A convenient synthesis of lepidimoide from okra mucilage and its growth-promoting activity in hypocotyls.
The total synthesis of the unsaturated disaccharide, lepidimoide 4-deoxy-beta-L-threo-hex-4-enopyranuronosyl-(1-->2)-L-rhamnopyranose sodium salt, has been carried out from D-glucose and L-rhamnose (Tetrahedron Lett. 1993, 34, 2653), but the process is very long and complicated. A method for more easily producing this compound and in large quantities is necessary for further research. We have succeeded in conveniently synthesizing lepidimoide from okra (Hibiscus esculentus L.) fruit mucilage. At the same time, the isomer (epi-lepidimoide) was obtained as a byproduct. The structure was determined as the 4-deoxy-beta-L-threo-hex-4-enopyranuronosyl-(1-->2)-6-deoxy-L-glucopyranose sodium salt by spectral analysis. We found that lepidimoide easily epimerized to epi-lepidimoide in alkaline media. Both lepidimoide and epi-lepidimoide exhibited the same high activity in the cockscomb hypocotyls elongation test.
Hirose
Katsutoshi
K
Institute of Applied Biochemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8572, Japan. k_hirose@kncweb.co.jp
Endo
Keiichiro
K
Hasegawa
Koji
K
D028483:Abelmoschus / Q000737:chemistry*; D000269:Adhesives / Q000737:chemistry*; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D005947:Glucose / Q000737:chemistry; D018546:Hypocotyl / Q000187:drug effects* / Q000254:growth & development; D007536:Isomerism; D015394:Molecular Structure; D009414:Nerve Growth Factors; D010936:Plant Extracts / Q000032:analysis / Q000737:chemistry; D012210:Rhamnose / Q000737:chemistry
D000269:Adhesives; D004187:Disaccharides; D009414:Nerve Growth Factors; D010936:Plant Extracts; C103036:lepidimoide; D005947:Glucose; D012210:Rhamnose