Roridin L2
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| Category | Bioactive by-products |
| Catalog number | BBF-02203 |
| CAS | 85124-22-7 |
| Molecular Weight | 530.61 |
| Molecular Formula | C29H38O9 |
| Purity | >70% |
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Description
Roridin L2 is originally isolated from M. roridum var. and it has antibacterial and antitumor effects.
Specification
| Synonyms | (2S,2'R,4'R,5'S,5a'R,9a'R)-5a'-(hydroxymethyl)-5',8'-dimethyl-2',3',4',5',5a',6',7',9a'-octahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-4'-yl (2Z,4E)-7-hydroxy-6-(2-(5-oxo-2,5-dihydrofuran-3-yl)ethoxy)octa-2,4-dienoate |
| Storage | Store at -20°C |
| IUPAC Name | [(1S,2R,7R,9R,11R,12S)-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-yl] (2Z,4E)-7-hydroxy-6-[2-(5-oxo-2H-furan-3-yl)ethoxy]octa-2,4-dienoate |
| Canonical SMILES | CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)OC(=O)C=CC=CC(C(C)O)OCCC5=CC(=O)OC5)C)CO |
| InChI | InChI=1S/C29H38O9/c1-18-8-10-28(16-30)23(12-18)37-24-14-22(27(28,3)29(24)17-36-29)38-25(32)7-5-4-6-21(19(2)31)34-11-9-20-13-26(33)35-15-20/h4-7,12-13,19,21-24,30-31H,8-11,14-17H2,1-3H3/b6-4+,7-5-/t19?,21?,22-,23-,24-,27-,28-,29+/m1/s1 |
| InChI Key | JGIYRVDWRBKREW-JNMAXWDTSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 93-97°C |
| Solubility | Soluble in Dichloromethane, DMSO, Ethanol, Methanol |
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. Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum
Waranya Lakornwong, Kwanjai Kanokmedhakul, Kasem Soytong, Arm Unartngam, Sarawut Tontapha, Vittaya Amornkitbamrung, Somdej Kanokmedhakul Planta Med. 2019 Jul;85(9-10):774-780. doi: 10.1055/a-0895-5753. Epub 2019 Apr 26.
Chromatographic separation of extracts from the fungal biomass of a plant pathogenic fungus, Myrothecium roridum, yielded 8 trichothecene toxins including 6 type D trichothecenes (1: -6: ) and 2 type A trichothecenes (7: -8: ). 6',12'-Epoxymyrotoxin A (1: ) and 7'-hydroxymytoxin B (2: ) were new macrocyclic trichothecenes, while the other trichothecenes were identified as myrotoxin B (3: ), myrotoxin D hydrate (4: ), 2',3'-epoxymyrothecine A (5: ), miotoxin A (6: ), and 2 trichothecenes lacking the macrocyclic lactone system, roridin L-2 (7: ) and trichoverritone (8: ). The structures of these mycotoxins were characterized using spectroscopic methods. The absolute configurations of 1: and 2: were determined by NOESY and a comparison of their experimental and calculated ECD spectra. Most of these mycotoxins (1: -4: and 6: ) exhibited highly potent antimalarial activity against Plasmodium falciparum. They also showed strong cytotoxicity towards KB and NCI-H187 cell lines (IC50 0.60 - 112.28 nM), as well as the Vero cell line (IC50 1.50 - 46.51 nM).
3. Toxin Production by Stachybotrys chartarum Genotype S on Different Culture Media
Sebastian Ulrich, Cornelius Schäfer J Fungi (Basel). 2020 Sep 2;6(3):159. doi: 10.3390/jof6030159.
Stachybotrys (S.) chartarum had been linked to severe health problems in humans and animals, which occur after exposure to the toxic secondary metabolites of this mold. S. chartarum had been isolated from different environmental sources, ranging from culinary herbs and improperly stored fodder to damp building materials. To access the pathogenic potential of isolates, it is essential to analyze them under defined conditions that allow for the production of their toxic metabolites. All Stachybotrys species are assumed to produce the immunosuppressive phenylspirodrimanes, but the highly cytotoxic macrocyclic trichothecenes are exclusively generated by the genotype S of S. chartarum. In this study, we have analyzed four genotype S strains initially isolated from three different habitats. We grew them on five commonly used media (malt-extract-agar, glucose-yeast-peptone-agar, potato-dextrose-agar, cellulose-agar, Sabouraud-dextrose-agar) to identify conditions that promote mycotoxin production. Using LC-MS/MS, we have quantified stachybotrylactam and all S-type specific macrocyclic trichothecenes (satratoxin G, H, F, roridin E, L-2, verrucarin J). All five media supported a comparable fungal growth and sporulation at 25 °C in the dark. The highest concentrations of macrocyclic trichothecenes were detected on potato-dextrose-agar or cellulose-agar. Malt-extract-agar let to an intermediate and glucose-yeast-peptone-agar and Sabouraud-dextrose-agar to a poor mycotoxin production. These data demonstrate that the mycotoxin production clearly depends on the composition of the respective medium. Our findings provide a starting point for further studies in order to identify individual components that either support or repress the production of mycotoxins in S. chartarum.
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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 ╳
