野鸦椿属植物的化学成分及药理作用研究进展

doi:10.3969/j.issn.0253-2417.2023.02.019

Abstract

Abstract:

The main chemical constituents of Euscaphis plants are triterpenoids, phenolic acids, flavonoids, lignans, sesquiterpenoids, etc. Modern research shown that the extracts and monomeric compounds of the Euscaphis plants had anti-inflammatory, anti-bacterial, anti-tumour, anti-hepatic fibrosis and other pharmacological effects. At present, species delimitation of Euscaphis was changed and it was not very clear whether there were differences in chemical composition between the different varieties. Through the systematic search and summary of the chemical composition and pharmacological effects of Euscaphis plants, and we deeply elaborated whether differences in chemical composition was existed between different species and possible differential components, in order to provide a reference for the classification, development and use of Euscaphis plants.

Key words: Euscaphis, chemical constituents, pharmacological action

CLC Number:

TQ35
TQ91

Liangjie TANG, Wei LUO, Hulan CHEN. Research Progress of Chemical Constituents and Pharmacological Effects of Euscaphis Plants[J]. Chemistry and Industry of Forest Products, 2023, 43(2): 153-170.

Figures/Tables 15

Fig.1

Table 1

The 43 triterpenoids in Euscaphis"

序号 No.	化合物 compound	CAS编号 CAS number	取代基substituent						品种¹⁾ species	文献 ref.
序号 No.	化合物 compound	CAS编号 CAS number	R₁	R₂	R₃	R₄	R₅	R₆	品种¹⁾ species	文献 ref.
1	野鸦椿酸A euscaphic acid A	1252662-04-6	H	β-OH	H	α-OH			a	[15]
2	野鸦椿酸B euscaphic acid B	1252662-06-8	H	β-OH	OH	α-OH			a	[15]
3	野鸦椿酸C euscaphic acid C	1252662-08-0	α-OH	α-OH	H	α-OH			a	[15]
4	野鸦椿酸D euscaphic acid D	1252662-10-4	α-OH	β-OH	H	α-OH			a	[15]
5	野鸦椿酸E euscaphic acid E	1252662-11-5	α-OH	β-OH	H	H			a	[15]
6	野鸦椿酸F euscaphic acid F	1252662-12-6							a	[15]
7	(12R, 13S)-3-甲氧基-12, 13-环丙烷-蒲公英赛烯-2, 14-二烯-1-酮-28-羧酸 (12R, 13S)-3-methoxy-12, 13-cyclo-taraxerene-2, 14-diene-1-one-28-oic acid	2189705-20-0							a	[16]
8	齐墩果酸oleanolic acid	508-02-1	H	H	β-OH	CH₃	H	COOH	a-c	[17-21]
9	泰国树脂酸siaresinolic acid	511-77-3	H	OH	β-OH	CH₃	H	COOH	b	[21]
10	1α, 3β-二羟基-12-齐墩果烯-28-酸 1α, 3β-dihydroxy-12-oleanen-28-oic acid	439688-90-1	OH	H	β-OH	CH₃	H	COOH	a	[22]
11	马斯里酸maslinic acid	4373-41-5	H	α-OH	β-OH	CH₃	H	COOH	a, c	[22-24]
12	阿江榄仁酸arjunic acid	31298-06-3	H	α-OH	β-OH	CH₃	OH	COOH	a	[22]
