Polygonum capitatum Buch.-Ham. ex D. Don: a review of its phytochemistry

Abstract

Polygonum capitatum (Polygonaceae) exists in rural areas of Southwest China and some other Asian countries. Its aerial part or whole herbal plant has been used as a Miao ethnomedicine against urinary system diseases, infections, pyelonephritis, diarrhea, and so on. The progress in phytochemical research on P. capitatum over the past decades is summarized. Two hundred and three chemical constituents that have been isolated and identified from this plant are included in this article, the chemical structures of which include aliphatic hydrocarbons, aliphatic alcohols, aliphatic ketones, aromatic aldehydes, aliphatic acids, glycerides, triterpenic acids, sterols, anthraquinones, chromones and their glycosides, flavonoids and their glycosides, phenols, phenolic acids and their esters, lignanoids, flavonolignans, phenolic glycosides, alcoholic glycosides, amino acids, nucleobases, amides, alkaloids, alkyl glycosides, volatile oils, and polysaccharides.

Keywords:
Polygonum capitatum; Polygonaceae; phytochemistry; chemical constituents

1 Introduction

Polygonum capitatum Buch.-Ham. ex D. Don (Polygonaceae) exists in rural areas of Southwest China and some other Asian countries such as India, Nepal, Bhutan, Burma and Vietnam (Editorial Committee of Chinese Academy of Sciences, 1998). The Chinese names of this perennial herb include “Touhualiao”, “Sijihong”, “Shijiaocao”. The whole plant and the capitate inflorescence of P. capitatum are shown in Figure 1. Its aerial part or whole herbal plant (Figure 2) has been used as a Miao ethnomedicine against urinary system diseases and other diseases, including infections, pyelonephritis, urocystitis, urolithiasis, hematuria, rheumatalgia, dysentery, and diarrhea (Nanjing University of Traditional Chinese Medicine, 2006; Pharmaceutical Administration of Guizhou Province, 2003; Ren et al., 1995). The local inhabitants often eat P. capitatum on its own as wild vegetables or serve steamed with lean meat (Nanjing University of Traditional Chinese Medicine, 2006; Zhong, 2001). Its leaves and stems can be used as folk dietary medicine (Huang et al., 2008). Relinqing granules, tablets and capsules (Figure 3), which are prepared from P. capitatum and approved by the Chinese Food and Drug Administration (Zhang et al., 2013a), not only have the efficacy of “clearing away heat”, “reducing fire”, “dredging stranguria”, and diuresis, but also are used to treat frequent and urgent urination, dysuria, urinary tract infections and pyelonephritis (National Pharmacopoeia Committee, 2020). Relinqing series preparations have been the best-selling Chinese patent medicines on the market to treat urinary system diseases.

Figure 1
The whole plant and the capitate inflorescence of P. capitatum.

Figure 2
The dried medicinal materials of P. capitatum.

Figure 3
Chinese patent medicines: Relinqing granules, tablets and capsules.

Research had showed that the chemical constituents of P. capitatum include sterols, triterpenes, alkaloids, lignans, flavonoids, phenolic acids (Chen et al., 2010b; Gao et al., 2001; Li et al., 2000, 2007; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Yang et al., 2011, 2015b; Yu et al., 2008; Zhang et al., 2010; Zhao et al., 2010), and other volatile oils (Gao et al., 2005; Wang et al., 2007) and liposoluble compounds (Yang et al., 2009, 2011). Flavonoids and phenolic acids were potentially major active constituents (Zhang et al., 2013a; Zhao et al., 2020). Gallic acid was considered as the best standards as the spectrophotometric response of these compounds were equivalent to most other phenolic acids compounds (Wabaidur et al., 2020). So gallic acid had been used as a marker compound for quality control of Relinqing granules in Chinese Pharmacopoeia (National Pharmacopoeia Committee, 2020).

Reported pharmacological effects of the extracts of P. capitatum included analgesis, diuresis (Liu et al., 2007), antioxidation (Huang et al., 2008; Liu et al., 2008; Yan et al., 2010), anti-bacterium (Liao et al., 2011), anti-inflammation (Liao et al., 2011; Zhang et al., 2015), α-glucosidase inhibition (Chen et al., 2010a), antitumor activity (Fu et al., 2012; He et al., 2014; Ma et al., 2014; Wang et al., 2014), and increased activities of CYP2C9 and CYP3A4 (Zheng et al., 2014). Flavonoids and phenolic acids showed antioxidant activity while quercetin, quercitroside and kaempferol were potent enough to clear active oxygen free radicals (Liu et al., 2008). Flavonoids were mentioned to be associated with α-glucosidase inhibition activity (Syabana et al., 2021). Phenolic acids had been shown to have a functional role due to their high antioxidant activity, that prevented oxidative damages (Hartwig et al., 2020). Chemical fractions rich in flavonoids and tannins possessed bacteriostatic and bactericidal properties, while those rich in triterpenoids, steroids, and flavonoids exhibited anti-inflammatory activity (Liao et al., 2011). Flavonol glycosides showed the effect of repairing gastric injury (Zhang et al., 2015). A lignanoid named (−)-lyoniresinol-9′-O-[6-O-(4-hydroxy-3,5-dimethoxy)-benzoyl]-β-D-glucopyranoside exhibited strong α-glucosidase inhibitory activity (Ye et al., 2017). An ellagitannin named davidiin could inhibit hepatocellular tumor growth both in vitro and in vivo by targeting the enhancer of zeste homolog 2 (EZH2) and warranted further clinical investigation as a potential anti-hepatocellular carcinoma agent (Wang et al., 2014).

