Stachybotrylactam
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| Category | Mycotoxins |
| Catalog number | BBF-04583 |
| CAS | 163391-76-2 |
| Molecular Weight | 385.50 |
| Molecular Formula | C23H31NO4 |
| Purity | >95% by HPLC |
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Description
An unusual spirodihydrobenzofuranlactam mycotoxin isolated from Stachybotrys sp. It shows immunosuppressant and weak HIV protease activity and shows diverse activity including antiviral, endothelin and pancreatic cholesterase inhibition.
Specification
| Synonyms | 2-deoxy F1839A; (1'R,2'R,4'aS,6'R,8'aS)-3',4',4'a,5',6',7,7',8,8',8'a-Decahydro-4,6'-dihydroxy-2',5',5',8'a-tetramethylspiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalen]-6(3H)-one; [1'R-(1'α,2'α,4'aα,6'α,8'aβ)]-3',4',4'a,5',6',7,7',8,8',8'a-Decahydro-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-spiro[2H-furo[2,3-e]isoindole-2,1'(2'H)-naphthalen]-6(3H)-one; Spirodihydrobenzofuranlactam I |
| Storage | Store at -20°C |
| IUPAC Name | (3R,4aS,7R,8R,8aS)-3,4'-dihydroxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-7,8-dihydro-3H-furo[2,3-e]isoindole]-6'-one |
| Canonical SMILES | CC1CCC2C(C(CCC2(C13CC4=C(C=C5C(=C4O3)CNC5=O)O)C)O)(C)C |
| InChI | InChI=1S/C23H31NO4/c1-12-5-6-17-21(2,3)18(26)7-8-22(17,4)23(12)10-14-16(25)9-13-15(19(14)28-23)11-24-20(13)27/h9,12,17-18,25-26H,5-8,10-11H2,1-4H3,(H,24,27)/t12-,17+,18-,22+,23-/m1/s1 |
| InChI Key | ZSVLMDBFFSSVAK-RCJATNNHSA-N |
| Source | Stachybotrys sp. |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Viruses |
| Boiling Point | 630.0±55.0°C (Predicted) |
| Melting Point | 210°C (dec.) |
| Density | 1.28±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Occurrence of type A, B and D trichothecenes, zearalenone and stachybotrylactam in straw
Sebastian Ulrich, Christoph Gottschalk, Barbara Biermaier, Eunike Bahlinger, Magdalena Twarużek, Sarah Asmussen, Margit Schollenberger, Hana Valenta, Frank Ebel, Sven Dänicke Arch Anim Nutr. 2021 Apr;75(2):105-120. doi: 10.1080/1745039X.2021.1877075. Epub 2021 Feb 21.
Straw is the main by-product of grain production, used as bedding material and animal feed. If produced or stored under adverse hygienic conditions, straw is prone to the growth of filamentous fungi. Some of them, e.g. Aspergillus, Fusarium and Stachybotrys spp. are well-known mycotoxin producers. Since studies on mycotoxins in straw are scarce, 192 straw samples (wheat n = 80; barley n = 79; triticale n = 12; oat n = 11; rye n = 12) were collected across Germany within the German official feed surveillance and screened for the presence of 21 mycotoxins. The following mycotoxins (positive samples for at least one mycotoxin n = 184) were detected: zearalenone (n = 86, 6.0-785 μg/kg), nivalenol (n = 51, 30-2,600 μg/kg), deoxynivalenol (n = 156, 20-24,000 μg/kg), 15-acetyl-deoxynivalenol (n = 34, 20-2,400 μg/kg), 3-acetyl-deoxynivalenol (n = 16, 40-340 μg/kg), scirpentriol (n = 14, 40-680 μg/kg), T-2 toxin (n = 67, 10-250 μg/kg), HT-2 toxin (n = 92, 20-800 μg/kg), T-2 tetraol (n = 13, 70-480 μg/kg). 15-monoacetoxyscirpenol (30 μg/kg) and T-2 triol (60 μg/kg) were only detected in one barley sample. Macrocyclic trichothecenes (satratoxin G, F, roridin E, and verrucarin J) were also found in only one barley sample (quantified as roridin A equivalent: total 183 μg/kg). The occurrence of stachybotrylactam was monitored for the first time in four samples (n = 4, 0.96-7.4 μg/kg). Fusarenon-X, 4,15-diacetoxyscirpenol, neosolaniol, satratoxin H and roridin-L2 were not detectable in the samples. The results indicate a non-negligible contribution of straw to oral and possibly inhalation exposure to mycotoxins of animals or humans handling contaminated straw.
