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. 2022 Jun 16;12(1):21. doi: 10.1007/s13659-022-00346-z

The genus Rumex (Polygonaceae): an ethnobotanical, phytochemical and pharmacological review

Jing-Juan Li 1,2, Yong-Xiang Li 1,2, Na Li 1, Hong-Tao Zhu 1, Dong Wang 1, Ying-Jun Zhang 1,3,
PMCID: PMC9203642  PMID: 35710954

Abstract

Rumex L., a genus in Polygonaceae family with about 200 species, is growing widely around the world. Some Rumex species, called "sorrel" or "dock", have been used as food application and treatment of skin diseases and hemostasis after trauma by the local people of its growing areas for centuries. To date, 29 Rumex species have been studied to contain about 268 substances, including anthraquinones, flavonoids, naphthalenes, stilbenes, diterpene alkaloids, terpenes, lignans, and tannins. Crude extract of Rumex spp. and the pure isolates displayed various bioactivities, such as antibacterial, anti-inflammatory, antitumor, antioxidant, cardiovascular protection and antiaging activities. Rumex species have important potential to become a clinical medicinal source in future. This review covers research articles from 1900 to 2022, fetched from SciFinder, Web of Science, ResearchGate, CNKI and Google Scholar, using “Rumex” as a search term ("all fields") with no specific time frame set for the search. Thirty-five Rumex species were selected and summarized on their geographical distribution, edible parts, traditional uses, chemical research and pharmacological properties.

Keywords: Polygonaceae, Rumex L., Anthraquinones, Phenolics, Pharmacological properties

Introduction

Rumex L., the second largest genus in the family Polygonaceae, with more than 200 species, is mainly distributed in the northern temperate zone [1]. It is mostly perennial herbs with sturdy roots, paniculate inflorescences, and triangular fruits that are enveloped in the enlarged inner perianth. The name "Rumex" originated from the Greek word–"dart" or "spear", alluding to the shape of leaves [2]. The other explanation from Rome–"rums" alludes to the function that the leaves could be sucked to alleviate thirst [3]. R. acetosa, a typical vegetable and medicinal plant, whose name 'acetosa' originated from the Latin word "acetum", described the taste of the plant as vinegar. Currently, many oxalic acids have been reported from Rumex, verifying its sour tastes [4].

Rumex species have had a valued place as global folk medicine, e.g., in Southern Africa, America, India, China, and Turkey. The earliest medicinal record of Rumex spp. in China was in "Shennong's Herbal Classic", in which Rumex was recorded for the treatment of headed, scabies, fever, and gynecological diseases. Roots of Rumex, also called dock root, have been reported for its therapeutic capacity of bacterial infections, inflammatory, tumor and cardiovascular diseases [5, 6]. Recently, pharmacological study showed that Rumex species displayed apparent antibacterial and antifungal effects [7], and were employed in the management of skin scabies and inflammation [8, 9]. The processed Rumex exhibited different chemical profiles and bioactivities [10, 11]. Leaves, flowers and seeds of some Rumex plants are edible as vegetables, while in some regions, the Rumex plants are regarded as noxious weeds because oxalic acid makes them difficult to be digested [12].

To date, 268 components from 29 Rumex species have been reported. Anthraquinones, flavonoids, tannins, stilbenes, naphthalenes, diterpene alkaloids, terpenes, and lignans were as the main chemical components, with a broad spectrum of pharmacological activities, such as anti-inflammatory, antioxidant, antibacteria, antitumor, and antidiabetic activities [1317]. In addition to important role of Rumex in the traditional applications, researchers also regard Rumex as a potential effective medicine of many diseases. This article has reviewed a comprehensive knowledge on the distribution, traditional uses, chemistry and bioactivity progress of Rumex, and their therapeutic applications and utilizations were provided.

Geographical distributions, local names, parts used and traditional uses

The genus Rumex with more than 200 species, is distributed widely in the world and has been used traditionally in many regions, e.g., Asia, America, Europe and other continents. Many of them known as "sorrel" or "dock" have a long history of food application and medicinal uses for the treatment of skin diseases, and hemostasis after trauma by the local people of its growing areas. For example, R. acetosa is commonly used medicinally for diuretics around the world [4]. R. maritimus and R. nepalensis, used as laxatives, have long-term medicinal applications in India as substitutes for Rheum palmatum (Polygonaceae), which is usually used to regulate the whole digestive system. Moreover, Indians have also recorded nine Rumex plants as astringent agents, including R. acetosa, R. acetosella, R. crispus, R. dentatus, R. hastatus, R. maritimus, R. nepalensis, R. scutatus, and R. vesicarius [18]. All seven species included R. acetosa, R. trisetifer, R. patientia, R. crispus, R. japonicus, R. dentatus and R. nepalensis, called "jinbuhuan", have been used for hemostasis remediation in China [19]. R. thyrsiflorus, rich in nutrition, has been used as food by Europeans in history and as folk medicine due to its obvious anti-inflammatory activity [20]. R. lunaria has been used to treat diabetes by Canarian medicine [16]. The leaves of more than 14 Rumex spp., such as R. acetosa, R. hastatus, R. thyrsiflorus, R. aquaticus, R. crispus, R. gmelini, R. patientia, R. vesicarius, R. ecklonianus, R. abyssinicus, R. confertus, R. hymenosepalus, R. alpinus and R. sanguineus (Table 1) could be eaten freshly or cooked as vegetables in the folk of many places [5, 6]. In Table 1, the geographical distributions, local names, parts used and traditional uses of 35 Rumex species are summarized.

Table 1.

Traditional uses of Rumex plants

No Species Local names Country Parts used Traditional uses Ref
R1 Rumex acetosa L Sorrel, garden sorrel, common dock, broad-leaved sorrel, English sorrel, sheep’s sorrel, red sorrel, sour weed, field sorrel South Africa, North America, Europe, Yemen, Czech Repubilc, Korea, Britain, Ireland, China, Hungary, Romania and Bulgaria Leaf, flower, whole plant, fruit, root and seed Gastrointestinal disorders (constipation, cramping, diarrhea, tenesmus), antiscorbutic, hemostasis, dermatological, tumors, cramping, sore throats, warts, dysentery, gonorrhea, ulcer, scabies, kidney diseases (diuretic), fever, worm, abscesses. Seed: astringent [4, 18, 19, 57, 135, 192, 198]
R2 R. hastatus D. Don Heartwing sorrel, hastate-leaved dock, sour dock, khatimal China, India, Nepal, Bhutan, Pakistan and Afghanistan Leaf, flower, seed, root, whole plant, anile part and contemporary tuber Astringent, sexually transmitted diseases (AIDs), constipation, tonic agent, diuretic, rheumatism, dermatological, piles, bleeding of the lungs, cough, headache, fever, blood pressure, abdominal pain, sore throat, tonsillitis diseases, worm, wounds [18, 58, 191, 195]
R3 R. thyrsiflorus Fingerh Compact dock, thyrse sorrel China, Kazakhstan and Russia, and Europe Leaf For food [59, 198]
R4 R. aquaticus L Red dock, western dock China, Japan, Kazakhstan, Russia and Europe Leaf Disinfection, constipation, fever, diarrhea, stomach problems, edema, jaundice [60, 201]
R5 R. Chalepensis Mill Asia, Middle East, Morocco and Africa [40, 61, 202]
R6 R. crispus L Curled dock, curly dock, yellow dock, narrow-leaf dock Asia, Europe, North America, Northern Africa, Colombia and India Leaf, root, stem, seed Antidysentery, hemostasis, ulcers, cough. Root: laxative, astringent, skin eruptions, skin diseases, scrofula, scurvy, intermittent fevers, congested liver and jaundice. Seed: astringent [18, 19, 62, 195, 197]
R7 R. dentatus L Toothed dock Asia, Middle East and Southeast Europe and Pakistan Whole plant Cutaneous disorders, stomach problems. Plant: astringent, hemostasis [18, 19, 28, 63, 195]
R8 R. gmelini Turcz. ex Ledeb China, Japan, North Korea, Russia, Mongolia and Siberia Leaf Tumor, bacterial infection [31, 64]
R9 R. japonicus Houtt China, Japan, North Korea and Russia Whole plant Hemostasis, fever, constipation [19, 65, 199]
R10 R. maritimus L Golden dock Bangladesh, India, North Africa and America Leaf, root and seed Leaf and root: laxative; externally applied to burns. Seed: aphrodisiac [18, 66]
R11 R. nepalensis Spreng Asia, Europe and Africa, Ethiopia, Nepal, Pakistan and India Leaf, root and whole plant Hemostasis, stomach problems, itch, astringent, paralysis, tonsillitis, ascariasis, uterine bleeding, as an abortifacient, joint pain. Leaf: colic; externally applied to syphilitic ulcers. Root: constipation [18, 19, 33, 67, 195, 196]
R12 R. obtusifolius L Broad-leaf dock, bitter dock, blunt-leaf dock China, Japan, Europe, Africa and Ireland Whole plant Nettle, depurative, astringent, constipation, tonic agent, sores, blisters, hyperglycemic, burns, tumors [62, 193, 194]
R13 R. patientia L Herb patience, garden patience, patience dock, spinach dock Asia, Europe, North India, Bulgaria and Ukraine Leaf Hemostasis, diarrhoea, diarrhoea in cows [4, 19, 68, 192, 198]
R14 R. cristatus DC Greek dock France, Turkey and Spain [6971]
R15 R. vesicarius L Bladder dock, country sorrel South Asia, Egypt and North Africa Leaf, seed and whole plant Plant: astringent, antiscorbutic, stomach problems, diuretic. Seed: antidysentery [18, 72, 73, 203]
R16 R. luminiastrum Jaub & Spach Europe [42]
R17 R. pictus Forssk Veined dock Egypt, Gulf States, Kuwait, Lebanon-Syria, Libya, Palestine, Saudi Arabia, Sinai and Israel Whole plant For food

