✦ LIBER ✦

Structures of gibberellins A26 and A27 in immature seeds of pharbitis nil

✍ Scribed by Nobutaka Takahashi; Takao Yokota; Noboru Murofushi; Saburo Tamura

Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 222 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)88089-8

No coin nor oath required. For personal study only.

✦ Synopsis

Isolation and. biological activities of new gibberellins A26 and A27 in immature seeds of the Japanese morning-glory (Pharbitis nil) have been reported -

(1). We wish to report here the elucidation of their structures.

Gibberellin A26 (GA26), m.p. 254-257", formed a monomethyl ester (II), m.p. 207-211'. The high resolution mass spectrum of II reveales a parent ion peak at m/e 376.159 with the composition C20H2407 (calcd. 376.152). Therefore GA26 has the molecular formula C19H2207. The significant peaks at M-32 (CH40) and M-60 (C2H402) in the mass spectrum of II, together with an AB quartet due to the C-10, C-1Oa protons centered at T 7.27 and 'c 6.63 (J=lOcps) in its NMR spectrum (CDC13), suggest that GA26 retains the structural features common to the known gibberellins. As summarized in Table I, the functional groups of II are deduced on the basis of the IR, W and NMR spectra. GA26 rapidly consumed periodate and easily formed a diacetate (III), m.p. 209-210°, having no free hyaroxyl group. These suggest the presence of C-2 is indicated by the CDC13; t 8.50 in C5D5N) C5D5N) in the change of a cis-1,2-glycol system in GA26. -An axial hydroxyl at down-field shifts of the C-l methyl singlet (t 8.79 in and. the C-1Oa proton doublet (T 6.63 in CDC13; 6.09 in the solvent from CDC13 to C5D5N (2). Therefore the other hydroxyl must be attached to C-3 in the equatorial conformation. The C-2 proton doublet at t 6.25 (J=$.O cps) rationalizes the existence of a hydroxyi substituent at C-3 and the equatorial cocformation of.the C-3 hydroxyl is supported by the C-3 proton multiplet with a large width (20 cps) characteristic of an axial proton. The pattern of &OH region is very similar to that of GA8. Therefore GA26 ccntains a C-22, C-3g-glycol.

📜 SIMILAR VOLUMES

Gibberellin in immature seeds of pharbit

Gibberellin in immature seeds of pharbitis nil

✍ Nobutaka Takahashi; Noboru Murofushi; Takao Yokota; Saburo Tamura 📂 Article 📅 1967 🏛 Elsevier Science 🌐 French ⚖ 205 KB

The presence of glbberellln-like substances in immature seeds of morning-glory (Pharbltis a) has been suggested by Ogawa ! (1,2), Murakami (3) and Zeevaat (4). Now we wish to report the Isolation and structure of a new gibberellln, tentatively named Pharbltis Gibberellln, as well as the presence o

Structure of new gibberellin glucoside i

Structure of new gibberellin glucoside in immature seeds of Pharbitis nil

✍ Takao Yokota; Noboru Murofushi; Nobutaka Takahashi 📂 Article 📅 1970 🏛 Elsevier Science 🌐 French ⚖ 158 KB

We have isolated seven gibberellin glucosides (1, 2) from immature seeds of morning-glory (Pharbitis nil) and elucidated the structures of six of them - (3). Now we wish to report the structure of a new gibberellin glucoside, tentatively termed F-VII.

Stuructures of new gibberellin glucoside

Stuructures of new gibberellin glucosides in immature seeds of pharbitis nil

✍ Takao Yokota; Nobutaka Takahashi; Noboru Murofushi; Saburo Tamura 📂 Article 📅 1969 🏛 Elsevier Science 🌐 French ⚖ 209 KB

On the treatment with acetic anhydride-pyridine at room temparature the four glucosldes gave the ccrresponding acetates. Chemical shifts in the NMR spectra of the glucosides and their acetates are summarized in Table. Esterification of a crystalline F-II tetraacetate (II), Cj~H40015H20\*\*, m.p. 20

Isolation of gibberellins A26and A27and

Isolation of gibberellins A26and A27and their glucosides from immature seeds ofPharbitis nil

✍ Takao Yokota; Nobutaka Takahashi; Noboru Murofushi; Saburo Tamura 📂 Article 📅 1969 🏛 Springer-Verlag 🌐 English ⚖ 208 KB

Two new gibberellins, gibberellins Ae6 and Ae~ (GA2~ and GA2:), and their glucosides have been isolated from immature seeds of Japanese morning-glory (Pharbiti8 nil), together with GA s and its glucoside. GA~6, GA2~ and their glucosides showed only slight growth-promoting activities on seedlings of

Structures of new gibberellins in immatu

Structures of new gibberellins in immature seeds of canavalia gladiata

✍ Nobutaka Takahashi; Noboru Murofushi; Tokao Yokota; Saburo Tamura; Jiro Kato; Yo 📂 Article 📅 1967 🏛 Elsevier Science 🌐 French ⚖ 223 KB

Isolation and biological aotivlties of two novel gibberellins, Canavalla gibberellln-I and -11 (CG-I, CG-II) contained in Immature seeds of sword bean (Canavalia aladiata DC.) have been already reported (1). In this paper we wish to report the determination of their structures.

Gibberellin A23 in immature seeds of lup

Gibberellin A23 in immature seeds of lupinus luteus

✍ Koichi Koshimizu; Hiroshi Fukui; Makoto Inui; Yukiyoshi Ogawa; Tetsuo Mitsui 📂 Article 📅 1968 🏛 Elsevier Science 🌐 French ⚖ 269 KB

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