Flavonoids of the Caryophyllaceae

Springer Science and Business Media LLC - Tập 21 - Trang 179-218 - 2021
Katarzyna Jakimiuk1, Michael Wink2, Michał Tomczyk1
1Department of Pharmacognosy, Faculty of Pharmacy with the Division of Laboratory Medicine, Medical University of Białystok, Białystok, Poland
2Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg, Germany

Tóm tắt

The plant family Caryophyllaceae, commonly known as the pink family, is divided into 3 subfamilies and contains over 80 genera with more than 2600 species that are widely distributed in temperate climate zones. Plants belonging to this family produce a variety of secondary metabolites important in an ecological context; however, some of these metabolites also show health-promoting activities. The most important classes of phytochemicals include saponins, phytoecdysteroids, other sterols, flavonoids, lignans, other polyphenols, essential oils, and N-containing compounds such as vitamins, alkaloids or cyclopeptides. Flavonoids are polyphenolic compounds that remain one of the most extensively studied constituents of the Caryophyllaceae family. Numerous structurally diverse aglycones, including flavones, flavonols, flavonones (dihydroflavones), flavonols, isoflavones, and their O- or C-glycosides, exhibit multiple interesting biological and pharmacological activities, such as antioxidant, anti-inflammatory, anti-oedemic, antimicrobial, and immunomodulatory effects. Thus, this review analysed the flavonoid composition of 26 different genera and more than 120 species of Caryophyllaceae for the first time.

Tài liệu tham khảo

Adjadj M, Baghiani A, Boumerfeg S, Noureddine C, Khennouf S, Arrar L, Mubarak MS (2015) Protective effect of Paronychia argentea L. on acetic acid induced ulcerative colitis in mice by regulating antioxidant parameters and inflammatory markers. Wulfenia J 22:148–172 Ahmad V, Ali Z, Ali M, Zahid M (1998) Chemical constituents of Silene conoidea. Fitoterapia 69:406–408 Aldhebiani AY, Mufarah N (2017) Phytochemical screening of some wild plants from Wadi Yalmlam, Saudi Arabia. IOSR J Pharm Biol Sci 12:25–27 Ali Z, Ahmad VU, Ali MS, Iqbal F, Zahid M, Alam N (1999) Two new C-glycosylflavones from Silene conoidea. Nat Prod Lett 13:121–129 Allaoua Z, Benkhaled M, Dibi A, Long C, Aberkane MC, Bouzidi S, Haba H (2016) Chemical composition, antioxidant and antibacterial properties of Pteranthus dichotomus from Algerian Sahara. Nat Prod Res 30:700–704 Al-Snafi AE (2017) Chemical contents and medical importance of Dianthus caryophyllus—a review. ISOR J Pharm 7:61–71 Altay A (2018) HPLC Analysis of phenolic compounds from Gypsophila aucheri Boiss. and investigation of antioxidant and cytotoxic activity of Gypsophila aucheri Boiss. extracts. J Sci Technol 11:168–181 Altay A, Degirmenci S, Korkmaz M, Cankaya M, Koksal E (2018) In vitro evaluation of antioxidant and anti-proliferative activities of Gypsophila sphaerocephala (Caryophyllaceae) extracts together with their phenolic profiles. J Food Meas Charact 12:2936–2945 Altay A, Tohma H, Durmaz L, Taslimi P, Korkmaz M, Gulcin I, Koksal E (2019) Preliminary phytochemical analysis and evaluation of in vitro antioxidant, antiproliferative, antidiabetic, and anticholinergics effects of endemic Gypsophila taxa from Turkey. J Food Biochem 43:1–11 Amosova EN, Zueva EP, Lopatina KA, Safonova EA, Razina TG, Rybalkina OY, Zibareva LN (2019) Influence of Lychnis chalcedonica L. flavonoids on transplanted tumor development and cytostatic therapy effectiveness in mice. Pharm Chem J 53:454–457 Ancheeva E, Daletos G, Muharini R, Lin WH, Teslov L, Proksch P (2015) Flavonoids from Stellaria nemorum and Stellaria holostea. Nat Prod Commun 10:437–440 Atkinson C, Compston JE, Day NE, Dowsett M, Bingham SA (2004) The effects of phytoestrogen isoflavones on bone density in women: a double-blind, randomized, placebo-controlled trial. Am J Clin Nutr 79:326–333 Atta EM, Nassar AA, Hasan NM, Hasa AR (2013) New flavonoid glycoside and pharmacological activities of Pteranthus dichotomus forssk. Rec Nat Prod 7:69–79 Avunduk S, Lacaille-Dubois MA, Miyamoto T, Bedir E, Şenol SG, Çalişkan ÖA (2007) Chionaeosides A-D, triterpene saponins from Paronychia chionaea. J Nat Prod 70:1830–1833 Azadi B, Sohrabi Y (2014) Chemical composition of Silene morganae Freyn volatile oil. Nat Prod Res 29:791–794 Baeva RT, Karryev MO, Litvinenko VI, Abubacirov NK (1975) Glycosides of Vaccaria segetalis V. Vaccarin. Chem Nat Compd 10:182–186 Bahar A, Mubashir HM, Shamshir K (2008) Lychnis coronaria Linn. A review. Nat Prod Indian J 4:22–25 Bakroglu A, Kökten K, Kavurmaci Z (2014) Tannin, protein contents and fatty acid compositions of Silene compacta Fische seeds from Bingöl, Turkey. Turk J Agric Nat Sci 1:441–444 Balamurugan K, Sakthidevi G, Mohan VR (2013) Antiulcer activity of Polycarpaea corymbosa (L.) Lam. whole plant extracts (Caryophyllaceae). Int J Biol Med Res 4:3379–3382 Balsevich JJ, Ramirez-Erosa I, Hickie RA, Dunlop DM, Bishop GG, Deibert LK (2011) Antiproliferative activity of Saponaria vaccaria constituents and related compounds. Fitoterapia 83:170–181 Baruah CC, Pal SK, Baruah AG, Roy JD, Buragohain B, Bora RS, Lahon LC (2009) Analgesic activity of methanolic extract of Drymaria cordata Willd Caryophyllaceae. Pharmacologyonline 2:470–476 Bathori M, Varga E, Szendrei K, Lafont R (1990) Isolation and identification of new edcysteroids from the Caryophyllaceae. J Nat Prod 5:279–293 Báthori M, Lafont R, Girault JP, Máthé I (2001) Structural diversity of ecdysteroids of Lychnis flos-cuculi. Acta Pharm Hung 71:157–167 Bechlem H, Mencherini T, Bouheroum M, Benayache S, Cotugno R, Braca A, De Tommasi N (2017) New constituents from Gymnocarpos decander. Planta Med 83:1200–1206 Blaut M, Schoefer L, Braune A (2003) Transformation of flavonoids by intestinal microorganisms. Int J Vitam Nutr Res 73:79–87 Boguslavskaya LI (1976) Phenolic