# Research Progress on Chemical Constituents ofZingiber officinale Roscoe

Authors: Yan Liu; Jincheng Liu; Yongqing Zhang
Journal: BioMed Research International
 (2019)

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## Abstract

Zingiber officinale Roscoe is commonly used in food and pharmaceutical products but can also be used in cosmetics and daily necessities. In recent years, many scholars have studied the chemical composition of Zingiber officinale Roscoe; therefore, it is necessary to comprehensively summarize the chemical composition of Zingiber officinale Roscoe in one article. The purpose of this paper is to provide a comprehensive review of the chemical constituents of Zingiber officinale Roscoe. The results show that Zingiber officinale Roscoe contains 194 types of volatile oils, 85 types of gingerol, and 28 types of diarylheptanoid compounds, which can lay a foundation for further applications of Zingiber officinale Roscoe.


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## Body

## 1. Introduction

Zingiber officinale Roscoe (ZOR, also Shengjiang in Chinese) is a perennial herb from the Zingiberaceae family, native to the Pacific Islands. It can be found in the Chinese provinces of Shandong, Henan, Hubei, Yunnan, Guangdong, Sichuan, and Jiangsu. ZOR is the fresh root of ginger, which is not only an important condiment but also one of the most commonly used Chinese medicines in clinical practice. Traditional Chinese medicine believes that ZOR has effects of releasing exterior and dissipating cold, arresting vomiting, resolving phlegm, and relieving coughs and can be used to treat fish and crab poison, stomach colds and vomiting, and cold sputum cough [1]. Modern pharmacological studies have shown that ZOR can promote digestion, improve blood circulation, lower blood lipids, lower blood sugar, relieve vestibular stimulation, and provide anti-inflammatory, antitumor, antimicrobial, and antioxidant effects [2–5]. Due to its rich active constituents, ZOR has been used in cosmetics [6], toothpaste [7], and health foods [8–10].All development and utilization of ZOR are based on its material composition. The chemical composition of ZOR is complex, includes more than 300 types of species, and can be broadly divided into three categories: volatile oils, gingerol, and diarylheptanoids [11–13]. In this paper, the existing research literature of ZOR is systematically summarized, and each chemical composition and its chemical structure are listed in detail, with a view to providing references for quality control, cultivation production, and further development of ZOR.