[41, 74, 75]

[76, 203]

R18 R. bucephalophorus L North America and Libya Whole plant Laxative [77, 204]
R19 R. tingitanus L Koressa Europe, Asia and Africa Whole plant Hepatoprotective, antidepression, blood purifcation, constipation, tonic [78, 186]
R20 R. ecklonianus Meissner South African dock South Africa Young leaf Anemia, chlorosis [79]
R21 R. abyssinicus Jacq Spinach rhubarb, mekmeko Europe, Africa and Spinach Young shoot, leaf, fresh or dried plant Brest cancer, stomach problems, gonorrhea, liver diseases, wounds, diabetes, cough, hypertension, sores, rheumatism, hemorrhoids, scabies, diarrhoea [80, 123]
R22 R. confertus Willd Russian dock, Asiatic dock, mossy sorrel Russia, Kazakhstan, China, Hungary, Slovakia, Romania, Italy, Europe, Finland, Norway, Sweden, Lithuania, Britain,Canada, north Dakota,Bulgaria and Ukraine Leaf, root and rhubarb Diarrhoea, diarrhoea in cows [8191, 198]
R23 R. hymenosepalus Torr Canaigre, canaigre dock, desert rhubarb, wild rhubarb, sand dock Australia, American California, Sonoran and Mexico Leaf, tuber and rhubarb Throat infections [92, 93, 205, 206]
R24 R. alpinus L Alpine dock, monk's rhubarb Europe and Asia Leaf and rhubarb For food [94]
R25 R. rugosus Campd North America, Europe Leaf For food [95, 96, 200]
R26 R. nervosus Vahl Ithrib Himalayas, Nilgiri, Nainital, East Africa and Arab Leaf Microbial infections, anticoccidial [97, 98, 207]
R27 R. maderensis Lowe Azedas, madeira sorrel Portugal Leaf Blood depurative, dermatosis, diuretic, simulated gastrointestinal digestion, antidiabetic [99, 100]
R28 R. chinensis Campd. (Syn. = R. trisetifer) Vietnam, China Microbial infections [101]
R29 R. algeriensis Barratte & Murb. (Syn. = R. elongatus) Algeria [102]
R30 R. tunetanus Tunisia [103, 104]
R31 R. rechingerianus Losinsk. (Syn. = R. pamiricus) Trans-Ili Ala-Tau [61]
R32 R. lunaria L Canarian Diabetes [16]
R33 R. rothschildianus Aarons Palestine Whole plant Constipation, diarrhea, wound, diuretic, eczema and for food [105]
R34 R. sanguineus L Bloody dock, red veined dock, red-veined dock, red veined sorrel, red-veined sorrel America, Canada, Chile and Italy Young leaf Wound, bacterial infections and abscesses [61, 106]
R35 R. acetosella Linn Sheep sorrel Asia and Colombia Root, the aerial part and leaf Diuretic, constipation, diaphoretic, antiscorbutic. Fresh plant: urinary and kidney diseases [18, 195]

– unknown

Chemical constituents

To date, 268 compounds including 56 quinones (156), 57 flavonoids (57113), 25 tannins (114138), 6 stilbenes (139144), 22 naphthalenes (145166), 6 terpenes (167172), 3 diterpene alkaloids (173175), 14 lignans (176189) and 79 other types of components (190268) were isolated and reported from 29 Rumex species (Table 2).

Table 2.

