Roridin C

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Category Bioactive by-products
Catalog number BBF-02199
CAS 2198-93-8
Molecular Weight 250.33
Molecular Formula C15H22O3
Purity >98%

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Description

Roridin C is a fungal sesquiterpene derived from Myrothecium roridum S-1135 (NRRL 3005).

Specification

Synonyms Trichodermol; BRN 1287601; 12,13-Epoxytrichothec-9-en-4-beta-ol; (2S,2'R,4'R,5'S,5a'R,9a'R)-5',5a',8'-trimethyl-2',3',4',5',5a',6',7',9a'-octahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-4'-ol
IUPAC Name (1S,2R,7R,9R,11R,12S)-1,2,5-trimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-ol
Canonical SMILES CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)O)C)C
InChI InChI=1S/C15H22O3/c1-9-4-5-13(2)11(6-9)18-12-7-10(16)14(13,3)15(12)8-17-15/h6,10-12,16H,4-5,7-8H2,1-3H3/t10-,11-,12-,13+,14-,15+/m1/s1
InChI Key XSUVNTHNQMGPIL-LACSLYJWSA-N
Source Trichothecenes are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti.

Properties

Appearance Acicular Crystal
Boiling Point 373.2°C at 760 mmHg
Melting Point 117-119°C
Density 1.2 g/cm3

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Mechanism Of Toxicity Roridin C is also known as 12,13-Epoxytrichothec-9-en-4-beta-ol. Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis.

Reference Reading

1. Entwicklung eines immunchemischen Schnelltestverfahrens zum Multimykotoxinnachweis
B Mayer, E Schneider, E Usleber, R Dietrich, C Bürk, E Märtlbauer Mycotoxin Res. 2000 Jun;16 Suppl 2:227-30. doi: 10.1007/BF02940044.
A rapid immunochemical test system (immunofiltration, flow-through test) was developed for the simultaneous detection of seven mycotoxins, namely aflatoxin B1 (AFB1), fumonisin B1 (FB1), ochratoxin A (OA), deoxynivalenol (DON), T-2 toxin (T-2), diacetoxyscirpenol (DAS), and roridin A (RoA), respectively. A reusable test device, containing seven sample wells and one control well was produced. Sample extract solutions were dropped onto each sample well and the controll well, followed by toxin-enzyme conjugate solution, wash solution and colour delevoper solution. The test results were evaluated by visual comparison of colour intensity of sample wells and control well. The detection limits in buffer solution were at 0.5 ng/ml (AFB1), 5 ng/ml (FB1), 5 ng/ml (OA), 500 ng/ml (DON), 10 ng/ml (T-2), 0.5 ng/ml (DAS), and 25 ng/ml (RoA), respectively. Employing a simple extraction procedure, artificially contaminated cereal samples (wheat, maize) were analysed, with detection limits of 10 ng/g (AFB1), 50 ng/g (FB1), 50 ng/g (OA), 3500 ng/g (DON), 100 ng/g (T-2), 5 ng/g (DAS), and 250 ng/g (RoA), respectively.
2. Trichothecenes in food and feed: Occurrence, impact on human health and their detection and management strategies
Dipendra Kumar Mahato, Shikha Pandhi, Madhu Kamle, Akansha Gupta, Bharti Sharma, Brajesh Kumar Panda, Shubhangi Srivastava, Manoj Kumar, Raman Selvakumar, Arun Kumar Pandey, Priyanka Suthar, Shalini Arora, Arvind Kumar, Shirani Gamlath, Ajay Bharti, Pradeep Kumar Toxicon. 2022 Mar;208:62-77. doi: 10.1016/j.toxicon.2022.01.011. Epub 2022 Jan 31.
Trichothecenes (TCNs) are the mycotoxins produced by many fungal species such as Fusarium, Myrothecium, and Stachybotrys and pose a considerable health risk. Based on their characteristic functional moieties, they are divided into four categories: Type A (T-2, HT-2, diacetoxyscirpenol (DAS), harzianum A, neosolaniol (NEO) and trichodermin), Type B (deoxynivalenol (DON), nivalenol (NIV), trichothecin and fusarenon X), Type C (crotocin) and Type D (satratoxin G & H, roridin A and verrucarin A) with types A and B being the most substantial. TCNs cause growth retardation in eukaryotes, suppress seedling growth or regeneration in plants and could be a reason for animal reproductive failure. Due to the increased frequency of occurrence and widespread distribution of TCNs in food and feed, knowledge of their sources of occurrence is essential to strategise their control and management. Hence, this review provides an overview of various types and sources of TCNs, the associated biosynthetic pathways and genes responsible for production in food and feed. Further, various processing and environmental effects on TCNs production, detection techniques and management strategies are also briefly outlined.
3. Stachybotrys-Toxine in einer Münchner Wohnung mit Wasserschaden
E Usleber, R Dietrich, E Schneider, E Märtlbauer Mycotoxin Res. 2001 Jun;17 Suppl 2:234-7. doi: 10.1007/BF03036443.
This paper presents a case report of indoor Stachybotrys toxins in Germany. In the summer of 2000, heavy rainfall and a leakage of the gutter system of an appartement house in Munich, Germany, caused a severe water damage in one of the appartments. The appartment was at that time occupied by two of the authors (ES, EU). A wall (covered with wallpaper) in one room in particular was most strongly affected, about 6-8 m(2) of the wallpaper became very wet. Large parts of this wet wallpaper were within days infested by multiple circumscribed round, grey-black colonies (0.5-5 cm in diameter) of presumtiveStachybotrys spp.. At the same time, the air in this room became very damp and oppressive. Several persons reported burning sensations on the mucous membranes of the eye, nose, and larynx, followed by headache symptoms, as soon as a few minutes after they had entered this room. Inadvertent skin contact with one of the fungal colonies by one person resulted in burning sensations immediately, but symptoms disappeared after thorough rinsing of the skin with water. The infested room was evacuated, and samples were taken from the wet wallpaper at areas (1) in the center of the most heavy fungal colony growth, (2) several cm away from colony growth, and (3) from locations which were wet but about 1 m away from visible colony growth. The samples were extracted with methanol, the extract diluted with buffer solution and analysed by competitive enzyme immunoassay (EIA) for roridin A. Due to cross-reactivity, this EIA detects several macrocyclic trichothecenes produced byStachybotrys spp.. Heavily infected pieces of wallpaper were strongly contaminated with toxins, with maximum concentrations of 1.1 microgram per cm(2) (Roridin A equivalents). Wet but visibly not infected samples of wallpaper were negative in the EIA. Considering a EIA cross-reactivity of satratoxin H (the major Stachybotrys-toxin) of 15%, the actual maximum toxin concentration would correspond to 6 microgram of satratoxin H per cm(2). As far as we know, this is the first documented case of indoor Stachybotrys toxins in Germany. The toxin concentration by far exceeds the minimum toxin level required for skin toxicity, and was considered as unhealthy. Health authorities in Munich were informed but were unable to provide assistance, probably because awareness of the importance and the possible health risks caused by indoor mycotoxins is not yet widespread in Germany. Reporting and monitoring programs for mycotoxins in water-damaged buildings seem to be necessary to provide insight into the occurrence of similar cases as the one described here.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H22O3
Molecular Weight (Monoisotopic Mass): 250.1569 Da
Molecular Weight (Avergae Mass): 250.3334 Da

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