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Figure 1.
The morphology of the Gnaphalium affine and its processed products. (a), (b) The overground part of G. affine. (c) The pastry of G. affine, called qingtuan, also known as Qingming food.
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Figure 2.
Structures of flavones in genus Gnaphalium.
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Figure 3.
Structures of flavonols in genus Gnaphalium.
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Figure 4.
Chalcones and flavanones isolated from the genus Gnaphalium.
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Figure 5.
Structures of triterpenoids in genus Gnaphalium.
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Figure 6.
Diterpenoids isolated from the genus Gnaphalium.
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Figure 7.
Sesquiterpenoids isolated from the genus Gnaphalium.
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Figure 8.
Monoterpenoids isolated from the genus Gnaphalium.
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Figure 9.
Phenolic acids isolated from the genus Gnaphalium.
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Figure 10.
Steroids and sterols isolated from the genus Gnaphalium.
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Figure 11.
Alkaloids isolated from the genus Gnaphalium.
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Figure 12.
Other compounds isolated from the genus Gnaphalium.
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Gnaphalium species Country Ethnopharmalogical uses Reference G. affine China, Mexico,
Latin AmericaPhlegm-removing, anemopyretic cold, antibacterial, bronchitis, chronic obstructive pulmonary diseases, antihypertensive, ulcer, antitussive, expectorant, antiasthmatic, bronchial asthma, respiratory disease, diuretics, antipyretics and antimalarials, wound, backache, coronarism. [8−24] G. hypoleucum China Inflammation, cough, gout, expectorant. [25] G. polycaulon China Clear heat and dampness. [26] G. japonicum China Promoting blood circulation to relieve pain, promoting dampness, treating acne, irregular menstruation, abdominal pain and dysentery during menstruation, clearing away heat and toxins. [27,28] G. adnatum China Treat Helicobacter pylori. [29] G. uliginoshisum Russia, Bulgaria Hypertension, thrombophlebitis, venous thrombosis, ulcer. [30,31] G. stramineum Guatemala Gastrointestinal diseases. [32] G. gaudichaudianum Latin America, Argentina Subcutaneous mycoses, expectorant, hemostasis. [33,34] G. liebmannii Mexico Asthma, cough, bronchitis. [35] Table 1.
Ethnopharmacological uses of reported Gnaphalium species.