The summary of compounds in Rumex

No Compounds Formula Species Plant parts Ref
Quinones
 1 Chrysophanol C15H10O4 R2, R5, R7, R8, R9, R11, R13, R21, R22, R23, R28, R31 Rh, R, WP, T, A, S, F [23, 35, 45, 46, 50, 51, 63, 80, 93, 101, 113, 125, 128, 129]
 2 Chrysophanol-1-O-β-D-glucoside C21H20O9 R8, R31 R, S [64, 128]
 3 Chrysophanol-8-O-β-D-glucoside (chrysophanein) C21H20O9 R8, R9, R13, R21, R28 A, S, R, WP [32, 46, 54, 101, 123, 129, 130]
 4 Chrysophanol-8-O-β-D-galactoside C21H20O9 R8, R14 R [52, 112]
 5 Chrysophanol-1-O-(4-O-β-D-galactosyl)-α-L-rhamnoside C27H30O13 R2 WP [184]
 6 6'-Acetyl-chrysophanol-8-O-β-D-glucoside C23H22O10 R8 R [32, 112, 113]
 7 Chrysophanol anthrone C15H12O3 R1 R [29]
 8 Emodin (1,6,8-trihydroxy-3-methylanthraquinone) C15H10O5 R2, R5, R6, R8, R9, R11, R13, R21, R28, R31 Rh, R, WP, A, S, F, L [23, 32, 34, 35, 40, 4547, 51, 54, 80, 101, 112, 113, 128, 129]
 9 Emodin-1-O-β-D-glucoside C21H20O10 R7, R8 R, A [14, 64]
 10 Emodin-1-O-β-D-glucosyl-α-L-rhamnoside C27H30O14 R5, R31 R, S, L [128, 131]
 11 Emodin-6-O-β-D-glucoside C21H20O10 R13 R [54, 130]
 12 Emodin-8-O-β-D-glucoside (PMEG) C21H20O10 R4, R6, R8, R9, R13, R28 WP, A, R, S [23, 32, 34, 38, 46, 47, 101, 112, 129, 130]
 13 Aloe-emodin C15H10O6 R2, R8, R13 R, WP, L [23, 27, 35, 112]
 14 6-Hydroxy-emodin (citreorosein) C15H10O6 R9, R21 WP [50, 123]
 15 6-Acetoxy-aloe-emodin C17H12O6 R1 R [29]
 16 Emodin dimethylether C17H14O5 R13 WP [23]
 17 Emodin anthrone C15H12O4 R1 R [29]
 18 Physcion (rheochrysin, emodin 3-methyl ether) C16H12O5 R2, R8, R9, R11, R13, R21, R23, R28 Rh, R, WP, T, A [23, 35, 46, 50, 51, 54, 80, 93, 101, 113, 129]
 19 Physcion-8-O-β-D-glucoside (physcionin) C22H22O10 R8, R9, R13, R21, R28 A, F, R, WP [45, 101, 123, 129, 130]
 20 Physcion anthrone C16H14O4 R1 R [29]
 21 Rumejaposide A C22H22O11 R9 R [26]
 22 Rumejaposide B C22H22O11 R9 R [26]
 23 Rumejaposide C C22H22O12 R9 R [26]
 24 Rumejaposide D C22H22O13 R9 R [26]
 25 Rumejaposide E C21H22O10 R7, R9 R [26, 28]
 26 Rumejaposide F C21H22O10 R7, R13 L, R [27, 28]
 27 Rumejaposide G C21H22O9 R7 R [28]
 28 Rumejaposide H C21H22O9 R7 R [28]
 29 Rumejaposide I C21H22O10 R7, R13 L, R [27, 28]
 30 Xanthorin-5-methylether C17H14O6 R13 WP [23, 24]
 31 Rumexone C17H16O4 R6 R [30]
 32 Rhein C15H8O6 R2 R [35]
 33 Rhein-8-O-β-D-glucoside C21H18O11 R9 WP [50]
 34 Cassialoin C21H22O9 R7, R13 L, R [27, 28]
 35 Phallacinol (telochistin) C16H12O6 R11 R [51]
 36 1,8-Dihydroxyanthraquinone C14H8O4 R1 R [29]
 37 Martianine C42H42O17 R11 R [132]
 38 Rumoside A C42H42O16 R8, R13 R [32, 112]
 39 10-Hydroxyaloin A C21H22O10 R8 R [31]
 40 10-Hydroxyaloin B C21H22O10 R8 R [31]
 41 6-Methoxyl-10-hydroxyaloin A C22H24O11 R8 R [32]
 42 6-Methoxyl-10-hydroxyaloin B C22H24O11 R8 R [32]
 43 10-Hydroxycascaroside C C27H32O14 R11 R [132]
 44 10-Hydroxycascaroside D C27H32O14 R11 R [132]
 45 Obtusifolate A C39H42O8 R12 R [25]
 46 Obtusifolate B C34H34O7 R12 R [25]
 47 Rumexpatientoside A C22H24O10 R11 R [133]
 48 Rumexpatientoside B C22H24O10 R11 R [133]
 49 Nepalenside A C21H22O11 R11 R [33]
 50 Nepalenside B C21H22O11 R11 R [33]
 51 Helminthosporin C15H12O5 R21 Rh [80]
 52 1,3,5-Trihydroxy-7-methylanthraquinone C15H10O5 R13 R [130]
 53 1,5-Dihydroxyanthraquinone C14H8O4 R6 R [30]
 54 1,3,7-Trihydroxy-6-methylanthraquinone C15H10O5 R2 WP [134]
 55 Przewalskinone B C16H12O5 R2 WP [134]
 56 Rumpictusoide A C21H19O10 R17 WP [183]
Flavonoids
 57 Vitexin C21H20O10 R1 A [57]
 58 Isovitexin C21H20O10 R15 A [185]
 59 Orientin C21H20O11 R1, R16 A, WP [42, 57]
 60 Acetyl-orientine C23H22O12 R16 WP [42]
 61 Iso-orientine C21H20O11 R1 A [57]
 62 Quercetin-3-O-β-D-galactoside (hyperoside) C21H20O11 R1, R7, R13, R31 S, R, WP [36, 44, 47, 49]
 63 Kaempferol C15H10O6 R2, R6, R7, R13 WP, R, A [14, 23, 34, 35]
 64 Kaempferol-3-O-β-D-glucoside C21H20O11 R4, R7, R13 WP, A [14, 23, 3638]
 65 Kaempferol-3-O-α-L-rhamnoside C21H20O10 R1, R6 L, WP [34, 39]
 66 Kaempferol-3-O-α-L-rhamnosyl-(1 → 6)-β-D-galactoside C27H30O15 R5, R7 L, WP [36, 40]
 67 Kaempferol-3-O-α-L-arabinosyl-(1 → 6)-β-D-galactoside C26H28O15 R17 A [41]
 68 Kaempferol-3-O-[2''-O-acetyl-α-L-arabinosyl]-(1 → 6)-β-D-galactoside C28H30O16 R17 A [41]
 69 Kaempferol-7-O-β-D-glucoside C21H20O11 R16 WP [42]
 70 Kaempferol-7-O-α-L-rhamnoside C21H20O10 R16 WP [42]
 71 Quercetin C15H10O7 R2, R5, R7, R8, R13 F, S, R, A [14, 35, 45, 47, 48]
 72 Quercetin-3-O-β-D-glucoside (isoquercetin, ECQ, QGC) C21H20O12 R4, R5, R7, R13 A, WP, L, S [14, 23, 27, 37, 38, 46, 47]
 73 Quercetin-3-O-β-D-glucuronide C21H18O13 R7, R13 A [14, 46]
 74 Quercetin-3-β-D-glucosyl-(1 → 4)-β-D-galactoside C27H30O17 R5 L [40]
 75 Quercetin-3-O-α-L-rhamnoside (quercitrin) C21H20O11 R4, R5, R9, R13, R31 L, WP, R, A [27, 38, 40, 49, 50]
 76 Isorhamnetol C16H12O7 R13 WP, [23, 37]
 77 Isorhamnetol-3-O-rutinoside C28H32O16 R7 WP [36]
 78 Isorhamnetol-3-O-β-D-galactoside C22H22O12 R7 WP [36]
 79 Isorhamnetol-3-O-β-D-glucoside C22H22O12 R7 WP [36]
 80 Quercetin-3-O-α-L-arabinoside C20H18O11 R4, R16 WP, A [38, 42, 43]
 81 Quercetin-3-O-α-L-arabinosyl-(1 → 6)-β-D-galactoside C26H28O16 R17 A [41]
 82 Quercetin-3-O-[2''-O-acetyl-α-L-arabinosyl]-(1 → 6)-β-D-galactoside C28H30O17 R17 A [41]
 83 Quercetin-7-O-β-D-glucoside C21H20O12 R13, R16 S, WP [42, 44, 47]
 84 Quercetin-7-O-α-L-rhamnoside C21H20O11 R16 WP [42]
 85 Rutin C21H30O16 R5, R8, R31 R, L [32, 40, 49, 112]
 86 5-Hydroxy-4'-methoxyflavone-7-O-β-D-rutinoside C28H32O14 R13 WP [23, 37]
 87 Apigenin C15H10O5 R1 R [53]
 88 Luteolin (cyanidenon) C15H10O6 R1, R19, R35 L, WP, A [136, 186188]
 89 Luteolin-7-O-β-D-glucoside C21H20O11 R16 WP [42]
 90 7-Hydroxy-2,3-dimethyl-chromone C11H10O3 R14 R [52]
 91 5-Methoxy-7-hydroxy-1(3H)-chromone C10H8O4 R13 R [53]
 92 5,7-Dihydroxy-1(3H)-chromone C9H6O4 R13 R [53]
 93 Mikanin (3,5-dihydroxy-4',6,7-trimethoxyflavone) C18H16O7 R13 L [27]
 94 3,5-Dihydroxy-6,7,3',4'-tetramethoxyflavone C19H18O8 R13 L [27]
 95 2,5-Dimethyl-7-hydroxychromone-7-O-β-D-glucoside C17H20O8 R8 R [31]
 96 2,5-Dimethyl-7-hydroxychromone C11H10O3 R11 R [51]
 97 3-O-Methyl quercetin C16H12O7 R8 F [45]
 98 Tricin-7-O-β-D-glucoside C23H24O12 R22 R [137]
 99 2-(2'-Hydroxypropyl)-5-methyl-7-hydroxychromone C13H14O4 R13 R [138]
 100 2-(2'-Hydroxypropyl)-5-methyl-7-hydroxychromone-7-O-β-D-glucoside C19H24O9 R13 R [138]
 101 Maackiain C16H12O5 R13 A [46]
 102 Maackiain-3-O-β-D-glucoside C22H22O10 R13 A [46]
 103 Aloesin C19H22O9 R11 R [33]
 104 4'-p-Acetylcoumaroyl luteolin C26H18O9 R19 L [78]
 105 Catechin C15H14O6 R1, R6, R13, R19, R31 R, WP [34, 49, 53, 54]
 106 6-Cl-catechin C15H13ClO5 R13, R19 R [54]
 107 Epicatechin C15H14O6 R1, R6, R14, R31 R, WP [34, 49]
 108 (+)-Epigallocatechin C15H14O7 R1 R [135]
 109 (−)-Epigallocatechin C15H14O7 R1 R [135]
 110 Epicatechin-3-O-gallate C22H18O10 R1, R31 A, R [49, 56]
 111 Epigallocatechin-3-O-gallate C22H18O11 R1 A [56]
 112 Isokaempferide C16H12O6 R4 A, R [148]
 113 Quercetin-3,3'-dimethylether C17H14O7 R4 A, R [148]
Tannins
 114 Epiafzelechin-(4β → 8)-epicatechin-(4β → 8)-epicatechin C45H38O17 R1 A [56]
 115 Epicatechin-(4β → 8)-epicatechin-(4β → 8)-catechin C45H38O18 R1 A [56]
 116 Epicatechin-(4β → 8)-epicatechin-(4β → 8)-epicatechin (Procyanidin C1) C45H38O18 R1 A [56]
 117 Epicatechin-3-O-gallate-(4β → 8)-epicatechin-3-O-gallate-(4β → 8)-epicatechin-3-O-gallate C66H50O30 R1 A [56]
 118 Epicatechin-(4β → 8)-epicatechin-(4β → 8)-epicatechin-(4β → 8)-epicatechin C60H50O24 R1 A [56]
 119 Epicatechin-3-O-gallate-(4β → 8)-epicatechin-3-O-gallate C44H34O20 R1 A [139]
 120 Epicatechin-(4β → 6)-epicatechin (procyanidin B5) C30H26O12 R1 A [56]
 121 Epicatechin-(4β → 6)-catechin C30H26O12 R1 A [56]
 122 Epicatechin-(4β → 8)-catechin (procyanidin B1) C30H26O12 R1 A [56, 107]
 123 Catechin-(4α → 8)-catechin (procyanidin B3) C30H26O12 R1 A [56, 107]
 124 Catechin-(4α → 8)-epicatechin (procyanidin B4) C30H26O12 R1 A [56, 107]
 125 Epiafzelechin-(4β → 8)-epicatechin (procyanidin B2) C30H26O11 R1 A [56, 107]
 126 Epicatechin-(4β → 8)-epicatechin-3-O-gallate C37H30O16 R1 A [56]
 127 Epiafzelechin-(4β → 8)-epicatechin-3-O-gallate C37H30O15 R1 A [56]
 128 Epicatechin-(4β → 6)-epicatechin-3-O-gallate C37H30O16 R1 A [56]
 129 Epicatechin-3-O-gallate-(4β → 6)-epicatechin-3-O-gallate C44H34O20 R1 A [56]
 130 Epiafzelechin-3-O-gallate-(4β → 8)-epicatechin-3-O-gallate C44H34O19 R1 A [56]
 131 Epicatechin-(2β → 7, 4β → 8)-epicatechin-(4β → 8)-epicatechin (cinnamtannin B1) C45H36O18 R1 A [56]
 132 Epicatechin-(2β- > 7, 4β → 8)-epiafzelechin-(4α → 8)-epicatechin C45H36O17 R1 A [56]
 133 Epicatechin-3-O-gallate-(2β → 7,4β → 8)-epicatechin-(4β → 8)-epicatechin (cinnamtannin B1-3-O-gallate) C52H40O22 R1 A [56]
 134 Epicatechin-(2β → 7, 4β → 8)-epicatechin-(4β → 8)-phloroglucinol C36H28O14 R1 A [56]
 135 Epiafzelechin-(4β → 6)-epicatechin-3-O-gallate C37H30O15 R1 A [56]
 136 Parameritannin A1 C60H48O24 R1 A [56]
 137 Epicatechin-3-O-gallate-(4β → 8)-epicatechin-3-O-gallate-phloroglucinol C50H38O25 R1 A [56]
 138 Epicatechin-(2β → 7, 4β → 8)-epicatechin C30H26O12 R1 A [56]
Stilbenoids
 139 Resveratrol C14H12O3 R2, R8 R, F [32, 35, 45, 112]
 140 (Z)-Resveratrol C14H12O3 R1 R [124]
 141 Polydatin (resveratrol-3-O-β-D-glucoside, piceid) C20H22O8 R7, R8 R, A [14, 32, 112]
 142 5,4'-Dihydroxy-3-methoxystilbene C15H14O3 R18 R [77]
 143 3,5-Dihydroxy-4'-methoxystilbene C15H14O3 R18 R [77]
 144 5,4'-Dihydroxystilbene-3-O-α-arabinoside C19H20O7 R18 R [77]
Naphthalenes
 145 Nepodin (musizin) C13H12O3 R2, R8, R9, R13 R [32, 35, 112, 113, 130]
 146 Nepodin-8-O-β-D-glucoside C19H22O8 R1, R2, R4, R7, R8, R13, R17 R, L, A [27, 31, 38, 46, 63, 74, 110, 130]
 147 Nepodin-8-O-β-D-(6'-O-acetyl)-glucoside C21H24O9 R2 R
 148 Neposide C19H22O8 R2, R22, R24 R, WP [140, 141]
 149 2-Acetyl-3-methyl-6-methoxyl-8-hydroxy-1,4-naphthoquinone C14H12O5 R9 WP [141]
 150 Torachrysone (TRA, 2-acetyl-1,8-dihydroxy-3-methyl-6-methoxyl-naphthalene) C14H14O4 R13 WP [141]
 151 Torachrysone-8-O-β-D-glucoside C20H24O9 R2, R7, R9, R13 L, R, A [27, 46, 53, 63]
 152 2-Methoxystypandrone (MSD, 6-acetyl-7-methyl-2-methoxyl-5-hydroxy-1,4-naphthoquinone) C14H12O5 R9, R10 L, S, R [115, 116]
 153 3-Acetyl-2-methyl-1,5-dihydroxyl-2,3-epoxynaphthoquinol C13H12O5 R9, R11 R, [51, 65]
 154 Rumexoside C20H22O10 R2 R [110]
 155 2-Acetyl-4-chloro-1,8-dihydroxy-3-methylnaphthalene-8-O-β-D-glucoside (patientoside A) C19H21O8Cl R13 R [117]
 156 Patientoside B C17H18O7Cl2 R13 R [117]
 157 4,4''-Binaphthalene-8,8''-O,O-di-β-D-glucoside C36H42O16 R13 R [120]
 158 6-Hydroxymusizin-8-O-β-D-glucopyranoside C15H14O6 R2 R [110]
 159 3-Acetyl-2-methyl-1,4,5-trihydroxyl-2,3-epoxynaphthoquinol C13H14O5 R13 R [118]
 160 3-Acetyl-2-methyl-1,5-dihydroxyl-7-methoxyl-2,3-epoxynaphthoquinol C14H14O6 R13 WP [119]
 161 Rumexone A C14H18O4 R11 R [142]
 162 Rumexneposide A C23H26O9 R11 R [143]
 163 Rumexneposide B C22H26O10 R11 R [143]
 164 Hastatuside B C21H24O9 R2, R13 L, R

