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. 2020 Sep 28;266:113415. doi: 10.1016/j.jep.2020.113415

Table 3.

The alkynes and their glycosides from Atractylodis Rhizoma.

Chemical compounds Nos. Compounds name Structure Origin and Ref.
Polyacetylenes of diene-diyne types and their glycosides 86 atractylodin
2-[(1E,7E)-nona-1,7-dien-3,5-diynyl]furan		 Image 87 A. lancea (Takeda, 1994);
A. chinensis (Nishikawa et al., 1975);
A. lancea (Kawanishi, 1994);
A. koreana (Kawanishi, 1994)
87 (1Z)-atractylodin
2-[(1Z,7E)-nona-1,7-dien-3,5-diynyl]furan		 Image 88 A. lancea (Resch et al., 2001)
88 9-nor-atractylodin Image 89 A. lancea (Chen et al., 2012)
89 atractylodinol [(2E,8E)-9-(furan-2-yl)nona-2,8-dien-4,6-diyn-1-ol] Image 90 A. lancea, A. chinensis (Nishikawa et al., 1976)
90 (1Z)-atractylodinol [(2E,8Z)-9-(furan-2-yl)nona-2,8-dien-4,6-diyn-1-ol] Image 91 A. chinensis (Meng et al., 2010)
91 acetylatractylodinol
[(2E,8E)-9-(furan-2-yl)nona-2,8-dien-4,6-diynyl] acetate		 Image 92 A. lancea, A. chinensis (Nishikawa et al., 1976)
92 (1Z)-acetylatractylodinol
[(2E,8Z)-9-(furan-2-yl)nona-2,8-dien-4,6-diynyl] acetate		 Image 93 A. lancea (Resch et al., 2001)
93 (6E,12E)-tetradecadiene-8,10-diyne-1,3-diol Image 94 A. chinensis (Meng et al., 2010);
A. japonica (Jeong et al., 2010);
Atractylodis Rhizoma (Sakurai et al., 1994b)
94 (6E,12Z)-tetradecadiene-8,10-diyne-1,3-diol Image 95 A. chinensis (Meng et al., 2011)
95 (6Z,12Z)-tetradecadiene-8,10-diyne-1,3-diol Image 96
96 (6E,12E)-tetradecadiene-8,10-diyne-1,3-diol diacetate Image 97 A. chinensis (Meng et al., 2010)
97 (6E,12E)-3-acetoxytetradeca-6,12-dien-8,10-diyn-1-ol Image 98
98 (6E,12E)-1-acetoxytetradeca-6,12-dien-8,10-diyn-3-ol Image 99
99 1,4-acetoxytetradeca-6,12-diene-8,10-diyne Image 100 Atractylodis Rhizoma (Sakurai et al., 1994a)
100 diacetyl atractylodiol [(5E,11E)-3-acetyloxytrideca-5,11-dien-7,9-diynyl] acetate Image 101 A. japonica (Yosioka et al., 1974)
101 (2E,8E)-decadiene-4,6-diyne-1,10-diol 1-O-β -D-glucopyranoside Image 102 A. lancea (Kitajima et al., 2003b)
102 atractylodinol [1-(2-Furyl)-(1E,7E)-nonadiene-3,5-diyne-9-ol] Image 103 A. lancea (Chen et al., 2012)
103 1-(2-Furyl)-(1E,7E)-nonadiene-3,5-diyne-9-al Image 104
104 1-(2-Furyl)-(1E,7Z)-nonadiene-3,5-diyne-9-ol Image 105
105 1-(2-Furyl)-(1E,7E)-nonadiene-3,5-diyne-9-yl benzoate Image 106
106 1-(2-Furyl)-(1E,7E)-nonadiene-3,5-diyne-9-yl 4-methylbenzoate Image 107
107 1-(2-Furyl)-(1E,7E)-nonadiene-3,5-diyne-9-acid Image 108
108 (1Z)-atractylodinol 1-(2-Furyl)-(1Z,7E)-nonadiene-3,5-diyne-9-ol Image 109 A. lancea (Resch et al., 2001)
109 (1Z)-acetylatractylodinol 1-(2-Furyl)-(1Z,7E)-nonadiene-3,5-diyne-9-yl acetate Image 110
110 (4E,10E)-dodeca-4,10-dien-6,8-diyne-1,3-diyl diacetate Image 111 A. lancea (Meng et al., 2010)
111 (6E,12E)-aetradecadiene-8,10-diyne-1,3-diol Image 112
112 (2E,8Z)-deca-2,8-diene-4,6-diyne-1,10-diol-1- O-β-D-glucopyranoside Image 113 A. lancea (Xu, 2017)
113 (2E,8E)-deca-2,8-diene-4,6-diyne-1,10-diol-1-O-β-D-apiofuranosyl-(1 → 6) -β-D-glucopyranoside Image 114
114 (2E,8Z)-deca-2,8-diene-4,6-diyne-1,10-diol-1-O-β-D-apiofuranosyl-(1 → 6) -β-D-glucopyranoside Image 115
115 (8R,9S)-2E,10Z-tridecadiene-4,6-diyne-8,9,12,13-triol-9-O-β-D-glucopyranoside Image 116
116 (8R,9S)-2E,10Z-tridecadiene-4,6-diyne-8,9,12,13-triol-8-O-β-D-glucopyranoside Image 117
117 (8R,9S)-2E,10Z-tridecadiene-4,6-diyne-8,9,12,13-triol Image 118
