Pachymic acid

Last updated
Pachymic acid
Pachymic acid.png
Names
IUPAC name
3-Acetoxy-16-hydroxy-24-methylenelanost-8-en-21-oic acid
Preferred IUPAC name
(2R)-2-[(1R,2R,3aR,5aR,6S,9aS,11aR)-7-(Acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]-6-methyl-5-methylideneheptanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+ Yes check.svgY
    Key: JNUUNUQHXIOFDA-XTDASVJISA-N Yes check.svgY
  • InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h19,22,25-28,35H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1
    Key: VDYCLYGKCGVBHN-DRCQUEPLSA-N
  • CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)OC(=O)C)C)C)C)O)C(=O)O
Properties
C33H52O5
Molar mass 528.76 g/mol
Density 1.1±0.1 g/cm3
Boiling point 612.2±55.0 °C at 760 mmHg
Hazards
Flash point 184.7±25.0 °C [ citation needed ]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Pachymic acid is a naturally occurring steroid that can be extracted from the parasitic fungus Wolfiporia extensa (synonym Wolfiporia cocos ). The dried sclerotia of the fungus is used as a traditional Chinese medicine, and pachymic acid is thought to be the principal bioactive component of it. [1]

Effects

Pachymic acid is known to inhibit the Epstein–Barr virus and to inhibit the snake venom phospholipase A2. [2] It also has antitumor and anti-inflammatory properties. [1]

Related Research Articles

<span class="mw-page-title-main">Proton-pump inhibitor</span> Class of drugs for reducing stomach acid

Proton-pump inhibitors (PPIs) are a class of medications that cause a profound and prolonged reduction of stomach acid production. They do so by irreversibly inhibiting the stomach's H+/K+ ATPase proton pump.

<span class="mw-page-title-main">Putrescine</span> Foul-smelling organic chemical compound produced by the breakdown of amino acids

Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

<span class="mw-page-title-main">Protease</span> Enzyme that cleaves other proteins into smaller peptides

A protease is an enzyme that catalyzes proteolysis, breaking down proteins into smaller polypeptides or single amino acids, and spurring the formation of new protein products. They do this by cleaving the peptide bonds within proteins by hydrolysis, a reaction where water breaks bonds. Proteases are involved in many biological functions, including digestion of ingested proteins, protein catabolism, and cell signaling.

<i>Penicillium</i> Genus of fungi

Penicillium is a genus of ascomycetous fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production.

<span class="mw-page-title-main">Omeprazole</span> Stomach acid suppressing medication

Omeprazole, sold under the brand names Prilosec and Losec, among others, is a medication used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. Omeprazole is a proton-pump inhibitor (PPI) and its effectiveness is similar to other PPIs. It can be taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Cromoglicic acid</span>

Cromoglicic acid (INN)—also referred to as cromolyn (USAN), cromoglycate, or cromoglicate—is traditionally described as a mast cell stabilizer, and is commonly marketed as the sodium salt sodium cromoglicate or cromolyn sodium. This drug prevents the release of inflammatory chemicals such as histamine from mast cells.

<span class="mw-page-title-main">Chytridiomycosis</span> Amphibian disease

Chytridiomycosis is an infectious disease in amphibians, caused by the chytrid fungi Batrachochytrium dendrobatidis and Batrachochytrium salamandrivorans. Chytridiomycosis has been linked to dramatic population declines or extinctions of amphibian species in western North America, Central America, South America, eastern Australia, east Africa (Tanzania), and Dominica and Montserrat in the Caribbean. Much of the New World is also at risk of the disease arriving within the coming years. The fungus is capable of causing sporadic deaths in some amphibian populations and 100% mortality in others. No effective measure is known for control of the disease in wild populations. Various clinical signs are seen by individuals affected by the disease. A number of options are possible for controlling this disease-causing fungus, though none has proved to be feasible on a large scale. The disease has been proposed as a contributing factor to a global decline in amphibian populations that apparently has affected about 30% of the amphibian species of the world. Some research found evidence insufficient for linking chytrid fungi and chytridiomycosis to global amphibian declines, but more recent research establishes a connection and attributes the spread of the disease to its transmission through international trade routes into native ecosystems.

<span class="mw-page-title-main">Astemizole</span> Antihistamine drug

Astemizole was a second-generation antihistamine drug that has a long duration of action. Astemizole was discovered by Janssen Pharmaceutica in 1977. It was withdrawn from the market globally in 1999 because of rare but potentially fatal side effects.

Eicosatetraenoic acid (ETA) designates any straight chain 20:4 fatty acid. Eicosatetraenoic acid belongs to the family of eicosanoids, molecules synthesized from oxidized polyunsaturated fatty acids (PUFAs) to mediate cell-cell communication. The eicosanoids, working in tandem, contribute to a lipid signaling complex widely responsible for inducing an inflammatory immune response.

