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Neotuberostemonine

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Neotuberostemonine Basic information

Product Name:
Neotuberostemonine
Synonyms:
  • Neotuberostemonine
  • Furo[2,3-h]pyrrolo[3,2,1-jk][1]benzazepin-10(2H)-one,8-ethyldodecahydro-11-methyl-2-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-,(2S,7aR,8R,8aR,11S,11aR,11bS,11cR)-
  • (2S,7aR,8R,8aR,11S,11aR,11bS,11cR)-8-Ethyl-11-methyl-2-[(2S,4S)-4 -methyl-5-oxotetrahydro-2-furanyl]dodecahydroazepino[3,2,1-hi]fur o[3,2-e]indol-10(2H)-one
  • (2S,31R,7aR,8R,8aR,11S,11aR,11bS)-8-Ethyl-11-methyl-2-((2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)dodecahydroazepino[3,2,1-hi]furo[3,2-e]indol-10(2H)-one
  • Neotuberostemonine, 10 mM in DMSO
CAS:
143120-46-1
MF:
C22H33NO4
MW:
375.5
EINECS:
200-158-5
Mol File:
143120-46-1.mol
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Neotuberostemonine Chemical Properties

Boiling point:
554.2±50.0 °C(Predicted)
Density 
1.19±0.1 g/cm3(Predicted)
solubility 
DMSO: 10 mM
form 
A crystalline solid
pka
8.90±0.70(Predicted)
color 
White to off-white
InChIKey
GYOGHROCTSEKDY-UEIGSNQUSA-N
SMILES
N12[C@H]([C@@H]3C[C@H](C)C(=O)O3)C[C@]3([H])[C@@]1([H])[C@@]([H])([C@@H](CC)[C@@]1([H])OC(=O)[C@@H](C)[C@@]31[H])CCCC2
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Neotuberostemonine Usage And Synthesis

Description

Neotuberostemonine (NTS) is one of the main antitussive alkaloids in the root of Stemona tuberosa Lour, it has a significant protective effect on bleomycin (BLM)-induced pulmonary fibrosis through suppressing the recruitment and M2 polarization of macrophages. Neotuberostemonine demonstrates antitussive properties in guinea pigs.

Chemical Properties

It is soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from Stemona japonica.

Uses

Neotuberostemonine is a major bioactive alkaloid of Stemona tuberosa. It can also be used to treat pulmonary fibrosis.

Definition

ChEBI: Neotuberostemonine is an alkaloid. It has a role as a metabolite.

Biological Functions

Neotuberostemonine is an alkaloid originally isolated from S. tuberosa that has diverse biological activities. It inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) protein levels and NO production in RAW 264.7 cells when used at a concentration of 100 μM. Neotuberostemonine (50 μM) inhibits RANKL-induced osteoclast differentiation of RAW 264.7 cells. It reduces the citric acid-induced cough reflex in conscious guinea pigs when administered at a dose of 133 μmol/kg. Neotuberostemonine (40 mg/kg) inhibits pulmonary collagen deposition and fibrosis, as well as bronchoalveolar lavage fluid (BALF) monocyte and lymphocyte infiltration in a mouse model of bleomycin-induced pulmonary fibrosis.

Biological Activity

Neotuberostemonine, one of the main antitussive alkaloids in the root of Stemona tuberosa Lour, attenuates bleomycin-induced pulmonary fibrosis by suppressing the recruitment and activation of macrophages.

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