compounds of Dianthus platycodon. Chem Nat Compd 12:485 Boguslavskaya LI, Dem’yanenko SI, Salam DK (1983) Flavonoids of some species of the genus Dianthus. Khimiya Prirodnykh Soedineni 61:366 Boguslavskaya LI, Tikhonov AI, Pashnev PD, Zhemal B, Sklyar VI (1985a) C-glycosides of Stellaria holostea. Khim Prir Soedin 21:385 Boguslavskaya LI, Tikhonov AI, Pashnev PD, Jemal B, Sklyar VI (1985b) Flavonoid compounds of Herniaria polygama. Chem Nat Compd 21:386–411 Böttger S, Melzig MF (2011) Triterpenoid saponins of the Caryophyllaceae and Illecebraceae family. Phytochem Lett 4:59–68 Bouillant ML, de Arce FF, Favre-Bonvin J, Chopin J, Zoll A, Mathieu G (1979) Nouvelles C-glycosylflavones extraites de Spergularia rubra. Phytochemistry 18:1043–1047 Braca A, Bader A, Siciliano T, De Tommasi N (2008) Secondary metabolites from Paronychia argentea. Magn Reson Chem 46:88–93 Bracher F, Puzik A (2004) β-Carboline Alkaloids 9 [1]. Total synthesis of the β-carboline alkaloids arenarine A and (±)-arenarine B. J Heterocycl Chem 41:173–176 Brahmachari G, Gorai D (2006) Progress in the research on naturally occurring flavones and flavonols: an overview. Curr Org Chem 10:873–898 Brockington SF, Walker RH, Glover BJ, Soltis PS, Soltis DE (2011) Complex pigment evolution in the Caryophyllales. New Phytol 190:854–864 Bustamante-Rangel M, Delgado-Zamarreňo MM, Pèrez-Martin L, Rodriguez-Gonzalo E, Dominguez-Alvarez J (2018) Analysis of isoflavones in foods. Compr Rev Food Sci Food Saf 17:391–411 Cambie RC (1959) Identity of isovitexin (“homovitexin”) and saponaretin. Chem Ind 1959:87–88 Cheikh-Ali S, Farman M, Lacaille-Dubois MA, Semmar N (2019) Structural organization of saponins in Caryophyllaceae. Phytochem Rev 18:405–441 Chen Q, Luo JG, Kong LY (2010a) Triterpenoid saponins from Gypsophila altissima L. Chem Pharm Bull 58:412–414 Chen YF, Kuo PC, Chan HH, Kuo IJ, Lin FW, Su CR, Wu TS (2010b) β-carboline alkaloids from Stellaria dichotoma var. lanceolata and their anti-inflammatory activity. J Nat Prod 73:1993–1998 Chen R, Qi QL, Wang MT, Li QY (2016) Therapeutic potential of naringin: an overview. Pharm Biol 54:3203–3210 Cheng YX, Zhou J, Tan NH, Teng RW, Lu Y, Wang C, Zheng QT (2002) Isolation and characterization of brachystemidines A-E, novel alkaloids from Brachystemma calycinum. J Nat Prod 65:750–752 Cheriti A, Sekkoum K (1996) Flavonoids from Herniaria mauritanica. Indian J Pharm Sci 58:203–204 Cho HJ, Park JHY (2013) Kaempferol induces cell cycle arrest in HT-29 human colon cancer cells. J Cancer Prev 18:257–263 Cho JY, Kim MS, Lee YG, Jeong HY, Lee HJ, Ham KS, Moon JH (2016) A phenyl lipid alkaloid and flavone C-diglucosides from Spergularia marina. Food Sci Biotechnol 25:63–69 Chopin MJ, Bouillant ML, Wagner H, Galle K (1974) Endgültige struktur von schaftosid aus Silene schafta. Phytochemistry 13:2583–2586 Chou S, Everngam MC, Beck JJ (2008) Allelochemical phenolic acids from Gypsophila paniculata. J Undergraduate Chem Res 7:2–4 Clarkson TB (2002) Soy, soy phytoestrogens and cardiovascular disease. J Nutr 132:566S-569S Cook NC, Samman S (1996) Flavonoids—chemistry, metabolism, cardioprotective effects, and dietary sources. Nutritional Biochemistry 7:66–76 Cosme P, Rodríguez AB, Espino J, Garrido M (2020) Plant phenolics: bioavailability as a key determinant of their potential health-promoting applications. Antioxidants 9:1–20 Crozier A, Del Rio D, Clifford MN (2010) Bioavailability of dietary flavonoids and phenolic compounds. Mol Aspects Med 31:446–467 Cui YL, Shen N, Zhao JQ, Dang J (2017a) Phytochemical constituents of Arenaria kansuensis. Chem Nat Compd 53:1002–1004 Cui Y, Shen N, Yuan X, Dang J, Shao Y, Mei L, Liu Z (2017b) Two-dimensional chromatography based on on-line HPLC-DPPH bioactivity-guided assay for the preparative isolation of analogue antioxidant compound from Arenaria kansuensis. J Chromatogr B 1046:81–86 Cui Y, Tao Y, Wang S (2018) Antihypoxic activities of constituents from Arenaria kansuensis. Phytomedicine 38:175–182 Cui Y, Shao Y, Wang Q, Mei L, Tao Y (2019) Purification of flavonolignan diastereoisomers from Arenaria kansuensis by two-dimensional liquid chromatography combined with solid-phase extraction. J Chromatogr Sci 57:1–8 Curir P, Dolci M, Lanzotti V, Taglialatela-Scafati O (2001) Kaempferide triglycoside: A possible factor of resistance of carnation (Dianthus caryophyllus) to Fusarium oxysporum f. sp. dianthi. Phytochemistry 56:717–721 Curir P, Lanzotti V, Dolci M, Dolci P, Pasini C, Tollin G (2003) Purification and properties of a new S-adenosyl-L-methionine: flavonoid 4′-O-methyltransferase from carnation (Dianthus caryophyllus L.). Eur J Biochem 270:3422–3431 Curir P, Dolci M, Galeotti F (2005) A phytoalexin-like flavonol involved in the carnation (Dianthus caryophyllus)—Fusarium oxysporum f. sp. dianthi pathosystem. J Phytopathol 153:65–67 Dai J, Dan W, Schneider U, Wang J (2018) β-Carboline alkaloid monomers and dimers: occurrence, structural diversity, and biological activities. Eur J Med Chem 157:622–656 Darmograi VN (1977) Flavonoids of plants of the genera Silene and Otites adans, family Caryophyllaceae. Chem Nat Compd 13:102–103 Darmograi VN (1979) Flavonoids of some species of the genera Arenaria and Cerastium. Khim Prir Soedin 1:93255 de Andrade Teles RB, Diniz TC, Pinto TCC, de Oliveira Júnior RG, Silva MG, de Lavor EM, Fernandes AWC, de Oliveira AP, de Almeida Ribeiro FPR, da Silva AAM, Cavalcante TCF, Quintans Júnior LJ, da Silva Almeida JRG (2018) Flavonoids as therapeutic agents in Alzheimer’s and Parkinson’s diseases: a systematic review of preclinical evidences. Oxid Med Cell Longev 21:1–21 del Valle JC, Buide ML, Casimiro-Soriguer I, Whittall JB, Narbona E (2015) On flavonoid accumulation in different plant parts: Variation patterns among individuals and populations in the shore campion (Silene littorea). Front Plant Sci 6:1–13 Devkota HP, Fukusako K, Ishiguro