Bioactivity of Latifolin and Its Derivatives against Termites and Fungi

Abstract

Latifolin (1) and its derivatives were investigated with the aim of confirming the correlation between bioactivity (antitermite and antifungal activity) and chemical structure. Termite mortality in response to the derivatives 2'-O-methyllatifolin (2), latifolin dimethyl ether (4), and latifolin diacetate (5) increased 2-fold compared to compound 1. The mortality rate from 5-O-methyllatifolin (3) was not different from 1. The mass loss (feed consumption by termite) in response to compounds 3-5 was 3 times greater than compound 1, and the mass loss from compound 2 was twice as great as compound 1. The mortality rate from compounds 4 and 5 increased sharply 7 days after initial exposure. In assessing the antifungal activity of these compounds, it was found that the inhibition rates of white- and brown-rot fungi in response to all derivatives were less than that for compound 1. Our findings indicate that the phenolic hydroxyl group at C-5 of the A ring provides antitermite activities (mortality and mass loss). In addition, both C-5 and C-2' phenolic hydroxyl groups in the A and B rings have antifungal activity against white- and brown-rot fungi. In conclusion, the bioactivity of compound 1 depends upon the position of phenolic hydroxyl groups.

Antifungal Abietane-Type Diterpenes from the Cones of Taxodium distichum Rich

“…Antifungal Assays Antifungal assays were performed according to previously published methods (Kofujita et al, 2006;Sekine et al, 2009). Before fungal inoculation, test sample was dissolved in acetone or methanol (1 mg/ml), and 600 μl of each solution were applied to the surface of each 15 ml PDA medium in a Petri dish (88 mm diam) so that the final concentration was 10 μg/cm 2 in solid agar.…”

First Total Synthesis of (±)‐Latifolin and Its Antioxidant Mechanism

“…The structure of 6 was unambiguously confirmed by X-ray crystallographic analysis (Figure 2 natural latifolin. [4] Analogues 9 and 10 were also synthesized to study the antioxidant mechanism of latifolin. As shown in Scheme 2, Pd/C-catalyzed hydrogenation of 8 gave the dihydrolatifolin (9) (91%).…”

“…[1] It has been reported to deliver a variety of biological and pharmacological activities, including inhibition of β-amyloid production, [2] antifungal, [3,4] anticarcinogenic [5] and antioxidant activity. [6] It is obvious that benzhydryl C-H bond ( Figure 1, highlighted in 1) on latifolin is very weak due to delocalization of the π electrons on the adjacent phenyl or alkenyl group.…”

Antitermite Activities of Coumarin Derivatives and Scopoletin from Protium javanicum Burm. f.

“…Each experiment was performed in triplicate. 33 termites were used per replication, and the data were averaged (N=3) Antifeedant) Activities By comparing the activity of latifolin and its derivatives, it has been suggested previously that the phenolic hydroxyl group at the C-5 position of the A ring is responsible for a compound's antitermite activities (mortality and mass loss) (Sekine et al 2009). The effect of stilbene glucosides and their related compounds on termite feeding behavior also has been investigated, with piceid exhibiting the highest feeding-deterrent effect followed by isorhapontin and astringin.…”