Chrodrimanin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04508 |
| CAS | 132196-54-4 |
| Molecular Weight | 484.54 |
| Molecular Formula | C27H32O8 |
| Purity | ≥95% |
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Description
Chrodrimanin B is a meroterpenoid fungal metabolite that has been found in Talaromyces species. It has insecticidal activity against third instar silkworm larvae (LD50 = 10 μg/g of diet) and selectively inhibits the silkworm GABA receptor RDL (IC50 = 1.13 nM) over human α1β2γ2 subunit-containing GABA receptors (IC50 = 1.48 μM).
Specification
| Synonyms | Thailandolide B; (1R,2R,7aR,8S,9aR,13aS,13bS)-1-(acetyloxy)-1,8,9,9a,10,13a,13b,14-octahydro-5,8-dihydroxy-2,7a,10,10,13a-pentamethyl-2H,4H-benzo[a]pyrano[3,4-j]xanthene-4,11(7aH)-dione; (-)-Chrodrimanin B |
| Storage | Store at -20°C |
| IUPAC Name | [(1S,5R,6R,14R,15S,17R,22S)-10,15-dihydroxy-6,14,18,18,22-pentamethyl-8,19-dioxo-7,13-dioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-3(12),4(9),10,20-tetraen-5-yl] acetate |
| Canonical SMILES | CC1C(C2=C(C(=CC3=C2CC4C5(C=CC(=O)C(C5CC(C4(O3)C)O)(C)C)C)O)C(=O)O1)OC(=O)C |
| InChI | InChI=1S/C27H32O8/c1-12-23(34-13(2)28)21-14-9-18-26(5)8-7-19(30)25(3,4)17(26)11-20(31)27(18,6)35-16(14)10-15(29)22(21)24(32)33-12/h7-8,10,12,17-18,20,23,29,31H,9,11H2,1-6H3/t12-,17+,18+,20+,23+,26+,27-/m1/s1 |
| InChI Key | DYQKBALSPZQWQD-FWEFFTEASA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 663.7±55.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Ethanol, Methanol |
Reference Reading
1. Competitive chrodrimanin B interactions with rat brain GABAA receptors revealed by radioligand binding assays
Kazuhiko Matsuda, Kenji Kai, Hideo Hayashi, Makoto Ihara, Keiji Tanaka Pestic Biochem Physiol . 2022 May;183:105074. doi: 10.1016/j.pestbp.2022.105074.
Meroterpenoid compounds chrodrimanins produced by Talaromyces sp. YO-2 have been shown to act as competitive antagonists of silkworm larval GABAAreceptors using electrophysiology, yet no further evidence has been provided to support such an action. We have investigated the actions of chrodrimanin B on rat brain GABAAreceptors by binding assays with non-competitive ligand of GABAAreceptors [3H]EBOB and competitive ligands [3H]gabazine and [3H]muscimol. Chrodrimanin B did not significantly affect the binding of [3H]EBOB while reducing the binding of [3H]gabazine and [3H]muscimol to the rat membrane preparations. Chrodrimanin B increased the dissociation constant Kdof [3H]gabazine and [3H]muscimol without significantly affecting the maximum binding, pointing to competitive interactions of chrodrimanin B with rat GABAAreceptors in support of our previous observation that the compound acts as a competitive antagonist on the silkworm larval GABA receptor.
2. A new meroterpenoid, chrodrimanin C, from YO-2 of Talaromyces sp
Kenji Kai, Hideo Hayashi, Kohki Akiyama, Yuki Oka Biosci Biotechnol Biochem . 2012;76(4):745-8. doi: 10.1271/bbb.110858.
The new meroterpenoid, chrodrimanin C (3), together with chrodrimanins A (2) and B (1) were isolated from okara (the insoluble residue of whole soybean) that had been fermented with strain YO-2 of Talaromyces sp. Their structures were elucidated by spectroscopic methods. The partial structures of 1 essential for exhibiting insecticidal activity were investigated by using a silkworm assay. The absolute configuration of 1 was also determined.
3. Meroterpenoid Chrodrimanins Are Selective and Potent Blockers of Insect GABA-Gated Chloride Channels
Xinling Yang, Yan Xu, Kazuhiko Matsuda, Kenji Kai, Shogo Furutani, Hideo Hayashi, Yun Ling, Makoto Ihara PLoS One . 2015 Apr 22;10(4):e0122629. doi: 10.1371/journal.pone.0122629.
Meroterpenoid chrodrimanins, produced from Talaromyces sp. YO-2, are known to paralyze silkworm (Bombyx mori) larvae, but their target is unknown. We have investigated the actions of chrodrimanin B on ligand-gated ion channels of silkworm larval neurons using patch-clamp electrophysiology. Chrodrimanin B had no effect on membrane currents when tested alone at 1 μM. However, it completely blocked the γ-aminobutyric acid (GABA)-induced current and showed less pronounced actions on acetylcholine- and L-glutamate-induced currents, when delivered at 1 μM for 1 min prior to co-application with transmitter GABA. Thus, chrodrimanins were also tested on a wild-type isoform of the B. mori GABA receptor (GABAR) RDL using two-electrode voltage-clamp electrophysiology. Chrodrimanin B attenuated the peak current amplitude of the GABA response of RDL with an IC50 of 1.66 nM. The order of the GABAR-blocking potency of chrodrimanins B > D > A was in accordance with their reported insecticidal potency. Chrodrimanin B had no open channel blocking action when tested at 3 nM on the GABA response of RDL. Co-application with 3 nM chrodrimanin B shifted the GABA concentration response curve to a higher concentration and further increase of chrodrimanin B concentration to 10 nM; it reduced maximum current amplitude of the GABA response, pointing to a high-affinity competitive action and a lower affinity non-competitive action. The A282S;T286V double mutation of RDL, which impairs the actions of fipronil, hardly affected the blocking action of chrodrimanin B, indicating a binding site of chrodrimanin B distinct from that of fipronil. Chrodrimanin B showed approximately 1,000-fold lower blocking action on human α1β2γ2 GABAR compared to RDL and thus is a selective blocker of insect GABARs.
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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 ╳
