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Review

Systematic Review of Chemical Constituents in the Genus Lycium (Solanaceae)

by
Dan Qian
1,2,
Yaxing Zhao
3,
Guang Yang
2 and
Luqi Huang
2,*
1
Experimental Research Center, China Academy of Chinese Medical Sciences, Beijing 100700, China
2
The State Key Laboratory Breeding Base of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China
3
School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(6), 911; https://doi.org/10.3390/molecules22060911
Submission received: 27 April 2017 / Revised: 5 June 2017 / Accepted: 5 June 2017 / Published: 8 June 2017
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Versions Notes

Abstract

:
The Lycium genus is widely used as a traditional Chinese medicine and functional food. Many of the chemical constituents of the genus Lycium were reported previously. In this review, in addition to the polysaccharides, we have enumerated 355 chemical constituents and nutrients, including 22 glycerogalactolipids, 29 phenylpropanoids, 10 coumarins, 13 lignans, 32 flavonoids, 37 amides, 72 alkaloids, four anthraquinones, 32 organic acids, 39 terpenoids, 57 sterols, steroids, and their derivatives, five peptides and three other constituents. This comprehensive study could lay the foundation for further research on the Lycium genus.

1. Introduction

Lycium is one of the genera in the Solanaceae family, comprising 80 species, seven of which are found in China [1]. These species are all deciduous shrubbery, possessing a highly similar morphology and structure. The Lycium genus has been an important source of medicines and nutrient supplements for thousands of years in Southeast Asia, especially in China. Two species in particular, Lycium barbarum and Lycium chinense, have been widely used as traditional Chinese medicinal herbs for centuries and L. barbarum is currently widely cultivated in China.
Goji berries (Chinese name Gouqizi), which are derived from the fruits of Lycium Linn, have been used as traditional herbs for a long time in China for their benefits of replenishing vital essence to improve eyesight, nourish the liver and kidneys. Lycii cortex is a “heat cleansing” drug that is derived from the root bark of L. chinense and L. barbarum [2]. Goji berries and Cortex Lycii have demonstrated good therapeutic effects in some chronic diseases such as hectic fever, night sweats, cough, hemoptysis, and diabetes. Recently, medical research has indicated that these fruits and root bark have many pharmacological functions, such as antiglaucoma, immunoregulatory, antitumor, antioxidant, antiaging, neuroprotective, and blood sugar level reducing activities [3,4,5,6,7,8,9,10].
Traditionally, the berry and root bark available have been used as medicinal sources, as well as important components in some traditional Chinese patent medicines. They are not only famous medical herbs, but are also functional foods widely consumed in health-preserving cuisines, i.e., soups, congee, herbal tea, etc. People also eat the fresh leaves as vegetables. In particular, goji berries have become increasingly popular for improving overall well-being and as an anti-aging remedy. There are many goji derived-products on health food market, such as dried fruits, juice, goji wine and goji yoghurt. Many research papers were published focused on the phytochemical fingerprinting and antioxidant activity of these products [11,12,13,14].
Two valuable medicinal herbs, namely L. barbarum and L. chinense, have received remarkable attention due to their effective clinical therapy, especially in the anti-aging category. In addition, there are increasing numbers of publications about several other Lycium plants, i.e., Lycium ruthenicum [15,16]. Many researchers have focused great attention on the Lycium genus in recent years, and many chemical components from this genus have been isolated. Therefore, a comprehensive and systematic review on the chemical constituents of the Lycium genus is much needed.
Most of the published reviews not only covered chemical composition, but also summarized the pharmacology, clinical studies, safety, toxicology and adverse actions of L. barbarum or L. chinense [17,18,19]. The aim of this review was to focus on chemical constituents in different parts of plants from different species in Lycium genus, especially small molecular compounds with updated research reports. This paper comprehensively summarizes the reports of constituents from the genus Lycium. Up to 2016, at least 355 constituents were reported from different species in the Lycium genus and different parts (fruits, root bark, leaves, seeds, and flowers) of the plant. This review describes the advances in the phytochemistry of the genus Lycium from 1975 to 2016, based on the 142 cited references. The reported constituents can be classified as glycerogalactolipids, phenylpropanoids, coumarins, lignans, flavonoids, amides, alkaloids, anthraquinones, organic acids, terpenoids, sterols, steroids, peptides, and other constituents. The aim of this review is to illustrate the recent advances in the characterization of the Lycium genus. The results, based on these phytochemical studies, could lay a solid foundation for better understanding of pharmacological activities of Lycium and quality assessment.

2. Constituents

Until now, other than polysaccharides, more than 355 compounds have been isolated and identified from the Lycium genus. The small molecules can be assigned to various classes of glycerogalactolipids, phenylpropanoids, coumarins, lignans, flavonoids, amides, alkaloids, anthraquinones, organic acids, terpenoids, sterols, steroids and their derivatives, and peptides. Beyond that, other groups of compounds have also been reported. The proportion of different compounds of the Lycium genus is show in Figure 1. Their structures are shown below, and their names and corresponding plant sources are included in this paper.

