Syringaresinol

Last updated
Syringaresinol
(+)-Syringaresinol.svg
Names
IUPAC name
(7α,7′α,8α,8′α)-3,3′,5,5′-Tetramethoxy-7,9′:7′,9-diepoxylignane-4,4′-diol
Systematic IUPAC name
4,4′-[(1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2,6-dimethoxyphenol)
Other names
(+)-Syringaresinol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m0/s1
    Key: KOWMJRJXZMEZLD-HCIHMXRSSA-N
  • O4[C@H](c1cc(OC)c(O)c(OC)c1)[C@@H]2[C@@H]([C@H](OC2)c3cc(OC)c(O)c(OC)c3)C4
Properties
C22H26O8
Molar mass 418.442 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Syringaresinol is a lignan found in Castela emoryi , [1] in Prunus mume . [2]

This compound inhibits Helicobacter pylori motility in vitro . [2]

Related Research Articles

<span class="mw-page-title-main">Urea breath test</span> Medical test for a bacteria infection

The urea breath test is a rapid diagnostic procedure used to identify infections by Helicobacter pylori, a spiral bacterium implicated in gastritis, gastric ulcer, and peptic ulcer disease. It is based upon the ability of H. pylori to convert urea to ammonia and carbon dioxide. Urea breath tests are recommended in leading society guidelines as a preferred non-invasive choice for detecting H. pylori before and after treatment.

<span class="mw-page-title-main">Peptic ulcer disease</span> Ulcer of an area of the gastrointestinal tract

Peptic ulcer disease (PUD) is a break in the inner lining of the stomach, the first part of the small intestine, or sometimes the lower esophagus. An ulcer in the stomach is called a gastric ulcer, while one in the first part of the intestines is a duodenal ulcer. The most common symptoms of a duodenal ulcer are waking at night with upper abdominal pain, and upper abdominal pain that improves with eating. With a gastric ulcer, the pain may worsen with eating. The pain is often described as a burning or dull ache. Other symptoms include belching, vomiting, weight loss, or poor appetite. About a third of older people have no symptoms. Complications may include bleeding, perforation, and blockage of the stomach. Bleeding occurs in as many as 15% of cases.

<i>Helicobacter pylori</i> Species of bacteria

Helicobacter pylori, previously known as Campylobacter pylori, is a gram-negative, microaerophilic, spiral (helical) bacterium usually found in the stomach. Its helical shape is thought to have evolved in order to penetrate the mucoid lining of the stomach and thereby establish infection. The bacterium was first identified in 1982 by the Australian doctors Barry Marshall and Robin Warren. H. pylori has been associated with cancer of the mucosa-associated lymphoid tissue in the stomach, esophagus, colon, rectum, or tissues around the eye, and of lymphoid tissue in the stomach.

<i>Helicobacter</i> Genus of bacteria

Helicobacter is a genus of Gram-negative bacteria possessing a characteristic helical shape. They were initially considered to be members of the genus Campylobacter, but in 1989, Goodwin et al. published sufficient reasons to justify the new genus name Helicobacter. The genus Helicobacter contains about 35 species.

<span class="mw-page-title-main">Barry Marshall</span> Australian physician

Barry James Marshall is an Australian physician, Nobel Prize Laureate in Physiology or Medicine, Professor of Clinical Microbiology and Co-Director of the Marshall Centre at the University of Western Australia. Marshall and Robin Warren showed that the bacterium Helicobacter pylori plays a major role in causing many peptic ulcers, challenging decades of medical doctrine holding that ulcers were caused primarily by stress, spicy foods, and too much acid. This discovery has allowed for a breakthrough in understanding a causative link between Helicobacter pylori infection and stomach cancer.

<span class="mw-page-title-main">Achlorhydria</span> Medical condition

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<span class="mw-page-title-main">Robin Warren</span> Australian pathologist

John Robin Warren is an Australian pathologist, Nobel Laureate and researcher who is credited with the 1979 re-discovery of the bacterium Helicobacter pylori, together with Barry Marshall. The duo proved to the medical community that the bacterium Helicobacter pylori is the cause of most peptic ulcers.

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MALT lymphoma (MALToma) is a form of lymphoma involving the mucosa-associated lymphoid tissue (MALT), frequently of the stomach, but virtually any mucosal site can be affected. It is a cancer originating from B cells in the marginal zone of the MALT, and is also called extranodal marginal zone B cell lymphoma.

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Limosilactobacillus reuteri is a lactic acid bacterium found in a variety of natural environments, including the gastrointestinal tract of humans and other animals. It does not appear to be pathogenic and may have health effects.

Timeline of peptic ulcer disease and <i>Helicobacter pylori</i>

This is a timeline of the events relating to the discovery that peptic ulcer disease and some cancers are caused by H. pylori. In 2005, Barry Marshall and Robin Warren were awarded the Nobel Prize in Physiology or Medicine for their discovery that peptic ulcer disease (PUD) was primarily caused by Helicobacter pylori, a bacterium with affinity for acidic environments, such as the stomach. As a result, PUD that is associated with H. pylori is currently treated with antibiotics used to eradicate the infection. For decades prior to their discovery, it was widely believed that PUD was caused by excess acid in the stomach. During this time, acid control was the primary method of treatment for PUD, to only partial success. Among other effects, it is now known that acid suppression alters the stomach milieu to make it less amenable to H. pylori infection.