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No. Compound Source Reference Flavones 1 Apigenin 4'-O-β-D-(6''-E-caffeoyl)-glucopyranoside G. affine [3,5] 2 Gnaphaloside A G. tranzschelii [5] 3 Apigenin-7-O-β-D-glucopyranoside G. tranzschelii, G. luteoalbum [3,5] 4 Chrysoeriol-7-O-β-D -glucopyranoside G. uliginosum [3] 5 Apigenin-7-O-β-D-glucuronic acid methylester G. affine, G. hypoleucum [5,38] 6 Apigenin G. affine, G. hypoleucum [36−38] 7 Luteolin-4'-O-β-D-glucopyranoside G. affine, G. cheiranthifolium, G. hypoleucum,
G. luteoalbum[37,38] 8 5-hydroxy-4',7-dimethoxyflavonoid G. affine [38] 9 Acacetin G. affine [38] 10 Luteolin G. affine, G. hypoleucum, H. polycaulon,
G. luteoalbum, G. rufescens, G. sylvaticum,
G. oxyphyllum[36−38] 11 Chrysin G. affine [38] 12 5-hydroxy-6,7,3',4'-tetramethoxyflavone G. affine [39] 13 Luteolin-7-O-β-D-glucuronide methyl ester G. hypoleucum [3] 14 6-Hydroxyluteolin-7-O-β-D-glucopyranoside G. hypoleucum, G. affine, G. tranzschelii [5,40] 15 Acacetin-7-O-rutinoside G. affine [3] 16 Eupafolin-7-O-β-D-glucopyranoside G. affine [3] 17 5,7,4'-trihydroxy-6,3'-dimethoxyflavone G. luteoalbum [3] 18 6-MethoxyLuteolin G. uliginosum, G. tranzschelii [3,5] 19 Luteolin-7-O-β-D-glucopyranoside G. luteoalbum, G. hypoleucum [3,5] 20 Apigenin-4'-O-β-D-glucopyranoside G. affine [3] 21 5,7,4'-trihydroxy-3',5'-dimethoxyflavone G. sylvaticum [3] 22 Linarin G. hypoleucum [3] 23 Luteolin-7-O-β-D-glucuronide G. hypoleucum [3] 24 Acacetin-7-O-β-D-xylopyranosyl-[α-L- rhamnopyranosyl]-β-D-glucopyranoside G. hypoleucum [3] 25 Luteolin 4'-O-β-D-(6''-E-caffeoyl)-glucopyranoside G. hypoleucum, G. affine [3,5] 26 5,7,3',4'-Tetrahydroxy-6-methoxyflavonoid-7-O-
β-D-(6''-E-caffeoyl)-glucopyranosideG. tranzschelii [5] 27 Luteolin 7-O-methyl ether G. rufescens [5] 28 5,7,3',4'-tetrahydroxy-6-methoxyflavonoid-7-O-β-
D-glucopyranosideG. tranzschelii [5] 29 5-hydroxy-7,8-dimethoxyflavone G. pellitum [5] 30 Hispidulin G. antennarioides [5] 31 Velutin G. gaudichaudianum [5] 32 5,8-dihydroxy-6,7-dimethoxyflavone G. gaudichaudianum [5] 33 Hispidulin 7-O-β-D-glucopyranoside G. antennarioides [5] 34 Jaceosidin G.luteoalbum, G.tranzschelii [5] 35 3,5,7,4'-tetrahydroxy-3'-methoxyflavonoid-7-O-β-D-glucopyranoside G. tranzschelii [5] 36 8-O-(2-methylbutyryl)-5,7,8-trihydroxyflavone G. robuscum [5] 37 8-O-[(Z)-2-methyl-2-butenyl]-5,7,8-trihydroxyflavone G. robuscum [5] 38 Eupatilin G. affine [39] 39 5,7,4'-Trihydroxy-3'-methoxyflavonoid-
7-O-β-D-(6''-O-caffeoyloxy)-glucopyranosideG. affine, G. uliginosum [38] 40 Apigenin 7-O-β-D-(6''-E-caffeoyl)-glucopyranoside G. affine [3,5] Flavonols 41 5,7-dihydroxy-3,8,4'-trimethoxyflavonoid G. hypoleucum, G. affine [38,40] 42 Tiliroside G. adnatum [41] 43 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone G. affine, G. hypoleucum [2] 44 Kaempferol 3-O-β-D-(6''-O-coumarin)-glucopyranoside G. affine [42] 45 Isorhamnetin-7-O-β-D-glucopyranoside G. affine [38] 46 Quercetin 4'-O-β-D-(6''-E-caffeoyl)-glucopyranoside