IJCMInternational Journal of Clinical Medicine2158-284XScientific Research Publishing10.4236/ijcm.2021.1211045IJCM-113554ArticlesMedicine&Healthcare A Systematic Review on Chemical Constituents of Suanzaoren Decoction, a Traditional Chinese Medicine Prescription WenchaoGu1*TianyuanYe1LiangkunZhang1YongYang1DongmeiQi1XiaoruiCheng1XinWang1Shandong University of Traditional Chinese Medicine, Jinan, China09112021121149452311, October 202127, November 2021 30, November 2021© Copyright 2014 by authors and Scientific Research Publishing Inc. 2014This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/

Traditional Chinese Medicine prescription Suanzaoren decoction (SZRD) is composed of Ziziphi Spinosae Semen, Chuanxiong Rhizoma, Anemarrhenae rhizoma, Poria and Licorice. It was used to treat central nervous system diseases such as insomnia and anxiety for thousands of years. This paper aims to systematically understand varieties and quantities of compounds and clarify chemical components of SZRD, subsequently to further provide the reference for phytochemistry and pharmacology researches of SZRD. Our results showed that SZRD contained 145 components, including flavonoids, triterpenoids, steroids, coumarins, phthalides, and volatile oils, etc., while five-single herbs contain 1104 components. Only in terms of compound number, there were 80 common components in SZRD and its five herbs, which accounted for 6.8% of total compounds in all 5 herbs and 55.2% of compounds in SZRD. The components of SZRD were not simply the sum of one in every single herb. It is necessary to perform parallel studies among SZRD and its herbs. This review discussed the problems that existed in the chemical research of SZRD and pointed out the direction for its further research.

Traditional Chinese Medicine Suanzaoren Decoction Chemical Ingredient1. Introduction

Suanzaoren decoction (SZRD), a classic Traditional Chinese Medicine (TCM) prescription, was first described in the book “Jin Gui Yao Lue” by Zhongjing Zhang in Han dynasty. SZRD is consists of five herbs, Suanzaoren (Ziziphi Spinosae Semen, Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H.F. Chou), Chuanxiong (Chuanxiong Rhizoma, Ligusticum chuanxiong Hort.), Zhimu (Anemarrhenae rhizoma, Anemarrhena asphodeloides Bge.), Fuling (Poria, Poria cocos (Schw.) Wolf) and Gancao (Licorice, Glycyrrhiza uralensis Fisch., Glycyrrhiza inflata Bat. or Glycyrrhiza glabra L.) at a ratio of 15:6:6:6:3. In the clinic of TCM, SZRD is the most common herbal formula prescribed by TCM doctors to treat central nervous system diseases such as insomnia [1] [2] [3], secondary insomnia [4] [5] [6] [7], anxiety [8], depression [9], menopausal syndrome [10] and other diseases [11] [12]. Clinical researches showed that the combination of SZRD and other drugs, including TCM and chemicals, can improve insomnia [13] [14] [15] [16], anxiety [16] [17] [18], depression [19] [20] and other diseases [21], enhance the efficiency of treatment, and reduce adverse reactions. Besides, SZRD has pharmacological characteristics of immune protective and sedative effects [22].

The clinical therapeutic effect and pharmacological function of SZRD originate in its chemical composition. A vast lot of chemical components in SZRD have been isolated and identified using high-performance liquid chromatography (HPLC) and mass spectrometry (MS) technology. In this paper, we investigated and analyzed chemical ingredients of SZRD and its five-single herbs on basis of literatures in the last 5 years and calculated the percentage based on compounds number of a certain class in the total number of compounds. We also focused on similarities and differences of ingredients between SZRD and its herbs.

2. Chemical Constituents of Five Herbs in Suanzaoren Decoction2.1. Suanzaoren (Ziziphi Spinosae Semen, Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H.F. Chou)

We used “Suanzaoren”, “Zaoren”, “Ziziphi Spinosae Semen”, “Jujube”, “Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou” as key words to search chemical components of Ziziphi Spinosae Semen. We mainly focused on the literatures of the past five years, and tried to get more ingredients at the same time. Results showed mounts of literatures on ingredients of Ziziphi Spinosae Semen have been reported until now. The 36 chemical components in standard decoction of Ziziphi Spinosae Semen are isolated by using UPLC-Q/TOF-MS and UPLC-PDA system, including nucleosides, phenolic acids, alkaloids and flavonoids [23]. The 109 components are identified in Ziziphi Spinosae Semen by UPLC-Q/TOF-MS and principal component analysis (PCA), including 66 flavonoids, 15 triterpenoid saponin, 19 alkaloids, 8 terpenoid acids and 1 phenolic acid [24]. Research on components in crude and parched Ziziphi Spinosae Semen shows that 40 chemical ingredients (flavonoids, saponins, alkaloids and triterpenoids, etc.) are changed during stir-frying process and 19 key markers can contribute to classification of crude and parched Ziziphi Spinosae Semen [25]. The sedative and hypnotic effects of Ziziphi Spinosae Semen were significantly enhanced after processing. These researches provided a rapid and effective approach to monitor quality consistency of Ziziphi Spinosae Semen.

We totally collected 175 compounds in Ziziphi Spinosae Semen [23] - [40], which were divided into 8 categories, including flavonoids (62 compounds), alkaloids (28 compounds), amino acids (6 compounds), nucleosides (4 compounds), phenolic acids (4 compounds), triterpenoids (61 compounds), volatile oils (9 compounds) and others (1 compound) (Table 1). Ziziphi Spinosae Semen has the highest proportion of flavonoids (36%), followed by triterpenes (35%), and the lowest proportion of phenolic acids (2%) and nucleotides (2%) (Figure 1(a)).

2.2. Chuanxiong (Chuanxiong Rhizoma, Ligusticum chuanxiong Hort.)

The chemical constituents of Chuanxiong Rhizoma are searched by using “Chuanxiong”, “Chuanxiong Rhizoma”, “Ligusticum chuanxiong Hort.”, “Ligusticum sinense Oliv” and we focused on the literature of the past five years, including English and Chinese literature. The study indicated that 73 chemical compounds in the essential oil from Chuanxiong Rhizoma were detected and 33 compounds with main component Z-Ligustilide were identified by gas chromatgraphy-mass spectrometry (GC-MS) [41]. The other study showed that 30 chemical components in Chuanxiong Rhizoma were separated and identified by using ultra-performance liquid chromatography with electrospray ionization-time of flight mass spectrometry (UPLC-ESI-TOF/MS) technology, including 20 phthalides, 2 flavonoids, 1 alkaloid and 7 phenolic acids [42]. Research on components of dried rhizome from Chuanxiong Rhizoma showed that 10 phthalide derivatives were isolated by using HPLC technology and spectroscopic analyses and 6 of them were identified as ligusticoside A-F for the first time [43].

Chuanxiong Rhizoma contained 324 compounds, which could be divided into 10 categories [41] - [56], including volatile oils (162 compounds, 50%), phthalides (chemical classification instead of plastic pollution) (85 compounds, 26%), phenolic acids (20 compounds, 6%), polysaccharides (17 compounds, 5%), alkaloids (14 compounds, 4%), flavonoids (6 compounds, 2%), ceramides and cerebrosides (5 compounds, 2%), coumarins (3 compounds, 1%), triterpenoids (4 compounds, 1%) and others (8 compounds, 3%) (Table 2, Figure 1(b)).