So far, about, 203 chemical constituents have been isolated and identified from P. capitatum. The chemical structures include aliphatic hydrocarbons, aliphatic alcohols, aliphatic ketones, aromatic aldehydes, aliphatic acids, glycerides, triterpenic acids, sterols, anthraquinones, chromones and their glycosides, flavonoids and their glycosides, phenols, phenolic acids and their esters, lignanoids, flavonolignans, phenolic glycosides, alcoholic glycosides, amino acids, nucleobases, amides, alkaloids, alkyl glycosides, volatile oils, and polysaccharides. The types of their structures, chemical names, molecular formulas, and parts of the plant from which they were isolated are listed in Table 1. Their chemical structures are shown in Figure 4.

Table 1
Chemical constituents isolated from P. capitatum.

No.	Structure type and chemical name	Molecular formula	Isolation Part	References
	Aliphatic hydrocarbons and aliphatic alcohols
1	tricosane	C23H48	W	Gao et al., 2005; Yang et al., 2009
2	octacosa-1,27-diene	C28H54	W	Yang et al., 2009
3	phytol	C20H40O	A,U	Wang et al., 2007; 2013
4	tricosanol	C23H48O	W	Yang et al., 2009
5	pentacosanol	C25H52O	W	Yang et al., 2009
6	tetracosane-1,3-diol	C24H50O2	W	Yang et al., 2011
	Aliphatic ketones and aromatic aldehydes
7	24-hydroxy-tetracosanone-3	C24H48O2	W	Wu & Wang, 1985
8	29-hydroxy-nonacosanone-3	C29H58O2	W	Wu & Wang, 1985
9	benzaldehyde	C7H6O	W,U	Wang et al., 2007; Wu & Wang, 1985
10	5-hydroxymethyl furfural	C6H6O3	A	Yu et al., 2008
	Aliphatic acids
11	acetic acid	C2H4O2	W	Wu & Wang, 1985
12	succinic acid	C4H6O4	A	Yu et al., 2008
13	linoleic acid	C18H32O2	W	Wang et al., 2007; Yang et al., 2009
14	hexadecanoic acid	C16H32O2	W	Wang et al., 2007; Yang et al., 2009
15	docosanoic acid	C22H44O2	W	Yang et al., 2009
16	tetracosanoic acid	C24H48O2	W	Yang et al., 2009
	Glycerides
17	hexadecanoic-2,3-dihydroxypropylester	C19H38O4	W	Yang et al., 2009
18	docosanoic-2,3-dihydroxypropylester	C25H50O4	W	Yang et al., 2009
19	1-[(E,E)-12,16-eicosadienoyl]-2-[(E,E)-7,11-octadecadienoyl]-3-stearoylglycerol	C59H106O6	A	Wang et al., 2013
	Triterpenic acids and sterols
20	oleanolic acid	C30H48O3	W	Huang et al., 2015; Yang et al., 2009
21	ursolic acid	C30H48O3	W	Huang et al., 2015; Yang et al., 2009
22	β-sitosterol	C29H50O	A,W	Chen et al., 2011; Liu et al., 2008; Wang et al., 2013; Wu & Wang, 1985; Yang et al., 2009
23	daucosterol	C35H60O6	A,W	Chen et al., 2011; Liu et al., 2008; Wang et al., 2013; Yang et al., 2011, 2015b; Zhao et al., 2011
24	24-methylenecycloartenol	C31H52O	A	Wang et al., 2013
25	(24R)-cycloart-25-ene-3β,24-diol	C30H50O2	W	Yang et al., 2011
	Anthraquinones
26	emodin	C15H10O5	W	Huang et al., 2015; Yang et al., 2011, 2015b
27	1,5,7-trihydroxyl-3-methylanthraquinone	C15H10O5	A	Yu et al., 2008
28	1,3,8-trihydroxyl-6-methylanthraquinone-1-O-[4-hydroxy-E-cinnamoyl-(→2)]-β-D-glucopyranoside	C30H26O12	W	Yao et al., 2018
	Chromones and their glycosides, flavonoids and their glycosides
29	5,7-dihydroxy-4H-chromen-4-one	C9H6O4	A,W,U	Liao et al., 2013; Wang et al., 2013; Zhang et al., 2010; 2012
30	5,7-dihydroxychromone-7-O-glucopyranoside	C15H16O9	W	Liao et al., 2013
31	7-O-(6′-galloyl)-β-D-glucopyranosyl-5-hydroxychromone	C22H20O13	A,W	Chen et al., 2011; Li et al., 2007; Liao et al., 2012, 2013
32	sawarachromone	C15H14O7	W	Liao et al., 2013
33	luteolin	C15H10O6	A,W	Jing et al., 2015; Zhang et al., 2013b
34	luteolin-7-O-glucoside	C21H20O11	W	Wang & Jiang, 2018
35	daidzin	C21H20O9	W	Jing et al., 2015
36	naringenin-7-O-glucopyranoside	C21H22O10	W	Liao et al., 2013
37	2,7,4′-trihydroxyflavanone-5-O-β-D-glucopyranoside	C21H22O11	W	Yang et al., 2017b
38	kaempferol	C15H10O6	A,W	Jing et al., 2015; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Yang et al., 2015b; Yu et al., 2008; Zhang et al., 2012, 2013a; b
39	kaempferol-3-O-α-L-rhamnopyranoside	C21H20O10	S,L,A,W	Huang et al., 2008, 2015; Liao et al., 2013; Wang et al., 2013; Yang et al., 2015b; Zhang et al., 2012
40	kaempferol-3-O-β-D-glucopyranoside	C21H20O11	A,W	Huang et al., 2015; Liao et al., 2013; Wang et al., 2013; Yang et al., 2015b
41	kaempferol-3-O-galactoside	C21H20O11	W	Liao et al., 2013
42	kaempferol-4′-O-rutinoside	C27H30O15	W	Liao et al., 2013
