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Isochamaejasmin and other flavonoids isolated from an endemic Algerian desert species

Yıl 2018, Cilt: 5 Sayı: 2, 347 - 354, 01.01.2018
https://doi.org/10.18596/jotcsa.351651

Öz

Thymelaea
microphylla
Coss. et Dur is an endemic desert species from Algeria belongs to Thymelaeaceae
family. The dichloromethane-methanolic extract from aerial parts of T.
microphylla
was subjected to silica gel column. Three flavonoids were
isolated from the extract; isochamaejasmin (1), cis-tiliroside (2) and
trans-tiliroside (3). The structures of the compounds were determined on the
basis of the HPLC-TOF/MS, 1D and 2D NMR spectroscopic analysis. To the best of
our knowledge, compound (1) was isolated from T. microphylla for the
first time and 
there is no report in the literature. Moreover, in
this study, antioxidant activity of the compound (3) was also evaluated.

Kaynakça

  • 1. Borris RP, Blaskó G, Cordell GA. Ethnopharmacologic and phytochemical studies of the Thymelaeaceae. Journal of Ethnopharmacology. 1988;24(1):41-91.
  • 2. Takeuchi W, Golman M. The identity of eaglewood (Gyrinops, Thymelaeaceae), a new economic resource for Papua New Guinea. SIDA, Contributions to Botany. 2002;20(1):261-7.
  • 3. Bredenkamp CL, van Wyk AE. Taxonomy of the genus Passerina (Thymelaeaceae). Bothalia: African Biodiversity & Conservation. 2003;33:53-7.
  • 4. Vincent MA, Thieret JW. Thymelaea passerina (Thymelaeaceae) in Ohio. SIDA, Contributions to Botany. 1987;12(1):75-8.
  • 5. Bnouham M, Benalla W, Bellahcen S, Hakkou Z, Ziyyat A, Mekhfi H, et al. Antidiabetic and antihypertensive effect of a polyphenol-rich fraction of Thymelaea hirsuta L. in a model of neonatal streptozotocin-diabetic and NG-nitro-l-arginine methyl ester-hypertensive rats. Journal of Diabetes. 2012;4(3):307-13.
  • 6. Dehimi K, Speciale A, Saija A, Dahamna S, Raciti R, Cimino F, et al. Antioxidant and anti-inflammatory properties of Algerian Thymelaea microphylla Coss. and Dur. extracts. Pharmacognosy Magazine. 2016;12(47):203-10.
  • 7. Trigui M, Hsouna AB, Tounsi S, Jaoua S. Chemical composition and evaluation of antioxidant and antimicrobial activities of Tunisian Thymelaea hirsuta with special reference to its mode of action. Industrial Crops and Products. 2013;41:150-7.
  • 8. Ghanem H, Haba H, Marcourt L, Benkhaled M, Wolfender JL. Microphynolides A and B, new spiro-gamma-lactone glycosides from Thymelaea microphylla. Natural Product Research. 2014;28(20):1732-8.