13	常春藤皂苷元hederagenin	465-99-6	H	H	β-OH	CH₂OH	H	COOH	a	[22]
14	2α, 3α, 23-三羟基齐墩果-12-烯-28酸 2α, 3α, 23-trihydroxyolean-12-en-28-oic acid	102519-34-6	H	α-OH	α-OH	CH₂OH	H	COOH	a	[22]
15	ilexosapogenin A	148031-70-3	H	H	β-OH	CH₂OH	OH	COOH	a	[22]
16	β-香树脂醇β-amyrin	559-70-6	H	H	OH	CH₃	H	H	c	[20]
17	野鸦椿酸G euscaphic acid G	1453471-17-4		CH₂OH					a	[22]
18	野鸦椿酸H euscaphic acid H	1453471-16-3		CH₃					a	[22]
19	野鸦椿酸I euscaphic acid I	1453471-13-0	CH₃	H	CH₂OH				a	[22]
20	木鳖子酸momordic acid	14356-51-5	CH₃	H	CH₃				a, c	[22, 24]
21	3β, 23-二羟基-1-羰基-齐墩果-12-烯-28-酸 3β, 23-dihydroxy-1-oxo-olean-12-en-28-oic aicd	618390-67-3	CH₂OH	H	CH₃				a	[22]
22	1-氧泰国树脂酸1-oxosiaresinolic acid	1772612-72-2	CH₃	α-OH	CH₃				c-d	[20, 25]
23	表赤杨醇5-glutinen-3-ol	545-24-4							a	[26]
24	熊果酸ursolic acid	77-52-1	H	OH	CH₃	CH₃	H	COOH	b-c	[27-28]
25	2α-羟基熊果酸2α-hydroxyursolic acid	4547-24-4	α-OH	OH	CH₃	CH₃	H	COOH	a	[15]
26	3β, 23-二羟基熊果-12-烯-28-酸 3β, 23-dihydroxy-urs-12-en-28-oic acid	94414-19-4	H	OH	CH₃	CH₂OH	H	COOH	a	[19]
27	19α, 23-二羟基熊果酸-23-甲酯 19α, 23-dihydroxyursolic acid-23-methyl ester	20512-40-7	H	OH	CH₃	CH₂OH	α-OH	COOCH₃	a	[26]
28	野鸦椿酸K euscaphic acid K	109792-66-7	α-OH	α-OH	COOCH₃	CH₃	OH	COOH	a	[22]
29	2α, 3β, 19α-三羟基熊果-12-烯-23, 28-二羧酸基酸-23-甲酯 2α, 3β, 19α-trihydroxyurs-12-ene-23, 28-dioic acid-23-methyl ester	132282-70-3	α-OH	β-OH	COOCH₃	CH₃	OH	COOH	a	[22]
30	野鸦椿酸euscaphic acid	53155-25-2	α-OH	α-OH	CH₃	CH₃	OH	COOH	a-b	[17, 28]
31	委陵菜酸tormentic acid	13850-16-3	α-OH	β-OH	CH₃	CH₃	OH	COOH	a, b, d	[15, 25, 28]
32	坡模醇酸pomolic acid	13849-91-7	H	β-OH	CH₃	CH₃	OH	COOH	a-d	[21, 25-27]
33	23-醛基坡模醇酸23-aldehydepomolic acid	1252662-13-7	H	β-OH	CHO	CH₃	OH	COOH	a	[15]
34	铁冬青酸rotundic acid	20137-37-5	H	β-OH	CH₂OH	CH₃	OH	COOH	a	[15, 19]
35	19α, 23-二羟基熊果酸rotungenic acid	121467-43-4	H	β-OH	CH₃	CH₂OH	OH	COOH	a	[15]
36	2-表委陵菜酸2-epitormentic acid	119725-19-8	β-OH	β-OH	CH₃	CH₃	OH	COOH	a, c	[15, 20]
37	2-氧代坡模酸2-oxopomolic acid	54963-52-9							c	[20]
38	坡模酮酸pomonic acid	13849-90-6							c	[24]
39	3β, 19-二羟基-24-反式-阿魏酰基-熊果-12-烯-28-酸 3β, 19-dihydroxy-24-trans- ferulyloxyurs-12-en-28-oic acid								a	[30]
40	野鸦椿酸J euscaphic acid J	1453471-14-1							a	[22]
41	野鸦椿酸L euscaphic acid L	1453471-15-2							a	[22]
42	白桦脂酸betulinic acid	472-15-1							a-c	[22-24, 28]
43	无羁萜friedelin	559-74-0							a	[26]

Table 1

Fig.2

Table 2

The 32 phenolic acids in Euscaphis"