<span class="mw-page-title-main">Sclerotium</span> Mycelial mass

A sclerotium, is a compact mass of hardened fungal mycelium containing food reserves. One role of sclerotia is to survive environmental extremes. In some higher fungi such as ergot, sclerotia become detached and remain dormant until favorable growth conditions return. Sclerotia initially were mistaken for individual organisms and described as separate species until Louis René Tulasne proved in 1853 that sclerotia are only a stage in the life cycle of some fungi. Further investigation showed that this stage appears in many fungi belonging to many diverse groups. Sclerotia are important in the understanding of the life cycle and reproduction of fungi, as a food source, as medicine, and in agricultural blight management.

<span class="mw-page-title-main">Ursolic acid</span> Pentacyclic chemical compound found in fruits

Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

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

Antamanide is a cyclic decapeptide isolated from a fungus, the death cap: Amanita phalloides. It is being studied as a potential anti-toxin against the effects of phalloidin and for its potential for treating edema. It contains 1 valine residue, 4 proline residues, 1 alanine residue, and 4 phenylalanine residues with a structure of c(Val-Pro-Pro-Ala-Phe-Phe-Pro-Pro-Phe-Phe). It was isolated by determining the source of the anti-phalloidin activity from a lipophillic extraction from the organism. It has been shown that antamanide can react to form alkali metal ion complexes. These include complexes with sodium and calcium ions. When these complexes are formed, the cyclopeptide structure undergoes a conformational change.

<i>Wolfiporia extensa</i> Species of fungus

Wolfiporia extensa (Peck) Ginns is a fungus in the family Polyporaceae. It is a wood-decay fungus but has a subterranean growth habit. It is notable in the development of a large, long-lasting underground sclerotium that resembles a small coconut. This sclerotium called "(Chinese) Tuckahoe" or fu-ling(茯苓, pīnyīn: fúlíng), is not the same as the true tuckahoe used as Indian bread by Native Americans, which is the arrow arum, Peltandra virginica, a flowering tuberous plant in the arum family. W. extensa is also used extensively as a medicinal mushroom in Chinese medicine. Indications for use in the traditional Chinese medicine include promoting urination, to invigorate the spleen function, and to calm the mind.

<span class="mw-page-title-main">Beta-ketoacyl-ACP synthase III</span>

In enzymology, a β-ketoacyl-[acyl-carrier-protein] synthase III (EC 2.3.1.180) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

<i>Wolfiporia</i> Genus of fungi

Wolfiporia is a genus of fungi in the family Polyporaceae. The genus was circumscribed by Leif Ryvarden and Robert Lee Gilbertson in 1984 to contain the type species Wolfiporia cocos and W. dilatohypha. The genus is named in honor of mycologist Frederick Adolph Wolf, who was the first to officially describe the type species.

<span class="mw-page-title-main">Pseudogymnoascus destructans</span> Species of fungus

Pseudogymnoascus destructans is a psychrophilic (cold-loving) fungus that causes white-nose syndrome (WNS), a fatal disease that has devastated bat populations in parts of the United States and Canada. Unlike species of Geomyces, P. destructans forms asymmetrically curved conidia. Pseudogymnoascus destructans grows very slowly on artificial media and cannot grow at temperatures above 20 °C. It can grow around 4 °C to 20 °C, which encompasses the temperatures found in winter bat hibernacula. Phylogenic evaluation has revealed this organism should be reclassified under the family Pseudeurotiaceae, changing its name to Pseudogymnoascus destructans.

IDFP is an organophosphorus compound related to the nerve agent sarin.

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

Olivetolic acid is an organic compound that is an intermediate in the biosynthetic pathway of the cannabinoids in Cannabis sativa.

<span class="mw-page-title-main">Anziaic acid</span> Carboxylate ester

Anziaic acid is a depside found in lichens. It gives a red reaction in the C test. The two phenolic rings have a pentyl side chain. It is an ester dimer of olivetolic acid.

References

  1. 1 2 Shu, Shaohua; Chen, Bei; Zhou, Mengchun; Zhao, Xinmei; Xia, Haiyang; Wang, Mo (2013). "De Novo Sequencing and Transcriptome Analysis of Wolfiporia cocos to Reveal Genes Related to Biosynthesis of Triterpenoids". PLOS ONE. 8 (8): e71350. Bibcode:2013PLoSO...871350S. doi: 10.1371/journal.pone.0071350 . PMC   3743799 . PMID   23967197.
  2. "Pachymic acid Biological Test Results". PubChem compound database. 3 March 2016.