| Identification | Back Directory | [Name]
laurotetanine | [CAS]
128-76-7 | [Synonyms]
Litsoeine
NSC106610
NSC-106610
NSC 106610
Laurotetanin
laurotetanine
(6aS)-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-4H-dibenzo[de,g]quinolin-9-ol
[S,(+)]-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-4H-dibenzo[de,g]quinolin-9-ol | [Molecular Formula]
C19H21NO4 | [MDL Number]
MFCD01711527 | [MOL File]
128-76-7.mol | [Molecular Weight]
327.37 |
| Chemical Properties | Back Directory | [Melting point ]
125°C | [Boiling point ]
465.27°C (rough estimate) | [density ]
1.2223 (rough estimate) | [refractive index ]
1.5000 (estimate) | [pka]
9.76±0.20(Predicted) |
| Hazard Information | Back Directory | [Description]
The noraporphine alkaloid was first isolated by Greshoff from Litsea chrysocorna
and subsequently from other species of Lauraceae including L. citrata and L.
cubeba. When freshly crystallized from Me2 CO it yields colourless crystals but
these become yellow in air. The alkaloid behaves as a phenolic base giving salts
with mineral acids which all contain H20 of crystallization. The picrate monohydrate has m.p. 1480 C, the dibenzoyl derivative, m.p. 169-1700 C and the
phenylthiocarbamide, m.p. 211-2°C. Three methoxyl groups, an imino group
and a phenolic hydroxyl group are present, the latter giving the O-methyl ether
which is an amorphous powder but yields a crystalline hydrochloride, m.p.
245°C; an oxalate, m.p. 233°C and the thiocarbamide, m.p. 154-5°C. The Nmethyl derivative (q.v.) is found naturally in Peurnus boldus and the O,Ndimethyl derivative is glaucine. The structure has been determined from chemical
degradation and synthesis. | [Uses]
Laurotetanine ((+)-Laurotetanine) is an potent and orally active isoquinoline alkaloid and could be extracted from the roots of Litsea cubeba (Lour.) Pers. Laurotetanine exerts an anti-asthmatic effect by inhibition of IgE, histamine, and inflammatory reactions via down-regulating MUC5AC and NF-κB signaling pathways[1]. | [Definition]
ChEBI:Litsoeine is an isoquinoline alkaloid. | [in vivo]
Laurotetanine ((+)-Laurotetanine; 20-60 mg/kg; p.o.; daily, for 21 d; Sprague Dawley (SD) rats) has anti-asthmatic effect in rats by down-regulating MUC5AC and NF-κB signaling pathways[1]. | Animal Model: | Sprague Dawley (SD) rats (180-220g) [1] | | Dosage: | 20, 40, and 60 mg/kg | | Administration: | Oral administration; daily, for 21 days | | Result: | Reduced inflammatory cells, including eosinophils, neutrophils, lymphocytes, and macrophages.
Decreased inflammatory cytokines viz IL-4, IL-6, IL-13 and increased IFN-γ.
Reduced serum IgE and histamine.
Decreased MUC5AC expression and increased NF-κB and IκB expression in lung tissues.
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| [References]
Greshoff., Ber., 23,3537 (1890)
Filippo., Arch. Pharm., 236, 601 (1898)
Gorter., Bull. Jard. bot. Buitenzorg., 3, 180 (1921)
Barger, Silberschmidt.,J. Chem. Soc., 2919 (1928)
Barger et al., Ber., 66, 450 (1933)
Ruegger., Helv. Chim. Acta, 42,754 (1959)
Kikkawa.,J. Pharm. Soc., Japan, 79,83,425 (1959) |
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