Arohynapene B

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Category Antibiotics
Catalog number BBF-00092
CAS 154445-09-7
Molecular Weight 286.36
Molecular Formula C18H22O3

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Description

Arohynapene B is an anti-coccidial antibiotic produced by Pemcillum sp. FO-2295. It has no antibacterial activity.

Specification

Synonyms 5-(2-Hydroxymethyl-6,8-dimethyl-5,6,7,8-tetrahydronaphthalene)-2,4-pentadienoic acid; 2,4-Pentadienoic acid, 5-(5,6,7,8-tetrahydro-2-(hydroxymethyl)-6,8-dimethyl-1-naphthalenyl)-
IUPAC Name (2E,4E)-5-[2-(hydroxymethyl)-6,8-dimethyl-5,6,7,8-tetrahydronaphthalen-1-yl]penta-2,4-dienoic acid
Canonical SMILES CC1CC(C2=C(C1)C=CC(=C2C=CC=CC(=O)O)CO)C
InChI InChI=1S/C18H22O3/c1-12-9-13(2)18-14(10-12)7-8-15(11-19)16(18)5-3-4-6-17(20)21/h3-8,12-13,19H,9-11H2,1-2H3,(H,20,21)/b5-3+,6-4+
InChI Key XVNDJROXVPBPBY-GGWOSOGESA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum parasites
Boiling Point 494.2°C at 760 mmHg
Density 1.135 g/cm3

Reference Reading

1. 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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