K, Yahara S (2013) Flavone C-glycosides from Lychnis senno and their antioxidative activity. Nat Prod Commun 8:1413–1414 Dhanya R, Arun KB, Nisha VM, Syama HP, Nisha P, Santhosh Kumar TR, Jayamurthy P (2015) Preconditioning L6 muscle cells with naringin amelio-rates oxidative stress and increases glucose uptake. PLoS ONE 10:e0132429 Di Lorenzo Ch, Colombo F, Biella S, Stockley C, Restani P (2021) Polyphenols and human health: the role of bioavailability. Nutriens 13:1–30 Dinan L, Balducci C, Guibout L, Lafont R (2020) Small-scale analysis of phytoecdysteroids in seeds by HPLCDAD-MS for the identification and quantification of specific analogues, dereplication and chemotaxonomy. Phytochem Anal 31:1–19 Ding Z, Zhou J, Tan N (1999) A novel flavonoid glycoside from Drymaria diandra. Planta Med 65:578–579 Ding Z, Zhou J, Tan N, Teng R (2000) Two new cyclic peptides from Drymaria diandra. Planta Med 66:386–388 Ding ZT, Yang XQ, Cao QE, Li F (2005) Three new flavone glycosides from Drymaria diandra Bl. J Integr Plant Biol 47:1140–1144 Dong Q, Huang Y, Qiao S (2007) Studies on chemical constituents from Stellaria media. Chin Mater Med 32:1048–1051 Dötterl S, Jürgens A (2005) Spatial fragrance patterns in flowers of Silene latifolia: Lilac compounds as olfactory nectar guides? Plant Syst Evol 255:99–109 Dubois M, Zoll A, Bouillant M, Delaveau P (1982) Di-C-Glycosylflavones du Cerastium arvense ssp. arvense nouvelles pour les Caryophyllaceae. Planta Med 46:56–57 Dubois MA, Zoll A, Chopin J (1983) 7,2″-di-O-Glycosyl-6-C-glycosylflavones from Cerastium arvense. Phytochemistry 22:2879–2880 Dubois MA, Zoll A, Markham KR, Bouillant ML, Dellamonica G, Chopin J (1984) 6-C-β-D-glucopyranosyl-8-C-β-D-galactopyranosylapigenin from Cerastium arvense. Phytochemistry 23:706–707 Dubois MA, Zoll A, Chopin J (1985) Isomollupentin-O-glucosides from Cerastium arvense. Phytochemistry 24:1077–1080 Egert S, Bosy-Westphal A, Seiberl J, Kurbitz C, Settler U, Plachta-Danielzik S, Wagner AE, Frank J, Schrezenmeir J, Rimbach G, Wolffram S, Müller MJ (2009) Quercetin reduces systolic blood pressure and plasma oxidised low-density lipoprotein concentrations in overweight subjects with a high-cardiovascular disease risk phenotype: a double-blinded, placebo-controlled cross-over study. Br J Nutr 7:1065–1074 El Mabruki K, Klemper AV, Kaukhova IE, Sorokin VV (2014) Establishment of rupturewort (Herniaria glabra) herb identity characterestics and quality indices. Pharmacia 6:21–24 Elbandy M, Miyamoto T, Lacaille-Dubois MA (2007) Sulfated lupane triterpene derivatives and a flavone C-glycoside from Gypsophila repens. Chem Pharm Bull 55:808–811 El-Dien OG, Shawky E, Aly AH, Abdallah RM, Abdel-Salam NA (2013) A validated high-performance thin-layer chromatography (HPTLC) method for the quantitative determination of tricin in two Spergularia Species. Am J Anal Chem 4:668–673 Elgamal MHA, Soliman HSM, Karawya MS, Mikhova B, Duddeck H (1995) Isolation of triterpene saponins from Gypsophila capillaris. Phytochemistry 38:1481–1485 Elhagali G, Abozeed A, Abdelnaser K, Youssif Y (2019) Investigation of bioactive constituents and biological activities of different fractions from Herniaria hemistemon. J Gay Al-Azhar Bull Sci 30:67–80 El-Hawary SS, Mubarek MM, Lotfy AR, Hassan AR, Sobeh M, Okba MM (2020) Validation of antidiabetic potential of Gymnocarpos decandrus Forssk. Nat Prod Res 13:1–6 Ferreres F, Gil-Izquierdo A, Vinholes J, Grosso C, Valentão P, Andrade PB (2011) Approach to the study of C-glycosyl flavones acylated with aliphatic and aromatic acids from Spergularia rubra by high-performance liquid chromatography-photodiode array detection/electrospray ionization multi-stage mass spectrometry. Rapid Commun Mass Spectrom 25:700–712 Fukui Y, Tanaka Y, Kusumi T, Iwashita T, Nomoto K (2003) A rationale for the shift in colour towards blue in transgenic carnation flowers expressing the flavonoid 3′,5′-hydroxylase gene. Phytochemistry 63:15–23 Galeotti F, Barile E, Curir P, Dolci M, Lanzotti V (2008a) Flavonoids from carnation (Dianthus caryophyllus) and their antifungal activity. Phytochem Lett 1:44–48 Galeotti F, Barile E, Lanzotti V, Dolci M, Curir P (2008b) Quantification of major flavonoids in carnation tissues (Dianthus caryophyllus) as a tool for cultivar discrimination. Z Naturforsch 63C:161–168 Ganesan K, Xu BJ (2017) Molecular targets of vitexin and isovitexin in cancer therapy: a critical review. Ann N Y Acad Sci 1401:102–113 Ganeshpurkar A, Saluja AK (2017) The pharmacological potential of rutin. Saudi Pharm J 25:149–164 Ganeshpurkar A, Saluja A (2019) The pharmacological potential of hesperidin. Indian J Biochem Biophys 56:287–300 Gevrenova R, Bardarov K, Bouguet-Bonnet S, Voynikov Y, Balabanova V, Zheleva-Dimitrova D, Henry M (2018) A new liquid chromatography-high resolution orbitrap mass spectrometry-based strategy to characterize glucuronide oleanane-type triterpenoid carboxylic acid 3, 28-O-bidesmosides (GOTCAB) saponins. A case study of Gypsophila glomerata Pall ex M. B. (Caryophyllaceae). J Pharm Biomed Anal 159:567–581 Griffiths LA (1959) On the distribution of gentisic acid in green plants. J Exp Bot 10:437–442 Grundmann O, Wang J, McGregor GP, Butterweck V (2008) Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system. Planta Med 74:1769–1773 Gullón B, Lú-Chau TA, Moreira MT, Lema JM, Eibes G (2017) Rutin: A review on extraction, identification and purification methods, biological activities and approaches to enhance its bioavailability. Trends Food Sci Technol 67:220–235 Hegnauer R (1964) Chemotaxonomy of plants, vol 18. Springer Basel AG, Basel, p 379 Hegnauer R (1989) Caryophyllaceae. Chemotaxonomy of Plants, vol 30. Springer Basel AG, Basel, pp 215–220 Heim KE, Tagliaferro AR, Bobilya DJ (2002) Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 13:572–584 Heinsbroek R, van Brederode J, van Nigtevecht G, Maas J, Kamsteeg