Indole alkaloids indigodoles A–C from aerial parts of Strobilanthes cusia in the traditional Chinese medicine Qing Dai have anti-IL-17 properties

Lee, Chia-Lin; Wang, Chen; Hu, Hao-Chun; Yen, Hung-Rong; Song, Ying-Chyi; Yu, Shyr-Shen; Chen, Chao‐Jung; Li, Wei-Chu; Wu, Yang Chang

doi:10.1016/j.phytochem.2019.02.016

Cited by 50 publications

(35 citation statements)

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“…Notably, tryptanthrin and indigodole B were originally identified as the compounds in the S. cusia leaf methanol extract with highest activity against HCoV-NL63 (Figures 3-5, Table 1). Indigodole B, recently identified in S. cusia leaf methanol extract [9], is a tryptanthrin derivative conjugated with the ethyl group at C-5a (5aR-ethyltryptanthrin), and exhibited intense antiviral activity with an IC50 of 2.60 μM against virus yield (Figure 4). Indigodole B, recently identified in S. cusia leaf methanol extract [9], is a tryptanthrin derivative conjugated with the ethyl group at C-5a (5aR-ethyltryptanthrin), and exhibited intense antiviral activity with an IC50 of 2.60 μM against virus yield (Figure 4).…”

Section: Discussionmentioning

confidence: 99%

“…BR0308980) was purchased and further credited at the Chinese Medicine Research and Development Center, China Medical University Hospital, Taiwan, as described in a previous report [9]. The powder of S. cusia leaf (Lot.…”

Section: Preparation Of S Cusia Leaf Methanol Extract and Its Relatementioning

confidence: 99%

“…The chemical components of the S. cusia leaf methanol extract included β-sitosterol, indirubin, tryptanthrin, betulin, indigodole A, and indigodole B, as described in our prior report [9]. These chemical components (at 40 μM concentration) were studied for the antiviral activity exhibited against HCoV-NL63 using the CPE reduction assay (Figure 3).…”

Section: Action Of Active Components From S Cusia Leaf Extract Againmentioning

confidence: 99%

“…The S. cusia leaf (called "Da-Ching-Yeh" in Chinese) is generally used for the production of indigo dyes (Indigo Natruralis, named "Qing Dai" in Chinese), displaying antibacterial, anti-inflammatory, and antipyretic properties [7,8]. S. cusia leaves contain effective chemical components with antibacterial, anti-inflammatory and antitumor activities, including βsitosterol, indirubin, tryptanthrin (6,12-dihydro-6,12-dioxoindolo-(2,1-b)-quinazoline), betulin, indigodole A, indigodole B (5aR-ethyltryptanthrin), strobilanthosides A-C, and phenylethanoidglycosides [9,10]. Notably, indirubin and its derivatives modulate influenza A virusinduced inflammation and have been suggested as antiviral and immunomodulatory agents against influenza A virus infection [3,[11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

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Antiviral Action of Tryptanthrin Isolated from Strobilanthes cusia Leaf against Human Coronavirus NL63

et al. 2020

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Strobilanthes cusia (Nees) Kuntze is a Chinese herbal medicine used in the treatment of respiratory virus infections. The methanol extract of S. cusia leaf contains chemical components such as β-sitosterol, indirubin, tryptanthrin, betulin, indigodole A, and indigodole B that have diverse biological activities. However, the antiviral action of S. cusia leaf and its components against human coronavirus remains to be elucidated. Human coronavirus NL63 infection is frequent among immunocompromised individuals, young children, and in the elderly. This study investigated the anti-Human coronavirus NL63 (HCoV-NL63) activity of the methanol extract of S. cusia leaf and its major components. The methanol extract of S. cusia leaf effectively inhibited the cytopathic effect (CPE) and virus yield (IC50 = 0.64 μg/mL) in HCoV-NL63-infected cells. Moreover, this extract potently inhibited the HCoV-NL63 infection in a concentration-dependent manner. Among the six components identified in the methanol extract of S. cusia leaf, tryptanthrin and indigodole B (5aRethyltryptanthrin) exhibited potent antiviral activity in reducing the CPE and progeny virus production. The IC50 values against virus yield were 1.52 μM and 2.60 μM for tryptanthrin and indigodole B, respectively. Different modes of time-of-addition/removal assay indicated that tryptanthrin prevented the early and late stages of HCoV-NL63 replication, particularly by blocking viral RNA genome synthesis and papain-like protease 2 activity. Notably, tryptanthrin (IC50 = 0.06 μM) and indigodole B (IC50 = 2.09 μM) exhibited strong virucidal activity as well. This study identified tryptanthrin as the key active component of S. cusia leaf methanol extract that acted against HCoV-NL63 in a cell-type independent manner. The results specify that tryptanthrin possesses antiviral potential against HCoV-NL63 infection.

