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Article ; Online: Correction: Inhibition of Aβ aggregation by naphtho-γ-pyrone derivatives from a marine-derived fungus, Aspergillus sp. MPUC239.

Fujihara, Koji / Hashimoto, Takumi / Sasaki, Hiroaki / Koyama, Kiyotaka / Kinoshita, Kaoru

2023 Volume 77, Issue 3, Page(s) 624

Language	English
Publishing date	2023-05-11
Publishing country	Japan
Document type	Published Erratum
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-023-01708-8
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Article ; Online: Inhibition of Aβ aggregation by naphtho-γ-pyrone derivatives from a marine-derived fungus, Aspergillus sp. MPUC239.

Fujihara, Koji / Hashimoto, Takumi / Sasaki, Hiroaki / Koyama, Kiyotaka / Kinoshita, Kaoru

Journal of natural medicines

2023 Volume 77, Issue 3, Page(s) 516–522

Abstract: Alzheimer's disease (AD) is an important human disease that mainly causes cognitive impairments. Growing evidence has shown that amyloid-β (Aβ) peptide plays a key role in AD pathogenesis in what is known as the Aβ cascade hypothesis. This hypothesis ... ...

Abstract	Alzheimer's disease (AD) is an important human disease that mainly causes cognitive impairments. Growing evidence has shown that amyloid-β (Aβ) peptide plays a key role in AD pathogenesis in what is known as the Aβ cascade hypothesis. This hypothesis suggests the importance of suppressing Aβ aggregation and Aβ production. The latter process is governed by β-site APP Cleaving Enzyme1 (BACE1) and γ-secretase. We, therefore, focused on Aβ aggregation inhibitory activity, initially assessing numerous extracts derived from our marine-derived fungus collections. One EtOAc extract derived from an Aspergillus sp. exhibited Aβ aggregation inhibitory activity. Eleven known compounds (1-11) were isolated from CHCl
MeSH term(s)	Humans ; Amyloid Precursor Protein Secretases ; Pyrones/pharmacology ; Aspartic Acid Endopeptidases ; Neuroblastoma ; Amyloid beta-Peptides ; Alzheimer Disease/drug therapy ; Aspergillus ; Fungi
Chemical Substances	Amyloid Precursor Protein Secretases (EC 3.4.-) ; Pyrones ; Aspartic Acid Endopeptidases (EC 3.4.23.-) ; Amyloid beta-Peptides
Language	English
Publishing date	2023-04-10
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-023-01696-9
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Article ; Online: Citrobacter koseri inhibits the growth of Staphylococcus epidermidis by suppressing iron utilization.

Ohkubo, Tomotaka / Matsumoto, Yasuhiko / Sasaki, Hiroaki / Kinoshita, Kaoru / Ogasawara, Yuki / Sugita, Takashi

Biochemical and biophysical research communications

2023 Volume 691, Page(s) 149277

Abstract: The human skin microbiome consists of many species of bacteria, including Staphylococcus aureus and S. epidermidis. Individuals with atopic dermatitis (AD) have an increased relative abundance of S. aureus, which exacerbates the inflammation of AD. ... ...

Abstract	The human skin microbiome consists of many species of bacteria, including Staphylococcus aureus and S. epidermidis. Individuals with atopic dermatitis (AD) have an increased relative abundance of S. aureus, which exacerbates the inflammation of AD. Although S. epidermidis, a main component of healthy skin microbiota, inhibits the growth of S. aureus, the balance between S. epidermidis and S. aureus is disrupted in the skin of individuals with AD. In this study, we found that Citrobacter koseri isolated from patients with AD produces substances that inhibit the growth of S. epidermidis. Heat-treated culture supernatant (CS) of C. koseri inhibited the growth of S. epidermidis but not S. aureus. The genome of C. koseri has gene clusters related to siderophores and the heat-treated CS of C. koseri contained a high concentration of siderophores compared with the control medium. The inhibitory activity of C. koseri CS against the growth of S. epidermidis was decreased by the addition of iron, but not copper or zinc. Deferoxamine, an iron-chelating agent, also inhibited the growth of S. epidermidis, but not that of S. aureus. These findings suggest that C. koseri inhibits the growth of S. epidermidis by interfering with its iron utilization.
MeSH term(s)	Humans ; Staphylococcus epidermidis ; Citrobacter koseri ; Staphylococcus aureus ; Iron ; Dermatitis, Atopic ; Siderophores/pharmacology
Chemical Substances	Iron (E1UOL152H7) ; Siderophores
Language	English
Publishing date	2023-11-19
Publishing country	United States
Document type	Journal Article
ZDB-ID	205723-2
ISSN	1090-2104 ; 0006-291X ; 0006-291X
ISSN (online)	1090-2104 ; 0006-291X
ISSN	0006-291X
DOI	10.1016/j.bbrc.2023.149277
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Article ; Online: Enniatins from a marine-derived fungus Fusarium sp. inhibit biofilm formation by the pathogenic fungus Candida albicans.

