Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies

Ju, Zixin; Sun, Jie; Liu, Yanping

doi:10.3390/molecules24213831

Cited by 46 publications

(33 citation statements)

References 24 publications

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“…Comparison of the main peaks in the Raman spectrum of the sample with the literature ones for indigotin (IND,[35]), indirubin (INR,[40]), 6-bromoindigotin (MBI,[36]) and 6,6'dibromoindigotin (DBI,[35]) together with their relative tentative assignations based on the literature.…”

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confidence: 99%

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Dyes from the Ashes: Discovering and Characterizing Natural Dyes from Mineralized Textiles

et al. 2020

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Vesuvius eruption that destroyed Pompeii in AD 79 represents one of the most important events in history. The cataclysm left behind an abundance of archeological evidence representing a fundamental source of the knowledge we have about ancient Roman material culture and technology. A great number of textiles have been preserved, rarely maintaining traces of their original color, since they are mainly in the mineralized and carbonized state. However, one outstanding textile sample displays a brilliant purple color and traces of gold strips. Since the purple was one of the most exclusive dyes in antiquity, its presence in an important commercial site like Pompeii induces us to deepen the knowledge of such artifacts and provide further information on their history. For this reason, the characterization of the purple color was the main scope of this research, and to deepen the knowledge of such artifacts, the SERS (Surface Enhanced Raman Scattering) in solution approach was applied. Then, these data were enriched by HPLC-HRMS analyses, which confirmed SERS-based hypotheses and also allowed to hypothesize the species of the origin mollusk. In this context, a step-by-step integrated approach resulted fundamental to maximize the information content and to provide new data on textile manufacturing and trade in antiquity.

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confidence: 99%

“…excitation laser line: 633 nm); (f) indigotin (ref [35],. excitation laser line: 633 nm); (g) indirubin (ref [40],. excitation laser line: 532 nm).…”

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Dyes from the Ashes: Discovering and Characterizing Natural Dyes from Mineralized Textiles

et al. 2020

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“…The peak between 1000 and 1100 cm − 1 indicates C-O in C-OH (Oliveira et al 2016). The peak between 1700 and 1800 cm − 1 indicates C-O in benzene-OH, the peak between 1600 and 1650 cm − 1 indicates C-C in benzene, the peak between 1550 and 1800 cm − 1 indicates C = O in benzene = O and N-H in pyrrole, the peak between 1350 and 1550 cm − 1 indicates C-H and C-C and C-O in the side chain which bound to benzene (Toledo et al 2012;Ju et al 2019). Comparing these differences in peak intensity of four parts, a low peak of hydroxyl groups bonded to the benzene ring, i.e.…”

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confidence: 99%

Evaluation of Antioxidant Extraction by Microwave Treatment from Japanese Indigo Plant

Suzuki¹,

Nakamura²,

Asada³

2021

Preprint

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Tadeai (Awa-ai) is an indigo plant that is produced in large quantities in Tokushima prefecture, Japan. The leaves of Tadeai are used for dyeing (Ai-zome), but there is no use for the other parts, i.e. flowers, stems, leaves, and roots, most of which are discarded. In this study, we search for new ways to use Tadeai including parts other than the leaves and examined the antioxidant activity of water soluble extract from Tadeai. To extract antioxidants efficiently, processing was undertaken using a microwave irradiation device. The evaluation of Tadeai extract and its antioxidant activity was performed by measuring the amount of phenolic compounds by the Folin–Ciocalteu method and the DPPH radical scavenging activity test. Compared to the sample that was not subjected to microwave treatment, the amount of phenolic compounds was observed to be double, and the antioxidant activity eight times higher. The microwave treatment conditions that showed the best results are 200 ℃ and 1 min, and the evaluation indicated that the part that exhibits the best results is the root. Furthermore, the differences among Tadeai varieties were also examined. The best result was for the “Kojoko Akahana;” the root of the “Kojoko Akahana” exhibited the highest antioxidant effect. Its amount of phenolic compounds and EC50 value were 44.1 mg-catechin equiv./g-dry sample and 0.018 g/L, respectively. In this study, it was shown that the antioxidant activity of the parts other than the leaves is high, so it is expected that Tadeai waste will be effectively utilized as a raw material for producing antioxidants in the future.

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“…Indirubin, a component of indigo naturalis, which is derived from the leaves and stems of indigo plants, is used in traditional Chinese medicine to treat inflammatory bowel disease [ 52 ]. A study of the molecular structure of indirubin indicates that it has a more three-dimensional structure compared to the more planar structure of the indigo molecule which is another component of indigo naturalis [ 53 ]. Indirubin is also a potent cyclin-dependent kinase inhibitor which is neuroprotective, attenuates high fat-high fructose induced Aβ-aggregation, and prevents tau-phosphorylation in Alzheimer’s disease animal models [ 54 , 55 , 56 , 57 , 58 , 59 , 60 ].…”

Section: Discussionmentioning

confidence: 99%

Functions of Small Organic Compounds that Mimic the HNK-1 Glycan

Wang

Theis

Kabat

et al. 2020

IJMS

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Because of the importance of the HNK-1 carbohydrate for preferential motor reinnervation after injury of the femoral nerve in mammals, we screened NIH Clinical Collection 1 and 2 Libraries and a Natural Product library comprising small organic compounds for identification of pharmacologically useful reagents. The reason for this attempt was to obviate the difficult chemical synthesis of the HNK-1 carbohydrate and its isolation from natural sources, with the hope to render such compounds clinically useful. We identified six compounds that enhanced neurite outgrowth from cultured spinal motor neurons at nM concentrations and increased their neurite diameter, but not their neurite branch points. Axons of dorsal root ganglion neurons did not respond to these compounds, a feature that is in agreement with their biological role after injury. We refer to the positive functions of some of these compounds in animal models of injury and delineate the intracellular signaling responses elicited by application of compounds to cultured murine central nervous system neurons. Altogether, these results point to the potential of the HNK-1 carbohydrate mimetics in clinically-oriented settings.

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Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies

Cited by 46 publications

References 24 publications

Dyes from the Ashes: Discovering and Characterizing Natural Dyes from Mineralized Textiles

Dyes from the Ashes: Discovering and Characterizing Natural Dyes from Mineralized Textiles

Evaluation of Antioxidant Extraction by Microwave Treatment from Japanese Indigo Plant

Functions of Small Organic Compounds that Mimic the HNK-1 Glycan

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