Glycosylation of ent-kaurene derivatives and an evaluation of their cytotoxic activities

Chinese Journal of Natural Medicines

Volumn 11, Issue 3, 2013, Pages 289-295

  Zou, Min ^a   Yu, Shuang Shuang ^a   Wang, Ke ^a   Zhang, Da Yong ^a   Wu, Xiao Ming ^a   Hua, Wei Yi ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Cytotoxic activity; Exo Methylene cyclopentanone; Glycosylation; Isosteviol; Steviol; Stevioside; Tetracyclic diterpenoids; Methylenelactone

Indexed keywords

CARBOXYL GROUP; CUCURBITACIN GLUCOSIDE B; DOXORUBICIN; GLUCOSE ASPIRIN; KAURENE DERIVATIVE; STEVIOLBIOSIDE STEARYLAMIDE; STEVIOSIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; EVALUATION; GLYCOSYLATION; HUMAN; HUMAN CELL; IC 50; NITROBLUE TETRAZOLIUM TEST;

EID: 84878431672     PISSN: 20956975     EISSN: 18755364     Source Type: Journal    
DOI: 10.1016/S1875-5364(13)60031-X     Document Type: Article

References (15)

1. Li XL, Yin QM, Jiao LL, et al. A convenient synthesis of novel thiazolidin-4-one-linked pseudodisaccharides by tandem Staudinger/aza-Wittig/cyclization and their biological evaluation [J]. Carbohydr Res 2011, 346(3):401-409.
2. Jacob JN, Tazawa MJ Glucose-aspirin: Synthesis and in vitro anti-cancer activity studies [J]. Bioorg Med Chem Lett 2012, 22(9):3168-3171.
3. Tehila TS, Shlomo G, Sara D, et al. Growth inhibitory activity of cucurbitacin glucosides isolated from Citrullus colocynthis on human breast cancer cells [J]. Biochem Pharmacol 2007, 73(1):56-67.
4. Lin LH, Lee LW, Sheu SY, et al. Study on the stevioside analogues of steviolbioside, steviol, and isosteviol 19-alkyl amide dimers: synthesis and cytotoxic and antibacterial activity [J]. Chem Pharm Bull 2004, 52(9):1117-1122.
5. Brahmachari G, Mandal LC, Roy R, et al. Stevioside and related compounds -molecules of pharmaceutical promise: a critical overview [J]. Arch Pharm Chem Life Sci 2011, 344(1):5-19.
6. Boonkaewwan C, Ao M, Toskulkao C, et al. Specific immunomodulatory and secretory activities of stevioside and steviol in intestinal cells [J]. J Agric Food Chem 2008, 56(10):3777-3784.
7. Roberto LM, Antonio VG, Liliana ZB, et al. Stevia rebaudiana Bertoni, source of a high-potency natural sweetener: A comprehensive review on the biochemical, nutritional and functional aspects [J]. Food Chem 2012, 132(3):1121-1132.
8. Wang ZQ, Xue LQ, Guo CC, et al. Stevioside ameliorates high-fat diet-induced insulin resistance and adipose tissue inflammation by downregulating the NF-κB pathway [J]. Biochem Biophys Res Commun 2012, 417(4):1280-1285.
9. Brusick DJ A critical review of the genetic toxicity of steviol and steviol glycosides [J]. Food Chem Toxicol 2008, 46(7):S83-S91.
10. Pól J, Hohnová B, Hyötyläinen T Characterisation of Stevia rebaudiana by comprehensive two-dimensional liquid chromatography time-of-flight mass spectrometry [J]. J Chromatogr A 2007, 1150(1-2):85-92.
11. Takasaki M, Konoshima T, Kozuka M, et al. Cancer preventive agents. Part 8: Chemopreventive effects of stevioside and related compounds [J]. Bioorg Med Chem 2009, 17(2):600-605.
12. Li J, Zhang DY, Wu XM Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents [J]. Bioorg Med Chem Lett 2011, 21(1):130-132.
13. Zeng YF, Wu JQ, Shi LY, et al. Synthesis and evaluation of cytotoxic effects of novel α-methylenelactone tetracyclic diterpenoids [J]. Bioorg Med Chem Lett 2012, 22(5):1922-1925.
14. DuBois GE, Stephenson RA Diterpenoid sweeteners. synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties [J]. J Med Chem 1985, 28(1):93-98.
15. Liu PL, Maurits V Cyclohexane polyols: Enantioselective synthesis of (+)-fortamine and of pseudosugars [J]. Tetrahedron 1994, 50(24):7061-7074.