By Sherif S. Ebada, Neil Lajkiewicz (auth.), A. Douglas Kinghorn, Heinz Falk, Junichi Kobayashi (eds.)
The 3 reports conceal the advances within the chemistry and biology of withanolides during the last sixteen years, evaluate the chemistry and biology of the rocaglamide-type derivatives and similar compounds, with emphasis on their structural range, biosynthesis, pharmacological importance and overall synthesis, and summarize the large chemistry and biology reports on a ordinary product, that have led to a unique remedy authorized around the globe.
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Additional info for Progress in the Chemistry of Organic Natural Products Vol. 94
In the studies with S. littoralis, different rocaglamide derivatives were usually added at a range of concentrations to artificial diet, which was subsequently offered to newly hatched larvae in a no choice chronic feeding bioassay. S. Ebada et al. Fig. 11. Chemical structure of azadirachtin from Azadirachta indica (family Meliaceae) O O O COOCH3 OH O O H3COCO H3COOC O OH OH O the various rocaglamide congeners and compared to other insecticides of natural origin, such as azadirachtin from Azadirachta indica (family Meliaceae) (Fig.
G. the human acute T cell leukemia Jurkat, the human T cell lymphoma Hut78, the EBV-transformed human B lymphoblast SKW, and also primary tumor cells freshly isolated from patients having acute myeloid (AML), acute lymphoblastic (ALL), and chronic myeloid (CML) leukemias. Interestingly, rocaglamide (1) showed no or very low toxicities to normal peripheral blood T and B lymphocytes and had also very little toxicity to human bone marrow stem cells (100). Investigation of the molecular mechanisms by which rocaglamide (1) and 1-O-acetylrocaglamide (4) killed tumors but not normal cells revealed that these compounds preferentially induce apoptosis in malignant cells by differential modulation of the activities of ERK, p38, and JNK.
According to this hypothesis, the initial C-C-connecting step (step A) between C-2 of the flavonoid I and C-3 of the cinnamic acid amide II is a Michael-type 1,4-addition of the enolate subunit of I to the a,b-unsaturated amide II. The C-2 atom of the resulting amide enolate of III can now attack C-4 of the previous flavonoid, which has now become a strongly activated carbonyl group, to yield a five-membered ring, giving rise to IV (step B). According to this concept, IV constitutes the biosynthetic key intermediate and precursor both to aglain and rocaglamide derivatives.
Progress in the Chemistry of Organic Natural Products Vol. 94 by Sherif S. Ebada, Neil Lajkiewicz (auth.), A. Douglas Kinghorn, Heinz Falk, Junichi Kobayashi (eds.)