43	quercetin	C15H10O7	A,W,U	Huang et al., 2015; Jing et al., 2015; Li et al., 2000; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Yang et al., 2015b; Yu et al., 2008; Zhang et al., 2010; 2012; 2013a; b; Zhao et al., 2011; Zheng et al., 2014
44	quercetin 3-methyl ether	C16H12O7	A,W	Huang et al., 2015; Liao et al., 2013; Wang et al., 2013
45	quercetin-3-O-arabinoside	C20H18O11	S,L,W	Huang et al., 2008; Liao et al., 2013; Yao et al., 2018
46	quercetin-3-O-xyloside	C20H18O11	W	Liao et al., 2013
47	quercitroside	C21H20O11	S,L,A,W,U	He et al., 2014; Huang et al., 2008; 2015, 2019; Jing et al., 2015; Li et al., 2000, 2007; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Wang & Jiang, 2018; Yang et al., 2008; 2015a; b; Yao et al., 2018; Yu et al., 2008; Zhang et al., 2010, 2012; 2013a; b; Zhao et al., 2011; Zheng et al., 2014; Zhou et al., 2017
48	4″-methoxy quercitroside	C22H22O11	W	Huang et al., 2015
49	4″-O-acetyl quercitroside	C23H22O12	W	Liao et al., 2012; 2013; Zhao et al., 2011
50	quercetin-3-O-(2″-O-protocatechuoyl)-L-rhamnopyranoside	C28H24O14	W	Liao et al., 2012; 2013
51	2″-O-galloyl quercitroside	C28H24O15	A,W,U	Wang et al., 2013; Yang et al., 2015b; Huang et al., 2015; Liao et al., 2012, 2013; Li et al., 2000; Yao et al., 2018; Zhang et al., 2010; 2012; Zhao et al., 2011; Zhou et al., 2017
52	3″-O-galloyl quercitroside	C28H24O15	W	Liao et al., 2012; 2013; Zhang et al., 2012
53	isoquercitrin	C21H20O12	S,L,W,U	Huang et al., 2008; 2015; Li et al., 2000; Liao et al., 2013; Liu et al., 2008; Yang et al., 2015b; Yao et al., 2018; Zhang et al., 2010; 2012; Zheng et al., 2014; Zhou et al., 2017
54	quercetin-3-O-β-D-glucuronide	C21H18O13	S,L	Huang et al., 2008
55	2″-O-galloyl isoquercitrin	C28H24O16	A,W	Huang et al., 2015; Liao et al., 2012, 2013; Wang et al., 2013; Yang et al., 2015b; Yao et al., 2018; Zhang et al., 2012; Zhou et al., 2017
56	3″-O-galloyl isoquercitrin	C28H24O16	W	Liao et al., 2012; 2013; Zhang et al., 2012
57	quercetin-3-O-(2″-O-trans-p-coumaroyl)glucopyranoside	C30H26O14	W	Liao et al., 2012; 2013
58	quercetin-3-O-β-D-galactopyranoside	C21H20O12	W	Liao et al., 2013; Yang et al., 2015a
59	quercetin-3-O-(2″-O-trans-p-coumaroyl)galactopyranoside	C30H26O14	W	Liao et al., 2012; 2013
60	quercetin-3-O-(6″-O-trans-feruloyl)-β-D-galactopyranoside	C31H28O15	A	Wang et al., 2013
61	rutin	C27H30O16	A,W,U	Jing et al., 2015; Liao et al., 2013; Wang & Jiang, 2018; Zhang et al., 2010; 2012, 2013b
62	myricitrin	C21H20O12	A,W	Jing et al., 2015; Liao et al., 2013; Wang et al., 2013; Yang et al., 2015a; Zhang et al., 2012; Zhao et al., 2011; Zheng et al., 2014
63	3,3′,4′,5,5′,7-hexahydroxyflavone-3-O-(5-O-acetyl-L-arabinoside)	C22H20O13	W	Yao et al., 2018
64	3′-hydroxy-3,4′,5,5′,8-pentamethoxy-6,7-methylene dioxyflavone	C21H20O10	W	Yao et al., 2018
65	3′,4′-methylenedioxy-3,5,6,7,8,5′-hexamethoxyflavone	C22H22O10	W	Gao et al., 2001
66	viviparum B	C23H22O12	W	Yao et al., 2018; Zhou et al., 2017
67	taxifolin	C15H12O7	W	Huang et al., 2015
68	(−)-epicatechin	C15H14O6	W	Yang et al., 2015b
69	(+)-catechin	C15H14O6	A,W	Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b; Yao et al., 2018; Zhang et al., 2013a, b; Zhou et al., 2017
70	(−)-epicatechin-3-O-gallate	C22H18O10	W	Huang et al., 2015; Zhou et al., 2017
71	(+)-catechin-3-O-gallate	C22H18O10	W	Yang et al., 2015b
72	(−)-epicatechin-(2β→O→7,4β→8)-(+)-catechin (procyanidin A1)	C30H24O12	W	Yang et al., 2015b
73	3-galloyl-(−)-epicatechin-(4β→8)-3-galloyl-(−)-epicatechin (3,3″-digalloylprocyanidin B2)	C44H34O20	W	Yao et al., 2018; Zhou et al., 2017
	Phenols, phenolic acids and their esters
74	catechol	C6H6O2	U	Zhang et al., 2010
75	p-hydroxybenzoic acid	C7H6O3	A	Wang et al., 2013
76	gentisic acid	C7H6O4	W	Jing et al., 2015
77	protocatechuic acid	C7H6O4	A,W,U	Chen et al., 2011; Huang et al., 2019; Jing et al., 2015; Li et al., 2007; Liao et al., 2013; Liu et al., 2008; Yang et al., 2015a, b; Yu et al., 2008; Zhang et al., 2010, 2013a,b; Zhao et al., 2011; Zheng et al., 2014
78	vanillic acid	C8H8O4	A	Chen et al., 2011; Li et al., 2007; Yu et al., 2008; Zhang et al., 2013a, b
79	ethyl protocatechuate	C9H10O4	A,U	Wang et al., 2013; Yu et al., 2008; Zhang et al., 2010
