|
No | Compounds | Species | References |
|
Alkaloids |
1 | Asimilobine | M. mollis twig | [24] |
2 | Coclaurine | M. balansae stem | [26] |
3 | Dehydroxylopine | M. cuneata stem and leaf | [21] |
4 | 1,9-Dihydroxy-2,11-dimethoxy-4,5-dihydro-7-oxoaporphine | M. cuneata stem and leaf | [21] |
5 | 2,10-Dimethoxy-3,11-dihydroxy-5,6-dihydroprotoberberine | M. cuneata stem and leaf | [21] |
6 | N,O-Dimethylharnovine | M. cuneata stem and leaf | [21] |
7 | 10-Hydroxyliriodenine | M. CF. banacea root | [4] |
8 | Isocorydine | M. velutina stem bark | [23] |
9 | (+)- Isocorydine α-N-oxide | M. velutina stem bark | [22] |
10 | Kinabaline | M. cuneata stem and leaf | [21] |
11 | Lanuginosine | M. cuneata stem and leaf | [21] |
12 | Liriodenine | M. balansae stem; M. cuneata stem and leaf; M. mollis twig, M. sinensis leaf and branch; M. velutina stem bark | [21, 23–26, 37] |
13 | (+)-Liriotulipiferine | M. cuneata stem and leaf | [21] |
14 | 10-Methoxyliriodenine (lauterine) | M. CF. banacea root | [4] |
15 | 1-N-Methylcoclaurine | M. balansae stem | [26] |
16 | N-Methylcorydaldine | M. cuneata stem and leaf | [21] |
17 | N-Methyllindcarpine | M. cuneata stem and leaf | [21] |
18 | Miliusacunine A | M. cuneata leaf | [7] |
19 | Miliusacunine B | M. cuneata leaf | [7] |
20 | Miliusacunine C | M. cuneata leaf | [7] |
21 | Miliusacunine D | M. cuneata leaf | [7] |
22 | Miliusacunine E | M. cuneata leaf | [7] |
23 | Miliusathorine A | M. thorelii stem and root | [8] |
24 | Miliusathorine B | M. thorelii stem and root | [8] |
25 | Norcorydine | M. velutina stem bark | [23] |
26 | (-)-Nordicentrine | M. cuneata stem and leaf | [21] |
27 | Norisocorytuberine | M. cuneata stem and leaf | [21] |
28 | (−)-Norushinsunine | M. mollis twig; M. thorelii stem and root | [8, 24] |
29 | Pseudocolumbamine | M. cuneata stem and leaf | [21] |
30 | Reticuline | M. velutina stem bark | [23] |
31 | Salutarine | M. cuneata stem and leaf | [21] |
32 | Wilsonirine | M. cuneata stem and leaf | [21] |
Homogentisic acid derivatives |
33 | Methyl 2-(1′β-geranyl-5′β-hydroxy-2′-oxocyclohex-3′-enyl) acetate | M. umpangensis leaf; M. velutina fruit | [32, 33] |
34 | 2-(1′β-Geranyl-5′β-hydroxy-2′-oxocyclohex-3′-enyl) acetic acid | M. velutina fruit and flower | [32] |
35 | Miliusanal | M. velutina fruit | [32] |
36 | Miliusanone A | M. velutina fruit | [32] |
37 | Miliusanone B | M. velutina fruit | [32] |
38 | Miliusanone C | M. velutina flower | [32] |
39 | Miliusanone D | M. velutina flower | [32] |
40 | (+)-Miliusate | M. balansae leaf, branch and stem; M. sinensis leaf, twig and flower; M. umpangensis leaf | [13, 14, 31, 33, 34] |
41 | (+)-Miliusane I | M. balansae stem; M. sinensis leaf, twig and flower; M. umpangensis leaf | [13, 14, 33] |
42 | (+)-Miliusane II | M. balansae stem; M. sinensis leaf, twig and flower | [13, 14] |
43 | (+)-Miliusane III | M. sinensis leaf, twig and flower | [14] |
44 | (+)-Miliusane IV | M. sinensis leaf, twig and flower | [14] |
45 | (+)-Miliusane V | M. sinensis leaf, twig and flower | [14] |
46 | (+)-Miliusane VI | M. sinensis leaf, twig and flower | [14] |
