Cytotoxic withanolides from the leaves of Moroccan Withania frutescens

Pharmaceutical Biology

Volumn 51, Issue 8, 2013, Pages 1040-1046

  El Bouzidi, Laila ^a   Mahiou Leddet, Valérie ^b   Bun, Sok Siya ^b   Larhsini, Mustapha ^a   Abbad, Abdelaziz ^a   Markouk, Mohammed ^a   Fathi, Mabrouki ^b   Boudon, Michèle ^b   Ollivier, Evelyne ^b   Bekkouche, Khalid ^a  

^a CADI AYYAD UNIVERSITY   (Morocco)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Cancer cell lines; Cytotoxic activity; MTT assay; Steroidal lactones

Indexed keywords

2,3 DIHYDROXYWITHAFERIN A 3BETA O SULFATE; 4BETA,17ALPHA,27 TRIHYDROXY 1 OXO 22 WITHA 2,5,24 TRIENOLIDE; 5BETA,6BETA EPOXY 4BETA,17ALPHA,27 TRIHYDROXY 1 OXOWITHA 2,24 DIENOLIDE; ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; FLUOROURACIL; PLANT EXTRACT; UNCLASSIFIED DRUG; WITHANIA FRUTESCENS EXTRACT;

ARTICLE; CELL STRAIN HEPG2; CELL STRAIN HT29; COLUMN CHROMATOGRAPHY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PLANT LEAF; WITHANIA; WITHANIA FRUTESCENS;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CARCINOMA, HEPATOCELLULAR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLONIC NEOPLASMS; FLUOROURACIL; HEP G2 CELLS; HT29 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LIVER NEOPLASMS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOROCCO; PLANT LEAVES; SOLVENTS; WITHANIA; WITHANOLIDES;

EID: 84885391598     PISSN: 13880209     EISSN: 17445116     Source Type: Journal    
DOI: 10.3109/13880209.2013.775162     Document Type: Article

References (32)

