ent-Kaurane Diterpenoids from Croton tonkinensis Inhibit LPS-Induced NF-κB Activation and NO Production

Giang, Phan Minh; Jin, Hui; Sơn, Phan Tống; Lee, Jeong Hyung; Hong, Young-Shick; Lee, Jun Young

doi:10.1021/np030139y

Cited by 52 publications

(53 citation statements)

References 12 publications

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“…Four ent-akurane diterpenoids 32-35 84 of Croton tonkinensis leaves and five ent-akurane diterpenoids 36-40 85 ( Fig. 4) of Isodon excisus aerial parts strongly inhibited the NF-kB activation and NO production in LPS-stimulated RAW 264.7 cells.…”

Section: Terpenoidsmentioning

confidence: 95%

“…This functional group can react with biological nucleophiles, especially the sulfhydryl group of the cysteine residue in the DNA-binding domain of the NF-kB subunit. 84,85 Taraxasteryl acetate (41) isolated from Pluchea sagittalis showed activity against H 2 O 2 -, phorbol 12-myristate 13-acetate (PMA)-and fMLP-induced ROS, sodium nitroprusside-induced reactive nitrogen species, and heat shock protein72 production in human neutrophils; and exhibited more potent topical anti-inflammatory activity than indomethacin in AA-, croton oil-and PMAinduced mice ear edema. 86 Agnuside (42), an iridoid glycoside, isolated from Vitex peduncularis showed a preferential inhibition of COX-2 greater than aspirin (IC 50 0.058 mg/mL), a nonselective COX-2 inhibitor.…”

Section: Terpenoidsmentioning

confidence: 99%

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Recent developments in anti‐inflammatory natural products

Gautam

Jachak

2009

Medicinal Research Reviews

393

230

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Many of the inflammatory diseases are becoming common in aging society throughout the world. The clinically used anti-inflammatory drugs suffer from the disadvantage of side effects and high cost of treatment (in case of biologics). Alternative to these drugs are traditional medicines and natural products, which offer a great hope in the identification of bioactive lead compounds and their development into drugs for treating inflammatory diseases. Since ancient times traditional medicines and phytopharmaceuticals are being used for the treatment of inflammatory and other disorders. The present review article describes anti-inflammatory natural products derived from plants and marine sources reported during last decade. The compounds described belong to different chemical classes such as alkaloids, steroids, terpenoids, polyphenolics, phenylpropanoids, fatty acids and lipids, and various miscellaneous compounds. The attempt is also being made to enumerate the possible leads, e.g. curcumin, resveratrol, baicalein, boswellic acid, betulinic acid, ursolic acid, and oleanolic acid, for further development with the help of structure-activity relationship (SAR) studies and their current status. In addition SAR studies carried out on the anti-inflammatory activity of flavonoid compounds and clinical studies performed on anti-inflammatory natural products are also discussed.

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Section: Terpenoidsmentioning

confidence: 95%

Section: Terpenoidsmentioning

confidence: 99%

Recent developments in anti‐inflammatory natural products

Gautam

Jachak

2009

Medicinal Research Reviews

393

230

View full text Add to dashboard Cite

show abstract

“…4,7) Among them, the ent-kaurane diterpenoids have cytotoxic and proapoptotic activities, 8) inhibit lipopolysaccharide-induced nuclear factor kappa B activation, 9) reduce inflammation, 10) inhibit silent information regulator two ortholog 1 (SIRT1), 11) and stimulate osteoblast differentiation. 12) AMP-activated protein kinase (AMPK) is a cellular energy status sensor found in all eukaryotes, which is activated under conditions of low intracellular ATP following stressors such as nutrient deprivation and hypoxia.…”

mentioning

confidence: 99%

An ent-Kaurane Diterpenoid from Croton tonkinensis Induces Apoptosis by Regulating AMP-Activated Protein Kinase in SK-HEP1 Human Hepatocellular Carcinoma Cells