80	gallic acid	C7H6O5	S,L,A,W,U	Chen et al., 2010b, 2011; Huang et al., 2008, 2019; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Wu & Wang, 1985; Yang et al., 2008,2015a,b; Yu et al., 2008; Zhang et al., 2010; 2013a,b; Zhao et al., 2011; Zheng et al., 2014; Zhou et al., 2017
81	3,5-dihydroxy-4-methoxybenzoic acid	C8H8O5	W,U	Liao et al., 2013; Zhang et al., 2010
82	syringic acid	C9H10O5	A,U	Zhang et al., 2010, 2013a,b
83	methyl gallate	C8H8O5	A,W	Jing et al., 2015; Zhang et al., 2013b
84	ethyl gallate	C9H10O5	A,W,U	Huang et al., 2015; Liu et al., 2008; Wang et al., 2013; Yang et al., 2015b; Yu et al., 2008; Zhang et al., 2010, 2013b; Zhao et al., 2011
85	ellagic acid	C14H6O8	A,W	Liao et al., 2013; Wang et al., 2013; Zhang et al., 2012; Zhou et al., 2017
86	3,3′-di-O-methylellagic acid	C16H10O8	W	Liao et al., 2013; Zhou et al., 2017
87	brevifolin	C12H8O6	A	Wang et al., 2013
88	brevifolin carboxylic acid	C13H8O8	U	Chen et al., 2010b
89	ethyl brevifolin carboxylate	C15H12O8	A	Wang et al., 2013
90	3-O-galloyl-α-D-glucopyranoside	C13H16O10	W	Yang et al., 2015b
91	3-O-galloyl-β-D-glucopyranoside	C13H16O10	W	Yang et al., 2015b
92	6-O-galloyl-D-glucopyranoside	C13H16O10	W	Yao et al., 2018
93	3,6-O-digalloyl-D-glucopyranoside	C20H20O14	W	Yao et al., 2018; Zhou et al., 2017
94	1,3,6-O-trigalloyl-D-glucopyranoside	C27H24O18	W	Yao et al., 2018
95	1,3-di-O-galloyl-4,6-O-(S)-hexahydroxy-diphenoyl-β-D-glucopyranoside	C34H26O22	W	Yao et al., 2018; Zhou et al., 2017
96	davidiin	C41H30O26	W	Fu et al., 2012; He et al., 2014; Ma et al., 2014; Wang et al., 2014; Yang et al., 2008; Yao et al., 2018; Zhou et al., 2017
97	trans-p-coumaric acid	C9H8O3	W	Liao et al., 2013
98	docosyl ferulate	C32H54O4	W	Yang et al., 2009
99	tetracosyl ferulate	C34H58O4	W	Liu et al., 2008
100	chlorogenic acid	C16H18O9	S,L	Huang et al., 2008
101	helonioside A	C32H38O17	W	Yao et al., 2018; Zhou et al., 2017
102	6-acetyl-3′,6′-O-diferuloylsucrose (helonioside B)	C34H40O18	W	Zhou et al., 2017
103	bistoroside B	C34H40O18	W	Liao et al., 2013
	Lignanoids and flavonolignans
104	(+)-isolariciresinol	C20H24O6	W	Ye et al., 2017
105	schizandriside	C25H32O10	A,W	Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b; Yao et al., 2018; Zhang et al., 2013a, b; Zhao et al., 2010; Zhou et al., 2017
106	5′-methoxy-(+)-isolariciresinol-9′-O-β-D-xylopyranoside	C26H34O11	W	Huang et al., 2015; Ye et al., 2017
107	lyoniside	C27H36O12	W	Ye et al., 2017
108	(+)-isolariciresinol-9′-O-β-D-glucopyranoside	C26H34O11	W	Huang et al., 2015
109	(+)-lyoniresinol-9′-O-β-D-glucopyranoside	C28H38O13	W	Zhou et al., 2017
110	(−)-isolariciresinol	C20H24O6	W	Huang et al., 2015
111	(−)-isolariciresinol-9′-O-β-D-xylopyranoside	C25H32O10	W	Yang et al., 2015b; Ye et al., 2017; Zhao et al., 2010
112	5′-methoxy-(−)-isolariciresinol-9′-O-β-D-xylopyranoside	C26H34O11	W	Yang et al., 2015b; Zhao et al., 2010
113	nudiposide	C27H36O12	W	Huang et al., 2015; Yang et al., 2015b; Yao et al., 2018; Ye et al., 2017; Zhao et al., 2010; Zhou et al., 2017
114	(−)-isolariciresinol-9′-O-β-D-glucopyranoside	C26H34O11	W	Ye et al., 2017
115	(−)-lyoniresinol-9′-O-[6-O-(4-hydroxy-3,5-dimethoxy)-benzoyl]-β-D-glucopyranoside	C37H46O17	W	Ye et al., 2017
116	silibinin	C25H22O10	W	Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b
117	2,3-dehydrosilibinin	C25H20O10	W	Huang et al., 2015; Yang et al., 2015b
118	silychristin	C25H22O10	W	Yang et al., 2015b
119	2,3-dehydrosilychristin	C25H20O10	W	Huang et al., 2015; Yang et al., 2015b
	Phenolic glycosides
120	arbutin	C12H16O7	W	Huang et al., 2015; Yang et al., 2017b
121	3-methoxyl-4-hydroxyphenol-1-O-β-D-glucopyranoside (tachioside)	C13H18O8	W	Huang et al., 2015; Yang et al., 2017b
122	3-methoxyl-4-hydroxyphenol-1-O-β-D-(6′-O-galloyl)glucopyranoside	C20H22O12	W	Yang et al., 2017b
123	2-methoxyl-4-hydroxyphenol-1-O-β-D-glucopyranoside (isotachioside)	C13H18O8	W	Huang et al., 2015; Yang et al., 2017b
124	2-methoxyl-4-hydroxyphenol-1-O-β-D-(6′-O-galloyl)glucopyranoside	C20H22O12	W	Yang et al., 2017b
125	3,5-dimethoxyl-4-hydroxyphenol-1-O-β-D-glucopyranoside	C14H20O9	W	Huang et al., 2015; Yang et al., 2017b
126	3,4,5-trimethoxylphenol-1-O-β-D-glucopyranoside	C15H22O9	W	Yang et al., 2017b