序号 No.	化合物 compound	CAS编号 CAS number	取代基substituent¹⁾				品种 species	文献 ref.
序号 No.	化合物 compound	CAS编号 CAS number	R₁	R₂	R₃	R₄	品种 species	文献 ref.
44	鞣花酸ellagic acid	476-66-4	H	H	H	H	a, b, d	[25, 31-34]
45	3, 3′二甲氧基鞣花酸 3, 3′-di-O-methylellagic acid	2239-88-5	CH₃	H	CH₃	H	a, b, d	[31, 33-34]
46	3, 4, 3′-三甲氧基鞣花酸 3, 4, 3′-tri-O-methylellagic acid	1617-49-8	CH₃	H	CH₃	CH₃	c	[20]
47	3, 4′-二甲氧基鞣花酸-4-O-α-L-阿拉伯糖苷3, 4′-di-O-methylellagic acid-4-O-α-L-arabinofuranoside	2230070-22-9	CH₃	α-L-Araf	H	CH₃	a	[19]
48	3, 3′-二甲氧基鞣花酸-4′-O-α-L-阿拉伯糖苷3, 3′-di-O-methylellagic acid-4′-O-α-L-arabinofuranoside		CH₃	H	CH₃	α-L-Araf	b	[28]
49	3, 3′-二甲氧基鞣花酸-4′-O-α-D-阿拉伯糖苷3, 3′-di-O-methylellagic acid-4′-O-α-D-arabinofuranoside	1240040-17-8	CH₃	H	CH₃	α-D-Araf	a-b	[28, 31]
50	3, 3′, 4-三甲氧基鞣花酸-4′-O-β-D-葡萄糖苷3, 3′, 4- tri-O-methylellagic acid-4′-O-β-D-glucoside		CH₃	H	CH₃	β-D-Glu	b	[28]
51	3, 3′-二甲氧基鞣花酸-4′-O-β-D-葡萄糖苷3, 3′-di-O-methylellagic acid-4′-O-β-D-glucoside	51803-68-0	CH₃	H	CH₃	β-D-Glu	a-b	[28, 31-32]
52	3, 3′-二甲氧基鞣花酸-4′-O-β-D-木糖苷 3, 3′-di-O-methylellagic acid-4′-O-β-D-xylopyraoside	173295-10-8	CH₃	H	CH₃	β-D-Xly	a-b	[28, 31]
53	3, 3′-二甲氧基鞣花酸-4-(5″-乙酰基)-α-L-阿拉伯糖苷3, 3′-di-O-methylellagic acid-4′-(5″-acetyl)-α-L-arabf	365540-09-6	CH₃	H	CH₃	5″-acetyl-α-L-Araf	a, d	[25, 30, 33]
54	stenophyllin H1	87687-51-2	CH₃	H	CH₃	α-L-Araf	a	[35]
55	6-羟基蜂蜜曲菌素6-hydroxymellein	70901-60-9					b	[36]
56	3-羟基-1-(4-羟基-3-甲氧基苯基)丙-1-酮 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl) propan-1-one	2196-18-1					d	[25]
57	芥子醛sinapic aldehyde	4206-58-0	OCH₃	OCH₃	CHO		a, d	[25, 18]
58	咖啡酸caffeic acid	331-39-5	OH	H	COOH		b	[34]
59	阿魏酸ferulic acid	1135-24-6	OCH₃	H	COOH		b	[34]
60	松柏醛coniferaldehyde	458-36-6	H	OCH₃	CHO		d	[25]
61	松柏醇coniferol	458-35-5	H	OCH₃	CH₂OH		d	[25]
62	香豆酰基-D-苹果酸-1-甲酯 p-coumaroyl-D-malic acid-1-methyl ester	1003604-07-6					b	[35]
63	没食子酸gallic acid	149-91-7	OH	OH	COOH		a-c	[30, 37-38]
64	香草酸vanillic acid	121-34-6	H	OCH₃	COOH		a, b, d	[25, 34, 39]
65	香草醛vanillin	121-33-5	H	OCH₃	CHO		a, b, d	[25, 30, 38]
66	原儿茶酸protocatechuic acid	99-50-3	H	OH	COOH		a-b	[18, 34]
67	对羟基苯甲酸p-hydroxybenzoic acid	99-96-7	H	H	COOH		b-c	[27, 36]
68	对羟基苯甲醛p-hydroxybenzaldehyde	123-08-0	H	H	CHO		b	[40]
69	没食子酸甲酯methyl gallate	99-24-1	OH	OH	COOCH₃		a，d	[25, 39]
70	没食子酸乙酯methyl gallate	831-61-8	OH	OH	COOC₂H₅		b	[36]
71	楝叶吴萸素B evofolin B	1961305-60-1					b	[29, 40]
72	绿原酸chlorogenic acid	327-97-9					b	[34]
73	eugeniin	81571-72-4					d	[25, 33]
74	1β-O-galloyl pedunculagin	79786-00-8					a	[41]
75	euscaphinin	1160433-41-9					a	[41]

