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. 2023 Apr 20;14:1169629. doi: 10.3389/fphar.2023.1169629

TABLE 3.

Chemical compounds detected in the species of the genus Tanacetum.

Compound Parts used Solvent Species Analytic method Country References
Hydroxycinnamic acid derivatives
Chlorogenic acid 1 L, WP MeOH T. vulgare HPLC-UV Poland Türkiye Bączek et al. (2017)
T. macrophyllum
T. corymbosum
T. balsamita
T. cilicicum
Caffeic acid 2 WP, Fl EtOH/W (40:60 v/v)70% EtOH MeOH T. vulgare HPLC, HPLC–MS Poland Türkiye, Romania Bączek et al. (2017)
T. balsamita
T. parthenium
3,5-O-Dicaffeoylquinic acid 3 L EtOH/W (40:60 v/v) T. balsamita HPLC-DAD Pukalskas et al. (2010)
Rosmarinic acid 4 WP EtOH/W (40:60 v/v) T. vulgare HPLC Poland, Türkiye Bączek et al. (2017)
T. balsamita
Chicoric acid 5 WP EtOH/W (40:60 v/v) T. vulgare HPLC Poland, Türkiye Bączek et al. (2017)
T. balsamita
p-Coumaric acid 6 AP 70% EtOH T. balsamita HPLC-MS Iran Benedec et al. (2016)
T. parthenium
Ferulic acid 7 AP 70% EtOH MeOH T. balsamita HPLC-MS Iran Benedec et al. (2016), Rezaei et al. (2017)
T. parthenium
Cinnamic acid 8 AP EtOH T. balsamita HPLC Türkiye Savci et al. (2020)
T. chiliophyllum
T. zahlbruckneri
T. parthenifolium
Sinapic acid 9 AP MeOH T. parthenium HPLC Iran Rezaei et al. (2017)
Neochlorogenic acid 10 Fl, R, L MeOH T. vulgare LC-DAD/ESI-TOF-MS Serbia Devrnja et al. (2017)
Cryptochlorogenic acid 11
1-Caffeoylquinic acid 12
3,4-O-Dicaffeoylquinic acid 13
3,5-O-Dicaffeoylquinic acid 14
4,5-O-dicaffeoylquinic acid 15
3,5-Dichlorogenic acid 16 Fl 70% EtOH T. vulgare HPLC Ukraine Yu et al. (2017)
4,5-Dichlorogenic acid 17
2-O-Caffeoylglucaric acid 18 AP H2O EtOH/H2O T. vulgare UHPLC-HRMS Türkiye Ak et al. (2021)
3-O-Feruloylquinic acid 19
1-Caffeoyl-3-hydroxy-dihydrocaffeoylquinic acid 20
Caffeic acid-O-hexoside 21
4,5-Dicaffeoylquinic acid 22
Hydroxybenzoic acid derivatives
Gentisic acid 23 AP, Fl 70% EtOH T. balsamita α , T. vulgare β HPLC-MS α , UHPLC-HRMS β Romania α , Türkiye β Benedec et al. (2016); Ak et al. (2021)
Salicylic acid 24 AP EtOH T. balsamita HPLC Savci et al. (2020)
4-Hydroxybenzoic acid 25 AP EtOH T. balsamita HPLC Türkiye, Iran Rezaei et al. (2017); Savci et al. (2020)
T. parthenifolium
T. zahlbruckneri
T. chiliophyllum
T. parthenium, T. vulgare
Gallic acid 26 AP MeOH T. cilicicum HPLC-UV Türkiye, Iran Gecibesler et al. (2016), Rezaei et al. (2017)
T. parthenium
Syringic acid 27 AP MeOH T. cilicicum HPLC-UV Turkey, Iran Gecibesler et al. (2016), Rezaei et al. (2017)
T. parthenium
Vanillic acid 28 AP MeOH T. parthenium HPLC Iran Rezaei et al. (2017)
Cyclitols