J, Besson E, Chopin J (1980) The 2″-O-glucosylation of vitexin and isovitexin in petals of Silene alba is catalysed by two different enzymes. Phytochemistry 19:1935–1937 Hollman PCH (2004) Absorption, bioavailability, and metabolism of flavonoids. Pharm Biol 42:74–83 Hostetler GL, Ralston RA, Schwartz SJ (2017) Flavones: food sources, bioavailability, metabolism, and bioactivity. Adv Nutr 28:423–435 Hsieh PW, Chang FR, Lee KH, Hwang TL, Chang SM, Wu YC (2004a) A new anti-HIV alkaloid, drymaritin, and a new C-glycoside flavonoid, diandraflavone, from Drymaria diandra. J Nat Prod 67:1175–1177 Hsieh PW, Chang FR, Wu CC, Wu KY, Li CM, Wang WY, Wu YC (2004b) Selective inhibition of collagen-induced platelet aggregation by a cyclic peptide from Drymaria diandra. Helv Chim Acta 87:57–66 Huang QF, Zhang SJ, Zheng L, Liao M, He M, Huang RB, Lin X (2012) Protective effect of isoorientin-2’-O-α-L-arabinopyranosyl isolated from Gypsophila elegans on alcohol induced hepatic fibrosis in rats. Food Chem Toxicol 50:1992–2001 Hussein IA, Srivedavyasasri R, El-Hela AA, Mohammad AI, Ross SA (2019) Antimicrobial secondary metabolites from Silene rubella growing in Egypt. J Biomed Pharm Res 8:81–84 Hussein IA, Srivedavyasasri R, El-Hela AA, Mohammad AI, Ross SA (2020) Chemical constituents from Silene schimperiana Boiss. belonging to Caryophyllaceae and their chemotaxonomic significance. Biochem Syst Ecol 92:1–4 Iacopini P, Baldi M, Storchi P, Sebastiani L (2008) Catechin, epicatechin, quercetin, rutin and resveratrol in red grape: content, in vitro antioxidant activity and interactions. J Food Compos Anal 21:589–598 Imran M, Rauf A, Shah ZA, Saeed F, Imran A, Arshad MU, Mubarak MS (2018) Chemo-preventive and therapeutic effect of the dietary flavonoid kaempferol: a comprehensive review. Phytother Res 2018:1–13 Imran M, Rauf A, Abu-Izneid T, Nadeem M, Shariati MA, Khan IA, Mubarak MS (2019a) Luteolin, a flavonoid, as an anticancer agent: a review. Biomed Pharmacother 112:108612 Imran M, Salehi B, Sharifi-rad J, Gondal TA, Saeed F, Imran A, Estevinho LM (2019b) Kaempferol: A key emphasis to its anicancer potential. Molecules 24:1–16 Imran M, Aslam GT, Atif M, Shahbaz M, Batool QT, Hanif MM, Sharifi-Rad J (2020) Apigenin as an anticancer agent. Phytother Res 26:1–17 Itokawa H, Yun Y, Morita H, Takeya K, Yamada K (1995) Estrogen-like activity of cyclic peptides from Vaccaria segetalis extracts. Planta Med 61:561–562 Iwashina T, Yamaguchi MA, Nakayama M, Onozaki T, Yoshida H, Kawanobu S, Okamura M (2010) Kaempferol glycosides in the flowers of carnation and their contribution to the creamy white flower color. Nat Prod Commun 5:1903–1906 Jakimiuk K, Strawa JW, Granica S, Tomczyk M (2020) Flavonoids from the aerial parts of Scleranthus perennis. T20 PSE Conference Liverpool 2020, "Contemporary Natural Products Discovery Research", 6.03.2020, Liverpool, United Kingdom, p. 57 Jia AQ, Tan NH, Yang YP, Wu SG, Wang LQ, Zhou J (2004) Cyclopeptides from three arctic Caryophyllaceae plants, chemotaxonomy and distribution significance of Caryophyllaceae cyclopeptides. Acta Bot Sin 46:625–630 Jovanović O, Radulović N, Palić R, Zlatković B (2009) Volatiles of Minuartia recurva (All.) Schinz et Thell. subsp. recurva (Caryophyllaceae) from Serbia. J Essent Oil Res 21:429–432 Jung HJG, Batzli GO, Seigler DS (1979) Patterns in the phytochemistry of arctic plants. Biochem Syst Ecol 7:203–209 Jürgens A (2004) Flower scent composition in diurnal Silene species (Caryophyllaceae): phylogenetic constraints or adaption to flower visitors? Biochem Syst Ecol 32:841–859 Jürgens A, Witt T, Gottsberger G (2002) Flower scent composition in night-flowering Silene species (Caryophyllaceae). Biochem Syst Ecol 30:383–397 Jürgens A, Witt T, Gottsberger G (2003) Flower scent composition in Dianthus and Saponaria species (Caryophyllaceae) and its relevance for pollination biology and taxonomy. Biochem Syst Ecol 31:345–357 Kamsreeo J, van Brederode J, van Nigtevecht G (1980) Genetical and biochemical evidence that the hydroxylation pattern of the anthocyanin B-ring Silene dioica is determined at the p-coumaroyl-coenzyme a stage. Phytochemistry 19:1459–1462 Kamsteeg J, van Brederode J, van Nigtevecht G (1976) Pleiotropic effect of a pelargonidin-hydroxylation gene in Silene dioica. Phytochemistry 15:1917–1918 Ke JY, Cole RM, Hamad EM, Hsiao YH, Cotten BM, Powell KA, Belury MA (2016) Citrus flavonoid, naringenin, increases locomotor activity and reduces diacylglycerol accumulation in skeletal muscle of obese ovariectomized mice. Mol Nutr Food Res 60:313–324 Kew Science (2020) The Royal Botanic Gardens, Great Britain. http://plantsoftheworldonline.org Accesed 27 Nov 2020 Kılınç H, Masullo M, Bottone A, Karayıldırım T, Alankuş Ö, Piacente S (2019) Chemical constituents of Silene montbretiana. Nat Prod Res 33:335–339 Kim DW, Hwang IK, Lim SS, Yoo KY, Li H, Kim YS, Kwon DY, Moon WK, Kim DW, Won MH (2009) Germinated Buckwheat extract decreases blood pressure and nitrotyrosine immunoreactivity in aortic endothelial cells in spon-taneously hypertensive rats. Phytother Res 23:993–998 Kim YB, Reed DW, Covello PS (2015) Production of triterpenoid sapogenins in hairy root cultures of Silene vulgaris. Nat Prod Commun 10:1919–1922 Kirillov V, Stikhareva T, Suleimen Y, Serafimovich M, Kabanova S, Mukanov B (2017) Chemical composition of the essential oil from carnation coniferous (Dianthus acicularis Fisch. ex Ledeb) growing wild in Northern Kazakhstan. Nat Prod Res 31:117–123 Kitanov GM (1992) Phenolic acids and flavonoids from Stellaria media (L.) Vill. (Caryophyllaceae). Pharmazie 47:470–471 Koike K, Jia Z, Nikaido T (1998) Triterpenoid saponins from Vaccaria segetalis. Phytochemistry 47:1343–1349 Koike K, Jia Z, Nikaido T (1999) New triterpenoid saponins and sapogenins from Saponaria officinalis. J Nat Prod 62:1655–1659 Kozachok S, Pecio Ł, Kolodziejczyk-Czepas J, Marchyshyn