Pulvilloric acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02075 |
| CAS | |
| Molecular Weight | 278.30 |
| Molecular Formula | C15H18O5 |
Online Inquiry
Description
Pulvilloric acid is an antifungal antibiotic produced by Pen. pulvillorum 504.
Specification
| IUPAC Name | (3S)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydroisochromene-7-carboxylic acid |
| Canonical SMILES | CCCCCC1CC2=CC(=O)C(=C(C2=CO1)O)C(=O)O |
| InChI | InChI=1S/C15H18O5/c1-2-3-4-5-10-6-9-7-12(16)13(15(18)19)14(17)11(9)8-20-10/h7-8,10,17H,2-6H2,1H3,(H,18,19)/t10-/m0/s1 |
| InChI Key | KPYJKXACXGIDBE-JTQLQIEISA-N |
Properties
| Appearance | Yellow Needle Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 430.9±45.0°C at 760 mmHg |
| Melting Point | 74-75°C (dec.) |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. New azaphilones and tremulane sesquiterpene from endophytic Nigrospora oryzae cocultured with Irpex lacteus
Qing-Yan Zhou, Xue-Qiong Yang, Zhuo-Xi Zhang, Bang-Yan Wang, Ming Hu, Ya-Bin Yang, Hao Zhou, Zhong-Tao Ding Fitoterapia. 2018 Oct;130:26-30. doi: 10.1016/j.fitote.2018.07.018. Epub 2018 Aug 1.
Five new metabolites belonging to two backbones of pulvilloric acid-type azaphilone and tremulane sesquiterpene were obtained and their structures were determined by spectral analysis. Based on the biogenesis analysis, tremulane sesquiterpenes were obtained from Irpex lacteus by the stimulation of mixed-culture. The antifungal selectivities of metabolites produced by fungus against their co-culture fungus and common pathogens, exhibited competitive interaction of this mix-culture. The tremulane sesquiterpene conocenol B produced by I. lacteus through the induction of Nigrospora oryzae showed selectivity of anti-fungal activity against its co-culture fungus, N. oryzae, with MICs at 16 μg/mL and 128 μg/mL against I. lacteus. The fungus can metabolize these new compounds to inhibit the growth of co-culture fungus while not inhibiting its own growth. Compound 5 was active against acetylcholinesterase (AChE) with a ratio of 35% at the concentration of 50 μM.
2. A biosynthetically inspired synthesis of (-)-berkelic acid and analogs
Christopher F Bender, Christopher L Paradise, Vincent M Lynch, Francis K Yoshimoto, Jef K De Brabander Tetrahedron. 2018 Mar 1;74(9):909-919. doi: 10.1016/j.tet.2018.01.021. Epub 2018 Jan 12.
We describe a complete account of our total synthesis and biological evaluation of (-)-berkelic acid and analogs. We delineate a synthetic strategy inspired by a potentially biomimetic union between the natural products spicifernin and pulvilloric acid. After defining optimal parameters, we executed a one-pot silver-mediated in situ dehydration of an isochroman lactol to methyl pulvillorate, the cycloisomerization of a spicifernin-like alkynol to the corresponding exocyclic enol ether, and a subsequent cycloaddition to deliver the tetracyclic core of berkelic acid. Our studies confirm that the original assigned berkelic acid structure is not stable and equilibrates into a mixture of 4 diastereomers, fully characterized by X-ray crystallography. In addition to berkelic acid, C22-epi-berkelic acid, and nor-berkelic acids, we synthesized C26-oxoberkelic acid analogs that were evaluated against human cancer cell lines. In contrast to data reported for natural berkelic acid, our synthetic material and analogs were found to be devoid of activity.
3. Fifteen new species of Penicillium
C M Visagie, J B Renaud, K M N Burgess, D W Malloch, D Clark, L Ketch, M Urb, G Louis-Seize, R Assabgui, M W Sumarah, K A Seifert Persoonia. 2016 Jun;36:247-80. doi: 10.3767/003158516X691627. Epub 2016 May 9.
We introduce 15 new species of Penicillium isolated from a diverse range of locations, including Canada, Costa Rica, Germany, Italy, New Zealand, Tanzania, USA and the Dry Valleys of Antarctica, from a variety of habitats, including leaf surfaces in tropical rain forests, soil eaten by chimpanzees, infrabuccal pockets of carpenter ants, intestinal contents of caterpillars and soil. The new species are classified in sections Aspergilloides (1), Canescentia (2), Charlesia (1), Exilicaulis (3), Lanata-Divaricata (7) and Stolkia (1). Each is characterised and described using classical morphology, LC-MS based extrolite analyses and multigene phylogenies based on ITS, BenA and CaM. Significant extrolites detected include andrastin, pulvilloric acid, penitrem A and citrinin amongst many others.
Recommended Products
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
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 ╳