Shikimic acid 29 AP H2O, EtOH/H2O T. vulgare UHPLC-HRMS Türkiye Ak et al. (2021)
Quinic acid 30
Flavonols
Quercetin 31 AP 70% EtOH α , MeOH β T. balsamita α , T. vulgare β HPLC-MS Romania Benedec et al. (2016), Ivănescu et al. (2021)
Quercitrin 32
Isoquercitrin 33
Rutin 34 AP α , WP β 70% EtOH α , Isopropanol/hexane (2:3 v/v) β T. balsamita α , T. densum β HPLC-MS Romania α , Türkiye β Benedec et al. (2016), Emre (2021)
Kaempferol 35
5,7,3',4'-Tetrahydroxy-3,8-dimethoxyflavonol 36 AP MeOH/W/HOAc (79:20:1) T. balsamita HPLC-DPPH Lithuania Pukalskas et al. (2010)
Catechin 37 WP α,γ , AP β Isopropanol/hexane (2:3 v/v) α ,MeOH β,γ T. densum α HPLC–UV Türkiye α,β , Italy γ Gecibesler et al. (2016), Emre (2021), Recinella et al. (2021)
T. cilicicum β
T. parthenium γ
Galangin 38 AP MeOH T. cilicicum HPLC–UV Türkiye Gecibesler et al. (2016)
6-Hydroxykaempferol 39 L 80% MeOH T. vulgare, T. parthenium HPLC, NMR Germany Williams et al. (1999)
6-Hydroxykaempferol 3,5,7-trimethyl ether 40
Myricetin 41 WP 80%MeOH α , EtOH β T. densum α HPLC-DAD Türkiye Emre (2021)
T. balsamita β
Jaceidin 42 AP H2Cl2/MeOH (1:1) T. sinaicum TLC, MS NMR Egypt Marzouk et al. (2016)
Chrysosplenetin 43
Vitexicarpin 44
Casticin 45
Centaureidin 46 AP EtOAc T. parthenium HPLC, NMR France Long et al. (2003)
Flavones
Chrysin 47 AP MeOH T. parthenium HPLC–UV Türkiye Gecibesler et al. (2016)
Apigenin 48 AP α , L γ MeOH α , 80% MeOH γ , H2Cl2/MeOH (1:1) β T. macrophyllum α HPLC,TLC, MS,NMR Romania α , Egypt α,β , Germany γ Williams et al. (1999); Marzouk et al. (2016), Ivănescu et al. (2021)
T. vulgare α
T. corymbosum α
T. parthenium γ
T. sinaicum α,β
Acacetin 49 AP α , L β H2Cl2/MeOH (1:1) α , MeOH β T. sinaicum α LC-MS, TLC, MS, NMR Egypt α , Japan β Uehara et al. (2015), Marzouk et al. (2016)
T. vulgare β
Luteolin 50 AP H2Cl2/MeOH (1:1) α , MeOH β , 80% EtOH γ T. sinaicum α TLC, MS, NMR Egypt α , United kingdom β , United States γ Juan-Badaturuge et al. (2009), Marzouk et al. (2016)
T. vulgare β
T. parthenium γ
Cirsilineol 51 AP α , WP β H2Cl2/MeOH (1:1) α , MeOH β T. sinaicum α TLC, MS, NMR Egypt α , Türkiye β Polatoğlu et al. (2013), Marzouk et al. (2016)
T. chiliophyllum β
Santin 52 AP EtOAc T. parthenium HPLC, NMR France Long et al. (2003)
Apigenin 7-O-β-glucopyranoside 53 AP α , L β H2Cl2/MeOH (1:1) α , MeOH β T. sinaicum α , T. vulgare β TLC, LC-MS, MS, NMR Egypt α , Finland β , Sweden β Uehara et al. (2015), Marzouk et al. (2016)
Apigenin 7-O-β-glucuronide 54
Luteolin 7-O-β-glucopyranoside 55
luteolin 7-O-β-glucuronide 56
Chrysoeriol 7-O-glucuronide 57 L MeOH T. vulgare LC-MS, UV, HPLC Japan Uehara et al. (2015)
