Enantiomeric composition of natural pericosine A derived from Periconia byssoides and α‐glycosidase inhibitory activity of (−)‐enantiomer

Chiral high‐performance liquid chromatography (HPLC) analysis of natural pericosine A, which appeared in literature first in 1977, from Periconia byssoides was conducted using a column CHIRALPAK® AD‐H to determine the enantiomeric composition of the original mixture which was found to be 68: 32 mixt...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2022-10, Vol.34 (10), p.1320-1327
Main Authors: Usami, Yoshihide, Nakamura, Kimika, Mizobuchi, Yoshino, Mizuki, Koji, Harusawa, Shinya, Yoneyama, Hiroki, Yamada, Takeshi
Format: Article
Language:English
Subjects:
Anticancer properties
Antitumor activity
chiral HPLC analysis
Composition
Cytotoxicity
enantiomeric mixture
Enantiomers
Galactosidase
Glucosidase
glycosidase inhibitory activity
Glycosidases
High performance liquid chromatography
Liquid chromatography
Mannosidase
Mixtures
Periconia
Periconia byssoides
pericosine A
Toxicity
Tumor cell lines
Tumor cells
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Summary:Chiral high‐performance liquid chromatography (HPLC) analysis of natural pericosine A, which appeared in literature first in 1977, from Periconia byssoides was conducted using a column CHIRALPAK® AD‐H to determine the enantiomeric composition of the original mixture which was found to be 68: 32 mixtures of (+)‐ and (−)‐enantiomer, respectively. Furthermore, two independently isolated samples of pericosine A from the same fungus were also analyzed to show the two peaks in the HPLC charts at approximate 1:1 ratio. These results concluded that pericosine A derived from Periconia byssoides was indeed an enantiomeric mixture. Synthesized enantiomers were subjected to evaluation of antitumor activity against three kinds of tumor cells (p388, L1210, HL‐60), indicating moderate cytotoxicity against all three kinds of tumor cell lines, but significant difference in potency between the enantiomers was not observed. In contrast, when both the enantiomers of pericosine A were evaluated against five kinds of glycosidases‐inhibitory activities (α‐ and β‐glucosidases, α‐ and β‐galactosidases, and α‐mannosidase), an apparent difference on anti‐glycosidase assay was found between the enantiomers: (−)‐pericosine A inhibited α‐glucosidase at IC50: 2.25 mM, and β‐galactosidase at IC50: 5.38 mM, albeit the (+)‐enantiomer showed inactivity against these five enzymes.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23491