Hypnophilin
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| Category | Antibiotics |
| Catalog number | BBF-01493 |
| CAS | 80677-96-9 |
| Molecular Weight | 248.32 |
| Molecular Formula | C15H20O3 |
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Description
Hypnophilin is produced by the strain of Pleurotellus hypnophilus 539. It has a variety of activities, including anti-gram-positive bacteria, negative bacteria, yeast, mold and tumor activities.
Specification
| Synonyms | (-)-Hypnophilin; (3aR,3bβ,6aβ)-4β-Hydroxy-3aα,5,5-trimethyl-3-methylene-1α,7aα-epoxydecahydro-2H-cyclopenta[a]pentalene-2-one |
| IUPAC Name | (1S,3R,6R,7R,8R,11S)-6-hydroxy-5,5,8-trimethyl-9-methylidene-12-oxatetracyclo[6.4.0.01,11.03,7]dodecan-10-one |
| Canonical SMILES | CC1(CC2CC34C(O3)C(=O)C(=C)C4(C2C1O)C)C |
| InChI | InChI=1S/C15H20O3/c1-7-10(16)12-15(18-12)6-8-5-13(2,3)11(17)9(8)14(7,15)4/h8-9,11-12,17H,1,5-6H2,2-4H3/t8-,9+,11-,12-,14+,15-/m1/s1 |
| InChI Key | FBSAMOXBBLSEEW-ZYHYCFKLSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; yeast; neoplastics (Tumor) |
Reference Reading
1. In vitro activity of hypnophilin from Lentinus strigosus: a potential prototype for Chagas disease and leishmaniasis chemotherapy
E M Souza-Fagundes, B B Cota, L H Rosa, A J Romanha, R Corrêa-Oliveira, C A Rosa, C L Zani, A Teixeira-Carvalho, O A Martins-Filho Braz J Med Biol Res. 2010 Nov;43(11):1054-61. doi: 10.1590/s0100-879x2010007500108. Epub 2010 Oct 14.
Hypnophilin and panepoxydone, terpenoids isolated from Lentinus strigosus, have significant inhibitory activity on Trypanosoma cruzi trypanothione reductase (TR). Although they have similar TR inhibitory activity at 10 μg/mL (40.3 μM and 47.6 μM for hypnophilin and panepoxydone, respectively; ~100%), hypnophilin has a slightly greater inhibitory activity (~71%) on T. cruzi amastigote (AMA) growth in vitro as well as on in vitro phytohemagglutinin (PHA)-induced peripheral blood mononuclear (PBMC) proliferation (~70%) compared to panepoxydone (69% AMA inhibition and 91% PBMC inhibition). Hypnophilin and panepoxydone at 1.25 μg/mL had 67% inhibitory activity onLeishmania (Leishmania) amazonensis amastigote-like (AMA-like) growth in vitro. The panepoxydone activity was accompanied by a significant inhibitory effect on PHA-induced PBMC proliferation, suggesting a cytotoxic action. Moreover, incubation of human PBMC with panepoxydone reduced the percentage of CD16(+) and CD14(+) cells and down-regulated CD19(+), CD4(+) and CD8(+) cells, while hypnophilin did not alter any of the phenotypes analyzed. These data indicate that hypnophilin may be considered to be a prototype for the design of drugs for the chemotherapy of diseases caused by Trypanosomatidae.
2. Transition-metal-catalyzed cycloadditions for the synthesis of eight-membered carbocycles
Zhi-Xiang Yu, Yi Wang, Yuanyuan Wang Chem Asian J. 2010 May 3;5(5):1072-88. doi: 10.1002/asia.200900712.
Eight-membered carbocycles are found in a wide variety of natural products that exhibit a broad range of biological and medicinal activities (cf. the most potent anticancer drug, taxol). However, the synthesis of eight-membered carbocycles is quite challenging as traditional approaches are met with entropic and enthalpic penalties in the ring-forming transition states. These negative effects can be totally or partially avoided with the implementation of transition-metal-catalyzed/mediated cycloadditions. In this Focus Review, examples of elegant and efficient metal-catalyzed and some metal-mediated cycloadditions (including Ni- catalyzed [4+4] and Rh-catalyzed [4+2+2] and [5+2+1] reactions) are presented to illustrate this. Application of these cycloaddition reactions in total synthesis is also presented to show the significance of these reactions in addressing challenges in natural product synthesis.
3. The cytotoxic and proapoptotic activities of hypnophilin are associated with calcium signaling in UACC-62 cells
Mauro C X Pinto, Betania B Cota, Michele A Rodrigues, Maria F Leite, Elaine M de Souza-Fagundes J Biochem Mol Toxicol. 2013 Nov;27(11):479-85. doi: 10.1002/jbt.21507. Epub 2013 Jul 18.
Hypnophilin (HNP) is a sesquiterpene that is isolated from Lentinus cf. strigosus and has cytotoxic activities. Here, we studied the calcium signaling and cytotoxic effects of HNP in UACC-62 cells, a human skin melanoma cell line. HNP was able to increase the intracellular calcium concentration in UACC-62 cells, which was blocked in cells stimulated in Ca(2+) -free media. HNP treatment with BAPTA-AM, an intracellular Ca(2+) chelator, caused an increase in calcium signals. HNP showed cytotoxicity against UACC-62 cells in which it induced DNA fragmentation and morphological alterations, including changes in the nuclear chromatin profile and increased cytoplasmatic vacuolization, but it had no effect on the plasma membrane integrity. These data suggest that cytotoxicity in UACC-62 cells, after treatment with HNP, is associated with Ca(2+) influx. Together, these findings suggest that HNP is a relevant tool for the further investigation of new anticancer approaches.
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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 ╳