[114]

[27]

 165 Epi-isoshinanolone C11H12O3 R13 R [138]
 166 Isoshinanolone C11H12O3 R9, R13 R, WP [50, 138]
Terpenes
 167 Tormentic acid C30H48O5 R9 ST [121]
 168 Myrianthic acid C30H48O6 R9 ST [121]
 169 2α,3α,19α-Trihydroxy-24-norurs-4(23),12-dien-28-oic acid C29H44O5 R9 ST [121]
 170 4(R),23-Epoxy-2α,3α,19α-trihydroxy-24-norurs-12-en-28-oic acid C29H44O6 R9 ST [121]
 171 Taraxasterol acetate C32H52O2 R2 R [35]
 172 Lupeol C30H50O R11 A [189]
Diterpene alkaloids
 173 7,11,14-Trihydroxy-2,13-dioxohetisane (orientinine) C20H23NO5 R17 A [75]
 174 6,13,15-Trihydroxyhetisane (acorientine) C20H27NO3 R17 A [75]
 175 6-Hydroxy-11-deoxy-13-dehydrohetisane (panicudine) C20H25NO3 R17 A [75]
Lignans
 176 Arctiin C27H34O11 R13 WP [23]
 177 3-Hydroxyarctiin C27H34O10 R13 WP [23]
 178 3-Methoxyarctiin-4''-O-β-D-xyloside C27H34O11 R13 WP [23]
 179 4-Ketopinoresinol C20H20O7 R13 L [27]
 180 Syringaresinol C22H26O8 R9, R13 L, WP [27, 50]
 181 Manassantin A C42H52O11 R13 L [27]
 182 Balanophonin C22H22O7 R13 L [27]
 183 Schizandriside C28H32O6 R2 WP [111]
 184 (−)-Isolariciresinol-9-O-β-D-xylopyranoside C25H34O10 R2 WP [111]
 185 (−)-5-Methoxyisolariciresinol-9-O-β-D-xylopyranoside C26H36O11 R2 WP [111]
 186 (+)-5-Methoxyisolariciresinol-9-O-β-D-xylopyranoside C26H36O11 R2 WP [111]
 187 (+)-Lyoniside C27H38O12 R2 WP [111]
 188 Nudiposide C27H38O12 R2 WP [111]
 189 (+)-Lyoniresinol-3α-O-β-D-glucoside C28H38O13 R11 R [33]
Others
 190 Phenylethyl-O-α-L-arabinopyransy-(1 → 6)-O-β-D-glucoside C19H28O10 R8 R [31]
 191 Methylorsellinate C11H14O4 R11 R [51]
 192 Ferulic acid C10H10O4 R11 R [51]
 193 Methyl 2-acetyl-3,5-dihydroxyphenylacetate C11H12O5 R11 R [51]
 194 1-(2-Hydroxy-5-methyl-phenyl)-ethanon C9H10O2 R11 R [51]
 195 Methyl syringate C10H12O5 R11 R [51]
 196 1-(2,4-Dihydroxy-6-methylphenyl)-ethanon C9H10O3 R11 R [51]
 197 4-Hydroxybenzene ethanol C8H10O2 R11 R [51]
 198 Isovanillin C8H8O3 R11 R [51]
 199 p-Coumaricacid-n-eicosanyl ester C31H52O3 R13 S [47]
 200 Z-Octadecyl caffeate C27H44O4 R13 S [47]
 201 Dibutylphthalate C16H22O4 R11 R [132]
 202 2-Methoxyhydroquinone C7H8O3 R11 R [132]
 203 Batiansuanmol C14H18O5 R13 R [138]
 204 Orcinol C7H8O2 R13 R [54]
 205 p-Hydroxybenzoic acid C7H6O3 R1, R9 L, [26, 39]
 206 p-Coumaric acid C9H8O3 R1, R2, R7 L, R, WP, A [39, 48, 134, 144]
 207 Methyl 3,4-dihydroxyphenylpropionate C10H12O4 R1 L [39]
 208 Vanillic acid C8H8O4 R1 L [39]
 209 Isovanillic acid C8H8O4 R1, R7 L, R [39, 48]
 210 Gallic acid C7H6O5 R2, R7, R13 R, [35, 48, 53]
 211 Methyl gallate C8H8O5 R2 R [35]
 212 2,6-Dimethoxy-4-hydroxyl benzoic acid C9H10O5 R9 A [26]
 213 Pyrocatechin C6H6O2 R9 A [145]
 214 Syringic acid C9H10O5 R9 A [145]
 215 3,4-Dihydroxybenzaldehyde C7H6O3 R9 A [145]
 216 Ethyl 3,4-dihydroxybenzoate C9H10O4 R9 A [145]
 217 Ethyl gallate C9H11O4 R9 A [145]
 218 Rumexin C15H20O8 R4 A [38]
 219 Caffeic acid C9H8O4 R4 A [38]
 220 1-O-caffeoylglucose C15H18O9 R4 A [38]
 221 1-Methyl caffeic acid C10H10O4 R4 A [38]
 222 Neochlorogenic acid C16H18O9 R27 L [146]
 223 (S)-4′-Methylnonyl benzoate C17H26O2 R7 A [14]
 224 5-Methoxy-7-hydroxy-1(3H)-benzofuranone C9H8O4 R11 R [51]
 225 5,7-Dihydroxy-1(3H)-benzofuranone C9H6O4 R13 R [53]
 226 5-Methoxyl-1(3H)-benzofuranone-7-glucoside C15H18O9 R8 R [31]
 227 Sinapic acid C11H12O5 R1 FL [147]
 228 Protocatechuic acid C7H6O4 R1 L [55]
 229 p-Hydroxycinnamic acid C9H8O3 R8 R [190]
 230 Streptokordin C8H9NO2 R11 R [132]
 231 Hastatuside A C16H18O9 R2 R [114]
 232 β-Sitosterol C29H50O R1, R6, R7, R11, R13, R28 A, R, S, L, WP [34, 39, 47, 48, 53, 101, 189]
 233 Daucosterol C35H60O6 R1, R7, R8, R13, R28 A, R, F, L [39, 45, 48, 53, 101, 138, 190]
 234 Ergosta-6,22-diene-3,5,8-triol C28H46O3 R21 WP [123]
 235 Nonadecanoic acid-2,3-dihydroxypropyl ester C22H44O4 R13 R [53]
 236 Hexadecanoic acid 2,3-dihydroxypropyl ester C19H38O4 R7 R [48]
 237 1-Stearoylglycerol C21H42O4 R4 A, R [148]
 238 Triacontanol C30H62O R13 S [47]
 239 Dotriacontanol C32H66O R13 S [47]
 240 Hexacosanoic acid C26H52O2 R6, R13 S, WP [34, 47]
 241 Dotriacontane C32H66 R13 S [47]
 242 Glyceryl 1,3-dipalmitate C35H68O5 R13 S [47]
 243 (2E)-8-Hydroxy-2,6-dimethyl-2-octenoic acid C10H18O3 R11 R, [132]
 244 Tetratriacontane C34H70 R13 S [149]
 245 Ceryl alcohol C26H54O R20 A [125]
 246 Oxalic acid C2H2O4 R1 A [56]
 247 Cardozin C10H20O6 R7 R [48]
 248 Succinic acid C4H6O4 R7 R [48]
 249 Sucrose C12H22O11 R8 R [190]
 250 Rebeccamycin C27H21Cl2N3O7 R1 L [9]
 251 Vitamin C C6H8O6 R1 L [9]
 252 Calcium oxalate C2H2O4 Ca R1 L [9]
 253 Tartaric acid C4H6O6 R1 L [9]
 254 β-carotene C40H56 R13, R15 R, L [126, 129]
 255 Lutein C40H56O2 R15, R25 L [95, 126]
 256 Anhydrolutein I C40H54O R25 L [95]
 257 Anhydrolutein II C40H54O R25 L [95]
 258 Riboflavin C17H20N4O6 R13 R [129]
 259 2-O-methyl inositol C7H14O6 R13 A [46]
 260 Stigmasterol C29H48O R13 WP [23]
 261 α-Asarone C12H16O3 R13 WP [23]
 262 7-Hydroxy-5-methoxyphthalide C9H8O4 R11 R [51]
 263 4-Ethyl heptyl benzoate C16H24O2 R26 R [150]
 264 Glucosylceramide C40H77NO8 R12 L [151]
 265 Helonioside A C32H38O17 R7 R [48]
 266 1-O-β-D-(2,4-dihydroxy-6-methoxyphenyl)-6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-glucoside C22H26O13 R1 A [56]
 267 1-O-β-D-(3,5-Dimethoxy-4-hydroxyphenol)-(6-O-galloyl)-glucoside C21H24O13 R11 R [33]
 268 RA-P (Polysaccharide (D-glucose-—-D-arabinose) R1 R [127]