G. hypoleucum, G. affine [3,5] 47 Isorhamnetin-3-O-β-D-galactopyranoside G. uliginosum [3] 48 Patuletin-3-O-β-D -glucopyranoside G. uliginosum [3] 49 5,7,3',4'-Tetrahydroxy-3-methoxyflavonoid G. indicum [3] 50 5,7-dihydrox-3,8-dimethoxyflavone G. gracile [3] 51 3-Methoxyquercetin G. gracile [3] 52 7-Methoxyquercetin G. pellitum [3] 53 5,8-Dihydroxy-3,6,7,4'-tetramethoxyflavonoid G. affine [42] 54 Quercitrin G. affine, G. sylvaticum [5] 55 8-O-(2-methylbutyrate)-5,7-dihydroxy 3-methoxyflavonoid G. robustum [3] 56 Quercimeritrin G. hypoleucum [43] 57 Quercetin-3-O-β-D-galactopyranoside G. hypoleucum [43] 58 5-hydroxy-3,7-dimethoxyflavone G. uiscosum [42] 59 Rhamnetin G. pellitum, G. affine [5,38] 60 Quercetin G. affine, G. gracile, G. hypoleucum, G. polycaulon,
H. pellitum, G. sylvaticum, I. G. uniflorum[36−38] 61 Kaempferol-3-O-β-D-glucopyranoside G. affine, G. uniflorum [5,38] 62 5-Hydroxy-3,6,7,8,4'-pentamethoxyflavone G. affine, G. hypoleucum [38] 63 5,6-dihydroxy-3,7-dimethoxyflavone G. affine [38] 64 Baicalein-7-O-β-D-glucopyranoside G. tranzschelii [5] 65 Isokaempferol G. dioicum [5] 66 Quercetin 4'-O-β-D-glucopyranoside G. affine, G. hypoleucum [5,40] 67 Isoquercitrin G. stramineu, G. sylvaticum, G. tranzschelii, G.uniflorum [5] 68 Quercetagetin G. affine [5] 69 Quercetin 3-O-β-D-galactopyranoside-4'-O-β-D-glucopyranoside G. uniflorum, G. affine [5] 70 Quercetagetin 7-O-β-D-glucopyranoside G. affine [5] 71 Isorhamnetin G. affine, G. hypoleucum [5] 72 3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-β-D-glucopyranoside G. tranzschelii [5] 73 3,5,7,3',4'-Pentahydroxy-6-methoxyflavone-3-O-β-D-glucopyranoside G. tranzschelii [5] 74 Gnaphaliin B G. affine, G. liebmannii [5] 75 3,5-dihydroxy-6,7,8-trimethoxyflavone G. chilense, G. microecephalum, G. robustum [5] 76 3,5-Dihydroxy-6,7,8,4'-tetramethoxyflavone G. affine [5] 77 5-Hydroxy-3,7,8-trimethoxyflavone G. affine, G. robustum, G. obtusifolium [5] 78 5-hydroxy-3,6,7,8-tetramethoxyflavonoid G. affine, G. hypoleucum,G. undulatum [5] 79 Gnaphaliin A G. affine, G. gracile, G. lanuginosum,
G. liebmannii, G. obtusifolium, G. robustum[5] 80 5,7-Dihydroxy-3-methoxyflavonoid G. gracile, G. robustum [5] 81 8-O-(2-methyl-2-butenyl)-5,7-dihydroxy-3-methoxyflavonoid G. robustum [5] 82 5,7-dihydroxy-3,6-dimethoxyflavone G. wrightii [5] 83 5,8-dihydroxy-3,6,7-trimethoxyflavone G. affine, G. gaudichaudianum [5] 84 5,7-Dihydroxy-3,6,8-trimethoxyflavone G. affine, G. elegans [5] 85 5,7-Dihydroxy-3,8,3',4'-tetramethoxyflavone G. affine [5] 86 3,5,7-trihydroxy-6,8-dimethoxyflavone G. obtusifolium [5] 87 5,7,8-Trihydroxy-3-methoxyflavonoid G. robuscum [5] 88 Quercetin 3-methyl ether G. gracile, G. indicum [5] Chalcones 89 2',4',4-Trimethoxy-6'-methoxychalcone G. affine [5] 90 Gnaphalin G. affine, G. cheiranthifolium, G. multiceps,
