幹樹皮に由来するポリプレニル化ベンゾイルフロログルシノール類のピカラーヒゾンA-H

Picrorhizones A-H, Polyprenylated Benzoylphloroglucinols from the Stem Bark of .

• Edwin R Sukandar
• Sutin Kaennakam
• Thammarat Aree
• Xuehong Nöst
• Kitiya Rassamee
• Rudolf Bauer
• Pongpun Siripong
• Taslim Ersam
• Santi Tip-Pyang

抄録

新規なポリプレニル化ベンゾイルフロログルシノール誘導体(-)を8種、既知の類似体(-)を4種単離し、その構造を分光データ解析(1D, 2D NMR, HRESIMS)により決定し、単結晶X線回折と実験および計算されたECDデータを組み合わせて絶対配置を決定した。これらの新規代謝物は、シクロブチルを含む側鎖を有するベンゾイルフロログルシノールの稀有な例である。単離された化合物は、5種類のヒト癌細胞（KB, HeLa S3, MCF-7, Hep G2, HT-29）に対する細胞毒性、およびCOX-1およびCOX-2酵素に対する阻害活性を評価した。細胞毒性の結果、化合物はKB、HeLa S3、MCF-7及びHep G2癌細胞に対して活性を示し、IC値は5.9〜9.4μMであった。シクロオキシゲナーゼ阻害試験を行った化合物の中で，COX-1に対する阻害効果が最も高い化合物（20μMで35.2±9.6%阻害）が得られた。

Eight new polyprenylated benzoylphloroglucinol derivatives (-) and four known analogues (-) were isolated from the stem bark of . Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and the absolute configurations were established by single-crystal X-ray diffraction combined with experimental and calculated ECD data. The new metabolites represent rare examples of benzoylphloroglucinols bearing a cyclobutyl-containing side chain. The isolated compounds were evaluated for their cytotoxic properties against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29 cells) and their inhibitory activities against COX-1 and COX-2 enzymes. The cytotoxicity results showed that compound was active against KB, HeLa S3, MCF-7, and Hep G2 cancer cells, with IC values ranging from 5.9 to 9.4 μM. Among the compounds tested for cyclooxygenase inhibition, compound possessed the highest inhibitory effect toward COX-1 (35.2 ± 9.6% inhibition at 20 μM).