Terpendole E
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03102 |
| CAS | 167427-23-8 |
| Molecular Weight | 437.61 |
| Molecular Formula | C28H39NO3 |
| Purity | >98% |
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Description
Terpendole E is an acyl-CoA: cholesterol acyltransferase (ACAT) inhibitor produced by Albophoma yamenashiensis. The IC50 that inhibits ACAT in macrophages is 0.29 µmol/L, and the CD50 that causes 50% cell damage is greater than 23.4 µmol/L.
Specification
| Synonyms | (2S,4R,4aR,4bR,6aS,12bS,12cS,14aS)-2-(2-Hydroxypropan-2-yl)-4a,12b,12c-trimethyl-3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-4-ol |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2S,5S,7S,9R,10R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-16(24),17,19,21-tetraen-9-ol |
| Canonical SMILES | CC12CCC3C(C1CCC4C2(C5=C(C4)C6=CC=CC=C6N5)C)(C(CC(O3)C(C)(C)O)O)C |
| InChI | InChI=1S/C28H39NO3/c1-25(2,31)23-15-21(30)27(4)20-11-10-16-14-18-17-8-6-7-9-19(17)29-24(18)28(16,5)26(20,3)13-12-22(27)32-23/h6-9,16,20-23,29-31H,10-15H2,1-5H3/t16-,20+,21+,22-,23-,26-,27+,28+/m0/s1 |
| InChI Key | SVYIMXYKHRBHSG-KYYKPQATSA-N |
Properties
| Appearance | Colorless Crystal |
| Boiling Point | 597.1±50.0°C at 760 mmHg |
| Melting Point | 174-176°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Identification of Indole Diterpenes in Ipomoea asarifolia and Ipomoea muelleri, Plants Tremorgenic to Livestock
Stephen T Lee, Dale R Gardner, Daniel Cook J Agric Food Chem. 2017 Jul 5;65(26):5266-5277. doi: 10.1021/acs.jafc.7b01834. Epub 2017 Jun 20.
Ipomoea asarifolia has been associated with a tremorgenic syndrome in livestock in Brazil and was recently reported to contain tremorgenic indole diterpenes. Ipomoea muelleri has been reported to cause a similar tremorgenic syndrome in livestock in Australia. Ipomoea asarifolia and I. muelleri were investigated by high-performance liquid chromatography-high-resolution mass spectometry (HPLC-HRMS) and high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) for indole diterpene composition. The high-resolution mass spectrometric data in combination with MS/MS fragmentation mass spectral data provided valuable information for indole diterpene characterization. The previous report of indole diterpenes in I. asarifolia was confirmed and expanded; and the presence of indole diterpenes in I. muelleri is reported for the first time. Two new indole diterpenes were isolated and their structures determined by 1D and 2D NMR spectroscopy and given the names 11-hydroxy-12,13-epoxyterpendole K and 6,7-dehydroterpendole A. The presence of terpendole K and terpendole E in I. asarifolia is unequivocally demonstrated for the first time. This is the first detailed MS analysis of known indole diterpenes and possible isomers in I. asarifolia and I. muelleri.
2. Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism
Takayuki Motoyama, Hiroyuki Osada Bioorg Med Chem Lett. 2016 Dec 15;26(24):5843-5850. doi: 10.1016/j.bmcl.2016.11.013. Epub 2016 Nov 9.
The diversity of natural products is greater than that of combinatorial chemistry compounds and is similar to that of drugs. Compounds rich in sp3 carbons, such as natural products, typically exhibit high structural complexity and high specificity to molecular targets. Microorganisms can synthesize such sp3 carbon-rich compounds and can be used as excellent factories for making bioactive compounds. Here, we mainly focus on pathway engineering of two sp3 carbon-rich bioactive indole alkaloids, fumitremorgin C and terpendole E. We also demonstrate the importance of activation of secondary metabolism by focusing on tenuazonic acid, a bioactive tetramic acid compound, as an example.
3. The Known Antimammalian and Insecticidal Alkaloids Are Not Responsible for the Antifungal Activity of Epichloë Endophytes
Krishni Fernando, Priyanka Reddy, Simone Vassiliadis, German C Spangenberg, Simone J Rochfort, Kathryn M Guthridge Plants (Basel). 2021 Nov 17;10(11):2486. doi: 10.3390/plants10112486.
Asexual Epichloë sp. endophytes in association with pasture grasses produce agronomically important alkaloids (e.g., lolitrem B, epoxy-janthitrems, ergovaline, peramine, and lolines) that exhibit toxicity to grazing mammals and/or insect pests. Novel strains are primarily characterised for the presence of these compounds to ensure they are beneficial in an agronomical setting. Previous work identified endophyte strains that exhibit enhanced antifungal activity, which have the potential to improve pasture and turf quality as well as animal welfare through phytopathogen disease control. The contribution of endophyte-derived alkaloids to improving pasture and turf grass disease resistance has not been closely examined. To assess antifungal bioactivity, nine Epichloë related compounds, namely peramine hemisulfate, n-formylloline-d3, n-acetylloline hydrochloride, lolitrem B, janthitrem A, paxilline, terpendole E, terpendole C, and ergovaline, and four Claviceps purpurea ergot alkaloids, namely ergotamine, ergocornine, ergocryptine, and ergotaminine, were tested at concentrations higher than observed in planta in glasshouse and field settings using in vitro agar well diffusion assays against three common pasture and turf phytopathogens, namely Ceratobasidium sp., Drechslera sp., and Fusarium sp. Visual characterisation of bioactivity using pathogen growth area, mycelial density, and direction of growth indicated no inhibition of pathogen growth. This was confirmed by statistical analysis. The compounds responsible for antifungal bioactivity of Epichloë endophytes hence remain unknown and require further investigation.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