2.1. Macromolecules in the Lycium Genus

Polysaccharides

Polysaccharides are the most important group of substances in the goji berry, which are estimated to comprise 5–8% of the dried fruits [20], 1.02–2.48% of the raw material [21,22,23]. More than 40 polysaccharides, with a molecular weight range of 8–241 kDa, were isolated from the fruit of L. barbarum, L. chinense and L. ruthenicum. Two, LRLP4-A and LBLP5-A, were isolated from the leaves of L. ruthenicum. The polysaccharides share a glycan-O-Ser glycopeptide structure and contain galacturonic acid, 18 amino acids, and nine monosaccharides, namely, xylose (Xyl), glucose (Glc), arabinose (Ara), rhamnose (Rha), mannose (Man), galactose (Gal), fucose (Fuc), galacturonic acid (GalA), glucuronic acid (GlcA) [24]. The molar ratios of the polysaccharides are shown in Table 1. The polysaccharides can be isolated and purified by water extract alcohol precipitation, DEAE ion-exchange cellulose, gel-permeation chromatography, high performance liquid chromatography (HPLC). Sevage method and organic reagents were used to remove proteins, pigments and other impurities. The structural composition of a LBP can be studied by SDS-PAGE gel electrophoresis, high perfomance size exclusion chromatography (HPSEC), gas-chromatographic–mass-spectrometry (GC-MS), nucleic magnetic resonance (NMR), and matrix-assisted laser desorption ionization-time of flight-mass spectrometry (MALDI-Tof-MS) [18,21,25].

2.2. Small Molecule Substances

2.2.1. Glycerogalactolipids 1–22

At present, 17 compounds of this type, a series of glycerogalactolipids 1–17, listed in Table 2, have been isolated and identified. Compounds 1–15 have been isolated and identified from the fruits of L. barbarum [52], whereas 16 and 17 were isolated from the fruits of L. chinense [53]. Compounds 18–22, illustrated in Figure 2, were isolated from the root bark of L. chinense [54,55].

2.2.2. Phenylpropanoids 23–51

Four phenylpropanoids 23–26, namely E-cinnamic acid (23), E-ferulic acid (24), E-coniferol (25) and isoscopoletin (26) are obtained from wolfberries [56,57,58]. Four phenylpropanoids, namely scopolin (27), fabiatrin (28), lyciumin (29), and 9-O-(β-d-glucopyranosyl)lyoniresinol (30) are obtained from the root bark of L. chinense [59,60,61]. 1-O-Methyl-4-O-p-E-coumaroyl-α-l-rhamnopyranoside (31) is obtained from the fruits of L. ruthenicum [62]. The chemical structures of compounds 23–33 are listed in Table 3 and Figure 3. In 2016, 11 phenylpropanoids 32–42 were isolated for the first time by Zhou et al. from Lycium [56], including 1-O-E-feruloyl-6-O-β-d-xylopyranosyl-β-d-glucopyranoside (32), 6-O-E-feruloyl-2-O-β-d-glucopyranosyl-α-d-glucopyranoside (33), 1-O-E-feruloyl-β-d-glucopyranoside (34), ethyl-4-O-β-d-glucopyranosyl-E-ferulate (35), ethyl E-ferulate (36), E-sinapinic acid (37), syringenin (38), Z-ferulic acid (39), phloretic acid (40), dihydroferulic acid (41), and ethyl dihydroferulate (42), along with the nine new lycibarbarphenylpropanoids A–I (compounds 43–51) listed in Table 4.

2.2.3. Coumarins 52–61

Nine coumarins, namely E-p-coumaric acid (52), Z-p-coumaric acid (53), esculetin (54), fabiatrin (55), scopolin (56), and scopoletin (57), have been reported, and three new coumarins, 6-O-E-p-coumaroyl-2-O-β-d-glucopyranosyl-α-d-glucopyranoside (58), ethyl-4-O-β-d-glucopyranosyl-E-p-coumarate (59), ethyl E-p-coumarate (60) and lycibarbarcoumarin A (61), have been obtained from the fruits of L. barbarum in 2016 [56]. Compounds 55 and 56 were isolated from the root bark and fruits of L. chinense [61], while 52−54 and 57 were isolated from the fruits of L. barbarum [63]. The chemical structures of these coumarins are listed in Figure 4 and Table 5.

2.2.4. Lignans 62–74

Eight lignans, including pinoresinol (62), arctigenin (63), arctiin (64), medioresinol (65), syringaresinol (66), 4-O-(β-d-glucopyranosyl)syringaresinol (67), threo-1,2-bis(4-hydroxy-3-methoxy-phenyl)-1,3-propanediol (68), and erythro-1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (69), have been isolated from the fruits of L. barbarum [56]. (β)-Lyoniresinol 3-O-β-d-glucopyranoside (70), lyciumlignan A (71), lyciumlignan B (72), lyciumlignan C (73), and (7R,8S)-4,9,9′-trihydroxy-3,3′-dimethoxy-7′-en-8,4′-oxyneolignan-7-O-β-d-glucopyranoside (74) were obtained from the root bark of L. chinense [54,60,64]. Among them, 65–70 were first isolated from the fruits of L. barbarum in 2016 [56]. The chemical structures of these lignans are listed in Figure 5 and Table 6.

