胡颓子属植物化学成分及药理活性研究进展

doi:10.3969/j.issn.0253-2417.2021.04.017

Abstract

Abstract:

Most plants of Elaeagnus genus were widely used as folk medicines, and their fruits are edible. This review summarized the research progress of the chemical constituents of Elaeagnus plants and their biological activities. The main chemical constituents isolated from Elaeagnus plants, such as flavonoids, triterpenes, sterols, alkaloids, lignans and other compounds, were described in detail. The various activities of the compounds or the extracts such as antioxidant, antibacterial, pesticidal activities, etc, were introduced.Finally, the development potential of Elaeagnus plants in the fields of functional food, health care products and pharmaceuticals were summarized. Further research on their chemical constituents and bioactivities were proposed. And this review could provide reference for the rational use of Elaeagnus plants.

Key words: Elaeagnus, chemical constituents, biological activities

CLC Number:

TQ35

Hongdan ZHUANG, Fengqiu LI, Ruilong LUO, Liqin WANG. Research Progress of Chemical Constituents and Pharmacological Activity of Elaeagnus Plants[J]. Chemistry and Industry of Forest Products, 2021, 41(4): 135-146.

Figures/Tables 6

Fig.1

Table 1

Structures of flavones from Elaeagnus plants"

编号 No.	化合物compound	取代基substituent
编号 No.	化合物compound	R₁	R₂	R₃	R₄
1	5-羟基-7, 4′ -二甲氧基黄酮5-hydroxy-7, 4′-dimethoxyflavone	OCH₃	H	OCH₃	H
2	5-羟基-7, 3′, 4′-三甲氧基黄酮5-hydroxy-7, 3′, 4′-trimethoxyflavone	OCH₃	H	OCH₃	OCH₃
3	5, 3′-二羟基-7, 4′-二甲氧基黄酮5, 3′-dihydroxy-7, 4′-dimethoxyflavone	OCH₃	H	OCH₃	OH
4	5, 4′-二羟基-7, 3′-二甲氧基黄酮5, 4′-dihydroxy-7, 3′-dimethoxyflavone	OCH₃	H	OH	OCH₃
5	异鼠李素isorhamnetin	OH	OH	OH	OCH₃
6	槲皮素quercetin	OH	OH	OH	OH
7	山奈酚kaempferol	OH	OH	OH	H
8	3, 3′-二甲氧基槲皮素3, 3′-dimethoxyquercetin	OH	OCH₃	OH	OCH₃
9	3-甲氧基山奈酚3-methoxykaempferol	OH	OCH₃	OH	H
10	白杨素7-O-β-D-吡喃葡萄糖苷7-O-β-D-glucopyranosylchrysin	OGlc	H	H	H
11	异鼠李素3-O-α-L-鼠李糖基-7-O-β-D-吡喃葡萄糖苷 isorhamnetin 3-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside	OGlc	ORha	OH	OCH₃
12	山柰酚3-O-β-D-吡喃葡萄糖苷kaempferol 3-O-β-D-glucopyranoside	OH	OGlc	OH	H
13	山奈酚3-O-β-D-(6″-O-反式-对香豆酰基)吡喃葡萄糖苷 kaempferol 3-O-β-D-(6″-O-trans-p-coumaroyl)glucopyranoside	OH	Cou	OH	H
14	槲皮素3-O-β-D-(2-O-β-D-葡萄糖基)吡喃葡萄糖苷 quercetin 3-O-β-D-(2-O-β-D-glucopyranosyl)glucopyranoside	H	CH₃	Sin
