Coffee and cancer (hint: it is good news)

Dr. Weeks’ Comment:    Coffee is anti-cancer!  (But just make sure to drink organic coffee,  and don’t add the SUGAR and CREAM….) 

And what about coffee is so beneficial? 

Turns out it is a phytoestrogen which is related to niacin (vitamin B3)

 

Trigonelline is a novel phytoestrogen in coffee beans.

            J Nutr. 2009 Oct;139(10):1833-8. Epub 2009 Aug 26.

Allred KF, Yackley KM, Vanamala J, Allred CD.

Department of Nutrition and Food Science, Texas A&M University, College Station, TX 77843, USA.

Drinking coffee has been associated with the development of several endocrine-related cancers. The interpretation of these data has often been limited to the role that caffeine plays. Trigonelline (Trig), a niacin-related compound, is a natural constituent of coffee accounting for approximately 1% dry matter in roasted beans. Studies exploring the effects of this bioactive compound on mammalian cells are limited. The initial purpose of our studies was to determine whether Trig alters the actions of estradiol (E(2)), using proliferation of estrogen-dependent human breast cancer (MCF-7) cells as a model system. When cells were cotreated with suboptimal doses of E(2) (10 pmol/L) and Trig (100 pmol/L), an additive enhancement of MCF-7 growth was observed. In the absence of E(2), Trig stimulated MCF-7 cell proliferation in a dose-responsive manner and significantly enhanced cell growth at concentrations as low as 100 pmol/L. Cotreatment of MCF-7 cells with Trig and ICI 182,780, an estrogen receptor (ER) antagonist, inhibited Trig-induced cell proliferation. Trig treatment also induced activation of estrogen response element reporter assays in MCF-7 cells and increased expression of ER target genes (pS2, progesterone receptor, and cyclin D1) similar to E(2). While our data demonstrate that Trig activates the ER, competitive binding assays showed that Trig does not compete E(2) off of the ER at any concentration. This suggests that Trig is activating the ER through a separate mechanism. Collectively, these data demonstrate that Trig even at low concentrations stimulates MCF-7 cell growth and that this effect is mediated through ER, clearly identifying Trig as a novel phytoestrogen.

 


2: Biosci Biotechnol Biochem. 2005 Mar;69(3):653-8.

Anti-invasive activity of niacin and trigonelline against cancer cells.

Hirakawa N, Okauchi R, Miura Y, Yagasaki K.

Department of Applied Biological Science, Tokyo Noko University, Fuchu, Japan.

The effects of niacin, namely, nicotinic acid and nicotinamide, and trigonelline on the proliferation and invasion of cancer cells were studied using a rat ascites hepatoma cell line of AH109A in culture. Niacin and trigonelline inhibited the invasion of hepatoma cells at concentrations of 2.5-40 microM without affecting proliferation. Hepatoma cells previously cultured with a reactive oxygen species (ROS)-generating system showed increased invasive activity. Niacin and trigonelline suppressed this ROS-potentiated invasive capacity through simultaneous treatment of AH109A cells with the ROS-generating system. The present study indicates for the first time the anti-invasive activities of niacin and trigonelline against cancer cells.



3: Biol Pharm Bull. 1999 Jul;22(7):679-82.

Trigonelline-induced neurite outgrowth in human neuroblastoma SK-N-SH cells.

Tohda C, Nakamura N, Komatsu K, Hattori M.

Research Center for Ethnomedicines, Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Japan.

Extension of dendrites and axons in neurons may compensate and rescue damaged neuronal networks in the dementia brain. Our aim is to isolate and identify constituents of coffee beans exhibiting neurite outgrowth activity. Among the extracts of raw and roasted coffee beans, a methanol fraction of the ethanol extract (1 microg/ml) of raw beans increased significantly the percentage of cells with neurites in human neuroblastoma SK-N-SH cells. Among subfractions of this methanol fraction was a basic fraction (5 microg/ml) which exhibited significant neurite outgrowth activity. Finally, trigonelline in the basic fraction was identified to be active as far neurite extension was concerned. Treatment with trigonelline (30 microM) increased the percentage of cells with neurites at 3 and 6 d after treatment. In addition, the number of neurites reacting positively to phosphorylated neurofilament-H was increased by treatment with 30 microM trigonelline for 6 d, suggesting enhancement of axonal extension. These results show that trigonelline promotes functional neurite outgrowth.


4: Mutat Res. 1988 Feb;204(2):219-28.

h
Mutagenic activity of some coffee flavor ingredients.

Fung VA, Cameron TP, Hughes TJ, Kirby PE, Dunkel VC.

National Cancer Institute, Bethesda, MD 20892.

The mutagenicity of 4 coffee flavor ingredients (chlorogenic acid, caffeic acid, pyrazine, and trigonelline) was evaluated in the Salmonella plate incorporation assay and mouse lymphoma L5178Y TK +/- assay. Two of the compounds, pyrazine and trigonelline, were negative in both assays. The other two compounds, caffeic acid and chlorogenic acid, were positive in the mouse lymphoma assay but negative in the Salmonella assay.


