Gibberellin A23 in immature seeds of lupinus luteus

✍ Scribed by Koichi Koshimizu; Hiroshi Fukui; Makoto Inui; Yukiyoshi Ogawa; Tetsuo Mitsui

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 269 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)98908-7

✦ Synopsis

Gibberellin-like substances have been shown to occur in iss&ure seeds of Lupinus Zuteus (1-4) and an attempt was made to purify two active principles, which were tentatively named as Lupinus gibberellin I and II (5)

. The former structure, whose provisional name was ** renamed as gibberellin Al8 , has been reported previously (6) .

In this communication we wish to present evidence for the structure and stereochemistry of the latter C-20 Gibberellin, now named gibberellin A23. GA23, (II) was isolated from the acidic fraction of the seeds in yield of ca. 0.04% by the same extraction procedure reported previously (6) .

It was not crystallizable from the usual solvents, which gave an amorphous solid (m.p. 185-go). However, this material was homogeneous on TLC and afforded only a single derivative on esterification and sodium borohydride *RX reduction. It showed a purple fluorescent spot at RCA 0.68 in system A and 0.60 in system **** 3 B on TLC of silica gel G under UV light after spraying with 5% sulphuric acid-ethanol and heating, and showed a yellow spot with 0.5% aqueous solution of potassium pemdngmte.

The IR spectrum (KBr) indicated the presence of hydroxyls (3500-3300 br. -l) and cm carboxyls (2800-2500 br. and 1708 br. cm -1) . On treatment with diazcmethane (II) gave a *