Terpendole C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03499 |
| CAS | 156967-65-6 |
| Molecular Weight | 519.67 |
| Molecular Formula | C32H41NO5 |
| Purity | >98% |
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Description
Terpendole C is an acyl-CoA: cholesterol acyltransferase (ACAT) inhibitor produced by Albophoma yamenashiensis. The IC50 that inhibits ACAT in macrophages is 0.46 µmol/L, and the CD50 that causes 50% cell damage is greater than 24.1 µmol/L.
Specification
| Synonyms | (3S,4aR,4bR,5aS,5bS,7aS,13bS,13cR,15aS,16aS)-1,1,13b,13c-tetramethyl-3-(2-methylprop-1-en-1-yl)-1,4a,4b,6,7,7a,8,13,13b,13c,14,15,15a,16a-tetradecahydro-5bH-[1,3]dioxino[5'',4'':2',3']oxireno[2'',3'':4',4a']chromeno[5',6':6,7]indeno[1,2-b]indol-5b-ol; (-)-terpendole C |
| Storage | Store at -20°C |
| IUPAC Name | (1R,2S,13S,16S,17S,19R,20R,22S,25S,27S)-1,2,24,24-tetramethyl-22-(2-methylprop-1-enyl)-18,21,23,26-tetraoxa-4-azaoctacyclo[14.13.0.02,13.03,11.05,10.017,19.017,27.020,25]nonacosa-3(11),5,7,9-tetraen-16-ol |
| Canonical SMILES | CC(=CC1OC2C(C(O1)(C)C)OC3CCC4(C5(C(CCC4(C36C2O6)O)CC7=C5NC8=CC=CC=C78)C)C)C |
| InChI | InChI=1S/C32H41NO5/c1-17(2)15-23-36-24-26(28(3,4)37-23)35-22-12-13-29(5)30(6)18(11-14-31(29,34)32(22)27(24)38-32)16-20-19-9-7-8-10-21(19)33-25(20)30/h7-10,15,18,22-24,26-27,33-34H,11-14,16H2,1-6H3/t18-,22-,23-,24+,26-,27+,29+,30+,31-,32-/m0/s1 |
| InChI Key | WUOATFFODCBZBE-SCGIUCFSSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 645.4±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. The Known Antimammalian and Insecticidal Alkaloids Are Not Responsible for the Antifungal Activity of Epichloë Endophytes
Krishni Fernando, German C Spangenberg, Simone J Rochfort, Kathryn M Guthridge, Priyanka Reddy, Simone Vassiliadis Plants (Basel) . 2021 Nov 17;10(11):2486. doi: 10.3390/plants10112486.
AsexualEpichloësp. 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, nineEpichloërelated compounds, namely peramine hemisulfate,n-formylloline-d3,n-acetylloline hydrochloride, lolitrem B, janthitrem A, paxilline, terpendole E, terpendole C, and ergovaline, and fourClaviceps purpureaergot 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, namelyCeratobasidiumsp.,Drechslerasp., andFusariumsp. 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 ofEpichloëendophytes hence remain unknown and require further investigation.
2. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. II. Structure elucidation of terpendoles A, B, C and D
H Takayanagi, S Omura, K Shiomi, H Tomoda, N Tabata, X H Huang, D J Yang, H Nishida J Antibiot (Tokyo) . 1995 Jan;48(1):5-11. doi: 10.7164/antibiotics.48.5.
Structures of terpendoles A, B, C and D, novel acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors, were determined by spectroscopic studies. All terpendoles consist of diterpene and indole moieties in common. Terpendoles A, C and D possess an additional isoprenyl unit via oxygen atom(s) of their diterpene moieties. The relative stereochemistries of terpendoles C and D were confirmed by NOE experiments and X-ray crystallographic analysis.
3. Tremorgenic Indole Diterpenes from Ipomoea asarifolia and Ipomoea muelleri and the Identification of 6,7-Dehydro-11-hydroxy-12,13-epoxyterpendole A
Franklin Riet-Correa, Kevin D Welch, Daniel Cook, Dale R Gardner, Stephen T Lee J Nat Prod . 2018 Jul 27;81(7):1682-1686. doi: 10.1021/acs.jnatprod.8b00257.
Indole diterpene alkaloids have been isolated from Ipomoea asarifolia and I. muelleri and are associated with a tremorgenic syndrome in livestock. To better characterize the tremorgenic activity of the major indole diterpene alkaloids in these two plants, terpendole K (1), 6,7-dehydroterpendole A (2), 11-hydroxy-12,13-epoxyterpendole K (3), terpendole C (5), paxilline (6), and a new compound, 6,7-dehydro-11-hydroxy-12,13-epoxyterpendole A (4), were isolated and evaluated for tremorgenic activity in a mouse model. Compounds 1, 2, 5, and 6 all showed similar and significant signs of tremorgenic activity. In contrast, the 11-hydroxy-12,13-epoxy compounds, 3 and 4, showed no significant tremorgenic activity.
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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 ╳
