Manoalide

Manoalide is a calcium channel blocker. It has antibiotic, analgesic and anti-inflammatory effects and is found in some sponges, including the West Pacific species Luffariella variabilis.[1] Its functions are made possible by the permanent blockage of phospholipase A2 and C[2] 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. [3] Due to its potential of permanent inhibition, it was made possible for it to take part in oral cancer[4] and Hepatitis C[5] research.

Manoalide
Names
Preferred IUPAC name
(5R)-5-Hydroxy-4-{(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}furan-2(5H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=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 ☒N
    Key: FGJIDQWRRLDGDB-CPIXEKRISA-N ☒N
  • 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
    Key: FGJIDQWRRLDGDB-CPIXEKRIBK
  • 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
Properties
C25H36O5
Molar mass 416.55034
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Brusca, Richard C. and Brusca, Gary J. Invertebrates. 2nd ed. Sinauer Associates, 2002. p. 202.
  2. Oxford dictionary of biochemistry and molecular biology. Cammack, Richard, Ph. D. (Rev. ed.). Oxford: Oxford University Press. 2006. ISBN 978-1-61344-113-8. OCLC 743217704.{{cite book}}: CS1 maint: others (link)
  3. "Molecular Pharmacology: 98 (6)". Molecular Pharmacology. 98 (6). 2020-12-01. ISSN 0026-895X.
  4. Wang, Hui-Ru; Tang, Jen-Yang; Wang, Yen-Yun; Farooqi, Ammad Ahmad; Yen, Ching-Yu; F. Yuan, Shyng-Shiou; Huang, Hurng-Wern; Chang, Hsueh-Wei (2019). "Manoalide Preferentially Provides Antiproliferation of Oral Cancer Cells by Oxidative Stress-Mediated Apoptosis and DNA Damage". Cancers. 11 (9): 1303. doi:10.3390/cancers11091303. PMC 6770486. PMID 31487907.
  5. Salam, Kazi Abdus; Furuta, Atsushi; Noda, Naohiro; Tsuneda, Satoshi; Sekiguchi, Yuji; Yamashita, Atsuya; Moriishi, Kohji; Nakakoshi, Masamichi; Tsubuki, Masayoshi; Tani, Hidenori; Tanaka, Junichi (2012). "Inhibition of Hepatitis C Virus NS3 Helicase by Manoalide". Journal of Natural Products. 75 (4): 650–4. doi:10.1021/np200883s. PMID 22394195.


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