Hispidulin 58
Nepetin 59
Eupatilin 60
Jaceosidin 61
Pectolinarigenin 62
5,7,4'-trihydroxy-3,6-dimethoxyflavone 63 AP EtOH T. oshanahanii 1H NMR, IR, 13C NMR Spain Triana et al. (2013)
5-hydroxy-3,6,7,8,3’,4’-hexamethoxyflavone 64 WP MeOH T. artemisioides 2D-NMR, IR, COSY, HMQC Pakistan Hussain et al. (2010)
5-Demethylnobiletin 65
Coumarins
Isofraxidin 66 R n-Hexane T. parthenium HPLC, NMR Poland Kisiel and Stojakowska (1997)
9-Epipectachol B 67
Scopoletin 68 AP α,β , Sd γ , Pe δ EtOAc α , EtOH β ,CH2Cl2 γ , EO δ T. cadmeum α 1H NMR, IR, UV, MS, GC-MS Türkiye α , Spain β , United Kingdom γ , Iran δ Gonzalez et al. (1990), Susurluk et al. (2007)
T. ferulaceum β
T. parthenium γ
T. balsamita δ
Scoparone 69 AP EtOH T. ferulaceum 1H NMR, IR, 13C NMR Spain Gonzalez et al. (1990), Triana et al. (2013)
T. ptarmiciflorum
T. oshanahanii
7-Hydroxycoumarin (Umbelliferone) 70 AP MeOH T. cadmeum X-ray, 1H NMR, IR, TLC Türkiye Çalişkan et al. (2004), Servi̇ and Gören (2019)
T. mucroniferum
Dimethylfraxetin (6,7,8-Trimethoxycoumarin) 71 AP EtOH T. ferulaceum 1H NMR, MS Spain Gonzalez et al. (1990)
Ceramides
Tanacetamide A 72 WP MeOH T. artemisioides 2D-NMR, IR, COSY, HMQC Pakistan Ahmad et al. (2004)
Tanacetamide B 73
Tanacetamide C 74 WP MeOH T. artemisioides 2D-NMR, IR, COSY, HMQC Pakistan Hussain et al. (2005)
Tanacetamide D 75 WP MeOH T. artemisioides 2D-NMR, IR, COSY, HMQC Pakistan Hussain et al. (2010)
Fatty acids
Capric acid 76 AP α , St β Fl β , WP γ EO α n-Hexane β Isopropanol/Hexane (2:3 v/v) γ T. parthenium α , T. zahlbruckneri β , T. densum γ GC-MS α,B HPLC γ Iran, Türkiye Caglar et al. (2017), Rezaei et al. (2017); Emre (2021)
Myristic acid 77
Palmitic acid 78
Palmitoleic acid 79
Stearic acid 80
Oleic acid 81
Linoleic acid 82
Arachidic acid 83
Erucic acid 84 AP EO T. parthenium GC-MS Iran Rezaei et al. (2017)
Lignoceric acid 85
Lauric acid 86
Margaric acid 87 R, Fl n-Hexane T. zahlbruckneri* GC-MS Iran Caglar et al. (2017)
cis-Vaccenic acid 88
Behenic acid 89
Alkanes
Octadecane 90 Inf EO T. vulgare GC-MS Finland Korpinen et al. (2021)
Eicosane 91
Docosane 92
n-Tricosane 93
Pentacosane 94
Heptacosane 95
n-Nonacosane 96
Hentriacontane 97
Fat-soluble vitamins
Vitamin K1 98 WP i-PrOH/Hexane (2:3 v/v) T. densum HPLC Türkiye Emre (2021)
Vitamin K2 99
Vitamin D2 100
Vitamin D3 101
α-Tocopherol 102
β-Tocopherol 103
Retinol 104
Retinol acetate 105
Carbohydrates
Glucose 106 R, Fl 0.75% AmOx T. vulgare GC-MS, NMR Russia Polle et al. (2001)
Xylose 107
Mannose 108
Galactose 109
Arabinose 110
Apiose 111
2-O-methylxylose 112
Pyrethrins
