229–231) were exo-1,3-linked, while Guaianodilactones D (232) was the endo-2,4-linked [62]. Faberidilactone A (233) was a stacked arrangement of two sesquiterpene monomers. Faberidilactone A (233) and Faberidilactone B (234) were a pair of 2,4-linked exo/endo diastereoisomeric carabranolide-guaianolide dimers [63]. Faberidilactone C–E (235–237) were exo congeners. Endodischkuhriolin (238) was the endo diastereoisomer of dischkuhriolin [63]. Next year, Faberidilactone F–H (239–241) were isolated from C. faberi [64]. At the same time, 3 new dimeric sesquiterpene, Dicarabrol (242), Dicarabrones A (243) and Dicarabrones B (244), were isolated from the whole plant of C. abrotanoides [65,66]. Dicarabrones A and B have a pair of epimers possessing a new skeleton featuring a cyclopentane ring connecting two sesquiterpene lactone units [66]. Three rare SLDs, Dicarabrol A (245), Dicarabrone C (246), and Dipulchellin A (247), were isolated from whole plants of C. abrotanoides. Their structures were elucidated by comprehensive analyses of NMR and MS spectroscopic data [67]. Five new unusual C17/C15 SLDs, Carabrodilactones A–E (248–252) were isolated from whole plants of C. abrotanoides. The structures of those featured a flexible C-11/C-13′ linked single bond between two sesquiterpene units and tailed acetyl connected to the C-13 position [68]. Three new SLDs, Carpedilactones E–G (253–255), were isolated from the acetonic extract of C. macrocephalum [69].

1.2.8 Sesquiterpenes without lactonic ring

Although sesquiterpenoid lactones compose the majority of sesquiterpenes, six sesquiterpenes without lactonic rings were found. In 2010, Chung et al. isolated two sesquiterpenes (256) and (257) from C. divaricatum [70]. In 2015 and 2019, four sesquiterpenes (258–261) were isolated from C. abrotanoides [33,71].

1.3 Monoterpene

Carpesium plants also contain monoterpenes, and approximately ten of these compounds have been identified and isolated. Four monoterpenes (262–265) were isolated from the aerial parts of C. divaricatum. The structures were elucidated by high-field 1D and 2D NMR techniques [72]. At the same time, two new monoterpene derivatives, 2-(2′-methoxy-p-tolyl) glyceryl 1,3-diisobutyrate (266) and 2-(2′-methoxyp-tolyl) glyceryl 1-isobutyrate-3-acetate (267) were isolated from the whole plants of C. lipskyi [73]. A new monoterpene (268) derivative from C. cernuum was found in 2001 [35]. Gao and Chen used repeated column chromatography with silica gel, Sephadex LH-20, and preparative HPLC to isolate the chemical constituents from the aerial part of C. minum, and the structures (269–271) were elucidated based on spectral data [74].

1.4 Diterpenoids

The genus Carpesium was full of diterpenoids, and most of the isolated examples are acyclic. A new acyclic diterpene (272) and a known acyclic diterpene 12(S)-hydroxygeranylgeraniol (273) were isolated from the aerial parts of C. divaricatum in 1999 [75]. In addition, nine new acyclic diterpenes (274–282) were isolated from the seeds of C. triste in 2007–2008 [10,76]. The structures of the new compounds were elucidated by spectroscopic methods. In 2011, two known diterpenes (283–284) were isolated from the whole plant of C. faberi [52]. From the aerial parts of C. humile, a new phytane diterpene and 3 known diterpenoids (285–288) were found by Xu in 2018 [23].

1.5 Glycosidic

In 2007, Carpesides A (289) and B (290), two new 8-O-4′-neolignan glucosides, and eupatriol 9-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside (291), and one new monoterpenoid diglycoside, were first identified from the genus Carpesium [77]. At the same time, 9 known (292–300) glycosidic compounds, were isolated from the aerial part of C. cernuum. The structures of the new glycosides are elucidated employing chemical methods and spectroscopic studies [77].

