Caloporoside
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-02001 |
| CAS | 160471-36-3 |
| Molecular Weight | 816.92 |
| Molecular Formula | C40H64O17 |
Online Inquiry
Description
Caloporoside is a phospholipase C inhibitor produced by Caloporus dichrous. It has only weak antifungal and bacterial activity, and has the effect of selectively inhibiting phospholipase C.
Specification
| Synonyms | 2-O-Acetyl-5-O-(2-O-acetylhexopyranosyl)-2-C-[17-(2-carboxy-3-hydroxyphenyl)heptadecan-2-yl]hexonic acid; D-Mannonic acid, 5-O-(2-O-acetyl-beta-D-mannopyranosyl)-, 16-(2-carboxy-3-hydroxyphenyl)-1-methylhexadecyl ester, 2-acetate, (R)- |
| IUPAC Name | 2-[(17S,18S,19S,20R)-17-acetyloxy-20-[(2S,3S,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-carboxy-18,19,21-trihydroxy-16-methylhenicosyl]-6-hydroxybenzoic acid |
| Canonical SMILES | CC(CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O)C(C(C(C(CO)OC2C(C(C(C(O2)CO)O)O)OC(=O)C)O)O)(C(=O)O)OC(=O)C |
| InChI | InChI=1S/C40H64O17/c1-24(18-15-13-11-9-7-5-4-6-8-10-12-14-16-19-27-20-17-21-28(45)31(27)37(50)51)40(39(52)53,57-26(3)44)36(49)33(47)30(23-42)56-38-35(54-25(2)43)34(48)32(46)29(22-41)55-38/h17,20-21,24,29-30,32-36,38,41-42,45-49H,4-16,18-19,22-23H2,1-3H3,(H,50,51)(H,52,53)/t24?,29-,30-,32-,33-,34+,35+,36+,38+,40+/m1/s1 |
| InChI Key | BRQJNWFMGNHEQO-LYJPMCOASA-N |
Properties
| Appearance | Oil |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 989.8°C at 760 mmHg |
| Density | 1.33 g/cm3 |
Reference Reading
1. F-16438s, novel binding inhibitors of CD44 and hyaluronic acid. II. Producing organism, fermentation, isolation, physico-chemical properties and structural elucidation
Yuki Hirota-Takahata, Hosami Harada, Isshin Tanaka, Tomoko Nakata, Mutsuo Nakajima, Masaaki Takahashi J Antibiot (Tokyo). 2006 Dec;59(12):777-84. doi: 10.1038/ja.2006.102.
In the course of our screening for binding inhibitors of CD44 and hyaluronic acid, five active compounds, F-16438 A, B, E, F and G were found and isolated from the cultured broth of a fungal strain, Gloeoporus dichrous SANK 30502. The structures of these compounds except for F-16438 G were elucidated by physico-chemical and spectral data to be new compounds related to caloporoside; F-16438 G was identified to be the 6'-malonylated derivative of caloporoside.
2. New caloporoside derivatives and their inhibition of fungal spore germination
Anja Schüffler, Johannes C Liermann, Heinz Kolshorn, Till Opatz, Timm Anke Z Naturforsch C J Biosci. 2009 Jul-Aug;64(7-8):521-5. doi: 10.1515/znc-2009-7-810.
In our ongoing screening culture fluid extracts of Gloeoporus (Caloporus) dichrous strain 83065 inhibited the germination of Magnaporthe grisea and Fusarium graminearum spores. While isolating the active metabolites two new caloporosides, caloporoside G and caloporoside H, in addition to the known caloporoside derivatives F-16438G, caloporoside A, and 2-hydroxy-6-(16-hydroxyheptadecyl)benzoic acid were obtained.
3. Radioligand binding studies of caloporoside and novel congeners with contrasting effects upon [35S] TBPS binding to the mammalian GABA(A) receptor
S Abuhamdah, A Fürstner, G Lees, P L Chazot Biochem Pharmacol. 2005 Nov 1;70(9):1382-8. doi: 10.1016/j.bcp.2005.07.026.
Caloporoside is a natural active fungal metabolite, which was isolated from Caloporous dichrous and was described to exhibit antibacterial, antifungal and phospholipase C inhibitory activity. We have previously reported evidence that related beta-linked compounds, lactose and octyl-beta-d-mannoside, bind and functionally modulate rodent GABA(A) receptors, respectively. We have characterized the binding pharmacology of synthetic caloporoside and two further congeners, 2-hydroxy-6-([(16R)-(beta-d-mannopyranosyloxy)heptadecyl]) benzoic acid and octyl-beta-d-glucoside on GABA(A) receptors using a [35S]-t-butylbicyclophosphoorothionate (TBPS) radioligand binding assay. Caloporoside and 2-hydroxy-6-([(16R)-(beta-d-mannopyranosyloxy)heptadecyl]) benzoic acid produced concentration-dependent complete inhibition of specific [35S] TBPS binding with overall apparent IC50 values of 14.7+/-0.1 and 14.2+/-0.1 microM, respectively. In contrast, octyl-beta-d-glucoside elicited a concentration-dependent stimulation of specific [35S] TBPS binding (E(max)=144+/-4%; EC50=39.2+/-22.7 nM). The level of stimulation was similar to that elicited by diazepam (E(max)=147+/-6%; EC50=0.8+/-0.1 nM), and was occluded by GABA (0.3 microM). However, the three test compounds failed to elicit any significant effect (positive or negative) upon [3H] flunitrazepam or [3H] muscimol binding, indicating that they did not bind directly, or allosterically couple, to the benzodiazepine or agonist binding site of the GABA(A) receptor, respectively. The constituent monosaccharide, glucose, and both the closely related congeners octyl-beta-d-glucoside or hexyl-beta-d-glucoside have no significant effect upon [35S] TBPS binding. These data, together, provide strong evidence that a beta-glycosidic linkage and chain length are crucial for the positive modulation of [35S] TBPS binding to the GABA(A) receptor by this novel chemical class.
Recommended Products
| BBF-01825 | Loganin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00764 | Cerebroside C | 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 ╳
