Terpendole L
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03103 |
| CAS | |
| Molecular Weight | 587.79 |
| Molecular Formula | C37H49NO5 |
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Description
Terpendole F 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 | (3S,4aR,4bR,5aS,5bS,7aS,13bS,13cR,15aS,16aS)-1,1,13b,13c-tetramethyl-9-(3-methylbut-2-en-1-yl)-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[4',4a']chromeno[5',6':6,7]indeno[1,2-b]indol-5b-ol |
| IUPAC Name | (1R,2S,13S,16S,17S,19R,20R,22S,25S,27S)-1,2,24,24-tetramethyl-9-(3-methylbut-2-enyl)-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(=CCC1=C2C3=C(C4(C(C3)CCC5(C4(CCC6C57C(O7)C8C(O6)C(OC(O8)C=C(C)C)(C)C)C)O)C)NC2=CC=C1)C |
| InChI | InChI=1S/C37H49NO5/c1-20(2)12-13-22-10-9-11-25-28(22)24-19-23-14-17-36(39)34(7,35(23,8)30(24)38-25)16-15-26-37(36)32(43-37)29-31(40-26)33(5,6)42-27(41-29)18-21(3)4/h9-12,18,23,26-27,29,31-32,38-39H,13-17,19H2,1-8H3/t23-,26-,27-,29+,31-,32+,34+,35+,36-,37-/m0/s1 |
| InChI Key | LLRYILBJBZFIRA-YPNCZJMTSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 693.0±55.0°C at 760 mmHg |
| Melting Point | 148-150°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Two New Prenylated Indole Diterpenoids from Tolypocladium sp. and Their Antimicrobial Activities
Lu-Lin Xu, Xue-Jiao Pang, Qiong Shi, Peng-Jie Xian, Yan-Duo Tao, Xiao-Long Yang Chem Biodivers. 2019 Jun;16(6):e1900116. doi: 10.1002/cbdv.201900116. Epub 2019 Apr 29.
Two new prenylated indole diterpenoids, tolypocladins K and L (1 and 2), together with a known analog terpendole L (3), were isolated from the solid fermentation culture of a mine soil-derived fungus Tolypocladium sp. XL115. Their structures and relative configurations were determined by comprehensive spectroscopic data analysis, as well as by comparison of their NMR data with those related known compounds. Compound 3 exhibited remarkable antibacterial activity against Micrococcus luteus with an MIC value of 6.25 μg/mL, and compounds 1 and 3 displayed moderate antifungal activity selectively against tested strains with MIC values of 25-50 μg/mL.
2. Quantitation and Distribution of Epichloë-Derived Alkaloids in Perennial Ryegrass Tissues
Simone Vassiliadis, Priyanka Reddy, Joanne Hemsworth, German C Spangenberg, Kathryn M Guthridge, Simone J Rochfort Metabolites. 2023 Jan 30;13(2):205. doi: 10.3390/metabo13020205.
Perennial ryegrass (Lolium perenne L.), an economically important pasture and turf grass, is commonly infected with asexual Epichloë species endophytes. Endophytes provide enhanced bioprotection by producing alkaloids, and research often focusses on the negative impact on grazing animals. However, alkaloid distribution throughout the plant and their role in biocontrol of insect pests and diseases are less well understood. Additionally, intermediate compounds have not been investigated for their impacts on animal welfare and biological control in pasture-based scenarios. Here, a single liquid chromatography-mass spectrometry (LC-MS) method was used to measure seven alkaloids in different perennial ryegrass tissues infected with SE or NEA12 endophytes. High alkaloid recoveries and a clear plant matrix effect emphasize the importance of using matrix-matched standards for accurate quantitation. The method is sensitive, detecting alkaloids at low concentrations (nanogram levels), which is important for endophyte strains that produce compounds detrimental to livestock. Concentrations were generally highest in seeds, but distribution differed in the shoots/roots: peramine, terpendole E, terpendole C and lolitrem B were higher in shoots, whilst ergovaline, paxilline and epoxy-janthitrem I were more evenly distributed throughout the two tissues. Knowledge of alkaloid distribution may allow for concentrations to be predicted in roots based on concentrations in the shoots, thereby assisting future determinations of resistance to insects, especially subterranean root-feeding pests.
3. Chromanones and aryl glucoside analogs from the entomopathogenic fungus Aschersonia confluens BCC53152
Karoon Sadorn, Siriporn Saepua, Wikorn Punyain, Wacharee Saortep, Wilunda Choowong, Pranee Rachtawee, Pattama Pittayakhajonwut Fitoterapia. 2020 Jul;144:104606. doi: 10.1016/j.fitote.2020.104606. Epub 2020 May 3.
Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4'-O-methylglucoside (8), 4'-O-methylpleoside (10), and 4'-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4'-O-methyl-β-d-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-l-3-phenyllactic acid (15), papuline [or (2S)-l-3-phenyllactic acid methyl ester, 16], 2'-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1-3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.
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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 ╳
