Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

Li, Xiangmei; Jiang, Xian‐Jun; Yang, Ku; Wang, Lixia; Wen, Shi-Zhen; Wang, Fei

doi:10.1007/s13659-016-0107-5

Cited by 17 publications

(5 citation statements)

References 16 publications

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“…Many plant-derived compounds have anti-cancer activities. Previous studies of prenylated coumarins indicated that ethanol extracts of P. praeruptorum exhibit in vitro cytotoxic activity against several human cancer cell lines [ 18 ]. Additional research reported that an angular pyranocoumarin extracted from P. praeruptoruon inhibited the proliferation and induced the apoptosis of U266 cells by upregulating caspase-8 and -3 proteins, and downregulating phospho-ERK and phospho-AKT proteins and hTERT mRNA [ 19 ].…”

Section: Discussionmentioning

confidence: 99%

Praeruptorin A Inhibits Human Cervical Cancer Cell Growth and Invasion by Suppressing MMP-2 Expression and ERK1/2 Signaling

Lin

Chiou

et al. 2017

IJMS

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Praeruptorin A (PA) is a pyranocumarin present in the dried root of Peucedanumpraeruptorum Dunn that has anticancer effects against several types of cells. However, the effect of PA on human cervical cancer cells is unknown. Our results indicate that PA significantly inhibited cell proliferation, colony formation, migration, invasion, and wound closure of HeLa and SiHa cells, induced cell cycle arrest at G0/G1 phase, upregulated Rb, p16, p21 and p27 proteins and downregulated cyclin D1 and S-phase kinase-associated protein 2 (Skp2) proteins. PA also significantly reduced expression of matrix metalloproteinase-2 (MMP-2) and increased expression of tissue inhibitor of metalloproteinase-2 (TIMP-2). In addition, PA suppressed ERK1/2 activation and increased the effect of PD98059 (a specific MEK1/2 inhibitor) in downregulation of MMP-2 and upregulation of TIMP-2. PA treatment inhibited the effect of 12-O-tetradecanoylphorbol-13-acetate (TPA) on upregulation of ERK1/2 activation, MMP-2 expression, cellular migration, and invasion of HeLa cells. Our findings are the first to demonstrate the activity of PA against cervical cancer cells, and suggest this agent has promise as a therapeutic agent in treatment of human cervical cancer.

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Section: Discussionmentioning

confidence: 99%

Praeruptorin A Inhibits Human Cervical Cancer Cell Growth and Invasion by Suppressing MMP-2 Expression and ERK1/2 Signaling

Lin

Chiou

et al. 2017

IJMS

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“…The individual EtOAc extracts of the roots and fruit of M. integerrimum were separated by various chromatographic techniques to obtain a new compound (1) together with 23 known compounds (2-24), 6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin (2) (Li et al 2016), phebalosin (3) (Ito et al 1987), murralongin (4) (Talapatra et al 1973), osthenon (5) (Ito et al 1987), microminutin (6) (Suthiwong et al 2014), minutuminolate (7) (Lekphrom et al 2016), murrangatin acetate (8) (Ito et al 1987), (-)-murrangatin (9) (Ito et al 1990), 2′-Oethylmurrangatin (10) (Choudhary et al 2002), minumicrolin (11) (Ito et al 1990), hopeyhopin (12) (Dominguez et al 1977), dehydrogeijerin (13) (Dominguez et al 1977), isoscopoletin (14) (Shafizadeh et al 1970), scopoletin (15) (Cassady et al 1979), citropten (16) (Gray et al 1978), micromelin (17) (Cassady et al 1979), dihydromicromelin B (18) (Das et al 1994), acetyldihydromicromelin A (19) (Das et al 1994), flindulatin (20) (Collins et al 2004), gossypetin 3,7,8,4′-tetramethylether (21) (Wollenber et al 2008), 5,7-dihydroxy-3,4′,6,8-tetramethoxyflavone (22) (Silva et al 2005), 5,7-dihydroxy-3,8,4′-trimethoxyflavone (23) (Tandon et al 1977) and acerosin (24) (Greenham et al 2001).…”

Section: Resultsmentioning

confidence: 99%

Coumarins and flavones from the fruit and root extracts of Micromelum integerrimum

Suthiphasilp

Maneerat

Andersen

et al. 2018

Natural Product Research

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A phytochemical investigation of the fruit and root extracts of Micromelum integerrimum resulted in the isolation and identification of a new compound, integerravone (1), together with 23 known compounds (2-24). Their structures were characterized by spectroscopic methods as well as comparisons made from the literature. Compounds 2, 3-15, 17-18 and 20-23 were evaluated for their cytotoxicities against the colon cancer cell line, HCT116. All of them were inactive at 50 µM. Most of the phenolic compounds were evaluated for their antioxidant activity using the DPPH assay. Compounds 14 and 22-24 showed antioxidant activity with IC50 values ranging from 24.83-135.05 µM.

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“…Angular pyranocoumarin extracted from P. praeruptoruom reportedly inhibits proliferation and induces apoptosis in human U266 myeloma cells by upregulating caspase-8 and caspase-3 proteins and downregulating phospho-ERK and phospho-AKT proteins and hTERT mRNA [41]. Prenylated coumarins, the ethanol extracts of P. praeruptorum, exhibit in vitro cytotoxic activity against various types of human cancer cells [42]. Pyranocoumarins from the root extracts of P. praeruptorum Dunn, reportedly reduce nitric oxide production and inhibit the multidrug-resistant protein-mediated efflux of drugs [23].…”

Section: Discussionmentioning

confidence: 99%

Antiproliferative and Antimetastatic Effects of Praeruptorin C on Human Non–Small Cell Lung Cancer through Inactivating ERK/CTSD Signalling Pathways

et al. 2020

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Praeruptorin C (PC) reportedly has beneficial effects in terms of antiinflammation, antihypertension, and antiplatelet aggregation, and it potentially has anticancer activity. However, the effect of PC on human non–small cell lung cancer (NSCLC) is largely unknown. Compared with the effects of praeruptorin A and praeruptorin B, we observed that PC significantly suppressed cell proliferation, colony formation, wound closure, and migration and invasion of NSCLC cells. It induced cell cycle arrest in the G0/G1 phase, downregulated cyclin D1 protein, and upregulated p21 protein. PC also significantly reduced the expression of cathepsin D (CTSD). In addition, the phosphorylation/activation of the ERK1/2 signalling pathway was significantly suppressed in PC-treated NSCLC cells. Cotreatment with PC and U0126 synergistically inhibited CTSD expression, cell migration, and cell invasion, which suggests that the ERK1/2 signalling pathway is involved in the downregulation of CTSD expression and invasion activity of NSCLC cells by PC. These findings are the first to demonstrate the inhibitory effects of PC in NSCLC progression. Therefore, PC may represent a novel strategy for treating NSCLC.

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Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

Cited by 17 publications

References 16 publications

Praeruptorin A Inhibits Human Cervical Cancer Cell Growth and Invasion by Suppressing MMP-2 Expression and ERK1/2 Signaling

Praeruptorin A Inhibits Human Cervical Cancer Cell Growth and Invasion by Suppressing MMP-2 Expression and ERK1/2 Signaling

Coumarins and flavones from the fruit and root extracts of Micromelum integerrimum

Antiproliferative and Antimetastatic Effects of Praeruptorin C on Human Non–Small Cell Lung Cancer through Inactivating ERK/CTSD Signalling Pathways

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