1.6 Maleimide-bearing compounds and others

There are 3 maleimide-bearing compounds isolated from C. abrotanoides in 2019, and named as carpesiumaleimides A (301), carpesiumaleimides B (302), carpesiumaleimides C (303) [60]. Chung et al. isolated compounds 304–306 from the whole plants of C. divaricatum in 2010 [70]. Su et al. isolated some steroids (307–309) from C. triste in 2012, and Kariyone et al. isolated 7 other compounds 310–316 from C. abrotanoides and C. cernuum [30,37,45,47,54].

2 Pharmacology

2.1 Cytotoxicity and anti-tumor activity

Through a research design with molecular structure and efficacy, investigations indicate that sesquiterpenen lactones possessing α-methylene-lactone and γ-butyl-lactone exhibit anti-tumor and cytotoxic activities. Anti-tumor activities of Carpesium compounds are reflected in their potent cytotoxicity on many kinds of cancer cells in vitro. Therefore, Sesquiterpene lactone constituents of this genus have caused a great interest.

In a bioassay-guided search for cytotoxic compounds from higher plants of South Korea, compounds 38–41 showed cytotoxicity to human tumor cells (A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15) as determined by the SRB assay. The ED50 values ranged from 1.08 to 8.36 μg/mL and were compared with doxorubicin (ED50 value range: 0.12–2.4 μg/mL) [13]. Two years later, Kim and his groups, continuing investigation on the constituents of C. divaricatum, presentend two compounds 272 and 273, which exhibited cytotoxicity against cultured human tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF498, and HCT15) with ED50 values ranging from 4.38 to 10.2 and 4.17 to 8.33 μg/mL, respectively [75]. Compounds 4, 113, 118, 135, 170, 171, 209, and 210 were tested for their cytotoxic activity against L-1210, A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15 tumor cell lines. Similar to cisplatin, compounds 113, 118, 135, and 170 exhibited potent cytotoxicity against five human tumor cells. Carabrone (209), Carabrol (210), and 11,13-didehydroivaxillin (4) also showed significant cytotoxic activity. Moreover, this study demonstrated the role of the α-methyl-γ-lactone for cytotoxicity of sesquiterpene lactones [2]. Nine compounds were assessed for cytotoxic activity in vitro against SMMC-7721, HL-60, and L02 cells. Compounds 26–30 and 34 exhibited significant cytotoxicity against HL-60 cells, and compound 276 exhibited cytotoxicity against SMMC-7721 cells. In this study, they found that the α,β-unsaturated lactone is the key active center in these sesquiterpenoids, and the number of acetoxy groups may also affect the cytotoxicity [10]. At the same time, 4 other compounds 21–24 from C. triste, showed significant cytotoxicity (ED50 value: 4.3–16.8 μM) against 5 human tumor cell lines (A549, SK- OV-3, SK-MEL-2, XF498, and HCT15). Four acyclic 12-hydroxygeranylgeraniol-derived diterpenoids were assayed for their in vitro cytotoxic activities toward SMMC-7721, HL-60, and L02 cells according to SRB. All compounds were inactive toward SMMC-7721 and L02 cells (IC50 >100 μg/mL), But compounds 278 and 280 exhibited weak cytotoxicity against HL-60 cells (IC50 40.7 ± 6.9 and 65.6 ± 8.1 μg/mL) [76]. The cytotoxic activity of nine compounds from C. divaricatum against KB, MCF-7 and HepG-2 cells was evaluated by MTT assay. Ivalin (113), telekin (118), and 1-oxoeudesm-11(13)-eno-12,8α-lactone (93) exhibited strong cytotoxicity against tumor cells. But other compounds did not show potential cytotoxicity. The study sheds some light on the factors that are associated with the anti-tumor activity of sesquiterpene lactones. The alkylating center reactivity, lipophilicity, molecular geometry, and electronic features can affect its activity levels [29]. In the past 2 years, important progress was made in the anti-proliferation mechanisms of Telekin (118) in human hepatocellular carcinoma. Studies found that Telekin can activate the mitochondria-mediated apoptotic pathway in hepatocellular carcinoma cells [78]. Moreover, Telekin (118) can suppress