118 (2Z,8E)-deca-2,8-diene-4,6-diyne-1,10-diol-1-O-β-D-glucopyranoside Image 119
119 (2E,8E,10R)-tridecatriene-4,6-diyne-1,10,11,12,13-pentol-10-O-β-D-glucopyranoside Image 120
120 (2E,8E,10R)-tridecane-2,8-diene-4,6-diyne-1,10, 13-di-O-β-D-xylopyranoside Image 121
121 (3R,8E,10E)-tetradecadiene-4,6-diyne-3,12,14-triol-3-O-β-D-glucopyranoside Image 122
122 (2E,8E,12S)-tetradecadiene-4,6-diyne-1,10,14-triol-1-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 123
Triene-diyne types of atractylodes polyacetylenes and their glycosides 123 (1,3Z,11E)-Tridecatriene-7,9-diyne-5-hydroxyl-6-O-β-D-glucopyranoside Image 124 A. lancea (Ji et al., 2010)
124 atractyloyne [(3S,4E,6E,12E)-1-isovaleryloxy-tetradeca-4,6,12-triene-8,10-diyne-3,14-diol Image 125 A. chinensis (Nakai et al., 2005); Atractylodis Rhizoma (Kim, 2016)
125 12,14- diacetate- 2E,8E,10E- trien- 4,6-diyn-1-ol Image 126 Atractylodis Rhizoma (Kim, 2016)
126 (4E,6E,12E)-tetradecatriene-8,10-diyne-1,3-diyl diacetate Image 127 A. lancea (Resch et al., 2001)
127 (4E,6E,12E)-Tetradecatriene-8,10-diyne-1,3-diol Image 128
128 (4E,6E,12E)-Tetradecatrien-8,10-diyn-1-ol Image 129
129 (4E,6E,12E)-3-isovaleryloxy-tetradeca-4,6,12-triene-8,10-diyne-1,14-diol Image 130
130 erythro-(1,3Z,11E)-tridecatriene-7,9-diyne-5,6-diyl-diacetate Image 131
131 erythro-(1,5E,11E)-tridecatriene-7,9-diyne-3,4-diacetate Image 132 A. lancea (Lehner et al., 1997)
132 threo-(1,5E,11E)-tridecatriene-7,9-diyne-3,4-diacetate Image 133
133 (1,5E,11E)-trideca-1,5,11-trien-7,9-diyne-3,4-diacetate Image 134 Atractylodis Rhizoma (Kim, 2016)
134 (3Z,5E,11E)-tridecatriene-7,9-diynyl-1-O-(E)-ferulate Image 135 A. lancea (Resch et al., 2001)
135 (3E,5E,11E)-tridecatriene-7,9-diyne-l,2-diacetate Image 136 A. lancea (Lehner et al., 1997)
136 (3Z,5E,11E)-tridecatriene-7,9-diyne-1,2-diacetate Image 133 A. lancea (Resch et al., 2001)
137 (3E,5Z,11E)-tridecatriene-7,9-diyne-1,2-diacetate Image 138 A. lancea (Lehner et al., 1997)
138 (2Z,4E,10E)-trideca-2,4,10-trien-6,8-diynyl acetate Image 139 Atractylodis Rhizoma (Kim, 2016)
139 (1,5E,11E)-tridecatriene-7,9-diyne-3,4-diacetate Image 140 A. lancea (Resch et al., 2001)
140 (3E,5Z,11E)-tridecatriene-7,9-diyne-1,2-diyl diacetate Image 141
141 (4E,6E,12E)-aetradecatrien-8,10-diyn-1-ol Image 142 A. lancea (Meng et al., 2010)
142 (4E,6E,12E)-tetradeca-4,6,12-trien-8,10-diyne-1,3,14-triol Image 143 Atractylodis Rhizoma (Kim, 2016)
143 (4E,6E,12E)-tetradecadiene-triene-8,10-diol Image 144 A. lancea (Meng et al., 2010)
144 (5E,11E)-trideca-1,5,11- trien-7,9-diyne-3,4- diyldiacetate Image 145 Atractylodis Rhizoma (Kim, 2016)
145 (4E,6E,12E)-1-acetoxy-3-isovaleryloxy-4,6,12-trien-8,10-diyn-14-ol Image 146
146 (4E,6E,12E)-1-acetoxy-3-(2-methylbutyryloxy)-4,6,12-trien-8,10-diyn-14-ol Image 147
147 (8S,9R)-2E,10Z,12-tridecadiene-4,6-diyne-1,8,9-triol-8-O-β-D-glucopyranoside Image 148 A. lancea (Xu, 2017)
148 (8S,9R)-2E,10Z,12-tridecadiene-4,6-diyne-1,8,9-triol-8-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 149
149 (8S,9R)-2E,10Z,12-tridecadiene-4,6-diyne-1,8,9-triol-9-O-β-D-glucopyranoside Image 150
150 (8S,9R)-2E,10Z,12-tridecadiene-4,6-diyne-1,8,9-triol-9-O-β-D-apiofuranosyl-(1 → 6) -β-D-glucopyranoside Image 151
151 (10R,11R)-2R,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-10-O-β-D-glucopyranoside Image 152
152 (10R,11R)-2E,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-1-O-β-D-glucopyranoside Image 153
153 (10R,11R)-2E,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-1,10-O-di-β-D-glucopyranoside Image 154
