Harzialactone A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03742 |
| CAS | 321868-49-9 |
| Molecular Weight | 192.21 |
| Molecular Formula | C11H12O3 |
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Description
It is produced by the strain of Trichoderma harzianum OUPS-N115. Harzialacton A has weak cytotoxicity to P388 leukemia cells with ED50 of > 100 μg/mL.
Specification
| Synonyms | (3S,5S)-5-benzyl-3-hydroxydihydrofuran-2(3H)-one; 3-hydroxy-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one; (-)-harzialactone A; (-)-(2S,4S)-harzialactone A |
| IUPAC Name | (3S,5S)-5-benzyl-3-hydroxyoxolan-2-one |
| Canonical SMILES | C1C(OC(=O)C1O)CC2=CC=CC=C2 |
| InChI | InChI=1S/C11H12O3/c12-10-7-9(14-11(10)13)6-8-4-2-1-3-5-8/h1-5,9-10,12H,6-7H2/t9-,10-/m0/s1 |
| InChI Key | QDWGWZDQSRYLTG-UWVGGRQHSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 360.1±17.0°C at 760 mmHg |
| Melting Point | 52-84°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Two new compounds from the marine Nigrospora sphaerica
Qi-Hui Zhang, Li Tian, Lian-Di Zhou, Ying Zhang, Zhi-Feng Li, Hui-Ming Hua, Yue-Hu Pei J Asian Nat Prod Res. 2009 Nov;11(11):962-6. doi: 10.1080/10286020903339614.
Two new compounds, 1-(5-oxotetrahydrofuran-2-yl)ethyl 2-phenylacetate (1) and 3-hydroxybutan-2-yl 2-hydroxy-3-phenylpropanoate (2), along with three known compounds, harzialactone A (3), benzeneethanol 4-hydroxy-1-acetate (4), and 1,4-dioxane-2,5-dione-3,6-bis(penylmethyl)-homopolymer (5), have been isolated from the fungus Nigrospora sphaerica. Their structures were determined on the basis of chemical and spectroscopic methods.
2. Evaluation of antileishmanial activity of harzialactone a isolated from the marine-derived fungus Paecilomyces sp
Glaucia H Braun, Henrique P Ramos, Ana C B B Candido, Rita C N Pedroso, Kátia A Siqueira, Marcos A Soares, Gustavo M Dias, Lizandra G Magalhães, Sérgio R Ambrósio, Ana H Januário, Rosemeire C L R Pietro Nat Prod Res. 2021 May;35(10):1644-1647. doi: 10.1080/14786419.2019.1619725. Epub 2019 May 29.
Fractionation of extracts from the culture broth of the marine-derived fungus, Paecilomyces sp. 7A22, resulted in the isolation of the harzialactone A (HA), a known compound previously isolated from fungi of marine environments. The chemical structure of HA was determined by spectroscopic analyses. Upon evaluation of HA on antileishmanial assays against Leishmania amazonensis, HA exhibited significant activity against promastigotes forms with IC50 of 5.25 µg mL-1 and moderate activity against intracellular amastigotes with IC50 of 18.18 µg mL-1. This is the first report on the antileishmanial activity of HA, and the effects of HA presented in this work suggest that this class of compounds are suitable for future biological in vitro and in vivo studies for the search of natural products with activity against Leishmania spp. Furthermore, the present results corroborate marine-derived fungi as a promising source of natural products with antiparasitic activity.
3. Synthesis of (3R,5R)-harzialactone A and its (3R,5S)-isomer
Gowravaram Sabitha, Rangavajjula Srinivas, Sukant K Das, Jhillu S Yadav Beilstein J Org Chem. 2010 Jan 29;6:8. doi: 10.3762/bjoc.6.8.
The total synthesis of (3R,5R)-harzialactone A (1) and its (3R,5S)-isomer (2) is described. Epoxide opening with thioacetal and diastereoselective reductions are used as key reactions.
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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 ╳