2.3. Zhimu (Anemarrhenae rhizoma, Anemarrhena asphodeloides Bge.)

We used “Zhimu”, “Anemarrhenae rhizoma”, “Anemarrhena asphodeloides Bge.”, “Anemarrhena asphodeloides Bunge” as key words to search chemical components of Anemarrhenae rhizoma, and the literatures were mainly in recent years which contained all the components as much as possible. It’s reported that 32 chemical constituents were identified in Anemarrhenae rhizoma, which

Chemical constituents in Suanzaoren (Ziziphi Spinosae Semen, Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou)
ClassCompound
Triterpenoids24-hydroxyceanothic acid, 2-o-protocatechuoyl aliphitolic acid, 2α-hydroxypyracrenic acid, 3-ketoursolic acid, 5α,8α-epidioxy-(22e,4r)-ergosta-6,22-dien-3β-ol, acetyl jujuboside B, alhpitolic acid, betulic acid, betulin, betulinic acid, betutin, campesterol, ceanothenic acid, ceanothic acid, epiceanothic acid, jujuboside A, jujuboside A1, jujuboside A2, jujuboside B, jujuboside B1, jujuboside c, jujuboside D, jujuboside E, jujuboside G, jujuboside h, jujuboside I, jujuboside II, jujuboside III, jujuboside IV, lupeol, methyl betulinate, projujuboside B, protojujuboside A, protojujuboside B, protojujuboside B1, protojujuboside D, protojujuboside H, pseudolaroside B, stigmast-4-en-3-one, ursolic acid, 2α-hydroxyursolic acid, 3-o-cis-p-coumaroyl alphitolic acid, 3-o-cis-p-coumaroyl maslinic acid, 3-o-protocatechuoyl ceanothic acid, 3-o-trans-p-coumaroyl alphitolic acid, 3-o-trans-p-coumaroyl maslinic acid, Azukisaponin II, betulonic acid, cecropiacic acid, colubrinic acid, corosolic acid, hydroxyoleanonic acid lactone, isoceanothic acid, lulutonic acid, maslinic aicd, oleanolic acid, pomonic acid, zizyberanalic acid, zizyphus saponin I, zizyphus saponin II, zizyphus saponin III
Flavonoids6-hydroxyflavone, 6'''-(-)-phaseoylspinosin, 6'''-(4'''-o-β-d-glucopyranosyl)-vanilloylspinosin, 6'''-(4''''-o-glu)-p-hydroxyben zoylspinosin, 6'''-diferuloylspinosin, 6'''-dihydrophaseoylspinosin, 6'''-ferulylspinosin, 6'''-pcoumaloylspinosin, 6'''-pcoumaroylspinosin, 6'''-phydroxybenzoylspinosin, 6'''-phydroxylbenzoyspinosin, 6'''-sinapoylspinosin, 6'''-vanilloylspinosin, 6''6'''-diferuloylisospinosin, acylated flavuone c-glycoside I, acylated flavuone c-glycoside II, acylated flavuone c-glycoside III, apigenin-6-c-[(6-o-phydroxybenzyol)-(β-d-glucopyranosyl(1→2)(β-d-glucopyranoside), isospinosin, isovitexin-2, isovitexin-2''-o-(6-feruloyl)-glucopyranoside, isovitexin-2''-o-d-glucopyranoside, isovitexin-2''-o-glucopyranoside, isovitexin-2''-o-β-d-glc, isovitexin-2''-o-β-d-glucopyranoside, puerarin, quercetin, rutin, spinorhamnoside, spinosina, vitexin-4''-o-glucoside, zivulgarin, 7-o-(6'''-o-feruloylglucosyl)-isocytisoside, catechin, 4-o-(6'''-o-feruloylglucosyl)-swertisin, 6"-feruloyl-6'''-vanillylspinosin, isoswertisin, ispinosin, kaemperol-3-o-rutinoside, kaempferol 3-o-α-l-rhamnopyranosyl-(1→2)-o-[o-α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside, kaempferol-3-o-β-d-xylopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyrano-side), kaempferol-3-rutinoside, 2"-o-glucoylisoswertisin, 6'',6'''-diferuloylspinosin, apigenin-6-c-d-glucopyranoside, 2''-b-o-glucopyranosyl swertisin, swertish, isopinosina, epicatechin, 4-(2-methoxy-phenyl)-l-[2-(n-2''-pyridinyl)-p-iodobenza-mido]-ethyl-piperazine, camelliaside B, catechine, nervilifordin J, 6'''-feruloylspinosin, glucosylvitexin, nicotiflorin, saponarin, spinosin, swertisin, isoquercitrin, isovitexin, vicenin II
Alkaloidsamphibine, coclaurine K, lysicamine, nornuciferine Ia, nornuciferine Ib, nuciferine e, sanjoinine A, sanjoinine B, sanjoinine C, sanjoinine D, sanjoinine e, sanjoinine F, sanjoinine G1, sanjoinine G2, sanjoinine Ia (nornuciferine), sanjoinine Ib (norisocorydine), zizyphusine, 5-hydroxy-6-methoxynoraporphine, n-methylasimilobine, 6-(2',3'-dihydroxyl-4'-hydroxymethyl-tetrahydro-furan-1'-yl)-cyclopentene[c]pyrrole-1,3-diol, jubanine C, jubanine F, jujube cyclic peptide, juzirine, nummularine B, adenosine, magnoflorine, tryptophan
Amino Acidsaminocaproic acid, citric acid, cycol(arginine–proline), glutamic acid dipeptide, phenylalanine, 6-glu-coclaurine
Nucleosidescyclic adenosine monophosphate, cyclic guanosine monophosphate, guanosine hydrate, uridine monophosphate
Phenolic Acidshydroxybenzoic acid, linoleic acid, protocatechuic acid, oleic acid
Volatile Oils9,12-octadecadienoic acid, 9-octadecenoic acid, arachidic acid, docosanoic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid
Othersebelin lactone
 Chemical constituents in Chuanxiong (Chuanxiong Rhizoma, Ligusticum chuanxiong Hort.)
ClassCompound
Volatile Oilsbornyl acetate, caryophyllene, germacrene D, germacrene d-4-ol, methyl-eugenol, p-cymen-8-ol, sabinene, terpinen-4-ol, tetradecanoic acid, α-cadinol, α-copaene, α-farnesene, α-phellandrene, α-pinene, α-selinene, α-terpinen, α-terpinene, α-terpineol, α-terpinolene, α-terprinene, α-thujene, β-chamigrene, β-elemene, β-farnesene, β-germacrene, β-linalool, β-myrcene, β-ocimenen, β-phellandrene, β-pinene, β-selinene, γ-cadinene, γ-gurjunene, γ-muurolene, γ-selinene, γ-terpinene, θ-cadinene, τ-muurolol, τ-terpinen, (+)-β-linalool, (1s,5s)-(-)-2(10)-pinene, 2-methoxy-4-vinylphenol, butanal, cubebene, dodecanoic acid, methyl ester hexadecanoic, n-hexadecanoic acid, n-hexadecanoic acid methyl ester, octadecanoic acid, pentadecanoic acid, pentadecanoic acid ethyl ester, spathulenol, cis,cis-linoleic acid, (E)-2-hexenal, (E)-3-decen-2-ol, (N)-(-)-p-menth-1-en-4-ol, 1n-a-pinene, limonene, n-tridecane, o-cymene, n-hexacosane, p-eugenol , p-limonene, p-menth-1-en-8-ol, p-mentha-1,4(8)-diene, p-mentha-1,4-dien-7-ol, l-(+)-ascorbic acid 2,6-dihexadecanoate, n-eicosane, carotol, cedrol, cis-3-hexen-1-ol, cis-β-terpineol, (-)-calamenene, (-)-spathulenol, epiglobulol, igusticoside A, igusticoside b, linoleic acid ethyl ester, linoleic acid methyl ester, (E)-2-methoxy-4-(3-(methylsulfonyl)prop-1-en-1-yl)phenol, (S)-3-ethyl-4-methylpentanol, [(Z)-1,2-diphenyleth-1enyl]-trimethylsilan, 1,1-dimthyl-1,2,3,5,7,8,9,9a-octahydro-benzocyclohepten-6-one, 