2.2.5. Flavonoids 75–106

Twenty-seven flavonoids 75–101 have been reported from the genus Lycium, are listed in Table 7 and Table 8 and Figure 6 and Figure 7. Compound 75 was isolated from the flowers of L. barbarum [58], while 76–83 were identified from the fruits of L. barbarum [62,65,66,67,68,69]. Compound 84 was isolated from the fruits of L. chinense [70], whereas 85–91 were isolated from the leaves of L. chinense [62,66,68,71]. Compound 92 and 93 were isolated from the leaves of L. halimifolium [72]. Compounds 94–98 were isolated from the fruits of L. ruthenicum [16,62]. Compounds 99–101 were isolated from the root bark of L. chinense [54,73,74]. Additionally, Zhou et al. isolated five isoflavonoids, namely derrone (102), alpinumisoflavone (103), auriculasin (104), maackianin (105) and maackiain (106) from the fruits of L. barbarum [56,75,76].

2.2.6. Amides 107–143

Sixteen amides 107–122 have been isolated from the root bark of L. chinense [9,54,60,77,78,79,80], 19 amides (123–141) have been isolated from the fruits of L. barbarum [81,82,83,84,85,86,87,88]. Meanwhile, two cerebrosides 142 and 143 have been obtained from fruits of L. chinense [89]. The chemical structures of these amides are shown in Figure 8.

2.2.7. Alkaloids 144–215

To date, 72 alkaloids have been identified, which can be classified into five categories: nortropane, imidazole, piperidine, pyrrole, spermine, tropane, and other alkaloids.

Nortropane Alkaloids

Fourteen nortropane alkaloids 144–157, shiwn in Figure 9, have been isolated from the root bark of L. chinense [90].

Imidazole Alkaloids

Six imidazole alkaloids 158–162 were detected in the leaves of L. cestroides [91]: Meanwhile, one imidazole, Na-[(E)-cinnamoyl]histamine (163), was obtained from the leaves of L. barbarum [66], listed in Figure 10.

Piperidine Alkaloids

5-hydroxy-2-pyridylmethyl ketone (164), methyl 5-hydroxy-2-pyridinecarboxylate (165), fagomine (166), and 6-deoxyfagomine (167), listed in Figure 11, have been isolated and identified from the genus Lycium; among them. Compounds 164 and 165 are from the fruits of L. barbarum [92], and 166 and 167 are from the root bark of L. chinense [90].

Pyrrole Alkaloids

Thirteen pyrrole alkaloids 168–180 have been isolated from the fruits of L. chinense [93,94,95]. Likewise, 2-formyl-5-hydroxymethylpyrrole (181) and 2-formyl-5-methoxymethylpyrrole (182) were isolated from the fruits of L. barbarum [92]. Two pyrrolidine alkaloids, alkaloid I (183) and alkaloid II (184), are obtained from the root bark of L. chinense [96]. The chemical structures of these pyrrole alkaloids are listed in Figure 12.

Spermine Alkaloids

Nineteen spermine alkaloids have been found in the genus Lycium. Kukoamines A (185) and kukoamines B (186) are from the root bark of L. chinense [97,98], while N1-caffeoyl-N3-dihydrocaffeoyl spermidine (187) and lyrium spermidine A (188) are from the fruits of L. ruthenicum [62,99], listed in Figure 13. Another 15 spermine alkaloids, lycibarbarspermidine A–O (189–203), listed in Table 9 and Table 10 and Figure 13, Figure 14 and Figure 15, are from L. barbarum [100].

Tropane Alkaloids

As we know, the genus Lycium has been used as both a medicine and a food for a long time in Asia, particularly in China. However, the safety of Lycium has been questioned for some time, especially after the detection of the three tropane alkaloids atropine (204), hyoscyamine (205), and scopolamine (206) [101]. Atropine and hyoscyamine were identified from the fruits of L. barbarum gathered in India, while scopolamine was identified from L. halimifolium at concentrations higher than the toxic dose. However, another scholar, seeking to verify these reports, demonstrated that the atropine content of L. barbarum from different sources was just 3.0 ppb—far below the poisoning dose [102]. It was demonstrated that none of the toxic compounds were detected in fruits, leaves, stems and roots of three L. barbarum varieties (‘No. 1’, ‘New Big’ and ‘Amber Sweet Goji’) by densitometric TLC analysis [103]. Through field investigation and model specimen inspections, the above three tropane alkaloids were determined to be from Lycium europaeum rather than the L. barbarum. Thus, the genus Lycium is likely non-toxic, and consumers can rest assured that its use is safe [104].
Other than the alkaloids that have been already mentioned, there are nine others that have been obtained from this genus, including 9-formylharman (207), 1-(methoxycarbonyl)-β-carboline (208), perlolyrine (209), choline (210), 1β-amino-3β,4β,5α-trihydroxycycloheptane (211), betaine hydrochloride (212), nicotianamine (213), betaine (214), and melatonin (215). Compounds 207–209 were isolated from the fruits of L. chinense [105], while 210–212 were isolated from the root bark of L. chinense [90]. Compound 213 was isolated from the leaves and flowers of L. chinense [106], and 214 and 215 were isolated from the fruits of L. barbarum [107,108]. The chemical structures of these tropane alkaloids are listed in Figure 16.

2.2.8. Anthraquinones 216–219

Four anthraquinones: emodin (216), physcion (217), 6-hydroxyrubiadin (218), and 3-O-(2-O-α-l-rhamnopyranosyl-6-O-acetyl-β-d-glucopyranosyl)-6-hydroxy-rubiadin (219), listed in Figure 17, have been obtained from the root bark of L. chinense [61,109].

