Characterization of (-)-Matairesinol as a Potent Inhibitor of Casein Kinase I in Vitro.

Abstract

The inhibitory effects of (-)-matairesinol (MTS) isolated from Thujopsis dolabrata var. hondai on the activities of four distinct Ser/Thr-protein kinases [two casein kinases (CK-I and CK-II), A-kinase and C-kinase] were determined in vitro. It was found that (i) MTS inhibits the activities of CK-I and C-kinase alpha (ID(50)=approx. 10 microM) in a dose-depedent manner, but high doses are required to inhibit A-kinase activity (ID(50)=approx. 90 microM); (ii) the autophosphorylation of CK-I is more sensitive to MTS (ID(50)=approx. 0.2 microM); (iii) MTS inhibits CK-I activity in a manner similar to that observed with CK-I-7 (a CK-I inhibitor); and (iv) the compound inhibits CK-I activity by affecting ATP binding in a mixed type manner. These results indicate that MTS is a potent CK-I inhibitor in vitro.

Isolation of (−)-4′-demethyl traxillagenin from Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino

“…An acidic part of the chloroform extract was chromatographed on Florisil eluted with chloroform-methanol (v/v = 50/1-1/1), followed by prep-TLC developed with chloroform-methanol (v/v = 40/1), CH 2 Cl 2 -THF (v/v = 15/1) and then n-hexane-ethyl acetate (v/v = 1/1) to afford (-)-4 0 -demethyl traxillagenin (1, 19.9 mg); its spectral data and specific rotation agreed well with the data reported for 1 [6]. From this plant material, other than compound 1, vanillin (2, 0.0006% yield), coniferyl aldehyde (3, 0.0006% yield), and eugenol (4, 0.0002% yield) were isolated from acidic part of the chloroform extract and the existence of syringaldehyde (5) was confirmed by high-performance liquid chromatography (HPLC) analysis. These compounds are closely related in lignan biosyntheses.…”

“…hondai Makino (Cupressaceae) is a needle-leaf tree found naturally only in the northern part of Japan. From this plant, a number of neutral terpenoids [1-3] and several acidic phenols, tropolones, and lignans were isolated [4,5].In this paper, we report the isolation of (-)-4 0 -demethyl traxillagenin and some related compounds from the sawdust of T. dolabrata var. hondai.…”

“…hondai Makino (Cupressaceae) is a needle-leaf tree found naturally only in the northern part of Japan. From this plant, a number of neutral terpenoids [1][2][3] and several acidic phenols, tropolones, and lignans were isolated [4,5].…”

Inhibition of Akt signaling by the lignan matairesinol sensitizes prostate cancer cells to TRAIL-induced apoptosis

“…The molecular mechanism behind anticancer activity of lignans is not yet well characterized. Lignans have been reported to induce downregulation of the anti-apoptotic Bcl-2 proteins (Hausott et al, 2003) and to inhibit casein kinase II and protein kinase C a (Yokoyama et al, 2003). They can act as antioxidants protecting cells from oxidative stress (Kitts et al, 1999), or as inhibitors of steroid metabolizing Lignans sensitize prostate cancer cells to TRAIL E Peuhu et al enzymes (Adlercreutz et al, 1993).…”

A preparative isolation and purification of arctigenin and matairesinol fromForsythia koreana by centrifugal partition chromatography

“…In addition to antitumor and antiviral activities, arctigenin shows antitumor promoting, anti-inflammatory, hepatoprotective, immunoregulatory, neuroprotective, and phytoestrogenic properties [7 -10]. Matairesinol exerted potent inhibitory activities on casein kinase I [11] and inhibited HIV replication in H9 lymphocyte cells [12]. The fruits of F. koreana are used as an antipyretic and anti-inflammatory agent for the treatment of bacterial infections, and phenolic glycosides, lignans, and triterpenes have been isolated and identified [13].…”