Arohynapene A
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| Category | Antibiotics |
| Catalog number | BBF-00091 |
| CAS | 154445-08-6 |
| Molecular Weight | 286.36 |
| Molecular Formula | C18H22O3 |
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Description
Arohynapene A is an anti-coccidial antibiotic produced by Pemcillum sp. FO-2295. Arohynapene A has no antibacterial activity.
Specification
| Synonyms | 5-(5-Hydroxy-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalene)-2,4-pentadienoic acid; 2,4-Pentadienoic acid, 5-(5,6,7,8-tetrahydro-5-hydroxy-2,6,8-trimethyl-1-naphthalenyl)- |
| IUPAC Name | (2E,4E)-5-(5-hydroxy-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalen-1-yl)penta-2,4-dienoic acid |
| Canonical SMILES | CC1CC(C2=C(C1O)C=CC(=C2C=CC=CC(=O)O)C)C |
| InChI | InChI=1S/C18H22O3/c1-11-8-9-15-17(12(2)10-13(3)18(15)21)14(11)6-4-5-7-16(19)20/h4-9,12-13,18,21H,10H2,1-3H3,(H,19,20)/b6-4+,7-5+ |
| InChI Key | LPDVNGOVYMGORG-YDFGWWAZSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | parasites |
| Boiling Point | 483.3°C at 760 mmHg |
| Density | 1.137 g/cm3 |
Reference Reading
1. Anti-Rhizopus activity of tanzawaic acids produced by the hot spring-derived fungus Penicillium sp. BF-0005
Takehiro Tominaga, Ryuji Uchida, Nobuhiro Koyama, Hiroshi Tomoda J Antibiot (Tokyo). 2018 Jul;71(7):626-632. doi: 10.1038/s41429-018-0049-8. Epub 2018 May 1.
A silkworm infection assay with the pathogenic fungus Rhizopus oryzae was established. Microbial culture broths were screened for anti-Rhizopus antibiotics using this assay. A new compound, tanzawaic acid R was isolated along with known and structurally related tanzawaic acids and arohynapene A from the culture broth of the hot spring-derived fungus Penicillium sp. BF-0005. The structure of tanzawaic acid R was elucidated by various spectroscopic data including 1D and 2D nuclear magnetic resonance spectroscopy. Tanzawaic acids A, B, C, and R and arohynapene A exhibited antifungal activity against R. oryzae. Tanzawaic acids A and B dose-dependently exerted therapeutic effects in the silkworm infection assay with R. oryzae.
2. Arohynapenes A and B, new anticoccidial agents produced by Penicillium sp. Taxonomy, fermentation, and structure elucidation
R Masuma, N Tabata, H Tomoda, K Haneda, Y Iwai, S Omura J Antibiot (Tokyo). 1994 Jan;47(1):46-53. doi: 10.7164/antibiotics.47.46.
Penicillium sp. FO-2295, a water isolate, was found to produce a series of new anticoccidial compounds. Two active compounds, designated arohynapenes A and B, were isolated from the fermentation broth of the producing strain by solvent extration and preparative HPLC. Arohynapene A was deduced to be (2E,4E)-5-(5-hydroxy-2,6,8-trimethyl-5,6,7,8-tetrahydronaphtale ne)-2,4- pentadienoic acid, and arohynapene B was (2E,4E)-5-(2-hydroxymethyl-6,8-dimethyl-5,6,7,8-tetrahydronapht alene)-2,4- pentadienoic acid. Arohynapenes inhibited the growth of Eimeria tenella in an in vitro assay using BHK-21 cells as a host. No schizont in the cells was observed at concentrations ranging above 35.0 microM and 7.0 microM for arohynapenes A and B, respectively.
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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 ╳