Rh rhizomes, R roots, WP whole plants, T tubers, A the aerial part, S seeds, L leaves, F fruits, S stems, FL flowers

Quinones

Quinones are widely found in Rumex, particularly accumulated in the roots. 56 quinones (Fig. 1) including anthraquinones, anthranones, and seco-anthraquinones and their glycosides and dimers were isolated and identified from more than 17 Rumex species (Table 2). Among them, anthraquinone O- and C- glycosides with glucose, galactose, rhamnose, and 6-hydroxyacetylated glucose as commonly existing sugar moieties, were normally found in Rumex. Three anthraquinones, chrysophanol (1), emodin (8) and physcion (18) are commonly used indicators to evaluate the quality of Rumex plants [22]. Some new molecules were also reported. For example, xanthorin-5-methylether (30) was isolated from R. patientia for the first time [23, 24], and two new antioxidant anthraquinones, obtusifolate A (45) and B (46) were isolated from R. obtusifolius [25].

Fig. 1.

Fig. 1

Structures of quinones (156)

The anthranones often existed in pairs of enantiomers, whose meso-position is commonly connected with a C-glycosyl moiety. The enantiomers, rumejaposides A (21) and B (22), E (25) and F (26), G (27) and H (28) were reported from R. dentatus, R. japonicus, R. nepalensis and R. patientia [2628]. Three hydroxyanthrones, chrysophanol anthrone (7), emodin anthrone (17), physcion anthrone (20), whose C-10 were reduced as an alphatic methylene, were isolated from the roots of R. acetosa for the first time [29], while a new anthrone, rumexone (31) was reported from the roots of R. crispus [30]. Two anthranones, 10-hydroxyaloins A (39) and B (40) were reported from Rumex for the first time [31]. A new 8-ionized hydroxylated 9,10-anthraquinone namely, rumpictusoide A (56) was isolated from the whole plant of R. pictus [183]. Moreover, two new oxanthrone C-glucosides 6-methoxyl-10-hydroxyaloins A (41) and B (42) were isolated from the roots of R. gmelini [32].

Seco-anthraquinones are oxidized anthraquinones with a loop opened at C-10, resulting in the fixed planar structure of anthraquinone destroyed and causing of a steric hindrance between the two left benzene rings. So far, only two seco-anthraquinone glucosides, nepalensides A (49) and B (50) were reported from the roots of R. nepalensis [33].

Flavonoids

Flavonoids are one of the most important bioactive components existing widely in plant kingdom. To date, 57 flavonoids (57113) including flavones, flavanols, chromones and their

glycosides were reported from Rumex (Fig. 2, Table 2). They are mostly derived from kaempferol (63) and quercetin (71) connecting with glucosyl, rhamnosyl, galactosyl and arabinosyl moieties at different positions. For example, kaempferol (63) together with seven glycosides, -3-O-β-D-glucoside (64), -3-O-α-L-rhamnoside (65), -3-O-α-L-rhamnosyl-(1 → 6)-β-D-galactoside(66), -3-O-α-L-arabinosyl-(1 → 6)-β-D-galactoside (67), -3-O-(2''-O-acetyl-α-L-arabinosyl)-(1 → 6)-β-D-galactoside (68), -7-O-β-D-glucoside (69) and -7-O-α-L-rhamnoside (70) [14, 23, 3442], and quercetin (71) together with 11 derivatives, -3-O-β-D-glucoside (72), -3-O-β-D-glucuronide (73), -3-O-β-D-glucosyl(1 → 4)-β-D-galactoside (74), -3-O-α-L-rhamnoside (75), -3-O-α-L-arabinoside (80), -3-O-α-L-arabinosyl-(1 → 6)-β-D-galactoside (81), -3-O-[2''-O-acetyl-α-L-arabinosyl]-(1 → 6)-β-D-galactoside (82), -7-O-β-D-glucoside (83), -7-O-α-L-rhamnoside (84), 3-O-methyl quercetin (97) and -3,3'-dimethylether (113) [14, 23, 27, 35, 37, 38, 4050, 148], were reported from several Rumex plants.

Fig. 2.

Fig. 2

Structures of flavonoids (57–113)

Moreover, a new chromone glucoside, 2,5-dimethyl-7-hydroxychromone-7-O-β-D-glucoside (95) was isolated from the root of R. gmelini [31], and five chromones, 7-hydroxy-2,3-dimethyl-chromone (90), 5-methoxy-7-hydroxy-1(3H)-chromone (91), 5,7-dihydroxy-1(3H)-chromone (92), 2,5-dimethyl-7-hydroxychromone-7-O-β-D-glucoside (95) and 2,5-dimethyl-7-hydroxychromone (96) were reported from R. gmelini, R. nepalensis, R. patientia and R. cristatus [31, 5153].

Catechin (105) and epicatechin (107) are commonly distributed in R. patientia, the roots of R. rechingerianus, the whole plant of R. crispus, and the leaves of R. acetosa [34, 37, 39, 49, 54, 55]. Moreover, a variety of flavan-3-ols, 105, 107, epicatechin-3-O-gallate (110), epigallocatechin-3-O-gallate (111) were isolated from R. acetosa [49, 56].

Tannins

Tannins, which may be involved with the hemostasis activity, are abundant in Rumex plants. So far, 25 condensed tannins (114138) (Fig. 3, Table 2) were reported from the genus Rumex.

Fig. 3.