1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1,-methylethyl)-naphthalene, 1,3,5-dodecatriene, 1,3-cyclohexadiene-5-pentyl, 1,4-cyclohexadiene-1,2-dicarboxylic anhydride, 1,5,5-trimethyl-6-methylene-cyclohexene, 1,5-copaenol, 1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-cyclohexane, 1-hexadecanol, 1-lsopropyl-4-methylbicyclo[3.1.0]hex-2-ene, 1-methoxy adamantane, 1-methyl-4-(1-methylethenyl)-benzene, 1-methyl-4-(methylethyl)-(E)-2-cyclohexenol, 1-phenyl-1-pentanone, 2,4-decadienal, 2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydro-1(2h)-naphthalenone, 2,5-dimethyl-3-hexyne-2,5-diol, 2,6,10-trimethyltetradecane, 2-chloro-1-(2,4-dimethylphenyl)-2-methyl-1-propanone, 2-lsopropenyl-4a,8-dimethyl-1,2,3,4,4a,5,6,7,-octahydronaphthalene, 2-octyl-phenol, 2-pentadecanone-6,10,14-trimethyl , 3,7-dihydro-7-(2-hydroxyethyl)-1,3-dimethyl-1h-purine-2,6-dione, 3-ethyl-4-methylpentan-1-ol, 3-hydroxy-4-methoxypropiophenone, 4(10)-thujene, 4-[β-d-apiofuranosyl-(1→6)-β-d-glucopyranosyloxy]-3-methoxypropio-phenone, 4-hydroxy-2-methylacetophenone, 4-isopropylidene-1-winyl-o-menth-8-ene, 5-pentylcyclohexa-1,3-diene, 6-butyl-1,4-cycloheptadiene, 8-propoxycedrane, 9,12-octadecadienal, a-caryophyllene, angelicide, ansaspirolide, cis,trans-4-methyl-3-oxabicyclo[4.4.0]decane, cis-1-methyl-4-(1-methylethyl)-2-cyclohexen-1-ol, cis-3-buty-4-vinyl-cyclopentene, copaene, cubebol, cubenene, di-epi-1,10-cubenol, diepi-α-cedrene epoxide, diethyl phthalate, dodecamenthylcyclohexasiloxane, dodecanal, ethyl hexadecanoate, ethyl linoleate, heneicosane, humulane-1,6-dien-3-ol, llavandulyl propionate, methyl benzoylformate, neophytadiene, nonadecanol, pentadecyl alcohol, phthalic anhydride, phytol, squalene, tetradecanmethyl-cycloheptasiloxane, trans-1-methyl-4-(1-methylethyl)-2-cyclohexen-1-ol, trans-p-menth-1-en-3-ol, trans-sedanolide, trans-α-bergamotene, tropone, valerophenone, viridiflorol, 1-hydroxy-1-(3-methoxy-4-hydroxyphenyl)-ethane, 3-methoxy-4-hydroxystyrene, coniferyl ferulate, sedanonic acid, 5-hydroxymethyl-6-endo-3-ethoxy-4-hydroxyphenyl-8-oxa-bicyclo[3.2.1]-oct-3-one, succinic acid, ligubenzocycloheptanone A, (S)-2-(2-carboxyl-2-hydro-xyethylthio)-ferulic acid, caffeic acid, ferulic acid, butylidenephthalide, dicaffeoylquinic acid
Alkaloids1-acetyl-β-carboline, 1-β-ethylacrylate-7-aldehydo-β-carboline, 2,3-diphenyl-1,3,4-oxadiazol-3-ium-5-olaten-pentyl-4,5-dihydrophthalide, adenine, adenosine, choline, cyclotetradecane, ligustrazine, l-isobutyl-l-valine anhydride, l-valine-l-valine anhydride, pelolyrine, tetramethylpyrazine, trimethylamine, uracil
Ceramides and Cerebrosides(2N)-2-hydroxy-n-[(2s,3s,4n,8e)-1,3,4-trihydroxypentadec-8-en-2-yl]heptacosanamide, (2N)-2-hydroxy-n-[(2s,3s,4s,8e)-1,3,4-trihydroxyicos-8-en-2-yl]tetracosanamide, (2N)-2-hydroxy-n-(3s,4s,5s)-4-hydroxy-5-[(4e)-undec-4-en-1-yl]tetrahydrofuran-3-yl heptacosanamide, (2N)-n-[(2n,3s,4n,8e)-1-(β-d-glucopyranosyloxy)-3,4-dihydroxyoctadec-8-en-2-yl]-2-hydroxyhexadecanamide, (2N)-n-[(2s,3n,4e,8e)-1-(β-d-glucopyranosyloxy)-3-hydroxydodeca-4,8-dien-2-yl]-2-hydroxydocosanamide
Coumarins5,7,8-trimethyl-dihydrocoumarin, scopoletin, cnidioside A
Flavonoidsapigenin, apigenin-7-o-β-d-glueuronide, daidzein, astragalin, 2-(1-oxopentyl)-benzoic acid methyl ester
Phenolic Acidsicariside F2, ligusticumacid A, ligusticumacid B, ligusticumacid C, ligusticumacid d, ligusticumacid e, ligusticumacid F, 5-hydroxymethyl-6-endo-3-methoxy-4-hydroxyphenyl-8-oxa-bicyclo (3.2.1)-oct-3-one, chrysophanol, folic acid, gallic acid, palmitinic acid, p-hydroxybenzoic acid, sinapic acid, vanillin, chlorogenic acid, vanillic acid, linoleic acid, protocatechuic acid, oleic acid
Phthalideslevistilide A, ligustilide, 3-butylene-4,5-dihydroxyph-thailde, senkyunolide Q, senkyunolide R, senkyunolide S, e-senkyunolide E, ligusticoside A, z-ligustilide , z-senkyunolide E, (z,z')-6,8',7,3'-diligustilide, 3-butylidene-6-hydroxy-5,6-dihydrophthalide, 3-carboxyethyl-phthalide, 4,5-dihydro-3-butylidenephthalide, 3,6,8,3a-diligustilide, 3,8-dihydrodiligustilide, 3-butylidenephthalide, 3-hydroxy-4,5,6,7-tetrahydro-6,7-dihydroxy-3-butylphthalide, 4,5-dihydro-3-butylphthalide, 4,7-dihydroxy-3-butylphthalide, 4-hydroxy-3-butylphthalide, butylphthalide, chuanxiongins A, chuanxiongins B, chuanxiongins C, chuanxiongins d, chuanxiongins E, chuanxiongins F, chuanxiongnolide A, chuanxiongnolide B, chuanxiongnolide R1, chuanxiongnolide R2, hexahydro-3-butylphthalide, levistolide A, neocnidilide, senkyunolide B, senkyunolide C, senkyunolide E, senkyunolide G, senkyunolide K, senkyunolide l, senkyunolide M, senkyunolide N, senkyunolide O, senkyunolide P, tokinolide B, wallichilide, z,z'-3,3',8,8'-diligustilide, z'-3,8-dihydro-6,6',7,3'a-diligustilide, z-6,7-epoxyligustilide, z-butylidenephthalide, z-ligustilide dimer e-232, 3-butylidene-7-hydroxyphthalide, 3-carboxyrthyl-phthalide, 6-hydroxy-senkyunolide B, celephthalide A, chuanxiongoside A, chuanxiongoside B, (3'z)-(3s,8n,3a's,6'n)-4,5-dehydro-3.3a',8.6'-diligustilide, (3'z)-(3s,8s,3a's,6'n)-4,5-dehydro-3.3a',8.6'-diligustilide, thiosenkyunolide C, trans-neocrididilide, chuanxiongdiolide A, chuanxiongdiolide B, chuanxiongdiolide L1, chuanxiongdiolide L2, chuanxiongdiolide L3, chuanxiongdiolide L4, chuanxiongdiolide L5, chuanxiongdiolide R1, chuanxiongdiolide R2, chuanxiongdiolide R3, igustilide, 3-butyl-4-hydroxyphthalide, 3-butylphthalide, e-ligustilide, riligustilide, senkyunolide A, senkyunolide D, senkyunolide F, senkyunolide h, senkyunolide I, senkyunolide J, z,z'-6,8',7,3'-diligustilide, cnidilide
PolysaccharidesLCA, LCB, LCC, LCX0, LCX1, LCX2, LCP-1, LCP-2, LCP-3, LCP-4, Arabinose, galactose, galacturonic acid, glucose, glucuronic acid, nhamnose, mannose
Triterpenoidsprogesterone, xiongterpene, Globulol, ergosterol peroxide
Others(-)-alloaromadendrane-4β,10α,13,15-tetrol, 3-o-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside, 4-pentylcyclohex-3-ene-1α,2β-diol, campest-4-en-3-one, monopalmitin, β-d-apiofuranosyl-(1→6)-β-d-glucopyranosyl-3,4-dimethoxy-benzoate, aurantiamide acetate, lignoceric acid

