Ustusol A
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| Category | Others |
| Catalog number | BBF-04371 |
| CAS | 1175543-02-8 |
| Molecular Weight | 268.35 |
| Molecular Formula | C15H24O4 |
| Purity | 98.0% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04371 | 1 mg | $629 | In stock |
Online Inquiry
Add to cartDescription
Ustusol A is produced by the strain of Aspergillus ustus.
Specification
| Synonyms | (3S,5S,9R,10S)-3,9,11-trihydroxydrim-7-en-6-one; 3β,9α,11-trihydroxy-6-oxodrim-7-ene; 1(4H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-4,7-dihydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-, (4R,4aS,7S,8aS)- |
| Storage | Store at 2-8°C |
| IUPAC Name | (4R,4aS,7S,8aS)-4,7-dihydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydronaphthalen-1-one |
| Canonical SMILES | CC1=CC(=O)C2C(C(CCC2(C1(CO)O)C)O)(C)C |
| InChI | InChI=1S/C15H24O4/c1-9-7-10(17)12-13(2,3)11(18)5-6-14(12,4)15(9,19)8-16/h7,11-12,16,18-19H,5-6,8H2,1-4H3/t11-,12-,14-,15+/m0/s1 |
| InChI Key | YMOQABSTCGJNMC-NZBPQXDJSA-N |
Properties
| Appearance | Powder |
| Boiling Point | 436.8±45.0°C (Predicted) |
| Density | 1.165±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Cadinane- and drimane-type sesquiterpenoids produced by Paecilomyces sp. TE-540, an endophyte from Nicotiana tabacum L., are acetylcholinesterase inhibitors
Kuo Xu, Qi Zhou, Xiu-Qi Li, Tian Luo, Xiao-Long Yuan, Zhong-Feng Zhang, Peng Zhang Bioorg Chem. 2020 Nov;104:104252. doi: 10.1016/j.bioorg.2020.104252. Epub 2020 Sep 2.
Sesquiterpenoids with diverse skeleton types are regarded as potential lead compounds in pharmacological and other applications. Herein, we report the discovery of two new cadinane-type sesquiterpenoids, paecilacadinol A (1) and B (2); two new drimane-type sesquiterpenoids, ustusol D (3) and ustusol E (4); and six known analogs (5-10) from the endophytic fungus Paecilomyces sp. TE-540, enriching the structural diversity of naturally occurring sesquiterpenoids. Their planar structures were determined on the basis of detailed interpretation of 1D and 2D NMR spectroscopy and HRESIMS data, while their stereochemical structures were established by X-ray crystallographic analyses for 1 and 3-8 and theoretical calculations for 2. Notably, compounds 1 and 2 represent novel examples of cadinane-type sesquiterpenoids with ether bonds formed by intramolecular dehydration. Compounds 5 and 6 showed moderate activities against acetylcholinesterase (AChE), with IC50 values of 43.02 ± 6.01 and 35.97 ± 2.12 μM, respectively. Docking analysis predicted that 5 bound well in the catalytic pocket of AChE via hydrophobic interactions with Trp84, Gly117, Ser122, and Tyr121 residues, while 6 was located with Asp72 and Ser122 residues.
2. Sesquiterpenoids from the Mangrove-Derived Aspergillus ustus 094102
Pengyan Gui, Jie Fan, Tonghan Zhu, Peng Fu, Kui Hong, Weiming Zhu Mar Drugs. 2022 Jun 22;20(7):408. doi: 10.3390/md20070408.
Four new drimane sesquiterpenoids (1-4) and three known ones (5-7) were isolated from the fermentation broth of the mangrove-derived Aspergillus ustus 094102. Compound 5 was further resolved as four purified compounds 5a-5d. By means of extensive spectroscopic and ECD analysis as well as the chemical transformation, their structures were identified as (2R,3R,5S,9R,10S)-2,3,9,11-tetrahydroxydrim-7-en-6-one (ustusol F, 1), (2R,3R,5R,9S,10R)-2,3,11-trihydroxydrim-7-en-6-one (9-deoxyustusol F, 2), (3S,5R,9R,10R)-3,11,12-trihydroxydrim-7-en-6-one (ustusol G, 3), (5S,6R,9S,10S, 11R,2'E,4'E)-(11-dideoxy-11-hydroxystrobilactone A-6-yl)-5-carboxypenta-2,4-dienoate (ustusolate H, 4), ((5S,6R,9S,10S)-strobilactone A-6-yl) (2E,4E)-6,7-dihydroxyocta-2,4-dienoate (ustusolate I, 5), (2'E,4'E;6',7'-erythro)-ustusolate I (5a) and (2'E,4'E;ent-6',7'-erythro)-ustusolate I (5b), (2'E,4'E,6'R,7'R)-ustusolate I (5c) and (2'E,4'E,6'S,7'S)-ustusolate I (5d), (5S,6R,9S,10S,2'E,4'E)-(strobilactone A-6-yl)-5-carboxypenta-2,4-dienoate (ustusolate J, 6), and (2S,5S,9R,10S)-2,9,11-trihydroxydrim-7-en-6-one (ustusol B, 7), respectively. Compound 5 showed antiproliferation against the human tumor cells CAL-62 and MG-63 with the IC50 values of 16.3 and 10.1 µM, respectively.
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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 ╳
