Ganoderic acid

Last updated
Ganoderic acid A
Ganoderic acid.png
Names
IUPAC name
(25R)-7β,15α-Dihydroxy-3,11,23-trioxolanost-8-en-26-oic acid
Systematic IUPAC name
(2R,6R)-6-[(1R,3S,3aR,4S,5aR,9aS,11aR)-3,4-Dihydroxy-3a,6,6,9a,11a-pentamethyl-7,10-dioxo-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2-methyl-4-oxoheptanoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C30H44O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21,23,32,35H,8-14H2,1-7H3,(H,36,37)/t15-,16-,18-,19+,21+,23+,28+,29-,30+/m1/s1 X mark.svgN
    Key: DYOKDAQBNHPJFD-JNTBEZBXSA-N X mark.svgN
  • InChI=1/C30H44O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21,23,32,35H,8-14H2,1-7H3,(H,36,37)/t15-,16-,18-,19+,21+,23+,28+,29-,30+/m1/s1
    Key: DYOKDAQBNHPJFD-JNTBEZBXBK
  • OC(=O)[C@H](C)CC(=O)C[C@@H](C)[C@H]2C[C@H](O)[C@@]1(C)C/3=C(\C(=O)C[C@@]12C)[C@@]4(C)CCC(=O)[C@](C)(C)[C@@H]4C[C@@H]\3O
Properties
C30H44O7
Molar mass 516.67
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Ganoderic acids are a class of closely related triterpenoids (derivatives from lanosterol) found in Ganoderma mushrooms. For thousands of years, the fruiting bodies of Ganoderma fungi have been used in traditional medicines in East Asia. [1] [2] Consequently, there have been efforts to identify the chemical constituents that may be responsible for the putative pharmacological effects. The two most well described ganoderic acids out of the many that have been identified and characterized are ganoderic acids A and B. Some ganoderic acids have been found to possess biological activities including hepatoprotection, [3] anti-tumor effects, [4] and 5-alpha reductase inhibition. [5]

Related Research Articles

<span class="mw-page-title-main">Lingzhi (mushroom)</span> Species of fungus

Lingzhi, Ganoderma sichuanense, also known as reishi or Ganoderma lingzhi is a polypore fungus native to East Asia belonging to the genus Ganoderma.

<span class="mw-page-title-main">Thymidine kinase</span> Enzyme found in most living cells

Thymidine kinase is an enzyme, a phosphotransferase : 2'-deoxythymidine kinase, ATP-thymidine 5'-phosphotransferase, EC 2.7.1.21. It can be found in most living cells. It is present in two forms in mammalian cells, TK1 and TK2. Certain viruses also have genetic information for expression of viral thymidine kinases. Thymidine kinase catalyzes the reaction:

An angiogenesis inhibitor is a substance that inhibits the growth of new blood vessels (angiogenesis). Some angiogenesis inhibitors are endogenous and a normal part of the body's control and others are obtained exogenously through pharmaceutical drugs or diet.

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

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.

<span class="mw-page-title-main">Mdm2</span> Protein-coding gene in the species Homo sapiens

Mouse double minute 2 homolog (MDM2) also known as E3 ubiquitin-protein ligase Mdm2 is a protein that in humans is encoded by the MDM2 gene. Mdm2 is an important negative regulator of the p53 tumor suppressor. Mdm2 protein functions both as an E3 ubiquitin ligase that recognizes the N-terminal trans-activation domain (TAD) of the p53 tumor suppressor and as an inhibitor of p53 transcriptional activation.

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

Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus. It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.

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

Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch from which it gets its name, but also the ber tree, selfheal, the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul, flowering quince, rosemary, and Pulsatilla chinensis.

<i>Ganoderma applanatum</i> Species of fungus

Ganoderma applanatum is a bracket fungus with a cosmopolitan distribution.

<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.

