Galloyl, caffeoyl and hexahydroxydiphenoyl esters of dihydrochalcone glucosides from Balanophora tobiracola

Seven galloyl, caffeoyl and ( S)-hexahydroxydiphenoyl esters of dihydrochalcone glucosides were isolated from Balanophora tobiracola. The 3-galloyl-4,6-HHDP esters strongly inhibited α-glucosidase. Seven galloyl, caffeoyl and (S)-hexahydroxydiphenoyl (HHDP) esters of dihydrochalcone glucosides were...

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Published in:	Phytochemistry (Oxford) Vol. 66; no. 6; pp. 675 - 681
Main Authors:	Tanaka, Takashi, Uehara, Rami, Nishida, Kaori, Kouno, Isao
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier Ltd 01-03-2005 Elsevier
Subjects:	alpha-glucosidase Balanophora Balanophora tobiracola Balanophoraceae Balanophoraceae - chemistry Biological and medical sciences caffeic acid Chalcone - analogs & derivatives Chalcone - chemistry Chalcone - isolation & purification Chalcones Chemical constitution chemical structure Dihydrochalcone enzyme inhibition esters Fundamental and applied biological sciences. Psychology gallic acid glucosides Glucosides - chemistry Glucosides - isolation & purification hexahydroxydiphenoyl esters Molecular Structure parasitic plants Phloretin Plant Components, Aerial - chemistry Plant physiology and development spectral analysis Tannin Japan Balanophora tobiracola Tannin Dihydrochalcone Balanophoraceae Phloretin Molecular structure Glucoside Glucose Chalcone Dicotyledones Angiospermae Isolation Spermatophyta
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Summary:	Seven galloyl, caffeoyl and ( S)-hexahydroxydiphenoyl esters of dihydrochalcone glucosides were isolated from Balanophora tobiracola. The 3-galloyl-4,6-HHDP esters strongly inhibited α-glucosidase. Seven galloyl, caffeoyl and (S)-hexahydroxydiphenoyl (HHDP) esters of dihydrochalcone glucosides were isolated from Balanophora tobiracola; based on spectroscopic and chemical evidence, their structures were determined to be 6″- O-galloyl-, 3″,4″-di- O-galloyl-, 4″,6″-di- O-galloyl-, 4″,6″- O-( S)-HHDP-, 3″- O-galloyl-4″,6″- O-( S)-HHDP-, 3″- O-caffeoyl-4″,6″- O-( S)-HHDP-3-hydroxyphloretin 4′- O-β- d-glucosides and 3″- O-galloyl-4″,6″- O-( S)-HHDP-phloretin 4′- O-β- d-glucoside, respectively. By contrast, these compounds were not found in the taxonomically related B. japonica. The 3″-galloyl-4″,6″-HHDP esters of the dihydrochalcone glucosides showed strong inhibitory activities against α-glucosidase. Four known compounds were also isolated namely, (±)-eriodictyol 7- O-β- d-glucoside, 1- O-caffeoyl-3- O-galloyl-β- d-glucose, phloretin 4′- O-β- d-glucoside, and 3-hydroxyphloretin 4′- O-β- d-glucoside.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0031-9422 1873-3700
DOI:	10.1016/j.phytochem.2004.10.018