Quinocitrinine B
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| Category | Bioactive by-products |
| Catalog number | BBF-02162 |
| CAS | |
| Molecular Weight | 271.33 |
| Molecular Formula | C16H19N2O2 |
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Description
Quinocitrinine B is produced by the strain of Penicillum citrinum Thom 1910. It has moderate anti-gram positive and negative bacterial and fungal activity. And it also shows moderate antiproliferative activity to L-929, K-562 and HeLa cells.
Specification
| Synonyms | (3R)-3-[(1S)-1-Methylpropyl]-4-methyl-6-hydroxy-4-azonia-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline-1-one |
| IUPAC Name | (3R)-3-[(2S)-butan-2-yl]-6-hydroxy-4-methyl-2,3-dihydropyrrolo[3,4-b]quinolin-4-ium-1-one |
| Canonical SMILES | CCC(C)C1C2=C(C=C3C=CC(=CC3=[N+]2C)O)C(=O)N1 |
| InChI | InChI=1S/C16H18N2O2/c1-4-9(2)14-15-12(16(20)17-14)7-10-5-6-11(19)8-13(10)18(15)3/h5-9,14H,4H2,1-3H3,(H,17,20)/p+1/t9-,14+/m0/s1 |
| InChI Key | GTNBOKIWQUJZFH-LKFCYVNXSA-O |
Properties
| Appearance | Light Brown Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor); fungi |
| Melting Point | 152-153°C |
Reference Reading
1. [New producers of biologically active compounds--fungal strains of the genus Penicillium isolated from permafrost]
T V Antipova, V P Zhelifonova, B P Baskunov, S M Ozerskaia, N E Ivanushkina, A G Kozlovskiĭ Prikl Biokhim Mikrobiol. 2011 May-Jun;47(3):318-23.
Screening of producers of secondary metabolites was carried out among 25 fungal strains of Penicillium genus isolated from permafrost in Arctic and Antarctic regions and Kamchatka. Nearly 50% of the investigated strains synthesize biologically active substances of alkaloid nature: ergot alkaloids, diketopiperazines, and quinoline derivatives. A large group of the identified metabolites belongs to mycotoxins. A strain of Penicillium waksmanii was found producing epoxiagroclavine-I and quinocitrinins. The main physiological and biochemical characteristics of this producer were investigated.
2. [Effect of quinocitrinines from the fungus Penicillium citrinum on the respiration of yeasts and bacteria]
A Iu Arinbasarova, A G Medentsev, A G Kozlovskiĭ Prikl Biokhim Mikrobiol. 2007 Nov-Dec;43(6):701-4.
We studied the effect of quinocitrinines on the respiratory activity of yeasts (Yarrowia lipolytica) and bacteria (Arthrobacter globiformis). Quinocitrinines were shown to activate respiration of native cells in both types of organisms. Studies of yeast mitochondria showed that quinocitrinine exerts an uncoupling effect on oxidative phosphorylation, which activates the respiration, reduces the respiratory control, and decreases the ADP/O ratio. Experiments with intact mitochondria and native cells of Arthrobacter globiformis revealed that quinocitrinine decreases the membrane potential. The uncoupling effect likely constitutes a mechanism of the antibiotic activity of quinocitrinines.
3. [Physiological and biochemical characteristics of fungi of the genus Penicillium as producers of ergot alkaloids and quinocitrinins]
A G Kozlovskiĭ, V P Zhelifonova, T V Antipova, N F Zelenkova Prikl Biokhim Mikrobiol. 2011 Jul-Aug;47(4):469-73.
Four cultures of fungi of the genus Penicillium belonging to Furcatum Pitt subgenus, such as P. citrinum Thom, 1910; P. corylophilum Dierckx, 1901; P. fellutanum Biourge, 1923; and P. waksmanii Zaleski, 1927, produced the ergot alkaloids, namely, agroclavine-I, and epoxyagroclavine-I; their N-N-dimers, such as dimer of epoxyagroclavine-I and the mixed dimer of epoxyagroclavine-I and agroclavine-I; and also quinoline metabolites, namely, quinocitrinin A and quinocitrinin B. Physiological and biochemical characteristics of the producers were studied. Optimal conditions for the biosynthesis of metabolome components were determined. Zinc additive to the medium stimulated the biosynthesis of the ergot alkaloids in all cases; citrinin production was increased only in P. citrinum, and that was suppressed in P. corylophinum, P. fellutanum, and P. waksmanii. This testifies that genes of the biosynthesis pathways are located in the different clusters of the producers.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
