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Thursday, 10 September 2015

Rare 6-deoxy-D-altrose from the folk medicinal mushroom Lactarius akahatsu

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 A rare sugar, 6-deoxy-D-altrose, isolated from a polysaccharide extracted from an edible folk medicinal mushroom (Lactarius akahatsu) was identified using 1H and 13C-NMR including 2D-COSY and 2D-HSQC spectroscopy, and specific rotation. The 6-deoxy-sugar isolated from the acid hydrolysate of the polysaccharide extracted from L. akahatsu was involved in four anomeric isomers (α- and β-pyranose, and α-and β-furanose) in aqueous solution due to mutarotation. Almost all of the signals from the 1D (1H- and 13C-) and 2D (COSY and HSQC)-NMR spectra of the 6-deoxy-sugar agreed with the data from the authentic 6-deoxy-D-altrose. The specific rotation [α]589 of the 6-deoxy-sugar isolated from L. akahatsu was +17.6°. Thus, the 6-deoxy-sugar isolated from Lactarius akahatsu was identified as 6-deoxy-D-altrose.

 ChemSpider 2D Image | 6-Deoxy-D-altrose | C6H12O5
D-Altrose, 6-deoxy- 
18546-02-6 [RN]
6-deoxyaltrose
6-Deoxy-L-altrose


 

Figure 1 : 1H- and 13C-NMR spectra of the polysaccharide isolated from L. akahatsu at 70°C.



Figure 2 : 1H and 13C-NMR spectra of 6-deoxy-sugar at 25°C.




Figure 3 : COSY spectrum of 6-deoxy-sugar isolated from L. akahatsu at 25°C.

Tako et al.Biochemical Compounds  2013 1:5DOI : 10.7243/2052-9341-1-5



Figure 4 : HSQC spectrum of 6-deoxy-sugar isolated from L. akahatsu 25°C

Tako et al.Biochemical Compounds  2013 1:5DOI : 10.7243/2052-9341-1-5



 http://www.hoajonline.com/journals/A-Z/B/biochemcomp/content/supplement/volume/1/5/s2.jpg
 http://www.hoajonline.com/journals/A-Z/B/biochemcomp/content/supplement/volume/1/5/s3.jpg

Rare 6-deoxy-D-altrose from the folk medicinal mushroom Lactarius akahatsu

Masakuni Tako1,2*, Jyunpei Shimabukuro1,3, Wen Jiang1, Masashi Yamada3, Hideharu Ishida3 and Makoto Kiso3
*Correspondence: Masakuni Tako tako@agr.u-ryukyu.ac.jp
1. University of the Ryukyus, Department of Subtropical Bioscience and Biotechnology, Nishihara, Okinawa 903-0213, Japan......http://www.hoajonline.com/biochemcomp/2052-9341/1/5

[ - ] Author Affiliations
2. University of the Ryukyus, Health and Longevity Research Laboratory, Integrated Innovation Research Centre, Nishihara, Okinawa 903-0213, Japan.
3. Gifu University, Department of Applied Bio-organic Chemistry, Gifu, Gifu 501-1193, Japan.

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