Indole Alkaloid Glycosides from the Aerial Parts of <i>Strobilanthes cusia</i>

Gu, Wei; Zhang, Yu; Hao, Xiao Jiang; Yang, Fu Mei; Sun, Qian; Morris‐Natschke, Susan L.; Lee, Kuo‐Hsiung; Wang, Yue-Hu; Long, Chunlin

doi:10.1021/np5003274

Cited by 100 publications

(41 citation statements)

References 15 publications

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“…Compounds 111-114 from F. suspensa with neuroprotective effects are four unusual adducts of a flavonoid unit fused to a phenylethanoid glycoside through a pyran ring or carbon-carbon bond [20]. Compounds 115 and 116 from Strobilanthes cusia are adducts of an indole alkaloid group fused to a phenylethanoid glycoside [52]. …”

Section: Introductionmentioning

confidence: 99%

Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics

2016

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Phenylethanoid glycosides (PhGs) are widely distributed in traditional Chinese medicines as well as in other medicinal plants, and they were characterized by a phenethyl alcohol (C 6 -C 2 ) moiety attached to a β-glucopyranose/β-allopyranose via a glycosidic bond. The outstanding activity of PhGs in diverse diseases proves their importance in medicinal chemistry research. This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, including neuroprotective, anti-inflammatory, antioxidant, antibacterial and antivirus, cytotoxic, immunomodulatory, and enzyme inhibitory effects, and pharmacokinetic properties.

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Section: Introductionmentioning

confidence: 99%

Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics

2016

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“…In 2016, Xu's group replaced oxygen in 2-benzylidene-1benzofuran-3-ones with NAc (27) and reacted it with 20 under catalysis with Cat-6 to obtain indole [5,5] spirocycles (Scheme 4). [19] In this reaction, the hydroxy group in substrate 20 is crucial for the whole catalytic system.…”

Section: Synthesis Of Spiro Compounds From 2-benzylidene-1-benzofuranmentioning

confidence: 99%

“…The core structures of benzothiophene, benzofuran, indole and indene are found in many natural products and pharmaceuticals, which are studied in materials science. [1] Examples include Raloxifene, [2] AP521, [3] MJ-III-65, [4] and Strobilanthoside [5] (Figure 1). The construction of benzothiophene, benzofuran, indole, and indene derivatives is a significant challenge in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Deng

Meng

2020

Chemistry An Asian Journal

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Benzothiophene, benzofuran, indole, and indene derivatives are privileged heterocyclic motifs. These are present in a wide range of bioactive natural products and pharmaceutical drugs and are the subject of materials science research. However, the construction of benzothiophene, benzofuran, indole, and indene frameworks have been long‐standing challenges to organic chemists. In this review, we classify the derivatives of four structures synthesized from 2‐benzylidene‐1‐benzofuran‐3‐one and their analogues in terms of their ring size (from three‐ to ten‐membered) and type (fused or spiro), as well as summarizing the developments of this field. Finally, we discuss the ring opening and 1,4‐addition reactions.

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“…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]. β-sitosterol exerts an inhibitory effect on the in vitro enzymatic activity of SARS coronavirus 3C-like protease [15].…”

Section: Introductionmentioning

confidence: 99%

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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Indole Alkaloid Glycosides from the Aerial Parts of Strobilanthes cusia

Cited by 100 publications

References 15 publications

Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics

Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

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

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