New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)

Yanna C. F. Teles, Carolina Campolina Rebello Horta, Maria de Fátima Agra, Weam Siheri, Marie Boyd, John O. Igoli, Alexander I. Gray, Maria de Fátima Vanderlei de Souza

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Wissadula periplocifolia (L.) C. Presl (Malvaceae) is commonly used in Brazil to treat bee stings and as an antiseptic. The antioxidant properties of its extracts have been previously demonstrated, thus justifying a phytochemical investigation for its bioactive phenolic constituents. This has yielded five new sulphated flavonoids: 8-O-sulphate isoscutellarein (yannin) (1a); 4'-O-methyl-7-O-sulphate isoscutellarein (beltraonin) (1b); 7-O-sulphate acacetin (wissadulin) (2a); 4'-O-methyl-8-O-sulphate isoscutellarein (caicoine) (2b) and 3'-O-methyl-8-O-sulphate hypolaetin (pedroin) (3b) along with the known flavonoids 7,4'-di-O-methyl-8-O-sulphate isoscutellarein (4), acacetin, apigenin, isoscutellarein, 4´-O-methyl isoscutellarein, 7,4'-di-O-methylisoscutellarein, astragalin and tiliroside. The compounds were isolated by column chromatography and identified by NMR (¹H, (13)C, HMQC, HMBC and COSY) and LC-HRMS. A cell based assay was carried out to evaluate the preliminary cytotoxic properties of the flavonoids against UVW glioma and PC-3M prostate cancer cells as well as non-tumour cell lines. The obtained results showed that acacetin, tiliroside, a mixture of acacetin + apigenin and the sulphated flavonoids 2a + 2b exhibited inhibitory activity against at least one of the cell lines tested. Among the tested flavonoids acacetin and tiliroside showed lower IC50 values, presenting promising antitumor effects.

LanguageEnglish
Pages20161-20172
Number of pages12
JournalMolecules
Volume20
Issue number11
DOIs
Publication statusPublished - 9 Nov 2015

Fingerprint

Malvaceae
Flavonoids
Sulfates
sulfates
Apigenin
Cells
cultured cells
antiseptics
bees
Cell Line
Column chromatography
Local Anti-Infective Agents
Bees
antioxidants
Phytochemicals
Brazil
Bites and Stings
chromatography
activity (biology)
Glioma

Keywords

  • Wissadula periplocifolia
  • sulphated flavonoids
  • isoscutellarein derivatives

Cite this

Teles, Y. C. F., Horta, C. C. R., Agra, M. D. F., Siheri, W., Boyd, M., Igoli, J. O., ... de Souza, M. D. F. V. (2015). New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). Molecules, 20(11), 20161-20172. https://doi.org/10.3390/molecules201119685
Teles, Yanna C. F. ; Horta, Carolina Campolina Rebello ; Agra, Maria de Fátima ; Siheri, Weam ; Boyd, Marie ; Igoli, John O. ; Gray, Alexander I. ; de Souza, Maria de Fátima Vanderlei. / New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). In: Molecules. 2015 ; Vol. 20, No. 11. pp. 20161-20172.
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Teles, YCF, Horta, CCR, Agra, MDF, Siheri, W, Boyd, M, Igoli, JO, Gray, AI & de Souza, MDFV 2015, 'New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)' Molecules, vol. 20, no. 11, pp. 20161-20172. https://doi.org/10.3390/molecules201119685

New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). / Teles, Yanna C. F.; Horta, Carolina Campolina Rebello; Agra, Maria de Fátima; Siheri, Weam; Boyd, Marie; Igoli, John O.; Gray, Alexander I.; de Souza, Maria de Fátima Vanderlei.

In: Molecules, Vol. 20, No. 11, 09.11.2015, p. 20161-20172.

Research output: Contribution to journalArticle

TY - JOUR

T1 - New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)

AU - Teles, Yanna C. F.

AU - Horta, Carolina Campolina Rebello

AU - Agra, Maria de Fátima

AU - Siheri, Weam

AU - Boyd, Marie

AU - Igoli, John O.

AU - Gray, Alexander I.

AU - de Souza, Maria de Fátima Vanderlei

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AB - Wissadula periplocifolia (L.) C. Presl (Malvaceae) is commonly used in Brazil to treat bee stings and as an antiseptic. The antioxidant properties of its extracts have been previously demonstrated, thus justifying a phytochemical investigation for its bioactive phenolic constituents. This has yielded five new sulphated flavonoids: 8-O-sulphate isoscutellarein (yannin) (1a); 4'-O-methyl-7-O-sulphate isoscutellarein (beltraonin) (1b); 7-O-sulphate acacetin (wissadulin) (2a); 4'-O-methyl-8-O-sulphate isoscutellarein (caicoine) (2b) and 3'-O-methyl-8-O-sulphate hypolaetin (pedroin) (3b) along with the known flavonoids 7,4'-di-O-methyl-8-O-sulphate isoscutellarein (4), acacetin, apigenin, isoscutellarein, 4´-O-methyl isoscutellarein, 7,4'-di-O-methylisoscutellarein, astragalin and tiliroside. The compounds were isolated by column chromatography and identified by NMR (¹H, (13)C, HMQC, HMBC and COSY) and LC-HRMS. A cell based assay was carried out to evaluate the preliminary cytotoxic properties of the flavonoids against UVW glioma and PC-3M prostate cancer cells as well as non-tumour cell lines. The obtained results showed that acacetin, tiliroside, a mixture of acacetin + apigenin and the sulphated flavonoids 2a + 2b exhibited inhibitory activity against at least one of the cell lines tested. Among the tested flavonoids acacetin and tiliroside showed lower IC50 values, presenting promising antitumor effects.

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KW - isoscutellarein derivatives

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Teles YCF, Horta CCR, Agra MDF, Siheri W, Boyd M, Igoli JO et al. New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). Molecules. 2015 Nov 9;20(11):20161-20172. https://doi.org/10.3390/molecules201119685