## 2. Constituents

### 2.1. Volatile Oils

Volatile oils, also known as ginger essential oils, are generally composed of terpenoids [14]. Ginger essential oils give ZOR a unique aromatic smell [11]. The volatile oil composition varies based on where the ZOR is harvested. Currently, the ingredients identified in the volatile oils of ZOR and their chemical structures are shown in Table 1.Table 1
Volatile oils in ZOR.
No.
Type
Name
Structure
Reference
1
Terpene
α-Terpinene
[15]
2
Terpene
α-Terpineol
[15]
3
Terpene
4-Terpineol
[15]
4
Terpene
Terpinolene
[15]
5
Terpene
γ-Terpinolene
[15]
6
Alcohol
Cineole
[15]
7
Alcohol
β-Eudesmol
[15]
8
Alcohol
Nerol
[15]
9
Alcohol
trans-Nerolidol
[15]
10
Alcohol
4-Isopropylbenzyl alcohol
[15]
11
Alcohol
3,7-Dimethylocta-1,6-dien-3-ol
[15]
12
Alcohol
3,7-Dimethyloct-6-en-1-yn-3-ol
[15]
13
Alcohol
3-Methylhexan-2-ol
[15]
14
Alcohol
cis-Piperitol
[15]
15
Alcohol
Borneol
[15]
16
Alcohol
Elemol
[15]
17
Alcohol
tau-Muurolol
[15]
18
Alcohol
2-Methoxy-1,7,7-trimethylbicyclo[2.2.1]heptane
[15]
19
Alcohol
1-Isopropyl-4-methylcyclohex-3-enol
[15]
20
Alcohol
2-Tetradecanol
[15]
21
Alcohol
Myrtenol
[15]
22
Alcohol
Citronellol
[15]
23
Alcohol
Geraniol
[15]
24
Alcohol
cis-Linalool oxide
[15]
25
Alcohol
4-Ethoxybutan-1-ol
[15]
26
Alcohol
α-Eudesmol
[15]
27
Alcohol
Nerolidol
[15]
28
Alcohol
Farnesol
[15]
29
Alcohol
trans-4-Isopropyl-1-methyl-2-cyclohexen-1-ol
[15]
30
Alcohol
cis-4-Isopropyl-1-methyl-2-cyclohexen-1-ol
[15]
31
Alcohol
2-Heptanol
[16]
32
Alcohol
1-Methoxy-2-methyl
[16]
33
Alcohol
cis-Sesquisabinene hydrate
[17]
34
Alcohol
cis-2-p-Menthen-1-ol
[17]
35
Alcohol
endo-Borneol
[17]
36
Alcohol
trans-Sabinene hydrate
[17]
37
Alcohol
2-Nonanol
[18]
38
Alcohol
Propanol
[18]
39
Alcohol
cis-β-Sesquiphellandrol
[18]
40
Alcohol
trans-β-Sesquiphellandrol
[18]
41
Alcohol
β-Santalol
[19]
42
Alcohol
Zingiberol
[19]
43
Alcohol
tau-Cadinol
[20]
44
Alcohol
Zingiberenol
[21]
45
Alcohol
2-Pinen-5-ol
[21]
46
Alcohol
Bornyl methyl ether
[21]
47
Alcohol
Isoborneol
[22]
48
Alcohol
2-Decanol
[22]
49
Alcohol
Fenchol
[22]
50
Alcohol
Linalool
[23]
51
Alcohol
Plinol
[23]
52
Alcohol
Camphenol
[23]
53
Alcohol
trans-2-Decen-1-ol
[23]
54
Alcohol
Hentriacontanol
[24]
55
Alcohol
10-O-β-D-Glucopyranosyl-hydroxyl cineole
[25]
56
Aldoketone
Butanal
[15]
57
Aldoketone
Germacrone
[15]
58
Aldoketone
2,6-Dimethylhept-5-enal
[15]
59
Aldoketone
2-Heptanone
[15]
60
Aldoketone
(E)-Citral
[15]
61
Aldoketone
(Z)-Citral
[15]
62
Aldoketone
2-Nonanone
[15]
63
Aldoketone
3-((3E,5E)-Deca-3,5-dienyl)cyclopentanone
[15]
64
Aldoketone
β-Cyclocitral
[15]
65
Aldoketone
2-Undecanone
[15]
66
Aldoketone
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
[15]
67
Aldoketone
(1R)-(–)-Myrtenal
[15]
68
Aldoketone
β-Citronellal
[15]
69
Aldoketone
Crypton
[15]
70
Aldoketone
4-Isopropylcyclohex-2-enone
[15]
71
Aldoketone
Camphor
[15]
72
Aldoketone
6-Methyl-5-hepten-2-one
[15]
73
Aldoketone
trans,trans-Farnesal
[15]
74
Aldoketone
Hexanal
[16]
75
Aldoketone
Neral
[17]
76
Aldoketone
Geranial
[17]
77
Aldoketone
Octanal
[17]
78
Aldoketone
Methyl heptenone
[18]
79
Aldoketone
Nonyl aldehyde
[18]
80
Aldoketone
Acetaldehyde
[18]
81
Aldoketone
Propionaldehyde
[18]
82
Aldoketone
Valeraldehyde
[18]
83
Aldoketone
Perillal
[19]
84
Aldoketone
(E)-Dodec-2-enal
[21]
85
Aldoketone
(Z)-3,7-Dimethylocta-3,6-dienal
[21]
86
Aldoketone
(E)-3,7-Dimethylocta-3,6-dienal
[21]
87
Aldoketone
(E)-Dec-2-enal
[21]
88
Aldoketone
Decanal
[23]
89
Aldoketone
Citronella
[23]
90
Aldoketone
2-Octenal
[21]
91
Aldoketone
Octanal
[26]
92
Aldoketone
Acetone
[26]
93
Acid
L-Bornyl acetate
[15]
94
Acid
Geranic acid
[15]
95
Acid
Undecanoic acid
[16]
96
Ester
Neryl acetate
[15]
97
Ester
Methyl 11-(cyclopent-2-enyl)undecanoate
[15]
98
Ester
Geranyl propionate
[15]
99
Ester
endo-Bornyl acetate
[15]
100
Ester
sec-Butyl acetate
[15]
101
Ester
3,7-Dimethyl-2,6-octadienyl acetate
[15]
102
Ester
Neryl propionate
[15]
103
Ester
Geraniol formate
[15]
104
Ester
Myrtenyl acetate
[15]
105
Ester
Geranyl acetate
[15]
106
Ester
Formic acid ethyl ester
[16]
107
Ester
Ethyl butanoate
[17]
108
Ester
Citronellyl acetate
[17]
109
Ester
Heptyl acetate
[17]
110
Ester
Methyl acetate
[18]
111
Ester
Ethyl acetate
[18]
112
Ester
Butyl acetate
[21]
113
Ester
2-Octyl acetate
[21]
114
Fat hydrocarbon
allo-Aromadendrene
[15]
115
Fat hydrocarbon
β-Sesquiphellandrene
[15]
116
Fat hydrocarbon
α-Cedrene
[15]
117
Fat hydrocarbon
β-Thujene
[15]
118
Fat hydrocarbon
Cadina-5,8-diene
[15]
119
Fat hydrocarbon
Bicyclo[2.2.1]heptane
[15]
120
Fat hydrocarbon
(E)-2,7-Dimethyloct-3-en-5-yne
[15]
121
Fat hydrocarbon
(Z)-2,6-Dimethylocta-2,6-diene
[15]
122
Fat hydrocarbon
(E)-3,7-Dimethylocta-1,3,6-triene
[15]
123
Fat hydrocarbon
β-Phellandrene
[15]
124
Fat hydrocarbon
α-Bergamotene
[15]
125
Fat hydrocarbon
α-Gurjunene
[15]
126
Fat hydrocarbon
Sabinene
[15]
127
Fat hydrocarbon
(+)-Cyclosativene
[15]
128
Fat hydrocarbon
(Z)-β-Farnesene
[15]
129
Fat hydrocarbon
(E)-β-Farnesene
[15]
130
Fat hydrocarbon
(Z,Z)-α-Farnesene
[15]
131
Fat hydrocarbon
Zingiberene
[15]
132
Fat hydrocarbon
α-Farnesene
[15]
133
Fat hydrocarbon
(E)-5-Methylocta-1,6-diene
[15]
134
Fat hydrocarbon
5-Methyloct-3-yne
[15]
135
Fat hydrocarbon
7-Methylocta-3,4-diene
[15]
136
Fat hydrocarbon
γ-Elemene
[15]
137
Fat hydrocarbon
γ-Humulene
[15]
138
Fat hydrocarbon
Thujopsene
[15]
139
Fat hydrocarbon
β-Elemene
[15]
140
Fat hydrocarbon
β-Bisabolene
[15]
141
Fat hydrocarbon
α-Pinene
[15]
142
Fat hydrocarbon
β-Pinene
[15]
143
Fat hydrocarbon
Caryophyllene
[15]
144
Fat hydrocarbon
β-Caryophyllene
[15]
145
Fat hydrocarbon
Tricyclene
[15]
146
Fat hydrocarbon
Moslene
[15]
147
Fat hydrocarbon
Cedrene
[15]
148
Fat hydrocarbon
(–)-allo-Aromadendrene
[15]
149
Fat hydrocarbon
Neoclovene
[15]
150
Fat hydrocarbon
3-Octyne
[15]
151
Fat hydrocarbon
1-Octene
[15]
152
Fat hydrocarbon
β-Myrcene
[15]
153
Fat hydrocarbon
β-Eudesmene
[15]
154
Fat hydrocarbon
Eudesma-3,7(11)-diene
[15]
155
Fat hydrocarbon
Caryophyllene
[15]
156
Fat hydrocarbon
Bicyclo[3.1.1]heptane
[15]
157
Fat hydrocarbon
1-Cyclopropylpentane
[15]
158
Fat hydrocarbon
3-Carene
[15]
159
Fat hydrocarbon
2-Carene
[15]
160
Fat hydrocarbon
(+)-Aromadendrene
[15]
161
Fat hydrocarbon
Fenchene
[16]
162
Fat hydrocarbon
δ-Elemene
[17]
163
Fat hydrocarbon
D-Limonene
[18, 22]
164
Fat hydrocarbon
β-Phellandrene
[18, 26]
165
Fat hydrocarbon
10-Epizonarene
[18]
166
Fat hydrocarbon
Octane
[18]
167
Fat hydrocarbon
Nonane
[18]
168
Fat hydrocarbon
α-Bergamotene
[19]
169
Fat hydrocarbon
β-Bisabolene
[20]
170
Fat hydrocarbon
τ-Epi-α-selinene
[20]
171
Fat hydrocarbon
4-Carene
[22]
172
Fat hydrocarbon
Camphene
[23]
173
Fat hydrocarbon
α-Phellandrene
[23]
174
Fat hydrocarbon
(Z)-3,7-Dimethylocta-1,3,6-triene
[27]
175
Fat hydrocarbon
Germacrene
[27]
176
Fat hydrocarbon
δ-Cadinene
[26]
177
Fat hydrocarbon
α-Cubebene
[26]
178
Fat hydrocarbon
α-Copaene
[26]
179
Arene
α-Curcumene
[15]
180
Arene
2-Isopropyltoluene
[15]
181
Arene
o-Cymene
[15]
182
Arene
Styrene
[17]
183
Arene
Methylbenzene
[17]
184
Arene
Cumene
[18]
185
Arene
p-Cymene
[19]
186
Others
p-Cymen-8-ol
[15]
187
Others
2-Acetoxy-1,8-cineole
[17]
188
Others
Diethyl sulphide
[18]
189
Others
Ethyl isopropyl sulphide
[18]
190
Others
Methyl allyl sulphide
[18]
191
Others
Dibutyl phthalate
[20]
192
Others
2-(3′-Methyl-2′-butenyl)-3-methylfuran
[21]
193
Others
Isoeugenol
[21]
194
Others
2-(2′,3′-Epoxy-3′-methylbutyl)-3-methylfuran
[21]