G. purpurascens, G. luteoalbum, G. hypoleucum[5] 91 2',4,4'-trihydroxy-6'-methoxychalcone G. affine [38] 92 4,4'，6'-Trimethoxy-2'-methoxychalcone G. affine [38] 93 2',4'-dihydroxy-4,6'-dimethoxychalcone G. affine [38] 94 2'-hydroxy-4,4',6'-trimethoxychalcone G. affine [38] 95 4,2',4',6'-Tetramethoxychalcone G. affine [38] 96 2',4,4'-trihydroxy-6'-methoxychalcone-4-glucopyranoside G. affine [3] Flavanones 97 Naringenin-7-O-β-D-(6''-E-caffeoyl)-glucopyranoside G. affine [42] 98 Taxifolin G. affine [42] 99 Dihydroapigenin G. affine [38] 100 Pinocembrin G. purpurascens [5] 101 Wogonin G. affine [38] 102 4'-Hydroxy-5-methoxy-7-O-β-D-glucopyranosyl-dihydroflavanone G. hypoleucum [43] 103 7,4'-Dihydroxy-5-Methoxydihydroflavonoids G. hypoleucum [43] 104 5,7,3',4'-tetrahydroxyflavone G. affine [42] Triterpenoids 105 β-Amyrin G. affine [5,38] 106 β-amyrin acetate G. affine [38] 107 Oleanolic acid G. affine, G. hypoleucum [38] 108 Friedelin G. affine [38] 109 α-Amyrin G. affine [5,38] 110 Ursolic acid G. affine, G. hypoleucum [38] 111 α-amyrin acetate G. affine [38] 112 Faradiol 3-O-palmitate G. affine [44] 113 19α-hydroxy ursolic acid G. affine, G. hypoleucum [38] 114 2α,3α,19α-trihydroxy-28-norurs-12-ene G. affine [38] 115 Taraxasterol G. affine [38] 116 Taraxasterol acetate G. affine [5,38] 117 Lupeone G. affine [38] 118 Betulonic acid G. affine [44] 119 Betulinic acid G. affine [5] 120 Squalene G. gaudichaudianum [5] Diterpenoids 121 Ent-pimara-8(14),15-dien-3a,19-diol G. affine [45] 122 Ent-pimara-8(14),15-dien-3α-ol G.affine [38] 123 Ent-pimara-8(14),15-dien-19-ol G. affine [38] 124 Ent-Pimara-8(14),15-diene-19-ol G. gaudichaudianum [5] 125 Ent-pimara-8(14),15-dien-19-oic acid G. gaudichaudianum [5] 126 Ent-pimara-8(14),15-dien-18-oic acid G.gaudichaudianum [5] 127 Ent-Pimara-8(14),15-diene-3α,19-diol G. gaudichaudianum [5] 128 Sclareol G. gaudichaudianum [5] 129 8α,13α-Diacetoxycinnamyl alcohol G. gaudichaudianum [5] 130 8-epi-Sclareol G. undulatum [5] 131 8-epi-Eni-sclareol G. gaudichaudianum [3] 132 Kaur-16-en-19-oic acid G. gaudichaudianum, G. inornatum, G. rufescens [5] 133 Methyl kaur-16-en-19-oate G. gaudichaudianum [5] 134 3α-hydroxykaur-16-en-19-oic acid G. gaudichaudianum [3,5] 135 Methyl 3α-hydroxykaurl-16-en-19-oate G. gaudichaudianum [5] 136 11β-Acetoxycoel-16-ene-19-oleic acid G. rufescens [5] 137 Methyl 3α-acetoxycol-16-ene-19-oate G. gaudichaudianum [5] 138 3α-Acetoxycol-16-ene-19-oleic acid G. gaudichaudianum [5] 139 Ent-Kauran-16-ene G. undulatum [5] 140 Ent-Kaur-16-en-19-al G. undulatum [5] 141 Ent-Kaur-16-en-19-oic acid G. affine, G. graveolens, G. oligandrum, G. pellitum,