Pyrethrin I 113 Fl n-Hexane, Ace, PEE, i-PrOH, SFE T. cinerariifolium HPLC–UV, SFC-FID, RP-HPLC– DAD Kenya, Croatia, India, Italy Kasaj et al. (1999), Jeran et al. (2021)
Pyrethrin II 114
Cinerin I 115
Cinerin II 116
Jasmolin I 117
Jasmolin II 118
Sesquiterpene lactones
Parthenolide 119 AP EtOH-H2O (90:10) T. parthenium LC-MS,13C NMR, 1H NMR Brazil Tiuman et al. (2005)
Costunolide 120 AP EtOH T. ferulaceum 1H NMR, MS Spain Gonzalez et al. (1990)
Tatridin A 121
11,13-Dihydrotatridin A 122
Tatridin B 123
Spiciformin 124
lα,10β-Epoxydeacetyllaurenobiolide 125
Deacetyl-beta-cyclopyrethrosin 126
6α-Hydroxy-5,7αH,8βH-eudesm-4 (15)-en-8,12-olide 127
4β,6α-Dihydroxy-5,7αH,8βH-eudesman-8,12-olide 128
Douglanin 129 Fl PEE T. vulgare 13C-NMR, 1H-NMR Italy Rosselli et al. (2012)
Ludovicin A 130
Ludovicin B 131
1α-Hydroxy-1-deoxoarglanine 132
11,13-Dehydrosantonin 133
A, β-Cyclopyrethrosin 134 Fl EtOH T. cinerariifolium CC, NMR Canada Doskotch et al. (1971)
Chrysanin 135
Pyrethrosin 136
Dehydro-β-cyclopyrethrosin 137
Chrysanolide 138
B, (11R)-11,13-Dehydro-tatridin-A 139
Monoterpene hydrocarbons
α-Pinene 140 WP α,β , L γ , AP δ,ζ , F ε EO T. balsamita α , T. vulgare β , T. parthenium γ , T. sinaicum δ , T. cilicicum ε , T. chiliophyllum ζ , T. densum ε GC-FID, GC–MS Italy α,β , Iran γ , Egypt δ , Türkiye ε, ζ Polatoğlu et al. (2009), Bączek et al. (2017); Farzadfar et al. (2017); Elshamy et al. (2021)
β-Pinene 141 WP α,β , L γ , AP δ, ζ EO T. balsamita α , T. vulgare β , T. parthenium γ , T. sinaicum δ , T. chiliophyllum ε , T. chiliophyllum ζ GC-FID, GC–MS Italy α,β , Iran γ , Egypt δ , Türkiye ε, ζ Salamci et al. (2007), Bączek et al. (2017), Farzadfar et al. (2017); Elshamy et al. (2021)
Sabinene 142 WP α , F β,γ , L γ EO T. balsamita α , T. vulgare α , T. macrophyllum γ GC-FID, GC–MS Italy α , Iran β , Türkiye γ Polatoğlu et al. (2015); Bączek et al. (2017); Farzadfar et al. (2017)
β-Myrcene 143 AP, L, F EO T. balsamita GC–MS Iran Monfared et al. (2002)
Limonene 144 AP EO T. balsamita GC–MS Türkiye Bagci et al. (2008)
Terpinolene 145 AP α , WP β EO T. chiliophyllum α , T. balsamita β GC–MS Türkiye α , Italy β Bagci et al. (2008), Bączek et al. (2017)
α-Thujene 146 AP α, β , WP γ EO T. chiliophyllum α , T. cilicicum β , T. balsamita γ , T. vulgare γ GC-FID Türkiye α, β , Italy γ Salamci et al. (2007), Bagci et al. (2008)
p-Cymene 147 F α , L α , AP β , WP γ EO T. polycephalum α , T. argenteum β , T. balsamita γ , T. vulgare γ GC–MS Iran α , Türkiye β,γ Nori-Shargh et al. (1999), Bączek et al. (2017)