2.2.9. Organic Acids 220–251

To this point, 32 organic acids, listed in Figure 18, have been identified from the genus Lycium, which can be classified into two groups: aliphatic acids 220–238 and aromatic acids and their derivatives 239–251. Compounds 220–225 and 240–244 were isolated from the fruits of L. barbarum [56,63,65,107,110,111,112]; 239 and 245 were isolated from the leaves of L. barbarum [66]; 226 was isolated from the root of L. chinense [113]; 227, 248 and 249 were isolated from the fruits of L. chinense [70,114]; 228–233 and 248 were isolated from the leaves of L. chinense [115]; 234, 235, and 249–251 were isolated from the root bark of L. chinense [53,78,93,116,117], and 236–238 were isolated from the fruits of L. urcomanicum [118,119].

2.2.10. Terpenoids 252–290

Thirty-seven terpenoids, listed in Figure 19, Figure 20 and Figure 21 and Table 11 and Table 12, have been found in the genus Lycium, mainly including monoterpenes 252–256, sesquiterpenes 257–263, diterpenoids 264–274, and carotenoids 275–290. Among them, carotenoids are one of the more important constituents of the Lycium fruits. Thus compounds 256 and 275–286 were isolated from the fruits of L. barbarum [120,121,122,123]; 253, 254, 258, 259 and 287–290 were isolated from the fruits of L. chinense [120,121,124,125,126]; 252 and 264–272 were isolated from the leaves of L. chinense [127,128]; 255, 258 and 273–274 were isolated from the root bark of L. chinense [80,116]; 260 and 261 were isolated from the leaves of L. halimifolium [23]; and 262 and 265 were isolated from the leaves of L. barbarum [129].

2.2.11. Sterols, Steroids, and Their Derivatives 291–347

Fifty-seven sterols, steroids, and their derivatives 291–347, listed in Figure 22, have been identified from the genus Lycium, mainly from the seeds and the fruits. Compounds 293 and 343 were identified from the flowers of L. barbarum [130], 291–292; 295, 298, 319–324 and 337–339 were identified from the fruits of L. chinense [23,35,52,63,107,131]; 341 342, 346 and 347 were identified from the leaves of L. chinense [132,133]; 336 and 340 were identified from the root bark of L. chinense [80,121]; 294 was identified from the seed of L. ciliatum [66]; all others were identified from the seed of L. chinense [134,135,136,137] 344 and 345 were identified from the seeds of L. barbarum [138].

2.2.12. Peptides 348–352

Five peptides have been isolated from the root bark of L. chinense [80,139], including one dipeptide, lyciumamide (348), and four octapeptides, called lyciumins A–D (compounds 349–350), illustrated in Figure 23.

2.2.13. Other Compounds 353–355

Other than what has already been mentioned, a few other chemical constituents, listed in Figure 24, were also isolated from the genus Lycium. Digupigan A (353), 2-O-(β-d-glucopyranosyl)ascorbic acid (354) and p-hydroxybenzaldehyde (355) also have been obtained from the root bark of L. chinense, the fruits of L. chinense, and the fruits of L. barbarum [75,76,121,137,140,141], respectively. Many minerals, amino acids, and proteins have also been found in the genus Lycium, such as Ca, Mg, Zn, Fe, aminoethanesulfonic acid, γ-aminobutyric acid (GABA), Mn-SOD, etc. [121,142,143].

3. Discussion

Lycium species are of valuable medicinal, nutritional and functional significance, and have been studied in terms of their chemical compounds. Phytochemical investigations on eight different species, have resulted in the isolation of at least 355 constituents up to July of 2016. Research on chemical compounds has concentrated mainly on L. barbarum and L. chinense. Therefore, future phytochemistry research should be focused on the other species in Lycium genus. In addition, diverse plant parts (i.e., the flowers, leaves, seeds) have also been testified to contain new constituents, most of which possess the novel chemical structures. Polysaccharides play a particularly significant role in exerting pharmacological actions. A specific class of polysaccharides, abbreviated as LBP, is used as biomarker in the 2015 Chinese Pharmacopoeia as a measure by which wolfberry is qualified. At present, LBP in products or in pharmacological studies usually are polysaccharide mixtures with heterogeneity and polydispersity. On the other hand, development of new separation, detection techniques will greatly benefit the phytochemical isolation and structural elucidation of LBP. There is a growing recognition that not only the LBP, but also the plant secondary metabolites may have the potential active ingredients, while most of the research on goji berry was LBP rather than small molecule substances, so more intensive studies of goji berry are required to shed some light on these compounds.

Acknowledgments

This research was financially supported by The National Science Fund for Distinguished Young Scholars of China (81325023).

Author Contributions

D.Q. and L.H. conceived and designed the paper; D.Q. wrote the paper and L.H. reviewed the paper. Y.Z. and G.Y. discussed the results and commented on the manuscript. All authors read and approved the final manuscript.

Conflicts of Interest

The authors declare no conflict of interest.