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Section: Discussionmentioning

confidence: 99%

Section: Preparation Of S Cusia Leaf Methanol Extract and Its Relatementioning

confidence: 99%

Section: Action Of Active Components From S Cusia Leaf Extract Againmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antiviral Action of Tryptanthrin Isolated from Strobilanthes cusia Leaf against Human Coronavirus NL63

et al. 2020

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“…Qing Dai, a famous traditional Chinese medicine (TCM), is the pale blue to grayish-blue dried powder prepared by a traditional fermentation process (Lee et al, 2019;Lin, 2016;Pan et al, 2018). Currently, this TCM could treat various clinical inflammatory diseases, such as ulcerative colitis and psoriasis (Naganuma, 2019;Sugimoto et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

IL-17A inhibitions of indole alkaloids from traditional Chinese medicine Qing Dai

Lee

Wang

Kuo

et al. 2020

Journal of Ethnopharmacology

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A B S T R A C TEthnopharmacological relevance: Qing Dai, a famous traditional Chinese medicine (TCM), is prepared by a traditional fermentation process with the aerial part of Strobilanthes cusia. Currently, this TCM could treat various clinical inflammatory diseases, such as ulcerative colitis and psoriasis, however, the bioactive components of Qing Dai are unknown clearly. Aim of the study: To isolate and identify the anti-IL-17A components of Qing Dai. Materials and methods: Silica, RP-18 gels, and size exclusion resin were used for column chromatography to isolate the pure compounds. The structures of isolates were elucidated by NMR, MS, UV, IR spectra, and optical rotation. IL-17A protein and gene expressions were also evaluated in the Th17 cell model and luciferase reporter assay, respectively. Results: Two indole alkaloids, including one new indigodole D and cephalandole B, were isolated from Qing Dai. Indigodole D could inhibit IL-17A protein production during the Th17 polarization (EC 50 : 2.16 μg/mL) or after the polarization (EC 50 : 5.99 μg/mL) without cytotoxicity toward Th17 cells. Cephalandole B did not inhibit the IL-17A protein secretion. Nevertheless, both isolates notably inhibited IL-17A gene expression, especially cephalandole B, in a dose-dependent manner in Jukat cells with IL-17A luciferase reporter. Conclusions: Indole alkaloids, indigodoles A, C, D, tryptanthrin, and indirubin could contribute to anti-IL 17A properties of Qing Dai. The possible biogenetic mechanisms of above-mentioned indoles were also speculated in this investigation for further promising anti-IL-17 lead drugs development.

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Specific Secondary Metabolites of Medicinal Plants and Their Role in Stress Adaptation

Sytar,

Hajihashemi

2024

Plant Secondary Metabolites and Abiotic Stress

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Indole alkaloids indigodoles A–C from aerial parts of Strobilanthes cusia in the traditional Chinese medicine Qing Dai have anti-IL-17 properties

Cited by 50 publications

References 18 publications

Antiviral Action of Tryptanthrin Isolated from Strobilanthes cusia Leaf against Human Coronavirus NL63

Antiviral Action of Tryptanthrin Isolated from Strobilanthes cusia Leaf against Human Coronavirus NL63

IL-17A inhibitions of indole alkaloids from traditional Chinese medicine Qing Dai

Specific Secondary Metabolites of Medicinal Plants and Their Role in Stress Adaptation

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