### 2.2. Gingerol

Gingerol is the spicy component of ZOR. It is a mixture of various substances, all of which contain the 3-methoxy-4-hydroxyphenyl functional group. Gingerols can be divided into gingerols, shogaols, paradols, zingerones, gingerdiones, and gingerdiols, according to the different fatty chains connected by this functional group [28, 29]. The structural formulas are given in Table 2.Table 2
Gingerols in ZOR.
No.
Name
Structure
R
R1
R2
n
Reference
195
3-Gingerol
H
H
—
1
[30]
196
4-Gingerol
H
H
—
2
[30]
197
5-Gingerol
H
H
—
3
[30]
198
6-Gingerol
H
H
—
4
[31, 32]
199
8-Gingerol
H
H
—
6
[31, 33]
200
10-Gingerol
H
H
—
8
[33]
201
12-Gingerol
H
H
—
10
[31, 32]
202
5-Methoxy-6-gingerol
H
CH3
—
4
[34]
203
Acetoxy-4-gingerol
H
COCH3
—
2
[34]
204
Acetoxy-6-gingerol
H
COCH3
—
4
[35]
205
Acetoxy-8-gingerol
H
COCH3
—
6
[34]
206
Acetoxy-10-gingerol
H
COCH3
—
8
[34]
207
4-Gingeryl methyl ether
CH3
H
—
2
[34]
208
6-Gingeryl methyl ether
CH3
H
—
4
[34]
209
6-Gingeryl methyl ether acetate
CH3
COCH3
—
4
[34]
210
6-Gingeryl diacetate
COCH3
COCH3
—
4
[36]
211
8-Gingeryl diacetate
COCH3
COCH3
—
6
[36]
212
10-Gingeryl diacetate
COCH3
COCH3
—
8
[36]
213
Zingerone
H
—
—
0
[36]
214
1-Paradol
H
—
—
1
[20]
215
2-Paradol
H
—
—
2
[20]
216
3-Paradol
H
—
—
3
[20]
217
4-Paradol
H
—
—
4
[20]
218
6-Paradol
H
—
—
6
[36, 37]
219
7-Paradol
H
—
—
7
[20]
220
8-Paradol
H
—
—
8
[36]
221
9-Paradol
H
—
—
9
[20]
222
10-Paradol
H
—
—
10
[36]
223
11-Paradol
H
—
—
11
[34]
224
13-Paradol
H
—
—
13
[34]
225
Methyl-6-paradol
CH3
—
—
6
[34, 38]
226
Methyl-8-paradol
CH3
—
—
8
[39]
227
Zingerone acetate
COCH3
—
—
0
[36]
228
6-Paradyl monoacetate
COCH3
—
—
6
[34]
229
8-Paradyl monoacetate
COCH3
—
—
8
[36]
230
6-Paradyl benzoate
COPh
—
—
6
[36]
231
1-Dehydro-3-gingerdione
—
—
—
1
[34]
232
1-Dehydro-6-gingerdione
—
—
—
4
[35, 40]
233
1-Dehydro-8-gingerdione
—
—
—
6
[35, 41]
234
1-Dehydro-10-gingerdione
—
—
—
8
[37, 42]
235
12-Dehydrogingerdione
—
—
—
10
[43]
236
6-Gingerdione
—
—
—
4
[44]
237
10-Gingerdione
—
—
—
8
[45]
238
4-Shogaol
H
—
—
2
[30, 44]
239
5-Shogaol
H
—
—
3
[39]
240
6-Shogaol
H
—
—
4
[35, 37]
241
8-Shogaol
H
—
—
6
[36, 37]
242
10-Shogaol
H
—
—
8
[36, 37]
243
12-Shogaol
H
—
—
10
[30, 44]
244
Methyl-4-shogaol
CH3
—
—
2
[39]
245
Methyl-6-shogaol
CH3
—
—
4
[34]
246
Methyl-8-shogaol
CH3
—
—
6
[34]
247
4-Gingerdiol
H
H
H
2
[30]
248
6-Gingerdiol
H
H
H
4
[44]
249
8-Gingerdiol
H
H
H
6
[44]
250
10-Gingerdiol
H
H
H
8
[44]
251
5-Acetoxy-4-gingerdiol
H
COCH3
H
2
[34]
252
5-Acetoxy-6-gingerdiol
H
COCH3
H
4
[46]
253
5-Acetoxy-7-gingerdiol
H
COCH3
H
5
[34]
254
Diacetoxy-4-gingerdiol
H
COCH3
COCH3
2
[46, 47]
255
Diacetoxy-6-gingerdiol
H
COCH3
COCH3
4
[46, 47]
256
Methyl-5-acetoxy-4-gingerdiol
CH3
COCH3
H
2
[34]
257
Methyl-5-acetoxy-6-gingerdiol
CH3
COCH3
H
4
[34]
258
Methyl diacetoxy-4-gingerdiol
CH3
COCH3
COCH3
2
[34]
259
Methyl diacetoxy-6-gingerdiol
CH3
COCH3
COCH3
4
[34]
260
Methyl diacetoxy-10-gingerdiol
CH3
COCH3
COCH3
8
[34]
261
6-Dihydroparadol
H
—
—
6
[34]
262
Acetoxy-6-dihydroparadol
Ac
—
—
6
[34]
263
1-(4′-Hydroxy-3′-methoxypheny-l)-7-octen-3-one
H
—
—
—
[34]
264
1-(4′-Hydroxy-3′-methoxypheny-l)-7-decen-3-one
CH2CH3
—
—
—
[34]
265
1-(4′-Hydroxy-3′-methoxypheny-l)-7-dodecen-3-one
(CH2)3CH3
—
—
—
[34]
266
4-Isogingerol
H
—
—
2
[34]
267
6-Isogingerol
H
—
—
4
[48]
268
Methyl-6-isogingerol
CH3
—
—
4
[34]
269
6-Zingerine
—
—
—
4
[49]
270
8-Zingerine
—
—
—
6
[49]
271
10-Zingerine
—
—
—
8
[49]
272
3-Dihydro-6-demethoxy shogaol
—
—
—
—
[34]
273
6-Isoshogaol
—
—
—
—
[44]
274
Dehydrozingerone
—
—
—
—
[36]
275
1-Dehydro-3-dihydro-10-gingerdione
—
—
—
—
[34, 44]
276
(Z)-10-Isoshogaol
—
—
—
—
[48]
277
(E)-10-Isoshogaol
—
—
—
—
[48]
278
β-Sitosterol
—
—
—
—
[50, 51]
279
Tetracosanoic acid
—
—
—
—
[50, 52]


