Revisiting Curcumin Chemistry- Part II: Synthesis of Monomethylcurcumin and Isomeric Demethoxycurcumins and their Characterization

Rao, E. Venkata; Prasad, Y. Rajendra; Sudheer, Preethi

doi:10.4172/pharmaceutical-sciences.1000296

Cited by 5 publications

(5 citation statements)

References 8 publications

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“…In addition to the extraction and isolation of curcuminoids from turmeric, chemical synthesis is a strategy for obtaining curcuminoids [ 26 , 27 ]. The earliest record of chemical synthesis of curcumin was in 1913 [ 28 ]; since then, many studies have explored preparation methods of curcumin by chemical synthesis [ 26 , 29 , 30 ]. Unlike curcumin extracted from turmeric, which often contains a variety of curcuminoids, chemical synthesis can prepare specific, high-purity curcuminoids by adjusting conditions and precursors.…”

Section: Composition Of Turmericmentioning

confidence: 99%

The therapeutic potential of curcumin and its related substances in turmeric: From raw material selection to application strategies

Hsu¹,

Ho²,

Pan³

2023

Journal of Food and Drug Analysis

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Turmeric ( Curcuma longa L.) is a medicinal plant used extensively in Chinese and Indian traditional medicine as a home remedy for various diseases. It has been used for medical purposes for centuries. Today, turmeric has become one of the most popular medicinal herbs, spices, and functional supplements worldwide. Curcuminoids are linear diary-lheptanoids from the rhizomes that include curcumin and two related compounds: demethoxycurcumin and bisdemethoxycurcumin, which are the active components of the C. longa plant, play a crucial role in numerous functions. This review summarises the composition of turmeric and the properties of curcumin regarding its antioxidant, anti-inflammatory, anti-diabetic, anti-colorectal cancer, and other physiological activity. In addition, the dilemma of the application of curcumin due to its low water solubility and bioavailability was discussed. Finally, this article provides three novel application strategies based on previous studies: using curcumin analogues and related substances, gut microbiota regulation, and using curcumin-loaded exosome vesicles and turmeric-derived exosome-like vesicles to overcome application limitations.

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Section: Composition Of Turmericmentioning

confidence: 99%

The therapeutic potential of curcumin and its related substances in turmeric: From raw material selection to application strategies

Hsu¹,

Ho²,

Pan³

2023

Journal of Food and Drug Analysis

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“…Later, Pabon described a simple method for the synthesis of curcumin with high yields that is still in use today [5]. Patented processes indicating the use of B 2 O 3 , trialkylborate, and n-butylamine along with inert organic amide solvents have since improved yields [6][7][8] (Figure 2(a)). Highperformance liquid chromatography (HPLC) is efficiently used for the detection and quantification of curcumin [9].…”

Section: The Structural Chemistry Of Curcumin Related To Its Biologicmentioning

confidence: 99%

Curcumin, a Multifaceted Hormetic Agent, Mediates an Intricate Crosstalk between Mitochondrial Turnover, Autophagy, and Apoptosis

Rainey

Moustapha

Petit

2020

Oxidative Medicine and Cellular Longevity

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Curcumin has extensive therapeutic potential because of its antioxidant, anti-inflammatory, and antiproliferative properties. Multiple preclinical studies in vitro and in vivo have proven curcumin to be effective against various cancers. These potent effects are driven by curcumin’s ability to induce G2/M cell cycle arrest, induce autophagy, activate apoptosis, disrupt molecular signaling, inhibit invasion and metastasis, and increase the efficacy of current chemotherapeutics. Here, we focus on the hormetic behavior of curcumin. Frequently, low doses of natural chemical products activate an adaptive stress response, whereas high doses activate acute responses like autophagy and cell death. This phenomenon is often referred to as hormesis. Curcumin causes cell death and primarily initiates an autophagic step (mitophagy). At higher doses, cells undergo mitochondrial destabilization due to calcium release from the endoplasmic reticulum, and die. Herein, we address the complex crosstalk that involves mitochondrial biogenesis, mitochondrial destabilization accompanied by mitophagy, and cell death.

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“…8 Chemical synthesis of curcumin involves multiple high-cost steps and the use of toxic chemicals, such as acetylacetone difluoroboronite, aromatic aldehyde, and n-butylamine. 9 However, the biosynthesis of curcumin by microbial fermentation is a potential way to obtain large quantities of curcumin with high purity and without the use of toxic chemicals.…”

Section: Introductionmentioning

confidence: 99%

“…Curcumin has health-beneficial biological activities, such as antioxidant, anti-inflammatory, anticancer, and antidiabetes. , The main source of curcumin is extracted from the turmeric plant rhizome, but this is time-consuming, wasteful of land resources, seasonal, and subject to disruption by bad weather . Chemical synthesis of curcumin involves multiple high-cost steps and the use of toxic chemicals, such as acetylacetone difluoroboronite, aromatic aldehyde, and n -butylamine . However, the biosynthesis of curcumin by microbial fermentation is a potential way to obtain large quantities of curcumin with high purity and without the use of toxic chemicals.…”

Section: Introductionmentioning

confidence: 99%

Efficient De Novo Biosynthesis of Curcumin in Escherichia coli by Optimizing Pathway Modules and Increasing the Malonyl-CoA Supply

Chen,

Wang,

Wang

et al. 2023

J. Agric. Food Chem.

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Curcumin is a natural phenylpropanoid compound with various biological activities and is widely used in food and pharmaceuticals. A de novo curcumin biosynthetic pathway was constructed in Escherichia coli BL21(DE3). Optimization of the curcumin biosynthesis module achieved a curcumin titer of 26.8 ± 0.6 mg/L. Regulating the metabolic fluxes of the β-oxidation pathway and fatty acid elongation cycle and blocking the endogenous malonyl-CoA consumption pathway increased the titer to 113.6 ± 7.1 mg/L. Knockout of endogenous curcumin reductase (curA) and intermediate product detoxification by heterologous expression of the solvent-resistant pump (srpB) increased the titer to 137.5 ± 3.0 mg/L. A 5 L pilot-scale fermentation, using a threestage pH alternation strategy, increased the titer to 696.2 ± 20.9 mg/L, 178.5-fold higher than the highest curcumin titer from de novo biosynthesis previously reported, thereby laying the foundation for efficient biosynthesis of curcumin and its derivatives.

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Revisiting Curcumin Chemistry- Part II: Synthesis of Monomethylcurcumin and Isomeric Demethoxycurcumins and their Characterization

Cited by 5 publications

References 8 publications

The therapeutic potential of curcumin and its related substances in turmeric: From raw material selection to application strategies

The therapeutic potential of curcumin and its related substances in turmeric: From raw material selection to application strategies

Curcumin, a Multifaceted Hormetic Agent, Mediates an Intricate Crosstalk between Mitochondrial Turnover, Autophagy, and Apoptosis

Efficient De Novo Biosynthesis of Curcumin in Escherichia coli by Optimizing Pathway Modules and Increasing the Malonyl-CoA Supply

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