A unified and common intermediate strategy for syntheses of juglomycins and their derivatives is reported. The use of a 1,4-dimethoxynaphthalene derivative as a key intermediate enabled easy access to various juglomycin derivatives. In this study, juglomycins A–D, juglomycin C amide, khatmiamycin and its 4-epimer, and the structure proposed for juglomycin Z were synthesized from this intermediate. The absolute configuration of natural khatmiamycin has been established to be 3 R ,4 R through our synthesis. Unfortunately, the spectroscopic data for synthetic juglomycin Z were not consistent with the data reported for the natural one, strongly suggesting a structural misassignment.
Data mining is an important method for understanding various phenornena and extracting usefU1 knowledge from data , The use of data mining has become common in companies or research hlstitutes . Recently, huge amount of data call・d B ' g D ・' ・ h・ ・ been g ・i 血 g m ・ ・h ・枕・nti・n 財 g ・n ・・at 血 9 ・ ・ w b・・iness ・ PP ・伽 ・iti ・ … Big・D ・ t・・Mi ・ i・ g ・ 血 ・t i・t・ say 」 applyhlg data mining techniques to big data also have been popular . However , because big data mining poses many di 伍 culties, only sjmple analysis like aggregation has been P ・rf ・rm ・d . 0 … ea ・・ n i ・ 血 ・t the am ・unt ・ f d・t・ is s ・ 1 ・・ g ・ th・t 甘・diti ・nal d・t・ m 血 i・ g m ・th・ d i・ 血 ・ pPlicab1 ・・ An ・ th・・ reason is血at there exists not oniy persistent data 1ike customer info 皿 ation , but also dynamically generated data like sensor data or stock price data. For dynamic data , data min 洫g need to be performed in real − time, but traditional data min 血 9 methods achieve it only partially ・
Secondary metabolites in plants influence the health of herbivores such as Japanese rock ptarmigans that feed on the leaves and fruits of alpine plants. Thus, it is important to understand the secondary metabolites of alpine plants and their biological activities for conserving Japanese rock ptarmigans. We isolated C-methylflavone from the leaves of Kalmia procumbens, on which Japanese rock ptarmigans feed. Although its structure was deduced to be 8-demethyleucalyptin by comparing its NMR data with the reported ones, the possibility that the isolated compound is 6-demethyleucalyptin cannot be ruled out. Thus, both isomers were synthesized. The isolated compound was unambiguously determined to be 8-demethyleucalyptin by comparing its NMR data with those of the synthetic ones. Cytotoxic evaluation of 8- and 6-demethyleucalyptins revealed that only the former showed cytotoxicity against HCT116 and MRC-5 cells. The present study provides not only easy access to 8- and 6-demethyleucalyptins, but also their biological information.
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