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Molecules 22 00911 g001 550
Figure 1. Different subtype comparison of the 355 constituents reported from Lycium genus.
Figure 1. Different subtype comparison of the 355 constituents reported from Lycium genus.
Molecules 22 00911 g001
Molecules 22 00911 g002 550
Figure 2. Chemical structures of compounds 18–22.
Figure 2. Chemical structures of compounds 18–22.
Molecules 22 00911 g002
Molecules 22 00911 g003 550
Figure 3. Chemical structures of compounds 23–25, 29–31.
Figure 3. Chemical structures of compounds 23–25, 29–31.
Molecules 22 00911 g003
Molecules 22 00911 g004 550
Figure 4. Chemical structures of compounds 52–57, 61.
Figure 4. Chemical structures of compounds 52–57, 61.
Molecules 22 00911 g004
Molecules 22 00911 g005 550
Figure 5. Chemical structures of compounds 63–64 and 68–74.
Figure 5. Chemical structures of compounds 63–64 and 68–74.
Molecules 22 00911 g005
Molecules 22 00911 g006 550
Figure 6. Chemical structures of compounds 81, 84, 88 and 94.
Figure 6. Chemical structures of compounds 81, 84, 88 and 94.
Molecules 22 00911 g006
Molecules 22 00911 g007 550
Figure 7. Chemical structures of compounds 99–106.
Figure 7. Chemical structures of compounds 99–106.
Molecules 22 00911 g007
Molecules 22 00911 g008a 550Molecules 22 00911 g008b 550Molecules 22 00911 g008c 550Molecules 22 00911 g008d 550
Figure 8. Chemical structures of compounds 107–143.
Figure 8. Chemical structures of compounds 107–143.
Molecules 22 00911 g008aMolecules 22 00911 g008bMolecules 22 00911 g008cMolecules 22 00911 g008d
Molecules 22 00911 g009a 550Molecules 22 00911 g009b 550
Figure 9. Chemical structures of compounds 144–157.
Figure 9. Chemical structures of compounds 144–157.
Molecules 22 00911 g009aMolecules 22 00911 g009b
Molecules 22 00911 g010 550
Figure 10. Chemical structures of compounds 158–163.
Figure 10. Chemical structures of compounds 158–163.
Molecules 22 00911 g010
Molecules 22 00911 g011 550
Figure 11. Chemical structures of compounds 164–167.
Figure 11. Chemical structures of compounds 164–167.
Molecules 22 00911 g011
Molecules 22 00911 g012 550
Figure 12. Chemical structures of compounds 168–184.
Figure 12. Chemical structures of compounds 168–184.
Molecules 22 00911 g012
Molecules 22 00911 g013 550
Figure 13. Chemical structures of compounds 185–188.
Figure 13. Chemical structures of compounds 185–188.
Molecules 22 00911 g013
Molecules 22 00911 g014 550
Figure 14. Chemical structures of compounds 194 and 195.
Figure 14. Chemical structures of compounds 194 and 195.
Molecules 22 00911 g014
Molecules 22 00911 g015 550
Figure 15. Chemical structures of compounds 201–203.
Figure 15. Chemical structures of compounds 201–203.
Molecules 22 00911 g015
Molecules 22 00911 g016a 550Molecules 22 00911 g016b 550
Figure 16. Chemical structures of compounds 204–215.
Figure 16. Chemical structures of compounds 204–215.
Molecules 22 00911 g016aMolecules 22 00911 g016b
Molecules 22 00911 g017 550
Figure 17. Chemical structures of compounds 216–219.
Figure 17. Chemical structures of compounds 216–219.
Molecules 22 00911 g017
Molecules 22 00911 g018a 550Molecules 22 00911 g018b 550
Figure 18. Chemical structures of compounds 220–251.
Figure 18. Chemical structures of compounds 220–251.
Molecules 22 00911 g018aMolecules 22 00911 g018b
Molecules 22 00911 g019 550
Figure 19. Chemical structures of compounds 252–263, 266.
Figure 19. Chemical structures of compounds 252–263, 266.
Molecules 22 00911 g019
Molecules 22 00911 g020 550
Figure 20. Chemical structures of compounds 271 and 274.
Figure 20. Chemical structures of compounds 271 and 274.
Molecules 22 00911 g020
Molecules 22 00911 g021a 550Molecules 22 00911 g021b 550
Figure 21. Chemical structures of compounds 283–290.
