Strong acid-promoted skeletal remodeling of the aphid pigment: red uroleuconaphin to green viridaphin

Chiharu Ozakai; Kei Kitamura; Mitsuyo Horikawa; To-sho Hoshiyama; Akari Imamura; Tatsuro Yoneyama; Akemi Umeyama; Masaaki Noji; Tetsuto Tsunoda; Hiroto Kaku

doi:10.1039/D1NJ05261F

Strong acid-promoted skeletal remodeling of the aphid pigment: red uroleuconaphin to green viridaphin†

Chiharu Ozakai,^a Kei Kitamura,

*^a Mitsuyo Horikawa,^a To-sho Hoshiyama,^a Akari Imamura,^a Tatsuro Yoneyama,^a Akemi Umeyama,^a Masaaki Noji,^a Tetsuto Tsunoda^a and Hiroto Kaku

*^a

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^a Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan
E-mail: kkitamura@ph.bunri-u.ac.jp, kaku@ph.bunri-u.ac.jp

Abstract

We present herein a strong acid-promoted single-step transformation of red uroleuconaphin A₁ into green viridaphin A₂. Viridaphin A₁ and bis-naphthoquinone were also obtained by performing the reaction in aqueous media. The optical properties were studied to determine the absolute stereochemistry of viridaphins A₁ and A₂ by comparison with those obtained from naturally occurring aphid pigments. The photophysical and antimicrobial activities of those green pigments were also studied.

New Journal of Chemistry

Strong acid-promoted skeletal remodeling of the aphid pigment: red uroleuconaphin to green viridaphin†

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Strong acid-promoted skeletal remodeling of the aphid pigment: red uroleuconaphin to green viridaphin

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