Sirodesmin G
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| Category | Antibiotics |
| Catalog number | BBF-02917 |
| CAS | 64599-26-4 |
| Molecular Weight | 486.56 |
| Molecular Formula | C20H26N2O8S2 |
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Description
It is produced by the strain of Sirodesmum diversum. It has antiviral effect.
Specification
| Related CAS | 53022-75-6 |
| IUPAC Name | [(3S,4S,5S,5'R,7R,10S)-3-hydroxy-10-(hydroxymethyl)-4',4',5',14-tetramethyl-3',9,13-trioxospiro[11,12-dithia-8,14-diazatetracyclo[8.2.2.01,8.03,7]tetradecane-5,2'-oxolane]-4-yl] acetate |
| Canonical SMILES | CC1C(C(=O)C2(O1)CC3C(C2OC(=O)C)(CC45N3C(=O)C(N(C4=O)C)(SS5)CO)O)(C)C |
| InChI | InChI=1S/C20H26N2O8S2/c1-9-16(3,4)12(25)18(30-9)6-11-17(28,13(18)29-10(2)24)7-19-14(26)21(5)20(8-23,32-31-19)15(27)22(11)19/h9,11,13,23,28H,6-8H2,1-5H3/t9-,11-,13+,17+,18-,19?,20+/m1/s1 |
| InChI Key | KTAIGLOGMSQPCG-ATVMRAQZSA-N |
Properties
| Appearance | Amorphous Solid |
| Antibiotic Activity Spectrum | Viruses |
Reference Reading
1. Molecular interactions of the phytotoxins destruxin B and sirodesmin PL with crucifers and cereals: metabolism and elicitation of plant defenses
M Soledade C Pedras, Iman Khallaf Phytochemistry. 2012 May;77:129-39. doi: 10.1016/j.phytochem.2012.02.010. Epub 2012 Mar 11.
Destruxin B and sirodesmin PL are phytotoxins produced by the phytopathogenic fungi Alternaria brassicae (Berk.) Sacc. and Leptosphaeria maculans (asexual stage Phoma lingam), respectively. The molecular interaction of destruxin B and sirodesmin PL with cruciferous and cereal species was investigated using HPLC-ESI-MS(n). It was determined that crucifers transformed destruxin B to hydroxydestruxin B, but sirodesmin PL was not transformed. Overall, the results suggest that the five cruciferous species Arabidopsis thaliana, Thellungiella salsuginea, Erucastrum gallicum, Brassica rapa and Brassica napus are likely to produce a destruxin B detoxifying enzyme (destruxin B hydroxylase), similar to other cruciferous species reported previously. In addition, HPLC analyses and quantification of the phytoalexins elicited in each cruciferous species by these phytotoxins indicates that sirodesmin PL elicits a larger number of phytoalexins than destruxin B. Interestingly, transformation of destruxin B appears to occur also in the cereals Avena sativa and Triticum aestivum; however, the various destruxin metabolites detected in these cereals suggest that these reactions are non-specific enzymatic transformations, contrary to those observed in crucifers, where only a main transformation pathway is detectable. None of the toxins appear to elicit production of metabolites in either A. sativa or T. aestivum.
2. Constitutive expression of transcription factor SirZ blocks pathogenicity in Leptosphaeria maculans independently of sirodesmin production
Andrew S Urquhart, Candace E Elliott, Wei Zeng, Alexander Idnurm PLoS One. 2021 Jun 10;16(6):e0252333. doi: 10.1371/journal.pone.0252333. eCollection 2021.
Sirodesmin, the major secondary metabolite produced by the plant pathogenic fungus Leptosphaeria maculans in vitro, has been linked to disease on Brassica species since the 1970s, and yet its role has remained ambiguous. Re-examination of gene expression data revealed that all previously described genes and two newly identified genes within the sir gene cluster in the genome are down-regulated during the crucial early establishment stages of blackleg disease on Brassica napus. To test if this is a strategy employed by the fungus to avoid damage to and then detection by the host plant during the L. maculans asymptomatic biotrophic phase, sirodesmin was produced constitutively by overexpressing the sirZ gene encoding the transcription factor that coordinates the regulation of the other genes in the sir cluster. The sirZ over-expression strains had a major reduction in pathogenicity. Mutation of the over-expression construct restored pathogenicity. However, mutation of two genes, sirP and sirG, required for specific steps in the sirodesmin biosynthesis pathway, in the sirZ over-expression background resulted in strains that were unable to synthesize sirodesmin, yet were still non-pathogenic. Elucidating the basis for this pathogenicity defect or finding ways to overexpress sirZ during disease may provide new strategies for the control of blackleg disease.
3. Leptosphaeria biglobosa inhibits the production of sirodesmin PL by L. maculans
James A Fortune, Evren Bingol, Aiming Qi, Daniel Baker, Faye Ritchie, Chinthani S Karandeni Dewage, Bruce D L Fitt, Yong-Ju Huang Pest Manag Sci. 2022 Nov 3. doi: 10.1002/ps.7275. Online ahead of print.
Background: Phoma stem canker is caused by two coexisting pathogens, Leptosphaeria maculans and L. biglobosa. They coexist because of their temporal and spatial separations, which are associated with the differences in timing of their ascospore release. L. maculans produces sirodesmin PL, while L. biglobosa does not. However, their interaction/coexistence in terms of secondary metabolite production is not understood. Results: Secondary metabolites were extracted from liquid cultures, L. maculans only (Lm only), L. biglobosa only (Lb only), L. maculans and L. biglobosa simultaneously (Lm&Lb) or sequentially 7 days later (Lm+Lb). Sirodesmin PL or its precursors were identified in extracts from 'Lm only' and 'Lm+Lb', but not from 'Lm&Lb'. Metabolites from 'Lb only', 'Lm&Lb' or 'Lm+Lb' caused significant reductions in L. maculans colony area. However, only the metabolites containing sirodesmin PL caused a significant reduction to L. biglobosa colony area. When oilseed rape cotyledons were inoculated with conidia of 'Lm only', 'Lb only' or 'Lm&Lb', 'Lm only' produced large gray lesions, while 'Lm&Lb' produced small dark lesions similar to lesions caused by 'Lb only'. Sirodesmin PL was found only in the plant extracts from 'Lm only'. These results suggest that L. biglobosa prevents the production of sirodesmin PL and its precursors by L. maculans when they grow simultaneously in vitro or in planta. Conclusion: For the first time, L. biglobosa has been shown to inhibit the production of sirodesmin PL by L. maculans when interacting simultaneously with L. maculans either in vitro or in planta. This antagonistic effect of interspecific interaction may affect their coexistence and subsequent disease progression and management. © 2022 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