Figure 21. Chemical structures of compounds 283–290.
Molecules 22 00911 g021aMolecules 22 00911 g021b
Molecules 22 00911 g022a 550Molecules 22 00911 g022b 550Molecules 22 00911 g022c 550Molecules 22 00911 g022d 550
Figure 22. Chemical structures of compounds 291–347.
Figure 22. Chemical structures of compounds 291–347.
Molecules 22 00911 g022aMolecules 22 00911 g022bMolecules 22 00911 g022cMolecules 22 00911 g022d
Molecules 22 00911 g023 550
Figure 23. Chemical structures of compounds 348–352.
Figure 23. Chemical structures of compounds 348–352.
Molecules 22 00911 g023
Molecules 22 00911 g024 550
Figure 24. Chemical structures of compounds 353–355.
Figure 24. Chemical structures of compounds 353–355.
Molecules 22 00911 g024
Table
Table 1. The molar ratios and source of LBPs.
Table 1. The molar ratios and source of LBPs.
LBPsMolar RatioSourceReference
LbGp1Ara:Gal:Glc = 2.5:1.0:1.0L. barbarum[26]
LbGp2Ara:Gal = 4:5L. barbarum[27]
LbGp3Ara:Gal = 1:1L. barbarum[28,29]
LbGp4Ara:Gal:Rha:Glc = 1.5:2.5:0.43:0.23 L. barbarum[28,30]
LbGp5Rha:Ara:Xyl:Gal:Man:Glc = 0.33:0.52:0.42:0.94:0.85:1L. barbarum[28]
LbGp5BRha:Ara:Glc:Gal = 0.1:1:1.2:0.3 L. barbarum[31]
LBP3p Rha:Ara:Xyl:Gal:Man:Glc = 1.25:1.10:1.76:1:1.95:2.12L. barbarum[32]
LBPC2Xyl:Rha:Man = 8.8:2.3:1L. barbarum[33]
LBPC4GlcL. barbarum[33]
LBPA1heteroglycanL. barbarum[33]
LBPA3heteroglycanL. barbarum[33]
LBP1a-1GlcL. barbarum[34]
LBP1a-2GlcL. barbarum[34]
LBP3a-1GalAL. barbarum[34]
LBP3a-2GalAL. barbarum[34]
LBPF1-L. barbarum[35]
LBPF2-L. barbarum[35]
LBPF3-L. barbarum[35]
LBPF4-L. barbarum[35]
LBPF5Ara, Man, Xyl, Glu, RhaL. barbarum[35,36]
LBPF6-L. barbarum[36]
LPBC4GlcL. barbarum[37]
LBP-1Rha:Ara:Xyl:Gal:Man:GalA = 1:7.85:0.37:0.65:3.01:8.16L. barbarum[22]
WSP1Rha:Fuc:Ara:Xyl:Man:Gal:Glc = 1.6:0.2:51.4:4.8:1.2:25.9:7.3L. barbarum[23]
AGPRha:Ara:Xyl:Gal:Glc:GalA:GlcA = 3.3:42.9:0.3:44.3:2.4:7.0L. barbarum[38]
LBP-IVRha:Ara:Xyl:Glc:Gal = 1.61:3.82:3.44:7.54:1.00L. barbarum[39]
LbGp1Ara:Gal = 5.6:1L. barbarum[40]
LBP-s-1Rha:Ara:Xyl:Man:Glu:Gal:Gal A = 1.00:8.34:1.25:1.26:1.91:7.05:15.28L. barbarum[41]
p-LBPFuc:Rha:Ara:Gal:Glc:Xyl:Gal A:Glc A = 1.00:6.44:54.84:22.98:4.05:2.95:136.98:3.35L. barbarum[42]
Cp-2-AAra:Gal:Man:Rha:Glu = 6.02:2.71:1.00:0.70:0.67L. chinese[43,44]
Cp-2-BAra:Gal = 1:0.96L. chinese[43,44]
Hp-2-AAra:Gal = 5.2:1L. chinese[43,44]
Hp-2-BAra:Gal = 7.9:1L. chinese[43,44]
Hp-2-CAra:Gal = 1.2:1L. chinese[43,44]
Hp-0-A Ara:Gal = 14:1L. chinese[43,44]
Cp-1-AAra:Xyl = 1:1L. chinese[45]
Cp-1-BAraL. chinese[45]
Cp-1-CAra:Gal = 3:1L. chinese[45]
Cp-1-DAra:Gal = 1:1L. chinese[45]
LRGP1Rha:Ara:Xyl:Man:Glu:Gal = 0.65:10.71:0.33:0.67:1:10.41L. ruthenicum[46]
LRGP2-L. ruthenicum[47]
LRGP3Rha:Ara:Gal = 1.0:14.9:10.4L. ruthenicum[48]
LRGP4-ARha:Ara:Glu:Gal = 1:7.6:0.5:8.6L. ruthenicum[49]
LRGP5Rha:Ara:Xyl:Gal:GalA = 1.0:2.2:0.5:1.2:4.7L. ruthenicum[50]
LRLP4-ARha:Ara:Gal = 1:10.3:5.3L. ruthenicum[47]
LBLP5-A-L. ruthenicum[51]
Table
Table 2. Chemical structures of compounds 1–17.
Table 2. Chemical structures of compounds 1–17.
Molecules 22 00911 i001 Molecules 22 00911 i002
No.CompoundsR1R2R3Source
1Glycerogalactolipids APalmitoylLinolenoylLinolenoylL. barbarum
2Glycerogalactolipids BPalmitoylLinolenoylLinoleoylL. barbarum
3Glycerogalactolipids CPalmitoylLinolenoylPalmitoylL. barbarum
4Glycerogalactolipids DPalmitoylLinoleoylPalmitoylL. barbarum
5Glycerogalactolipids EPalmitoylPalmitoylPalmitoylL. barbarum
6Glycerogalactolipids FPalmitoylPalmitoylHL. barbarum
7Glycerogalactolipids GLinolenoylLinolenoylHL. barbarum
8Glycerogalactolipids HLinolenoylLinoleoylHL. barbarum
9Glycerogalactolipids IPalmitoylLinolenoylHL. barbarum
10Glycerogalactolipids JPalmitoylLinoleoylHL. barbarum
11Glycerogalactolipids KPalmitoylOleoylHL. barbarum