hepatocellular carcinoma cells in vitro by inducing G2/M phase arrest via activating the p38 MAPK pathway [79]. Between 2014 and 2017, 26 sesquiterpene dimers were isolated and evaluated for cytotoxicity against human cancer cell lines. Compounds 225–232 exhibited potent inhibition against human leukemia (CCRF–CEM) cell lines with IC50 values of 0.14, 0.32, 0.35, 0.16, 9.13, 2.03, 4.74, and 13.72 μM [61,62]. Faberidilactones A–C (233–235), Faberidilactones E (237), and endodischkuhriolin (238) showed potent cytotoxicity with IC50 value in the range of 1.11–8.50 μM against the four human tumor cell lines (CCRF–CEM, K562, HL-60, and HCT116 cells). But Faberidilactones D (236), a dimer without α-methylene-γ-lactone, was less than the other 4 compounds. Furthermore, Young studies showed that 3 exo-2,4-linked eudesmanolide-guaianolide SLDs (233, 235, 237) dose-dependently suppressed NF-ĸB activation [63]. Faberidilactones F (239) was the endo diastereodimer of Carpedilactone A (225). Faberidilactones G (240) was 1 oxygen atom less than Faberidilactones F (239). Both were evaluated for cytotoxicity against human leukemia (CCRF–CEM) cell lines by MTT assay with doxorubicin as the positive control. The value of IC50 were 5.62 ± 0.34 and 3.74 ± 0.22 μM, respectively, which was lower than that of DOX (IC50 0.03 μM) [64]. Dicarabrones A (243) and B (244), a pair of epimers possessing a new skeleton featuring a cyclopentane ring connecting two sesquiterpene lactone units, showed moderate effects on HL-60 cells with IC50 values of 9.1 and 8.2 μM, respectively [66]. Dicarabrol (242) revealed a high degree of similarity with Dicarabrones A (243) and B (244), and had significant in vitro cytotoxicity against the K562, MCF-7, Hela, DU145, U937, H1975, SGC-7901, A549, MOLT-4, and HL60 cell lines with IC50 values ranging from 0.1 to 3.3 μM [65]. Dicarabrol A (245), dicarabrone C (246), and dipulchellin A (247), 3 unique SLDs from Carpesium abrotanoides, exhibited moderate cytotoxicity against HL-60 cells with IC50 values of 8.7 ± 0.3, 8.2 ± 0.3, and 8.9 ± 0.4 μM, respectively [67]. Compared with DOX as the positive control, the SLDs (253–255) were evaluated for cytotoxicity against 4 human cancer cell lines (A549, BEL 7404, HCT116, and MDA-MB-231) by MTT assay. Carpedilactones E (253) showed potent cytotoxicity against the four cell lines with IC50 values of 2.04 ± 0.12, 2.27 ± 0.25, 5.17 ± 0.45, and 3.77 ± 0.40 μM, respectively. Interestingly, Carpedilactones F (254) only exhibited potent cytotoxicity against HCT116 cells with IC50 values of 3.30 ± 0.18 μM [69]. Incaspitolide A (30), divarolide A (42), divarolide C (44), incaspitolide B1(46), incaspitolide B2 (47), and compound 48 were obtained in sufficient amounts to be evaluated for their cytotoxic activity against human cancer cell lines (HeLa, HepG2, MGC-803, and A549). All evaluated compounds exhibited strong cytotoxicity, but only compounds 42, 44, 46, and 48 had the IC50 values of 0.83, 1.18, 0.57, and 1.70 μM, respectively, against HeLa cell lines, superior to that of the positive control doxorubicin (IC50 value 2.21 μM). Besides, new compound 42 also displayed strong cytotoxicity against A549 with IC50 value of 8.93 μM (doxorubicin showed IC50 value of 4.18 μM) [14]. Twelve highly oxygenated germacranolides (67–78), isolated from C. cernuum, were evaluated for their cytotoxicity against human cancer cell lines in vitro. Among the tested compounds, cernuumolide H (74) exhibited moderate cytotoxicity against the HCT116, MDA-MB-231, and BEL7404 cells with IC50 values of 0.87, 2.02, and 1.80 μM, respectively [21]. Carpescernolides A (77) exhibited cytotoxicity against SMMC-7721 cells with IC50 value of 38.86 ± 2.35 μM. Carpescernolides A showed dose-dependent inhibitory effects on cancer cell proliferation and migration ability. It can inhibit cancer cell colony formation ability and cancer cell migration [22]. The cytotoxicity of compounds 8, 36, 79, 80, 285–288 were evaluated against a panel of 6 human cancer (HepG2, HeLa, HL60, SGC7901, Lewis, and