2. The Occurrence and Co-Occurrence of Regulated, Emerging, and Masked Mycotoxins in Rice Bran and Maize from Southeast Asia
Wipada Siri-Anusornsak, Oluwatobi Kolawole, Warapa Mahakarnchanakul, Brett Greer, Awanwee Petchkongkaew, Julie Meneely, Christopher Elliott, Kanithaporn Vangnai Toxins (Basel). 2022 Aug 19;14(8):567. doi: 10.3390/toxins14080567.
Raw feed materials are often contaminated with mycotoxins, and co-occurrence of mycotoxins occurs frequently. A total of 250 samples i.e., rice bran and maize from Cambodia, Laos, Myanmar, and Thailand were analysed using state-of-the-art liquid chromatography-mass spectrometry (LC-MS/MS) for monitoring the occurrence of regulated, emerging, and masked mycotoxins. Seven regulated mycotoxins - aflatoxins, ochratoxin A, fumonisin B1, deoxynivalenol, zearalenone, HT-2, and T-2 toxin were detected as well as some emerging mycotoxins, such as beauvericin, enniatin type B, stachybotrylactam, sterigmatocystin, and masked mycotoxins, specifically zearalenone-14-glucoside, and zearalenone-16-glucoside. Aspergillus and Fusarium mycotoxins were the most prevalent compounds identified, especially aflatoxins and fumonisin B1 in 100% and 95% of samples, respectively. Of the emerging toxins, beauvericin and enniatin type B showed high occurrences, with more than 90% of rice bran and maize contaminated, whereas zearalenone-14-glucoside and zearalenone-16-glucoside were found in rice bran in the range of 56-60%. Regulated mycotoxins (DON and ZEN) were the most frequent mycotoxin combination with emerging mycotoxins (BEA and ENN type B) in rice bran and maize. This study indicates that mycotoxin occurrence and co-occurrence are common in raw feed materials, and it is critical to monitor mycotoxin levels in ASEAN's feedstuffs so that mitigation strategies can be developed and implemented.
3. In vitro screening of 65 mycotoxins for insecticidal potential
Mieczysława Irena Boguś, Anna Katarzyna Wrońska, Agata Kaczmarek, Martyna Boguś-Sobocińska PLoS One. 2021 Mar 18;16(3):e0248772. doi: 10.1371/journal.pone.0248772. eCollection 2021.
The economic losses and threats to human and animal health caused by insects and the pathogens transmitted by them require effective and environmentally-friendly methods of controlling them. One such group of natural biocontrol agents which may be used as biopesticides is that of the entomopathogenic fungi and their toxic secondary metabolites (mycotoxins). The present in vitro work examined the insecticidal potential of 65 commercially-available mycotoxins against the insect Sf-9 cell line. Mammalian Caco-2 and THP-1 cell lines served as reference controls to select insecticidal mycotoxins harmless to mammalian cells. All tested mycotoxins significantly reduced the in vitro proliferation of the Sf-9 cells and evoked morphological changes. Ten of the mycotoxins found to strongly inhibit Sf-9 proliferation also had moderate or no effect on Caco-2 cells. The THP-1 cells were highly resistant to the tested mycotoxins: doses 103 times higher were needed to affect viability and morphology (1 μg/ml for THP-1 versus 1 ng/ml for Sf-9 and Caco-2). Nine mycotoxins significantly decreased Sf-9 cell proliferation with minor effects on mammalian cells: cyclosporins B and D, cytochalasin E, gliotoxin, HC toxin, paxilline, penitrem A, stachybotrylactam and verruculogen. These may be good candidates for future biopesticide formulations.
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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 ╳