12Glycerogalactolipids LStearoylLinoleoylHL. barbarum
13Glycerogalactolipids MPalmitoylLinolenoyl–L. barbarum
14Glycerogalactolipids NPalmitoylLinoleoyl–L. barbarum
15Glycerogalactolipids OPalmitoylOleoyl–L. barbarum
16Glycerogalactolipids PLinolenoylLinolenoyl–L. chinense
17Glycerogalactolipids QLinoleoylLinolenoyl–L. chinense
Table
Table 3. Chemical structures of compounds 26–28.
Table 3. Chemical structures of compounds 26–28.
Molecules 22 00911 i003
No.CompoundsR1(R)R2Source
26IsoscopoletinOCH3OHL. barbarum
27ScopolinO-β-d-GlcOCH3L. chinense
28FabiatrinO-β-d-Glc6-β-d-XylOCH3L. chinense
Table
Table 4. Chemical structures of compounds 32–51.
Table 4. Chemical structures of compounds 32–51.
Molecules 22 00911 i004 Molecules 22 00911 i005
No.CompoundsR1R2R3R4Source
321-O-E-feruloyl-6-O-β-d-xylopyranosyl-β-d-glucopyranosideOCH3OHHCOO-β-d-Glc6-β-d-XylL. barbarum
336-O-E-feruloyl-2-O-β-d-glucopyranosyl-α-d-glucopyranosideOCH3OHHCOO6-α-d-Glc2-β-d-GlcL. barbarum
341-O-E-feruloyl-β-d-glucopyranosideOCH3OHHCOO-β-d-GlcL. barbarum
35Ethyl-4-O-β-d-glucopyranosyl-E-ferulateOCH3O-β-d-GlcHCOOCH2CH3L. barbarum
36Ethyl E-ferulateOCH3OHHCOOCH2CH3L. barbarum
37E-sinapinic acidOCH3OHOCH3COOHL. barbarum
38SyringeninOCH3OHOCH3CH2OHL. barbarum
39E-ferulic acidOCH3OHHCOOHL. barbarum
40Phloretic acidHOHHCOOHL. barbarum
41Dihydroferulic acidOCH3OHHCOOHL. barbarum
42Ethyl dihydroferulateOCH3OHHCOOCH2CH3L. barbarum
43Lycibarbarphenylpropanoids A HOHHCOO-β-d-Glc3-β-d-GlcL. barbarum
44Lycibarbarphenylpropanoids BHOHHCOO-β-d-Glc4-β-d-GlcL. barbarum
45Lycibarbarphenylpropanoids COCH3OHHCOO-β-d-Glc3-β-d-GlcL. barbarum
46Lycibarbarphenylpropanoids DOCH3OHHCOO-β-d-Glc4-β-d-GlcL. barbarum
47Lycibarbarphenylpropanoids EOCH3OHHCH2O-β-d-Glc3-β-d-GlcL. barbarum
48Lycibarbarphenylpropanoids FHO-β-d-Glc3-β-d-GlcHCOOCH2CH3L. barbarum
49Lycibarbarphenylpropanoids GHO-β-d-Glc4-β-d-GlcHCOOCH2CH3L. barbarum
50Lycibarbarphenylpropanoids HOCH3O-β-d-Glc4-β-d-GlcHCOOCH2CH3L. barbarum
51Lycibarbarphenylpropanoids IO-β-d-GlcOHHCOOCH2CH3L. barbarum
Table
Table 5. Chemical structures of compounds 58–60.
Table 5. Chemical structures of compounds 58–60.
Molecules 22 00911 i006
No.CompoundsR1R2R3R4Source
586-O-E-p-coumaroyl-2-O-β-d-glucopyranosyl-α-d-glucopyranosideHOHHCOO6-α-d-Glc2-β-d-GlcL. barbarum
59Ethyl-4-O-β-d-glucopyranosyl-E-p-coumarateHO-β-d-GlcHCOOCH2CH3L. barbarum
60Ethyl E-p-coumarateHOHHCOOCH2CH3L. barbarum
Table
Table 6. Chemical structures of compounds 62 and 65–67.
Table 6. Chemical structures of compounds 62 and 65–67.
Molecules 22 00911 i007
No.CompoundsR1R2R3Source
62PinoresinolHOHHL. barbarum
65MedioresinolHOHOCH3L. barbarum
66SyringaresinolOCH3OHOCH3L. barbarum
674-O-(β-d-glucopyranosyl)syringaresinolOCH3O-β-d-GlcOCH3L. barbarum
Table
Table 7. Chemical structures of compounds 75–80, 82–83, 85–87 and 89–93.
Table 7. Chemical structures of compounds 75–80, 82–83, 85–87 and 89–93.
Molecules 22 00911 i008 Molecules 22 00911 i009 Molecules 22 00911 i010
No.CompoundsR1R2R3Source
75QuercitrinOHOHO-α-l-RhaL. barbarum
76KaempferolOHOH–L. barbarum
77QuercetinOHOHOHL. barbarum
78RutinOHOHO-β-d-Glc6-α-l-RhaL. barbarum
79NarcissosideOHOCH3O-β-d-Glc6-α-l-RhaL. barbarum
807-O-(β-d-Glucopyranosyl)-rutinO-β-d-GlcOHO-β-d-Glc6-α-l-RhaL. barbarum
827-O-(β-d-Glucopyranosyl)-nicotiflorinO-β-d-GlcO-β-d-Glc6-α-l-Rha–L. barbarum
837-O-(β-d-Glucopyranosyl)-3-O-[β-d-glucopyranosyl]-(1 → 2)-β-d-galactopO-β-d-GlcO-β-d-Glc6-α-l-Glc–L. barbarum
85LuteolinOHOHOHL. chinense
86AcacetinOHHOCH3L. chinense
877-O-(β-d-Glucopyranosyl)-3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranosyl]-quercetinO-β-d-GlcOHO-β-d-Glc2-β-d-GlcL. chinense
897-O-[α-l-Rhamno-pyranosyl-(1 → 6)-β-d-glucopyranosyl]-acacetinO-β-d-Glc6-α-l-RhaHOCH3L. chinense