S, Nowak P, Mołdoch J, Oleszek W (2018) γ-Pyrone compounds: flavonoids and maltol glucoside derivatives from Herniaria glabra L. collected in the Ternopil region of the Ukraine. Phytochemistry 152:213–222 Kozlowska J, Potaniec B, Zarowska B, Aniol M (2017) Synthesis and biological activity of novel o-alkyl derivatives of naringenin and their oximes. Molecules 22:1–14 Krasteva IN, Popov IS, Balabanova VI, Nikolov SD, Pencheva IP (2008) Phytochemical study of Gypsophila trichotoma Wend. (Caryophyllaceae). Quim Nova 31:1125–1126 Kremer D, Košir IJ, Potočnik T, Rogulj N, Načinović K, Randić M, Srečec S, JurišićGrubešić R (2021) Phenolic compounds in two subspecies of Drypis spinosa L. (Caryophyllaceae) growing in Croatia. Acta Bot Croatica. https://doi.org/10.37427/botcro-2020-015 Krížová L, Dadáková K, Kašparovská J, Kašparovský T (2019) Isoflavones. Molecules 24:1–28 Królikowska M, Szymańska M, Wolbiś M (1983) Rhamnazin 3-rutinoside from Herniaria ciliolata Meld. spp. robusta Chaudhri. Acta Pol Pharm 40:643–648 Kubitzki K (1993) In: Kubitzki K, Rohwer JG, Bittrich V (eds) Flowering plants dicotyledons. Springer, Berlin Kukongviriyapan U, Sompamit K, Pannangpetch P, Kukongviriyapan V, Donpunha W (2012) Preventive and therapeutic effects of quercetin on lipopolysaccharide-induced oxidative stress and vascular dysfunction in mice. Can J Physiol Pharmacol 90:1345–1353 Kulevanova S, Stefova M, Kadifkova Panovska T, Stafilov T (2003) HPLC identification and determination of myricetin, quercetin, kaempferol and total flavonoids in herbal drugs. Maced Pharm Bull 48:25–30 Kumar P, Khanna P (1994) Flavonoids from Saponaria vaccaria Linn. Indian J Plant Physiol 37:76–78 Kumar RK, Herbert C, Foster PS (2008) The “classicall” ovalbumin challenge model of asthma in mice. Curr Cancer Drug Targets 9:485–494 Kuwayama S, Nakata M, Godo T, Nakano M (2005) Analyses of anthocyanidins and anthocyanins in flower petals of Lychnis senno and its related species (Caryophyllaceae). Bull Fac Agric Niigata Univ 58:35–38 Lam KY, Ling APK, Koh RY, Wong YP, Say YH (2016) A review on medicinal properties of orientin. Adv Pharmacol Sci 2016:4104595 Larhsini M, Marston A, Hostettmann K (2003) Triterpenoid saponins from the roots of Silene cucubalus. Fitoterapia 74:237–241 Liang X, Li Y, Fan H, Huang W, Zhang H, Cui Y, Song X (2019) Chemical constituents from the roots and rhizomes of Silene tatarinowii Regel. Biochem Syst Ecol 86:103932 Lin X, Chen Y, Lv S, Tan S, Zhang S, Huang R, Huang Q (2015) Gypsophila elegans isoorientin attenuates CCl4-induced hepatic fibrosis in rats via modulation of NF-κB and TGF-β1/Smad signaling pathways. Int Immunopharmacol 28:305–312 Lin X, Wei J, Chen Y, He P, Lin J, Tan S, Huang Q (2016) Isoorientin from Gypsophila elegans induces apoptosis in liver cancer cells via mitochondrial-mediated pathway. J Ethnopharmacol 187:187–194 Litvinenko VI, Amanmuradov K, Abubakirov NK (1967) Glycosides of Vaccaria segetalis IV Isosaponarin. Chem Nat Compd 3:131–134 Liu XX, Wang L, Wang Q, Qiu B (2007) Chemical constituents from root of Psammosilene tunicoides. China J Chin Mater Med 32:921–923 Liu Z, Lindemeyer AK, Liang J, Wallner M, Shao XM, Shao Y, Olsen RW (2018) Flavonoids isolated from Tibetan medicines, binding to GABAA receptor and the anticonvulsant activity. Phytomedicine 50:1–7 Liu Y, Song FM, Ma ST, Moro A, Feng WY, Liao SJ, Liu Q (2019) Vaccarin prevents titanium particle-induced osteolysis and inhibits RANKL-induced osteoclastogenesis by blocking NF-κB and MAPK signaling pathways. J Cell Physiol 234:13832–13842 Luo JG, Cao LH, Kong LY (2012) Two new β-carboline-type alkaloids from Stellaria dichotoma var. lanceolata. Chin Chem Lett 23:1385–1388 Ma X, Wu C, Wang W, Li X (2006) Peptides form plants: a new source for antitumor drug research. Asian J Tradit Med 1:85–90 Ma L, Gu YC, Luo JG, Wang JS, Huang XF, Kong LY (2009) Triterpenoid saponins from Dianthus versicolor. J Nat Prod 72:640–644 Ma LY, Liu RH, Xu XD, Yu MQ, Zhang Q, Liu HL (2010) The pharmacokinetics of C-glycosyl flavones of Hawthorn leaf flavonoids in rat after single dose oral administration. Phytomedicine 17:640–645 Maleš Ž, Crkvenčić M, Pilepić KH, Herenda F (2013) Investigation of flavonoids, phenolic acids and amino acids of smooth rupturewort—Herniaria glabra L. Farm Glas 69:673–684 Maliński MP, Michalska AD, Tomczykowa M, Tomczyk M, Thiem B (2014) Ragged Robin (Lychnis flos-cuculi)—a plant with potential medicinal value. Rev Bras 24:722–730 Maliński MP, Kikowska M, Kruszka D, Napierała M, Florek E, Śliwińska E, Thiem B (2019) Various in vitro systems of Ragged Robin (Lychnis fos-cuculi L.): a new potential source of phytoecdysteroids? Plant Cell Tissue Organ Cult 139:39–52 Mamadalieva NZ, Zibareva LN, Lafont R, Dainan L, Saatov Z (2004) Phytoecdysteroids from the Silene genus. Chem Nat Compd 40:574–578 Mamadalieva NZ, Egamberdieva D, Lafont R, Girault JP (2008) Phytoecdysteroids and antibacterial activity of the plant Coronaria flos-cuculi. Chem Nat Compd 44:404–406 Mamadalieva NZ, El-Readi MZ, Janibekov AA, Tahrani A, Wink M (2011) Phytoecdysteroids of Silene guntensis and their in vitro cytotoxic and antioxidant activity. Z Naturforsch 66C:215–224 Mamadalieva NZ, Lafont R, Wink M (2014) Diversity of secondary metabolites in the genus Silene L. (Caryophyllaceae)—structures, distribution, and biological properties. Diversity 6:415–499 Mandal P, Misra TK, Ghosal M (2009) Free-radical scavenging activity and phytochemical analysis in the leaf and stem of Drymaria diandra Blume. Int J Integr Biol 7:80–84 Martineti V, Tognarini I, Azzari C, Sala SC, Clematis F, Dolci M, Curir P (2010) Inhibition of in vitro growth and arrest in the G0/G1 phase of HCT8 line human colon cancer cells by kaempferide triglycoside from Dianthus caryophyllus. Phytother Res 24:1302–1308 Mbark AN, Charrouf Z, Guillaume D, Kol O (1999) New glycosides from Herniaria fontanesii. Stud