Table 2

Table 3

Fig.3

Table 4

The 27 lignans in Euscaphis"

序号No.	化合物compound	CAS编号CAS number	取代基substituent			品种species	文献ref.
序号No.	化合物compound	CAS编号CAS number	R₁	R₂	R₃	品种species	文献ref.
94	carolignan A	171758-40-0	OCH₃	H	α-OH	a	[22]
95	carolignan B	171758-41-1	OCH₃	H	β-OH	a	[22]
96	carolignan H	344944-05-4	OCH₃	OCH₃	β-OH	d	[25]
97	carolignan F	171758-43-3	H	OCH₃	β-OH	d	[25]
98	赤麻木脂素boehmenan	57296-22-7				d	[25]
99	4-氧代芝麻素4-oxysesamin	61254-17-9				b	[29]
100	(7S, 8R)-二氢脱氢二松柏醇-9-O-β-D-吡喃葡萄糖苷 (7S, 8R)-dihdrodehydrodiconiferyl alcohol-9-O-β-D-gluco-pyranoside	71144-68-8				b	[40, 46]
101	(7R, 8R)-苏式-7, 9, 9′-三羟基-3, 3′-二甲氧基-8-O-4′-新木脂素-4-O-β-D-吡喃葡萄糖苷(7R, 8R)-threo-7, 9, 9′-trihydroxy-3, 3′-dimethoxy-8-O-4′-neolignan-4-O-β-D-glucopyranoside	1009838-88-3				b	[40]
102	illiciumlignan B	2226510-55-8				b	[40, 46]
103	acernikol	623584-31-6				b	[38]
104	罗汉松脂素-4-O-β-D-葡萄糖苷 nortrachelogenin-4-O-β-D-glucopyranoside	23202-85-9	H	Glu	H	b	[38]
105	罗汉松脂素-4′-O-β-D-葡萄糖苷 nortrachelogenin-4′-O-β-D-glucopyranoside	823214-05-7	Glu	H	H	b	[38]
106	罗汉松脂素matairesinol	580-72-3	H	H	H	b	[46]
107	荛花酚wikstromol	61521-74-2	H	H	OH	b	[46]
108	苏式-1-(4-羟基-3-甲氧基苯基)-2[4-(3-羟丙基)-2-甲氧基苯氧基]-1, 3-丙二醇threo-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxy-pheno-xy]-1, 3-panediol	135820-78-9	α-OH			b	[38, 46]
109	赤式-1-(4-羟基-3-甲氧基苯基)-2[4-(3-羟丙基)-2-甲氧基苯氧基]-1, 3-丙二醇erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxy-pheno-xy]-1, 3-panediol	135820-77-8	β-OH			b	[46]
110	konilignan					b	[46]
111	蛇菰宁balaphonin	118916-57-7				d	[25]
112	异落叶松脂素isolariciresinol	548-29-8	H	H		b	[46]
113	(+)-南烛木树脂酚(+)-lyoniresinol	14464-90-5	OCH₃	OCH₃		b	[46]
114	4-ketopinoresinol	66288-89-9	H	H		b	[46]
115	丁香脂素syringaresin	487-35-4	OCH₃	OCH₃		b, d	[25, 46]
116	vladinol D	133084-47-6				b	[46]
117	(+)-(8R, 7′R, 8′R)-异落叶松脂素-9-(6-tris-对香豆酰基)-O-β-D-葡萄糖苷(+)-(8R, 7′R, 8′R)-isolari-ciresinol-9-(6-tris-p-coumaroyl)-O-β-D-glucopyranoside	1819968-31-4				b	[29]
118	(7R, 8R)-苏式-7, 9, 9′-三羟基-3, 3′-二甲氧基-8-O-4′-新木脂素7-O-α-L-鼠李糖苷(7R, 8R)-threo-7, 9, 9′-trihydroxy-3, 3′-dimethoxy -8-O-4′-lignans 7-O-α-L-rhamno-side					b	[29]
119	苏式2, 3-双(4-羟基-3-甲氧基苯基)-3-乙氧基丙-1-醇 threo-2, 3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol	468094-64-6	β-OC₂H₅			d	[25]
120	赤型2, 3-双(4-羟基-3-甲氧基苯基)-3-乙氧基丙-1-醇 erythro-2, 3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol	468094-65-7	α-OC₂H₅			d	[25]