15	槲皮素3-O-β-D-[2″-β-D-(6"'-O-E-4-芥酰基)葡萄糖吡喃糖基]葡萄糖吡喃 quercetin3-O-β-D-[2″-O-β-D-(6"'-O-E-4-sinapoyl) glucopyranosyl]glucopyranoside	Rha	H	Sin
16	芦丁rutin	OH	Rha	OH	OH
17	山奈酚3-O-β-D-吡喃葡萄糖苷-(1→3)-α-L-鼠李糖苷-(1→6)-[α-L-鼠李糖苷(1→2)]-β-D-半乳糖苷-7-O-β-D-吡喃葡萄糖苷 kaempferol 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)-[α-L-rhamnopy-ranosyl(1→2)]-β-D-galactopyranoside-7-O-β-D- glucopyranoside	Glc	H	Glc	Rha
18	山奈酚3-O-α-L-鼠李糖基-(1→6)-[α-L-鼠李糖基-(1→2)]-β-D-吡喃半乳糖苷-7-O-β-D-吡喃葡萄糖苷 kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-galactopy-ranoside-7-O-β-D-glucopyranoside	Glc	H	H	Rha
19	山奈酚3-O-β-D-吡喃葡萄糖基(1→3)-α-L-鼠李糖基-(1→6)-[α-L-鼠李糖基(1→2)]-β-D-吡喃半乳糖苷 kaempferol 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl-(1→6)-[α-L-rhamnopy-ranosyl(1→2)]-β-D-galactopyranoside	H	H	Glc	Rha
20	异鼠李素3-O-β-D-吡喃葡萄糖基-(1→3)-α-L-鼠李糖基-(1→6)-β-D-半乳糖苷 isorhamnetin 3-O-β-D-glucopyranosyl-(1→3)-α-L- rhamnopyranosyl-(1→6)-β-D-galactopyranoside	H	OCH₃	Glc	H
21	山奈酚3-O-β-D-吡喃葡萄糖基-(1→3)-α-L-鼠李糖基-(1→6)-β-D-吡喃半乳糖苷kaempferol 3-O-β-D-glucopyranosyl-(1→3)-α-L- rhamnopyranosyl-(1→6)-β-D-galactopy-ranoside	H	H	Glc	H
22	山奈酚3-O-β-D-吡喃葡萄糖基-(1→3)-α-L-鼠李糖基-(1→6)-β-D-吡喃半乳糖苷-7-O-β-D-吡喃葡萄糖苷 kaempferol 3- O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside-7-O-β-D-glucopyranoside	Glc	H	Glc	H
23	异鼠李素3-O-α-L-鼠李糖基-(1"'→2″β-D-吡喃葡萄糖苷-7-O-(6″″-O-异戊酰基)-β-D-吡喃葡萄糖苷 isorhamnetin 3-O-α-L-rhamnopyranosyl-(1"'→2″)-β-D-glucopyranoside -7-O-(6″″-O-isovaleryl)-β-D-glucopyranoside	Isoval	H	Rha	H
24	异鼠李素3-O-α-L-鼠李糖基-(1"'→6″)-β-D-吡喃葡萄糖苷-7-O-(6″″-O-异戊酰基)-β-D-吡喃葡萄糖苷 isorhamnetin 3-O-α-L-rhamnopyranosyl-(1"'→6″)-β-D-glucopyranoside -7-O-(6″″-O-isovaleryl)-β-D-glucopyranoside	Isoval	H	H	Rha
25	异鼠李素3-O-β-D-吡喃葡萄糖苷-7-O-(6"'-O-异戊酰基)-β-D-吡喃葡萄糖苷 isorhamnetin 3-O-β-D-glucopyranoside-7-O-(6"'-O-iso- valeryl)-β-D-glucopyranoside	Isoval	H	H	H
26	异鼠李素3-O-α-L-鼠李糖基-(1"'→6″)-β-D-吡喃葡萄糖苷-7-O-(2″″- O-异戊酰基)-β-D-吡喃葡萄糖苷 isorhamnetin 3-O-α-L-rhamnopyranosyl-(1"'→6″)-β-D-glucopyranoside- 7-O-(2″″-O-isovaleryl)-β-D-glucopyranoside	H	Isoval	H	Rha
27	异鼠李素3-O-β-D-吡喃葡萄糖苷-7-O-(2"'-O-异戊酰基)-β-D-吡喃葡萄糖苷 isorhamnetin 3-O-β-D-glucopyranoside-7-O-(2"'- O-isovaleryl)- β-D-glucopyranoside	H	Isoval	H	H
28	异鼠李素3-O-[(6"'-O-异戊酰基)-β-D-吡喃葡萄糖基-(1"'→2″)]-β-D-吡喃葡萄糖苷-7-O-α-L-鼠李糖苷 isorhamnetin 3-O-[(6"'-O-isovaleryl)-β-D-glucopyranosyl-(1"'→2″)]-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside	H	H
29	异鼠李素3-O-β-D-吡喃葡萄糖苷-7-O-(3"'-O-异戊酰基)-α-L-鼠李糖苷isorhamnetin 3-O-β-D-glucopyranoside -7-O-(3"'-O-isovaleryl)-α-L-rhamnopyranoside	Isoval	H	H
