Harziphilone

Harziphilone

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Category Antibiotics
Catalog number BBF-01323
CAS 183239-75-0
Molecular Weight 262.30
Molecular Formula C15H18O4

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Description

It is produced by the strain of Trichoderma harzianum. It has weak anti-gram-positive bacterial activity and anti-tumor effect, it can inhibit lymphoblastic leukemia L1210 and leukemia P388 with IC50 of 0.26 μg/mL. It inhibits the binding of viral particle regulatory (REV) proteins to [33P] labeled viral particle regulatory effector element (RRE) RNA, IC50 is 2.0 μmol/L. 200 μg/mL of Harziphilone does not protect CEM-SS cells from HIV-1 infection, and 38μmol/L of Harziphilone has cytotoxicity to mouse tumor cells M-109.

Specification

Synonyms rel-(6R,7R)-6,7-dihydroxy-7-methyl-3-[(1E,3E)-penta-1,3-dien-1-yl]-1,5,6,7-tetrahydro-8H-isochromen-8-one; (+)-Harziphilone; 8H-2-Benzopyran-8-one,1,5,6,7-tetrahydro-6,7-dihydroxy-7-methyl-3-(1E,3E)-1,3-pentadienyl-, (6R,7R)-rel-
IUPAC Name (6R,7R)-6,7-dihydroxy-7-methyl-3-[(1E,3E)-penta-1,3-dienyl]-5,6-dihydro-1H-isochromen-8-one
Canonical SMILES CC=CC=CC1=CC2=C(CO1)C(=O)C(C(C2)O)(C)O
InChI InChI=1S/C15H18O4/c1-3-4-5-6-11-7-10-8-13(16)15(2,18)14(17)12(10)9-19-11/h3-7,13,16,18H,8-9H2,1-2H3/b4-3+,6-5+/t13-,15-/m1/s1
InChI Key GFTDIFRKHSPLIX-VNLWOOSYSA-N

Properties

Appearance Orange Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor); Viruses
Boiling Point 473.4 °C at 760 mmHg
Density 1.24 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone
Lucy M Stark, Klaus Pekari, Erik J Sorensen Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12064-6. doi: 10.1073/pnas.0402563101. Epub 2004 Jul 1.
Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.
2. 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.

Bio Calculators

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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