Terpendole A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03101 |
| CAS | |
| Molecular Weight | 535.67 |
| Molecular Formula | C32H41NO6 |
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Description
Terpendole A 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
| IUPAC Name | (1S,2R,13R,16R,17R,19S,20S,22R,25R,27R)-22-(3,3-dimethyloxiran-2-yl)-1,2,24,24-tetramethyl-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 | CC1(C2C(C3C4(O3)C(O2)CCC5(C4(CCC6C5(C7=C(C6)C8=CC=CC=C8N7)C)O)C)OC(O1)C9C(O9)(C)C)C |
| InChI | InChI=1S/C32H41NO6/c1-27(2)23-21(36-26(39-27)25-28(3,4)37-25)24-32(38-24)20(35-23)12-13-29(5)30(6)16(11-14-31(29,32)34)15-18-17-9-7-8-10-19(17)33-22(18)30/h7-10,16,20-21,23-26,33-34H,11-15H2,1-6H3/t16-,20-,21+,23-,24+,25?,26-,29+,30+,31-,32-/m1/s1 |
| InChI Key | XTBDVXSMPXFDAU-NYBSUTBHSA-N |
Properties
| Appearance | White Powder |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. II. Structure elucidation of terpendoles A, B, C and D
X H Huang, H Nishida, H Tomoda, N Tabata, K Shiomi, D J Yang, H Takayanagi, S Omura 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.
2. Drechmerin H, a novel 1(2), 2(18)-diseco indole diterpenoid from the fungus Drechmeria sp. as a natural agonist of human pregnane X receptor
Jian-Chao Zhao, Zhi-Lin Luan, Jia-Hao Liang, Zhong-Bin Cheng, Cheng-Peng Sun, Ya-Li Wang, Meng-Yue Zhang, Tian-Yuan Zhang, Yong Wang, Tian-Mei Yang, Ying-Ying Wu, Yi-Xuan Zhang, Xin-Yu Zhao, Xiao-Chi Ma Bioorg Chem. 2018 Sep;79:250-256. doi: 10.1016/j.bioorg.2018.05.001. Epub 2018 May 9.
A novel 1(2), 2(18)-diseco indole diterpenoid, drechmerin H (1), was isolated from the fermentation broth of Drechmeria sp. together with a new indole diterpenoid, 2'-epi terpendole A (3), and a known analogue, terpendole A (2). Their structures were determined by HRESIMS, 1D and 2D NMR, ECD, and X-ray single crystal diffraction analyses as well as quantum chemical calculation. The abosulte configuration of terpendole A (2) was determined for the first time. Compound 1 displayed the significant agonistic effect on pregnane X receptor (PXR) with EC50 value of 134.91 ± 2.01 nM, and its interaction with PXR was investigated by molecular docking. Meantime, a plausible biosynthetic pathway for compounds 1-3 is also discussed in the present work.
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 ╳