Camphene 148 AP α , F β , L β , F γ , St γ EO T. chiliophyllum α , T. balsamita α , T.polycephalum β , T. kotschyi γ* GC–MS Iran α, β , Türkiye γ Nori-Shargh et al. (1999), Bagci et al. (2008), Polatoglu et al. (2011)
Verbenene 149 AP α EO T. chiliophyllum α , T. balsamita α GC–MS Iran α Bagci et al. (2008)
Tricyclene 150 AP α EO T. chiliophyllum α , T. balsamita α GC–MS Iran α Bagci et al. (2008)
α-Phellandrene 151 WP EO T. vulgare GC–MS Italy Bączek et al. (2017)
Santolinatriene 152 L α , F α , AP β EO T. argyrophyllum α , T. praeteritum β , T. santolinoides β GC–MS Türkiye Gören et al. (2001), El-Shazly et al. (2002)
β-Phellandrene 153 AP EO T. praeteritum GC–MS Türkiye Gören et al. (2001)
Oxygenated monoterpenes
1,8-Cineole 154 L α , F α , AP β EO T. argyrophyllum α , T. praeteritum β , T. argenteum α , T. balsamita β , T. chiliophyllum β , T. polycephalum α , T. cilicicum β GC–MS Türkiye, Iran Nori-Shargh et al. (1999), Gören et al. (2001), Bagci et al. (2008)
Dehydro-1,8-cineole 155 AP EO T. argyrophyllum, T. praeteritum GC–MS Türkiye Gören et al. (2001)
1,4-Cineole 156 WP EO T. balsamita GC–MS Italy Bączek et al. (2017)
α-Thujone 157 AP α , L β , WP γ EO T. santolinoides α , T. argyrophyllum β , T. praeteritum α , T. chiliophyllum α , T. vulgare γ GC–MS Türkiye α, β , Italy γ Gören et al. (2001), Salamci et al. (2007)
β-Thujone 158 AP α , L β , WP γ EO T. santolinoides α , T. argyrophyllum β , T. praeteritum α , T. chiliophyllum α , T. vulgare γ , T. balsamita γ GC–MS Türkiye α, β , Italy γ Gören et al. (2001), Salamci et al. (2007)
Camphor 159 WP α , L β , AP γ EO T. vulgare α , T. argyrophyllum β , T. praeteritum γ GC–MS Italy α , Türkiye β, γ Gören et al. (2001), Bączek et al. (2017)
Carvone 160 WP α , L β , F β EO T. balsamita α , T. vulgare α , T. argyrophyllum β GC–MS Italy α , Türkiye β Gören et al. (2001), Bączek et al. (2017)
cis-Dihydrocarvone 161 WP EO T. vulgare GC–MS Italy Bączek et al. (2017)
trans-Dihydrocarvone 162 L α , F α , WP β EO T. argyrophyllum α , T. vulgare β GC–MS Türkiye α , Italy β Gören et al. (2001), Bączek et al. (2017)
α-Terpineol 163 AP α , L β , F β EO T. santolinoides α , T. argyrophyllum β GC–MS Egypt α , Türkiye β Gören et al. (2001), El-Shazly et al. (2002)
Pinocarvone 164 WP EO T. balsamita GC–MS Italy Bączek et al. (2017)
Borneol 165
Eucalyptol 166
trans-Carveol 167 AP EO T. tabrisianum GC–MS Iran Habibi et al. (2007)
Dehydro-1,8-cineole 168 AP EO T. balsamita GC–MS Iran Monfared et al. (2002)
trans-carvyl acetate 165
cis-carvyl acetate 166
Lavandulol 167 AP EO T. paradoxum* GC–MS Iran Habibi et al. (2007)
Carvacrol 168 WP EO T. vulgare GC–MS Italy Bączek et al. (2017)
Thymol 169 AP EO T. sinaicum* GC–MS Egypt Elshamy et al. (2021)
