Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 

Saved Queries

Sign in to use this feature.

Search Filter Reset All

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Subjects Reset
Select Subjects

Journals

remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Journals Reset
Select Journals

Article Types

remove_circle_outline
remove_circle_outline
Add Article Types Reset
Select Article Types

Countries / Regions

remove_circle_outline
remove_circle_outline
Add Countries / Regions Reset
Select Countries / Regions
Update Search
share announcement

Search Results (5)

Search Parameters:
Keywords = pericosine

Order results
Result details
Results per page
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
14 pages, 4022 KiB  
Article
Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities
by Yoshihide Usami, Yoshino Mizobuchi, Mai Ijuin, Takeshi Yamada, Mizuki Morita, Koji Mizuki, Hiroki Yoneyama and Shinya Harusawa
Mar. Drugs 2022, 20(7), 438; https://doi.org/10.3390/md20070438 - 30 Jun 2022
Cited by 2 | Viewed by 2367
Abstract
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 [...] Read more.
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 α-glucosidase to a greater extent than those of their corresponding (+)-enantiomers, whereas (+)-iodopericosine A showed increased activity when compared to its (−)-enantiomer. Full article
(This article belongs to the Special Issue Chemical Modification and Structural Elucidation of Marine Natural Products)
►▼ Show Figures

Graphical abstract

24 pages, 1724 KiB  
Review
The Chemistry and Pharmacology of Fungal Genus Periconia: A Review
by Azmi Azhari and Unang Supratman
Sci. Pharm. 2021, 89(3), 34; https://doi.org/10.3390/scipharm89030034 - 29 Jul 2021
Cited by 27 | Viewed by 7771
Abstract
Periconia is filamentous fungi belonging to the Periconiaceae family, and over the last 50 years, the genus has shown interest in natural product exploration for pharmacological purposes. Therefore, this study aims to analyze the different species of Periconia containing natural products such as [...] Read more.
Periconia is filamentous fungi belonging to the Periconiaceae family, and over the last 50 years, the genus has shown interest in natural product exploration for pharmacological purposes. Therefore, this study aims to analyze the different species of Periconia containing natural products such as terpenoids, polyketides, cytochalasan, macrosphelides, cyclopentenes, aromatic compounds, and carbohydrates carbasugar derivates. The isolated compound of this kind, which was reported in 1969, consisted of polyketide derivatives and their structures and was determined by chemical reaction and spectroscopic methods. After some years, 77 compounds isolated from endophytic fungus Periconia were associated with eight plant species, 28 compounds from sea hare Aplysia kurodai, and ten from endolichenic fungi Parmelia sp. The potent pharmacological agents from this genus are periconicin A, which acts as an antimicrobial, pericochlorosin B as an anti-human immunodeficiency virus (HIV), peribysin D, and pericosine A as cytotoxic agents, and periconianone A as an anti-inflammatory agent. Furthermore, information about taxol and piperine from Periconia producing species was also provided. Therefore, this study supports discovering new drugs produced by the Periconia species and compares them for future drug development. Full article
►▼ Show Figures

Figure 1

18 pages, 3352 KiB  
Article
Syntheses and Glycosidase Inhibitory Activities, and in Silico Docking Studies of Pericosine E Analogs Methoxy-Substituted at C6
by Yoshihide Usami, Megumi Higuchi, Koji Mizuki, Mizuki Yamamoto, Mao Kanki, Chika Nakasone, Yuya Sugimoto, Makio Shibano, Yoshihiro Uesawa, Junko Nagai, Hiroki Yoneyama and Shinya Harusawa
Mar. Drugs 2020, 18(4), 221; https://doi.org/10.3390/md18040221 - 20 Apr 2020
Cited by 5 | Viewed by 3015
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Marine Natural Products and Obesity 2020)
►▼ Show Figures

Graphical abstract

16 pages, 1088 KiB  
Article
Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (−)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors
by Yoshihide Usami, Koji Mizuki, Rikiya Kawahata, Makio Shibano, Atsuko Sekine, Hiroki Yoneyama and Shinya Harusawa
Mar. Drugs 2017, 15(1), 22; https://doi.org/10.3390/md15010022 - 23 Jan 2017
Cited by 9 | Viewed by 5876
Abstract
Pericosine E (6), a metabolite of Periconia byssoides OUPS-N133 was originally isolated from the sea hare Aplysia kurodai, which exists as an enantiomeric mixture in nature. The enantiospecific syntheses of both enantiomers of Periconia byssoides OUPS-N133 has been achieved, along [...] Read more.
Pericosine E (6), a metabolite of Periconia byssoides OUPS-N133 was originally isolated from the sea hare Aplysia kurodai, which exists as an enantiomeric mixture in nature. The enantiospecific syntheses of both enantiomers of Periconia byssoides OUPS-N133 has been achieved, along with six stereoisomers, using a common simple synthetic strategy. For these efficient syntheses, highly regio- and steroselective processes for the preparation of bromohydrin and anti-epoxide intermediates were applied. In order to access the unique O-linked carbadisaccharide structure, coupling of chlorohydrin as a donor and anti-epoxide as an acceptor was achieved using catalytic BF3·Et2O. Most of the synthesized compounds exhibited selectively significant inhibitory activity against α-glycosidase derived from yeast. The strongest analog showed almost 50 times the activity of the positive control, deoxynojirimycin. Full article
►▼ Show Figures

Graphical abstract

21 pages, 423 KiB  
Review
Synthetic Efforts for Stereo Structure Determination of Cytotoxic Marine Natural Product Pericosines as Metabolites of Periconia sp. from Sea Hare
by Yoshihide Usami, Hayato Ichikawa and Masao Arimoto
Int. J. Mol. Sci. 2008, 9(3), 401-421; https://doi.org/10.3390/ijms9030401 - 24 Mar 2008
Cited by 33 | Viewed by 12304
Abstract
Pericosines are unique C7 cyclohexenoid metabolites of Periconia byssoides OUPS-N133 fungus that was originally isolated from the sea hare, Aplysia kurodai. Pericosines show significant in vitro cytotoxicity against P388 lymphocytic leukemia cells. Pericosine A, in particular, shows the most potent activity and [...] Read more.
Pericosines are unique C7 cyclohexenoid metabolites of Periconia byssoides OUPS-N133 fungus that was originally isolated from the sea hare, Aplysia kurodai. Pericosines show significant in vitro cytotoxicity against P388 lymphocytic leukemia cells. Pericosine A, in particular, shows the most potent activity and significant in vivo antitumor activity against P388 cells. Thus, pericosines are promising candidates for seed compounds of anticancer drugs. However, before the total syntheses of pericosines were accomplished, their stereo structures could not be determined by spectral analyses because they have multifunctionalized cyclohexenoid structures with torsional strain. In this review, synthetic efforts for pericosines in this decade are surveyed. Full article
(This article belongs to the Special Issue Natural Compounds for Cancer Treatment and Prevention)
►▼ Show Figures

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying article 1-50 on page 1 of 1.
Back to TopTop