Fig. 3

Structures of tannins (114–138)

Chemical investigations on the EtOAc fraction of acetone–water extract of the aerial parts of R. acetosa showed that R. acetosa was rich in tannins. Five new condensed tannin dimers, epiafzelechin-(4β → 8)-epicatechin-3-O-gallate (127), cinnamtannin B1-3-O-gallate (132) and epiafzelechin-(4β → 6)-epicatechin-3-O-gallate (135), and trimers, epiafzelechin-(4β → 8)-epicatechin-(4β → 8)-epicatechin (114), and epicatechin-(2β → 7, 4β → 8)-epiafzelechin-(4α → 8)-epicatechin (132), were reported. In addition, some procyanidins and propelargonidins, epiafzelechin-(4β → 8)-epicatechin-(4β → 8)-epicatechin (114), epicatechin-(4β → 8)-epi-catechin-(4β → 8)-catechin (115), procyanidin C1 (116), epicatechin-(4β → 6)-catechin (121), procyanidin B1-B5 (120, 122–125), and epicatechin-(4β → 8)-epicatechin-3-O-gallate (126), were also isolated [56, 107].

Stilbenes

So far, 6 stilbenes have been separated from Rumex (139144) (Fig. 4, Table 2). Resveratrol (139) isolated from R. japonica Houtt was found for the first time from the Polygonaceae family [108]. It has been widely applied in cardiovascular protection and as antioxidation agent [109]. Resveratrol (139), (Z)-resveratrol (140) and polydatin (141) were obtained from Rumex spp. [14, 32, 35, 45, 110, 111]. 5,4'-Dihydroxy-3-methoxystilbene (142), 3,5-dihydroxy-4'-methoxystilbene (143) and 5,4'-dihydroxy-stilbene-3-O-α-arabinoside (144) were separated from the roots of R. bucephalophorus [77].

Fig. 4.

Fig. 4

Structures of stilbenes (139–144) and naphthalenes (145–166)

Naphthalenes

Naphthalenes are also widely distributed in Rumex. At present, 22 naphthalenes including naphthol, α-naphthoquinones and their derivatives have been identified from Rumex (145166) (Fig. 4, Table 2). Nepodin (145) and nepodin-8-O-β-D-glucoside (146) are widespread in Rumex [31, 45, 112, 113]. In addition, 145, nepodin-8-O-β-D-(6'-O-acetyl)-glucoside (147), rumexoside (154), 6-hydroxymusizin-8-O-β-D-glucopyranoside (158) and hastatuside B (164) were isolated from R. hastatus [35, 110, 114]. 2-Methoxystypandrone (152) was isolated from R. japonicus and R. maritimus [115, 116]. Notably, some naphthalenes containing Cl, 2-acetyl-4-chloro-1,8-dihydroxy-3-methylnaphthalene-8-O-β-D-glucoside (155) and patientoside B (156) were isolated from R. patientia [117]. Moreover, 3-acetyl-2-methyl-1,5-dihydroxyl-2,3- epoxynaphthoquinol (153), 3-acetyl-2-methyl-1,4,5-trihydroxyl-2,3-epoxy-naphtho-quinol (159) and 3-acetyl-2-methyl-1,5-dihydroxyl-7-methoxyl-2,3-epoxynaphthoquinol (160), which contain the ethylene oxide part of the structure, were rarely found in Rumex, and they were reported from R. patientia, R. japonicus and R. nepalensis [51, 65, 118, 119]. 4,4''-Binaphthalene-8,8''-O,O-di-β-D-glucoside (157) was isolated from R. patientia [120].

Terpenes

Until now, only six terpenes have been reported from Rumex (Fig. 5, Table 2). Four pentacyclic triterpenes, i.e., tormentic acid (167), myrianthic acid (168) and 2α,3α,19α-trihydroxy-24-norurs-4(23), 12-dien-28-oic acid (169) and (4R)-23-epoxy-2α,3α,19α-trihydroxy-24-norurs-12-en-28-oic acid (170) were obtained from the EtOAc fraction of the stems of R. japonicus. Of them, 169 and 170 were two new 24-norursane type triterpenoids, whose C-12 and C-13 were existed as double bonds [121]. A ursane (α-amyrane) type triterpene, taraxasterol acetate (171) was isolated from R. hastatus. [63]. And lupeol (172) was isolated from the roots of R. nepalensis for the first time [122].

Fig. 5.

Fig. 5

Structures of terpenes (167–172)

Diterpene alkaloids

So far, only three hetisane-type (C-20) diterpene alkaloids, orientinine (7,11,14-trihydroxy-2,13-dioxohetisane, 173), acorientine (6,13,15-trihydroxyhetisane, 174) and panicudine (6-hydroxy-11-deoxy-13-dehydrohetisane, 175) were reported from the aerial part of R. pictus. They might be biosynthesized from tetra- or penta-cyclic diterpenes [75] (Fig. 6, Table 2).

Fig. 6.

Fig. 6

Structures of diterpene alkaloids (173–175)

Lignans

Fourteen lignans (176189) were summarized from Rumex (Fig. 7, Table 2). A new lignan, 3-methoxyarctiin-4''-O-β-D-xyloside (178), and two known ones, arctiin (176) and 3-hydroxy-arctiin (177), were obtained from R. patientia [23]. Six lignan glycosides, schizandriside (183), (-)-isolariciresinol-9-O-β-D-xylopyranoside (184), (-)-5-methoxyisolariciresinol-9-O-β-D-xylopyranoside (185), (+)-5-methoxyisolariciresinol-9-O-β-D-xylopyranoside (186), (+)-lyoniside (187) and nudiposide (188) were reported from R. hastatus for the first time [111].

Fig. 7.

Fig. 7

Structures of lignans (176–189)

Other compounds

Up to now, 79 coumarins, sterides, alkaloids, glycosides and polysaccharide were found in Rumex (190268) (Fig. 8, Table 2). Phenylethyl-O-α-L-arabinopyransy-(1 → 6)-O-β-D-glucoside (190) and 5-methoxyl-1(3H)-benzofuranone-7-glucoside (226) were isolated from R. gmelini for the first time [31]. p-Hydroxybenzoic acid (205), p-coumaric acid (206), methyl 3,4-dihydrophenylpropionate (207), vanillic acid (208) and isovanillic acid (209) were isolated from the leaves of R. acetosa [39]. β-Sitosterol (232) and daucosterol (233) are commonly distributed in R. acetosa, R. chinensis, R. crispus and R. gmelini [31, 34, 39, 101]. 2,6-Dimethoxy-4-hydroxyl benzoic acid (212) was isolated from R. japonicus [26]. Moreover, rumexin (218), caffeic acid (219), 1-O-caffeoylglucose (220) and 1-methyl caffeic acid (221) were isolated from the aerial parts of R. aquatica [38]. Recently, one new compound (S)-4′-methylnonyl benzoate (223) was reported from R. dentatus [14]. Ergosta-6,22-diene-3,5,8-triol (234) was isolated from the EtOAc fraction of R. abyssinicus for the first time [123]. Conventional techniques and supercritical fluid extraction (SFE) were compared and the latter yielded great efficiency of phenolics from the roots of R. acetosa [124].

Fig. 8.

Fig. 8

Structures of other compounds (190–268) (Note:268 not given)

Ceryl alcohol (245) from R. ecklonianus [125], and β-carotene (254) and lutein (255) from R. vesicarius [126] were reported. Moreover, anhydroluteins I (256) and II (257) were separated from R. rugosus together with 255 [95]. From the roots of R. dentatus, helonioside A (265) was isolated for the first time [48]. One new phloroglucinol glycoside 1-O-β-D-(2,4-dihydroxy-6-methoxyphenyl)-6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-glucoside (266) was isolated from R. acetosa [56]. It was the first time that 1-O-β-D-(3,5-dimethoxy-4-hydroxyphenol)-(6-O-galloyl)-glucoside (267) was isolated from R. nepalensis [33].

Rumex polysaccharides have rarely been studied, and only one polysaccharide, RA-P (268), which has a 30 kDa molecular weight and consists of D-glucose and D-arabinose, was reported from R. acetosa [127].

LC–MS analysis

The chemical compositions of Rumex spp. were also analyzed by LC–MS techniques. Untargeted metabolomic profiling via UHPLC-Q-TOF–MS analysis on the flowers and stems of R. tunetanus resulted in the identification of 60 compounds, 18 of which were reported from the Polygonaceae family for the first time. Quercetin-3-O-β-D-glucuronide (73) was found to be the most abundant phenolic compound in flowers and epicatechin-3-O-gallate (110) in stems [103]. Moreover, 44 bioactive components classified as sugars, flavanols, tannins and phenolics were clarified from the flowers and stems of R. algeriensis based on RP-HPLC–DAD-QTOF-MS and MS–MS [102]. The analysis of sex-related differences in phenolics of R. thyrsiflorus has shown female plants of R. thyrsiflorus contain more bioactive components than males, such as phenolic acids and flavonoids, especially catechin (105) [20].

Bioactivity

Rumex has been used as food and medicine in the folk. In addition to important role of Rumex in the traditional application, during the past few decades, it was subjected to scientific investigations of the structure of isolated chemical components and their clinical applications by several research groups. Pharmacological studies on Rumex extracts and its pure components revealed a wide range of bioactivities, involving antimicrobial, anti-inflammatory, antiviral, renal and gastrointestinal protective effects, antioxidant, antitumor and anti-diabetes effects.

Antimicrobial

Bioassay-guided isolation on the whole plants of R. abyssinicus yielded six antimicrobial quinones, chrysophanol (1) and its 8-O-β-D-glucoside (3), emodin (8), 6-hydroxyemodin (14), physcion (18) and its 8-O-β-D-glucoside (19), with MIC values of 8—256 μg/mL [123].

