Methyllinderone

Nat. Prod. Sci., 2002, 8(3):100-2.

Cytotoxicity of Lignans from Lindera erytheroca.[Reference: WebLink]

METHODS AND RESULTS:
Three lignans were isolated from a methanol extract of Lindera erytherocarpa Makino (Lauraceae) are evaluated in vitro cytotoxicity using three cancer cell line assay. The compounds were identified as Methyllinderone (1), linderone (2), and kanakugiol (3) by spectroscopic methods.
CONCLUSIONS:
Amongst the compounds, Methyllinderone (1) showed significant cytotoxicity against mouse melanoma (B16-FlO), human acetabulum fibrosarcoma (HT1080), and choronic myelogenous leukemia (K562) cancer cell lines with values of 2.2, 2.5, 8.3 , respectively.

Planta Med. 2007 Jun;73(7):679-82.

Inhibition of chitin synthase 2 and antifungal activity of lignans from the stem bark of Lindera erythrocarpa.[Pubmed: 17538872]

METHODS AND RESULTS:
Potent chitin synthase 2 inhibitors, Methyllinderone (1), linderone (2) and kanakugiol (3) were isolated from the stem bark of L. erythrocarpa Makino (Lauraceae). These compounds inhibited chitin synthase 2 with IC(50) values of 23.3, 21.4 and 23.8 microg/mL, respectively. Methyllinderone (1) and linderone (2) exhibited no inhibitory activities for chitin synthases 1 and 3 from S. cerevisiae, and chitin synthase 1 from Candida albicans up to the concentration of 280 microg/mL, while kanakugiol (3) exhibited very weak activity against chitin synthase 1 of C. albicans with an IC(50) of 160 microg/mL. All of the compounds showed moderate to weak antifungal activities against various pathogenic fungi (MIC: 8 - >128 microg/mL) including Cryptococcus neoformans, Aspergillus fumigatus, and Colletotrichum lagenarium.
CONCLUSIONS:
The results indicate that these compounds are specific inhibitors of chitin synthase 2 and can potentially serve as antifungal agents.

Bioorg Med Chem. 2005 Nov 15;13(22):6182-7.

Cyclopentenediones, inhibitors of farnesyl protein transferase and anti-tumor compounds, isolated from the fruit of Lindera erythrocarpa Makino.[Pubmed: 16055336]

METHODS AND RESULTS:
Four cyclopentenediones, farnesyl protein transferase inhibitors, and anti-tumor compounds were isolated from the methanolic extract of the fruits of Lindera erythrocarpa Makino (Lauraceae). The structure of the compounds was determined by spectral data including NMR and mass spectrometry, and cyclopentenediones such as Methyllinderone (1), methyllucidone (2), lucidone (3), and linderone (4) were identified by comparing their reported spectral data with that of the literature values. Compounds 1-4 inhibited farnesyl protein transferase with IC50 value of 55.3+/-4.1, 42+/-1.9, 103+/-5.1, and 40+/-3.5 microM, respectively.
CONCLUSIONS:
Isolated compounds also inhibited the growth of various human cancer cell lines in a dose-dependent manner. Especially, Methyllinderone and methyllucidone selectively inhibited the growth of H-ras-transformed rat-2 cell lines in comparison with normal rat-2 cells with a GI50 value of 0.3 and 0.85 microM, respectively.

Contrib Nephrol. 1987;56:53-9.

The importance of the renal interstitium for kidney function.[Reference: WebLink]

Total synthesis of human chymase inhibitor Methyllinderone has been achieved in only four steps with an overall yield of 21% from dimethyl squarate.
METHODS AND RESULTS:
We developed an efficient synthetic method for obtaining Methyllinderone derivatives and found the active compound. In addition, we propose the inhibition mechanism of the active compound against human chymase using calculations.

Mol. Phys., 2015, 113(7):683-97.

Conformational, electronic and antioxidant properties of lucidone, linderone and methyllinderone: DFT, QTAIM and NBO studies.[Reference: WebLink]

Theoretical studies on lucidone, linderone and Methyllinderone were performed to investigate factors that contribute to structural stability and to elucidate the antioxidant properties and mechanisms.
METHODS AND RESULTS:
The study was performed in different media utilising the density functional theory with different functionals and the 6-311+ G(d,p) basis set. The antioxidant activity has been considered through the electron transfer and metal chelation mechanisms. The results show that the stability of the tautomers and conformers is due to the presence of several intramolecular hydrogen bonds. The ionisation potential values suggest that the antiradical activity increases with the increase in the number of OCH3 groups substituted on the cyclopentene-1,3-dione ring. In vacuo, the spin density of the Fe(II) cation upon ligand coordination decreases to 3.0−3.5, whereas the ligand spin density approaches 1, indicating that it is oxidised to a radical cation.
CONCLUSIONS:
The metal ion affinity (MIA) is influenced by the position and number of OCH3 substituted on the acylcyclopentene-1,3-dione ring. A very favourable MIA, in vacuo, is obtained when Fe(II) is chelated between the sp2 O and sp3 O atoms. An estimation of MIA in an aqueous solution shows a remarkable decrease with respect to the results in vacuo.