481-73-2Relevant articles and documents
A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain
Liang, Jing Lu,Cha, Hyo Chang,Lee, Seung Ho,Son, Jong-Keun,Chang, Hyeun Wook,Eom, Ji-Eun,Kwon, Youngjoo,Jahng, Yurngdong
, p. 447 - 454 (2012)
A new procedure for the preparation of emodin carbaldehyde and citreorosein was described, in which, ω,ω'-dibromomethylemodin triacetate was prepared as a key intermediate by NBSmediated bromination of 1,3,8-triacetylemodin. Reduction of emodin and citreorosein with SnCl 2 in a 1:1 mixture of HOAc and HCl afforded the corresponding anthrones in 90% and 92% yield, respectively, while the corresponding 10-desoxyemodin carbaldehyde was prepared by MnO2 oxidation of 10-desoxycitreorosein. 10-Desoxycitreorosein and emodin carbaldehyde showed feasible μ-calpain inhibitory activities with IC50 values of 20.15 and 25.77 M, respectively.
Chemoenzymatic, biomimetic total synthesis of (-)-rugulosin B, C and rugulin analogues and their biosynthetic implications
Mondal, Amit,Singh, Shailesh Kumar,Manna, Tanaya,Husain, Syed Masood
, p. 3337 - 3340 (2020/04/02)
Herein, we report the chemoenzymatic synthesis of a heterodimeric (-)-rugulosin B, homodimeric (-)-rugulosin C, and several rugulin analogues in three to four steps starting from anthraquinones. This work supports dimerization between variously substituted putative monomeric intermediates during the biosynthesis of naturally occurring (+)-rugulosin B and C.
Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis
Mondal, Amit,Saha, Nirmal,Rajput, Anshul,Singh, Shailesh Kumar,Roy, Brindaban,Husain, Syed Masood
, p. 8711 - 8715 (2019/10/16)
A chemoenzymatic reduction of citreorosein by the NADPH-dependent polyhydroxyanthracene reductase from Cochliobolus lunatus or MdpC from Aspergillus nidulans in the presence of Na2S2O4 gave access to putative biosynthetic intermediates, (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracene-1(2H)-one and its oxidized form, (R)-3,4-dihydrocitreorosein. Herein, we discuss the implications of these results towards the (bio)synthesis of aloe-emodin and (+)-rugulosin C in fungi.