Absolute stereochemistry of guaianolides, of matricin and its epimers, of yarrow proazulenes, and of chamazulene carboxylic acid

Imming, Peter; Goeters, Susanne; Pawlitzki, Gregor; Hempel, Bernd

doi:10.1002/chir.1041

Cited by 6 publications

(4 citation statements)

References 31 publications

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“…This effect was found to be due to inhibition of COX-2 enzyme activity by chamomile, with a mechanism of action similar to that attributed to NSAID [25]. Several studies also demonstrated anti-inflammatory effects of active components of chamomile including flavonoids (apigenin, luteolin and quercetin) and essential oils (α-bisabolol, bisabolol oxides A and B, chamazulene and α-and β-farnesene) [26][27][28]19]. Abe, et al indicated that chamomile essential oil tested at 0.1% concentration suppressed TNF-α-induced neutrophil adherence [27].…”

Section: Discussionmentioning

confidence: 78%

“…Abe, et al indicated that chamomile essential oil tested at 0.1% concentration suppressed TNF-α-induced neutrophil adherence [27]. Chamazulene carboxylic acid, a sesquiterpenic compound of chamomile, presents a chemical structure similar to profens [28], known as anti-inflammatory compounds that inhibit the key enzymes of prostaglandin metabolism [15].…”

Section: Discussionmentioning

confidence: 99%

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Effects of chamomile tea on inflammatory markers and insulin resistance in patients with type 2 diabetes mellitus

Zemestani¹,

Rafraf²,

Asghari‐Jafarabadi³

2018

Trends Gen Pract

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Aim:The purpose of this study was to evaluate the effects of chamomile tea consumption inflammatory markers and insulin resistance in subjects with type 2 diabetes mellitus (T2DM).Methods: This single-blind randomized controlled clinical trial was conducted on 64 individuals with T2DM (males and females) aged between 30 and 60 years. The intervention group (n=32) consumed chamomile tea (3g/150 mL hot water) 3 times per day immediately after meals for 8 weeks. The control group (n=32) followed a water regimen for the same intervention period. Fasting blood samples, anthropometric measurements and 3-day, 24-h dietary recalls were collected at the baseline and at the end of the trial. Data were analysed by independent t test, paired t test, Pearson correlation test, and analysis of covariance.Results: Analysis of covariance showed that tumour necrosis factor-α (TNFα) and high sensitive C-reactive protein (hs-CRP) levels and homeostatic model assessment for insulin resistance (HOM-IR) were significantly decreased by 4.87%, 57.20% and 23.60% respectively in chamomile group compared with these variables in control group at the end of the intervention (all p<0.05). There was significant positive correlation between the changes of serum TNFα and hs-CRP with HOMA-IR (r=0.567, p<0.001 and r= 0.520, p<0.001, respectively) in chamomile tea group at the end of the study. Conclusion::Short term intake of chamomile tea has beneficial effects on inflammatory markers and insulin resistance in patients with T2DM. Higher larger sample population and a longer intervention period may be required to show significant clinical improvements.

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Section: Discussionmentioning

confidence: 78%

Section: Discussionmentioning

confidence: 99%

Effects of chamomile tea on inflammatory markers and insulin resistance in patients with type 2 diabetes mellitus

Zemestani¹,

Rafraf²,

Asghari‐Jafarabadi³

2018

Trends Gen Pract

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“…Its stereogenic center has an S-configuration, the same configuration of the COX-inhibitory eutomers of profens. 16 In an in vitro assay 17 with isolated COX-1, 1 showed almost no inhibition (17.4 ( 6.2% at 50 µM, Table 1). In contrast, 1 did inhibit isolated COX-2 enzyme: 43.5 ( 4.0% at 50 µM.…”

Section: Resultsmentioning

confidence: 96%

“…Structurally, 1 is a natural profen. Its stereogenic center has an S- configuration, the same configuration of the COX-inhibitory eutomers of profens . In an in vitro assay with isolated COX-1, 1 showed almost no inhibition (17.4 ± 6.2% at 50 μM, Table ).…”

Section: Resultsmentioning

confidence: 98%

Chamazulene Carboxylic Acid and Matricin: A Natural Profen and Its Natural Prodrug, Identified through Similarity to Synthetic Drug Substances

et al. 2006

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Chamazulene carboxylic acid (1) is a natural profen with anti-inflammatory activity and a degradation product of proazulenic sesquiterpene lactones, e.g., matricin. Both 1 and proazulenes occur in chamomile (Matricaria recutita), yarrow (Achillea millefolium), and a few other Asteraceae species. It was isolated in improved yields, characterized physicochemically, and found to be an inhibitor of cyclooxygenase-2, but not of cyclooxygenase-1. It had anti-inflammatory activity in several animal models with local and systemic application. When human volunteers were given matricin orally, plasma levels of 1 were found to be in the micromolar range. Matricin was converted to 1 in artificial gastric fluid, but not in artificial intestinal fluid. Matricin and the yarrow proazulenes are proposed to be anti-inflammatory through conversion to 1. Intriguingly, the biological activity of the natural compound 1 was found because of its similarity to fully synthetic drug substances. This is the reverse process of the common lead function of natural compounds in drug discovery.

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Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities

et al. 2013

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Nine guaiane‐type sesquiterpenes and one eudesmane‐type one – namely argyinolides A–J (1–10) – as well as nine known analogues were isolated from the leaves of Artemisia argyi Levl. et Vant. Their structures were determined by interpretation of spectroscopic data (MS, 1D and 2D NMR). A combination of X‐ray crystal diffraction, specific optical rotations, CD spectroscopy, ECD calculation, and Mosher ester methods was employed to resolve the absolute configurations of the isolated compounds. Biological investigations into their cytotoxicities and anti‐inflammatory effects showed that 1, 13, 16, and 18 were remarkably cytotoxic against Bel‐742 and/or A549 cells, with IC50 values of 3.3–6.0 μM, whereas 7, 11–13, 16, and 18 exhibited sound inhibitory activity on LPS‐stimulated NO production in BV‐2 microglial cells, with IC50 values ranging from 3.2 to 8.6 μM. In addition, a brief discussion on the applicability of Geissman's rule for the sesquiterpene lactones, the probable reason for the presence of chlorine‐containing sesquiterpenes, and preliminary structure–activity relationships (SARs) are included.

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Absolute stereochemistry of guaianolides, of matricin and its epimers, of yarrow proazulenes, and of chamazulene carboxylic acid

Cited by 6 publications

References 31 publications

Effects of chamomile tea on inflammatory markers and insulin resistance in patients with type 2 diabetes mellitus

Effects of chamomile tea on inflammatory markers and insulin resistance in patients with type 2 diabetes mellitus

Chamazulene Carboxylic Acid and Matricin: A Natural Profen and Its Natural Prodrug, Identified through Similarity to Synthetic Drug Substances

Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities

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