MDA231) cell lines in vitro by MTT assay. Four germacrane sesquiterpene lactones (8, 36, 79–80) showed potent cytotoxic activities, with IC50 values from 3.09 to 7.71 μg/mL. The phytane diterpenes (285–286) displayed good cytotoxic activity against HepG2 and SGC7901 cells, with IC50 values from 5.46 to 8.67 μg/mL, respectively, and moderate inhibition of HeLa, HL60, and Lewis cells. Dehydroabietic acid (287), an abietane-type diterpenoid, showed a modest inhibitory effect against HepG2, HeLa, SGC7901, and Lewis cells, with IC50 values from 14.03 to 21.7 μg/mL. Atractyligenin (288), a kaurane-type diterpenoid, exhibited good cytotoxic activity against HepG2, HL60, SGC7901, and Lewis cells, with IC50 values of 7.12, 6.67, 7.51, and 8.08 μg/mL, respectively [23]. Divarolide E (51) and compound 26 exhibited potent cytotoxicity against hepatocellular cancer (Hep G2) and human cervical cancer (HeLa) cells, superior to those of the positive control cisplatin [17]. Compounds 24 and 34 showed significant cytotoxicity against 3 human tumor cell lines (HeLa, LoVo, and BGC-823) with IC50 values in the range of 4.72–13.68 μM as opposed to the control cisplatin (7.90–15.34 μM) [16]. Two new guaiane-type sesquiterpene lactones, caroguaianolide B and C (140 and 141), along with 2 known sesquiterpene lactones (144 and 147) were isolated from the whole plant of C. abrotanoides, and their cytotoxic activities against the MDA-MB-231 and HGC-27 cancer cell lines in vitro were determined. The result showed that those compounds had strong cytotoxic activities against the MDA-MB-231 cancer cell lines, better than those of the positive control mitomycin C (IC50 4.56 ± 0.67 μM). The values of IC50 were 4.25 ± 1.16, 2.67 ± 0.48, 4.83 ± 0.56, and 4.07 ± 0.96 μM. Moreover, Caroguaianolide B and Caroguaianolide C showed strong cytotoxicity against HGC-27 cancer cell lines with IC50 values of 6.47 ± 0.76 and 4.83 ± 0.55 μM, respectively [50]. Twenty-two germacranolides, including 10 new and 12 known analogues isolated from C. lipskyi, were evaluated for cytotoxicity against HL-60 and A-549 cell lines. Among them, compounds 15–17, 34, 75, and 76 exhibited moderate cytotoxicity against A549 and HL-60 cells with IC50 values ranging from 2.82 to 10.3 μM [18]. In 2019, 2 new eremophilane-type sesquiterpenes, carperemophilanes A and B (223 and 224) were evaluated in vitro for cytotoxicity against 2 human cancer cell lines (MDA-MB-231 and HGC-27) using the MTT method. The values of IC50 were ranging from 22.67 to 37.35 μM [60]. To investigate the cytotoxicity of 4-epi-isoinuviscolide (136), the cytotoxicity of 4-epi-isoinuviscolide was evaluated using the MTT assay. The result found that 4-epi-isoinuviscolide induced pro-death autophagy and apoptosis in MDA-MB-231 cells by upregulating the protein expressions of LC3-II, p-ULK1, Bax, and Bad and downregulating p-PI3K, p-Akt, p-mTOR, p62, Bcl-2, and Bcl-xl [80]. In 2020, 7 compounds, 2, 3, 88, 81, 89, 99, and 156, isolated from the herbs of Carpesium abrotanoides, were tested for cytotoxicity against the ISK, Hela, A549, Sw620, RBE, and Caco-2 cell lines. Among those, compounds 2, 81, 99, and 156 showed cytotoxic activity against the ISK cell line with IC50 values from 13.7 to 30.3 μM. Compounds 81, 99, and 156 showed cytotoxic activity against the Hela cell line with IC50 values from 8.5–10.7 μM. Compound 3 showed cytotoxic activity against the SW620 and RBE cell lines with IC50 values of 12.1–7.8 μM. Compounds 2, 3, 81, and 156 showed cytotoxic activity against the Caco-2 cell line with IC50 values from 13.5 to 21.5 μM [24]. Carpabrotalactone C (87) exhibited potent cytotoxicity against the A549, SMMC-7721, MCF-7, and SW480 cell lines, with IC50 values from 11.46 to 23.68 μM [28]. Five new unusual C17/C15 SLDs, Carabrodilactones A–E (248–252), were evaluated in vitro for cytotoxicity against the 4 cell lines (A549, HCT116, MDA-MB, and BEL7404 cells). Only Carabrodilactones A exhibited significant cytotoxicity against the 4 cell lines with IC50 value in the range of 3.08–8.05 μM [68].