127	3-methoxyl-5-hydroxyphenol-1-O-β-D-glucopyranoside (picraquassioside D)	C13H18O8	W	Huang et al., 2015; Yang et al., 2017b
128	3-methoxyl-5-hydroxyphenol-1-O-β-D-(6′-O-galloyl)glucopyranoside	C20H22O12	W	Liao et al., 2012, 2013; Zhang et al., 2012
129	3-methoxyl-5-hydroxyphenol-1-O-β-D-(6′-O-galloyl)galactopyranoside	C20H22O12	W	Liao et al., 2012, 2013
	Alcoholic glycosides
130	benzyl-O-β-D-glucopyranoside	C13H18O6	W	Yang et al., 2017b
131	salidroside	C14H20O7	W	Huang et al., 2015; Yang et al., 2017b
132	β-D-glucopyranosyl-12-hydroxyjasmonic acid	C18H28O9	W	Yang et al., 2017b
133	β-D-glucopyranosyl-12-hydroxy-12-(2″-hydroxy-2″-carboxyethyl)jasmonic acid	C21H32O12	W	Yang et al., 2017b
	Amino acids, nucleobases, amides and alkaloids
134	L-phenylalanine	C9H11NO2	W	Jing et al., 2015; Liao et al., 2013
135	L-tryptophan	C11H12N2O2	W	Yang et al., 2017b
136	uracil	C4H4N2O2	W	Jing et al., 2015
137	N-trans-caffeoyltyramine	C17H17NO4	A	Wang et al., 2013
138	N-cis-feruloyltyramine	C18H19NO4	W	Liao et al., 2013
139	flazine	C17H12N2O4	A	Wang et al., 2013
	Alkyl glycosides
140	2-O-butyl-α-D-fructofuranoside	C10H20O6	W	Yang et al., 2011, 2017a
141	2-O-butyl-β-D-fructofuranoside	C10H20O6	W	Yang et al., 2011, 2017a
142	2-O-butyl-β-D-fructopyranoside	C10H20O6	W	Yang et al., 2017a
143	3-O-butyl-β-D-fructopyranoside	C10H20O6	W	Yang et al., 2017a
144	1-O-butyl-α-D-glucofuranoside	C10H20O6	W	Yang et al., 2017a
145	1-O-butyl-β-D-glucofuranoside	C10H20O6	W	Yang et al., 2017a
146	1-O-butyl-β-D-glucopyranoside	C10H20O6	W	Yang et al., 2017a
147	1-O-butyl-β-D-mannopyranoside	C10H20O6	W	Yang et al., 2011
	Volatile oils
148	trans-β-farnesene	C15H24	W	Gao et al., 2005
149	1-hexanol	C6H14O	W	Gao et al., 2005
150	3-octanol	C8H18O	W	Gao et al., 2005
151	(E)-2-octen-1-ol	C8H16O	W	Gao et al., 2005
152	1-octen-3-ol	C8H16O	W	Gao et al., 2005
153	(Z)-1,5-octadien-3-ol	C8H14O	W	Gao et al., 2005
154	nerolidol	C15H26O	W	Gao et al., 2005
155	heptanal	C7H14O	W	Gao et al., 2005
156	n-octanal	C8H16O	W	Gao et al., 2005
157	nonanal	C9H18O	W	Gao et al., 2005
158	2-hexenal	C6H10O	W	Gao et al., 2005
159	(E)-2-heptenal	C7H12O	W	Gao et al., 2005
160	(E)-2-octenal	C8H14O	W	Gao et al., 2005
161	(E,E)-2,4-heptadienal	C7H10O	W	Gao et al., 2005
162	2-heptanone	C7H14O	W	Gao et al., 2005
163	6-methyl-5-hepten-2-one	C8H14O	W	Gao et al., 2005
164	1-octen-3-one	C8H14O	W	Gao et al., 2005
165	2,3-octanedione	C8H14O2	W	Gao et al., 2005
166	6,10,14-trimethyl-2-pentadecanone	C18H36O	W,U	Gao et al., 2005; Wang et al., 2007
167	p-xylene	C8H10	W	Gao et al., 2005
168	anthracene	C14H10	W	Gao et al., 2005
169	2-pentyl-furan	C9H14O	W	Gao et al., 2005
170	hyacinthin	C8H8O	W	Gao et al., 2005
171	2,2,6-trimethyl-cyclohexanone	C9H16O	W	Gao et al., 2005
172	β-cyclocitral	C10H16O	W	Gao et al., 2005
173	precocene I	C12H14O2	W	Gao et al., 2005
174	β-costol	C15H24O	W	Gao et al., 2005
175	γ-costol	C15H24O	W	Gao et al., 2005
176	m-menthe-1,8-diene	C10H16	W	Gao et al., 2005
177	limonene	C10H16	W	Gao et al., 2005
178	α-terpinolene	C10H16	W	Gao et al., 2005
179	terpinene-4-ol	C10H18O	W	Gao et al., 2005
180	α-terpineol	C10H18O	W,U	Gao et al., 2005; Wang et al., 2007
181	1-menthol	C10H20O	W	Gao et al., 2005
182	o-cymene	C10H14	W	Gao et al., 2005
183	carvacrol	C10H14O	W	Gao et al., 2005
184	α-pinene	C10H16	W	Gao et al., 2005
185	nopinone	C9H14O	W	Gao et al., 2005
186	myrtenal	C10H14O	W	Gao et al., 2005
187	camphene	C10H16	W,U	Gao et al., 2005; Wang et al., 2007
188	L-borneol	C10H18O	W	Gao et al., 2005
189	1,8-cineole	C10H18O	W	Gao et al., 2005
190	camphore	C10H16O	W	Gao et al., 2005
191	β-caryophyllene	C15H24	W	Gao et al., 2005
192	δ-cadinene	C15H24	W	Gao et al., 2005
193	γ-gurjunene	C15H24	W	Gao et al., 2005
194	longiborneol	C15H26O	W	Gao et al., 2005
195	globulol	C15H26O	W	Gao et al., 2005
196	lauric acid	C12H24O2	U	Wang et al., 2007
197	myristic acid	C14H28O2	U	Wang et al., 2007
198	pentadecanoic acid	C15H30O2	U	Wang et al., 2007
199	oleic acid	C18H34O2	U	Wang et al., 2007
200	methyl-9-octadecenoate	C19H36O2	U	Wang et al., 2007
201	methyl linoleate	C19H34O2	U	Wang et al., 2007
202	methyl linolenate	C19H32O2	U	Wang et al., 2007
203	tetracosane	C24H50	W	Gao et al., 2005