contained 18 steroids, 6 flavonoids, 4 phenylpropanoids, 2 alkaloids, and 2 benzophenones using UPLC-Q-TOF/MS combination with characteristic fragments filter and neutral loss filter method [57]. The study on chemical constitutions of crude Anemarrhenae rhizoma (CAR) and salt-processed Anemarrhenae rhizoma (SAR) showed that a total of 24 components as main contributors had significant difference, and 7 main constituents were simultaneously determined by ultra-high-performance liquid chromatography-quadrupole mass spectrometry (UHPLC-MS), timosaponin N, timosaponin E1, timosaponin BII, timosaponin BIII, anemarrhenasaponin I, timosaponin AII and timosaponin AIII [58].

We sorted out 163 components of Anemarrhenae rhizoma [57] - [76], which were classified into 10 categories, including steroids (84 compounds, 51%), flavonoids (25 compounds, 15%), alkaloids (13 compounds, 8%), coumarins (8 compounds, 5%), volatile oils (8 compounds, 5%), triterpenoids (5 compounds, 3%), polysaccharides (6 compounds, 4%), lignans (7 compounds, 4%), phenolic acids (1 compound, 1%) and others (6 compounds, 4%) (Figure 1(c), Table 3).

2.4. Fuling (Poria, Poria Cocos (Schw.) Wolf.)

We used key words “Fuling”, “Poria”, “Poria cocos (Schw.) Wolf.”, “Wolfiporia extensa (Peck) Ginns” to find the ingredients in Poria, and selected literatures in the past five years. We found many methods have been developed for analysis and quality control of Poria. For instance, qualitative and quantitative methods to analyze carbohydrates (polysaccharides, oligosaccharides and monosaccharides) in three different parts (epidermis, middle and inner) of Poria by high performance gel permeation chromatography coupled with charged aerosol detector (HPGPC-CAD), altra-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UHPLC-QqQ-MS/MS), PCA and orthogonal partial least squared discriminant analysis (OPLS-DA) [77]. It is an efficient dereplication strategy to identify triterpene acid analogues in Poria based on ultra-performance liquid chromatography with electrospray ionisation quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-QTOF-MS/MS), and 62 triterpene acids were characterized [78]. A method based on UHPLC-MS combined metabolomics approach is established to explain the distribution of triterpene compounds in four parts, which are Poriae Cutis (PC), Rubra Poria (RP), White Poria (WP) and Poria cum Radix Pini (PRP) and 51 triterpene compounds are tentatively identified in Poria. The PC and PRP show a quite clear discrimination by the PCA and OPLS-DA, and 12 differential compounds are found [79].

The four classes of chemical components in Poria included 204 compounds [77] - [96], containing triterpenoids (137 compounds, 67%), polysaccharides (58 compounds, 28%), alkaloids (2 compounds, 1%) and others (7 compounds, 4%) (Table 4, Figure 1(d)).

2.5. Gancao (Licorice, Glycyrrhiza uralensis Fisch., Glycyrrhiza inflata Bat. or Glycyrrhiza Glabra L.)

We used key words “Gancao”, “Zhigancao”, “Licorice”, “Glycorrhizae Radix et Rizoma”, “Glycorrhiza urensis Fisch.”, “Glycorrhiza inflata Bat.”, “Glycorrhiza glabra L.” to find the ingredients in Licorice, and we were mainly based on the literature of the past five years and delete the literature with duplicate components.