2.2 Anti-inflammatory activity

In recent years, five species including C. divaricatum, C. abrotanoides, C. macrocephalum, C. triste, and C. cernuum were assessed for their anti-inflammatory effects and aid in developing a potential novel therapeutic approach for the treatment of acute and chronic inflammation. Nitric oxide (NO) and prostaglandin E2 (PGE2) are representative pro-inflammatory mediators. Cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) are known inflammatory enzymes that are involved in the production of prostaglandins (PGs) and NO, respectively. Expression of iNOS and COX-2 produce excess NO and PGE2 leading to inflammation. Eun et al. that found compound 25 decreased NO production in LPS/IFN-g-stimulated RAW 264.7 cells in a concentration-dependent manner, with an IC50 of approximately 2.16 μM. However, it had no direct effect on the iNOS activity of RAW 264.7, and the results strongly suggest that the inhibitory effects of this compound are mediated via a reduction in iNOS mRNA expression. It is inferred that the mechanism is to inhibit the activation of NF-κB. Thereby, inhibiting the expression of the iNOS gene and producing an anti-inflammatory effect. C. macrocephalum has been used as traditional medicine for treating inflammatory diseases [81]. In 2010, Lee et al. investigated the inhibitory effects of Carabrol (210), one of the main constituents of C. macrocephalum, on NO production in LPS-activated macrophage cells. In this study, the effects of Carabrol during the inflammatory cascades were evaluated. The result showed that Carabrol inhibited the expression of iNOS and COX-2 through down-regulation of p38 and JNK signal pathways, and suppression of NF-κB activation in LPS-activated macrophages [82]. Furthermore, methanol extract of C. macrocephalum was evaluated the intrinsic mechanisms involved in both in vitro and in vivo experimental models. In in vitro model, the extract inhibited the production of NO in LPS-stimulated RAW 264.7 cells by blocking iNOS expression. It significantly inhibited the release of proinflammatory mediators such as NO, TNF-α, PGE2, and IL-6 in RAW 264.7 macrophages in a concentration-dependent fashion. In in vivo model, the extract concentration-dependently suppressed the acetic acid-induced vascular permeability in mice [83]. Compound 24 from C. triste was recognized as an inhibitor of NO production in LPS-activated macrophage cells. It inhibited the expression of iNOS via downregulation of the ERK1/2 and p38 signal pathways and suppression of NF-κB activation in LPS-activated macrophages [84]. In 2015, the effect of 4,5-epoxy-10,14-dihydro-inuviscolide (135), a novel immunosuppressant isolated from C. abrotanoides, was investigated in an inflammation-induced mouse model and immune cells model. Treatment with the compound 135 inhibited IL-6, IL-4, IL-13, IFN-γ, and IL-10 expression in mRNA and protein levels. Moreover, the results showed that compound 135 effectively hampered the secretion of IFN-γ and IL-10 cytokines in PMA-stimulated NK-YS cells to inhibit NF-κB transcriptional activity and IL-10 promoter activity [85]. The aim is to clarify the mechanism of the anti-inflammatory effects of C. abrotanoides. Experts discussed the potential role of C. abrotanoides-extract (chloroform, ethyl acetate, and ethanol fractions) on the suppression of NO and PGE2, and the production of pro-inflammatory cytokines from LPS-induced macrophage cells. Lee et al. found that the chloroform and ethyl acetate fractions of C. abrotanoides have suppressed NO and PGE2 production via the suppression of iNOS and COX-2 mRNA transcription, and IL-1β biosynthesis from LPS-stimulated macrophage cells [86]. Do-Won Jeong and Eun-Kyeong Lee found that the ethanol fraction of C. abrotanoides suppressed COX-2 and iNOS expression induced by lipopolysaccharide (TLR4 agonist), polyriboinosinic polyribocytidylic acid (TLR3 agonist), and macrophage-activating lipopeptide 2-kDa (TLR2 and TLR6 agonist) [87,88]. In 2020, a study was designed to investigate the effects of methanolic extract of C. cernuum (CLME) on LPS-induced RAW 264.7 mouse macrophages and a sepsis mouse model, by observing the expression of NF-κB, Nrf2/Kelch-like ECH-associated protein 1 (Keap1), and extracellular signal-regulated kinase (ERK) in RAW 264.7 macrophages. The study found that the CLME effectively increased the nuclear accumulation of Nrf2 and concurrently downregulated the nuclear expression of NF-κB in LPS-stimulated RAW 264.7 cells. Furthermore, they found CLEM enhanced the survival rate in sepsis mice but not in a significant level [89].