### 2.3. Diarylheptanoids

Diarylheptanoid is a group of compounds with 1,7-disubstituted phenyl groups and heptane skeletons in its parent structure. Currently, it can be divided into linear diphenyl heptane and cyclic diphenyl heptane compounds with antioxidant activity [53]. The structural formulas are shown in Table 3.Table 3
Diarylheptanoids in ZOR.
No.
Name
Structure
R1
R2
R3
Reference
280
5-Hydroxy-1-(4′-hydroxy-3′-methoxyphenyl)-7-(4″-hydroxyphenyl)heptan-3-one
H
H
H
[32]
281
5-Hydroxy-1,7-bis(4′-hydroxy-3′-methoxyphenyl)heptan-3-one
H
OCH3
H
[32]
282
7-(3′,4′-Dihydroxy-5′-methoxyphenyl)-5-hydroxy-1-(4″-hydroxy-3″-methoxyphenyl)heptan-3-one
H
OCH3
OH
[54]
283
5-Hydroxy-7-(4′-hydroxy-3′,5′-dimethoxyphenyl)-1-(4″-hydroxy-3″-methoxyphenyl)heptan-3-one
H
OCH3
OCH3
[32]
284
5-Hydroxy-1-(4′-hydroxy-3′,5′-dimethoxyphenyl)-7-(4″-hydroxy-3″-methoxyphenyl)heptan-3-one
OCH3
OCH3
H
[55]
285
5-Hydroxy-1,7-bis(4′-hydroxy-3′,5′-dimethoxyphenyl)heptan-3-one
OCH3
OCH3
OCH3
[32]
286
(E)-7-(3′,4′-Dihydroxyphenyl)-1-(4″-hydroxy-3″-methoxyphenyl)hept-4-en-3-one
H
—
V
[55]
287
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-4-heptene-3-one
CH3
—
—
[55, 56]
288
3,5-Dihydroxy-1,7-bis(4′-hydroxy-3′-methoxyphenyl)heptane
H
H
CH3
[54–56]
289
1,7-bis(3′,4′-Dihydroxyphenyl)-3,5-diacetate heptane
COCH3
H
H
[55]
290
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-3,5-diacetate heptane
COCH3
H
CH3
[55–57]
291
1,7-bis(4′-Methoxy-3′-acetatephenyl)-3,5-diacetate heptane
COCH3
CH3
COCH3
[55]
292
1,7-bis(3′,4′-Diacetatephenyl)-3,5-diacetate heptane
COCH3
COCH3
COCH3
[55]
293
5-(6-(4-Hydroxy-3-methoxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol
H
—
—
[54, 58]
294
2-(4′-Hydroxy-3′-methoxyphenethyl)-6-(3″,4″-dihydroxy-5″-methoxyphenyl)-tetrahydro-2H-pyran-4-yl acetate
COCH3
—
—
[58]
295
7-(3′,4′-Dihydroxyphenyl)-1-(4″-hydroxy-3″-methoxyphenyl)-3,5-diacetate heptane
H
H
—
[55]
296
7-(4′-Hydroxy-3′-methoxyphenyl)-1-(4″,5″-dihydroxy-3″-methoxyphenyl)-3,5-diacetate heptane
OH
CH3
—
[54]
297
7-(4′-Hydroxy-3′-methoxyphenyl)-1-(4″-hydroxy-5″-methyl-3″-methoxyphenyl)-3,5-diacetate heptane
CH3
CH3
—
[55]
298
7-(4′-Hydroxy-3′-methoxyphenyl)-1-(4″-hydroxy-3″,5″-dimethoxyphenyl)-3,5-diacetate heptane
OCH3
CH3
—
[55, 56]
299
5-(6-(4-Hydroxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol
H
H
H
[25]
300
5-(6-(4-Hydroxy-3-methoxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol
H
H
OCH3
[54, 58]
301
5-(6-(4-Hydroxy-3-methoxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-2-hydroxy-3-methoxyphenyl acetate
H
COCH3
OCH3
[58]
302
2-(4′-Hydroxy-3′-methoxyphenethyl)-6-(3″,4″-dihydroxy-5″-methoxyphenyl)-tetrahydro-2H-pyran-4-yl acetate
COCH3
H
OCH3
[58]
303
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-5-oxoheptan-3-yl acetate
H
—
—
[57]
304
1,7-bis(3′-Methoxy-4′-acetatephenyl)-5-oxoheptan-3-yl acetate
COCH3
—
—
[57]
305
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-3,5-heptadione
—
—
—
[34]
306
(1E,6E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
—
—
—
[56]
307
2,4-bis(3,4-Dihydroxyphenethyl)pentanedioic acid
—
—
—
[59]


### 2.4. Others

#### 2.4.1. Proteins and Amino Acids

ZOR contains a variety of amino acids, including glutamate, aspartic acid, serine, glycine, threonine, alanine, cystine, valine, methionine, isoleucine, leucine, tyrosine, phenylalanine, lysine, histidine, arginine, proline [22, 60], and tryptophan [51].


#### 2.4.2. Sugars

ZOR also contains polysaccharides [44], cellulose, and soluble sugar.


#### 2.4.3. Organic Acids

ZOR contains oxalic acid, tartaric acid, lactic acid, acetic acid, citric acid, succinic acid, formic acid, and malonic acid [61].


#### 2.4.4. Inorganic Elements

ZOR has been shown to contain more than 20 inorganic elements such as K, Mg, Ga, Mn, P, Al, Zn, Fe, and Ba [44].