  • 9. Noman L, Zellagui A, Hallis Y, Yaglioglu AS, Demirtas I, Gherraf N, et al. Antioxidant and antimicrobial activities of an endemic desert species Thymelea microphylla Coss. et Dur. Der Pharmacia Lettre. 2015; 7(1):118-21.
  • 10. Kerbab K, Mekhelfi T, Zaiter L, Benayache S, Benayache F, Picerno P, et al. Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. et Dur. Natural Product Research. 2015;29(7):671-5.
  • 11. Noman L, Oke-Altuntas F, Zellagui A, Sahin Yaglioglu A, Demirtas I, M Cardoso S, et al. A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur. Natural Product Research. 2017;31:2032-41.
  • 12. Rizk A, Hammouda F, Ismail S. Phytochemical investigation of Thymelea hirsuta. 3. Coumarins. Acta Chimica Academiae Scientarium Hungaricae. 1975;85(1):107-15.
  • 13. Labib SN, Zellagui A, Mesbah K, Gherraf N, Lahouel Mand Rhouati S. Essential oil Composition of Thymelea microphylla Coss et Dur. Der Pharmacia Lettre. 2010;2(5):428-31.
  • 14. Blois MS. Antioxidant determinations by the use of a stable free radical. Nature. 1958;181:1199-200.
  • 15. Decker EA, Welch B. Role of ferritin as a lipid oxidation catalyst in muscle food. Journal of Agricultural and Food Chemistry. 1990;38(3):674-7.
  • 16. Agrawal PK. Flavonoid glycosides. Carbon-13 NMR of flavonoids. Amsterdam, Elsevier, 1989, pp. 102–103.
  • 17. Niwa M, Otsuji S, Tatematsu H, Liu G-Q, Chen X-F, Hirata Y. Stereostructures of two biflavanones from Stellera chamaejasme L. Chemical and Pharmaceutical Bulletin. 1986;34(8):3249-51.
  • 18. Trendafilova A, Todorova M, Gavrilova A, Vitkova A. Flavonoid glycosides from Bulgarian endemic Alchemilla achtarowii Pawl. Biochemical Systematics and Ecology. 2012;43:156-8.
  • 19. Liao C-R, Kuo Y-H, Ho Y-L, Wang C-Y, Yang C-S, Lin C-W, et al. Studies on cytotoxic constituents from the leaves of Elaeagnus oldhamii Maxim. in non-small cell lung cancer A549 cells. Molecules. 2014;19(7):9515-34.
  • 20. Qiao W, Zhao C, Qin N, Zhai HY, Duan HQ. Identification of trans-tiliroside as active principle with anti-hyperglycemic, anti-hyperlipidemic and antioxidant effects from Potentilla chinesis. Journal of Ethnopharmacology. 2011;135(2):515-21.
  • 21. Sala A, Recio MC, Schinella GR, Máñez S, Giner RM, Cerdá-Nicolás M, et al. Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside. European Journal of Pharmacology. 2003;461(1):53-61.
  • 22. Mekhelfi T, Adouni K, Zaiter L, Guella G, Benayache S, Benayache F, Venskutonis PR. Antioxidant activity of extracts, cis and trans tilirosides, and other compounds from Thymelaea microphylla Coss. et Dur. Der Pharmacia Lettre. 2016;8:233-9.
Yıl 2018, Cilt: 5 Sayı: 2, 347 - 354, 01.01.2018
https://doi.org/10.18596/jotcsa.351651

