Skip to main content
SpringerLink
Log in

Antioxidant C-glycosylflavones of Drymaria cordata (Linn.) Willd

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

A new C-glycosylflavone, drymaritin E (6-C-(3-keto-β-digitoxopyranosyl)-4′-O-(β-d-glucopyranosyl)-7-methoxyl-5,4′-dihydroxylflavone) 1 was isolated from the oily upper phase (SU) of the MeOH extract from aerial parts of Drymaria cordata together with two known compounds (cassiaoccidentalin A 2 and anemonin 3) and an inseparable mixture of two known C-glycosylflavones 5,4′-dihydroxy-7-methoxyflavone-6-C-(2′′-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside 4a and 5,7,3′,4′-tetrahydroxyflavone-6-C-(2′′-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside 4b. The alkaline hydrolysis of 3 led to a new hemisynthetic derivative, sodium anemonate (sodium 2-((1’E) 2′-sodium-carboxylate-vinyl)-5-oxo-cyclohex-1-ene carboxylate) 3a. The chemical structures were determined by spectroscopic methods (1H NMR, 13C NMR, 1H-1H COSY, HMBC, HSQC, and NOESY) and mass spectrometry (ESI–MS). C-glycosylflavones had significant free radical-scavenging activities on the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, SU and compounds 3 and 3a exhibited no activity. In particular, compound 1 exhibited a concentration-dependent radical scavenging activity on DPPH with EC50 of 31.43 µg/mL.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Adeyemi OO, Akindele AJ, Ndubuisi N (2008) Anti-inflammatory Activity of Drymaria cordata extract. J Nat Rem 8:93–100

    Google Scholar 

  • Agrawal PK (1989) Carbon-13 NMR of flavonoids. Elsevier, New York

    Google Scholar 

  • Agrawal PK (1992) NMR spectroscopy in the structure elucidation of oligosaccharides and glycosides. Phytochemistry 31:3307–3330

    Article  PubMed  CAS  Google Scholar 

  • Akindele AJ, Ibe IF, Adeyemi OO (2012) Analgesic and antipyretic activities of Drymaria cordata (Linn.)Willd (Caryophyllaceae) extract. Afr J Trad Compl Alt Med 9:25–35

    CAS  Google Scholar 

  • Barua CC, Roy JD, Buragohain B, Barua AG, Borah P, Lahkar M (2009) Anxiolytic activity of hydroethanolic extract of Drymaria cordata Willd. Ind J Exper Biol 47:969–973

    Google Scholar 

  • Barua CC, Barua AG, Roy JD, Buragohain B, Borah P (2010) Studies on the anti-inflammatory properties of Drymaria cordata leaf extract. Ind J Anim Sci 80:1268–1270

    Google Scholar 

  • Bucar F, Jachak SM, Kartning T, Schubert-Zsilaveez M (1998) Phenolic compounds from Biophlum sensitivum. Pharmazie 53:651–653

    CAS  Google Scholar 

  • Burkill HM (1985) The useful plants of west tropical Africa, vol 1. Royal Botanic Gardens, Kew

    Google Scholar 

  • De Oliveira AMF, Pinheiro LS, Pereira CKS, Matias WN, Gomes RA, Chaves OS, De Souza MDFV, De Almeida RN, De Assis TS (2012) Total phenolic content and antioxidant activity of some Malvaceae family species. Antioxidants 1:33–43

    Article  Google Scholar 

  • Ding Z, Zhou J, Tan N (1999) A novel flavonoid glycoside from Drymaria diandra. Planta Med 65:578–579

    Article  PubMed  CAS  Google Scholar 

  • Ding ZT, Yang XQ, Cao QE, Li F (2005) Three new flavone glycosides from Drymaria diandra Bl. J Integr Plant Biol Former Acta Bot Sin 47:1140–1144

    Article  CAS  Google Scholar 

  • Fouedjou TR, Teponno RB, Quassinti L, Bramussi M, Petreli D, Vitali LA, Fiorini D, Tapondjou AL, Barboni L (2014) Steroidal saponins from leaves of Cordyline fruticosa (L.) A. Chev. and their cytotoxic and antimicrobial activity. Phytochemistry Lett. 7:62–68

    Article  CAS  Google Scholar 

  • Gruenwald J, Brendler T, Jaenicke C (2000) PDR for herbal medicine. Medical Economics Company, Montvale

    Google Scholar 

  • Hatano T, Mizuta S, Ito H, Yoshida T (1999) C-glycosidic flavonoids from Cassia occidentalis. Phytochemistry 52:1379–1383

    Article  CAS  Google Scholar 

  • Hsieh PW, Chang FR, Yen HF, Wu YC (2003) Anemonin and two norsesquiterpenes from Drymaria diandra. Biochem Syst Ecol 31:541–543

    Article  CAS  Google Scholar 

  • Ibrahim M, Nada A, Kamal DE (2005) Density functional theory and FTIR spectroscopic study of carbonyl group. Ind J Pure Appl Phys 43:911–917

    CAS  Google Scholar 

  • Jia A, Yang YF, Kong DY (2012) Isolation and structural identification of C-glycosylflavones from Callicarpa kwangtungensis Chun. and their preliminary anti-inflammatory activities. Chin J Pharm 43:263–267

    CAS  Google Scholar 

  • Mukherjee PK, Saha K, Bhattacharya S, Giri SN, Pal M, Saha BP (1997) Studies on antitussive activity of Drymaria cordata Willd. (Caryophyllaceae). J Ethnopharmacol 56:77–80

