Pharmacological and analytical aspects of alkannin/shikonin and their derivatives: An update from 2008 to 2022

Kaur, Kirandeep; Sharma, Ridhima; Singh, Atamjit; Attri, Shivani; Arora, Saroj; Kaur, Sarabjit; Bedi, Neena

doi:10.1016/j.chmed.2022.08.001

Cited by 20 publications

(11 citation statements)

References 123 publications

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“…Among these compounds, deoxy-shikonin had the highest peak area percentage and was already isolated from different plants of the Borignaceae family. This compound exhibited antibacterial, antifungal, wound healing, and antitumor properties 84 but its underlying mechanism in inflammation-induced HCC was still unclear. Thymol is a phenol with antibacterial, anti-inflammatory, anti-mutagenic and radioprotective properties 85 .…”

Section: Discussionmentioning

confidence: 99%

Phytochemical profiling and cytotoxic potential of Arnebia nobilis root extracts against hepatocellular carcinoma using in-vitro and in-silico approaches

Kiran

Altaf

Sarwar

et al. 2023

Sci Rep

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Hepatocellular carcinoma is the fifth most prevalent cancer worldwide. The emergence of drug resistance and other adverse effects in available anticancer options are challenging to explore natural sources. The current study was designed to decipher the Arnebia nobilis (A. nobilis) extracts for detecting phytochemicals, in-vitro evaluation of antioxidative and cytotoxic potentials, and in-silico prediction of potent anticancer compounds. The phytochemical analysis revealed the presence of flavonoids, phenols, tannins, alkaloids, quinones, and cardiac glycosides, in the ethanol (ANE) and n-hexane (ANH) extracts of A. nobilis. ANH extract exhibited a better antioxidant potential to scavenge DPPH, nitric oxide and superoxide anion radicals than ANE extract, which showed better potential only against H2O2 radicals. In 24 h treatment, ANH extract revealed higher cytotoxicity (IC50 value: 22.77 µg/mL) than ANH extract (IC50 value: 46.74 µg/mL) on cancer (HepG2) cells without intoxicating the normal (BHK) cells using MTT assay. A better apoptotic potential was observed in ANH extract (49.10%) compared to ANE extract (41.35%) on HepG2 cells using the annexin V/PI method. GCMS analysis of ANH extract identified 35 phytocompounds, from which only 14 bioactive compounds were selected for molecular docking based on druggability criteria and toxicity filters. Among the five top scorers, deoxyshikonin exhibited the best binding affinities of − 7.2, − 9.2, − 7.2 and − 9.2 kcal/mol against TNF-α, TGF-βR1, Bcl-2 and iNOS, respectively, followed by ethyl cholate and 2-Methyl-6-(4-methylphenyl)hept-2-en-4-one along with their desirable ADMET properties. The phytochemicals of ANH extract could be used as a promising drug candidate for liver cancer after further validations.

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Section: Discussionmentioning

confidence: 99%

Phytochemical profiling and cytotoxic potential of Arnebia nobilis root extracts against hepatocellular carcinoma using in-vitro and in-silico approaches

Kiran

Altaf

Sarwar

et al. 2023

Sci Rep

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“…Candida albicans is an opportunistic pathogen capable of causing fungal infections in humans. Interestingly, sikonin could inhibit the growth of Candida albicans through increasing the intracellular reactive oxygen species (ROS) [11,12] . Catalase‐peroxidase (KatG) of Mtb can efficiently degrade intracellular hydrogen peroxide, thus reducing the level of ROS in Mtb cells.…”

Section: Methodsmentioning

confidence: 99%

“…Based on the antibacterial activity of the ethyl acetate partition, it (24 g) was further subjected to silica gel H column chromatography eluting with hexane containing increasing amounts of ethyl acetate to afford 19 major fractions (Fr. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Among the nineteen fractions, Fr.…”

Section: Bioassay-guided Isolation Of Extract Of C Lanceolatummentioning

confidence: 99%

“…Interestingly, sikonin could inhibit the growth of Candida albicans through increasing the intracellular reactive oxygen species (ROS). [11,12] Cata-lase-peroxidase (KatG) of Mtb can efficiently degrade intracellular hydrogen peroxide, thus reducing the level of ROS in Mtb cells. We speculate that sikonin may lead to the accumulation of ROS in Mtb cells through the inhibition of KatG.…”

Section: Molecular Dockingmentioning

confidence: 99%

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Antimycobacterial Compound of Cynoglossum lanceolatum Forsk.: Bioassay Guided Isolation, Molecular Docking, Synthesis of Analogs, and a Plausible Mechanism of Action

