| 词条 | Isopimaric acid |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428765989 | ImageFile = Isopimaric acid.svg | ImageSize = 200px | IUPACName = (1R,4aR,4bS,7R,10aR)-7-Ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid | OtherNames = |Section1={{Chembox Identifiers | CASNo = 5835-26-7 | CASNo_Ref = {{cascite|changed|??}} | PubChem = 442048 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 512164 | SMILES = [H][C@]12[C@](C)(C(O)=O)CCC[C@]1(C)[C@]3([H])C(C[C@](C=C)(C)CC3)=CC2 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 390596 | InChI = 1/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1 | InChIKey = MXYATHGRPJZBNA-KRFUXDQABR | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = MXYATHGRPJZBNA-KRFUXDQASA-N | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 6039 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C09118}} |Section2={{Chembox Properties | C=20 | H=30 | O=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Isopimaric acid (IPA) is a toxin which acts as a large conductance Ca2+-activated K+ channel (BK channel) opener. SourcesIPA originates from many sorts of trees, especially conifers.[1] ChemistryIPA is one of the members of the resin acid group and it is a tricyclic diterpene.[1] TargetIPA acts on the large-conductance calcium activated K+ channels (BK channels).[2][3] Mode of actionBK channels are formed by α subunits and accessory β subunits arranged in tetramers. The α subunit forms the ion conduction pore and the β subunit contributes to channel gating. IPA interaction with the BK channel enhances Ca2+ and / or voltage sensitivity of the α subunit of BK channels without affecting the channel conductance. In this state BK channels can still be inhibited by one of their inhibitors, like charybdotoxin (CTX).[2][3] Opening of the BK channel leads to an increased K+-efflux which hyperpolarizes the resting membrane potential, reducing the excitability of the cell in which the BK-channel is expressed. ToxicityStudies on rainbow trout hepatocytes have shown that IPA increases intracellular calcium release, leading to a disturbance in the calcium homeostasis. This could be important in the possible toxicity of the toxin. See also
Notes1. ^1 {{cite journal | pmid = 8795202 | year = 1996 | last1 = Wilson | first1 = AE | last2 = Moore | first2 = ER | last3 = Mohn | first3 = WW | title = Isolation and characterization of isopimaric acid-degrading bacteria from a sequencing batch reactor | volume = 62 | issue = 9 | pages = 3146–51 | pmc = 168108 | journal = Applied and Environmental Microbiology}} 2. ^1 {{cite journal | pmid = 8807400 | year = 1996 | last1 = Kaczorowski | first1 = GJ | last2 = Knaus | first2 = HG | last3 = Leonard | first3 = RJ | last4 = McManus | first4 = OB | last5 = Garcia | first5 = ML | title = High-conductance calcium-activated potassium channels; structure, pharmacology, and function | volume = 28 | issue = 3 | pages = 255–67 | journal = Journal of bioenergetics and biomembranes | doi=10.1007/bf02110699}} 3. ^1 {{cite journal | pmid = 12237330 | year = 2002 | last1 = Imaizumi | first1 = Y | last2 = Sakamoto | first2 = K | last3 = Yamada | first3 = A | last4 = Hotta | first4 = A | last5 = Ohya | first5 = S | last6 = Muraki | first6 = K | last7 = Uchiyama | first7 = M | last8 = Ohwada | first8 = T | title = Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit | volume = 62 | issue = 4 | pages = 836–46 | journal = Molecular Pharmacology | doi=10.1124/mol.62.4.836}} References
{{Toxins}}{{Ion channel modulators}} 5 : Ion channel toxins|Carboxylic acids|Diterpenes|Non-protein ion channel toxins|Potassium channel openers |
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