Cafestol

Last updated
Cafestol
Cafestol.svg
Names
IUPAC name
3,18-(Epoxymetheno)-19-nor-5β,8α,9β,10α,13β,16β-kaur-3-ene-16α,17-diol
Systematic IUPAC name
(3bS,5aS,7R,8R,10aR,10bS)-7-(Hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13?,15-,17+,18-,19+,20+/m1/s1
    Key: DNJVYWXIDISQRD-GTATUSGQBK
  • OC[C@@]5(O)C[C@@]31C[C@@H]5CC[C@H]1[C@]4(C)CCc2occc2[C@H]4CC3
Properties
C20H28O3
Molar mass 316.441 g·mol−1
Melting point 158 to 162 °C (316 to 324 °F; 431 to 435 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cafestol is a diterpenoid molecule present in coffee beans. It is one of the compounds that may be responsible for proposed biological and pharmacological effects of coffee. [1]

Contents

Sources

A typical bean of Coffea arabica contains about 0.4% to 0.7% cafestol by weight. [2] Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee, Turkish coffee or Greek coffee. In paper-filtered coffee drinks such as drip brewed coffee, it is present in only negligible amounts, as the paper filter in drip filtered coffee retains the diterpenes. [3]

Research into biological activity

Coffee consumption has been associated with a number of effects on health and cafestol has been proposed to produce these through a number of biological actions. [4] Studies have shown that regular consumption of boiled coffee increases serum cholesterol whereas filtered coffee does not. [5] Cafestol may act as an agonist ligand for the nuclear receptor farnesoid X receptor and pregnane X receptor, blocking cholesterol homeostasis. Thus cafestol can increase cholesterol synthesis. [6]

Cafestol has also shown anticarcinogenic properties in rats. [7]

Cafestol also has neuroprotective effects in a Drosophila fruit fly model of Parkinson's disease. [8] [9]

See also

Related Research Articles

<i>Coffea</i> Genus of flowering plants

Coffea is a genus of flowering plants in the family Rubiaceae. Coffea species are shrubs or small trees native to tropical and southern Africa and tropical Asia. The seeds of some species, called coffee beans, are used to flavor various beverages and products. The fruits, like the seeds, contain a large amount of caffeine, and have a distinct sweet taste.

<span class="mw-page-title-main">Caffeine</span> Central nervous system stimulant

Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class. It is mainly used as a eugeroic (wakefulness promoter) or as a mild cognitive enhancer to increase alertness and attentional performance. Caffeine acts by blocking binding of adenosine to the adenosine A1 receptor, which enhances release of the neurotransmitter acetylcholine. Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors. Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase.

<span class="mw-page-title-main">Niacin</span> Organic compound and a form of vitamin B3

Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds. Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness. Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.

<span class="mw-page-title-main">Coffee</span> Brewed beverage made from coffee beans

Coffee is a beverage brewed from roasted coffee beans. Darkly colored, bitter, and slightly acidic, coffee has a stimulating effect on humans, primarily due to its caffeine content. It has the highest sales in the world market for hot drinks.

Decaffeination is the removal ("de-") of caffeine from coffee beans, cocoa, tea leaves, and other caffeine-containing materials. Decaffeinated products are commonly termed by the abbreviation decaf. Decaffeinated drinks contain typically 1–2% of the original caffeine content, but sometimes as much as 20%.

<i>Coffea arabica</i> Species of coffee plant

Coffea arabica, also known as the Arabica coffee, is a species of flowering plant in the coffee and madder family Rubiaceae. It is believed to be the first species of coffee to have been cultivated and is the dominant cultivar, representing about 60% of global production. Coffee produced from the less acidic, more bitter, and more highly caffeinated robusta bean makes up most of the remaining coffee production. The natural populations of Coffea arabica are restricted to the forests of South Ethiopia and Yemen.

