Isochamaejasmin and other flavonoids isolated from an endemic Algerian desert species

Feyza Oke-altuntas; Labib Noman; Amar Zellagui; Ibrahim Demirtas; Rhouati Salah

doi:10.18596/jotcsa.351651

Research Article

Isochamaejasmin and other flavonoids isolated from an endemic Algerian desert species

Year 2018, Volume: 5 Issue: 2, 347 - 354, 01.01.2018

Feyza Oke-altuntas Labib Noman Amar Zellagui Ibrahim Demirtas Rhouati Salah

https://doi.org/10.18596/jotcsa.351651

Abstract

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.

Keywords

Thymelaea microphylla, flavonoids, antioxidant

References

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.

Year 2018, Volume: 5 Issue: 2, 347 - 354, 01.01.2018

Feyza Oke-altuntas Labib Noman Amar Zellagui Ibrahim Demirtas Rhouati Salah

https://doi.org/10.18596/jotcsa.351651

Abstract

References

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.

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Details

Primary Language	English
Subjects	Chemical Engineering
Journal Section	Articles
Authors	Feyza Oke-altuntas Labib Noman This is me Amar Zellagui This is me Ibrahim Demirtas Rhouati Salah This is me
Publication Date	January 1, 2018
Submission Date	November 13, 2017
Acceptance Date	February 7, 2018
Published in Issue	Year 2018 Volume: 5 Issue: 2

Cite

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.

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