Chemical constituents in Zhimu (Anemarrhenae rhizoma, Anemarrhena asphodeloides Bge.)
ClassCompound
Steroids(25R)-26-o-β-d-glucopyranosyl-5α-furostane-20(22)-en-3β,26-diol-3-o-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, (25S)-26-o-β-d-glucopyranosyl-22-hydroxy-5β-furostane-3β,26-diol, 3-o-β-d-glucopyranosyl-(1→2)-o-β-d-galactopyranoside, (25S)-officinalisnin-I, 20(22)-en-5β-furost-3β,15α-diol-3-o-β-d-glucopyranosyl-(1→2)-β-d-galactopyranoside, 21-formyl sarsasapogenin, 21-hydroxysarsasapogenin, 25(27)-ene-anemarrhenasaponin I, 25(27)-ene-Gurilioside H, 25(27)-ene-timosaponin AII, 25(27)-ene-timosaponin AIII, 25(27)-ene-timosaponin N, 25R-timosaponin AIII, 25R-timosaponin BII, 25R-timosaponin BIII, 25R-timosaponin D, 25R-timosaponin E, 25S-karatavioside C, 2-hydroxyl-timosaponin AIII, 3,4-dihydroxyallylbenzene-3-o-α-L-rhamnopyranosyl(1→6)-β-d-glucopyranoside, anemarnoside A, anemarnoside B, anemarrhena S1, anemarrhena S2, anemarrhena S3, anemarrhena S4, anemarrhena S5, anemarrhena saponin III, anemarrhenasaponin F, anemarrhenasaponin I, anemarrhenasaponin Ia, anemarrhenasaponin II, anemarsaponin B II, asparagoside G, curilioside H, degalactotigonin, desgalactotigonin, dimethisterone, diuranthoside A, f-gitonin, filicinoside-A, hostaplantagineoside C, karatavioside C, macrostemonoside F, macrostemonoside J, officinalisinin-I, petunioside N, purpureagitoside, sarsasapogenin, smilageninoside, solanigroside F, spicatoside B, timopregnane A, timosaponin AI, timosaponin AII, timosaponin AIII, timosaponin AIV, timosaponin B, timosaponin B I, timosaponin B II, timosaponin B III, timosaponin B IV, timosaponin C, timosaponin D, timosaponin E, timosaponin E1, timosaponin F, timosaponin G, timosaponin H1, timosaponin I1, timosaponin I2, timosaponin L, timosaponin N, timosaponin P, timosaponin Q, timosaponin U, timosaponin V, timosaponin W, timosaponin E1, tomatoside A, tuberoside G, uttroside B, xilingsaponin B, zimoside A
Alkaloidsadenosine, coumaroyl tyramine, cyclo dileucyl, cyclo hetaleucyl, cyclo hexaleucyl, cyclo nonaleucyl, cyclo octaleucyl, cyclo pentaleucyl, cyclo tetraleucyl, cyclo trileucyl, n-cis-feruloyl tyramine, n-trans-feruloyltyramine, tryptophan
Polysaccharidesd-galactose, d-galacturonic acid, d-glucose, d-mannose, l-arabinose, l-rhamnose
Phenolic Acidsoleic acid
Flavonois(2,6-dihydroxy-3-(((1s,4s,6r)-4-hydroxy3,7-dioxabicyclo[4.1.0]heptan-4-yl)methyl)-4-methoxyphenyl)(4-hydroxyphenyl)methanone, (2s)-7,4′-dihydroxy-5-methoxyflavone, (4-hydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone, (s)-5-(2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl)pyrrolidin-2-one, 2,4',6-trihydroxy-4-methoxy benzophenone, 2,6,4'-trihydroxy-4-methoxy Benzophenone, 2',4',4-trihydroxy chalcone, 2'-o-methylisoliquiritigenin, 2'-o-methylphloretin, 4',6-dihydroxy-4-methoxybenzophenone-2-o-(2''),3-c-(1'')-1''-desoxy-α-l-fructofuranoside, anemarchalconyn, e-4'-demethyl-6-methyleucomin, E-5,7-dihydroxy-3-(4'-hydroxybenzylidene)chroman-4-one, foliamangiferoside A, iriflophene, iriflophenone, iriflpohenone-3-c-β-d-glucoside, isomangiferin, isosakuranetin, isovitexin, mangiferin, mangiferoxanthone A, methyl 2-(2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl) acetate, neomangiferin, vitexin
Triterpenoidsplatycodin D, platycodin D2, platycodin D3, platycoside A, polygalacin D2
Volatile Oilsdihydroxy-octadecadienoic acid, dihydroxy-octadecaenoic acid, dihydroxy-octadecatrienoic acid, hydroxy-octadecadienoic acid, hydroxy-octadecatrienoic acid, inolenic acid, tearic acid, trihydroxy-octadecaenoic acid
Coumarinscis-hinokiresinol, hinokiresinol, methoxy-cis-hinokiresinol, monomethyl-cis-hinokiresinol, oxy-hinokiresinol, trans-hinokiresinol, broussonin A, broussonin B
Lignans3''-hydroxy-4''-methoxy-4''-dehydroxynyasol, 3''-methoxynyasol, 4-hydroxy acetophenone, 4-hydroxybenzaldehyde, 4'-o-methylnyasol, anemarcoumarin A, nyasol,
Others(s)-5-(2-hydroxy-5-(3-(4-hydroxy phenyl) propyl)-4-methoxy phenyl) pyrrolidin-2-one, aneglycoside A, aneglycoside B, aneglycoside C, phytosphingosine, α-d-Glucose monoallyl ether
 Chemical constituents in Fuling (Poria, Poria cocos (Schw.) Wolf)
ClassCompound
Polysaccharidesab-PCM3-I-S1, ab-PCM3-I-S2, ab-PCM3-I-S3, ab-PCM3-I-S4, ab-PCM3-I-S5, ac-PCM2, ac-PCM3-I-S1, ac-PCM3-I-S2, ac-PCM3-I-S3, ac-PCM3-I-S4, ac-PCM3-I-S5, arabinose, carboxymethylated P. cocos polysaccharides, carboxymethylpachymaram, CMP, CS-PCS3-II, fucose, galactose, galacturonic acid, glucose, glucuronic acid, mannose, oxidized P. cocos polysaccharides, pachyman, PC-II, PCP3-I, PCP3-II, PCP4-I, PCP4-II, PCP-E, PCP-H, PCP-M, PCPS, PCP-U, PCS1, PCS2, PCS3-I, PCS3-II, PCS4-I, PCS4-II, PCSC, PCWPS, PCWPW, Pi-PCM, Pi-PCM0, Pi-PCM1, Pi-PCM2, Pi-PCM3-I, poria cocos polysaccharide-1(PCP-1), PPSW-1, rhamnose, rib, ribose, sum, wc-PCM0, wc-PCM1, wc-PCM2, xylose
Triterpenoids11β-ethoxydaedaleanic acid A, 15α-hydroxy-3-oxolanosta-8,24-dien-21-oic acid, 15α-hydroxydehydrotrametenolic acid, 15α-hydroxydehydrotumulosic acid, 15α-hydroxyeburiconic acid, 16-deoxyporicoic acid B, 16-hydroxy-3,24-dioxolanosta-7,9-dien-21-oic acid, 16-o-acetyl pachymic acid, 16α,25-dihydroxy dehydroeburiconic acid, 16α,25-dihydroxyeburiconic acid, 16α,27-dihydroxydehydrotrametenoic acid, 16α,29-dihydroxy eburiconic acid, 16α-acetoxy-26,27-dimethoxyl-lanosta-8,24-dien-21-oic acid, 16α-acetoxy-lanosta-7,9,24-dien-21-oic acid, 16α-acetoxy-lanosta-8,24-dien-21-oic acid, 16α-acetoxypolyporenic acid C, 16α-acetyloxy-24-methylene-3-oxolanosta-7,9-dien-21-oic acid, 16α-acetyloxye buriconic acid, 16α-hydroxy-3-oxolanosta-8,24-dien-21-oic acid, 16α-hydroxydehydrotrametenonic aicd, 16α-hydroxy eburiconic acid, 16α-hydroxy-lanosta-7,9,24-trien-21-oic acid, 16α-hydroxy-lanosta-8,24-dien-21-oic acid, 16α-hydroxy trametenolic acid, 16,29-dihydroxy-3,4-seco-lanosta-4(28),8,24(31)-trien-3,21-dioic acid, 2'-3'-dihydrosorbicillin, 25,26-dihydroxy dehydropachymic acid, 25-hydroxy-3-epidehydrotumulosic acid, 25-hydroxy-3-epitumulosic acid, 25-hydroxy pachymic acid, 25-hydroxy polyporenic acid C, 25-hydroxyporicoic acid C, 25-hydroxyporicoic acid H, 25-methoxy-29-hydroxy poricoic acid HM, 25-methoxy poricoic acid A, 25α-hydroxytumulosic acid, 26-hydroxyporicoic acid DM, 26-hydroxy poricoic acid G, 29-hydroxydehydropachymic acid, 29-hydroxydehydrotumulosic acid, 3-(2-hydroxy acetoxy)-5α,8α-peroxydehydrotumulosic acid, 3,4-seco-lanosta-4,7,9,24-tetraen-3,21-dioic acid, 31-hydyoxyl-16-o-acetylpachymic acid, 3-acetyloxy-16α-hydroxy trametenolic acid, 3-epi-(3'-hydroxy-3'-methylglutaryloxyl)-dehydrotumulosic acid, 3-epi-dehydropachymic acid, 3-epi-dehydrotumulosic acid, 3-epi-pachymic acid, 3-o-acetyl-16α,26-dihydroxytrametenolic acid, 3-o-acetyl-16α-hydroxydehydrotrametenolic acid, 3-o-acetyl-16α-hydroxytrametenolic acid, 3-o-acetyl-dehydroeburicoic acid, 3-oxo-16α-hydroxy-lanosta-7,9(11),24-trien-21-oic acid, 3-oxo-6,16α-dihydroxy-lanosta-7,9(11),24(31)-trien-21-oic acid, 3-oxo-lanosta-7,9(11),24(31)-trien-21-oic acid, 3-oxo-lanosta-7,9(11),24-trien-21-oic acid, 3α,16α,25-Trihydroxylanosta-8,24-dien-21-oic acid, 3β,15α-Bis(acetyloxy)-24-methylenelanost-8-en-21-oic acid, 3β,15α-dihydroxy-24-oxolanosta-8-en-21-oic acid, 3β,15α-dihydroxy lanosta-7,9(11),24-triene-21-oic acid, 3β,16α-bis(acetyloxy)-29-hydroxylanosta-8,24-dien-21-oic acid, 3β,16α-dihydroxy-24-hydroxy methyl lanosta-7,9-dien-21-oic acid, 3β,16α-dihydroxy lanosta-7,9(11),24(31)-trien-21-oic acid, 3β,16α-dihydroxylanosta-7,9(11),24-trien-21-oic acid, 3β,26-dihydroxy-lanosta-7,9,24-trien-21-oic acid, 3β-acetoxy-16α,26-dihydroxylanosta-8,24-dien-21-oic acid, 3β-acetoxy-lanosta-7,9(11),24-trien-21-oic acid, 3β-acetyloxy-16α-hydroxy-24-oxolanost-7,9(11)-dien-21-oic acid, 3β-acetyloxy-16α-hydroxy-24-oxolanost-8-en-21-oic acid, 3β-hydroxy-16α-acetoxylanosta-7,9(11),24-trien-21-oic acid, 3β-p-hydroxybenzoyldehydrotumulosic acid, 3α-hydroxyl-26-methoxyl-8,24(31)-diene-21-oic acid, 3β-acetoxy-16α-hydroxy-lanosta-8,24-diene-21-oic acid, 5α,8α-Peroxydehydrotumulosic acid, 6,16α-dihydroxydehydroeburiconic acid, 6,16α-dihydroxydehydrotrametenonic acid, 6-hydroxy polyporenic acid C, 6α-hydroxydehydropachymic acid, 6α-hydroxy-polyporenic acid C, 9,11-dehydroergosterol peroxide, 6-hydroxy-3β,16α-diacetoxy-lanosta-7,9,24-tetraen-21-oic acid, acetoxyeburicoic acid, acetyl-eburicoic acid, ceanphytamic acid A, ceanphytamic acid B, daedaleanic acid A, daedaleanic acid B, dehydroeburic acid, dehydroeburicoic acid, dehydroeburicoic acid monoacetate, dehydroeburiconic acid, dehydropachymic acid, dehydrosulphurenic acid, dehydrotrametenolic acid, dehydrotrametenonic acid, dehydrotumulosic acid, dehypachymic acid, deyhdrotarmetenolic acid, eburicoic acid, eburicoic acid acetate, ergosterol
peroxide, harzianone, hederagenin, hispindic acid B, lanosta-7,9,24-trien-21-oic acid, lanosta-8,24-dien-21-oic acid, me trametenolate, oleanic acid, pachymic acid, pinicolic acid, pinicolic acid A, pinicolic acid E, polyporenic acid C, poriacosone A, poriacosone B, poricoic acid A, poricoic acid AE, poricoic acid AM, poricoic acid B, poricoic acid C, poricoic acid CE, poricoic acid CM, poricoic acid D, poricoic acid DM, poricoic acid E, poricoic acid F, poricoic acid G, poricoic acid GE, poricoic acid GM, poricoic acid h, poricoic acid HE, poricoic acid HM, poricoic B, pregna-7-en-3α,11α,15α,20-quadriol, trametenolic acid, tumulosic acid, ursolic acid
Alkaloidsadenosine, thymine
Others(3S,6S)-3-[(1R)-1-hydroxyethyl]-6-(phenylmethyl)-2,5-piperazinedione, (5-formylfuran-2-yl) methyl 2-(4-hydroxyphenyl) acetate, (5-formylfuran-2-yl) methyl 2-hydroxy propanoate, 5-hydroxy methylfurfural, sohiracillinone, sohirnone A, sorbicillin

Many methods have been developed for the analysis and the quality control of Licorice. The 58 phenolic acids including 11 new compounds (glycybridins A-K) were isolated from Licorice using nuclear magnetic resonance (NMR) and MS analyses combination with experimental and computed electronic circular dichroism data [97]. The 8 triterpenoids including glyuralsaponin A-G were separated from Licorice root by using ultraviolet (UV), infrared (IR), NMR spectrum and other technologies [98]. In addition, 122 chemical ingredients including glycyuralin A-F from the roots and stems of Licorice were isolated and identified adopting a combined strategy using NMR and MS spectroscopic data measurement [99].