Plant Sci 6:314–319 Melnyk MV, Vodoslavskyi VM, Obodianskyi MA (2018) Research of phenolic compounds of Ruta graveolens L. and Stellaria media (L.) Vill. Asian J Pharm Clin Res 11:152–156 Meng Y, Whiting P, Zibareva L, Bertho G, Girault JP, Lafont R, Dinan L (2001) Identification and quantitative analysis of the phytoecdysteroids in Silene species (Caryophyllaceae) by high-performance liquid chromatography: Novel ecdysteroids from S. pseudotites. J Chromatogr A 935:309–319 Meselhy MR, Aboutabl ES (1997) Hopane-type saponins from Polycarpon succulentum growing in Egypt. Phytochemistry 44:925–929 Mihaylova D, Vrancheva R, Desseva I, Ivanov I, Dincheva I, Popova M, Popova A (2018) Analysis of the GC-MS of volatile compounds and the phytochemical profile and antioxidant activities of some Bulgarian medicinal plants. Z Naturforschung 74C:45–54 Mikšátková P, Ancheeva E, Hejtmánková K, Teslov L, Lapčík O (2014) Determination of flavonoids in Stellaria by high-performance liquid chromatography-tandem mass spectrometry. Anal Lett 47:2317–2331 Morales P, Carvalho AM, Sánchez-Mata MC, Cámara M, Molina M, Ferreira ICFR (2012) Tocopherol composition and antioxidant activity of Spanish wild vegetables. Genet Resour Crop Evol 59:851–863 Mubarek MM (2019) Pharmacognostical studies on Gymnocarpos decandrus Forrssk. growing at North Western Coast in Egypt, Doctoral dissertation, Cairo University Nakano T, Sugimoto S, Matsunami K, Otsuka H (2011) Dianthosaponins A-F, triterpene saponins, flavonoid glycoside, aromatic amide glucoside and γ-pyrone glucoside from Dianthus japonicus. Chem Pharm Bull 59:1141–1148 Nakayama M, Koshioka M, Yoshida H, Kan Y, Fukui Y, Koike A, Yamaguchi MA (2000) Cyclic malyl anthocyanins in Dianthus caryophyllus. Phytochemistry 55:937–939 Nerio LS, Olivero-Verbel J, Stashenko E (2010) Repellent activity of essential oils: A review. Biores Technol 101:372–378 Niemann GJ (1984) Leaf flavonoid glycosylation and sprout morphogenesis in Silene pratensis influenced by the spectral composition of light. J Plant Physiol 115:311–318 Niemann GJ (1993) The anthranilamide phytoalexins of the Caryophyllaceae and related compounds. Phytochemistry 34:319–328 Nono RN, Nguelefack-Mbuyo EP, Nzowa LK, Ponou BK, Teponno RB, Nguelefack TB, Park HJ (2016) Antioxidant C-glycosylflavones of Drymaria cordata (Linn.) Willd. Arch Pharmacal Res 39:43–50 Obmann A, Zehl M, Purevsuren S, Narantuya S, Reznicek G, Kletter C, Glasl S (2011b) Quantification of flavonoid glycosides in an aqueous extract from the traditional Mongolian medicinal plant Dianthus versicolor Fisch. J Sep Sci 34:292–298 Obmann A, Werner I, Presser A, Zehl M, Swoboda Z, Purevsuren S, Glasl S (2011a) Flavonoid C- and O-glycosides from the Mongolian medicinal plant Dianthus versicolor Fisch. Carbohyd Res 346:1868–1875 Obmann A, Purevsuren S, Zehl M, Kletter C, Reznicek G, Narantuya S, Glasl S (2012) HPLC determination of flavonoid glycosides in Mongolian Dianthus versicolor Fisch. (Caryophyllaceae) compared with quantification by UV spectrophotometry. Phytochem Anal 23:254–259 Ogata J, Itoh Y, Ishida M, Yoshida H, Ozeki Y (2004) Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus. Plant Biotechnol 21:367–375 Olennikov DN (2020) Silenerepin—a new C-glycosylflavone from Silene repens. Chem Nat Compd 56:423–426 Pacifico S, Scognamiglio M, D’Abrosca B, Piccolella S, Tsafantakis N, Gallicchio M, Fiorentino A (2010) Spectroscopic characterization and antiproliferative activity on HepG2 human hepatoblastoma cells of flavonoid C-glycosides from Petrorhagia velutina. J Nat Prod 73:1973–1978 Panche AN, Diwan AD, Chandra SR (2016) Flavonoids: an overview. J Nutr Sci 5:1–15 Pei R, Liu X, Bolling B (2020) Flavonoids and gut health. Curr Opin Biotechnol 61:153–159 Peng Y, Gan R, Li H, Yang M, Mcclements DJ (2020) Absorption, metabolism, and bioactivity of vitexin: recent advances in understanding the efficacy of an important nutraceutical. Critical Reviews in Food Science and Nutrition 1–16 Plant Database (2020) United States Department of Agriculture, United States of America. https://plants.sc.egov.usda.gov. Accesed 27 Nov 2020 Powers JM, Seco R, Faiola CL, Sakai AK, Weller SG, Campbell DR, Guenther A (2020) Floral scent composition and fine-scale timing in two moth-pollinated Hawaiian Schiedea (Caryophyllaceae). Front Plant Sci 11:1–16 Praveena R, Sadasivam K, Deepha V, Sivakumar R (2014) Antioxidant potential of orientin: a combined experimental and DFT approach. J Mol Struct 1061:114–123 Qi P, Li Z, Chen M, Sun Z, Huang C (2013) Metabolism and tissue distribution study of Vaccaria seeds (Wang-Bu-Liu-Xing) in benign prostatic hyperplasia model rat: toward an in-depth study for its bioactive components. J Pharm Biomed Anal 85:218–230 Qi P, Zhang F, Xue R, Li Z, Chen M, Sun Z, Huang C (2014) Identification of multiple constituents from seed of Vaccaria segetalis with an adsorbent-separation strategy based on liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 28:1243–1257 Radulović NS, Ristić MN, Ristić NR, Dekić VS, Dekić BR, Mladenović MZ (2018) The floral scent of Dianthus cruentus Griseb (Caryophyllaceae). Fac Univ Ser Phys Chem Technol 16:161 Richardson M (1978) Flavonols and C-glycosylflavonoids of the caryophyllales. Biochem Syst Ecol 6:283–286 Rizk AM (1986) Phytochemistry of the flora of Qatar. Scientific and Applied Research Centre, University of Qatar, Qatar Rogowska M, Lenart M, Srecec S, Ziaja M, Parzonko A, Bazylko A (2017) Chemical composition, antioxidative and enzyme inhibition activities of chickweed herb (Stelaria media L., Vill.) ethanolic and aqueous extracts. Ind Crops Prod 97:448–454 Sachdeva AK, Kuhad A, Chopra K (2014) Naringin ameliorates memory deficits in experimental paradigm of Alzheimer’s disease by attenuating mitochondrial dysfunction. Pharmacol Biochem Behav 127:101–110 Said RB, Hamed AI, Masullo M, Al-Ayed AS, Moustafa