154 (10R,11R)-2E,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-10-O-β-D- apiofuranosyl-(1 → 6) -β-D-glucopyranoside Image 155
155 (10R,11S)-2R,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-10-O-β-D-glucopyranoside Image 156
156 (10R,11S)-2E,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-10-O-β-D- apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 157
157 (10S,11R)-2E,8E,12-tridecatriene-4,6-diyne-1,10,11-triol-10-O-β-D-glucopyranoside Image 158
158 (2E,8E,10E,12R)-tridecatriene-4,6-diyne-1,12,13-triol-1,12-di-O-β-D-glucopyranoside Image 159
159 (2E,8E,10E,12R)-tridecatriene-4,6-diyne-1,12,13-triol-1-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 160
160 (8E,10E)-tetradecadiene-4,6-diyne-3,12,14-triol-3-O-β-D-glucopyranoside Image 161
161 (2E,8E,10E,12R)-tetradeca-2,8,10-triene-4,6-diyne-1,2,14-triol-1-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 162
162 (2E,8E,10E,12R)-tetradeca-2,8,10-triene-4,6-diyne-1,12,14-triol-1-O-β-D-glucopyranoside Image 163
Monoene-diyne types of aractylodes polyacetylenes and their glycosides 163 1-(2-Furyl)-(7E)-nonene-3,5-diyne-1,2-diacetate Image 164 A. lancea (Lehner et al., 1997); Atractylodis Rhizoma (Kim, 2016)
164 (2E)-decene-4,6-diyne-1,8-diol8-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 165 A. lancea (Kitajima et al., 2003b)
165 (2E,8R)-decane-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside Image 166 A. lancea (Xu, 2017)
166 (2E,8S)-decane-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside Image 167
167 (2E,8R)-decene-4,6-diyne-1,8-diol-1-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 168
168 (2E,8R)-decane-4,6-diyne-1,8-diol-O-di-β-D-glucopyranoside Image 169
169 (E)-deca-2-ene-4,6-diyne-1,10-diol-1-O-β-D-glucopyranoside Image 170
170 (E)-deca-2-ene-4,6-diyne-1,10-dio1-1-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 171
171 (2E,10S)-tridecane-2-ene-4,6-diyne-1,10,13-triol-1,13-di-O-β-D-xylopyranoside Image 172
172 (2E,10S)-tridecatriene-4,6-diyne-1,12,13-triol-13-O-β-D-glucopyranoside Image 173
173 (2E,10S)-tridecatriene-4,6-diyne-1,12,13-triol-10-O-β-D-glucopyranoside Image 174
174 (8R,9R)-8,9-dihydroxylatractylodinol-8-O-β-D-glucopyranoside Image 175
175 (8R,9R)-8,9-dihydroxylatractylodinol-9-O-β-D-glucopyranoside Image 176
176 (2E,10S)-tetradecadiene-4,6-diyne-1,10,14-triol-10-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside Image 177
177 1-(2-furyl)-(7E)-non-ene-3,5-diyne-l,2-diacetate Image 178
Other alkynes and their glycosides 178 (10R)-atracthioenyneside A Image 179 A. lancea (Xu, 2017)
179 (10R)-atracthioenyneside B Image 180
180 (10S,11R)-atracthioenyneside C Image 181
181 (10S,11R)-atracthioenyneside D Image 182
182 (10R,11S)-atracthioenyneside E Image 183
183 (8S)-decane-4,6-diyne-1,8-diol-O-β-D-glucopyranoside Image 184
184 2,8-dimethyl-6-hydroxy-2-(4-methyl-3-pentenyl)-2H-chromene Image 185 A. lancea (Resch et al., 1998)
185 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-methyl-2,5-cyclohexadiene-1,4-dione Image 186
186 2-[(2′E)-3′,7′-dimethyl-2′,6′-octadienyl]-4-methoxy-6-methylphenol Image 187
187 bis (5-[(1E,7E)-nona-1,7-dien-3,5-diyn-1-yl)]furan-2-yl)methane Image 188 A. lancea (Chen et al., 2012)
188 bis (5-[(1E,7E)-nona-1,7-dien-3,5-diyn-1-yl)]furan-2-yl)isopropane Image 189
189 (4E,6E,12E)-1-acetoxy-3-senecloyloxytetradeca-4,6,12-trien-8,10-diyn-14-ol Image 190 Atractylodis Rhizoma (Kano et al.)