## 2.1. Volatile Oils

Volatile oils, also known as ginger essential oils, are generally composed of terpenoids [14]. Ginger essential oils give ZOR a unique aromatic smell [11]. The volatile oil composition varies based on where the ZOR is harvested. Currently, the ingredients identified in the volatile oils of ZOR and their chemical structures are shown in Table 1.Table 1
Volatile oils in ZOR.
No.
Type
Name
Structure
Reference
1
Terpene
α-Terpinene
[15]
2
Terpene
α-Terpineol
[15]
3
Terpene
4-Terpineol
[15]
4
Terpene
Terpinolene
[15]
5
Terpene
γ-Terpinolene
[15]
6
Alcohol
Cineole
[15]
7
Alcohol
β-Eudesmol
[15]
8
Alcohol
Nerol
[15]
9
Alcohol
trans-Nerolidol
[15]
10
Alcohol
4-Isopropylbenzyl alcohol
[15]
11
Alcohol
3,7-Dimethylocta-1,6-dien-3-ol
[15]
12
Alcohol
3,7-Dimethyloct-6-en-1-yn-3-ol
[15]
13
Alcohol
3-Methylhexan-2-ol
[15]
14
Alcohol
cis-Piperitol
[15]
15
Alcohol
Borneol
[15]
16
Alcohol
Elemol
[15]
17
Alcohol
tau-Muurolol
[15]
18
Alcohol
2-Methoxy-1,7,7-trimethylbicyclo[2.2.1]heptane
[15]
19
Alcohol
1-Isopropyl-4-methylcyclohex-3-enol
[15]
20
Alcohol
2-Tetradecanol
[15]
21
Alcohol
Myrtenol
[15]
22
Alcohol
Citronellol
[15]
23
Alcohol
Geraniol
[15]
24
Alcohol
cis-Linalool oxide
[15]
25
Alcohol
4-Ethoxybutan-1-ol
[15]
26
Alcohol
α-Eudesmol
[15]
27
Alcohol
Nerolidol
[15]
28
Alcohol
Farnesol
[15]
29
Alcohol
trans-4-Isopropyl-1-methyl-2-cyclohexen-1-ol
[15]
30
Alcohol
cis-4-Isopropyl-1-methyl-2-cyclohexen-1-ol
[15]
31
Alcohol
2-Heptanol
[16]
32
Alcohol
1-Methoxy-2-methyl
[16]
33
Alcohol
cis-Sesquisabinene hydrate
[17]
34
Alcohol
cis-2-p-Menthen-1-ol
[17]
35
Alcohol
endo-Borneol
[17]
36
Alcohol
trans-Sabinene hydrate
[17]
37
Alcohol
2-Nonanol
[18]
38
Alcohol
Propanol
[18]
39
Alcohol
cis-β-Sesquiphellandrol
[18]
40
Alcohol
trans-β-Sesquiphellandrol
[18]
41
Alcohol
β-Santalol
[19]
42
Alcohol
Zingiberol
[19]
43
Alcohol
tau-Cadinol
[20]
44
Alcohol
Zingiberenol
[21]
45
Alcohol
2-Pinen-5-ol
[21]
46
Alcohol
Bornyl methyl ether
[21]
47
Alcohol
Isoborneol
[22]
48
Alcohol
2-Decanol
[22]
49
Alcohol
Fenchol
[22]
50
Alcohol
Linalool
[23]
51
Alcohol
Plinol
[23]
52
Alcohol
Camphenol
[23]
53
Alcohol
trans-2-Decen-1-ol
[23]
54
Alcohol
Hentriacontanol
[24]
55
Alcohol
10-O-β-D-Glucopyranosyl-hydroxyl cineole
[25]
56
Aldoketone
Butanal
[15]
57
Aldoketone
Germacrone
[15]
58
Aldoketone
2,6-Dimethylhept-5-enal
[15]
59
Aldoketone
2-Heptanone
[15]
60
Aldoketone
(E)-Citral
[15]
61
Aldoketone
(Z)-Citral
[15]
62
Aldoketone
2-Nonanone
[15]
63
Aldoketone
3-((3E,5E)-Deca-3,5-dienyl)cyclopentanone
[15]
64
Aldoketone
β-Cyclocitral
[15]
65
Aldoketone
2-Undecanone
[15]
66
Aldoketone
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
[15]
67
Aldoketone
(1R)-(–)-Myrtenal
[15]
68
Aldoketone
β-Citronellal
[15]
69
Aldoketone
Crypton
[15]
70
Aldoketone
4-Isopropylcyclohex-2-enone
[15]
71
Aldoketone
Camphor
[15]
72
Aldoketone
6-Methyl-5-hepten-2-one
[15]
73
Aldoketone
trans,trans-Farnesal
[15]
74
Aldoketone
Hexanal
[16]
75
Aldoketone
Neral
[17]
76
Aldoketone
Geranial
[17]
77
Aldoketone
Octanal
[17]
78
Aldoketone
Methyl heptenone
[18]
79
Aldoketone
Nonyl aldehyde
[18]
80
Aldoketone
Acetaldehyde
[18]
81
Aldoketone
Propionaldehyde
[18]
82
Aldoketone
Valeraldehyde
[18]
83
Aldoketone
Perillal
[19]
84
Aldoketone
(E)-Dodec-2-enal
[21]
85
Aldoketone
(Z)-3,7-Dimethylocta-3,6-dienal
[21]
86
Aldoketone
(E)-3,7-Dimethylocta-3,6-dienal
[21]
87
Aldoketone
(E)-Dec-2-enal
[21]
88
Aldoketone
Decanal
[23]
89
Aldoketone
Citronella
[23]
90
Aldoketone
2-Octenal
[21]
91
Aldoketone
Octanal
[26]
92
Aldoketone
Acetone
[26]
93
Acid
L-Bornyl acetate
[15]
94
Acid
Geranic acid
[15]
95
Acid
Undecanoic acid
[16]
96
Ester
Neryl acetate
[15]
97
Ester
Methyl 11-(cyclopent-2-enyl)undecanoate
[15]
98
Ester
Geranyl propionate
[15]
99
Ester
endo-Bornyl acetate
[15]
100
Ester
sec-Butyl acetate
[15]
101
Ester
3,7-Dimethyl-2,6-octadienyl acetate
[15]
102
Ester
Neryl propionate
[15]
103
Ester
Geraniol formate
[15]
104
Ester
Myrtenyl acetate
[15]
105
Ester
Geranyl acetate
[15]
106
Ester
Formic acid ethyl ester
[16]
107
Ester
Ethyl butanoate
[17]
108
Ester
Citronellyl acetate
[17]
109
Ester
Heptyl acetate
[17]
110
Ester
Methyl acetate
[18]
111
Ester
Ethyl acetate
[18]
112
Ester
Butyl acetate
[21]
113
Ester
2-Octyl acetate
[21]
114
Fat hydrocarbon
allo-Aromadendrene
[15]
115
Fat hydrocarbon
β-Sesquiphellandrene
[15]
116
Fat hydrocarbon
α-Cedrene
[15]
117
Fat hydrocarbon
β-Thujene
[15]
118
Fat hydrocarbon
Cadina-5,8-diene
[15]
119
Fat hydrocarbon
Bicyclo[2.2.1]heptane
[15]
120
Fat hydrocarbon
(E)-2,7-Dimethyloct-3-en-5-yne
[15]
121
Fat hydrocarbon
(Z)-2,6-Dimethylocta-2,6-diene
[15]
122
Fat hydrocarbon
(E)-3,7-Dimethylocta-1,3,6-triene
[15]
123
Fat hydrocarbon
β-Phellandrene
[15]
124
Fat hydrocarbon
α-Bergamotene
[15]
125
Fat hydrocarbon
α-Gurjunene
[15]
126
Fat hydrocarbon
Sabinene
[15]
127
Fat hydrocarbon
(+)-Cyclosativene
[15]
128
Fat hydrocarbon
(Z)-β-Farnesene
[15]
129
Fat hydrocarbon
(E)-β-Farnesene
[15]
130
Fat hydrocarbon
(Z,Z)-α-Farnesene
[15]
131
Fat hydrocarbon
Zingiberene
[15]
132
Fat hydrocarbon
α-Farnesene
[15]
133
Fat hydrocarbon
(E)-5-Methylocta-1,6-diene
[15]
134
Fat hydrocarbon
5-Methyloct-3-yne
[15]
135
Fat hydrocarbon
7-Methylocta-3,4-diene
[15]
136
Fat hydrocarbon
γ-Elemene
[15]
137
Fat hydrocarbon
γ-Humulene
[15]
138
Fat hydrocarbon
Thujopsene
[15]
139
Fat hydrocarbon
β-Elemene
[15]
140
Fat hydrocarbon
β-Bisabolene
[15]
141
Fat hydrocarbon
α-Pinene
[15]
142
Fat hydrocarbon
β-Pinene
[15]
143
Fat hydrocarbon
Caryophyllene
[15]
144
Fat hydrocarbon
β-Caryophyllene
[15]
145
Fat hydrocarbon
Tricyclene
[15]
146
Fat hydrocarbon
Moslene
[15]
147
Fat hydrocarbon
Cedrene
[15]
148
Fat hydrocarbon
(–)-allo-Aromadendrene
[15]
149
Fat hydrocarbon
Neoclovene
[15]
150
Fat hydrocarbon
3-Octyne
[15]
151
Fat hydrocarbon
1-Octene
[15]
152
Fat hydrocarbon
β-Myrcene
[15]
153
Fat hydrocarbon
β-Eudesmene
[15]
154
Fat hydrocarbon
Eudesma-3,7(11)-diene
[15]
155
Fat hydrocarbon
Caryophyllene
[15]
156
Fat hydrocarbon
Bicyclo[3.1.1]heptane
[15]
157
Fat hydrocarbon
1-Cyclopropylpentane
[15]
158
Fat hydrocarbon
3-Carene
[15]
159
Fat hydrocarbon
2-Carene
[15]
160
Fat hydrocarbon
(+)-Aromadendrene
[15]
161
Fat hydrocarbon
Fenchene
[16]
162
Fat hydrocarbon
δ-Elemene
[17]
163
Fat hydrocarbon
D-Limonene
[18, 22]
164
Fat hydrocarbon
β-Phellandrene
[18, 26]
165
Fat hydrocarbon
10-Epizonarene
[18]
166
Fat hydrocarbon
Octane
[18]
167
Fat hydrocarbon
Nonane
[18]
168
Fat hydrocarbon
α-Bergamotene
[19]
169
Fat hydrocarbon
β-Bisabolene
[20]
170
Fat hydrocarbon
τ-Epi-α-selinene
[20]
171
Fat hydrocarbon
4-Carene
[22]
172
Fat hydrocarbon
Camphene
[23]
173
Fat hydrocarbon
α-Phellandrene
[23]
174
Fat hydrocarbon
(Z)-3,7-Dimethylocta-1,3,6-triene
[27]
175
Fat hydrocarbon
Germacrene
[27]
176
Fat hydrocarbon
δ-Cadinene
[26]
177
Fat hydrocarbon
α-Cubebene
[26]
178
Fat hydrocarbon
α-Copaene
[26]
179
Arene
α-Curcumene
[15]
180
Arene
2-Isopropyltoluene
[15]
181
Arene
o-Cymene
[15]
182
Arene
Styrene
[17]
183
Arene
Methylbenzene
[17]
184
Arene
Cumene
[18]
185
Arene
p-Cymene
[19]
186
Others
p-Cymen-8-ol
[15]
187
Others
2-Acetoxy-1,8-cineole
[17]
188
Others
Diethyl sulphide
[18]
189
Others
Ethyl isopropyl sulphide
[18]
190
Others
Methyl allyl sulphide
[18]
191
Others
Dibutyl phthalate
[20]
192
Others
2-(3′-Methyl-2′-butenyl)-3-methylfuran
[21]
193
Others
Isoeugenol
[21]
194
Others
2-(2′,3′-Epoxy-3′-methylbutyl)-3-methylfuran
[21]