G. undulatum, G. oxyphyllum, G. liebmannii[5] 142 15α-hydroxy-ent-kaur-16-en-19-oleic acid G. undulatum, G. viscosum [5] 143 11β-acetoxy-ent-kaur-16-en-19-oleic acid G. pellitum [5] 144 (−)-16-Kaurene-19-oic acid G. affine [3] 145 (−)-Methyl kaur-16-en-19-oate G.gaudichaudianum [3] 146 (3α,4α)-Kaur-16-en-18-oic acid-3-hydroxy-methyl ester G. gaudichaudianum [3] 147 3α-acetoxykaur-16-en-19-oic acid Me ester G. gaudichaudianum [3] 148 Ent-pimar-15-ene-8α,19-diol G. gaudichaudianum [5] 140 Ent-pimar-15-ene-3α,8α-diol G. gaudichaudianum [5] 150 Zoapatlin G. hypoleucum, G. affine, G. oxyphyllum,
G. liebmannii, G. viscosum[40] 151 Ent-3β-hydroxykaur-16-en-19-oic acid G. affine, G. viscosum [38] 152 (−)-11β-Acetoxy-16-kaurene-19-oic acid G. affine [3] 153 Kauranol G. rufescens [5] 154 Ent-Kaur-9(11),16-en-19-oic acid G. oligandrum, G. undulatum [5] 155 Sylviside G. sylvaticum [5] 156 Carnoside G. sylvaticum [3] 157 15β-hydroxy-Wedeliaseccokaurenolide G. undulatum [5] Sesquiterpenoids 158 Gemamane D G. oligandrum [5] 159 (2E,6Z)-7,11,11-trimethylbicyclo[8,1,0]undec-2,6-diene diterpene G. oligandrum [5] 160 γ-Cadinene G. affine [46] 161 (E)-β-Farnesene G. pensylvanicum [36] 162 Irisone G. pensylvanicum [36] 163 (−)-β-Elemene G. affine [48] 164 α-Gurjunene G. affine [48] 165 Trans-Caryophyllene G. affine [21] 166 α-Humulene G. affine [48,49] 167 δ-Cadinene G. affine [48] 168 α-elemol G. affine [48] 169 β-selinene G. affine [8] 170 γ-Gurjunene G. japonicum, G. affine [49] 171 Corchoionol C G. affine [38, 50] 172 Caryophyllene oxide G. affine, G. japonicum [51] 173 6,10,14-trimethyl-2-Pentadecanone G. affine [52] 174 Nerolidol G. affine [51] 175 1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene G. affine [51] 176 Aromadendrene G. affine, G. japonicum, G. pensylvanicum [8] 177 7R,8R-8-hydroxy-4-isopropylidene-7-methylbicyclo[5,3,1] undec-1-ene G. japonicum [46] Monoterpenoids 178 α-Terpineol G. affine [21] 179 Linalool G. affine [21] 180 p-cymene G. affine [21] 181 m-cymene G. affine [48] 182 Pulegone G. affine [52] Phenolic acids 183 Protocatechuic acid G. affine [46] 184 Caffeic acid G. affine [46] 185 Ethyl Caffeate G.affine [38] 186 Ethyl protocate G.affine [38] 187 Trans caffeic acid G. tranzschelii [5] 188 Caffeic acid ethylene ester G. hypoleucum [40] 189 Eugenol G. affine [36, 21] 190 Coniferylaldehyde G. affine [38] 191 P-hydroxycinnamic acid G. affine [38] 192 Methyl cinnaminate G. hypoleucum [47] 193 Isovanillin G. affine [38] 194 Isovanillic acid G. affine [38] 195 3',5-dihydroxy-2- (4-hydroxybenzyl) -3-methoxybibenzyl G. affine [44] 196 Everlastoside L G. affine [38] 197 Methyl p-hydroxycinolinate glucoside G. affine [38] 198 Acteoside G. affine [44] 199 1,4,5-tri-O-caffeoylquinic acid G. affine [38] 200 1,5-di-O-caffeoylquinic acid G. affine [38] 201 1,5-dicaffeoylquinic acid methyl ester G. affine [38] 202 1,3-di-O-caffeoylquinic acid G. affine [38] 203 3,5-di-O-caffeoylquinic acid G. affine [20] 204 3,4-di-O-caffeoylquinic acid G. affine [20] 205 1,4-di-O-caffeoylquinic acid G. affine [42] 206 Chlorogenic acid G. affine [46] 207 4-O-caffeoylquinic acid G. stramineum [5] 208 4,5-di-O-caffeoylquinic acid G. stramineum [5] 209 3,4,5-tri-O-caffeoylquinic acid G. stramineum [5] Steroids and sterols 210 Daucosterol G. affine, G. adnatum, G. hypoleucum [50] 211 Stigmasterol G. affine, G. adnatum, G. gaudichaudianum,
