Lucilactaene
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02275 |
| CAS | |
| Molecular Weight | 401.45 |
| Molecular Formula | C22H27NO6 |
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Description
It is produced by the strain of Fusarium sp. RK-97-94. It is a P53-transfected tumor cell cycle inhibitor. It inhibits the cell cycle progression of H1299/TSP53 in G1 phase.
Specification
| IUPAC Name | methyl (2E,3E,5E,7E,9E)-11-[(3aS,6S,6aR)-3a-hydroxy-5-oxo-3,4,6,6a-tetrahydro-2H-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoate |
| Canonical SMILES | CC=C(C=C(C)C=CC=CC=C(C)C(=O)C1C2C(CCO2)(NC1=O)O)C(=O)OC |
| InChI | InChI=1S/C22H27NO6/c1-5-16(21(26)28-4)13-14(2)9-7-6-8-10-15(3)18(24)17-19-22(27,11-12-29-19)23-20(17)25/h5-10,13,17,19,27H,11-12H2,1-4H3,(H,23,25)/b8-6+,9-7+,14-13+,15-10+,16-5+/t17-,19-,22+/m1/s1 |
| InChI Key | XJKYTYUOGYTPSB-HZDMFNNQSA-N |
Properties
| Appearance | Pale Yellow Amorphous Solid |
| Solubility | Soluble in Methanol |
Reference Reading
1. Isolation of new lucilactaene derivatives from P450 monooxygenase and aldehyde dehydrogenase knockout Fusarium sp. RK97-94 strains and their biological activities
Islam A Abdelhakim, Takayuki Motoyama, Toshihiko Nogawa, Fauze Bin Mahmud, Yushi Futamura, Shunji Takahashi, Hiroyuki Osada J Antibiot (Tokyo). 2022 Jul;75(7):361-374. doi: 10.1038/s41429-022-00529-3. Epub 2022 Apr 28.
Fusarium sp. RK97-94 is a producer of potent antimalarial compounds such as lucilactaene and its derivatives. The biosynthetic gene cluster of lucilactaene was identified but only a knockout mutant of methyltransferase (luc1) was reported in previous papers. Herein, we report on isolation and identification of prelucilactaene G (1), and prelucilactaene H (2) from the aldehyde dehydrogenase knockout strain (∆luc3) culture broth, as well as prelucilactaene A (3), prelucilactaene B (4), and two isomeric mixtures of prelucilactaene E (5) and prelucilactaene F (6), from the P450 monooxygenase knockout strain (∆luc2) culture broth. Our data, unlike the previous ones, suggest the involvement of the aldehyde dehydrogenase (Luc3) in lucilactaene biosynthesis, and support the involvement of the P450 monooxygenase (Luc2) in C-20 hydroxylation rather than C-13-C-14 epoxidation or C-15 hydroxylation. Isolated compounds displayed moderate to strong antimalarial activities, and the structure-activity relationship of lucilactaene derivatives was examined.
2. Biosynthetic gene cluster identification and biological activity of lucilactaene from Fusarium sp. RK97-94
Sho Kato, Takayuki Motoyama, Yushi Futamura, Masakazu Uramoto, Toshihiko Nogawa, Toshiaki Hayashi, Hiroshi Hirota, Akira Tanaka, Naoko Takahashi-Ando, Takashi Kamakura, Hiroyuki Osada Biosci Biotechnol Biochem. 2020 Jun;84(6):1303-1307. doi: 10.1080/09168451.2020.1725419. Epub 2020 Feb 11.
We identified the biosynthetic gene cluster for lucilactaene, a cell cycle inhibitor from a filamentous fungus Fusarium sp. RK 97-94. The luc1 knockout strain accumulated demethylated analogs, indicating the involvement of Luc1 methyltransferase in lucilactaene biosynthesis. Lucilactaene showed potent antimalarial activity. Our data suggested that methylation and ether ring formation are essential for its potent antimalarial activity.
3. Dihydrolucilactaene, a Potent Antimalarial Compound from Fusarium sp. RK97-94
Islam A Abdelhakim, Fauze Bin Mahmud, Takayuki Motoyama, Yushi Futamura, Shunji Takahashi, Hiroyuki Osada J Nat Prod. 2022 Jan 28;85(1):63-69. doi: 10.1021/acs.jnatprod.1c00677. Epub 2021 Dec 24.
A recently discovered secondary metabolism regulator, NPD938, was used to alter the secondary metabolite profile in Fusarium sp. RK97-94. Three lucilactaene analogues were detected via UPLC-ESI-MS analysis in NPD938-treated culture. The three metabolites were successfully purified and identified as dihydroNG391 (1), dihydrolucilactaene (2), and 13α-hydroxylucilactaene (3) via extensive spectroscopic analyses. DihydroNG391 (1) exhibited weak in vitro antimalarial activity (IC50 = 62 μM). In contrast, dihydrolucilactaene (2) and 13α-hydroxylucilactaene (3) showed very potent antimalarial activity (IC50 = 0.0015 and 0.68 μM, respectively). These findings provide insight into the structure-activity relationship of lucilactaene and its analogues as antimalarial lead compounds.
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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 ╳
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