Manoalide: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 383787917

| ImageFile=Manoalide.png

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| PIN=(5''R'')-5-Hydroxy-4-<nowiki/>{(2''R'',6''R'')-6-hydroxy-5-[(3''E'')-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2''H''-pyran-2-yl}furan-2(5''H'')-one

| OtherNames=

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=75088-80-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E1DK0157K9

| PubChem= 6437368

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 66666

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 463914

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C17156

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4941932

| SMILES = CC1=C(C(CCC1)(C)C)CC/C(=C/CCC2=CC[C@@H](O[C@H]2O)C3=CC(=O)O[C@H]3O)/C

| InChI = 1/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

| InChIKey = FGJIDQWRRLDGDB-CPIXEKRIBK

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = FGJIDQWRRLDGDB-CPIXEKRISA-N

| Formula=C₂₅H₃₆O₅

| MolarMass=416.55034

| Appearance=

| Density=

| MeltingPt=

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'''Manoalide''' is a [[calcium channel blocker]]. It has antibiotic, analgesic and anti-inflammatory effects and is found in some [[Porifera|sponges]], including the West Pacific species ''[[Luffariella variabilis]]''.<ref>Brusca, Richard C. and Brusca, Gary J. ''Invertebrates''. 2nd ed. Sinauer Associates, 2002. p. 202.</ref>

Its functions are made possible by the permanent blockage of [[phospholipase A2]] and C<ref>{{Cite book|url=https://www.worldcat.org/oclc/743217704|title=Oxford dictionary of biochemistry and molecular biology|date=2006|publisher=Oxford University Press|others=Cammack, Richard, Ph. D.|isbn=978-1-61344-113-8|edition=Rev.|location=Oxford|oclc=743217704}}</ref> with lysine residues. This could be made possible through the functional groups incorporated in gamma-hydroxybutenolide, alpha-hydroxydihydropyran and the trimethylcyclohexenyl. The gamma-hydroxybutenolide ring is present in the reaction between manoalide and phospholipase A2, the hemiacetal in alpha-hydroxydihydropyran is needed for permanent binding and hydrophobic trimethylcyclohexenyl ring makes it possible for non-bonded interactions to interact between manoalide and phospholipase A2 to strengthen the reaction. <ref>{{Cite journal|date=2020-12-01|title=Molecular Pharmacology: 98 (6)|url=https://molpharm.aspetjournals.org/content/98/6|journal=Molecular Pharmacology|language=en|volume=98|issue=6|issn=0026-895X}}</ref> Due to its potential of permanent inhibition, it was made possible for it to take part in oral cancer<ref>{{Cite journal|last1=Wang|first1=Hui-Ru|last2=Tang|first2=Jen-Yang|last3=Wang|first3=Yen-Yun|last4=Farooqi|first4=Ammad Ahmad|last5=Yen|first5=Ching-Yu|last6=F. Yuan|first6=Shyng-Shiou|last7=Huang|first7=Hurng-Wern|last8=Chang|first8=Hsueh-Wei|date=2019|title=Manoalide Preferentially Provides Antiproliferation of Oral Cancer Cells by Oxidative Stress-Mediated Apoptosis and DNA Damage|journal= Cancers|volume=11|issue=9|page=1303|doi=10.3390/cancers11091303|pmid=31487907|pmc=6770486|doi-access=free}}</ref> and Hepatitis C<ref>{{Cite journal|last1=Salam|first1=Kazi Abdus|last2=Furuta|first2=Atsushi|last3=Noda|first3=Naohiro|last4=Tsuneda|first4=Satoshi|last5=Sekiguchi|first5=Yuji|last6=Yamashita|first6=Atsuya|last7=Moriishi|first7=Kohji|last8=Nakakoshi|first8=Masamichi|last9=Tsubuki|first9=Masayoshi|last10=Tani|first10=Hidenori|last11=Tanaka|first11=Junichi|date=2012|title=Inhibition of Hepatitis C Virus NS3 Helicase by Manoalide|journal=Journal of Natural Products|volume=75|issue=4|pages=650–4|doi=10.1021/np200883s|pmid=22394195}}</ref> research.

==References==

{{reflist}}

[[Category:Calcium channel blockers]]

[[Category:Furanones]]

[[Category:Secondary alcohols]]

[[Category:Cyclohexenes]]