Lipase-catalyzed preparation of optically active 1′-acetoxychavicol acetates and their structure–activity relationships in apoptotic activity against human leukemia HL-60 cells

Antibacterial activity of Thai herbal extracts on acne involved microorganism

“…It has been reported that 1′-ACA possesses various biological activities, such as antitumor (Itokawa et al, 1987;Kondo et al, 1993;Moffatt et al, 2000;Zheng et al, 2002;Ito et al, 2005;Azuma et al, 2006;Campbell et al, 2007), anti-inflammation (Nakamura et al, 1998;Morikawa et al, 2005), antifungal (Janssen & Scheffer, 1985), antiviral (Ye & Li, 2006), antioxidative (Kubota et al, 2001), and xanthine oxidase inhibitory activity (Noro et al, 1988). Although it has been reported that the ethanol extract of A. galanga exhibits antibacterial activity against S. aureus (Oonmetta-aree et al, 2006), the antibacterial activity of 1′-ACA has not yet been reported.…”

Structural Development of Benzhydrol-Type 1'-Acetoxychavicol Acetate (ACA) Analogs as Human Leukemia Cell-Growth Inhibitors Based on Quantitative Structure-Activity Relationship (QSAR) Analysis

“…According to Azuma's report, 14) the enantiomers of ACA (1) showed the same cell-growth-inhibitory activity towards HL-60 cells. We also compared the cell-growth-inhibitory activities of the enantiomers of our compound 3m.…”

“…Azuma et al recently reported structure-activity relationship studies of ACA (1) for apoptotic activity towards human leukemia HL-60 cells, 14) showing that (i) the two acetyl groups and the unsaturated double bond between the Cb and Cg positions of ACA (1) are essential for the activity, and (ii) the configuration at the a-position of ACA (1) does not affect the activity. Based on these results, we synthesized several ACA (1) analogs and examined their cell-growth-inhibitory activity using human leukemia HL-60 cells.…”

“…Briefly, the hydroxyl group of 4-hydroxybenzaldehyde (9) was protected with tert-butyldimethylchlorosilane (TBS-Cl), followed by treatment with appropriate Grignard or aryllithium reagents (generated from aryl bromide by treatment with n-butyllithium) to afford the intermediates 11a-d. Deprotection of the TBS group was performed with tetra-n-butylammonium fluoride (TBAF), and then acetylation with acetic anhydride afforded 3a-d. On the other hand, protection of the hydroxyl group of 4-bromophenol (14) with TBS-Cl, followed by treatment with n-butyllithium, gave aryllithium species, which were quenched with various benzaldehydes to give intermediates 11e-h and 13a. Deprotection of the TBS group with TBAF, and successive acetylation with acetic anhydride afforded 3e-h and 5a.…”

Chemoenzymatic Approach to Enantiomerically Pure (R)‐3‐Hydroxy‐3‐methyl‐4‐pentenoic Acid Ester and Its Application to a Formal Total Synthesis of Taurospongin A

“…As either the diastereomeric pair of alcohols 9a or acetates 9b were hardly separable on silica gel column chromatography, we decided to use a lipase-catalyzed kinetic resolution of the diastereomers of 9b. The two candidates for enzymes which so far had been reported to satisfy such requrements, the stereoselective hydrolysis of allylic acetates, Pseudomonas cepacia lipase [26,27] and Candida antarctica lipase [28] were com- …”