We totally collected 260 components of Licorice [97] - [109], which were classified into 6 categories, including flavonoids (112 compounds, 43%), triterpenoids (51 compounds, 20%), phenolic acids (72 compounds, 28%), coumarins (11 compounds, 4%), stilbenoids (5 compounds, 2%) and others (9 compounds, 3%) (Figure 1(e), Table 5).

3. The Chemical Constituents in Suanzaoren Decoction

We used “Suanzaoren decoction”, “Suan-Zao-Ren decoction”, “Suan-Zao-Ren-Tang”, “Zizyphus Combination”, “Suanzaoren Formulae”, “Suan Zao Ren Tang”, ”Ziziphus spinose decoction”, “Suanzaoren prescription” as key words to search chemical components in SZRD, and classified them according to their chemical structure. Results showed that only five literatures on the ingredients of SZRD were reported. For example, 101 constituents are identified in Suan-Zao-Ren granule using UHPLC-Q-TOF-MS coupled with multiple data processing approaches [110]. These 48 components were characterized in SZRD using liquid chromatography time-of-flight mass spectrometry (LC-Q/TOF-MS) and liquid chromatography coupled with ion trap mass spectrometry (LC-IT-MS) technology and 31 compounds were identified for the first time [111]. The 22 chemical compounds were isolated in SZRD by using ultra-performance liquid chromatography coupled with electrospray ionization/quadrupole-time-of-flight mass spectrometry (UPLC-ESI-Q-TOF-MS)

Chemical constituents in Gancao (Licorice, Glycyrrhiza uralensis Fisch., Glycyrrhiza inflata Bat. or Glycyrrhiza glabra L.)
ClassCompound
Flavonoids7,4'-dihydroxyflavone 7-O-glucopyranoside, apigenin 6-C-rhamnopyranoside-8-C-[6'''-(3-hydroxy-3-methylglutaroyl)]-glucopyranoside, daidzin, glucoliguiritin apioside, glycyroside, isoliquiritigenin 4,4'-di-O-glucopyranoside, isoliquiritin, isoschaftoside, isoviolanthin, liquiritigenin 7,4'-di-O-glucopyranoside, liquiritin, liquiritin apioside, neoisoliquiritin, neoliquiritin, schaftoside, soliquiritin apioside, sophoraflavone B, syringic acid 4-O-glucopyranoside, vicenin II, (2R,3R)-3,4',7-trihydroxy-3'-prenylflavane, (2s)-abyssinone I, 2,3-dehydrokievitone, 3,4-didehydroglabridin, 3'-hydroxy-4'-O-methylglabridin, 3-hydroxyglabrol, 4'-O-methylglabridin, 5,8-dihydroxy-flavone-7-O-beta-D-glucuronide, 5-hydroxy-8-methoxyl-flavone-7-O-beta-D-glucuronide, 6-prenylnaringenin, 7,2'-dihydroxy-4'-methoxy-8-(3-methyl-2-butenyl) isoflavanone, 8-prenyl-phaseollinisoflavan, abyssinone II, chalcones isoliquiritin, derrone, echinatin, euchrenone A5, flavanone, flavonol, formononetin, galbrene, genistein, glabranin, glabrene, glabridin, glabroisoflavanone A, glabroisoflavanone B, glabrol, glabrone, glisoflavanone, glucoliquiritin apioside, glychionide A, glychionide B, glycyrrhisoflflavone, glyinflanin H, glyzarin, hispaglabridin A, hispaglabridin B, isobavachalcone, isoflavan, isoflavanone, isoflavone, isolicoflavonol, isoliquiritigenin, isoliquiritin apioside, isoononin, isoquercitrin, isotrifoliol, isoviolantin, kanzonol B, kanzonol C, kanzonol U, kanzonol W, kanzonol X, kanzonol Y, kanzonol Z, kumatakenin, licochalcone A, licochalcone B, licochalcone C, licochalcone D, licochalcone E, licoflavanone, licoflavonol, licoflflavone A, licoflflavone B, licoflflavone C, licoisoflavones A, licoisoflavones B, licoisoflflavone A, licorice glycoside A, licorice glycoside B, licorice glycoside C1, licorice glycoside C2, licorice glycoside D1, licorice glycoside D2, licuraside, liquiritigenin, lupiwighteone, mangiferin, medicarpin, naringenin, ononin, paratocarpins B, parvisoflavones A, pinocembrin, prunetin, retrochalcones, rhamnoliquiritin, shinflavanone, shinpterocarpin, violantin, wighteone
Triterpenoids12-acetoxyganoderic acid F, 18β-glycyrrhetinic acid, 22β-acetoxylglycyrrhizin, 24-hydroxy-licorice saponin A3, 3β-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-24-hydroxylglabrolide, glabrolide, glycyrrhetic acid, glycyrrhetic acid-3-O-mono-β-d-glucuronide, glycyrrhizic acid, glyuralsaponin A, glyuralsaponin B, glyuralsaponin C, glyuralsaponin D, glyuralsaponin E, glyuralsaponin F, glyuralsaponin G, glyuralsaponin H, isoglycyrrhizin, licorice saponin A3, licorice saponin B2, licorice saponin C2, licorice saponin E, licorice saponin E2, licorice saponin G2, licorice saponin N4, squasapogenol GP-B2, uralsaponin B, uralsaponin F, yunganoside K2, 22β-acetoxyglycyrrhizin, 22β-acetoxyl-glycyrrhaldehyde, 3-O-glucuronopyranosyl-glycyrrhetinic acid, 3β-O-[glucuronopyranosyl-(1→2)-glucuronopyranosyl]-olean-9,12-diene-30-oic-acid, araboglycyrrhizin, glycyrrhetinic acid, glycyrrhizin, licorice-saponin H2, licorice-saponin J2, uralsaponin C, uralsaponin M, uralsaponin N, uralsaponin P, uralsaponin Q, uralsaponin R, uralsaponin S, uralsaponin T, uralsaponin U, uralsaponin V, uralsaponin W, uralsaponin X, uralsaponin Y
Phenolic acids11b-hydroxy-11b,1-dihydromedicarpin, 1-methoxyphaseollin, 2'-hydroxyisolupalbigenin, 2-one-4-methoxy-pyran, 3-methoxy-9-hydroxy-pterocarpan, 5,7,4'-trihydroxy-3'(3-methylbut-2-enyl)-3-methoxy flavone, 6,8-diprenylgenistein, 6-C-prenylorobol, 7-methoxy-2',4'-dihydroxy isoflavone, 7-O-methylluteone, abiochanin A, allolicoisoflavone B, angustone A, daidzein, dehydroglyasperin C, dehydroglyasperin D, gancaonin I, gancaonin L, genkwanin, glicophenone, glicoricone, glyasperin C, glyasperin D, glycybridins A, glycybridins B, glycybridins C, glycybridins D, glycybridins E, glycybridins F, glycybridins G, glycybridins H, glycybridins I, glycybridins J, glycybridins K, glycyfuranocoumarin A, glycyfuranocoumarin B, glycyfuranocoumarin C, glycyfuranocoumarone A, glycyrol, glycyrrhiza-isoflavone C, glycyuralin A, glycyuralin B, glycyuralin C, glycyuralin D, glycyuralin E, glycyuralin F, glyurallin A, hirtellanine I, homobutein, isoangustone A, isoderrone, isoglabrone, isoglycycoumarin, isoglycyrol, isolupalbigenin, kaempferol, kaempferol 3-O-methyl ether, kumatakenin B, licoarylcoumarin, licocoumarone, licoflavone A, licoisoflavanone, licoisoflavone A, licoisoflavone B, licoricidin, licoricone, luteone, phaseollin, pratensein, semilicoisoflavone B, topazolin, uralenol
Stilbenoidsdihydro-3,3',4'-trihydroxy-5-O-isopentenyl-6-isopentenylstilbene, dihydro-3,3'-dihydroxy-5β-d-O-glucopyranosyloxy-4'-methoxystilbene, dihydro-3,5,3'-trihydroxy-4'-methoxystilbene, dihydro-3,5-dihydroxy-4'-acetoxy-5'-isopentenylstilbene, dihydrostilbenes
Coumarinsglabrocoumarin, glabrocoumarone A, glabrocoumarone B, glycocoumarin, glycycoumarin, glycyrin, herniarin, licofuranocoumarin, licopyranocoumarin, liqcoumarin, umbelliferone
Others[6'',6''-dimethyl pyrano (2'',3'':4,5)]-3'-γ,γ-dimethylallyl-2',3,4'-trihydroxychalcone, 1'',2''-dehydrocyclokievitone, 2'-O-demethybidwillol, dehydroglyceollin I, erybacin, licoagrocarpin, licoagrochalcone A, xambioona, gup-II

