Ternatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04302 |
| CAS | 148619-41-4 |
| Molecular Weight | 737.97 |
| Molecular Formula | C37H67N7O8 |
| Purity | >98% by HPLC |
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Description
It is a cyclic peptide antifungal metabolite first isolated from the fungus didymocladium ternatum. It is a potent inhibitor of fat accumulation in 3T3-L1 murine adipocytes.
Specification
| Synonyms | cyclo[N-methyl-L-alanyl-N-methyl-D-alanyl-(3R)-3-hydroxy-D-leucyl-D-alloisoleucyl-N-methyl-L-alanyl-N-methyl-L-leucyl-L-leucyl]; 1,4,7,10,13,16,19-Heptaazacycloheneicosane; (-)-Ternatin; cyclo[DL-N(Me)Ala-DL-N(Me)Ala-DL-Leu(3-OH)-DL-xiIle-DL-N(Me)Ala-DL-N(Me)Leu-DL-Leu] |
| Storage | Store at -20°C |
| IUPAC Name | (3S,6S,9S,12S,15R,18R,21R)-15-[(2S)-butan-2-yl]-18-[(1R)-1-hydroxy-2-methylpropyl]-1,3,4,10,12,13,21-heptamethyl-6,9-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptazacyclohenicosane-2,5,8,11,14,17,20-heptone |
| Canonical SMILES | CCC(C)C1C(=O)N(C(C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)NC(C(=O)N1)C(C(C)C)O)C)C)C)C)CC(C)C)CC(C)C)C)C)C |
| InChI | InChI=1S/C37H67N7O8/c1-16-22(8)28-37(52)43(14)25(11)35(50)44(15)27(18-20(4)5)32(47)38-26(17-19(2)3)36(51)42(13)24(10)34(49)41(12)23(9)31(46)40-29(33(48)39-28)30(45)21(6)7/h19-30,45H,16-18H2,1-15H3,(H,38,47)(H,39,48)(H,40,46)/t22-,23+,24-,25-,26-,27-,28+,29+,30+/m0/s1 |
| InChI Key | ZMFVAIFXJWEOMH-PTPSPKLBSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 985.4±65.0°C (Predicted) |
| Density | 1.028±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. (-)-Ternatin inhibits adipogenesis and lipid metabolism in 3T3-L1 cells
Hidefumi Kitazawa, Junko Ito, Kenichiro Shimokawa, Takehiro Fukami, Shigeru Tokita, Akio Kanatani, Kaoru Yamada, Daisuke Uemura, Ken Shimamura, Masahiko Ito Peptides . 2009 Jun;30(6):1074-81. doi: 10.1016/j.peptides.2009.02.008.
(-)-Ternatin, a highly N-methylated cyclic peptide, inhibits fat accumulation in 3T3-L1 cells and reduces fat mass in mice. However, the mechanism for its anti-adipogenic effect has remained unknown. To examine the mechanism used by (-)-ternatin to inhibit adipocyte differentiation, we examined the effects of (-)-ternatin and [l-Ala(4)]ternatin, an inactive analog of (-)-ternatin, on the expression of adipocyte markers and lipogenic enzymes. We found that (-)-ternatin potently reduced mRNA expression of several adipocyte markers in a dose-dependent manner, whereas [l-Ala(4)]ternatin showed no effects. At the immediate early phase, (-)-ternatin, but not [l-Ala(4)]ternatin, reduced the expression of Srebp1c, Fas, Acc2 and C/EBP-alpha while showing no effects on C/EBP-beta and C/EBP-delta. These results suggest that (-)-ternatin affects the mid-to late differentiation stages of adipocytes. Consistent with the decreased expression of lipogenic enzymes, (-)-ternatin potently inhibited triglyceride synthesis. Intriguingly, (-)-ternatin also inhibited triglyceride synthesis in rat primary hepatocytes, suggesting that the potential action sites for (-)-ternatin are shared by adipocytes and liver. Although the target molecule of (-)-ternatin remains unknown, our data suggest that (-)-ternatin and its potential target might provide a new therapeutic approach to metabolic disorders.
2. Ternatin, a cyclic peptide isolated from mushroom, and its derivative suppress hyperglycemia and hepatic fatty acid synthesis in spontaneously diabetic KK-A(y) mice
Hiroyuki Ito, Haruna Kawashima, Atsushi Murai, Kumiko Takemori, Misato Kobayashi, Daisuke Uemura, Kaoru Yamada, Fumihiko Horio, Shun Masuda Biochem Biophys Res Commun . 2012 Oct 19;427(2):299-304. doi: 10.1016/j.bbrc.2012.09.045.
(-)-Ternatin is a highly methylated cyclic heptapeptide isolated from mushroom Coriolus versicolor. Ternatin has an inhibitory effect on fat accumulation in 3T3-L1 adipocytes. [D-Leu(7)]ternatin, a ternatin derivative, also inhibited fat accumulation in 3T3-L1 cells, although the effectiveness of [D-Leu(7)]ternatin was lower than that of ternatin. In this study, we investigated the effects of ternatin and [D-Leu(7)]ternatin on obesity and type 2 diabetes in KK-A(y) mice, an animal model for spontaneously developed type 2 diabetes. We continuously administered ternatin (8.5 or 17 nmol/day) or [D-Leu(7)]ternatin (68 nmol/day) to mice via a subcutaneous osmotic pump. Unexpectedly, neither ternatin nor [D-Leu(7)]ternatin affected body weight or adipose tissue weight in KK-A(y) mice. In contrast, it was demonstrated that both ternatin and [D-Leu(7)]ternatin suppress the development of hyperglycemia. In liver, the SREBP-1c mRNA level tended to be lower or significantly decreased in mice treated with ternatin or [D-Leu(7)]ternatin, respectively. Moreover, we found that ternatin directly lowered the SREBP-1c mRNA level in Hepa1-6 hepatocyte cells. This study showed that ternatin and [D-Leu(7)]ternatin each had a preventive effect on hyperglycemia and a suppressive effect on fatty acid synthesis in KK-A(y) mice.
3. Ternatin, an anti-inflammatory flavonoid, inhibits thioglycolate-elicited rat peritoneal neutrophil accumulation and LPS-activated nitric oxide production in murine macrophages
M F Souza, R A Ribeiro, M J Teixeira, E R Silveira, V S N Rao, A R Campos, L A F Paiva, G A C Brito Planta Med . 2003 Sep;69(9):851-3. doi: 10.1055/s-2003-43213.
Ternatin, an anti-inflammatory flavonoid from Egletes viscosa Less., was examined for its possible influence on thioglycolate-elicited neutrophil influx into the rat peritoneal cavity in vivo and nitric oxide production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages ex vivo. The neutrophil influx induced by thioglycolate was found to be significantly lower in ternatin (25 and 50 mg/kg, s. c.) pre-treated rats with a similar magnitude of inhibition produced by dexamethasone (1 mg/kg, s. c.), a known anti-inflammatory agent. Also, peritoneal macrophages from ternatin (25 mg/kg)-treated mice that were exposed to LPS demonstrated significantly less production of nitric oxide (NO). These results suggest that ternatin exerts its anti-inflammatory action, at least in part, through inhibition of neutrophil migration and modulation of macrophage function.
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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 ╳
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