Sasaki, Hiroaki / Kurakado, Sanae / Matsumoto, Yasuhiko / Yoshino, Yuta / Sugita, Takashi / Koyama, Kiyotaka / Kinoshita, Kaoru

Journal of natural medicines

2023 Volume 77, Issue 3, Page(s) 455–463

Abstract: Candidemia is a life-threatening disease common in immunocompromised patients, and is generally caused by the pathogenic fungus Candida albicans. C. albicans can change morphology from yeast to hyphae, forming biofilms on medical devices. Biofilm ... ...

Abstract	Candidemia is a life-threatening disease common in immunocompromised patients, and is generally caused by the pathogenic fungus Candida albicans. C. albicans can change morphology from yeast to hyphae, forming biofilms on medical devices. Biofilm formation contributes to the virulence and drug tolerance of C. albicans, and thus compounds that suppress this morphological change and biofilm formation are effective for treating and preventing candidemia. Marine organisms produce biologically active and structurally diverse secondary metabolites that are promising lead compounds for treating numerous diseases. In this study, we explored marine-derived fungus metabolites that can inhibit morphological change and biofilm formation by C. albicans. Enniatin B (1), B1 (2), A1 (3), D (4), and E (5), visoltricin (6), ergosterol peroxide (7), 9,11-dehydroergosterol peroxide (8), and 3β,5α,9α-trihydroxyergosta-7,22-dien-6-one (9) were isolated from the marine-derived fungus Fusarium sp. Compounds 1-5 and 8 exhibited inhibitory activity against hyphal formation by C. albicans, and compounds 1-3 and 8 inhibited biofilm formation by C. albicans. Furthermore, compounds 1-3 decreased cell surface hydrophobicity and expression of the hypha-specific gene HWP1 in C. albicans. Compound 1 was obtained in the highest yield. An in vivo evaluation system using silkworms pierced with polyurethane fibers (a medical device substrate) showed that compound 1 inhibited biofilm formation by C. albicans in vivo. These results indicate that enniatins could be lead compounds for therapeutic agents for biofilm infections by C. albicans.
MeSH term(s)	Humans ; Candida albicans/genetics ; Antifungal Agents/pharmacology ; Fusarium ; Candidemia ; Biofilms
Chemical Substances	enniatins ; Antifungal Agents
Language	English
Publishing date	2023-03-01
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-023-01684-z
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Article ; Online: Photoreaction products of extract from the fruiting bodies of Polyozellus multiplex.

Otsuka, Hayato / Nakai, Keiyo / Shimizu, Emi / Yamaguchi, Takamasa / Yamano, Mitsuhisa / Sasaki, Hiroaki / Koyama, Kiyotaka / Kinoshita, Kaoru

Journal of natural medicines

2024 Volume 78, Issue 3, Page(s) 547–557

Abstract: Photochemical reactions are powerful tools for synthesizing organic molecules. The input of energy provided by light offers a means to produce strained and unique molecules that cannot be assembled using thermal protocols, allowing for the production of ... ...