2.3 Antibacterial activity

As early as 1975, Granilin (82) was obtained from C. abrotanoides, which showed in vitro activity against Cochliobolus miyabeanus and Xanthomonas oryzae [25]. In 2002, an antimicrobial susceptibility study of compounds 103, 113, 118, 209, and 210 were performed by cup plate method. It was found that Ivalin (113), Carabrone (209), and Carabrol (210) exhibited moderate activity against Bacillus subtilise. Compound 103 not only showed strong inhibitory activity against Escherichia coli, but also showed a strong inhibitory effect on Staphylococcus aureus with Telekin (118) [31]. In 2010 and 2012, Feng et al. designed nine derivatives of Carabrone (209) and 38 new ester derivatives of Carabrol (210). They were synthesized and tested in vitro against Colletotrichum lagenarium using the spore germination method. Among all of the derivatives, many compounds show potent antifungal activity than Carabrone (209) and Carabrol (210). It was found that the substituent group on the C-4 position had a significant effect on the movement of Carabrol and its derivatives [90,91]. In 2014, The antimicrobial activity of Carabrone (209) against 11 plant pathogens was evaluated by methods of hypha growth rate, spore germination in vitro, pot culture experiment, and tissue selection method. Han et al. found that Carabrone exhibited suitable fungicidal activities against pathogens with the best inhibitory effect against Gaeumannomyces graminis var. tritici [92]. Sesquiterpenes from C. macrocephalum were evaluated for their antifungal activities against the growth, biofilm formation, and yeast-hyphal transition in Candida albicans. The anti-virulence assay indicated that compounds 135, 118, and 113 inhibited strongly biofilm formation with IC50 values ranging from 15.4 to 38.0 μg/mL, while compounds 221, 135, 107, and 209 inhibited the yeast-to-hyphae morphogenetic transition through microscopic observation [33]. A new dimeric sesquiterpene, dicarabrol (242), together with two known sesquiterpenes, 11(13)-dehydroivaxillin (2), and 2-desoxy-4-epi-pulchellin (173), displayed significant antimycobacterial activity (IC50 3.7, 6.0, and 7.6 μM, respectively) [65]. In 2020, in order to clarify the antimicrobial mechanisms of Carabrone (209), especially for Gaeumannomyces graminis (Get), Wang et al. used Carabrone to induce oxidative stress and apoptosis in Get. The result indicated Carabrone inhibits antioxidant enzymes and promotes ROS overproduction, which causes membrane hyperpermeability, the release of apoptotic factors, activation of the mitochondria-mediated apoptosis pathway, and fungal cell apoptosis [93].

