Metabolism of GA9 methyl ester in a culture of prothallia of Lygodium japonicum.

Two successful and two unsuccessful synthetic routes are described for the conversion of commercially available fungal gibberellins to the antheridiogen GA73 methyl ester (5), originally isolated from gametophytes of the fern Lygodium japonicum. The more efficient route began with the Birch reduction of either the GA7 derivative (31) or methyl gibberellate 3,13-dimesylate (32) to give the ∆1(10),16-diene acid (33), which was converted into the ∆1,9-diene acid (40) by means of a four step procedure. This intermediate could be selectively hydrogenated to the ∆9-ene derivative which underwent iodolactonization and then elimination of HI to afford enone (29), Wittig methylenation of which furnished the target antheridiogen (5). In addition, (29) was functionalized at C12 by free radical bromination to give access to the 12β-hydroxy derivative of (5), i.e. (6), a new antheridiogen isolated from Lygodium circinnatum.

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Biological Activities of the Methyl Ester of Gibberellin A73, a Novel and Principal Antheridiogen in Lygodium japonicum

Plant and Cell Physiology ◽

10.1093/oxfordjournals.pcp.a077730 ◽

1989 ◽

Vol 30 (2) ◽

pp. 201-205 ◽

Cited By ~ 20

Author(s):

Kiyotoshi Takeno ◽

Hisakazu Yamane ◽

Tadayuki Yamauchi ◽

Nobutaka Takahashi ◽

Mark Furber ◽

...

Keyword(s):

Methyl Ester ◽

Biological Activities ◽

Lygodium Japonicum

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Identification of gibberellin A9 methyl ester as a natural substance regulating formation of reproductive organs in Lygodium japonicum

Planta ◽

10.1007/bf00388747 ◽

1979 ◽

Vol 147 (3) ◽

pp. 251-256 ◽

Cited By ~ 51

Author(s):

Hisakazu Yamane ◽

Nobutaka Takahashi ◽

Kiyotoshi Takeno ◽

Masaki Furuya

Keyword(s):

Methyl Ester ◽

Reproductive Organs ◽

Natural Substance ◽

Lygodium Japonicum

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Synthesis of GA73 methyl ester, a potent gibberellin-derived antheridiogen from gametophytes of the fern lygodium japonicum

Tetrahedron Letters ◽

10.1016/s0040-4039(00)97033-3 ◽

1990 ◽

Vol 31 (43) ◽

pp. 6235-6238 ◽

Cited By ~ 6

Author(s):

Petra Kraft-Klaunzer ◽

Mark Furber ◽

Lewis N. Mander ◽

Bruce Twitchin

Keyword(s):

Methyl Ester ◽

Lygodium Japonicum

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A last resort method for methyl ester hydrolysis using trimethyltin hydroxide under microwave conditions.

ChemSpider Synthetic Pages ◽

10.1039/sp263 ◽

2007 ◽

Author(s):

Andrew McCarroll

Keyword(s):

Methyl Ester ◽

Ester Hydrolysis

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Administration of Nω-?-Arginine Methyl Ester (L-NAME) impairs endothelium-dependent relaxation in gravid but not nongravid rats

Journal of the Society for Gynecologic Investigation ◽

10.1016/s1071-5576(02)00220-4 ◽

2003 ◽

Vol 10 (2) ◽

pp. 74-81 ◽

Cited By ~ 9

Author(s):

J Martínez-Orgado

Keyword(s):

Methyl Ester ◽

Endothelium Dependent Relaxation

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The Effect of Some Synthetic Arginyl and Lysyl Compounds on Clotting and Fibrinolysis

Thrombosis and Haemostasis ◽

10.1055/s-0038-1649094 ◽

1972 ◽

Vol 28 (02) ◽

pp. 289-298 ◽

Cited By ~ 1

Author(s):

M. J Weinstein ◽

R. F Doolittle

Keyword(s):

Methyl Ester ◽

Thrombin Activation

SummaryThe effects of a number of synthetic arginyl- and lysyl-compounds on clotting and fibrinolysis have been studied. The lysyl derivatives had no significant effect on the clotting of recalcified plasma or recalcified euglobulin preparations, but tosyllysine (TL) and tosyllysine methyl ester (TLME) were very effective inhibitors of fibrinolysis. Certain arginyl-peptides (in particular, tosylarginylsarcosine methyl ester) were very effective at delaying clotting in these systems. These same substances gave rise to an exaggerated thrombin production, however, evidently by interfering with the natural thrombin activation of plasma antithrombin(s).

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Activity of Plasmin and Streptokinase-Activator on Substituted Arginine and Lysine Esters

Thrombosis and Haemostasis ◽

10.1055/s-0038-1655623 ◽

1966 ◽

Vol 16 (01/02) ◽

pp. 018-031 ◽

Cited By ~ 13

Author(s):

S Sherry ◽

Norma Alkjaersig ◽

A. P Fletcher

Keyword(s):

Molecular Structure ◽

Methyl Ester ◽

Comparative Studies ◽

Esterase Activity ◽

Methyl Esters ◽

Hydrolytic Activity ◽

The Other ◽

Other Hand

SummaryComparative studies have been made of the esterase activity of plasmin and the streptokinase-activator of plasminogen on a variety of substituted arginine and lysine esters. Human plasmin preparations derived by different methods of activation (spontaneous in glycerol, trypsin, streptokinase (SK) and urokinase) are similar in their esterase activity; this suggests that the molecular structure required for such esterase activity is similar for all of these human plasmins. Bovine plasmin, on the other hand, differs from human plasmin in its activity on several of the substrates studied (e.g., the methyl esters of benzoyl arginine and tosyl, acetyl and carbobenzoxy lysine), a finding which supports the view that molecular differences exist between the two animal plasmins. The streptokinase-activator hydrolyzes both arginine and lysine esters but the ratios of hydrolytic activity are distinct from those of plasmin and of other activators of plasminogen. The use of benzoyl arginine methyl ester as a substrate for the measurement of the esterase activity of the streptokinase-activator is described.

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