47 | (+)-Miliusane VII | M. sinensis leaf, twig and flower | [14] |
48 | (+)-Miliusane VIII | M. sinensis leaf, twig and flower | [14] |
49 | (+)-Miliusane IX | M. balansae stem; M. sinensis leaf, twig and flower | [13, 14] |
50 | (+)-Miliusane X | M. sinensis leaf, twig and flower | [14] |
51 | (+)-Miliusane XI | M. sinensis leaf, twig and flower | [14] |
52 | (+)-Miliusane XII | M. sinensis leaf, twig and flower | [14] |
53 | (+)-Miliusane XIII | M. sinensis leaf, twig and flower | [14] |
54 | (+)-Miliusane XIV | M. balansae stem; M. Sinensis leaf, twig and flower | [13, 14] |
55 | (+)-Miliusane XV | M. balansae stem; M. Sinensis leaf, twig and flower | [13, 14] |
56 | (+)-Miliusane XVI | M. sinensis leaf, twig and flower | [14] |
57 | (+)-Miliusane XVII | M. balansae stem; M. sinensis leaf, twig and flower | [13, 14] |
58 | (+)-Miliusane XVIII | M. sinensis leaf, twig and flower | [14] |
59 | (+)-Miliusane XIX | M. sinensis leaf, twig and flower | [14] |
60 | (+)-Miliusane XX | M. sinensis leaf, twig and flower | [14] |
61 | Miliusane XXI | M. balansae stem | [13] |
62 | Miliusane XXII | M. balansae stem | [13] |
63 | Miliusane XXIII | M. balansae stem | [13] |
64 | Miliusane XXIV | M. balansae stem | [13] |
65 | Miliusane XXV | M. balansae stem | [13] |
66 | Miliusane XXVI | M. balansae stem | [13] |
67 | Miliusane XXVII | M. balansae stem | [13] |
68 | Miliusane XXVIII | M. balansae stem | [13] |
69 | Miliusane XXIX | M. balansae stem | [13] |
70 | Miliusane XXX | M. balansae stem | [13] |
71 | Miliusane XXXI | M. balansae stem | [13] |
72 | (+)-Miliusol | M. balansae leaf, stem and branch; M. cuneata leaf, M. sinensis leaf, twig and flower; M. umpangensis leaf | [7, 13, 14, 24, 30] |
73 | Miliusolide | M. balansae leaf and branch | [30] |
Flavonoids |
Flavones |
74 | Artemetin | M. thorelii leaf | [8] |
75 | Ayanin (5,3′-dihydroxy-3,7,4′-trimethoxyflavone) | M. smithiae leaf and twig; M. umpangensis leaf | [33, 36] |
76 | Chrysosplenol B (chrysoplenetin) | M. balansae leaf and branch; M. cuneata twig | [7, 35] |
77 | Chrysosplenol C | M. balansae leaf and branch | [11, 30, 35] |
78 | Chrysosplenol D | M. umpangensis leaf | [33] |
79 | 3,5-Dihydroxy-7,3′,4′-trimethoxyflavone | M. sinensis leaf and branch | [25, 37] |
80 | 6,4′-Dihydroxy-3,5,7-trimethoxyflavone | M. thorelii stem and root | [8] |
81 | Dimethylmikanin | M. thorelii stem and root | [8] |
82 | 3,5,6,7,3′,4′-Hexamethoxyflavone | M. thorelii leaf | [8] |
83 | 5-Hydroxy-3,7-dimethoxy-3′,4′-methylenedioxyflavone | M. cuneata leaf and twig; M. thorelii stem, root and leaf | [7, 8] |
84 | 5-Hydroxy-3,7,4′-trimethoxyflavone | M. smithiae leaf and twig | [36] |
85 | 5-Hydroxy-3,6,7,4′-tetramethoxyflavone | M. thorelii stem and root | [8] |
86 | 4′-Hydroxy-3,5,6,7-tetramethoxyflavone | M. thorelii stem and root | [8] |
87 | 4′-Hydroxy-3,5,7,3′-tetramethoxyflavone | M. cuneata leaf | [7] |
88 | Isokanugin | M. thorelii leaf | [8] |
89 | 3-O-Methylkaempferol | M. thorelii stem and root | [8] |
90 | Melisimplexin | M. thorelii stem, root and leaf | [8] |
91 | Melisimplin | M. thorelii leaf | [8] |
92 | Miliufavol | M. balansae leaf and branch | [35] |