5: Z Ernahrungswiss. 1977 Dec;16(4):248-55.

[Coffee and health]

[Article in German]

Czok G.

Coffee as a rule develops stimulating effects on the central nervous system, heart and circulation which are mainly caused by caffeine. In certain cases coffee may also have a sedative effect and sometimes even it is useful to fall asleep quickly. Furthermore coffee may be advantageous in the treatment of some functional disorders caused by lacking of dopamine, because coffee is able to increase the dopamine formation in brain. Concerning the effects of coffee in the gastrointestinal-tract and liver-bile system caffeine is only of secondary importance. Hereby certain roasting substances, possibly also chlorogenic acid or caffeic acid should be responsible for the stimulating effects observed in these organs. These stimulating effects could be caused whether directly or indirect e.g. by liberating gastrin or other gastrointestinal hormones. Vitamin niacin, which is formed in greater amounts from trigonelline during the roasting process, may also be important from the nutritional standpoint. Therefore coffee may be prescribed as a true drug in cases of deficiency in vitamin niacin or also in the pellagra disease. By extensive epidemiological studies performed lately it could be demonstrated that there exists no correlation between coffee consumption and certain risk factors as hypertension, heart infarction, diabetes, gout or cancer diseases. Furthermore there was no evidence that coffee or its caffeine content are able to induce genetic alterations or even malformations.

Trigonelline

Trigonelline.png

IUPAC name

 [show]

1-Methylpyridinium- 3-carboxylate

Other names

Nicotinic acid N- methylbetaine
Coffearine
Caffearine
Gynesine
Trigenolline

Identifiers

CAS number

535-83-1

SMILES

 [show]

C[N]1=CC(C([O])=O)=CC=C1

Properties

Molecular formula

C7H7NO2

Molar mass

137.14 g mol−1

Density

 ? g/cm3

Melting point

230-233 °C (monohydrate)
258-259 °C (hydrochloride)

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Trigonelline is an alkaloid with chemical formula C7H7NO2. It is an inner salt formed by the addition of a methyl group to the nitrogen atom of niacin. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine.[1]

Trigonelline occurs in many plants, it was isolated from fenugreek seeds (Trigonella foenum-graecum, thus the name)[2], garden peas, hemp seed, oats[3], potatoes, Stachys species, dahlia[4], Strophanthus species[5] and Dichapetalum cymosum[6]. Holtz, Kutscher and Theilmann have recorded its presence in a number of animals.[7]

Trigonelline is also found in coffee[8], where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth.[9] Higher levels of trigonelline is found in robusta coffee.

Trigonelline crystallises as a monohydrate from alcohol in hygroscopic prisms, mp. 130 °C or 218 °C (dry, dec.). It is readily soluble in water or warm alcohol, less so in cold alcohol, and slightly so in chloroform or ether. The salts crystallise well, the monohydrochloride, in leaflets, sparingly soluble in dry alcohol. The picrate forms shining prisms, mp. 198-200 °C, soluble in water but sparingly soluble in dry alcohol or ether. The alkaloid forms several aurichlorides: the normal salt, B•HCl•AuCl3, is precipitated when excess of gold chloride is added to the hydrochloride, and after crystallisation from dilute hydrochloric acid containing some gold chloride, has mp. 198 °C. Crystallised from water or very dilute hydrochloric acid, slender needles of B4•3 HAuCl4, mp. 186 °C, are obtained.

[edit] References

  1. ^ Merck Index, 11th Edition, 9606.
  2. ^ Jahns, Ber., 1885, 18, 2518.
  3. ^ Schulze and Frankfurt, Ber., 1894, 27, 709.
  4. ^ Schulze and Trier, Zeit. physiol. Chem., 1912, 76, 258.
  5. ^ Thoms, Ber., 1891, 31, 271, 404.
  6. ^ Rimington, Onderstepoort J., 1935, 5, 81.
  7. ^ Zeit. Biol., 1924, 81, 57.
  8. ^ Gorter, Annalen, 1910, 372, 237; cf. Polstorff, Chem. Soc. Abstr., 1910, ii, 234; Palladino, ibid, 1894, ii, 214; 1895, i, 629; Graf, ibid, 1904, i, 915; Nottbohm and Mayer, Zeit. Unters. Lebensmitt., 1931, 61, 429.
  9. ^ Daglia, M.; R. Tarsi, A. Papetti, P. Grisoli, C. Dacarro, C. Pruzzo, and G. Gazzani (2002). “Antiadhesive Effect of Green and Roasted Coffee on Streptococcus mutans’ Adhesive Properties on Saliva-Coated Hydroxyapatite Beads”. Journal of Agricultural and Food Chemistry 50: 1225–1229. doi:10.1021/jf010958t.

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