2.4 Antiplasmodial activity

In one bioactivity-guided isolation of the chloroform fractions of the whole plants of C. rosulatum, Moon. were the first to report the isolation of ineupatorolides A (60), displaying high antiplasmodial activity of P. falciparum(D10) strain (IC50 = 0.007 μg/mL) [93]. 11(13)-Dehydroivaxillin (2) was a germacranolide sesquiterpene from C. cernuum. Kim et al. demonstrated that 11(13)-Dehydroivaxillin (2) shows antimalarial activity on Plas. berghei in mice. The LD50 of the compound was considered 51.2 mg/kg. 11(13)-dehydroivaxillin (2) exerted a potent inhibition of repository activity at 10 mg/kg/day. In parasitemia, the survival effect of mice treated with 10 mg/kg/day was similar to that of the standard drug chloroquine (5 mg/kg/day) [94]. Using the PLDH assay, testing of compounds 1–3 and 171 for in vitro antiplasmodial activity against the Plasmodium falciparum D10 strains. In view of the result, the germacranolides 1, 2, and 3 were significantly more active than the pseudoguaianolide (171). The IC50 value of ivaxillin (1) of Plasmodium falciparum D10 strain is 4.54 μg/mL. And the excellent activity may be due to the flexible configuration of ten-membered ring [95]. The activity of five compounds 256, 257, 304–306 against P. falciparum strain D10 in vivo was assessed using the parasite lactate dehydrogenase assay method. The main antiplasmodial principle, 2-isopropenyl-6-acetyl-8-methoxy-1,3-benzodioxin-4-one (304), has been isolated from C. divaricatum. It exhibited an antiplasmodial activity with IC50 values of 2.3 ± 0.3 μM. This is the first report on the antiplasmodial activity of the compounds from C. divaricatum [70].

2.5 Insecticidal activity

The immunotoxicity effects of the chloroform extract of the whole parts of C. rosulatum were studied by Moon et al. in 2011. The chloroform extract had a significant toxic impact against early fourth-stage larvae of Aedes aegypti (L.) with an LC50 value of 13.11 ppm and an LC90 value of 20.33 ppm [7]. Aid to the discovery of new insecticide agents from the fruit of C. abrotanoides, Wu et al. selected two insect pest species of agricultural importance in order to characterize 7 compounds’ insecticide activity. Compound 137 displays dose- dependent insecticide activity toward 3rd instar larvae of P. xylostella (ED50 = 19.84 μg/mL) and 4th instar larvae of B. odoriphaga (LD50 = 18.71 μg/mL). Furthermore, compound 137 showed 95% mortality after 48 h at 100 mg/L doses against larvae of B. odoriphaga [49].

3 Conclusion

The genus Carpesium includes 24 species, and some of them have been used as traditional herbal medicines. The chemical investigation of Carpesium species has revealed that some components exhibit significant bioactivity. From our review, it can be seen that there are still many Carpesium species that have received no or only a little attention, and much more phytochemical and biological studies should be carried out on these plants in order to disclose their active principles. The components isolated from the genus Carpesium are mainly terpenes, especially sesquiterpenes. Further studies to exploit other kinds of constituents and new biological activities of the plants of this genus are necessary to obtain more potentially bioactive components.

# These authors contributed equally to this work.

tel: +86-31186265634

Acknowledgments

We are grateful for financial support from the Scientific Research Project of Hebei Administration of Traditional Chinese medicine (No. 2017066), and the Natural Science Foundation of Hebei Province (H2020205699).

  1. Funding information: This study was supported by the Scientific Research Project of Hebei Administration of Traditional Chinese medicine (No. 2017066).

  2. Conflict of interest: Authors state no conflict of interest.

  3. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Received: 2022-03-11
Revised: 2022-05-05
Accepted: 2022-05-19
Published Online: 2022-07-21

© 2022 Ning-Ning Shi et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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