93 | Miliusathorone | M. thorelii stem and root | [8] |
94 | Ombuine | M. balansae leaf and branch; M. umpangensis leaf | [33, 35] |
95 | Pachypodol | M. balansae leaf and branch; M. cuneata leaf and twig; M. thorelii leaf | [7, 8, 35] |
96 | 3,5,7,3′,4′-Pentamethoxyflavone | M. thorelii stem, root and leaf | [8] |
97 | Quercetagetin-3,5,7-trimethyl ether | M. thorelii stem and root | [8] |
98 | Quercetagetin-3,5,7,3′-tetramethyl ether | M. thorelii stem and root | [8] |
99 | Quercetin-3-O-methyl ether | M. thorelii stem and root | [8] |
100 | Quercetin-3,7-dimethyl ether | M. thorelii stem and root; M. umpangensis leaf | [8, 33] |
101 | Quercetin-3,5,3′-trimethyl ether | M. thorelii stem and root | [8] |
102 | Retusin | M. thorelii stem and root | [8] |
103 | Rhamnetin | M. velutina leaf | [38] |
104 | Rutin | M. balansae leaf; M. umpangensis leaf | [11, 33] |
105 | 7,3′,4′-Trimethylquercetin | M. umpangensis leaf | [33] |
Chalcones |
106 | 2′,6′-Dihydroxy-4′-Methoxydihydrochalcone | M. balansae leaf and branch | [31] |
107 | 4′,6′-Dihydroxy-2′,3′,4-trimethoxydihydrochalcone | M. sinensis leaf and branch | [37] |
108 | Dihydropashanone | M. balansae leaf and branch; M. sinensis leaf and branch | [25, 31, 37] |
109 | Pashanone | M. sinensis leaf and branch | [6, 25, 37] |
Flavanones |
110 | 5-Hydroxy-6,7-dimethoxyflavanone (onysilin) | M. balansae leaf and branch; M. sinensis leaf and branch | [6, 25, 31, 37] |
111 | 5-Hydroxy-7,8-dimethoxyflavanone | M. balansae leaf and branch; M. sinensis leaf and branch | [25, 31, 37] |
112 | 5-Hydroxy-7-methoxyflavanone (pinostrobin) | M. balansae leaf and branch; M. sinensis leaf and branch | [25, 31, 37] |
113 | 5-Hydroxy-7,4′-methoxyflavanone | M. balansae leaf and branch; M. sinensis leaf and branch | [25, 31, 37] |
114 | 7-O-Methyleriodictyol | M. velutina leaf | [38] |
115 | Sakuranetin | M. velutina leaf | [38] |
Flavan |
116 | (−)-Epicatechin | M. balansae leaf; M. fragrans leaf and stem; M. mollis leaf | [9, 11, 24] |
Lignans and neolignans |
Lignans |
117 | (+)-3-Hydroxyveraguensin | M. fragrans stem | [9] |
118 | (7S,8S,7′R,8′S)-3,4,5,3′,4′-Pentamethoxy-7,7′-epoxylignan | M. fragrans stem | [9] |
119 | (+)-Syringaresinol | M. cuneata leaf | [7] |
120 | Veraguensin | M. fragrans stem | [9] |
Neolignans |
121 | 2-(4-Allyl-2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)propane | M. mollis leaf | [9] |
122 | Conocarpan | M. mollis twig | [24] |
123 | Decurrenal | M. mollis leaf | [10] |
124 | (+)-3-O-Demethyleusiderin C [(7S,8R)-Δ-3-hydroxy-4,5,5′-trimethoxy-7.O.3′,8.O.4′-neolignan] | M. fragrans leaf | [9] |
125 | (+)-4-O-Demethyleusiderin C [(7S,8R)-Δ-4-hydroxy-3,5,5′-trimethoxy-7.O.3′,8.O.4′-neolignan] | M. fragrans leaf and stem | [9] |
126 | (2R,3R)-2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-methyl-5-(E)-propenylbenzofuran | M. mollis twig | [24] |
127 | (2S,3S)-2,3-Dihydro-2-(4-methoxyphenyl)-3-methyl-5-[1(E)-propenyl] benzofuran | M. mollis twig | [24] |
128 | (+)-Eusiderin A | M. fragrans stem | [9] |
129 | Eusiderin C | M. fragrans stem | [9] |
130 | Eusiderin D | M. fragrans stem and leaf | [9] |