Öz

Kaynakça

  • 1. Borris RP, Blaskó G, Cordell GA. Ethnopharmacologic and phytochemical studies of the Thymelaeaceae. Journal of Ethnopharmacology. 1988;24(1):41-91.
  • 2. Takeuchi W, Golman M. The identity of eaglewood (Gyrinops, Thymelaeaceae), a new economic resource for Papua New Guinea. SIDA, Contributions to Botany. 2002;20(1):261-7.
  • 3. Bredenkamp CL, van Wyk AE. Taxonomy of the genus Passerina (Thymelaeaceae). Bothalia: African Biodiversity & Conservation. 2003;33:53-7.
  • 4. Vincent MA, Thieret JW. Thymelaea passerina (Thymelaeaceae) in Ohio. SIDA, Contributions to Botany. 1987;12(1):75-8.
  • 5. Bnouham M, Benalla W, Bellahcen S, Hakkou Z, Ziyyat A, Mekhfi H, et al. Antidiabetic and antihypertensive effect of a polyphenol-rich fraction of Thymelaea hirsuta L. in a model of neonatal streptozotocin-diabetic and NG-nitro-l-arginine methyl ester-hypertensive rats. Journal of Diabetes. 2012;4(3):307-13.
  • 6. Dehimi K, Speciale A, Saija A, Dahamna S, Raciti R, Cimino F, et al. Antioxidant and anti-inflammatory properties of Algerian Thymelaea microphylla Coss. and Dur. extracts. Pharmacognosy Magazine. 2016;12(47):203-10.
  • 7. Trigui M, Hsouna AB, Tounsi S, Jaoua S. Chemical composition and evaluation of antioxidant and antimicrobial activities of Tunisian Thymelaea hirsuta with special reference to its mode of action. Industrial Crops and Products. 2013;41:150-7.
  • 8. Ghanem H, Haba H, Marcourt L, Benkhaled M, Wolfender JL. Microphynolides A and B, new spiro-gamma-lactone glycosides from Thymelaea microphylla. Natural Product Research. 2014;28(20):1732-8.
  • 9. Noman L, Zellagui A, Hallis Y, Yaglioglu AS, Demirtas I, Gherraf N, et al. Antioxidant and antimicrobial activities of an endemic desert species Thymelea microphylla Coss. et Dur. Der Pharmacia Lettre. 2015; 7(1):118-21.
  • 10. Kerbab K, Mekhelfi T, Zaiter L, Benayache S, Benayache F, Picerno P, et al. Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. et Dur. Natural Product Research. 2015;29(7):671-5.
  • 11. Noman L, Oke-Altuntas F, Zellagui A, Sahin Yaglioglu A, Demirtas I, M Cardoso S, et al. A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur. Natural Product Research. 2017;31:2032-41.
  • 12. Rizk A, Hammouda F, Ismail S. Phytochemical investigation of Thymelea hirsuta. 3. Coumarins. Acta Chimica Academiae Scientarium Hungaricae. 1975;85(1):107-15.
  • 13. Labib SN, Zellagui A, Mesbah K, Gherraf N, Lahouel Mand Rhouati S. Essential oil Composition of Thymelea microphylla Coss et Dur. Der Pharmacia Lettre. 2010;2(5):428-31.
  • 14. Blois MS. Antioxidant determinations by the use of a stable free radical. Nature. 1958;181:1199-200.
  • 15. Decker EA, Welch B. Role of ferritin as a lipid oxidation catalyst in muscle food. Journal of Agricultural and Food Chemistry. 1990;38(3):674-7.
  • 16. Agrawal PK. Flavonoid glycosides. Carbon-13 NMR of flavonoids. Amsterdam, Elsevier, 1989, pp. 102–103.
  • 17. Niwa M, Otsuji S, Tatematsu H, Liu G-Q, Chen X-F, Hirata Y. Stereostructures of two biflavanones from Stellera chamaejasme L. Chemical and Pharmaceutical Bulletin. 1986;34(8):3249-51.
  • 18. Trendafilova A, Todorova M, Gavrilova A, Vitkova A. Flavonoid glycosides from Bulgarian endemic Alchemilla achtarowii Pawl. Biochemical Systematics and Ecology. 2012;43:156-8.
  • 19. Liao C-R, Kuo Y-H, Ho Y-L, Wang C-Y, Yang C-S, Lin C-W, et al. Studies on cytotoxic constituents from the leaves of Elaeagnus oldhamii Maxim. in non-small cell lung cancer A549 cells. Molecules. 2014;19(7):9515-34.
  • 20. Qiao W, Zhao C, Qin N, Zhai HY, Duan HQ. Identification of trans-tiliroside as active principle with anti-hyperglycemic, anti-hyperlipidemic and antioxidant effects from Potentilla chinesis. Journal of Ethnopharmacology. 2011;135(2):515-21.
  • 21. Sala A, Recio MC, Schinella GR, Máñez S, Giner RM, Cerdá-Nicolás M, et al. Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside. European Journal of Pharmacology. 2003;461(1):53-61.
  • 22. Mekhelfi T, Adouni K, Zaiter L, Guella G, Benayache S, Benayache F, Venskutonis PR. Antioxidant activity of extracts, cis and trans tilirosides, and other compounds from Thymelaea microphylla Coss. et Dur. Der Pharmacia Lettre. 2016;8:233-9.
Toplam 22 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Feyza Oke-altuntas

Labib Noman Bu kişi benim

Amar Zellagui Bu kişi benim

Ibrahim Demirtas

Rhouati Salah Bu kişi benim

Yayımlanma Tarihi 1 Ocak 2018
Gönderilme Tarihi 13 Kasım 2017
Kabul Tarihi 7 Şubat 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 5 Sayı: 2

Kaynak Göster

Vancouver Oke-altuntas F, Noman L, Zellagui A, Demirtas I, Salah R. Isochamaejasmin and other flavonoids isolated from an endemic Algerian desert species. JOTCSA. 2018;5(2):347-54.