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. 2010;86(3):176-89.
doi: 10.2183/pjab.86.176.

Cytotoxic substances from two species of Japanese sea hares: chemistry and bioactivity

Kiyoyuki Yamada  1 , Makoto Ojika, Hideo Kigoshi, Kiyotake Suenaga
Affiliations

Cytotoxic substances from two species of Japanese sea hares: chemistry and bioactivity

Kiyoyuki Yamada et al. Proc Jpn Acad Ser B Phys Biol Sci. 2010.

Abstract

From the sea hares belonging to two genera, Aplysia and Dolabella, a variety of new cytotoxic substances were isolated as minute constituents: their chemical structures were determined and their cytotoxicity was evaluated. Regarding the highly cytotoxic substances, further chemical and biological studies were performed that included their asymmetric chemical synthesis and elucidation of biological characteristics such as antitumor activity.

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Figures

Fig. 1
Fig. 1
Structures and cytotoxicity of aplyronines A-H (1–8).
Fig. 2
Fig. 2
Structure-activity relationships of aplyronine A (1) and its analogs.
Fig. 3
Fig. 3
(a) Structure of the actin-aplyronine A (1) complex; (b) the same complex rotated by ca. 90°.
Fig. 4
Fig. 4
Cytotoxic substances (25–27) from the sea hare A. kurodai and highly cytotoxic substances (28–31) from the sea hare D. auricularia.
Fig. 5
Fig. 5
Cytotoxic peptides and depsipeptides from the sea hare D. auricularia.
Fig. 6
Fig. 6
Cytotoxic polyketides from the sea hare D. auricularia.
Fig. 7
Fig. 7
Cytotoxic terpenoids from the sea hare D. auricularia.
Scheme 1
Scheme 1
Isolation procedure for aplyronines A-H (1–8).
Scheme 2
Scheme 2
Outline of the asymmetric chemical synthesis of aplyronine A (1).
None
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