Fleephilone

Name: Fleephilone
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Category	Antibiotics
Catalog number	BBF-00941
CAS	183239-76-1
Molecular Weight	441.47
Molecular Formula	C24H27NO7

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Fleephilone is an antibiotic produced by Trichoderma harzianum. It has the combination of inhibiting viral particle regulation (REV) protein and [33P] labeled viral particle regulatory response element (RRE) RNA, with IC50 of 7.6 mol/L.

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Synonyms	(2aR,3S,10cR)-3-hydroxy-8-methyl-7,9-dioxo-1-[(1E,3E)-penta-1,3-dien-1-yl]-2a,4,5,8,9,10c-hexahydro-3H,7H-2-oxa-5a-azaaceanthrylen-8-yl 3-hydroxybutanoate
IUPAC Name	[(12S,13R,16R)-12-hydroxy-5-methyl-4,6-dioxo-15-[(1E,3E)-penta-1,3-dienyl]-14-oxa-9-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,7-trien-5-yl] 3-hydroxybutanoate
Canonical SMILES	CC=CC=CC1=C2C3C(O1)C(CCN3C=C4C2=CC(=O)C(C4=O)(C)OC(=O)CC(C)O)O
InChI	InChI=1S/C24H27NO7/c1-4-5-6-7-17-20-14-11-18(28)24(3,32-19(29)10-13(2)26)23(30)15(14)12-25-9-8-16(27)22(31-17)21(20)25/h4-7,11-13,16,21-22,26-27H,8-10H2,1-3H3/b5-4+,7-6+/t13?,16-,21+,22-,24?/m0/s1
InChI Key	UOPRBHLVKJBASE-XVSBCJMYSA-N

Appearance	Yellow Powder
Antibiotic Activity Spectrum	viruses
Boiling Point	707.6°C at 760 mmHg
Density	1.35 g/cm3

1. Harziphilone and fleephilone, two new HIV REV/RRE binding inhibitors produced by Trichoderma harzianum

J Qian-Cutrone, S Huang, L P Chang, D M Pirnik, S E Klohr, R A Dalterio, R Hugill, S Lowe, M Alam, K F Kadow J Antibiot (Tokyo). 1996 Oct;49(10):990-7. doi: 10.7164/antibiotics.49.990.

During the screening of the natural products for their ability to inhibit the binding of REV (regulation of virion expression) protein to [33P] labeled RRE (REV responsive element) RNA, two novel fungal metabolites, harziphilone and fleephilone, were isolated from the butanol-methanol (1:1) extract of the fermentation broth of Trichoderma harzianum by bioassay guided fractionation. The structures of these two new compounds were established by spectroscopic methods. Harziphilone and fleephilone showed inhibitory activity against the binding of REV-protein to RRE RNA with IC50 values of 2.0 microM and 7.6 microM, respectively. However both compounds did not protect CEM-SS cells from acute HIV infection at concentration levels up to 200 micrograms/ml using an XTT dye reduction assay. In addition, harziphilone demonstrated cytotoxicity at 38 microM against the murine tumor cell line M-109.

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