Table 4

Fig.4

Table 5

Fig.5

Fig.6

Table 6

Table 7

Fig.7

Fig.8

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序号 No.	化合物 compound	CAS编号 CAS number	取代基(R) substituent	品种 species	文献 ref.
121	3, 7-二羟基-5-辛醇内酯3, 7-dihydroxy-5-octanolide	129987-26-4		a	[35, 39]
122	(1S, 5R, 7S)-7-甲基-2, 6-二氧杂双环[3.3.1] 壬烷- 3-酮tetraketide	276869-83-1		a-c	[20, 29, 47]
123	邻苯甲酸-双(2′-乙基庚基)酯1, 2-benzenedicerboxylic acid	70152-36-2		a, c	[23, 37]
124	5-羰基-四氢呋喃-3-甲酸乙酯 ethyl-5-oxo-tetrahydro-3-furancarboxylate	681179-32-8		a	[30]
125	佛手柑内酯bergapten	484-20-8		a	[30]
126	7-羟基-2-辛烯-5-内酯euscapholide	220862-15-7	H	a	[48-50]
127	2-辛烯-5-内酯-7-O-葡萄糖苷euscapholide glucoside	220862-16-8	β-D-Glu	a-b	[32, 48]
128	黑麦草内酯lolioide	5989-02-6		b	[40]
129	甲基-5, 7-二羟基-2(Z)-辛烯酸甲酯 methyl 5, 7-dihydroxy-2(Z)-octenoate	866025-54-9		a	[49-50]
130	甲基-5, 7-二羟基辛酸甲酯methyl-5, 7-dihydroxyoctanoate	1003604-08-7		a	[35]
131	4(R)-(4′-羟基苯甲酰)二氢呋喃-2(3H)-酮 4(R)-(4′-hydroxybenzoyl)dihydrofuran-2(3H)-one			b	[36]

序号 No.	化合物 compound	CAS编号 CAS number	取代基(R) substituent	品种 species	文献 ref.
132	(6S, 9S)-长春花苷corchoionoside C	185414-25-9	α-CH₃	a	[31]
133	长春花苷roseoside	54835-70-0	β-CH₃	b	[40]
134	koniside	2411318-91-5		b	[32]
135	[R-(R, R)]-(1R)-3-[(4R)-4-羟基-2, 6, 6-三甲基-1-环己烯-1-基]-1-甲基丙基-β-D吡喃葡萄糖苷[R-(R, R)]-(1R)-3-[(4R)-4-hydroxy-2, 6, 6-trimethyl-cyclohexen-1-yl]-1-methylpropyl-β-D-glucopyranoside	160169-58-4		b	[40]
136	(3E)-4-[(3R, 4R, 5R)-4-(β-D-吡喃葡糖氧基)-3, 5-二羟基-2, 6, 6-三甲基-1-环己烯-1-基]-3-丁烯-2-酮(3E)-4-[(3R, 4R, 5R)-4-(β-D-glucopyranosyloxy)-3, 5-dihydroxy-2, 6, 6-trimethyl-1-cyclohexylen-1-yl]-3-buten-2-tone	875676-51-0		b	[40]
137	催吐萝芙木醇vomifoliol	23526-45-6		a	[35, 39]
138	去氢催吐萝芙木醇dehydrovomifoliol	15764-81-5		b	[36]
139	megastigmane	276870-26-9		a	[35]

