Manoalide

Names

[ Name ]:
Manoalide

[Synonym ]:
Manoalide
MFCD00153826
(5R)-5-Hydroxy-4-{(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexen-1-yl]-3,6-dihydro-2H-pyran-2-yl}-2(5H)-furanone
2(5H)-Furanone, 4-[(2R,6R)-3,6-dihydro-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexen-1-yl]-2H-pyran-2-yl]-5-hydroxy-, (5R)-
(2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one

Biological Activity

[Description]:

Manoalide is a potent Phospholipase A2 (PLA2) and Phospholipase C (PLC) inhibitor. Manoalide, a sesterpenoid compound, displays anti-inflammatory and antibacterial activities[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

PLA2

PLC

[In Vitro]

Manoalide (0.05 μM) impaires IL-7-induced entry of the B cell progenitors into S and G2/M phases and increases the population of apoptotic cells in IL-7-cultured B cell progenitors. In addition, Manoalide reduced IL-7-induced phosphorylation of S6 compared to the control without inhibitor pre-treatment[1].

[In Vivo]

Manoalide reverses venom preconditioning (VPC)-induced anti-inflammatory effects 24 h after surgical brain injury (SBI) in adult male Sprague-Dawley rats, 260 to 300 g[1].

[References]

[1]. Mei Yu, et al. PLCγ-dependent mTOR signalling controls IL-7-mediated early B cell development. Nat Commun. 2017 Nov 13;8(1):1457.

[2]. Yuechun Wang, et al. Naja sputatrix Venom Preconditioning Attenuates Neuroinflammation in a Rat Model of Surgical Brain Injury via PLA2/5-LOX/LTB4 Cascade Activation. Sci Rep. 2017 Jul 14;7(1):5466.

[3]. Afef Dellai, et al. Anticonvulsant and analgesic activities of crude extract and its fractions of the defensive secretion from the Mediterranean sponge, Spongia officinalis. Cancer Cell Int. 2012 Apr 11;12(1):15.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
609.6±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₃₆O₅

[ Molecular Weight ]:
416.550

[ Flash Point ]:
203.3±25.0 °C

[ Exact Mass ]:
416.256287

[ PSA ]:
75.99000

[ LogP ]:
5.19

[ Vapour Pressure ]:
0.0±4.0 mmHg at 25°C

[ Index of Refraction ]:
1.549

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
20/22

[ Safety Phrases ]:
36

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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