## 2.2. Gingerol

Gingerol is the spicy component of ZOR. It is a mixture of various substances, all of which contain the 3-methoxy-4-hydroxyphenyl functional group. Gingerols can be divided into gingerols, shogaols, paradols, zingerones, gingerdiones, and gingerdiols, according to the different fatty chains connected by this functional group [28, 29]. The structural formulas are given in Table 2.Table 2
Gingerols in ZOR.
No.
Name
Structure
R
R1
R2
n
Reference
195
3-Gingerol
H
H
—
1
[30]
196
4-Gingerol
H
H
—
2
[30]
197
5-Gingerol
H
H
—
3
[30]
198
6-Gingerol
H
H
—
4
[31, 32]
199
8-Gingerol
H
H
—
6
[31, 33]
200
10-Gingerol
H
H
—
8
[33]
201
12-Gingerol
H
H
—
10
[31, 32]
202
5-Methoxy-6-gingerol
H
CH3
—
4
[34]
203
Acetoxy-4-gingerol
H
COCH3
—
2
[34]
204
Acetoxy-6-gingerol
H
COCH3
—
4
[35]
205
Acetoxy-8-gingerol
H
COCH3
—
6
[34]
206
Acetoxy-10-gingerol
H
COCH3
—
8
[34]
207
4-Gingeryl methyl ether
CH3
H
—
2
[34]
208
6-Gingeryl methyl ether
CH3
H
—
4
[34]
209
6-Gingeryl methyl ether acetate
CH3
COCH3
—
4
[34]
210
6-Gingeryl diacetate
COCH3
COCH3
—
4
[36]
211
8-Gingeryl diacetate
COCH3
COCH3
—
6
[36]
212
10-Gingeryl diacetate
COCH3
COCH3
—
8
[36]
213
Zingerone
H
—
—
0
[36]
214
1-Paradol
H
—
—
1
[20]
215
2-Paradol
H
—
—
2
[20]
216
3-Paradol
H
—
—
3
[20]
217
4-Paradol
H
—
—
4
[20]
218
6-Paradol
H
—
—
6
[36, 37]
219
7-Paradol
H
—
—
7
[20]
220
8-Paradol
H
—
—
8
[36]
221
9-Paradol
H
—
—
9
[20]
222
10-Paradol
H
—
—
10
[36]
223
11-Paradol
H
—
—
11
[34]
224
13-Paradol
H
—
—
13
[34]
225
Methyl-6-paradol
CH3
—
—
6
[34, 38]
226
Methyl-8-paradol
CH3
—
—
8
[39]
227
Zingerone acetate
COCH3
—
—
0
[36]
228
6-Paradyl monoacetate
COCH3
—
—
6
[34]
229
8-Paradyl monoacetate
COCH3
—
—
8
[36]
230
6-Paradyl benzoate
COPh
—
—
6
[36]
231
1-Dehydro-3-gingerdione
—
—
—
1
[34]
232
1-Dehydro-6-gingerdione
—
—
—
4
[35, 40]
233
1-Dehydro-8-gingerdione
—
—
—
6
[35, 41]
234
1-Dehydro-10-gingerdione
—
—
—
8
[37, 42]
235
12-Dehydrogingerdione
—
—
—
10
[43]
236
6-Gingerdione
—
—
—
4
[44]
237
10-Gingerdione
—
—
—
8
[45]
238
4-Shogaol
H
—
—
2
[30, 44]
239
5-Shogaol
H
—
—
3
[39]
240
6-Shogaol
H
—
—
4
[35, 37]
241
8-Shogaol
H
—
—
6
[36, 37]
242
10-Shogaol
H
—
—
8
[36, 37]
243
12-Shogaol
H
—
—
10
[30, 44]
244
Methyl-4-shogaol
CH3
—
—
2
[39]
245
Methyl-6-shogaol
CH3
—
—
4
[34]
246
Methyl-8-shogaol
CH3
—
—
6
[34]
247
4-Gingerdiol
H
H
H
2
[30]
248
6-Gingerdiol
H
H
H
4
[44]
249
8-Gingerdiol
H
H
H
6
[44]
250
10-Gingerdiol
H
H
H
8
[44]
251
5-Acetoxy-4-gingerdiol
H
COCH3
H
2
[34]
252
5-Acetoxy-6-gingerdiol
H
COCH3
H
4
[46]
253
5-Acetoxy-7-gingerdiol
H
COCH3
H
5
[34]
254
Diacetoxy-4-gingerdiol
H
COCH3
COCH3
2
[46, 47]
255
Diacetoxy-6-gingerdiol
H
COCH3
COCH3
4
[46, 47]
256
Methyl-5-acetoxy-4-gingerdiol
CH3
COCH3
H
2
[34]
257
Methyl-5-acetoxy-6-gingerdiol
CH3
COCH3
H
4
[34]
258
Methyl diacetoxy-4-gingerdiol
CH3
COCH3
COCH3
2
[34]
259
Methyl diacetoxy-6-gingerdiol
CH3
COCH3
COCH3
4
[34]
260
Methyl diacetoxy-10-gingerdiol
CH3
COCH3
COCH3
8
[34]
261
6-Dihydroparadol
H
—
—
6
[34]
262
Acetoxy-6-dihydroparadol
Ac
—
—
6
[34]
263
1-(4′-Hydroxy-3′-methoxypheny-l)-7-octen-3-one
H
—
—
—
[34]
264
1-(4′-Hydroxy-3′-methoxypheny-l)-7-decen-3-one
CH2CH3
—
—
—
[34]
265
1-(4′-Hydroxy-3′-methoxypheny-l)-7-dodecen-3-one
(CH2)3CH3
—
—
—
[34]
266
4-Isogingerol
H
—
—
2
[34]
267
6-Isogingerol
H
—
—
4
[48]
268
Methyl-6-isogingerol
CH3
—
—
4
[34]
269
6-Zingerine
—
—
—
4
[49]
270
8-Zingerine
—
—
—
6
[49]
271
10-Zingerine
—
—
—
8
[49]
272
3-Dihydro-6-demethoxy shogaol
—
—
—
—
[34]
273
6-Isoshogaol
—
—
—
—
[44]
274
Dehydrozingerone
—
—
—
—
[36]
275
1-Dehydro-3-dihydro-10-gingerdione
—
—
—
—
[34, 44]
276
(Z)-10-Isoshogaol
—
—
—
—
[48]
277
(E)-10-Isoshogaol
—
—
—
—
[48]
278
β-Sitosterol
—
—
—
—
[50, 51]
279
Tetracosanoic acid
—
—
—
—
[50, 52]