<i>Ganoderma</i> Genus of mushroom

Ganoderma is a genus of polypore fungi in the family Ganodermataceae that includes about 80 species, many from tropical regions. They have a high genetic diversity and are used in traditional Asian medicines. Ganoderma can be differentiated from other polypores because they have a double-walled basidiospore. They may be called shelf mushrooms or bracket fungi.

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

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb (Schuttgelb), and Persian Berry Lake.

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

Honokiol is a lignan isolated from the bark, seed cones, and leaves of trees belonging to the genus Magnolia. It has been identified as one of the chemical compounds in some traditional eastern herbal medicines along with magnolol, 4-O-methylhonokiol, and obovatol.

<i>Ganoderma tsugae</i> Species of fungus

Ganoderma tsugae, also known as hemlock varnish shelf, is a flat polypore mushroom of the genus Ganoderma.

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

Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.

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

Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a sterol. Originally described in the 1930s from the yeast Saccharomyces cerevisiae, it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some in vitro bioactive properties, including cytotoxicity to some mammalian cell lines.

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

Phellibaumins are hispidin derivatives made by the fungus Phellinus. Five such derivatives have been identified, known as Phellibaumin A through E. Phellibaumins A and B are classified as pyranones, while Phellibaumins C, D, and E are classified as styrylpyranones.

Medicinal fungi are fungi that contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.

<i>Ganoderma microsporum</i> Species of mushroom

Ganoderma microsporum is a species of Ganoderma mushroom native to Taiwan that grows on willow trees. The specific epithet microsporum refers to the small size of its spores, measuring 6–8.5 by 4.5–5 μm, which is smaller than the spores of all other known types of Ganoderma.

<span class="mw-page-title-main">Fungal immunomodulatory protein</span> Functional compound found in fungi

Fungal immunomodulatory proteins (FIPs) are a type of functional compound found in various species of fungi. FIPs are part of the immunoglobulin (ig) family, which are structurally similar to human antibodies, and can interact with human peripheral blood mononuclear cells (PBMCs), causing these cells to secrete different types of hormones and regulate cellular activity.

References

  1. Nishitoba, Tsuyoshi; Goto, Sanae; Sato, Hiroji; Sakamura, Sadao (1989). "Bitter triterpenoids from the fungus Ganoderma applanatum". Phytochemistry. 28 (1): 193–7. Bibcode:1989PChem..28..193N. doi:10.1016/0031-9422(89)85036-8.
  2. Mizuno, T.; Wang, G.; Zhang, J.; Kawagishi, H.; Nishitoba, T.; Li, J. (1995). "Reishi, Ganoderma lucidum and Ganoderma tsugae: Bioactive substances and medicinal effects". Food Reviews International. 11: 151–166. doi:10.1080/87559129509541025. Closed Access logo transparent.svg
  3. Liu, Li-Ying; Chen, Hui; Liu, Chao; Wang, Hong-Qing; Kang, Jie; Li, Yan; Chen, Ruo-Yun (2014). "Triterpenoids of Ganoderma theaecolum and their hepatoprotective activities". Fitoterapia. 98: 254–9. doi:10.1016/j.fitote.2014.08.004. PMID   25111010.
  4. Wang, G.; Zhao, J.; Liu, J.; Huang, Y.; Zhong, J. J.; Tang, W. (2007). "Enhancement of IL-2 and IFN-γ expression and NK cells activity involved in the anti-tumor effect of ganoderic acid Me in vivo". International Immunopharmacology. 7 (6): 864–870. doi:10.1016/j.intimp.2007.02.006. PMID   17466920. Closed Access logo transparent.svg
  5. Liu, J.; Kurashiki, K.; Shimizu, K.; Kondo, R. (December 2006). "Structure–activity relationship for inhibition of 5α-reductase by triterpenoids isolated from Ganoderma lucidum". Bioorganic & Medicinal Chemistry. 14 (24): 8654–8660. doi:10.1016/j.bmc.2006.08.018. PMID   16962782. Closed Access logo transparent.svg