Bioactive limonoids from the leaves of Azaridachta indica (Neem).

Eight new limonoids (1-8) and one new phenol glycoside (9), along with six known compounds, were isolated from the leaves of Azaridachta indica. The structures of 1-9 were elucidated on the basis of spectroscopic data analysis. Compounds isolated were assayed for their cytotoxicity against different cancer cell lines. Moreover, their ability to interact with the molecular chaperone Hsp90, affecting its biological activity, was tested.

[1]  K. Koike,et al.  Limonoids from the fruits of Melia azedarach and their cytotoxic activities. , 2013, Phytochemistry.

[2]  G. Bifulco,et al.  A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors. , 2013, Journal of medicinal chemistry.

[3]  G. Bifulco,et al.  Natural Iminosugar (+)-Lentiginosine Inhibits ATPase and Chaperone Activity of Hsp90 , 2012, PloS one.

[4]  G. Bifulco,et al.  Structural characterization of tetranortriterpenes from Pseudrocedrela kotschyi and Trichilia emetica and study of their activity towards the chaperone Hsp90. , 2012, Phytochemistry.

[5]  Alison Stopeck,et al.  HSP90 Inhibition Is Effective in Breast Cancer: A Phase II Trial of Tanespimycin (17-AAG) Plus Trastuzumab in Patients with HER2-Positive Metastatic Breast Cancer Progressing on Trastuzumab , 2011, Clinical Cancer Research.

[6]  M. F. G. F. Silva,et al.  Simultaneous quantification of azadirachtin and 3-tigloylazadirachtol in Brazilian seeds and oil of Azadirachta indica: application to quality control and marketing , 2010 .

[7]  S. Nagini,et al.  Nimbolide a limonoid from Azadirachta indica inhibits proliferation and induces apoptosis of human choriocarcinoma (BeWo) cells , 2009, Investigational New Drugs.

[8]  B. Blagg,et al.  Gedunin, a novel hsp90 inhibitor: semisynthesis of derivatives and preliminary structure-activity relationships. , 2008, Journal of medicinal chemistry.

[9]  M. Gopalakrishnan,et al.  Evaluation of Azadirachta indica leaf fractions for in vitro antioxidant potential and in vivo modulation of biomarkers of chemoprevention in the hamster buccal pouch carcinogenesis model. , 2008, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[10]  Xiao Ming Yu,et al.  A non-toxic Hsp90 inhibitor protects neurons from Abeta-induced toxicity. , 2007, Bioorganic & medicinal chemistry letters.

[11]  J. Kersey,et al.  Synergism between Etoposide and 17-AAG in Leukemia Cells: Critical Roles for Hsp90, FLT3, Topoisomerase II, Chk1, and Rad51 , 2007, Clinical Cancer Research.

[12]  Rajwinder Singh,et al.  Bioefficacy and mode-of-action of some limonoids of salannin group fromAzadirachta indica A. Juss and their role in a multicomponent system against lepidopteran larvae , 2004, Journal of Biosciences.

[13]  Tahsin Gulzar,et al.  Tetracyclic triterpenoids from the leaves of Azadirachta indica. , 2004, Phytochemistry.

[14]  Hong Zhang,et al.  Targeting multiple signal transduction pathways through inhibition of Hsp90 , 2004, Journal of Molecular Medicine.

[15]  A. Venkateswarlu,et al.  Biological investigation and structure-activity relationship studies on azadirone from Azadirachta indica A. Juss. , 2003, Bioorganic & medicinal chemistry letters.

[16]  R. Sultana,et al.  Tetracyclic triterpenoids from the leaves of Azadirachta indica and their insecticidal activities. , 2003, Chemical & pharmaceutical bulletin.

[17]  W. Pratt,et al.  Regulation of Signaling Protein Function and Trafficking by the hsp90/hsp70-Based Chaperone Machinery 1 , 2003, Experimental biology and medicine.

[18]  S. S. Rajan,et al.  Azadirachtol, a tetranortriterpenoid from neem kernels. , 2002, Acta crystallographica. Section C, Crystal structure communications.

[19]  P. Workman,et al.  Gene expression profiling of human colon cancer cells following inhibition of signal transduction by 17-allylamino-17-demethoxygeldanamycin, an inhibitor of the hsp90 molecular chaperone , 2000, Oncogene.

[20]  A. Jana,et al.  Anti-microbial activity of a new vaginal contraceptive NIM-76 from neem oil (Azadirachta indica). , 2000, Journal of ethnopharmacology.

[21]  Luo,et al.  Two novel azadirachtin derivatives from azadirachta indica , 1999, Journal of natural products.

[22]  R. P. Srivastava,et al.  Insecticidal meliacarpins (C-seco limonoids) from Melia azedarach , 1999 .

[23]  A. Ferreira,et al.  Meliacin butenolides from Trichilia estipulata , 1998 .

[24]  K. M. Madyastha,et al.  11-epi-azadirachtin D: an epimeric azadirachtin analogue from azadirachta indica , 1998 .

[25]  J. Coll,et al.  Tetranortriterpenoids from Azadirachta indica , 1997 .

[26]  S. Yakkundi,et al.  Limonoids from the seeds of Azadirachta indica , 1996 .

[27]  M. Bentley,et al.  Tetranortriterpenes from Melia volkensii. , 1988, Journal of natural products.

[28]  S. Faizi,et al.  Two new tetranortriterpenoids from Azadirachta indica , 1986 .

[29]  T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[30]  Y. Fukuyama,et al.  Bitter Limonoids from the Fruit of Melia azedarach L. var. japonica Makino , 1983 .

[31]  K. Koike,et al.  Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. Juss. (neem). , 2009, Journal of oleo science.

[32]  H. Shimada,et al.  New bioactive triterpenoids from Melia volkensii. , 1998, Journal of natural products.

[33]  H. Gutzeit,et al.  Tetranortriterpenoids related to nimbin and nimbolide from Azadirachta indica A. Juss (Meliaceae) , 1990 .