131 | Licarin A | M. fragrans leaf | [9] |
132 | (7S,8S)-threo-Δ-4-Methoxyneolignan | M. mollis twig | [24] |
133 | 7-Methoxymiliumollin [(2R,3R)-5-allyl-2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-3-methylbenzofuran] | M. mollis leaf | [10] |
134 | 3′-Methoxymiliumollin [(2R,3R)-5-allyl-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-methylbenzofuran] | M. mollis leaf | [10] |
135 | (−)-4-O-Methylmiliusfragrin [(7R,8R)-Δ-3,4,5′-trimethoxy-7.O.3′,8.O.4′-neolignan] | M. fragrans stem | [9] |
136 | 4′-O-Methylmiliumollin [(2S,3S)-5-allyl-2,3-dihydro-2-(4-methoxyphenyl)-3-methylbenzofuran)] | M. mollis leaf | [10] |
137 | (−)-Miliufragranol A [(Δ-9′-hydroxy-3,4,3′,5′-tetramethoxy-8.O.4′-neolignan] | M. fragrans stem | [9] |
138 | (−)-Miliufragranol B [(Δ-4-hydroxy-3,5′-dimethoxy-8.O.4′-neolignan] | M. fragrans leaf | [9] |
139 | (−)-Miliusfragrin [(7R,8R)-Δ-4-hydroxy-3,5′-dimethoxy-7.O.3′,8.O.4′-neolignan] | M. fragrans leaf and stem | [9] |
140 | Miliumollin [(2R,3R)-5-allyl-2,3-dihydro-2-(4-hydroxyphenyl)-3-methylbenzofuran)] | M. mollis leaf | [10] |
141 | Miliumollinone [(2R,3R)-2,3-dihydro-2-(4-hydroxyphenyl)-3-methyl-5-(2-oxopropyl)-benzofuran] | M. mollis leaf | [10] |
142 | Miliusanollin [(7R,8R)-threo-Δ-7-acetoxy-4-methoxy-8-O-4′-neolignan] | M. mollis leaf | [10] |
143 | (7S,8R)-7-hydroxy-3,4,3′-trimethoxy-Δ-8.O.4′-neolignan | M. fragrans leaf | [9] |
144 | Virolongin B | M. fragrans stem | [9] |
Acetogenins |
145 | Acetogenins A | M. velutina stem bark | [5] |
146 | Acetogenins B | M. velutina stem bark | [5] |
147 | Cananginone A | M. velutina stem bark and flower | [32, 40] |
148 | Cananginone B | M. velutina stem bark | [40] |
149 | Cananginone C | M. velutina stem bark | [40] |
150 | Cananginone D | M. velutina stem bark | [40] |
151 | Cananginone E | M. velutina stem bark | [40] |
152 | Cananginone F | M. velutina stem bark | [40] |
153 | Cananginone G | M. velutina stem bark | [40] |
154 | Cananginone H | M. velutina stem bark, leaf and flower | [32, 38, 40] |
155 | Cananginone I | M. velutina stem bark | [40] |
156 | Miliusolide | M. velutina stem bark | [39] |
157 | Miliusolide dihydro derivative | M. velutina stem bark | [39] |
158 | Goniothalamusin | M. velutina stem bark | [5] |
Lactones |
159 | Curcolide | M. balansae leaf | [11] |
160 | Serralactone | M. balansae leaf | [11] |
161 | Velutinone A | M. velutina leaf | [38] |
162 | Velutinone B | M. velutina leaf | [38] |
163 | Velutinone C | M. velutina leaf | [38] |
164 | Velutinone D | M. velutina leaf | [38] |
165 | Velutinone E | M. velutina leaf | [38] |
166 | Velutinone F | M. velutina leaf | [38] |
167 | Velutinone G | M. velutina leaf | [38] |
168 | Velutinone H | M. velutina leaf | [38] |
Styryls |
Mono-styryl derivatives |
169 | 3,4-Dimethoxy-6-styryl-pyran-2-one | M. balansae leaf and branch | [31] |
170 | (2E,5E)-2-Methoxy-4-oxo-6-phenyl-hexa-2,5-dienoic acid methyl ester | M. balansae leaf and branch | [31] |
171 | Yangonin | M. velutina leaf, fruit and flower | [32, 38] |
Bi-styryl derivatives |
172 | Miliubisstyryl A | M. balansae leaf and branch | [41] |
