Botrydial
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| Category | Mycotoxins |
| Catalog number | BBF-00163 |
| CAS | 54986-75-3 |
| Molecular Weight | 310.38 |
| Molecular Formula | C17H26O5 |
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Description
Botrydial is a phytotoxic sesquiterpene metabolite secreted by the fungus Botrytis cinerea. It has anti-candida fungi activity and has only weak antibacterial effect.
Specification
| IUPAC Name | [(1S,3aR,4S,6R,7S,7aS)-1,7-diformyl-7a-hydroxy-1,3,3,6-tetramethyl-2,3a,4,5,6,7-hexahydroinden-4-yl] acetate |
| Canonical SMILES | CC1CC(C2C(CC(C2(C1C=O)O)(C)C=O)(C)C)OC(=O)C |
| InChI | InChI=1S/C17H26O5/c1-10-6-13(22-11(2)20)14-15(3,4)8-16(5,9-19)17(14,21)12(10)7-18/h7,9-10,12-14,21H,6,8H2,1-5H3/t10-,12+,13+,14+,16-,17-/m1/s1 |
| InChI Key | SJFIYVCSGNWVPJ-GKKOWQTJSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 108-110°C |
Reference Reading
1. The sesquiterpene botrydial from Botrytis cinerea induces phosphatidic acid production in tomato cell suspensions
Juan Martin D'Ambrosio, Gabriela Gonorazky, Daniela J Sueldo, Javier Moraga, Andrés Arruebarrena Di Palma, Lorenzo Lamattina, Isidro González Collado, Ana Maria Laxalt Planta. 2018 Apr;247(4):1001-1009. doi: 10.1007/s00425-018-2843-8. Epub 2018 Jan 16.
The phytotoxin botrydial triggers PA production in tomato cell suspensions via PLD and PLC/DGK activation. PLC/DGK-derived PA is partially required for botrydial-induced ROS generation. Phosphatidic acid (PA) is a phospholipid second messenger involved in the induction of plant defense responses. It is generated via two distinct enzymatic pathways, either via phospholipase D (PLD) or by the sequential action of phospholipase C and diacylglycerol kinase (PLC/DGK). Botrydial is a phytotoxic sesquiterpene generated by the necrotrophic fungus Botrytis cinerea that induces diverse plant defense responses, such as the production of reactive oxygen species (ROS). Here, we analyzed PA and ROS production and their interplay upon botrydial treatments, employing tomato (Solanum lycopersicum) cell suspensions as a model system. Botrydial induces PA production within minutes via PLD and PLC/DGK. Either inhibition of PLC or DGK diminishes ROS generation triggered by botrydial. This indicates that PLC/DGK is upstream of ROS production. In tomato, PLC is encoded by a multigene family constituted by SlPLC1-SlPLC6 and the pseudogene SlPLC7. We have shown that SlPLC2-silenced plants have reduced susceptibility to B. cinerea. In this work, we studied the role of SlPLC2 on botrydial-induced PA production by silencing the expression of SlPLC2 via a specific artificial microRNA. Upon botrydial treatments, SlPLC2-silenced-cell suspensions produce PA levels similar to wild-type cells. It can be concluded that PA is a novel component of the plant responses triggered by botrydial.
2. Botrydial confers Botrytis cinerea the ability to antagonize soil and phyllospheric bacteria
Paulina Vignatti, María E Gonzalez, Edgardo C Jofré, Hernando J Bolívar-Anillo, Javier Moraga, Muriel Viaud, Isidro G Collado, Fernando L Pieckenstain Fungal Biol. 2020 Jan;124(1):54-64. doi: 10.1016/j.funbio.2019.11.003. Epub 2019 Nov 15.
The role of the sesquiterpene botrydial in the interaction of the phytopathogenic fungus Botrytis cinerea and plant-associated bacteria was analyzed. From a collection of soil and phyllospheric bacteria, nine strains sensitive to growth-inhibition by B. cinerea were identified. B. cinerea mutants unable to produce botrydial caused no bacterial inhibition, thus demonstrating the inhibitory role of botrydial. A taxonomic analysis showed that these bacteria corresponded to different Bacillus species (six strains), Pseudomonas yamanorum (two strains) and Erwinia aphidicola (one strain). Inoculation of WT and botrydial non-producing mutants of B. cinerea along with Bacillusamyloliquefaciens strain MEP218 in soil demonstrated that both microorganisms exert reciprocal inhibitory effects; the inhibition caused by B. cinerea being dependent on botrydial production. Moreover, botrydial production was modulated by the presence of B. amyloliquefaciens MEP218 in confrontation assays in vitro. Purified botrydial in turn, inhibited growth of Bacillus strains in vitro and cyclic lipopeptide (surfactin) production by B. amyloliquefaciens MEP218. As a whole, results demonstrate that botrydial confers B. cinerea the ability to inhibit potential biocontrol bacteria of the genus Bacillus. We propose that resistance to botrydial could be used as an additional criterion for the selection of biocontrol agents of plant diseases caused by B. cinerea.
3. Impairment of botrydial production in Botrytis cinerea allows the isolation of undescribed polyketides and reveals new insights into the botcinins biosynthetic pathway
Javier Moraga, Inmaculada Izquierdo-Bueno Reina, Cristina Pinedo, Rosario Hernández-Galán, Muriel Viaud, Isidro G Collado Phytochemistry. 2021 Mar;183:112627. doi: 10.1016/j.phytochem.2020.112627. Epub 2021 Jan 8.
Botrytis cinerea is a necrotrophic fungal pathogen that affects a total of 586 genera representing approximately 1400 plant species. This pathogen produces two families of phytotoxins involved in its infection process i.e. botrydial and its relatives, and botcinic and botcineric acids and their relatives, botcinins. The botrydial biosynthetic cluster consists of seven genes, where the gene BcBOT4 encodes a cytochrome P450 monooxygenase that was shown to catalyse regio- and stereospecific hydroxylation at position C-4 of the presilphiperfolan-8-β-ol skeleton. The null mutant bcbot4Δ halted the production of botrydial and its derivatives, and instead accumulated tricyclic presilphiperfolane alcohol and overproduced a significant number of polyketides. A detailed study of the bcbot4Δ mutant led us to the isolation and characterization of five undescribed polyketides, three derived from botcinic and botcineric acids (botcinins H, I, J), one derived from the initial pentaketide (botcinin K), and one cinbotolide derivative (cinbotolide D). Botcinins are tetra-methylated tetraketides biosynthesized by the sequential assembly of a pentaketide (C10) based on an acetate primer unit which is lost through a retro-Claisen type C-C bond cleavage. The structural characterization of botcinin K showed a basic chemical structure corresponding to a botcinin (C14) derivative obtained directly from the original per-methylated pentaketide leading to the biosynthesis of botrylactone and other botcinins, confirming the previously proposed biosynthetic route.
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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 ╳