Grandisol 170
Piperitone 171
Myrtenol 172 WP EO T. balsamita, T. vulgare GC–MS Italy Bączek et al. (2017)
cis-Piperitol 173
cis-Chrysanthenol 174
Dihydrocarveol 175
α-Campholenal 176
Filifolone 177 AP EO T. sinaicum GC–MS Türkiye Elshamy et al. (2021)
p-Menth-1-en-8-ol 188
Eugenol 189 AP EO T. chiliophyllum* GC–MS Türkiye Salamci et al. (2007)
Sesquiterpenes hydrocarbons
Copaene 190 AP EO T. cilicicum*, T. sinaicum GC–MS Türkiye Gecibesler et al. (2016), Elshamy et al. (2021)
β-Humulene 191
α-Calacorene 192 AP EO T. balsamita, T. chiliophyllum GC–MS Türkiye Bagci et al. (2008)
β-Funebrene 193
Ledene 194
Bicyclogermacrene 195
Germacrene D 196
Ar-Curcumene 197 AP EO T. chiliophyllum, T. aucherianum* GC–MS Türkiye Salamci et al. (2007)
γ-Cadinene 198
δ-Cadinene 199
Allo-Aromadendrene 200
β-Farnesene 201
β-Caryophylene 202
β-Cubebene 203
Valeranone 204 WP EO T. balsamita, T. vulgare GC–MS Italy Bączek et al. (2017)
α-Longipinene 205
Oxygenated sesquiterpenes
T-Muurolol 206 AP EO T. balsamita GC–MS Iran Monfared et al. (2002)
1,10-di-epi-Cubenol 207
β-Copaen-4-alpha-ol 208
Nerolidol 209
Cubebol 210
(Z)-Sesquilavandulol 211
trans-Isolongifolanone 212 AP EO T. tabrisianum* GC–MS Iran Habibi et al. (2007)
Caryophyllene oxide 213
Davana ether-1 214 AP EO T. sinaicum* GC–MS Egypt Elshamy et al. (2021)
Davana ether-2 215
Isoaromadendrene epoxide 216
Geranyl tiglate 217
Eudesm- 4(14)-en- 4-ol 218
Intermedeol 219 WP EO T. balsamita, T. vulgare GC–MS Italy Bączek et al. (2017)
β-Eudesmol 220
Longiverbenone 221
Acorenone B 222
Valeranone 223
Gleenol 224
Cadin-4-en-10-ol 225
β-Atlantone 226 AP EO T. balsamita, T. chiliophyllum GC–MS Türkiye Bagci et al. (2008)
Oplopenone 227
Ledol 228
Spathulenol 229
Isospathulenol 230
Hedycaryol 231
Diterpenes
Neophytadiene 232 AP EO T. balsamita, T. chiliophyllum GC–MS Türkiye Bagci et al. (2008)
Vulgarol A 233
α,β-Unsaturated aldehydes
(E)-2-Heptenal 234 Fl n-Hexane T. balsamita GC–MS Brazil Kubo and Kubo (1995)
(E)-2-Octenal 235
(E)-2-Nonenal 236
(E)-2-Decenal 237
(E)-2-Undecenal 238
(E,E)-2,4-Decadienal 239
3-Methyl-2-butenal 240
Hexanal 241

WP, whole plant; L, leaves; Fl, Flowers; St, Stems; Inf, Inflorescences; Pe, Petals; Flo: Floscules.

*T. aucherianum: Tanacetum aucherianum Sch.Bip.

*T. chiliophyllum: Tanacetum chiliophyllum var. chiliophyllum.

*T. sinaicum: Tanacetum sinaicum (Fresen.) Delile ex K.Bremer & Humphries.

*T. tabrisianum: Tanacetum tabrisianum (Boiss.) Sosn.& Takht.

*T. paradoxum: Tanacetum paradoxum Bornm.

*T. zahlbruckneri: T. zahlbruckneri (Nab.) Grierson.

*T. kotschyi: T. kotschyi (Boiss.) Grierson.