30	异鼠李素3-O-β-D-吡喃葡萄糖苷-7-O-(2"'-O-异戊酰基)-α-L-鼠李糖苷 isorhamnetin 3-O-β-D-glucopyranoside-7-O-(2"'-O-isovaleryl)-α-L-rhamnopyranoside	H	Isoval	H
31	异鼠李素3-O-β-D-葡萄糖苷-7-O-α-L-鼠李糖苷 isorhamnetin 3-O-β-D-glucoside-7-O-α-L-rhamnoside	H	H	H
32	异鼠李素-3-O-β-D-葡萄糖苷-7-O-α-L-(3"'-异戊酰基)鼠李糖苷 isorhamnetin 3-O-β-D-glucoside-7-O-α-L-(3"'-isovaleryl)rhamnoside	Isoval	H	H
33	elaeagnoside A	H	H	Cou
34	elaeagnoside B	H	Rha	Fer
35	elaeagnoside C	H	Rha	Sin
36	elaeagnoside D	H	Rha	Benz
37	elaeagnoside E	H	Isoval	Rha
38	elaeagnoside F	Glc	H	Fer
39	elaeagnoside G	Gal	Rha	H
40	山奈酚3-O-β-D-(4″-O-E-4-香豆酰基)葡萄糖吡喃苷 kaempferol 3-O-β-D-(4″-O-E-4-coumaroyl)glucopyranoside	Cou	H	H	H
41	山奈酚3-O-β-D-(6″-O-E-4-香豆酰基)葡萄糖吡喃苷 kaempferol 3-O-β-D-(6″-O-E-4-coumaroyl)glucopyranoside	H	Cou	H	H
42	山奈酚3-O-β-D-吡喃木糖(1→2)-β-D-吡喃半乳糖苷-7-O-α-L-鼠李糖苷 kaempferol 3-O-β-D-xylopyranosyl(1→2)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside	Rha	Xyl	H	H
43	山奈酚3-O-β-D-半乳糖苷-7-O-α-L-鼠李糖苷 kaempferol 3-O-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside	Rha	H	H	H
44	山奈酚3-O-α-L-鼠李糖苷(1→6)-β-D-半乳糖苷-7-O-α-L-鼠李糖苷 kaempferol 3-O-α-L-rhamnopyranosyl(1→6)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside	Rha	H	Rha	H
45	山奈酚3-O-β-D-木吡喃糖基(1→2)-β-D-半乳糖吡喃糖苷 kaempferol 3-O-β-D-xylopyranosyl(1→2)-β-D-galactopyranoside	H	Xyl	H	H
46	山柰酚3-O-芸香苷kaempferol 3-O-rutinoside	OH	Rha	OH	H
47	山奈酚3-O-β-D-吡喃葡萄糖(1→2)-β-D-吡喃半乳糖苷-7-O-α-L-鼠李糖苷 kaempferol 3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside	Rha	Glc	H	H
48	山奈酚3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃半乳糖苷 kaempferol 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside	H	Glc	H	H
49	异鼠李素3-O-α-L-木吡喃糖基-(1→2)-β-D-葡萄糖苷 isorhamnetin 3-O-α-L-xylopyranosyl-(1→2)-β-D-glucopyranoside	H	H	Xyl	OCH₃
50	槲皮素3-O-α-L-木吡喃糖基-(1→2)-β-D-半乳糖吡喃糖苷 quercetin 3-O-α-L-xylopyranosyl-(1→2)-β-D-galactopyranoside	H	Xyl	H	OH
51	槲皮素3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-半乳糖苷-7-O-α-L-鼠李糖苷 quercetin 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside	Rha	Glc	H	OH
52	angustifolinoid B
53	angustifolinoid A
54	牡荆黄素vitexin
55	柚皮素naringenin	H	H
56	柚皮素7-O-β-D-吡喃葡萄糖苷naringenin 7-O-β-D-glucopyranoside	Glc	H
57	2-羟基桂皮素7-O-β-D-吡喃葡萄糖苷2-hydroxynaringenin 7-O-β-D-glucopyranoside	Glc	OH
58	查耳酮苷trilobatin	OH
59	3-苯基-1-(2′，6′-二羟基苯基-4′-O-β-D-吡喃葡萄糖基)-1-丙酮 3-phenyl-1-(2′, 6′-dihydroxy-phenyl-4′-O-β-D-glucopyranosyl)-1-propanone	H