• Notes: S, stem; L, leave; A, aerial parts; W, whole plant; U, undescribed.

Figure 4
Structures of chemical constituents of P. capitatum. Notes: Ara, arabinoside; Xyl, xyloside; Rha, rhamnoside; Glu, glucoside; Gal, galactoside; Rut, rutinoside.

2 Results and discussions

Two aliphatic hydrocarbons (1,2) (Gao et al., 2005; Yang et al., 2009), four aliphatic alcohols (3−6) (Wang et al., 2007, 2013; Yang et al., 2009, 2011), two aliphatic ketones (7,8) (Wu & Wang, 1985), two aromatic aldehydes (9,10) (Wang et al., 2007; Wu & Wang, 1985; Yu et al., 2008), six aliphatic acids (11−16) (Wang et al., 2007; Wu & Wang, 1985; Yang et al., 2009; Yu et al., 2008), and three glycerides (17−19) (Wang et al., 2013; Yang et al., 2009) were identified from the aerial parts or whole plant of P. capitatum. All were isolated from petroleum ether extracts.

Two pentacyclic triterpenic acids, which are named oleanolic acid (20) (Huang et al., 2015; Yang et al., 2009) and ursolic acid (21) (Huang et al., 2015; Yang et al., 2009) are of the oleanane type and ursane type of triterpenes respectively, were found from the whole plant of P. capitatum. Four sterols (22−25) (Chen et al., 2011; Liu et al., 2008; Wang et al., 2013; Wu & Wang, 1985; Yang et al., 2009, 2011, 2015b; Zhao et al., 2011) were isolated from the aerial parts and whole plant. β-Sitosterol (22) and daucosterol (23) are extremely common in higher plants. Isolation of (24R)-cycloart-25-ene-3β,24-diol (25) from Polygonaceae was reported for the first time in, 2011 (Yang et al., 2011). Three anthraquinones (26−28) (Huang et al., 2015; Yang et al., 2011, 2015b; Yao et al., 2018; Yu et al., 2008) were isolated from P. capitatum.