Proanthocyanidin-enriched extract from the aqueous fraction of the acetone–water (7: 3) extract of the aerial parts of R. acetosa (5 μg/mL—15 μg/mL) could interfered with the adhesion of Porphyromonas gingivalis (ATCC 33,277) to KB cells (ATCC CCL-17) both in vitro and in situ. In silico docking assay, a main active constituent from R. acetosa, epiafzelechin-3-O-gallate-(4β → 8)-epicatechin-3-O-gallate (130) exhibited the ability to interact with the active side of Arg-gingipain and the hemagglutinin from P. gingivalis [139].

A bacteriostasis experiment of two naphthalenes, torachrysone (150) and 2-methoxy-stypandrone (152) isolated from R. japonicus roots, showed inhibitory effect on both gram-negative and gram-positive bacteria [152]. The antibacterial (Bacillus subtilis, Escherichia coli, Moraxella catarrhalis, etc.) potential of the n-hexane, chloroform, aqueous fractions of 14 Rumex from Carpathian Basin (R. acetosella, R. acetosa, R. alpinus, R. aquaticus, R. crispus, R. patientia, R. pulcher, R. conglomeratus, R. thyrsiflorus, etc.) were investigated by the disc diffusion method. It showed that the n-hexane and chloroform fractions of roots of R. acetosa, R. alpinus, R. aquaticus, R. conglomeratus and R. patientia exhibited stronger activity against bacteria (inhibition zones > 15 mm). Naphthalenes (145, 146, 151, 152) exhibited antibacterial capacity against several bacterial strains (MIC = 48—57.8 μM, in case of M. catarrhalis; MIC = 96—529.1 μM, in case of B. subtilis) than anthraquinones (1, 3, 8, 12, 14, 18), flavonoids (62, 71, 80, 105, 112, 113), stilbenes (139, 141) and 1-stearoylglycerol (237), etc., which were isolated from R. aquaticus [148].

Antimicrobial study demonstrated that R. crispus and R. sanguineus have the potential for wound healing due to their anti-Acinetobacter baumannii activities (MIC = 1.0—2.0 mg/mL, R. crispus; 1.0—2.8 mg/mL, aerial parts of R. sanguineus; 1.4—4.0 mg/mL, roots of R. sanguineus) [106].

Anti-inflammatory

The potential effects of anti-inflammatory of AST2017-01 composing of processed R. crispus and Cordyceps militaris which was widely used in folk medicines in Korea, as well as chrysophanol (1) on the treatment of ovalbumin-induced allergic rhinitis (AR) rats were investigated. The serum and tissue nasal mucosa levels of IgE, histamine, TSLP, TNF-α, IL-1, IL-4, IL-5 and IL-13 were both decreased by treatment with AST2017-01 and 1 (positive control: dexamethasone), indicating that R. crispus and 1 has the ability to prevent and treat AR [153]. The aqueous extract of roots of R. patientia has anti-inflammatory action in vivo. The higher dose of extract (150 mg/kg) showed inhibition (41.7%) of edema in rats compared with the positive control, indomethacin (10 mg/kg, 36.6%) [21]. Methanolic extracts of the roots and stems of R. roseus exhibited anti-inflammatory functions in intestinal epithelial cells, reducing TNF-α-induced gene expression of IL-6 and IL-8 [154].

The ethanol extract of the roots of R. japonicus could be a therapeutic agent for atopic dermatitis. Skin inflammation in Balb/c mice was alleviated with the extract in vivo. Moreover, an in vitro experiment showed that the extract of R. japonicus decreased the phosphorylation of MAPK and stimulated NF-κB in TNF-α in HaCaT cells [155]. The methanolic extract of R. japonicus inhibited dextran sulfate sodium (DSS)-induced colitis in C57BL/6 N mice by protecting tight junction connections in the colonic tissue. It was observed that R. japonicus has the potential to treat colitis [156]. Ethyl acetate extract of the roots of R. crispus showed anti-inflammatory activity in inhibiting NO production and decreasing the secretion of proinflammatory cytokines [157].

Antivirus

1,4-Naphthoquinone and naphthalenes from R. aquaticus presented antiviral activity against herpes simplex virus type 2 (HSV-2) replication infected Vero cells. In which, musizin (145) showed dose dependent inhibitory property, causing a 2.00 log10 reduction in HSV-2 at 6.25 μM, on a traditional virus yield reduction test and qPCR assay. It suggested that R. aquaticus had the potential to treat HSV-2 infected patients [158].

Acetone–water extract (R2, which contains oligomeric, polymeric proanthocyanidins and flavonoids) from the aerial parts of R. acetosa showed obvious antiviral activities via plaque reduction test and MTT assay on Vero cells. R2 was 100% against herpes simplex virus type-1 at concentrations > 1 μg/mL (IC50 = 0.8 ± 0.04 μg/mL). At concentrations > 25 μg/mL (CC50 = 78.6 ± 12.7 μg/mL), cell vitality was more than 100% reduced by R2 [107].

The function in kidney and gastrointestinal tract

It is noted that quercetin-3-O-β-D-glucoside (72, QGC) from R. aquaticus could alleviate the modle that indomethacin (nonsteroidal anti-inflammatory drugs) induced gastric damage of rats and ethanol extract of R. aquaticus had a protective effect on the inflammation of gastric epithelial cells caused by Helicobacter pylori. In vivo research suggested that QGC pretreatment could decrease gastric damage by increasing mucus secretion, downregulating the expression of intercellular adhesion molecule-1 and decreasing the activity of myeloperoxidase. The in vitro test found that flavonoids including QGC could inhibit proinflammatory cytokine expression and inhibit the proliferation of an adenocarcinoma gastric cell line (AGS) [159, 160]. The cytoprotective effect of QGC against hydrogen peroxide-induced oxidative stress was noticed in AGS [161]. Moreover, QGC also showed protective efficiency in a rat reflux esophagitis model in a dose-dependent manner (1—30 mg/kg) [162].

Ten anthraquinones chrysophanol (1), chrysophanol-8-O-β-D-glucoside (3), 6'-acetyl-chrysophanol-8-O-β-D-glucoside (6), emodin (8), emodin-8-O-β-D-glucoside (12), physcion (18), aloe-emodin (13), rumexpatientosides A (47) and B (48) and nepalenside A (49) from R. patientia, R. nepalensis, R. hastatus not only inhibited the secretion of IL-6, but also decreased collagen IV and fibronectin production at a concentration of 10 µM in vitro. On which concentration, they were nontoxic to cells [133]. It suggested that anthraquinones have great potential to treat kidney disease.

Antioxidant properties

An extraction technology to obtain the total phenolics of R. acetosa was optimized and the antioxidant activity of different plant parts of R. acetosa was well investigated. It was found that the 80% methanol extract of the roots (IC50 = 118.8 μM) showed higher scavenging activity to DPPH free radicals than the other parts (leaves: IC50 = 201.6 μM, flowers and fruits: IC50 = 230.1 μM, stems: IC50 = 411.2 μM) [163]. The roots of R. thyrsiflorus [164], ethanol extracts of R. obtusifolius and R. crispus showed antioxidant ability on DPPH, ABTS+ and FRAP assays [165]. Moreover, R. tingitanus leaves, R. dentatus, R. rothschildianus leaves, R. roseus and R. vesicarius also showed antioxidant activity on DPPH assay [13, 78, 105, 154, 166, 167]. Phenolics isolated from R. tunetanus flowers and stems displayed antioxidant properties on DPPH and FRAP assays [103]. DPPH, ABTS+, NO2 radical scavenging and phosphomolybdate antioxidant assays verified that R. acetosella has antioxidant properties [168]. Phenolic constitutions from R. maderensis dispalyed antioxidant activity after the gastrointestinal digestion process. These components are known as dietary polyphenols and have the potential to be developed as functional products [99].

Moreover, the total antioxidant capacities of R. crispus were found to be 49.4%—86.4% on DPPH, ABTS+, NO, phosphomolybdate and SPF assays, which provided the basis to develop R. crispus as antioxidant, antiaging and skin care products [169]. Later on, the ripe fruits of R. crispus were studied and the aqueous extract showed antioxidant activity in vitro [170]. Dichloromethane and ethyl acetate extracts of R. crispus exhibited stronger antioxidant activity, which were associated with the concentration of polyphenols and flavonoids [157]. The antioxidant activities of chrysophanol (1), 1,3,7-trihydroxy-6-methylanthraquinone (54), przewalskinone B (55) and p-coumaric acid (206) isolated from R. hastatus were investigated on a nitric oxide radical scavenging assay, whose IC50 values were 0.39, 0.47, 0.45, and 0.45 mM, respectively [134].