Table 1

Table 2

Structures of terpenes from Elaeagnus plants"

编号 No.	化合物compound	取代基substituent
编号 No.	化合物compound	R₁	R₂	R₃	R₄
60	2α-羟基乌苏酸2α-hydroxy-ursolic acid	H	OH	H
61	2α , 23-二羟基乌苏酸2α , 23-dihydroxy-ursolic acid	H	OH	OH
62	马斯里酸maslinic acid	H	OH
63	乌苏酸ursolic acid	H	H	H
64	齐墩果酸oleanolic acid	H	H
65	反式-3-O-对羟基肉桂酰基齐墩果酸 trans-3-O-p-hydroxycinnamoyloleanolic acid	反式对羟基肉桂酰基 trans-p-hydroxycinnamoyl	H	H
66	反式-3-O-对羟基肉桂酰基乌苏酸 trans-3-O-p-hydroxycinnamoylursolic acid	反式对羟基肉桂酰基 trans-p-hydroxycinnamoyl	H
67	顺式-3-O-对羟基肉桂酰基齐墩果酸 cis-3-O-p-hydroxycinnamoyloleanolic acid	顺式对羟基肉桂酰基 cis-p-hydroxycinnamoyl	H	H
68	顺式-3-O-对羟基肉桂酰基乌苏酸 cis-3-O-p-hydroxycinnamoylursolic acid	顺式对羟基肉桂酰基 cis-p-hydroxycinnamoyl	H
69	28-O-β-D-吡喃葡萄糖基3β-O-β-D-吡喃葡萄糖基-(1→3)-β-D-吡喃葡萄糖基-(1→2)-[α-L-鼠李糖基]-(1→3)-α-L-阿拉伯吡喃葡萄糖基-19-氧代齐墩果酸酯 28-O-β-D-glucopyranosyl 3β-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl]-(1→3)-α-L-arabinopyranosyl-19-oxooleanolate	Rha	Glc	H	Glc
70	28-O-α-L-鼠李糖基3β-O-β-D-吡喃葡萄糖基-(1→3)-β-D-吡喃葡萄糖基-(1→2)-[α-L-鼠李糖基]-(1→3)-α-L-阿拉伯吡喃葡萄糖基-19-氧代齐墩果酸酯 28-O-α-L-rhamnopyranosyl 3β-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl]-(1→3)-α-L-arabinopyranosyl-19-oxooleanolate	Rha	Glc	H	Rha
71	28-O-β-D-吡喃葡萄糖基3β-O-[β-D-吡喃葡萄糖基-(1→6)]-[β-D-吡喃葡萄糖基-(1→3)][α-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖基-(1→3)-α-L-阿拉伯吡喃糖基-19-氧代齐墩果酸酯 28-O-β-D-glucopyranosyl 3β-O-[β-D-glucopyranosyl-(1→6)]-[β-D-glucopyranosyl-(1→3)][α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl-19-oxooleanolate	Rha	Glc	Glc	Glc
72	28-O-β-D-吡喃葡萄糖基3-O-[β-D-吡喃葡萄糖基-(1→6)]-[β-D-吡喃葡萄糖基)-(1→3)]-[α-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖基-(1→3)-α-L-吡喃阿拉伯糖基-19-氧代齐墩果烯 28-O-β-D-glucopyranosyl 3-O-[β-D-glucopyranosyl-(1→6)]-[β-D-glucopyranosyl)-(1→3)]-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl-19-oxoolean-13-en-28-oate	Rha	Glc	Glc	Glc
73	乌苏醛ursaldehyde
74	羽扇豆醇lupeol
99	(6S , 9S )-6, 9-dihydroxymegastiman-4-en-3-one-9-O-β-D-glucopyranoside
100	(6S , 9S )-6, 9-dihydroxymegastiman-4-en-3-one-9-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside
101	布卢门醇C 9-O-β-D-吡喃葡萄糖苷blumenol C 9-O-β-D-glucopyranoside
102	布卢门醇C 9-O-β-D-呋喃芹糖-(1→6)-吡喃葡萄糖苷 blumenol C 9-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside
103	吐叶醇vomifoliol
104	长寿花苷roseoside
105	10-O-β-D-glucopyranosylamygdalactone

Table 2

Fig.2

Fig.3

Fig.4

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