## 2.3. Diarylheptanoids

Diarylheptanoid is a group of compounds with 1,7-disubstituted phenyl groups and heptane skeletons in its parent structure. Currently, it can be divided into linear diphenyl heptane and cyclic diphenyl heptane compounds with antioxidant activity [53]. The structural formulas are shown in Table 3.Table 3
Diarylheptanoids in ZOR.
No.
Name
Structure
R1
R2
R3
Reference
280
5-Hydroxy-1-(4′-hydroxy-3′-methoxyphenyl)-7-(4″-hydroxyphenyl)heptan-3-one
H
H
H
[32]
281
5-Hydroxy-1,7-bis(4′-hydroxy-3′-methoxyphenyl)heptan-3-one
H
OCH3
H
[32]
282
7-(3′,4′-Dihydroxy-5′-methoxyphenyl)-5-hydroxy-1-(4″-hydroxy-3″-methoxyphenyl)heptan-3-one
H
OCH3
OH
[54]
283
5-Hydroxy-7-(4′-hydroxy-3′,5′-dimethoxyphenyl)-1-(4″-hydroxy-3″-methoxyphenyl)heptan-3-one
H
OCH3
OCH3
[32]
284
5-Hydroxy-1-(4′-hydroxy-3′,5′-dimethoxyphenyl)-7-(4″-hydroxy-3″-methoxyphenyl)heptan-3-one
OCH3
OCH3
H
[55]
285
5-Hydroxy-1,7-bis(4′-hydroxy-3′,5′-dimethoxyphenyl)heptan-3-one
OCH3
OCH3
OCH3
[32]
286
(E)-7-(3′,4′-Dihydroxyphenyl)-1-(4″-hydroxy-3″-methoxyphenyl)hept-4-en-3-one
H
—
V
[55]
287
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-4-heptene-3-one
CH3
—
—
[55, 56]
288
3,5-Dihydroxy-1,7-bis(4′-hydroxy-3′-methoxyphenyl)heptane
H
H
CH3
[54–56]
289
1,7-bis(3′,4′-Dihydroxyphenyl)-3,5-diacetate heptane
COCH3
H
H
[55]
290
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-3,5-diacetate heptane
COCH3
H
CH3
[55–57]
291
1,7-bis(4′-Methoxy-3′-acetatephenyl)-3,5-diacetate heptane
COCH3
CH3
COCH3
[55]
292
1,7-bis(3′,4′-Diacetatephenyl)-3,5-diacetate heptane
COCH3
COCH3
COCH3
[55]
293
5-(6-(4-Hydroxy-3-methoxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol
H
—
—
[54, 58]
294
2-(4′-Hydroxy-3′-methoxyphenethyl)-6-(3″,4″-dihydroxy-5″-methoxyphenyl)-tetrahydro-2H-pyran-4-yl acetate
COCH3
—
—
[58]
295
7-(3′,4′-Dihydroxyphenyl)-1-(4″-hydroxy-3″-methoxyphenyl)-3,5-diacetate heptane
H
H
—
[55]
296
7-(4′-Hydroxy-3′-methoxyphenyl)-1-(4″,5″-dihydroxy-3″-methoxyphenyl)-3,5-diacetate heptane
OH
CH3
—
[54]
297
7-(4′-Hydroxy-3′-methoxyphenyl)-1-(4″-hydroxy-5″-methyl-3″-methoxyphenyl)-3,5-diacetate heptane
CH3
CH3
—
[55]
298
7-(4′-Hydroxy-3′-methoxyphenyl)-1-(4″-hydroxy-3″,5″-dimethoxyphenyl)-3,5-diacetate heptane
OCH3
CH3
—
[55, 56]
299
5-(6-(4-Hydroxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol
H
H
H
[25]
300
5-(6-(4-Hydroxy-3-methoxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol
H
H
OCH3
[54, 58]
301
5-(6-(4-Hydroxy-3-methoxyphenethyl)-4-hydroxy-tetrahydro-2H-pyran-2-yl)-2-hydroxy-3-methoxyphenyl acetate
H
COCH3
OCH3
[58]
302
2-(4′-Hydroxy-3′-methoxyphenethyl)-6-(3″,4″-dihydroxy-5″-methoxyphenyl)-tetrahydro-2H-pyran-4-yl acetate
COCH3
H
OCH3
[58]
303
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-5-oxoheptan-3-yl acetate
H
—
—
[57]
304
1,7-bis(3′-Methoxy-4′-acetatephenyl)-5-oxoheptan-3-yl acetate
COCH3
—
—
[57]
305
1,7-bis(4′-Hydroxy-3′-methoxyphenyl)-3,5-heptadione
—
—
—
[34]
306
(1E,6E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
—
—
—
[56]
307
2,4-bis(3,4-Dihydroxyphenethyl)pentanedioic acid
—
—
—
[59]


## 2.4. Others

### 2.4.1. Proteins and Amino Acids

ZOR contains a variety of amino acids, including glutamate, aspartic acid, serine, glycine, threonine, alanine, cystine, valine, methionine, isoleucine, leucine, tyrosine, phenylalanine, lysine, histidine, arginine, proline [22, 60], and tryptophan [51].