903-O-Sophoroside-quercetinOHOHO-β-d-Glc2-β-d-GlcL. chinense
91ApigeninOHHOHL. chinense
92IsoquercitrinOHOHO-β-d-GlcL. halimifolium
93NicotiflorinOHO-β-d-Glc6-α-l-Rha–L. halimifolium
Table
Table 8. Chemical structures of compounds 95–98.
Table 8. Chemical structures of compounds 95–98.
Molecules 22 00911 i011
No.CompoundsR1R2Source
955-O-(β-d-Glucopyranosyl)-3-O-[4-O-p-E-coumaroyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl]-peonidinHOHL. ruthenicum
965-O-(β-d-Glucopyranosyl)-3-O-[4-O-p-E-coumaroyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl]-petunidinOHOHL. ruthenicum
975-O-(β-d-Glucopyranosyl)-3-O-[4-O-p-Z-coumaroyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl]-malvidinOCH3OHL. ruthenicum
985-O-(β-d-Glucopyranosyl)-3-O-[4-O-p-E-(β-d-glucopyranoside)-coumaroyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl]-petunidinOHO-β-d-GlcL. ruthenicum
Table
Table 9. Chemical structures of compounds 189–193.
Table 9. Chemical structures of compounds 189–193.
Molecules 22 00911 i012
No.CompoundsR1R2R3R4Source
189Lycibarbarspermidine AHβ-d-GlcHHL. barbarum
190Lycibarbarspermidine BHHβ-d-GlcHL. barbarum
191Lycibarbarspermidine Cβ-d-Glc HHHL. barbarum
192Lycibarbarspermidine DHHHβ-d-GlcL. barbarum
193Lycibarbarspermidine EHβ-d-Glcβ-d-GlcHL. barbarum
Table
Table 10. Chemical structures of compounds 196–200.
Table 10. Chemical structures of compounds 196–200.
Molecules 22 00911 i013
No.CompoundsR1R2R3R4Source
196Lycibarbarspermidine HHHHβ-d-GlcL. barbarum
197Lycibarbarspermidine IHβ-d-GlcHHL. barbarum
198Lycibarbarspermidine JHHβ-d-GlcHL. barbarum
199Lycibarbarspermidine Kβ-d-GlcHβ-d-GlcHL. barbarum
200Lycibarbarspermidine LHβ-d-GlcHβ-d-GlcL. barbarum
Table
Table 11. Chemical structures of compounds 264–265, 267–270 and 272–273.
Table 11. Chemical structures of compounds 264–265, 267–270 and 272–273.
Molecules 22 00911 i014
No.CompoundsR1R2Source
264Lyciumosides IGlcGlcL. chinense
265Lyciumosides IIGlc2-GlcGlcL. chinense
267Lyciumosides IVGlcGlc4-RhaL. chinense
268Lyciumosides VGlc6-RhaGlcL. chinense
269Lyciumosides VIGlc6-RhaGlc4-RhaL. chinense
270Lyciumosides VIIGlc2-Rha(6-Glc)GlcL. chinense
272Lyciumosides IXGlc6-O-malonyl-GlcL. chinense
273Capsianoside IIRha3-Glc6-RhaGlc2-GlcL. chinense
Table
Table 12. Chemical structures of compounds 275–282.
Table 12. Chemical structures of compounds 275–282.
Molecules 22 00911 i015
No.CompoundsR1R2Source
275β-CaroteneHHL. barbarum
276β-CryptoxanthinOHHL. barbarum
277ZeaxanthinOHOHL. barbarum
278Zeaxanthin monopalmitateOCO(CH2)14CH3OHL. barbarum
279Zeaxanthin dipalmitateOCO(CH2)14CH3OCO(CH2)14CH3L. barbarum
280Zeaxanthin monomyristateOHOCO(CH2)12CH3L. barbarum
281Zeaxanthin dimyristateOCO(CH2)12CH3OCO(CH2)12CH3L. barbarum
282β-Cryptoxanthin palmitateOCO(CH2)14CH3HL. barbarum

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Qian, D.; Zhao, Y.; Yang, G.; Huang, L. Systematic Review of Chemical Constituents in the Genus Lycium (Solanaceae). Molecules 2017, 22, 911. https://doi.org/10.3390/molecules22060911

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Qian D, Zhao Y, Yang G, Huang L. Systematic Review of Chemical Constituents in the Genus Lycium (Solanaceae). Molecules. 2017; 22(6):911. https://doi.org/10.3390/molecules22060911

Chicago/Turabian Style

Qian, Dan, Yaxing Zhao, Guang Yang, and Luqi Huang. 2017. "Systematic Review of Chemical Constituents in the Genus Lycium (Solanaceae)" Molecules 22, no. 6: 911. https://doi.org/10.3390/molecules22060911

APA Style

Qian, D., Zhao, Y., Yang, G., & Huang, L. (2017). Systematic Review of Chemical Constituents in the Genus Lycium (Solanaceae). Molecules, 22(6), 911. https://doi.org/10.3390/molecules22060911

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