<span class="mw-page-title-main">Carcinogenic bacteria</span>

Cancer bacteria are bacteria infectious organisms that are known or suspected to cause cancer. While cancer-associated bacteria have long been considered to be opportunistic, there is some evidence that bacteria may be directly carcinogenic. The strongest evidence to date involves the bacterium H. pylori and its role in gastric cancer.

Helicobacter pylori eradication protocols is a standard name for all treatment protocols for peptic ulcers and gastritis in the presence of Helicobacter pylori infection. The primary goal of the treatment is not only temporary relief of symptoms but also total elimination of H. pylori infection. Patients with active duodenal or gastric ulcers and those with a prior ulcer history should be tested for H. pylori. Appropriate therapy should be given for eradication. Patients with MALT lymphoma should also be tested and treated for H. pylori since eradication of this infection can induce remission in many patients when the tumor is limited to the stomach. Several consensus conferences, including the Maastricht Consensus Report, recommend testing and treating several other groups of patients but there is limited evidence of benefit. This includes patients diagnosed with gastric adenocarcinoma, patients found to have atrophic gastritis or intestinal metaplasia, as well as first-degree relatives of patients with gastric adenocarcinoma since the relatives themselves are at increased risk of gastric cancer partly due to the intrafamilial transmission of H. pylori. To date, it remains controversial whether to test and treat all patients with functional dyspepsia, gastroesophageal reflux disease, or other non-GI disorders as well as asymptomatic individuals.

<span class="mw-page-title-main">Infectious causes of cancer</span>

Estimates place the worldwide risk of cancers from infectious causes at 16.1%. Viral infections are risk factors for cervical cancer, 80% of liver cancers, and 15–20% of the other cancers. This proportion varies in different regions of the world from a high of 32.7% in Sub-Saharan Africa to 3.3% in Australia and New Zealand. Helicobacter pylori is associated with stomach cancer, and Mycobacterium, some other bacteria and parasites also have an effect.

Helicobacter pylori virulence factor CagA is a 120–145kDa protein encoded on the 40kb cag pathogenicity island (PAI). H. pylori strains can be divided into CagA positive or negative strains. Approximately 60% of H. pylori strains isolated in Western countries carry cag PAI, whereas almost all of the East Asian isolates are cag PAI-positive.

Helicobacter felis is a bacterial species in the Helicobacteraceae family, Campylobacterales order, Helicobacter genus. This bacterium is Gram-negative, microaerophilic, urease-positive, and spiral-shaped. Its type strain is CS1T. It can be pathogenic.

Helicobacter heilmannii sensu lato refers to a group of bacterial species within the Helicobacter genus. The Helicobacter genus consists of at least 40 species of spiral-shaped flagellated, Gram-negative bacteria of which the by far most prominent and well-known species is Helicobacter pylori. H. pylori is associated with the development of gastrointestinal tract diseases such as stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers that are not lymphomas, and various subtypes of extranodal marginal zone lymphomass, e.g. those of the stomach, small intestines, large intestines, and rectumn. H. pylori has also been associated with the development of bile duct cancer and has been associated with a wide range of other diseases although its role in the development of many of these other diseases requires further study.

Helicobacter heilmannii s.s. is a species within the Helicobacter genus of Gram negative bacteria. Helicobacter pylori is by far the best known Helicobacter species primarily because humans infected with it may develop gastrointestinal tract diseases such as stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers of the non-lymphoma type, and various subtypes of extranodal marginal zone lymphomass, e.g. those of the stomach, small intestines, large intestines, and rectumn. H. pylori is also associated with the development of bile duct cancer and has been associated with a wide range of other diseases although its role in the development of many of these other diseases requires further study. Humans infected with H. heilmannii s.s. may develop some of the same gastrointestinal diseases viz., stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers that are not lymphomas, and extranodal marginal B cell lymphomas of the stomach. Other non-H. pylori Helicobacter species that are known to be associated with these gastrointestinal diseases are Helicobacter bizzozeronii, Helicobacter suis, Helicobacter felis, and Helicobacter salomonis. Because of their disease associations, these four Helicobacter species plus H. heilmannii s.s. are often group together and termed Helicobacter heilmannii sensu lato.

Vonoprazan/amoxicillin/clarithromycin, sold under the brand name Vonosap among others, is a co-packaged medication used for the treatment of Helicobacter pylori infection. It contains vonoprazan, a potassium-competitive acid blocker; amoxicillin, a beta-lactam antibiotic; and clarithromycin, a macrolide antibiotic.

<span class="mw-page-title-main">Vonoprazan/amoxicillin</span> Medication

Vonoprazan/amoxicillin, sold under the brand name Voquezna Dual Pak among others, is a co-packaged medication used for the treatment of Helicobacter pylori infection. It contains vonoprazan, a potassium-competitive acid blocker and amoxicillin, a beta-lactam antibiotic. It is taken by mouth.

References

  1. Stöcklin, W.; De Silva, L.B.; Geissman, T.A. (1969). "Constituents of holacantha emoryi". Phytochemistry. 8 (8): 1565. doi:10.1016/S0031-9422(00)85931-2.
  2. 1 2 Miyazawa, M; Utsunomiya, H; Inada, K; Yamada, T; Okuno, Y; Tanaka, H; Tatematsu, M (2006). "Inhibition of Helicobacter pylori motility by (+)-Syringaresinol from unripe Japanese apricot". Biological & Pharmaceutical Bulletin. 29 (1): 172–3. doi: 10.1248/bpb.29.172 . PMID   16394533.