173 | Miliubisstyryl B | M. balansae leaf and branch | [41] |
174 | Velutinindimer A | M. velutina leaf, fruit and flower | [32, 38] |
175 | Velutinindimer B | M. velutina leaf, fruit and flower | [32, 38] |
176 | Velutinindimer C | M. velutina leaf | [38] |
Terpenoids |
Norsesquiterpenoids type megastigmanes and megastigmane glycosides |
177 | Alangionoside B | M. balansae stem | [42] |
178 | Ampelopsisionoside | M. balansae leaf | [11] |
179 | Milbaside A | M. balansae leaf | [11] |
180 | Milbaside B | M. balansae leaf | [11] |
181 | Milbaside C | M. balansae leaf | [11] |
182 | Miliusoside C | M. balansae stem | [42] |
183 | Myrsinionoside A | M. balansae leaf | [11] |
184 | Myrsinionoside D | M. balansae leaf | [11] |
Triterpenoid |
185 | 24-Methylencycloartane-3β,21-diol | M. sinensis leaf and branch | [25, 37] |
Mono-phenols and mono-phenol glycosides |
186 | bis(2-Hydroxyphenyl)methyl ether | M. balansae leaf and branch | [30] |
187 | Cuchiloside | M. balansae stem | [42] |
188 | 4-Hydroxybenzonitrile | M. velutina fruit | [32] |
189 | 4-Hydroxybenzaldehyde | M. velutina fruit | [32] |
190 | Icariside D2 | M. mollis twig | [24] |
191 | Isovanillin | M. velutina fruit | [32] |
192 | 1-(3-Methylbutyryl)phloroglucinol-glucopyranoside | M. balansae leaf | [11] |
193 | Miliusoside A | M. balansae stem | [42] |
194 | Miliusoside B | M. balansae stem | [42] |
195 | Osmanthuside H | M. balansae stem | [42] |
196 | 1-(α-L-Rhamnosyl-(1→6)-β-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene | M. balansae stem | [42] |
197 | 3,4,5-Trimethoxyphenol-β-D-glucopyranoside | M. balansae stem | [42] |
198 | Tyrosol-1-O-β-xylopyranosyl-(1→6)-O-β-glucopyranoside | M. mollis twig | [24] |
Amines and amides |
199 | Adenine riboside | M. balansae stem | [26] |
200 | Allantoin | M. balansae stem | [26] |
201 | N-trans-Caffeoyltyramine | M. cuneata twig; M. thorelii stem and root | [7, 8] |
202 | N-trans-Coumaroyltyramine | M. cuneata twig | [7] |
203 | N-trans-Feruloyltyramine | M. cuneata twig; M. thorelii stem and root | [7, 8] |
204 | Uridine | M. balansae stem | [26] |
Alcohols |
205 | β-D-Glucopyranoside (Z)-3-hexenol | M. balansae leaf | [11] |
206 | erythro-Guaiacylglycerol | M. balansae leaf | [11] |
207 | threo-Guaiacylglycerol | M. balansae leaf | [11] |
208 | (L)-Guaiacyl glycerol 2′-O-β-D-glucopyranoside | M. balansae leaf | [11] |
209 | erythro-1-C-Syringylglycerol | M. balansae leaf | [11] |
210 | threo-1-C-Syringylglycerol | M. balansae leaf | [11] |
Furfurals |
211 | 5-Acetyloxymethylfurfural | M. velutina fruit | [32] |
212 | 5-Hydroxymethylfurfural | M. velutina fruit | [32] |
213 | 5-Methoxyfurfural | M. velutina fruit | [32] |
Others |
214 | D-Glucose | M. balansae stem | [26] |
215 | Octacosanoic acid | M. balansae leaf and branch | [41] |
216 | β-Sitosterol | M. balansae stem; M. velutina fruit | [26, 32] |
217 | β-Sitosterol glucoside | M. balansae stem; M. sinensis leaf and branch | [25, 26] |
218 | Sodium benzoate | M. balansae leaf and branch | [30] |
219 | Stigmasterol | M. sinensis leaf and branch; M. velutina fruit and flower | [25, 32] |
220 | Sucrose | M. balansae stem | [26] |
|