Indirubin

Yoshikawa M, Murakami T, Kishi A, et al. Novel indole S,0-bisdesmoside, calantho-side, the precursor glycoside of tryptanthrin, indirubin, and isatin, with increasing skin blood flow promoting effects, from two Calanthe species (Orchidaceae). Chem Pharm Bull (Tokyo) 1998 46 886-888. 

Indigotin Indirubin Monobromoindigotin Dibromoindigotin Dibromoindirubin Other compounds... 

Indigo is considered as one of the most important dyes. Its preparations are usually analysed by HPLC with UV-Vis [46,60] or APCI MS detection. [61,62] Separation of the colouring components of indigo extracted with DMSO is usually performed with the use of a Cl 8 column. Spectrophotometric detection of blue indigotin is performed at 617 nm, red indirubin at 540 nm, and brown isoindigo at 365 and 490 nm. As mobile phases, mixtures of methanol or acetonitrile and water with the addition of TFA or formic acid are used to ensure compatibility with the requirements of the APCI source. 

Indigoid species are also present in another dyestuff, Tyrian Purple, extracted from molluscs from the Muricidae family. It owes its specific red shade to the presence of bromoindigoids. In the extract of the dyestuff, after chromatographic separation of its components,[44] in addition to indigotin, indirubin and isoindigo, 6,6 -dibromoindigotin is... 

Figure 13.8 Structures and ESI mass spectra of (a) indirubin and (b) indigotin. Reproduced from /VI. Puchalska, K. Potec Pawlak, I. Zadrozna, H. Hryszko and M. Jarosz. J. Mass Spectrom., 39, 1441 1449 (2004). By permission of John Wiley Sons, Ltd...

Silk and wool fibres of Coptic textiles from fourth to twelfth century Carminic acid, laccaic acids A, B, C and E, xantholaccaic acid A, purpurin, xanthopurpurin, alizarin, monochloroalizarin, dichloroalizarin, ellagic acid, luteolin, apigenin, rhamnetin, indirubin HCI/EtOH, pyridine A ACN B H20 with TFA 278, 350 nm/ESI (+)... 

Scheme II - Plausible sequence of formation of indirubin from indoxyl ans isatin...

Fig. 2.40. Plausible sequence of formation of indigotin from indican (I), of indirubin from indoxyl and isatin (II), and of tryptanthrin from anthranillic acid and isatin (III). Reprinted with permission from A. V. Muruganandam et al. [118].

Leclerc, S., Garnier, M., Hoessel, R. (2001) et al. Indirubins inhibit glycogen synthase kinase-3 3 and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer s disease. A property common to most cyclin-dependent kinase inhibitors. J. Biol. Chem., 276, 251-260. 

An oxime derivative of indirubin (a natural bis-indole alkaloid used in traditional Chinese medicine to treat chronic myelocytic leukemia), indirubin-3 -monoxime (37), was found to be a potent inhibitor of cyclin-dependent kinases (CDKs), and of the proliferation of myeloid leukemia cells via inhibition of a tyrosine kinase . The 3D structure of the complex of 37 with CDK revealed that the oxime function is intact, and that it occupies the ATP-ribose site of the CDK-ATP structure. While the specific role of the oxime group in the biological activity of 37 is not clear, it was proposed that its reactivity may be utilized for further drug design... 

Baphicanthus cusia (Nees.) Bremek. Ban Lan or Da Qing Ye (leaf, root) Indirubin, indigo, indo-brown, indo-yellow, isoindigo, lacerol, tryptanthrin.53 Antidotal, febrifugal, treat fever, epidemic mumps, erysipelas, rashes, sore throat. 

The following exemplify reactions of the aldol type. 3-Hydroxythiophene with benzaldehyde forms (269). Anions derived from oxindole (270 Z = NH) and indoxyl (271) react with isatin (272) to give isoindigo (273) and indirubin (274). 

Lithium aluminum hydride reduction of isatin gave mixtures of 3-hydroxyindolinc, indole, indigo, and indirubin with compositions depending upon the experimental conditions.246 The latter three products... 

Oxidation of indoles by hydrogen peroxide under weakly acidic conditions (72HC(25-l)l) yields 2,2-di(3-indolyl)indolin-3-one (160), indigo (161) and, to a lesser extent, indirubin. All of the products are derived from the initial formation of indolin-3-one by a mechanism... 

The symmetrical thioindigo dyes have the structure (355), where R = Cl, Br, Me, NH2, OMe, OEt or SEt located at the 4-, 5-, 6- or 7-position of the benzo[6 jthiophene parent compound, or combinations of two or three of these substituents. The original Friedlander synthesis involved mild oxidation of a 3-hydroxybenzo[6 jthiophene, but numerous methods, many patented, have been used. The 2,3 -bithioindigos, also known as thioindirubins (356), by analogy with the indigo isomer, indirubin, are also dyes of some interest. 

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