Yang

Xin

Wang

et al. 2023

Chemistry & Biodiversity

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Tuberculosis (TB) remains a major threat to human health. Due to the prevalence of drug‐resistant Mycobacterium tuberculosis (Mtb), it is urgent to discover drugs with new mechanisms of action (MOA) to ensure effectiveness against strains that are resistant to existing TB drugs. Cynoglossum lanceolatum Forsk was used to treat TB in Traditional Chinese Medicine. In this article, shikonin, the anti‐Mtb active component, was obtained from the whole herb extract of C. lanceolatum by bioassay‐guided isolation. Using the microplate alamar blue assay (MABA), the minimum inhibitory concentration (MIC) of shikonin against Mtb was determined to be 128 μg/mL. In order to obtain a more efficient anti‐Mtb molecule, (E)‐1‐(6‐bromo‐2,3‐dihydrochromen‐4‐ylidene)thiosemicarbazide was synthesized based on the scaffold of shikonin, which exhibited potent activity against Mtb (MIC=4 μg/mL). These results highlight that both naphthalene‐1,4‐dione and chroman‐4‐one are pharmacophores with activities against Mtb. To investigate a plausible mechanism of action, the molecular docking was firstly performed against catalase‐peroxidase enzyme (KatG) of Mtb using AutoDock 4 software. The results demonstrated that both shikonin and (E)‐1‐(6‐bromo‐2,3‐dihydrochromen‐4‐ylidene)thiosemicarbazide could bind to the active site of Mtb KatG. KatG enzyme activity and intracellular reactive oxygen species (ROS) levels in Mtb cells were then measured by ultraviolet spectrophotometric method and fluorescence microplate reader assay, respectively. The experiments confirmed that above compounds could inhibit the catalytic activity of Mtb KatG, and cause the ROS accumulation in Mtb cells. Therefore, inhibition of KatG may be a novel mechanism of action for these two compounds to fight against Mtb.

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“…Lithospermum erythrorhizon ( L. erythrorhizon ), also known as “Zicao,” is a traditional Chinese medicine with a long history to treat infections, inflammation, and hemorrhagic diseases ( Shu et al, 2022 ). Shikonin (SKN), a naphthoquinone compound, is one of the main active components isolated from L. erythrorhizon ( Kaur et al, 2022a ). SKN showed the ability to reverse the drug resistance of MRSA and its clinical strains, and interfere with the formation of S. aureus biofilms ( Li et al, 2022a ).…”

Section: Introductionmentioning

confidence: 99%

PLA-HPG based coating enhanced anti-biofilm and wound healing of Shikonin in MRSA-infected burn wound

Han

Chen

Liang

et al. 2023

Front. Bioeng. Biotechnol.

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Burn wounds are susceptible to bacterial infections, including Methicillin-resistant Staphylococcus aureus (MRSA), which typically form biofilms and exhibit drug resistance. They also have specific feature of abundant exudate, necessitating frequent drug administration. Shikonin (SKN) has been reported to reverse MRSA drug resistance and possesses anti-biofilm and wound healing properties, however, it suffers from drawbacks of low solubility and instability. In this study, we developed PLA-HPG based bioadhesive nanoparticles SKN/BNP, which demonstrated a drug loading capacity of about 3.6%, and exhibited sustained-release behavior of SKN. The aldehyde groups present on the surface of BNP improved the local adhesion of SKN/BNP both in vitro and in vivo, thereby reducing the frequency of drug dosing in exudate-rich burn wounds. BNP alone enhanced proliferation and migration of the fibroblast, while SKN/BNP promoted fibroblast proliferation and migration as well as angiogenesis. Due to its bioadhesive property, BNP directly interacted with biofilm and enhanced the efficacy of SKN against MRSA biofilm in vitro. In a mouse model of MRSA-infected burn wounds, SKN/BNP demonstrated improved anti-biofilm and wound healing efficiency. Overall, our findings suggest that SKN/BNP holds great promise as a novel and effective treatment option for clinical applications in MRSA-infected burn wounds.

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Pharmacological and analytical aspects of alkannin/shikonin and their derivatives: An update from 2008 to 2022

Cited by 20 publications

References 123 publications

Phytochemical profiling and cytotoxic potential of Arnebia nobilis root extracts against hepatocellular carcinoma using in-vitro and in-silico approaches

Phytochemical profiling and cytotoxic potential of Arnebia nobilis root extracts against hepatocellular carcinoma using in-vitro and in-silico approaches

Antimycobacterial Compound of Cynoglossum lanceolatum Forsk.: Bioassay Guided Isolation, Molecular Docking, Synthesis of Analogs, and a Plausible Mechanism of Action

PLA-HPG based coating enhanced anti-biofilm and wound healing of Shikonin in MRSA-infected burn wound

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