Ustusolate E
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| Category | Bioactive by-products |
| Catalog number | BBF-04372 |
| CAS | 1175543-06-2 |
| Molecular Weight | 374.43 |
| Molecular Formula | C21H26O6 |
| Purity | 93.0% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04372 | 1 mg | $629 | In stock |
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Add to cartDescription
Ustusolate E is a metabolite of marine-derived fungus Aspergillus ustus 094102. Ustusolate E exhibits cytotoxic activity against A549 and HL-60 cell lines.
Specification
| Synonyms | 9α-hydroxy-6β-(6-oxohex-2E,4E-dienoyloxy)-5α-drim-7-en-11,12-olide; 2,4-Hexadienoic acid, 6-oxo-, (5R,5aS,9aS,9S)-1,3,5,5a,6,7,8,9,9a,9b-decahydro-9b-hydroxy-6,6,9a-trimethyl-1-oxonaphtho[1,2-c]furan-5-yl ester, (2E,4E)- |
| Storage | Store at 2-8°C |
| IUPAC Name | [(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] (2E,4E)-6-oxohexa-2,4-dienoate |
| Canonical SMILES | CC1(CCCC2(C1C(C=C3C2(C(=O)OC3)O)OC(=O)C=CC=CC=O)C)C |
| InChI | InChI=1S/C21H26O6/c1-19(2)9-7-10-20(3)17(19)15(27-16(23)8-5-4-6-11-22)12-14-13-26-18(24)21(14,20)25/h4-6,8,11-12,15,17,25H,7,9-10,13H2,1-3H3/b6-4+,8-5+/t15-,17+,20+,21+/m1/s1 |
| InChI Key | NTEIYTQTTHYBTI-BEFOBABASA-N |
Properties
| Appearance | Amorphous Powder |
| Boiling Point | 549.1±50.0°C (Predicted) |
| Density | 1.24±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. 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.
2. Sesquiterpenoids and benzofuranoids from the marine-derived fungus Aspergillus ustus 094102
Zhenyu Lu, Yi Wang, Chengdu Miao, Peipei Liu, Kui Hong, Weiming Zhu J Nat Prod. 2009 Oct;72(10):1761-7. doi: 10.1021/np900268z.
Eight drimane sesquiterpenes (1-8), six isochromane derivatives (9-14), and three known compounds, daldinin B (15), 9alpha-hydroxy-6beta-[(2E,4E,6E)-octa-2,4,6-trienoyloxy]-5alpha-drim-7-en-11,12-olide (16), and pergillin (17), were isolated from the EtOAc extract of the marine-derived fungus Aspergillus ustus 094102. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The cytotoxic effects on A549 and HL-60 cell lines were evaluated by SRB and MTT methods. Ustusorane E (13) showed significant cytotoxicity against HL-60 cells with an IC50 value of 0.13 microM. Ustusolates C (6) and E (8) exhibited moderate cytotoxicity against A549 and HL-60 cells with IC50 values of 10.5 and 9.0 microM, respectively, and ustusolate A (4) showed weak cytotoxicity against HL-60 and A549 cells with IC50 values of 20.6 and 30.0 microM, respectively.
3. Cytotoxic Drimane-Type Sesquiterpenes from Co-Culture of the Marine-Derived Fungi Aspergillus carneus KMM 4638 and Beauveria felina (= Isaria felina) KMM 4639
Olesya I Zhuravleva, Elena B Belousova, Galina K Oleinikova, Alexandr S Antonov, Yuliya V Khudyakova, Anton B Rasin, Roman S Popov, Ekaterina S Menchinskaya, Phan Thi Hoai Trinh, Anton N Yurchenko, Ekaterina A Yurchenko Mar Drugs. 2022 Sep 19;20(9):584. doi: 10.3390/md20090584.
Chemical investigation of a coculture of the marine-derived fungi Beauveria felina KMM 4639 and Aspergillus carneus KMM 4638 led to the identification of three new drimane-type sesquiterpenes, asperflavinoids B, D and E (2, 4, 5), and nine previously reported related compounds. The structures of these compounds were established using spectroscopic methods and by comparison with known analogues. We also investigated the cytotoxic activity of the isolated compounds against several cancer and normal cell lines. Asperflavinoid C (3) and ustusolate E (9) exerted a significant effect on human breast cancer MCF-7 cell viability, with IC50 values of 10 µM, and induced in caspase-dependent apoptosis and arrest of the MCF-7 cell cycle in the G2/M phase in these cells.
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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 ╳