    Article  PubMed  CAS  Google Scholar 

  • Mukherjee PK, Bhattacharya S, Saha S, Giri SN, Pal M, Saha BP (1998) Antibacterial evaluation of Drymaria cordata Willd (Fam. Caryophyllaceae) extract. Phytother Res 11:249–250

    Article  Google Scholar 

  • Nguelefack-Mbuyo PE, Dimo T, Nguelefack TB, Azebaze AGB, Dongmo AB, Kamtchouing P, Kamanyi A (2010) In vitro antioxidant activity of extracts and coumarins from Mammea africana sabine. J Compl Integr Med. doi:10.2202/155338401447

    Google Scholar 

  • Nono NR, Nzowa KL, Barboni L, Tapondjou AL (2014a) Drymaria cordata (Linn.)Willd (Caryophyllaceae): ethnobotany. Pharmacol Phytochem Adv Biol Chem 4:160–167

    Article  Google Scholar 

  • Nono RN, Barboni L, Teponno RB, Quassinti L, Bramucci M, Vitali LA, Petrelli D, Lupidi G, Tapondjou AL (2014b) Antimicrobial, antioxidant, anti-inflammatory activities and phytoconstituents of extracts from the roots of Dissotis thollonii Cogn. (Melastomataceae). S Afr J Bot 93:19–26

    Article  CAS  Google Scholar 

  • Nzowa LK, Teponno RB, Tapondjou LA, Verotta L, Liao Z, Graham D, Zink M-C, Barboni L (2013) Two new tryptophan derivatives from the seed kernels of Entada rheedei: effects on cell viability and HIV infectivity. Fitoterapia 87:37–42

    Article  PubMed  CAS  PubMed Central  Google Scholar 

  • Sahu VK, Irchhaiya R, Shashi A, Gurjar H (2010) Phytochemical investigation and chromatographic evaluation of the ethanolic extract of whole plant extract of Dendrophthoe falcata (L.F.) Ettingsh. Int J Pharm Pharmaceut Sci 1:39–45

    CAS  Google Scholar 

  • Shankar R, Rawat MS (2008) Ethnobotanical observations of Drymaria cordata Willd. Ex Roem & Schult. (Caryophyllaceae). Bull Arunachal For Res 24:22–24

    Google Scholar 

  • Sowemimo A, Van de Venter M, Baatjies L, Koekemoer T (2009) Cytotoxic activity of selected Nigerian plants. Afr J Trad Compl Alt Med 6:526–528

    CAS  Google Scholar 

  • Tapondjou AL, Kristina JS, Böttger S, Melzig MF (2013) Steroidal saponins from the flowers of Dioscorea bulbifera var.sativa. Phytochemistry 95:341–350

    Article  PubMed  CAS  Google Scholar 

  • Teponno RB, Ponou KB, Tapondjou AL, Barboni L (2013) Bafoudiosbulbin H, a new clerodane diterpene from the flowers of Dioscorea bulbifera var. sativa. Phytochem lett 6:310–314

    Article  CAS  Google Scholar 

  • Zeng P, Zhang Y, Pan C, Jia Q, Guo F, Li Y, Zhu W, Chen K (2013) Advances in studying of the pharmacological activities and structure-activity-relationships of natural C-glycosyl flavonoids. Acta Pharmaceut Sin B 3:154–162

    Article  Google Scholar 

  • Zhang A, Zhu QY, Luk YS, Ho KY, Fung KP, Chen Z-Y (1997) Inhibitory effects of jasmine green tea epicatechin isomers on free radical-induced lysis of red blood cells. Life Sci 61:383–394

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This research work was supported by the IFS (International Foundation for Science, Stockholm, Sweden) program through a grant to Prof. A. Léon TAPONDJOU (RGA No. F/3976-3F) and the Italian Ministry of Education (MIUR) (COOPERLINK 2011 Prot. CII113PPUC).

Author information

Authors and Affiliations

  1. Laboratory of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Box 183, Dschang, Cameroon

    Raymond N. Nono, Laurence K. Nzowa, Beaudelaire K. Ponou, Rémy B. Teponno & Léon A. Tapondjou

  2. Laboratory of Animal Physiology and Phytopharmacology, Department of Animal Biology, Faculty of Science, University of Dschang, Box 67, Dschang, Cameroon

    Elvine P. Nguelefack-Mbuyo & Télesphore B. Nguelefack

  3. School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032, Camerino, Italy

    Luciano Barboni

  4. Department of Pharmaceutical Engineering, Sandji University, Wonju, 220-702, Republic of Korea

    Hee-Juhn Park

Authors
  1. Raymond N. Nono
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elvine P. Nguelefack-Mbuyo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Laurence K. Nzowa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Beaudelaire K. Ponou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rémy B. Teponno
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Télesphore B. Nguelefack
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Luciano Barboni
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Léon A. Tapondjou
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Hee-Juhn Park
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Léon A. Tapondjou or Hee-Juhn Park.

Ethics declarations

Conflict of Interest

The authors declare no competing financial interest.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary Fig. 1

Supplementary Material (doc 133kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nono, R.N., Nguelefack-Mbuyo, E.P., Nzowa, L.K. et al. Antioxidant C-glycosylflavones of Drymaria cordata (Linn.) Willd. Arch. Pharm. Res. 39, 43–50 (2016). https://doi.org/10.1007/s12272-015-0691-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-015-0691-7

Keywords

Search

Navigation