序号 No.	化合物 compound	CAS编号 CAS number	取代基(R) substituent	品种 species	文献 ref.
140	5-羟甲基糠醛5-hydroxymethylfurfural	67-47-0		a	[18]
141	β-谷甾醇β-sitosterol	83-46-5	H	a-c	[30, 37-38]
142	胡萝卜苷daucosterol	474-58-8	Glu	a-c	[23, 37-38]
143	黄芪甲苷A astragaloside A	83207-58-3		b	[42]
144	豆甾醇stigmasterol	83-48-7		b	[29]
145	紫檀芪pterostilbene	537-42-8		b	[29]
146	琥珀酸succinic acid	110-15-6		a, c	[23, 37]
147	己二烯二酸muconic acid	505-70-4		c	[37]
148	硬脂酸stearic acid	57-11-4		b	[38]
149	1-(4-乙基苯基) -1, 2-乙二醇 1-(4-ethylphenyl)-1, 2-ethanediol	157403-37-7		b	[40]
150	反式植物醇trans-phytol	150-86-7		a	[35]
151	α-生育酚α-tocopherol	59-02-9		a	[35]
152	2-[4-(1-羟丙基)-3-甲氧基苯氧基]-1, 3-丙二醇 2-[4-(1-hydroxypropyl)-3-methoxyphenoxy]-1, 3-propanediol	71046-09-8		b	[38]
153	euscamine A	175993-01-8		a	[51]
154	euscamine B	175993-02-9		a	[51]
155	烟碱酸nicotinic acid	59-67-6		b	[36]
156	junipetrioloside A	195056-67-8		a	[31]

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Research Progress of Chemical Constituents and Pharmacological Effects of Euscaphis Plants

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序号 No.	化合物 compound	CAS编号 CAS number	取代基substituent¹⁾			品种 species	文献 ref.
序号 No.	化合物 compound	CAS编号 CAS number	R₁	R₂	R₃	品种 species	文献 ref.
76	去甲丁香色原酮noreugenin	1013-69-0	H	H	H	a-d	[33, 37-39]
77	去甲丁香色原酮-7-O-β-D-葡萄糖苷 noreugenin-7-O-β-D-glucoside	58108-99-9	H	β-D-Glu	H	d	[25, 33]
78	双花母草素biflorin	89701-85-9	β-D-Glu	H	H	b, d	[33, 38]
79	异双花母草素isobiflorin	152041-16-2	H	H	β-D-Glu	b, d	[33, 38]
80	2-甲基-5-羟基-7-甲氧基色原酮 5-hydroxy-7-methoxy-2-methylchromone	480-34-2	H	CH₃	H	d	[25]
81	槲皮素quercetin	117-39-5	H	OH		a-d	[20, 25, 35, 40]
82	异槲皮苷isoquercetin	482-35-9	β-D-Glu	OH		a-b	[23, 42]
83	槲皮素-3-O-α-D-阿拉伯糖 quercetin-3-O-α-D-arabinopyranoside	201610-60-8	α-D-Ara	OH		d	[33]
84	槲皮素-3-O-α-L-阿拉伯糖 quercetin-3-O-α-L-arabinopyranoside	22255-13-6	α-L-Ara	OH		b, d	[25, 38]
85	芦丁rutin	153-18-4	Rut	OH		b	[43]
86	山奈酚kaempferol	520-18-3	H	H		a-c	[20, 35]
87	紫云英苷astragalin	480-10-4	β-D-Glu	H		a	[44-45]
88	异鼠李素isorhamnetin	480-19-3	H	OCH₃		b-c	[20, 40]
89	异鼠李素-3-O-芸香糖苷 isorhamnetin-3-O-rutinoside	604-80-8	β-D-Rut	OCH₃		b-c	[20, 40]
90	异鼠李素-3-O-葡萄糖苷 isorhamnetin-3-O-glucoside	5041-82-7	β-D-Glu	OCH₃		a, c	[23, 27]
91	夏佛托苷schaftoside	51938-32-0	H			b	[40]
92	木犀草素-6-C-β-D-葡萄糖苷-8-C-α-阿拉伯糖苷 luteolin-6-C-β-D-glucopyranoside-8-C-α-arabino- pyranoside	59952-97-5	OH			b	[40]
93	矢车菊素-3-O-木糖葡萄糖苷 cyanidin-3-O-xylosylglucoside	63535-17-1				a	[45]