Four chromones (29−32) (Chen et al., 2011; Li et al., 2007; Liao et al., 2012, 2013; Wang et al., 2013; Zhang et al., 2010, 2012), namely benzo-γ-pyron compounds, were obtained from P. capitatum. 7-O-(6′-Galloyl)-β-D-glucopyranosyl-5-hydroxychromone (31) (Chen et al., 2011; Li et al., 2007; Liao et al., 2012, 2013), a derivative of 5,7-dihydroxychromone-7-O-glucopyranoside (30) (Liao et al., 2013), was a new structure chromone that was found from P. capitatum and reported in, 2007 for the first time. Benzo-γ-pyron can be considered the parent nucleus of flavonoids. Flavonoids in P. capitatum have been found to be effective constituents and fall into six major types: flavone, isoflavone, flavanone, flavonol, flavanonol, and flavan-3-ol. Two flavones named luteolin (33) (Jing et al., 2015; Zhang et al., 2013b) and luteolin-7-O-glucoside (34) (Wang & Jiang, 2018), and one isoflavone named daidzin (35) (Jing et al., 2015) were isolated from P. capitatum. Twenty-nine flavonols (38−66) were isolated from various parts of P. capitatum and were of the same structure. Among them were four glycosides (39−42) (Huang et al., 2008, 2015; Liao et al., 2013; Wang et al., 2013; Yang et al., 2015b; Zhang et al., 2012) of kaempferol (38) (Jing et al., 2015; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Yang et al., 2015b; Yu et al., 2008; Zhang et al., 2012, 2013a,b), one methylation product named 3-O-methylquercetin (44) (Huang et al., 2015; Liao et al., 2013; Wang et al., 2013) and seventeen glycosides (45−61) of quercetin (43) (He et al., 2014; Huang et al., 2008, 2015, 2019; Jing et al., 2015; Li et al., 2000, 2007; Liao et al., 2012, 2013; Liu et al., 2008; Wang et al., 2013; Wang & Jiang, 2018; Yang et al., 2008, 2015a,b; Yao et al., 2018; Yu et al., 2008; Zhang et al., 2010, 2012, 2013a,b; Zhao et al., 2011; Zheng et al., 2014; Zhou et al., 2017). Myricitrin (62) (Jing et al., 2015; Liao et al., 2013; Wang et al., 2013; Yang et al., 2015a; Zhang et al., 2012; Zhao et al., 2011; Zheng et al., 2014) and 3,3′,4′,5,5′,7-hexahydroxyflavone-3-O-(5-O-acetyl-L-arabinoside) (63) (Yao et al., 2018) are two glycosides of myricetin. 3′-Hydroxy-3,4′,5,5′,8-pentamethoxy-6,7-methylenedioxyflavone (64) (Yao et al., 2018), 3′,4′-methylenedioxy-3,5,6,7,8,5′-hexamethoxyflavone (65) (Gao et al., 2001), and viviparum B (66) (Yao et al., 2018; Zhou et al., 2017) all had a methylenedioxy structure. Compound 65 was a new structure flavonol obtained from P. capitatum and reported in, 2001 for the first time (Gao et al., 2001). Two flavanones (36,37) (Liao et al., 2013; Yang et al., 2017b), one flavanonol (67) (Huang et al., 2015), and six flavan-3-ols (68−73) (Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b; Yao et al., 2018; Zhang et al., 2013a, b; Zhou et al., 2017) were also found from P. capitatum. 2,7,4′-Trihydroxyflavanone-5-O-β-D-glucopyranoside (37) (Yang et al., 2017b) is a 2-hydroxylation product of flavanone. (−)-Epicatechin-(2β→O→7,4β→8)-(+)-catechin (72) (Yang et al., 2015b), also named procyanidin A1 and obtained from Polygonaceae for the first time, is a condensation product of (−)-epicatechin (68) (Yang et al., 2015b) and (+)-catechin (69) (Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b; Yao et al., 2018; Zhang et al., 2013a, b; Zhou et al., 2017). 3-Galloyl-(−)-epicatechin-(4β→8)-3-galloyl-(−)-epicatechin (73) (Yao et al., 2018; Zhou et al., 2017), also named 3,3′-digalloylprocyanidin B2, is a condensation product of (−)-epicatechin (68) (Yang et al., 2015b).

Catechol (74) (Zhang et al., 2010), which belonged to phenols, was obtained from P. capitatum. Twenty-nine phenolic acids and their esters (75−103) were found from P. capitatum, including two hydroxylation products of benzoic acid (75,76) (Jing et al., 2015; Wang et al., 2013), protocatechuic acid (77) (Chen et al., 2011; Huang et al., 2019; Jing et al., 2015; Li et al., 2007; Liao et al., 2013; Liu et al., 2008;Yang et al., 2015a,b; Yu et al., 2008; Zhang et al., 2010; 2013a,b; Zhao et al., 2011; Zheng et al., 2014), one methylation product (78) (Chen et al., 2011; Li et al., 2007; Yu et al., 2008; Zhang et al., 2013a ,b) and one ethyl ester (79) (Wang et al., 2013; Yu et al., 2008; Zhang et al., 2010) of protocatechuic acid. Gallic acid (80) (Chen et al., 2010b, 2011; Huang et al., 2008, 2019; Liao et al., 2013; Liu et al., 2008; Wang et al., 2013; Wu & Wang, 1985; Yang et al., 2008, 2015a,b; Yu et al., 2008; Zhang et al., 2010, 2013a,b; Zhao et al., 2011; Zheng et al., 2014; Zhou et al., 2017) was found to be another effective constituent of P. capitatum. Sixteen derivatives of gallic acid (81−96) were isolated from the aerial parts or whole plant of P. capitatum, including two methylation products (81,82) (Liao et al., 2013; Zhang et al., 2010,2013a,b), one methyl ester (83) (Jing et al., 2015; Zhang et al., 2013b), and one ethyl ester (84) (Huang et al., 2015; Liu et al., 2008; Wang et al., 2013; Yang et al., 2015b; Yu et al., 2008; Zhang et al., 2010, 2013b; Zhao et al., 2011) of gallic acid, two ellagic acids (85,86) (Liao et al., 2013; Wang et al., 2013; Zhang et al., 2012; Zhou et al., 2017), brevifolin (87) (Wang et al., 2013) and two of its derivatives (88,89) (Chen et al., 2010b; Wang et al., 2013), and seven glucosides (90−96) (Fu et al., 2012; He et al., 2014; Ma et al., 2014; Wang et al., 2014; Yang et al., 2008, 2015b; Yao et al., 2018; Zhou et al., 2017) of gallic acid. Trans-p-coumaric acid (97) (Liao et al., 2013), three derivatives (98−100) (Huang et al., 2008; Liu et al., 2008; Yang et al., 2009) of ferulic acid, and three disubstituted phenylpropanoid sucrose esters (101−103) (Liao et al., 2013; Yao et al., 2018; Zhou et al., 2017) were obtained from P. capitatum. Furthermore, the two flavonol glycosides mentioned above (55,57) (Liao et al., 2012, 2013; Zhang et al., 2012) also contained the trans-p-coumaroyl group.