1. Abdeljebbar LH, Human M, Christen P, et al. (2007). Withanolides from Withania adpressa. Helv Chim Acta 90:346-52.
2. Abdeljebbar LH, Benjouad A, Morjani H, et al. (2009). Antiproliferative effects of withanolides from Withania adpressa. Therapie 64:121-7.
3. Anjaneyulu ASR, Rao DS, Lequesne PW. (1998). Withanolides, biologically active natural steroidal lactones: A review. In: Atta-ur- Rahman, ed. Studies in Natural Products Chemistry. BV Amsterdam: Elsevier Science, 20, 135-261.
4. Bekkouche K, Daali Y, Cherkaoui S, et al. (2001). Calystegine distribution in some Solanaceous species. Phytochemistry 58:455-62.
5. Bellakhdar J. (1997). La Pharmacopée Marocaine Traditionnelle, Médicine arabe ancienne et savoirs. Paris: Ibis Press.
6. Chen LX, He H, Qiu F. (2011). Natural withanolides: An overview. Nat Prod Rep 28:705-40.
7. Choudhary MI, Sammer Y, Nawaz SA, et al. (2004). Cholinesterase inhibiting withanolides from Withania somnifera. Chem Pharm Bull 52:1358-61.
8. Cordero CP, Morantes SJ, Páez A, et al. (2009). Cytotoxicity of withanolides isolated from Acnistus arborescens. Fitoterapia 80: 364-8.
9. Eich E. (2008). Solanaceae and Convolvulaceae Secondary Metabolites: Biosynthesis, Chemotaxonomy, Biological and Economic Significance. Berlin-Heidelberg: Springer-Verlag.
10. El Bouzidi L, Larhsini M, Markouk M, et al. (2011). Antioxidant and antimicrobial activities of Withania frutescens. Nat Prod Commun 16: 1447-50.
11. Glotter E. (1991). Withanolides and related ergostane-type steroids. Nat Prod Rep 8:415-40.
12. González AG, Bretón JL, Trujillo J. (1972). Withanolidos de las Withania aristata Pauq. Y Withania frutescens Pauq. An Quím 68: 107-8.
13. González AG, Bretón JL, Trujillo J. (1974). Withania steroids. III. Steroidal lactones of Withania frutescens. Quím 70:69-73.
14. González AG, Darias V, Martin H, Suarez MC. (1982). Cytostatic activity of natural withanolides from Spanish Withania. Fitoterapia 53:85-88.
15. Hepper FN. (1991). Old World Withania (Solanaceae): A taxonomic review and key to the species. In: Hawkes JG, Lester RN, Nee M, Estrada N, eds. Solanaceae III Taxonomy, Chemistry, Evolution. Hawkes, Kew, UK: Royal Botanic Gardens. Richmond, Surrey, UK for the Linnean Society of London, London, 211-28.
16. Khan PM, Ahmad S, Rubnawaz H, Malik A. (1999). The first report of a withanolide from the family Labiatae. Phytochemistry 51: 669-71.
17. Ksebati MB, Schmitz FJ. (1988). Minabeolides: A group of withanolides from a soft coral, Minabea sp. J Org Chem 53:3926-9.
18. Llanos GG, Araujo LM, Jiménez IA, et al. (2012). Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells. Eur J Med Chem 54: 499-511.
19. Machin RP, Veleiro AS, Nicotra VE, et al. (2010). Antiproliferative activity of withanolides against human breast cancer cell lines. J Nat Prod 73:966-8.
20. Misra L, Lal P, Sangwan RS, et al. (2005). Unusually sulfated and oxygenated steroids from Withania somnifera. Phytochemistry 66: 2702-7.
21. Montilla MP, Cabo J, Navarro MC, et al. (1990). The protective and curative action of Withania frutescens leaf extract against CCl4-induced hepatotoxicity. Phytother Res 4:212-15.
22. Nakano D, Ishitsuka K, Katsuya H, et al. (2012). Screening of promising chemotherapeutic candidates from plants against human adult T-cell leukemia/lymphoma (II): Apoptosis of antiproliferative principle (24, 25-dihydrowithanolide D) against ATL cell lines and structure- activity relationships with withanolides isolated from solanaceous plants. J Nat Med. DOI 10.1007/s11418-012-0700-9.
23. Pelletier SW, Gebeyehu G, Nowacki J, Mody NV. (1981). Viscosalactone A and viscosalactone B, two new steroidal lactones from Physalis viscosa. Heterocycles 15:317-20.
24. Ray AB, Gupta M. (1994). Withasteroids, a group of naturally occurring steroidal lactones. Prog Chem Org Nat Prod 63:1-106.
25. Shingu K, Furusawa Y, Nohara T. (1989). New withanolides, daturametelins C, D, E, F and G- Ac from Datura metel L. (Solanaceous studies. XIV). Chem Pharm Bull 37:2132-5.
26. Suleiman RK, Zarga MA, Sabri SS. (2010). New withanolides from Mandragora officinarum: First report of withanolides from the genus Mandragora. Fitoterapia 81:864-8.
27. Vankar PS, Srivastava J, Molčanov K, Kojic-Prodic B. (2009). Withanolide A series steroidal lactones from Eucalyptus globulus bark. Phytochem Lett 2:67-71.
28. Veleiro AS, Oberti JC, Burton G. (2005). Chemistry and bioactivity of withanolides from South American Solanaceae. In: Atta-ur-Rahman, ed. Studies in Natural Products Chemistry. BV Amsterdam: Elsevier Science, 32, 1019-52.
29. Xu Y, Marron MT, Seddon E, et al. (2009). 2, 3-Dihydrowithaferin A-3b-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera. Bioorg Med Chem 17: 2210-4.
30. Xu Y, Gao S, Bunting DP, Gunatilaka AAL. (2011). Unusual withanolides from aeroponically grown Withania somnifera. Phytochemistry 72:518-22.
31. Yokosuka A, Mimaki Y, Sashida Y. (2003). Chantriolides A and B, Two new withanolide glucosides from the rhizomes of Tacca chantrieri. J Nat Prod 66:876-78.
32. Zhang H, Samadi AK, Cohen MS, Timmermann BN. (2012). Antiproliferative withanolides from the Solanaceae: A structure- activity study. Pure Appl Chem 84:1353-67.