Protostemonine

Names

[ Name ]:
Protostemonine

[Synonym ]:
(5Z)-4-Methoxy-3-methyl-5-{(1S,3aR,8S,10aS,10bR)-1-methyl-8-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene}furan-2(5H)-one
(Z)-4-methoxy-3-methyl-5-((1S,3aR,8S,10aS,10bR)-1-methyl-8-((2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)octahydro-1H-furo[3,2-c]pyrrolo[1,2-a]azepin-2(10bH)-ylidene)furan-2(5H)-one
Prostemonin
4-Methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydro-[2r]furyl)-(3ar,10at,10bt)-decahydro-furo[3,2-c]pyrrolo[1,2-a]azepin-2-yliden]-5H-furan-2-on
Protostemonin
4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydrofuran-2r-yl)-(3ar,10at,10bt)-decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one
2(3H)-Furanone, 5-[(1S,2Z,3aR,8S,10aS,10bR)-decahydro-2-(3-methoxy-4-methyl-5-oxo-2(5H)-furanylidene)-1-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8-yl]dihydro-3-methyl-, (3S,5S)-
QCR-280
(5Z)-4-Methoxy-3-methyl-5-{(1S,3aR,8S,10aS,10bR)-1-methyl-8-[(2S,4S)-4-methyl-5-oxotetrahydro-2-furanyl]decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene}-2(5H)-furanone
4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydro-[2r]furyl)-(3ar,10at,10bt)-decahydro-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one
4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydro-furan-2r-yl)-(3ar,10at,10bt)-decahydro-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one

Biological Activity

[Description]:

Protostemonine is an active alkaloid mainly isolated from the roots of Stemona sesslifolia, with anti-inflammatory activity. Protostemonine has anti-inflammatory effects on asthma and gram-negative bacteria-induced acute lung injury[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[References]

[1]. Wu Y, et al. Protostemonine alleviates heat-killed methicillin-resistant Staphylococcus aureus-induced acute lung injury through MAPK and NF-κB signaling pathways. Int Immunopharmacol. 2019 Dec;77:105964.

[2]. Wu YX, et al. Protostemonine effectively attenuates lipopolysaccharide-induced acute lung injury in mice. Acta Pharmacol Sin. 2018 Jan;39(1):85-96.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
594.1±50.0 °C at 760 mmHg

[ Melting Point ]:
172°C (lit.)

[ Molecular Formula ]:
C₂₃H₃₁NO₆

[ Molecular Weight ]:
417.495

[ Flash Point ]:
313.1±30.1 °C

[ Exact Mass ]:
417.215149

[ PSA ]:
74.30000

[ LogP ]:
2.60

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.576