method with MassLynxTM MassFragment [112]. There were 13 active marker compounds (neomangiferin, mangiferin, spinosin, liquiritin apioside, liquiritin, 6'''-feruloylspinosin, senkyunolide I, timosaponin BII, isoliquiritoside, timosaponin C, jujuboside A, jujuboside B, and timosaponin AIII) were separated in diverse SZRD including lab-prepared Suanzaoren oral liquid, Suanzaoren mixture, and clinical Suanzaoren granules using high-performance liquid chromatography with diode array detection and evaporative light scattering detection (HPLC-DAD-ELSD) [113]. In addition, 11 chemical components (neomangiferin, mangiferin, spinosin, liquiritin apioside, liquiritin, fumalic acid, 6'''-feruloylspinosin, senkyunolide I, isoliquiritin, glycyrrhizic acid and senkyunolide A) of SZRD in different batches, including SZRD extracts, lab-made SZRD granules and clinical medicine, were determined by HPLC-PDA, which indicated that HPLC-PDA method would be helpful to improve quality evaluation and quality control in productive processes [114]. The 8 compounds (jujuboside, spinosin, ferulic acid, senkyunolide I, sarsasapogenin, mangiferin, liquiritoside and glycyrrhizic acid) were considered chemical quality control standard of SZRD [115].

We totally collected 145 compounds of SZRD in all [110] [111] [112] [113] [114], which were divided into 10 categories, including flavonoids (53 compounds, 36%), alkaloids (2 compounds, 1%), coumarins (7 compounds, 5%), phenolic acids (4 compounds, 3%), phthalide (14 compounds, 10%), triterpenoids (33 compounds, 23%), steroids (19 compounds, 13%), volatile oils (7 compounds, 5%), polysaccharide (1 compound, 1%) and others (5 compounds, 3%) (Figure 1(f), Table 6). Flavonoids, one of the main active ingredients found at present, contained the largest number of ingredients in SZRD [116].

4. Comparative Analysis of Chemical Constituents in Herbs and Suanzaoren Decoction4.1. Comparative Analysis of Chemical Constituents in Herbs

We obtained a total of 1104 chemical components without duplication in 5 herbs (Figure 2(a)). Adenosine existed in Ziziphi Spinosae Semen, Chuanxiong Rhizoma, Poria and Anemarrhenae rhizoma. Oleic acid existed in Anemarrhenae

Chemical constituents in suanzaoren decoction
ClassCompound
Flavonoids(3R)-Vestitol, 5,7-Dihydroxyflavanone, 6''-Feruloyspinosin, 6''''-(4''''-O-β-D-glucopyranosyl)vanilloyl spinosin, 6,8-di-C-glucosyl-2(R)-naringenin, 6,8-di-Cglucosyl-2(s)naringenin, 6'''-Feruloylspinosin, 6''''-dihydrophaseoylspinosin, 6''-feroylspinol, choerospondin, echinatin, formononetin, gancaonin A, gancaonin H, glabrene, glabrol, glucoliquiritin, glucosylvitexin, glyinflanin A, isoliquiritigenin, isoliquiritin, isolquiritigenin, isoshaftoside, isoviolanthin, isovitexin, kanzonol F, kanzonol H, kumatakenin, licochalcone A, licochalcone B, licoleafol, licorice glycoside A, licorice glycoside D1, licorice glycoside D2, licorice glycoside E, licoricidin, licorisoflavan A, liquiritigenin, liquiritin, liquiritin apioside, lupiwighteone, mangiferin, neolicuroside, neomangiferin, nicotiflorin, ononin, pinocembrin, saponarin, schaftoside, shaftoside, spinosin, swertisin, vicenin II
Triterpenoids16-Deoxyporicoic acid B, 16α-Hydroxytrametenolic acid, 22-Acetoxyglycyrrhizin, 3β,16α-Dihydroxylanosta-7,9(11),24-trien-21-oic acid, apioglycyrrhizin, betulinic acid, dehydrotrametenolic acid, dehydrotrametenonic acid, dibutyluralsaponin A, glabric acid, glycyrrhetic acid, glycyrrhizic acid, glycyrrhizin, isoliquiritoside, jujuboside A, jujuboside B, liangwanoside I, licorice saponin H2, licorice saponin J, licorice saponin K2, licorice saponine A3, licorice saponine G2, licoricesaponin B2, oleanolic acid, pachymic acid, polyporenic acid C, poricoic acid A, poricoic acid B, uralsaponin A, uralsaponin B, yunganoside J1, yunganoside K2, yunganoside L1
Coumarinsglycycoumarin, glycyrin, glycyrol, hedysarimcoumestan, inflacoumarin A, isoglycyrol, neoglycyrol
Steroids(25s)-26-O-β-D-Glucopyranosyl-22-hydroxy-5β-furostane-3β, 26-diol3-O-β-D-Glucopyranosyl-(1-2)-O-β-D-galactopyranoside, (25s)-26-O-β-D-Glucopyranosyl-22-hydroxy-5β-furostanolalkenyl-3β, 26-diol3-O-β-D-glucopyranosyl-(1-2)-O-β-D-galactopyranoside, anemarsaponin B, anemarsaponin C, anemarsaponin E, anemarsaponin F, anemarrhena saponin II, anemarrhena saponin I, diosgenin, sarsasapogenin, timosaponin AI, timosaponin AIII, timosaponin AIV, timosaponin B II, timosaponin C, timosaponin E1, timosaponin E, timosaponin N, xilingsaponin B
Phenylpropanoidstimobiose
Phenolic Acidschlorogenic acid, vanillic acid, neochlorogenic acid, ryptochlorogenic acid
Phthalide3-Butyl-4-hydroxyphthalide, 3-Butylphthalide, cnidilide, E-butylidenephthalide, E-ligustilide, riligustilide, senkyunolide A, senkyunolide D, senkyunolide F, senkyunolide H, senkyunolide I, senkyunolide J, Z,Z'-6,8',7,3'-diligustilide, Z-ligustilide
Alkaloidsamphibine D, magnoflorine
Volatile oilsbutylidenephthalide, caffeic acid, dicaffeoylquinic acid, ferulic acid, fumalic acid, neochlorogenic acid, palmitic acid, yptochlorogenic acid
Others3β-30-hydroxy-11,30-dioxoolean-12-en-3-yl-2-O-a-L-arabinopyrano-syl-b-Dglucopyranosiduronic acid, emodin, liguiritigenin-7-O-β-D-apiofuransyl-40-O-3-D-glucose, ligustilide dimer, unganoside K2

rhizoma, Chuanxiong Rhizoma and Ziziphi Spinosae Semen.