MFM, Mahalel UA, Piacente S (2019) Flavone C-glycosides from Vaccaria pyramidata: structure elucidation by spectroscopy and theoretical calculations. Phytochem Lett 29:119–124 Sait S, Hamri-Zeghichi S, Boulekbache-Makhlouf L, Madani K, Rigou P, Brighenti V, Pellati F (2015) HPLC-UV/DAD and ESI-MSn analysis of flavonoids and antioxidant activity of an Algerian medicinal plant: Paronychia argentea Lam. J Pharm Biomed Anal 111:231–240 Salehi B, Fokou PVT, Sharifi-Rad M, Zucca P, Pezzani R, Martins N, Sharifi-Rad J (2019) The therapeutic potential of naringenin: A review of clinical trials. Pharmaceuticals 12:1–18 Salt TA, Adler JH (1986) Dominance of Δ7-sterols in the family Caryophyllaceae. Lipids 21:754–758 Sang SM, Xia ZH, Mao SL, Lao A, Chen ZL (2000) Studies on the flavonol glycosides from the seeds of Vaccaria segetalis. China J Chin Mater Med 25:221–222 Sang S, Xia Z, Lao A, Cao L, Chen Z, Uzawa J, Fujimoto Y (2003b) Studies on the constituents of the seeds of Vaccaria segetalis. Heterocycles 59:811–821 Sang S, Lao A, Chen Z, Uzawa J, Fujimoto Y (2003) In: Ho CT (ed.) Oriental foods and herbs. Oxford University Press, Washington Schmidt J, Bohme F, Adam G (1996) 24-Epibrassinolide from Gypsophila perfoliata. Z Naturforsch 51C:897–899 Schweingruber FH (2007) Stem anatomy of Caryophyllaceae. Flora - Morphology, Distribution, Functional Ecology of Plants 202:281–292 Seo C, Shin HS, Lee JE, Jung YW, Kim JK, Kwon JG, Hong SS (2020) Isolation and structure elucidation of siliendines A-D, new β-carboline alkaloids from Silene seoulensis. Phytochem Lett 36:58–62 Seraya L, Birke K, Khimenko SV, Boguslavskaya L (1978) Flavonoid compounds of Dianthus superbus. Khim Prir Soedin 6:802–803 Serra A, Macià A, Romero MP, Reguant J, Ortega N, Motilva MJ (2012) Metabolic pathways of the colonic metabolism of flavonoids (flavonols, flavones and flavanones) and phenolic acids. Food Chem 130:383–393 Shafaghat A, Shafaghatlonbar M (2011) Antimicrobial activity and chemical constituents of the essential oils from flower, leaf and stem of Gypsophila bicolor from Iran. Nat Prod Commun 6:275–276 Sharma A, Arora D (2012) Phytochemical and pharmacological potential of genus Stellaria: A review. J Pharm Res 5:3591–3596 Shinjiro O, Junko M, Godo T, Kato Y (2009) Possibility for selective accumulation of polyphenolics in tissue cultures of Senno (Lychnis senno Siebold et Zucc.). Nat Prod Commun 4:377–380 Shukla S, Gupta S (2010) Apigenin: a promising molecule for cancer prevention. Pharm Res 27:962–978 Simeonova R, Kondeva-Burdina M, Vitcheva V, Krasteva I, Manov V, Mitcheva M (2014) Protective effects of the apigenin-O/C-diglucoside saponarin from Gypsophila trichotoma on carbone tetrachloride-induced hepatotoxicity in vitro/in vivo in rats. Phytomedicine 21:148–154 Singh M, Kaur M, Silakari O (2014) Flavones: an important scaffold for medicinal chemistry. Eur J Med Chem 84:206–239 Slavokhotova AA, Odintsova TI, Rogozhin EA, Musolyamov AK, Andreev YA, Grishin EV, Egorov TA (2011) Isolation, molecular cloning and antimicrobial activity of novel defensins from common chickweed (Stellaria media L.) seeds. Biochimie 93:450–456 Smolyakova IM, Avdeenko SN, Kalinkina GI, Yusubov MS, Zibareva LN (2010) Analysis of the chemical composition of Lychnis chalcedonica cultivated in Western Siberia. Chem Plant Mater 2010:95–102 Stich K, Eidenberger T, Wurst F, Forkmann G (1992) Enzymatic conversion of dihydroflavonols to flavan-3,4-diols using flower extracts of Dianthus caryophyllus L. (carnation). Planta 187:103–108 Sun J, Yu JH, Song JL, Jiang CS, Yuan T, Zhang H (2019) Two new quinolone alkaloids from Dianthus superbus var. superbus. Tetrahedron Lett 60:161–163 Taskin T, Bitis L (2013) Antioxidant activity of Silene alba subsp. divaricata and Stellaria media subsp. media from Caryophyllaceae. Spatula DD 3:1–5 Thiem B, Kikowska M, Maliński MP, Kruszka D, Napierała M, Florek E (2016) Ecdysteroids: production in plant in vitro cultures. Phytochem Rev 16:603–622 Thilakarathna SH, Rupasinghe HPV (2013) Flavonoid bioavailability and attempts for bioavailability enhancement. Nutrients 5:3367–3387 Tlili H, Hanen N, Arfa AB, Neffati M, Boubakri A, Buonocore D, Doria E (2019) Biochemical profile and in vitro biological activities of extracts from seven folk medicinal plants growing wild in southern Tunisia. PLoS ONE 14:1–18 Tomczyk M (2008) Preliminary phytochemical investigation of Lychnis flos-cuculi herbs. J Nat Med 62:473–475 Tong Y, Luo JG, Wang R, Wang XB, Kong LY (2012) New cyclic peptides with osteoblastic proliferative activity from Dianthus superbus. Bioorg Med Chem Lett 22:1908–1911 Tong H, Sun BG, ChangTao W, Sun XT, Xue Z (2014) Study on surfactant-assisted extraction process and preliminary structural analysis of total flavonoids from Arenaria kansuensis Maxim. Food Res Dev 35:14–18 Tu Y, Zhu S, Wang J, Burstein E, Jia D (2019) Natural compounds in the chemoprevention of alcoholic liver disease. Phytother Res 33:2192–2212 Ullah F, Ayaz A, Saqib S, Zaman W, Butt MA, Ullah A (2019) Silene conoidea L.: A review on its systematic, ethnobotany and phytochemical profile. Plant Sci Today 6:373–382 Uma Devi P, Ganasoundari A, Vrinda B, Srinivasan KK, Unnikrishnan MK (2000) Radiation protection by the Ocimum flavonoids orientin and vicenin: mechanisms of action. Radiat Res 154:455–460 Van Wyk BE, Wink M (2017) Medicinal plants of the World. Briza Publications, Pretoria Van Brederode J, van Genderen HH, Berendsen W (1982) Morphological effects of the flavone isovitexin in a non-glycosylating genotype of Silene pratensis (Caryophyllaceae). Experientia 38:929–931 Van Dooren I, Foubert K, Bijttebier S, Theunis M, Velichkova S, Claeys M, Apers S (2016) Saponins and flavonoids from an infusion of Herniaria hirsuta. Planta Med 82:1576–1583 Vardavas CI, Majchrzak D, Wagner KH, Elmadfa I, Kafatos A (2006) The antioxidant and phylloquinone content of wildly