### 2.4.2. Sugars

ZOR also contains polysaccharides [44], cellulose, and soluble sugar.


### 2.4.3. Organic Acids

ZOR contains oxalic acid, tartaric acid, lactic acid, acetic acid, citric acid, succinic acid, formic acid, and malonic acid [61].


### 2.4.4. Inorganic Elements

ZOR has been shown to contain more than 20 inorganic elements such as K, Mg, Ga, Mn, P, Al, Zn, Fe, and Ba [44].


## 2.4.1. Proteins and Amino Acids

ZOR contains a variety of amino acids, including glutamate, aspartic acid, serine, glycine, threonine, alanine, cystine, valine, methionine, isoleucine, leucine, tyrosine, phenylalanine, lysine, histidine, arginine, proline [22, 60], and tryptophan [51].


## 2.4.2. Sugars

ZOR also contains polysaccharides [44], cellulose, and soluble sugar.


## 2.4.3. Organic Acids

ZOR contains oxalic acid, tartaric acid, lactic acid, acetic acid, citric acid, succinic acid, formic acid, and malonic acid [61].


## 2.4.4. Inorganic Elements

ZOR has been shown to contain more than 20 inorganic elements such as K, Mg, Ga, Mn, P, Al, Zn, Fe, and Ba [44].


## 3. Discussion

Various gingers have different regions and chemical compositions. Jolad [30] conducted quantitative analysis on the extracts of dichloromethane from Chinese white ginger and Japanese turmeric and found that the highest content of 6-gingerol was 28% and 34%, respectively. The next highest concentrations were 8-gingerol and 10-gingerol, and the lowest content of 6-shogaol was only 0.35%. Onyenekwe [62] determined that the main components of the volatile oils of Nigerian ginger were terpenoids such as zingiberene (29.5%) and β-sesquiphellandrene (18.4%), which were quite different from those of ginger grown in other regions. Another study showed the volatile oil content of ginger grown in five different areas of China (Shandong Laiwu, Anhui Tongling, Shandong Anqiu, Guangdong Guangzhou, and Hunan Rucheng) was 0.13%, 0.23%, 0.30%, 0.14%, and 0.17% [63], respectively. 6-Gingerol is often the quality standard for ginger, where the ginger found in Qianwei, Sichuan Province, shows a higher effective content of 6-gingerol than that of the pharmacopoeia standard of the People’s Republic of China [64, 65]. The concentrations of 6-gingerol and 6-zingiberol of ginger grown in different regions of China vary greatly, which may be related to the growth environment [66]. Mature and fresh ginger extracts contain the same chemical components, but the difference is in the relative content of each component. Ginger oleoresin in mature ginger is significantly higher than that in fresh ginger. In aromatic terpenoids, the contents of 2-acetoxy-1,8-cineole, β-citronellal, citral, geraniol, geranyl acetate, and zingiberene in mature ginger are lower than those in fresh ginger. The relative content of α-curcumene in mature ginger was higher than that in fresh ginger. In spicy gingerol compounds, the relative content of gingerol in mature ginger is higher than that in fresh ginger, which may be the result of further synthesis and accumulation of gingerol components in the process of continued growth of mature ginger in the second year [48]. The varieties of ginger with the highest oil content are Laiwu ginger, Japanese ginger, Shannong 1 ginger, Shannong 2 ginger, and Anqiu big ginger, with concentrations of 4.56%, 4.42%, 4.52%, 4.50%, and 4.35%, respectively. Average oil contents of 3.45% and 3.16% were found in Jinchang ginger and Chinger, respectively. The lowest oil extraction rates were found in Anqiu small ginger, Fangzhou ginger, and Jinshi ginger, which were 2.95%, 2.60%, and 1.55%, respectively [48].Ginger, as a kind of food and medicine, has many functions, such as antioxidant, anti-inflammatory, antimicrobial, anticancer, antiobesity, antidiabetic, antinausea, antiemetic, antiallergic, neuroprotective, hepatoprotective, cardiovascular protective, and respiratory protective activities [67]. Currently, most studies of the bioactive components of ginger focus on ginger volatile oil, gingerol, shogaol, and zingerone compounds. Ginger essential oil can effectively improve the antioxidant capacity of the liver, reduce inflammatory response, and protect against fatty liver [68]. The antioxidant compounds in ginger are primarily gingerol and diarylheptanoid. Substituents on alkyl chains contribute to free radical scavenging and oxidation inhibition of lipids [69]. Antioxidant activity is typically derived from gingerols, shogaols, and some related phenolic ketone derivatives [70]. Gingerols are spicy ingredients in which 6-gingerol shows the highest biological activity, so 6-gingerol is often used as an indicator of ginger quality [71]. 6-Gingerol has been used to inhibit angiogenesis in vivo and in vitro [72]. It has been shown to have anticancer and antigastric ulcer properties while suppressing central nervous stimulation and various pharmacological activities [73, 74]. 6-Gingerol has been used to treat tumors by regulating the apoptosis gene by reversing the abnormal expression of tumor cell genes. It can also affect the apoptosis signal transduction pathway and induce apoptosis [75]. 8-Gingerol and 10-gingerol have good inhibitory effects on the activity of various tumor cells, where the inhibitory effects are somewhat different. The two may affect the phosphorylation level of the MAPK pathway proteins ERK and P38, leading to G1 phase arrest of breast cancer cells, thus applying inhibitory effects on the proliferation of tumor cells [76]. The main components of strong heart are gingerol and 6-shogaol [77]. The effects of 6-gingerol and 6-shogaol on blood pressure have been shown to induce a hypotensive effect at low doses, while high doses have shown a three-phase reaction. Initially, blood pressure drops rapidly, then rises, and then provides a hypotensive effect at later stages [78]. Ginger polysaccharide has biological activities such as antitumor, hypoglycemic, lipid-lowering, immune regulation, antivirus, and antifatigue [79].


## 4. Conclusion

ZOR is a widely used drug and food in clinical and daily life and has been used in the prevention and treatment of the digestive, circulatory, respiratory, and central nervous system diseases and other diseases. In this paper, the chemical constituents found in ZOR in recent years are summarized, and the results show that more than 300 chemical constituents are identified from the extracts of ZOR, including 194 types of volatile oil, 85 types of gingerol, and 28 types of diarylheptanoids compounds. From this, it can be clearly observed that ZOR has a complex chemical composition. The interactions between the components provide the clinical effects; therefore, it is necessary to further study the chemical composition and pharmacological action of ginger, for further applications. Exploring the mechanism by which different components perform the same effects is a new way to develop drugs in the future; for example, 4-terpineol and beta-sitosterol can act on the two targets of the 5-hydroxytryptamine receptor 3A and the mu-type opioid receptor, respectively, and provide corresponding therapeutic effects on diarrhea and dysentery. This can provide ideas for the research and development of new drugs and lay a foundation for further applications of ZOR.



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*Source: 5370823-2019-12-21.xml*