There are 8 common components presenting in Chuanxiong Rhizoma and Poria, which are galacturonic acid, mannose, arabinose, ergosterol peroxide, rhamnose, galactose, glucuronic acid, and glucose. Ziziphi Spinosae Semen and Chuanxiong Rhizoma contain linoleic acid and protocatechuic acid. Ziziphi Spinosae Semen and Anemarrhenae rhizoma contain tryptophan and isovitexin.

Ziziphi Spinosae Semen and Licorice include isoquercitrin and vicenin II. Ziziphi Spinosae Semen and Poria contain ursolic acid. Anemarrhenae rhizoma and Licorice contain only one component mangiferin (Figure 2(a)).

In SZRD, Ziziphi Spinosae Semen seed is “Jun” (the monarch). There are 175 chemical compounds in Ziziphi Spinosae Semen seed, accounting for 15.8% in all 5 herbs (Figure 2(b)). When compared with total compounds in the other four herbs, there are 9 common compounds with 0.8% of total compounds in all 5 herbs, including adenosine, tryptophan, isoquercitrin, isovitexin, vicenin II, linoleic acid, oleic acid, protocatechuic acid and ursolic acid (Figure 2(b)).

4.2. Comparative Analysis of Chemical Constituents between Suanzaoren Decoction and Herbs4.2.1. Ingredients between Suanzaoren Decoction and Herbs

After comparing 145 compounds in SZRD with 1104 in 5 herbs, We found there were 80 common components which accounted for 6.8% of total compounds in all herbs and 55.2% of compounds in SZRD (Figure 3(a)), containing 7 categories, including 27 flavonoids, 17 triterpenoids, 12 steroids, 5 volatile oils, 4 coumarins, 14 phenolic acids and 1 alkaloid (Figure 3(b)) and found that 14 compounds came from Ziziphi Spinosae Semen, 18 from Chuanxiong Rhizoma, 15 from Anemarrhenae rhizoma, 9 from Poria and 27 from Licorice.

In addition, 65 compounds in SZRD are not contained in Ziziphi Spinosae Semen, Anemarrhenae rhizoma, Chuanxiong Rhizoma, Poria and Licorice (Figure 3(c)). These distinctive compounds account for 5.6% of total compounds in all herbs and 44.8% of SZRD compounds (Figure 3(a)), and include alkaloids (1 compound), coumarins (3 compounds), flavonoids (25 compounds), phenolic acids (1 compound), phthalides (2 compounds), polysaccharides (1 compound), steroids (7 compounds), triterpenoids (17 compounds), volatile oils (3 compounds) and others (5 compounds). The number of flavonoids is the highest among SZRD, followed by triterpenoids, suggesting ingredients of SZRD are not simply the sum of the single ingredients and new compounds will produce after decocting SZRD.

The amounts of volatile oils, alkaloids and polysaccharides are decreased while the number of flavonoids is increased in SZRD compared with 5 single herbs (Figure 4(a) and Figure 4(b)). In general, there are many water-soluble compounds in SZRD, such as flavonoids, triterpenoids, accounting for 59.31%. However, triterpenoids, flavonoids and volatile oils account for 22.95%, 18.24% and 15.93% respectively in 5 single herbs. Amino acids, ceramides and cerebrosides, lignans, nucleotides, steroids and stilbenides are not found in SZRD. We inferred it might due to the extraction of SZRD just exists in aqueous decoction, the proportion of components with larger polarity is significantly increased, while the proportion of components with weak polarity is relatively low. On the other hand, it may because the lack of literature on the components of SZRD, and the literatures are just for the analysis of specific components and lack researches on specific components.

4.2.2. Ingredients between Suanzaoren Decoction and Ziziphi Spinosae Semen

We compared 145 compounds contained in SZRD with 175 in Ziziphi Spinosae Semen, the monarch of SZRD (Figure 4(c)). There are 14 common components,

accounting for 9.7% in SZRD, which are flavonoids (6'''-Feruloylspinosin, glucosylvitexin, isovitexin, nicotiflorin, saponarin, spinosin, wertisin, vicenin II), triterpenoids (betulinic acid, jujuboside A, jujuboside B, oleanolic acid), alkaloid (magnoflorine) and volatile oil (palmitic acid), while it has 131 different

compounds (90.3%) (Figure 4(c)), including flavonoids (45 compounds), alkaloid (1 compound), coumarins (7 compounds), phenolic acids (4 compounds), phthalides (14 compounds), triterpenoids (29 compounds), steroids (19 compounds), volatile oils (6 compounds), polysaccharide (1 compound) and others (5 compounds) (Figure 4(a) and Figure 4(b)).

5. Summary and Perspectives

In SZRD, Ziziphi Spinosae Semen is the monarch drug, Chuanxiong Rhizoma and Poria are minister drugs, Anemarrhenae rhizoma is an adjuvant, Licorice is conductant drug, which can reconcil various drugs. Totally, we collected 145 and 1104 chemical ingredients in SZRD and its five-single herbs respectively and found 80 common ingredients between SZRD and five-single herbs, while 65 different compounds only in SZRD. Taken together, our study elucidated that components of SZRD were not simply the sum of one in every single herb. Based on the analysis of the relationship of ingredients between five-single herbs and the whole prescription, we found that the problems existed in the chemical research of SZRD and possible further research direction.

5.1. What Has Already Been Shown to Be Not Promising

1) As the chemical profile of the decoction is dependent on the quality of the plant materials, each compound probably was a wide range of concentrations. Therefore, we highlighted names, numbers and variabilities of compounds in the five herbs and SZRD, nothing is said about the quantities or actual concentrations of these compounds in this review.

2) As different methods have been used, it will be difficult to compare the results of the various studies. There was an effect of the experimental conditions on the overall extracted chemical profile of the decoction. It may be different conditions and time of soaking and decocting, different extraction solvents, different apparatus and parameters to identify SZRD and five-single herbs. That means this number of compounds is very much based on the sensitivity and selectivity of the methods of analysis. For example, the compounds mentioned represent a wide range of polarities, and many of them from five-single herbs will probably not being extraction extracted in SZRD.

3) The variability in the raw materials had an effect on the plant materials on the overall extracted chemical profile of the decoction. For example, the different local growing environments of plants.

4) The different understanding of researchers on the compounds, and global chemical components had an effect on compound being obtained and identified in herbs.

5) It is unbalanced at present of the studies among Ziziphi Spinosae Semen, Chuanxiong Rhizoma, Anemarrhenae rhizoma, Poria, Licorice and SZRD, that mean there were more compounds in herbs with many reports than that with few reports. It was lack of global chemical components for each herb and SZRD.

5.2. What Looks Promising

1) As SZRD is composed of Ziziphi Spinosae Semen, Chuanxiong Rhizoma, Anemarrhenae rhizoma, Poria, Licorice, it is necessary to perform parallel studies among SZRD and its herbs.

2) As pharmacological activity has a dose-response curve, moreover synergy and antagonistic effect may occur between compounds in certain ratios, it is the biological activity of the individual compounds and their concentration that determine the activity of the final preparation. Therefore, it is necessary to study phytochemistry and pharmacological activities at the same time.

3) What is needed is to integrate the data on activity of extracts and pure compounds with the data on traditional use and the data on the chemistry.

5.3. The Limitations of This Article

1) Compounds collection of SZRD and five-single herbs were mainly based on the literature in the past five years, but few had been reported more than five years.

2) This paper did not carry out a classification analysis for non-English name compounds.

3) For the chemical composition of SZRD and its five-single herbs, we just simply classified them based on their chemical structures while not carrying out subcategory analysis.

Although these results are exploratory and need to be interpreted with caution, our study provides important information that may help offer subsequent studies to determine the compounds and explore pharmacology research about SZRD. This review may provide the reference for phytochemistry and pharmacology researches of SZRD, and also point out the direction for its further research.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 81974555).

Consent for Publication

All authors have given consent for publication.

Competing interests

The authors declare that they have no competing interests.

Cite this paper

Gu, W.C., Ye, T.Y., Zhang, L.K., Yang, Y., Qi, D.M., Cheng, X.R. and Wang, X. (2021) A Systematic Review on Chemical Constituents of Suanzaoren Decoction, a Traditional Chinese Medicine Prescription. International Journal of Clinical Medicine, 12, 494-523. https://doi.org/10.4236/ijcm.2021.1211045

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