Twelve lignanoids (104−115) (Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b; Yao et al., 2018; Ye et al., 2017; Zhang et al., 2013a, b; Zhao et al., 2010; Zhou et al., 2017) were obtained from the aerial parts or whole plant of P. capitatum including five derivatives (105−109) (Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b; Yao et al., 2018; Ye et al., 2017; Zhang et al., 2013a, b; Zhao et al., 2010; Zhou et al., 2017) of (+)-isolariciresinol (104) (Ye et al., 2017) and five derivatives (111−115) (Huang et al., 2015; Yang et al., 2015b; Yao et al., 2018; Ye et al., 2017; Zhao et al., 2010; Zhou et al., 2017) of (−)-isolariciresinol (110) (Huang et al., 2015). Isolation of four flavonolignans (116−119) (Huang et al., 2015; Jing et al., 2015; Yang et al., 2015b) from this plant was reported for the first time, so was the isolation of flavonolignans from Polygonaceae (Yang et al., 2015b).

Ten phenolic glycosides (120−129) (Huang et al., 2015; Liao et al., 2012, 2013; Yang et al., 2017b; Zhang et al., 2012) were obtained from the whole plant of P. capitatum. Except 3-methoxyl-5-hydroxyphenol-1-O-β-D-glucopyranoside (127) (Huang et al., 2015; Yang et al., 2017b), 3-methoxyl-5-hydroxyphenol-1-O-β-D-(6′-O-galloyl)glucopyranoside (128) (Liao et al., 2012, 2013; Zhang et al., 2012), and 3-methoxyl-5-hydroxyphenol-1-O-β-D-(6′-O-galloyl)galactopyranoside (129) (Liao et al., 2012, 2013), all the other phenolic glycosides (121−126) (Huang et al., 2015; Yang et al., 2017b) can be considered derivatives of arbutin (120) (Huang et al., 2015; Yang et al., 2017b), with methoxylations of benzene ring or galloylations of glycoside.

Four alcoholic glycosides (130−133) (Huang et al., 2015; Yang et al., 2017b) were obtained from the whole plant of P. capitatum. β-D-Glucopyranosyl-12-hydroxy-12-(2″-hydroxy-2″-carboxyethyl)jasmonic acid (133), a derivative of β-D-glucopyranosyl-12-hydroxyjasmonic acid (132), was a new structure compound reported in, 2017 (Yang et al., 2017b). Both compound 132 and compound 133 are hydroxyjasmonic acid derivatives.

Two amino acids (134,135) (Jing et al., 2015; Liao et al., 2013; Yang et al., 2017b), one nucleobase (136) (Jing et al., 2015), two amides (137,138) (Liao et al., 2013; Wang et al., 2013), and one alkaloid (139) (Wang et al., 2013) were obtained from the aerial parts or whole plant of P. capitatum. It is possible that flazine (139) is produced through dehydration and dehydrogenation of 5-hydroxymethyl furfural (8) (Yu et al., 2008) and L-tryptophan (135) (Yang et al., 2017b).

Eight alkyl glycosides (140−147) (Yang et al., 2011, 2017a) were obtained from the whole plant of P. capitatum. Their alkyl groups are all n-butyls, which may be introduced because of n-butanol extraction. The sugar residues of seven alkyl glycosides (140−146) are glucosyl or fructosyl with a pyran or furan ring structure (Yang et al., 2017a).

Fifty-six kinds of volatile oils (148−203) (Gao et al., 2005; Wang et al., 2007) were identified from the whole plant of P. capitatum, including monoterpenes, sesquiterpenes, monocyclic and polycyclic aromatic hydrocarbons, and straight-chain aliphatic (less than 24 carbons) hydrocarbons, alcohols, aldehydes, ketones, acids, and esters.

In addition, water-soluble polysaccharides were isolated from water-extract of P. capitatum. Analysis, using GC and GC-MS after hydrolysis and derivatization, showed that their monosaccharide components include rhamnose, arabinose, xylose, glucose, and galactose, among which rabinose, glucose, and galactose were the major components (Wang et al., 2011).

3 Conclusions

To sum up, previous phytochemical studies on P. capitatum showed that types of phytochemical constituents of P. capitatum included aliphatic hydrocarbons, aliphatic alcohols, aliphatic ketones, aromatic aldehydes, aliphatic acids, glycerides, triterpenic acids, sterols, anthraquinones, chromones and their glycosides, flavonoids and their glycosides, phenols, phenolic acids and their esters, lignanoids, flavonolignans, phenolic glycosides, alcoholic glycosides, amino acids, nucleobases, amides, alkaloids, alkyl glycosides, volatile oils, and polysaccharides.

The majority of studies on P. capitatum focused on (1) pharmacological effects and their mechanism related to hypoglycemic, antimicrobial and antitumor activities, (2) extraction, separation and purification of single components, effective component groups or fractions, (3) development of content determination or quality control methods for raw materials or pharmaceutical preparations.

This review provides reference for further research and application of P. capitatum and related preparations.

Acknowledgements

This work was supported by the Xuzhou Medical Young Talent Project (Xuweikejiao[2015]7) and the Science and Technology Talent Development Project of CPLA Army (Zhenggan[2019]174).

• Practical Application: The results of this review provide reference for further research and application of P. capitatum and related preparations.

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Publication Dates

• Publication in this collection
  14 Mar 2022
• Date of issue
  2022

History

• Received
  02 Nov 2021
• Accepted
  13 Dec 2021