Antitumor properties

MTT assays on HeLa (human cervical carcinoma), A431 (skin epidermoid carcinoma) and MCF7 (human breast adenocarcinoma) cell lines showed that R. acetosa and R. thyrsiflorus could inhibit the tumor cell proliferation [171]. The fruit of R. crispus showed cytotoxicity on HeLa, MCF7 and HT-29 (colon adenocarcinoma) cells in vitro [170]. The methanolic extract of R. vesicarius was assessed for hepatoprotective effects in vitro. CCl4-induced hepatotoxicity was observed at 100 mg/kg bw and 200 mg/kg bw. The plant also has cytotoxicity in HepG2 (human hepatoma cancer) cell lines [172]. Dichloromethane extract of R. crispus roots inhibited the growth and induced cellular apoptosis of HepG2 cells [157]. The hexane fraction of R. rothschildianus leaves showed 98.9% and 97.4% inhibition of HeLa cells and MCF7 cells at a concentration of 4 mg/mL [105].

Different plant parts (stems, roots, flowers and leaves) of R. vesicarius were screened for their cytotoxicity by the MTS method on MCF7, Lovo and Caco-2 (human colon cancer), and HepG2 cell lines. The stems displayed stronger cytotoxicity in vitro and with nontoxicity on zebrafish development, with IC50 values of 33.45—62.56 μM. At a concentration of 30 µg/mL, the chloroform extract of the stems inhibited the formation of  ≥ 70% of intersegmental blood vessels and 100% of subintestinal vein blood vessels when treated zebrafish embryos, indicating the chloroform extract of R. vesicarius stems has apparent antitumor potential [15].

2-Methoxystypandrone (152) from R. japonicus exhibited antiproliferative effect on Jurkat cells and the potential to treat leukemia, by reducing the mitochondrial membrane potential and increasing the accumulation of mitochondrial reactive oxygen, as shown by flow cytometry [116]. The phenolic extract from the flower parts of R. acetosa exhibited in vitro antiproliferative effects on HaCaT cells. When increasing of the extract concentration from 25 μg/mL to 100 μg/mL, the proliferation ability on HaCaT cells gradually decreased [147].

Antidiabetes activities

Chrysophanol (1) and physcion (18) from the roots of R. crispus showed inhibition on α-glucosidase, with IC50 values of 20.1 and 18.9 μM, respectively [180]. The alcohol extract of R. acetosella displayed stronger inhibitory activity on α-glucosidase (roots, IC50 = 12.3 μM; aerial parts, IC50 < 10 μM), compared to the positive control, acarbose (IC50 = 605 μM, p < 0.05), revealing R. acetosella could be developed as an antidiabetic agent [168]. Moreover, the methanolic extract of R. lunaria leaves displayed remarkable kinetic of -α-glucosidase activity from the concentration of 3 μM by comparison with blank control [16], and the acetone fraction of R. rothschildianus leaves showed inhibitory activity against α-amylase and α-glucosidase (IC50 = 19.1 ± 0.7 μM and 54.9 ± 0.3 μM, respectively) compared to acarbose (IC50 = 28.8, 37.1 ± 0.3 μM, respectively) [105].

The hypoglycemic effects of oral administration of ethanol extract of R. obtusifolius seeds (treatment group) were compared to the control group (rabbits with hyperglycemia). The treatment group could decrease fasting glucose levels (57.3%, p < 0.05), improve glucose tolerance and increase the content of liver glycogen (1.5-fold, p < 0.01). It also not only reduced the total cholesterol, low-density lipoprotein cholesterol levels and liver enzyme levels, but increased the high-density lipoprotein cholesterol levels. The results showed that R. obtusifolius has great potential to treat diabetes [173]. In addition, phenolic components of R. dentatus showed the ability to ameliorate hyperglycemia by modulating carbohydrate metabolism in the liver and oxidative stress levels and upregulating PPARγ in diabetic rats [14].

Other biological activities

The vasorelaxant antihypertensive mechanism of R. acetosa was investigated in vivo and in vitro. Intravenous injection (50 mg/kg) of the methanol extract of R. acetosa (Ra.Cr) leaves caused a mean arterial pressure (MAP) (40 mmHg) in normotensive rats with a decrease of 27.88 ± 4.55% and a MAP (70 mmHg) in hypertensive rats with a decrease of 48.40 ± 4.93%. In endothelium intact rat aortic rings precontracted with phenylephrine (1 μM), Ra.Cr induced endothelium-dependent vasorelaxation with EC50 = 0.32 mg/mL (0.21—0.42), while in denuded endothelial rat aortic rings, EC50 = 4.22 mg/mL (3.2—5.42), which was partially blocked with L-NAME (10 μM), indomethacin (1 μM) and atropine (1 μM). In isolated rabbit aortic rings precontracted with phenylephrine (1 μM) and K+ (80 mM), Ra.Cr induces vasorelaxation and the movement of Ca2+ [174].

The acetone extract of R. japonicus showed protective activity against myocardial apoptosis, through the regulation of oxidative stress levels in cardiomyocytes (LDH, MDA, CK, SOD) and the suppression of the expression of apoptosis proteins (caspase-3, Bax, Bcl-2) on in vitro H2O2-induced myocardial H9c2 cell apoptosis [175].

The antiplatelet activity of R. acetosa and the protective mechanism on cardiovascular system were investigated yet. The extract of R. acetosa showed inhibition of the collagen-induced platelet aggregation by modulating the phosphorylation of MAPK, PI3K/Akt, and Src family kinases and inhibited the ATP release in a dose dependent manner (25—200 μg/mL) [176]. The absorption of fexofenadine was inhibited by the ethanol extract of R. acetosa to decrease the aqueous solubility of fexofenadine [177]. The hepatoprotective effect of R. tingitanus was investigated by an in vivo experiment, in which the ethanol extract protected effectively the CCl4-damaged rats by enhancing the activity of liver antioxidant enzymes. Moreover, the extract could reduce the immobility time of mice, comparable of the positive drug, clomipramine. The results indicated that R. tingitanus has antidepressant-like effects [78].

Stimulating the ERK/Runx2 signaling pathway and related transcription factors could induce the differentiation of osteoblasts. Fortunately, chrysophanol (1), emodin (8) and physcion (18) from the aqueous extract of R. crispus could suppress the RANKL-induced osteoclast differentiation by suppressing the MAPK/NF-κB/NFATc1 signaling axis and increas the inhibitory factors of NFATc1 [178].

Moreover, the ethanol extract of R. crispus could reduce the degradation of collagen by inhibiting matrix metalloproteinase (MMP-1, MMP-8, MMP-13), indicating that R. crispus exhibited the antiaging function [169].

The anti-Alzheimer effect of helminthosporin (51) from R. abyssinicus was investigated in PAMPA-BBB permeability research, showing that 51 inhibited obviously AChE and BChE with IC50 values < 3 μM. Compound 51 could not only cross the BBB with high BBB permeability, but also bind with the peripheral anion part of the cholinesterase activity site by molecular docking [80].

It is noted, R. crispus, a traditional medicinal herb in the folk with rich retinol, ascorbic acid and α-tocopherol in the leaves, could be used as a complementary diet [179]. Moreover, chrysophanol (1) and physcion (18) from R. crispus roots showed obvious inhibitory activity on xanthine oxidase (IC50 = 36.4, 45.0 μg/mL, respectively) [180].

Inhibition of human pancreatic lipase could reduce the hydrolysis of triacylglycerol into monoacylglycerol and free fatty acids [181]. Chrysophanol (1) and physcion (18) from R. nepalensis with good inhibitory activity on pancreatic lipase (Pearson's r = 0.801 and 0.755, respectively) showed the obvious potential to treat obesity [182].

Conclusion

The genus Rumex distributing widely in the world with more than 200 species has a long history of food and medicinal application in the folk. These plants with rich secondary metabolites, e.g., quinones, flavonoids, tannins, stilbenes, naphthalenes, terpenes, diterpene alkaloids, lignans and other type of components, showed various pharmacological activities, such as antimicrobial, anti-inflammatory, antiviral, renal and gastrointestinal protective effects, antioxidant, antitumor and anti-diabetes effects. Particularly, quinones as the major components in Rumex showed stronger antibacterial activities and exerted the potential to treat kidney disease. However, detailed phytochemical studies are needed for many Rumex species, in order to clarify their bioactive components. Further studies and application may focus on the antitumor, anti-diabetes, anti-microbial, hepatoprotective, cardiovascular and gastrointestinal protective effects. Moreover, the toxicity or side effects for Rumex plants and their chemical constituents should be evaluated, in order to make the uses of Rumex more safety.

Acknowledgements

This work was supported by the Ministry of Science and Technology, China (2021YFE0103600) for International Scientific and Technological Innovative Cooperation between Governments.

Abbreviations

AChE

Acetylcholinesterase

AGS

Adenocarcinoma gastric cell line

AR

Allergic rhinitis

BBB

Blood-brain barrier

BChE

Butyrylcholinesterase

EtOAc

Ethyl acetate

HPLC

High performance liquid chromatograph

IL

Interleukin

UHPLC-Q-TOF-MS

Ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry

MAPK

Mitogen-activated protein kinase

MIC

Minimum inhibitory concentration

MS

Mass Spectrometry

MTT

3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide

NF-κB

Nuclear factor-kappa B

QGC

Quercetin-3-O-β-D-glucoside

TNF-α

Tumor necrosis factor-α

Author contributions

J-J L, Y-X L, H-T Z, DW collected the related references; J-J L worte the manuscript; NL and Y-J Z reviewed and edited the manuscript. All authors read and approved the final manuscript.

Declarations

Competing interests

The authors declare no conflict of interest.

Footnotes

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

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