Sul

Lee

Young

et al. 2013

Biological & Pharmaceutical Bulletin

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Hepatocellular carcinoma (HCC) is the most common type of liver cancer with high mortality worldwide. Traditional chemotherapy for HCC is not widely accepted by clinical practitioners because of its toxic side effects. Thus, there is a need to identify chemotherapeutic drugs against HCC. AMP-activated protein kinase (AMPK) is a biologic sensor for cellular energy status that acts a tumor suppressor and a potential cancer therapeutic target. The traditional Vietnamese medicinal plant Croton tonkinensis shows cytotoxicity in various cancer cells; however, its anticancer mechanism remains unclear. In this study, we determined whether the ent-kaurane diterpenoid ent-18-acetoxy-7β-hydroxy kaur-15-oxo-16-ene (CrT1) isolated from this plant plays a role as a chemotherapeutic drug targeting AMPK. CrT1 blocked proliferation in dose-and time-dependent manners in human hepatocellular carcinoma SK-HEP1 cells. CrT1 induced sub-G 1 arrest and caspase-dependent apoptosis. CrT1 activated caspase-3, -7, -8, -9, and poly(ADP-ribose) polymerase, and its effect was inhibited by z-VAD-fmk suppressing caspase-3 cleavage. CrT1 induced increases in p53 and Bax levels but decreased Bcl 2 levels. In addition, CrT1 resulted in increased translocation of cytochrome c into the cytoplasm. We showed that CrT1-activated AMPK activation was followed by modulating the mammalian target of rapamycin/p70S6K pathway and was inactivated by treating cells with compound C. Treatment with CrT1 and aminoimidazole carboxamide ribonucleotide (AICAR) synergistically activated AMPK. CrT1-induced AMPK activation regulated cell viability and apoptosis. These results suggest that CrT1 is a novel AMPK activator and that AMPK activation in SK-HEP1 cells is responsible for CrT1-induced anticancer activity including apoptosis.Key words hepatocellular carcinoma; AMP-activated protein kinase; ent-kaurane diterpenoid Hepatocellular carcinoma (HCC) is the most common type of liver cancer with high mortality and causes 662000 deaths worldwide each year. To date, HCC has a life-threatening and unsatisfactory prognosis. Once the diagnosis is confirmed, most patients are already at the advanced stage and have lost the opportunity for surgical intervention. Further characterization of underlying molecular mechanisms in HCC would bring new insights into HCC research and clinical treatment.

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“…[13][14][15][16] In addition, ent-kaurane diterpenes isolated from Rabdosia rubescens or Croton tonkinensis, showed anti-inflammatory activities in primary cultured rat microglia or RAW264.7 macrophages. 17,18) Moreover, Park et al found that siegeskaurolic acid, an ent-kaurane diterpene isolated from S. pubescens, significantly inhibited lipopolysaccharide (LPS)-induced inflammatory responses in RAW264.7 cells through down-regulation of the NF-κB binding activity. 19) Kirenol isolated from Herba Siegesbeckiae also reduces proinflammatory cytokines secretion, increase anti-inflammatory cytokines production of CII-specific lymphocytes from CIA rats, and exerts a potent anti-arthritic effect in collageninduced arthritis by modifying the balance of T cells.…”

mentioning

confidence: 99%

ent-Kaurane and ent-Pimarane Diterpenes from Siegesbeckia pubescens Inhibit Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia

Lee

Kim

Lee

et al. 2014

Biological & Pharmaceutical Bulletin

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The extract of Siegesbeckia pubescens herb and its chemical constituents were tested for the ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglia. The methanol extract and the 90% MeOH fraction of S. pubescens effectively attenuated lipopolysaccharide-induced nitric oxide production. Several steps of chromatography yielded eight ent-kaurane diterpenes (1-8) and one ent-pimarane diterpene (9) from the 90% MeOH fraction. Among these compounds, compounds 2-9 showed significant inhibitory effect on lipopolysaccharide-induced nitric oxide production in BV2 microglia. Compounds 3 and 9 concentration-dependently decreased the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), supported by quantitative real time polymerase chain reaction (PCR) and Western blot analysis. These results suggest that ent-kaurane and ent-pimarane diterpenes isolated from S. pubescens are expected to be potential candidates against neuroinflammation-related disease.

show abstract

ent-Kaurane Diterpenoids from Croton tonkinensis Inhibit LPS-Induced NF-κB Activation and NO Production

Cited by 52 publications

References 12 publications

Recent developments in anti‐inflammatory natural products

Recent developments in anti‐inflammatory natural products

An <i>ent</i>-Kaurane Diterpenoid from <i>Croton tonkinensis</i> Induces Apoptosis by Regulating AMP-Activated Protein Kinase in SK-HEP1 Human Hepatocellular Carcinoma Cells

<i>ent</i>-Kaurane and <i>ent</i>-Pimarane Diterpenes from <i>Siegesbeckia pubescens</i> Inhibit Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia

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