Genus Miliusa: A Review of Phytochemistry and Pharmacology

Table 1

Chemical constituents from Miliusa species.

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]

coincidence name