G. viscosum, G. oxyphyllum, G. liebmannii[38] 212 β-sitosterol G. affine, G. hypoleucum, G. inornatum, G. pellitum,
G. oxyphyllum, G. liebmannii, G. viscosum[38] 213 Stigmasta-4,22-dien-3-one G. affine, G. adnatum [38] 214 4-Cholesten-3-one G. affine [5] 215 3β-hydroxy-stigmasta-5,22-dien-7-one G. affine [5] 216 α-spinasterol G. affine [38] Alkaloids 217 Grossamiade K G. affine [44,38] 218 Aurantiamide acetate G. hypoleucum [3] 219 Matrine G. sphacelatum [5] 220 Scopolamine G. affine [5] 221 Anabellamide G. affine [38] 222 Patriscabratine G. affine [38] 223 Longumoside A G. affine [44] Others 224 Phloroglucinol G. affine [53] 225 3-methoxyphenol1-O-α-L-rhamnopyranosyl-4-
(1→6)-O-β-D-glucopyranosideG. affine [38] 226 2,3,5,4'-tetrahydtoxysilbene-2-O-β-D-glucopyranoside G. affine [50] 227 (Z)-3-hexenyl O-β-D-glucopyranoside G. polycaulon [5] 228 Gnaphalium A G. affine [54] 229 Gnaphaliol 3-O-β-D-glucopyranoside G. polycaulon [5] 230 Gnafaliol 9-O-β-D-glucopyranoside G. polycaulon [5] 231 (+)-Pinenutol G. pellitum [5] 232 Panamin G. hypoleucum [40] 233 Tithoniamide B G. affine [50] 234 4'-Hydroxydehydrogenase G. hypoleucum [3] 235 Anaphatol G. affine, G. adnatum [38,41] 236 7-O-(β-D-glucopyranosyl)-5-hydroxyisobenzofuran-1(3H)-one G. affine, G. adnatum [38,41] 237 4-(3',4'-dimethoxyphenyl)-3-methyl-butyl-3-ene-2-one G. affine, G.adnatum [38] 238 Desmethylyangonine-4'-glucopyranoside G. affine [38] 239 3-(4'-formylphenoxy)-4-methoxybenzaldehyde G. affine [38] 240 3-Hydroxydihydrobenzofuranose G. polycaulon [55] 241 Gnaphaliol 9-O-β-D-glucopyranoside G. polycaulon [55] 242 5,7-dihydroxyl-isobenzofuran-1(3H)-one G. affine, G. adnatum [41] 243 1-Hexacosanol G. affine [38] 244 Gnaohaliin C G. hypoleucum [3] 245 Benzeneacetaldehyde G. affine [48] 246 1-Tetratriacontanol G. affine [50] 247 Adenosine G. polycaulon [5] 248 4-hydroxyacetophenone G. affine [56] 249 Diethyl phthalate G. affine [38] 250 Diisobutyl phthalate G. pensylvanicum [36] 251 Dimethyl phthalate G. japonicum [46] 252 9,16-dixo-10,12,14-octadeca-trienoic acid G. affine [56] 253 N-hexacosanic acid G. affine [5] 254 Myristicin aldehyde G. affine, G. japonicum [46] 255 N-butyl-isobutyl terephthalate G. adnatum, G. affine [41,48] 256 1-Palmitoyl-rac-glycerol G. affine [50] 257 4'-hydroxydehydrokawain G. affine [38] Table 2.
Compounds isolated and identified from the Gnaphalium L.
Figures
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Tables
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