<span class="mw-page-title-main">Coffee bean</span> Seed of the coffee plant

A coffee bean is a seed from the Coffea plant and the source for coffee. It is the pit inside the red or purple fruit. This fruit is often referred to as a coffee cherry, and like the cherry, it is a fruit with a pit. Even though the coffee beans are not technically beans, they are referred to as such because of their resemblance to true beans. The fruits most commonly contain two stones with their flat sides together. A small percentage of cherries contain a single seed, called a "peaberry". Peaberries make up only around 10% to 15% of all coffee beans. It is a fairly common belief that they have more flavour than normal coffee beans. Like Brazil nuts and white rice, coffee beans consist mostly of endosperm.

<i>Coffea canephora</i> Species of coffee plant

Coffea canephora is a species of coffee plant that has its origins in central and western sub-Saharan Africa. It is a species of flowering plant in the family Rubiaceae. Though widely known as Coffea robusta, the plant is scientifically identified as Coffea canephora, which has two main varieties, robusta and nganda.

<span class="mw-page-title-main">Farnesoid X receptor</span> Protein-coding gene in the species Homo sapiens

The bile acid receptor (BAR), also known as farnesoid X receptor (FXR) or NR1H4, is a nuclear receptor that is encoded by the NR1H4 gene in humans.

<span class="mw-page-title-main">Pregnane X receptor</span> Mammalian protein found in Homo sapiens

In the field of molecular biology, the pregnane X receptor (PXR), also known as the steroid and xenobiotic sensing nuclear receptor (SXR) or nuclear receptor subfamily 1, group I, member 2 (NR1I2) is a protein that in humans is encoded by the NR1I2 gene.

<span class="mw-page-title-main">Dihydroergocryptine</span> Chemical compound

Dihydroergocryptine (DHEC), sold under the brand names Almirid and Cripar among others, is a dopamine agonist of the ergoline group that is used as an antiparkinson agent in the treatment of Parkinson's disease. It is taken by mouth.

<span class="mw-page-title-main">Guggulsterone</span> Chemical compound

Guggulsterone is a phytosteroid found in the resin of the guggul plant, Commiphora mukul. Guggulsterone can exist as either of two stereoisomers, E-guggulsterone and Z-guggulsterone. In humans, it acts as an antagonist of the farnesoid X receptor, which was once believed to result in decreased cholesterol synthesis in the liver. Several studies have been published that indicate no overall reduction in total cholesterol occurs using various dosages of guggulsterone, and levels of low-density lipoprotein increased in many people. Nevertheless, guggulsterone is an ingredient in many nutritional supplements. Guggulsterone was also found to have interactions with the viral ADP ribose phosphatase enzyme of SARS-CoV-2 and has been proposed as a potential candidate for the development of therapeutics for the treatment of COVID-19.

A nicotinic agonist is a drug that mimics the action of acetylcholine (ACh) at nicotinic acetylcholine receptors (nAChRs). The nAChR is named for its affinity for nicotine.

<span class="mw-page-title-main">Tebanicline</span> Chemical compound

Tebanicline is a potent synthetic nicotinic (non-opioid) analgesic drug developed by Abbott. It was developed as a less toxic analog of the potent poison dart frog-derived compound epibatidine, which is about 200 times stronger than morphine as an analgesic, but produces extremely dangerous toxic side effects. Like epibatidine, tebanicline showed potent analgesic activity against neuropathic pain in both animal and human trials, but with far less toxicity than its parent compound. It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes.

<span class="mw-page-title-main">GTS-21</span> Chemical compound

GTS-21 is a drug that has been shown to enhance memory and cognitive function. It has been studied for its potential therapeutic uses, particularly in the treatment of neurodegenerative diseases and psychiatric disorders.

<span class="mw-page-title-main">Kahweol</span> Chemical compound

Kahweol is a diterpenoid molecule found in the beans of Coffea arabica and is structurally related to cafestol. Its name derives from the Arabic قهوة qahwa meaning "coffee".

