Synthesis of Marine-Derived Carbasugar Pericosines

Usami, Yoshihide

doi:10.1016/b978-0-444-63294-4.00010-3

Cited by 12 publications

(7 citation statements)

References 113 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…kurodai, possessing a unique structural feature of methyl cyclohexenecarboxylate core bearing hydroxy or methoxy substituents as well as chlorine atoms. [5][6][7][8] Structures of pericosines A-E (1-6) are presented in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…The isolation of pericosine A (1 Cl ) and B (2) as metabolites of the marine-derived fungus Periconis byssoides N133 was first reported in 1997, and pericosines C-E (3)(4)(5)(6) were discovered in 2008 [13][14][15]. The unique carbasugar structures constituting the highly functionalized cyclohexene ring are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities

et al. 2022

Self Cite

View full text Add to dashboard Cite

The enantiomers of 6-fluoro-, 6-bromo-, and 6-iodopericosine A were synthesized. An efficient synthesis of both enantiomers of pericoxide via 6-bromopericosine A was also developed. These 6-halo-substituted pericosine A derivatives were evaluated in terms of their antitumor activity against three types of tumor cells (p388, L1210, and HL-60) and glycosidase inhibitory activity. The bromo- and iodo-congeners exhibited moderate antitumor activity similar to pericosine A against the three types of tumor cell lines studied. The fluorinated compound was less active than the others, including pericosine A. In the antitumor assay, no significant difference in potency between the enantiomers was observed for any of the halogenated compounds. Meanwhile, the (−)-6-fluoro- and (−)-6-bromo-congeners inhibited -glucosidase to a greater extent than those of their corresponding (+)-enantiomers, whereas (+)-iodopericosine A showed increased activity when compared to its (−)-enantiomer.

show abstract

“…Pericosines A-C and E (1-4) are marine natural products produced by the fungus Periconia byssoides OUPS-N133 derived from sea hare Aplysia kurodai (Figure 1) [1]. The unique carbasugar structures of these species and the significant antitumor activity of pericosine A have drawn increased attention to pericosines A-C (1-3) as synthetic targets and thus inspired numerous synthetic studies [2][3][4][5][6][7][8][9]. Natural pericosine E (4) deserves particular attention, as it features an O-linked carbadisaccharide structure between pericosine A-like and pericosine B-like moieties with opposite absolute configurations and exists as a mixture of enantiomers [1].…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Glycosidase Inhibitory Activities, and in Silico Docking Studies of Pericosine E Analogs Methoxy-Substituted at C6

et al. 2020

Self Cite

View full text Add to dashboard Cite

Inspired by the significant α-glucosidase inhibitory activities of (+)- and (−)-pericosine E, we herein designed and synthesized 16 analogs of these marine natural products bearing a methoxy group instead of a chlorine atom at C6. Four of these compounds exhibited moderate α-glucosidase inhibitory activities, which were weaker than those of the corresponding chlorine-containing species. The four compounds could be prepared by coupling reactions utilizing the (−)-pericosine B moiety. An additional in silico docking simulation suggested that the reason of reduced activity of the C6-methoxylated analogs might be an absence of hydrogen bonding between a methoxy group with the surrounding amino acid residues in the active site in α-glucosidase.

show abstract

Synthesis of Marine-Derived Carbasugar Pericosines

Cited by 12 publications

References 113 publications

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

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

Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities

Syntheses and Glycosidase Inhibitory Activities, and in Silico Docking Studies of Pericosine E Analogs Methoxy-Substituted at C6

Contact Info

Product

Resources

About