grown greens in Crete. Food Chem 99:813–821 Vincken JP, Heng L, de Groot A, Gruppen H (2007) Saponins, classification and occurrence in the plant kingdom. Phytochemistry 68:275–297 Vinholes J, Grosso C, Andrade PB, Gil-Izquierdo A, Valentão P, Pinho PGD, Ferreres F (2011) In vitro studies to assess the antidiabetic, anti-cholinesterase and antioxidant potential of Spergularia rubra. Food Chem 129:454–462 Viskupičová J, Ondrejovič M, Šturdík E (2008) Bioavailability and metabolism of flavonoids. J Food Nutr Res 47:151–162 Vitale DC, Piazza C, Melilli B, Drago F, Salomone S (2013) Isoflavones: estrogenic activity, biological effect and bioavailability. Eur J Drug Metab Pharmacokinet 38:15–25 Vitcheva V, Simeonova R, Krasteva I, Yotova M, Nikolov S, Mitcheva M (2011) Hepatoprotective effects of saponarin, isolated from Gypsophila trichotoma Wend. on cocaine-induced oxidative stress in rats. Redox Rep 16:56–61 Volodin VV, Volodina SO (2015) Floristic and molecular phylogenetic analysis of the distribution of phytoecdysteroids among plants of North-East Russia (Asteraceae and Caryophyllaceae). Biol Med 7:1 Wang X, Dong H, Liu Y, Yang B, Wang X, Huang L (2011) Application of high-speed counter-current chromatography for preparative separation of cyclic peptides from Vaccaria segetalis. J Chromatogr B 879:811–814 Wang G, Luo JG, Yang MH, Wang XB, Kong LY (2013) Six new cyclic peptides from the roots of Gypsophila oldhamiana. Chem Pharm Bull 61:489–495 Wang W, Sun C, Mao L, Ma P, Liu F, Yang J, Gao Y (2016) The biological activities, chemical stability, metabolism and delivery systems of quercetin: a review. Trends Food Sci Technol 56:21–38 Wink M (2011) Biochemistry of Plant Secondary Metabolism, 2nd edn. Wiley-Blackwell, Chichester Wink M (2015) Modes of action of herbal medicines and plant secondary metabolites. Medicines 2:251–286 Wolf SJ, Denford KE, Packer JG (1979) A study of the flavonoids of the Minuartia rossii complex. Can J Bot 57:2374–2377 Wu FE, Koike K, Nikaido T, Sakamoto Y, Ohmoto T, Ikeda K (1989) New β-Carboline alkaloids from a Chinese medicinal plant, Arenaria kansuensis. Structures of arenarines A, B, C, D. Chem Pharm Bull 37:1808–1809 Wu FE, Koike K, Nikaido T, Ishii K, Ohmoto T, Ikeda K (1990) Terpenoids and flavonoids from Arenaria kansuensis. Chem Pharm Bull 38:2281–2282 Yasukawa K, Yamanouchi S, Takido M (1981) Studies on the constituents in the water extracts of crude drugs. III. On the roots of Stellaria dichotoma L. var. lanceolata BGE. Yakugaku Zasshi 101:64–66 Yayli N, Seymen H, Baltaci C (2001) Flavone C-glycosides from Scleranthus uncinatus. Phytochemistry 58:607–610 Yayli N, Baltaci C, Genç H, Terzioǧlu S (2002) Phenolic and flavone C-glycosides from Scleranthus uncinatus. Pharm Biol 40:369–373 Yoshida H, Itoh Y, Ozeki Y, Iwashina T, Yamaguchi MA (2004) Variation in chalcononaringenin 2′-O-glucoside content in the petals of carnations (Dianthus caryophyllus) bearing yellow flowers. Sci Hortic 99:175–186 Yücel TB, Yayli N (2018) GC/MS analysis and antimicrobial activity of the volatile compounds from Dianthus carmelitarum Reut. ex Boiss and Dianthus calocephalus Boiss. grown in Turkey. J Agric Fac Ege Univ 55:89–94 Zanotti SD, de Abreu Ribeiro GK, Zeppone LC, Borges CT (2013) Orange juice and hesperidin promote differential innate immune response in macrophages ex vivo. Int J Vitam Nutr Res 83:162–167 Zaychenko SG, Zernov AS (2017) Structural features of the seed coat in Caucasian representatives of Minuartia (Caryophyllaceae ). Wulfenia J 24:205–220 Zdraveva P, Gevrenova R, Dimitrova B (2004) Phenolic compounds of Scleranthus annuus L. (Caryophyllaceae). 3rd Conference on Medicinal and Aromatic Plants of Southeast European Countries. Nitra, Slovakia Republic 2004:57 Zdraveva P, Pencheva I, Popova P, Ionkova I, Krasteva I (2015) Production of saponarin in in vitro cultures of Gypsophila species. J Chem Pharm Res 7:829–832 Zemtsova GN, Glyzin VY, Dzhumyrko SF (1976) Flavones and their C-glycosides from Silene saxatilis. Chem Nat Compd 11:538 Zhang H (2012) Profiling analysis of the seeds of Vaccaria segetalis (Necr.) Gracke by HPLC-ESI-MS. Adv Mater Res 396–398:96–98 Zhang FM, Tai ZG, Cai L, Yang YB, Li F, Ding ZT (2011) Flavonoids from Gypsophila elegans and their antioxidant activities. J Yunnan Univ (Nat Sci Ed) 33:93–95 Zhang H, Wang K, Wu J, Chen Y, He P (2011) A new flavonoid glycoside from Vaccaria hispanica. Nat Prod Commun 6:1599–1602 Zhang Y, Wang G, Lv H, Luo J, Kong L (2015) Two new β-carboline alkaloids from the roots of Gypsophila oldhamiana. Nat Prod Res 29:1207–1211 Zheleva-Dimitrova D, Zengin G, Balabanova V, Voynikov Y, Lozanov V, Lazarova I, Gevrenova R (2018) Chemical characterization with in vitro biological activities of Gypsophila species. J Pharm Biomed Anal 155:56–69 Zhou X, Wang L, Tian Y, Gong X, Zhao C, Yang S (2013) Chemical constituents from roots of Psammosilene tunicoides. Zhongguo Zhong Yao Za Zhi 38:3507–3509 Zhou G, Tang L, Wang T, Zhou X, Kou Z, Wu J, Wang Z (2016) Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review. Phytochem Rev 15:813–827 Zhou G, Wu H, Wang T, Guo R, Xu J, Zhang Q, Wang Z (2017) C-glycosylflavone with rotational isomers from Vaccaria hispanica (Miller) Rauschert seeds. Phytochem Lett 19:241–247 Zhu G, Liu X, Li H, Yan Y, Hong X, Lin Z (2018) Kaempferol inhibits proliferation, migration, and invasion of liver cancer HepG2 cells by down-regulation of microRNA-21. Int J Immunopathol Pharmacol 32:1–12 Zhuang L (1983) C-Glycosylflavones from Qi Gu Cao (Sagina japonica). Zhongcaoyao 14:295–297 Zitouni M (2017) Profil polyphénolique et activité antioxydante de deux plantes médicinales Pistacia lentiscus. L et Gymnocarpos decander Forsk. Universite Abou Bekr Belkaid, Tlemcen Zoll A, Nouvel G (1974) Comparative study of C-glycosyl flavones of two Caryophyllaceae. Spergularia rubra and Stellaria holostea. Phytochemistry 8:134–140