<span class="mw-page-title-main">PHA-543,613</span> Chemical compound

PHA-543,613 is a drug that acts as a potent and selective agonist for the α7 subtype of neural nicotinic acetylcholine receptors, with a high level of brain penetration and good oral bioavailability. It is under development as a possible treatment for cognitive deficits in schizophrenia. It reduces excitotoxicity and protects striatal dopaminergic neurons in rat models. It also potentiates cognitive enhancement from memantine, decreases dynorphin release and inhibits GSK-B3.

<span class="mw-page-title-main">BP-897</span> Chemical compound

BP-897 is a drug used in scientific research which acts as a potent selective dopamine D3 receptor partial agonist with an in vitro intrinsic activity of ~0.6 and ~70x greater affinity for D3 over D2 receptors and is suspected to have partial agonist or antagonist activity in vivo. It has mainly been used in the study of treatments for cocaine addiction. A study comparing BP-897 with the potent, antagonistic, and highly D3 selective SB-277,011-A found, "SB 277011-A (1–10 mg/kg) was able to block cue-induced reinstatement of nicotine-seeking, indicating that DRD3 selective antagonism may be an effective approach to prevent relapse for nicotine. In contrast, BP 897 did not block the cue-induced reinstatement of nicotine-seeking or nicotine-taking under the FR5 schedule."

References

  1. Ludwig, I. A.; Clifford, M. N.; Lean, M. E.; Ashihara, H.; Crozier, A. (August 2014). "Coffee: biochemistry and potential impact on health". Food & Function. 5 (8): 1695–1717. doi:10.1039/c4fo00042k. PMID   24671262. S2CID   29389074.
  2. Kitzberger, C.; Scholz, M.; Benassi, M. (2014). "Bioactive compounds content in roasted coffee from traditional and modern Coffea arabica cultivars grown under the same edapho-climatic conditions". Food Research International. 61: 61–66. doi:10.1016/j.foodres.2014.04.031.
  3. Zhang, C.; Linforth, R.; Fisk, I. D. (2012). "Cafestol extraction yield from different coffee brew mechanisms". Food Research International. 49: 27–31. doi: 10.1016/j.foodres.2012.06.032 .
  4. Higdon, J. V.; Frei, B. (2006). "Coffee and health: a review of recent human research". Critical Reviews in Food Science and Nutrition. 46 (2): 101–123. doi:10.1080/10408390500400009. PMID   16507475.
  5. Urgert, R.; Katan, M. B. (1997). "The cholesterol-raising factor from coffee beans". Annual Review of Nutrition. 17: 305–324. doi:10.1146/annurev.nutr.17.1.305. PMC   1295997 . PMID   9240930.
  6. Ricketts, M. L.; Boekschoten, M. V.; Kreeft, A. J.; Hooiveld, G. J.; Moen, C. J.; Müller, M.; Frants, R. R.; Kasanmoentalib, S.; Post, S. M.; Princen, H. M.; Porter, J. G.; Katan, M. B.; Hofker, M. H.; Moore, D. D. (2007). "The cholesterol-raising factor from coffee beans, cafestol, as an agonist ligand for the farnesoid and pregnane X receptors". Molecular Endocrinology. 21 (7): 1603–1616. doi: 10.1210/me.2007-0133 . PMID   17456796.
  7. National Toxicology Program (October 1999). "Cafestol (CASRN 469-83-0) and Kahweol (CASRN 6894-43-5) — Review of Toxicological Literature" (PDF). Archived from the original (PDF) on November 1, 2004.
  8. Trinh, K.; Andrews, L.; Krause, J.; Hanak, T.; Lee, D.; Gelb, M.; Pallanck, L. (April 2010). "Decaffeinated coffee and nicotine-free tobacco provide neuroprotection in Drosophila models of Parkinson's disease through an NRF2-dependent mechanism". The Journal of Neuroscience. 30 (16): 5525–5532. doi:10.1523/JNEUROSCI.4777-09.2010. PMC   3842467 . PMID   20410106.
  9. Callaway, E. (April 23, 2010). "Parkinson's protection without caffeine or nicotine" . New Scientist.