107439-70-3

Upstream product

• 470-17-7 isoalantolactone 
• 481-05-0 artemisin 
• 1750-99-8 6-epiartemisin 
• 171861-47-5 (S)-2-((2R,3S,4aS)-3-Hydroxy-4a,8-dimethyl-7-oxo-1,2,3,4,4a,7-hexahydro-naphthalen-2-yl)-propionic acid 
• 89362-29-8 3,3-ethanedithio-11α(H)-eudesm-4,5-dien-8,13-olide 
• 58976-58-2 3-oxo-11α(H)-eudesm-1,4-dien-8β,13-olide 
• 58976-59-3 3-oxo-7α,11α(H)-eudesm-4-en-8β,12-olide 
• 58511-25-4 7,8,11α,8βH-eudesm-4-en-12,8-olide 
• 91914-36-2 11α-phenylseleno-7,8αH-eudesm-4-en-12,8-olide 
• 113306-91-5 11α-bromo-7,8αH-eudesm-4-en-12,8-olide 
• 91914-35-1 methyl 8α-hydroxy-3-oxo-7αH,11βH-eudesma-1,4-dien-12-oate 
• 58964-73-1 methyl (11S)-3-oxo-8β-hydroxy-7αH-eudesma-1,4-dien-12-oate 
• 58964-75-3 methyl (11S)-3,8-dioxo-7αH-eudesma-1,4-dien-12-oate 

Downstream Products

• 6752-90-5 telekin 

Relevant academic research and scientific papers

TRANSFORMATION OF ARTEMISIN INTO YOMOGIN AND 1-DEOXYIVANGUSTIN

Partial syntheses of the sesquiterpene lactones yomogin and 1-deoxyivangustin from artemisin are disclosed.

Synthesis and Antiproliferative Activity of Conjugates of Anthracycline Antibiotics with Sesquiterpene Lactones of the Elecampane

The daunorubicin and doxorubicin anthracycline antibiotics were modified with the Inula helenium L. sesquiterpene lactones (alantolactone, isoalantolactone, and alloalantolactone) and with their epoxy derivatives. Antiproliferative properties of these conjugates were studied on tumor and normal cell lines. The daunorubicin conjugates with the sesquiterpene lactones (isoalantolactone, allantolactone, and alloalantolactone) and with their epoxy derivatives were found to exhibit the higher activity against human tumor cell lines than the corresponding doxorubicin conjugates. The daunorubicin conjugate with epoxyisoalantolactone proved to be the most effective compound, because it was more cytotoxic than daunorubicin towards a number of cell lines, including those daunorubicin-resistant, and did not affect normal human cells.

Isoalantolactone derivative promotes glucose utilization in skeletal muscle cells and increases energy expenditure in db/db mice via activating AMPK-dependent signaling

Augmenting glucose utilization and energy expenditure in skeletal muscle via AMP-activated protein kinase (AMPK) is an imperative mechanism for the management of type 2 diabetes. Chemical derivatives (2a-2h, 3, 4a-4d, 5) of the isoalantolactone (K007), a bioactive molecule from roots of Inula racemosa were synthesized to optimize the bioactivity profile to stimulate glucose utilization in skeletal muscle cells. Interestingly, 4a augmented glucose uptake, driven by enhanced translocation of glucose transporter 4 (GLUT4) to cell periphery in L6 rat skeletal muscle cells. The effect of 4a was independent to phosphatidylinositide-3-kinase (PI-3-K)/Akt pathway, but mediated through Liver kinase B1 (LKB1)/AMPK-dependent signaling, leading to activation of downstream targets acetyl coenzyme A carboxylase (ACC) and sterol regulatory element binding protein 1c (SREBP-1c). In db/db mice, 4a administration decreased blood glucose level and improved body mass index, lipid parameters and glucose tolerance associated with elevation of GLUT4 expression in skeletal muscle. Moreover, 4a increased energy expenditure via activating substrate utilization and upregulated the expression of thermogenic transcription factors and mitochondrial proteins in skeletal muscle, suggesting the regulation of energy balance. These findings suggest the potential implication of isoalantolactone derivatives for the management of diabetes.

Modification of alantolactones by natural alkaloids

Previously unknown compounds combining fragments of a sesquiterpene lactone and a natural alkaloid were synthesized. Derivatives of alantolactone were modified using a Michael reaction with alkaloids of various structural types.

Acidic isomerization of alantolactone derivatives

A series of derivatives of the natural sesquiterpene lactones alantolactone (1) and isoalantolactone (2) was prepared. The α-methylene-γ- lactone moiety was retained in the structures of these for further modifications using reactions that affected exclusively the nonconjugated double bonds of the decalin ring.

SYNTHESIS OF UMBELLIFOLIDE AND THREE NATURAL EUDESMAN-12,8-OLIDES FROM (-)-ARTEMISIN

The syntheses of the natural 4,5-secoeudesmanolide 1 (umbellifolide) and the eudesmanolides 2, 3 and 4 are described.The starting materials are synthetic eudesmane derivatives, the preparation of which from (-)-artemisin had been previously reported.