Abstract	Photochemical reactions are powerful tools for synthesizing organic molecules. The input of energy provided by light offers a means to produce strained and unique molecules that cannot be assembled using thermal protocols, allowing for the production of immense molecular complexity in a single chemical step. Furthermore, unlike thermal reactions, photochemical reactions do not require active reagents such as acids, bases, metals, or enzymes. Photochemical reactions play a central role in green chemistry. This article reports the isolation and structure determination of four new compounds (1-4) from the photoreaction products of the Polyozellus multiplex MeOH ext. The structures of the new compounds were elucidated using MS, IR, comprehensive NMR measurements and microED. The four compounds were formed by deacetylation of polyozellin, the main secondary metabolite of P. multiplex, and addition of singlet oxygen generated by sunlight. To develop drugs for treating Alzheimer's disease (AD) on the basis of the amyloid cascade hypothesis, the compounds (1-4) obtained by photoreaction were evaluated for BACE1 inhibitory activity. The hydrolysates (5 and 6) of polyozellin, the main secondary metabolites of P. multiplex, were also evaluated. The photoreaction products (3 and 4) and hydrolysates (5 and 6) of polyozellin showed BACE1 inhibitory activity (IC
MeSH term(s)	Fruiting Bodies, Fungal/chemistry ; Molecular Structure ; Amyloid Precursor Protein Secretases/metabolism ; Amyloid Precursor Protein Secretases/antagonists & inhibitors ; Aspartic Acid Endopeptidases/antagonists & inhibitors ; Aspartic Acid Endopeptidases/metabolism ; Photochemical Processes
Language	English
Publishing date	2024-03-21
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-024-01790-6
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Amyloid β aggregation inhibitory activity of triterpene saponins from the cactus Stenocereus pruinosus

Fujihara, Koji / Shimoyama, Takuya / Kawazu, Ryo / Sasaki, Hiroaki / Koyama, Kiyotaka / Takahashi, Kunio / Kinoshita, Kaoru

Natural medicines. 2021 Mar., v. 75, no. 2

2021

Abstract: Six new triterpene saponins (1–5,7) and 3 known saponins (6,8,9) were isolated from MeOH extracts of the cactus Stenocereus pruinosus. The structures of the isolated saponins were elucidated using MS, IR, and comprehensive NMR measurements. To develop ... ...

Abstract	Six new triterpene saponins (1–5,7) and 3 known saponins (6,8,9) were isolated from MeOH extracts of the cactus Stenocereus pruinosus. The structures of the isolated saponins were elucidated using MS, IR, and comprehensive NMR measurements. To develop drugs for treating Alzheimer’s disease (AD) on the basis of the amyloid cascade hypothesis, the isolated saponins were evaluated for inhibition of BACE1 activity and amyloid beta (Aβ) aggregation using thioflavin-T assay, and triterpenes as an aglycone moiety and an alkaline hydrolysate of the saponins were also evaluated. One saponin, stenoside A (7), exhibited inhibitory activity related to Aβ aggregation and its degree of Aβ aggregation was 40.6% at 100 μM.
Keywords	Stenocereus ; amyloid ; cacti and succulents ; hydrolysates ; moieties ; triterpenoid saponins
Language	English
Dates of publication	2021-03
Size	p. 284-298.
Publishing place	Springer Singapore
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	1201350-x
ISSN	1340-3443
ISSN	1340-3443
DOI	10.1007/s11418-020-01463-0
Database	NAL-Catalogue (AGRICOLA)

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Article: Triterpenoid saponins from Polaskia chichipe Backbg. and their inhibitory or promotional effects on the melanogenesis of B16 melanoma cells

Fujihara, Koji / Kinoshita, Kaoru / Koyama, Kiyotaka / Takahashi, Kunio

Natural medicines. 2017 Oct., v. 71, no. 4

2017

Abstract: Five new oleanane-type saponins 1–5 together with a known saponin 6 and a steroidal glycoside 7 were isolated from Polaskia chichipe Backbg., and their structures were determined from their 1D and 2D NMR and HRFABMS spectral data. The six isolated ... ...

Abstract	Five new oleanane-type saponins 1–5 together with a known saponin 6 and a steroidal glycoside 7 were isolated from Polaskia chichipe Backbg., and their structures were determined from their 1D and 2D NMR and HRFABMS spectral data. The six isolated saponins 1–6 were tested for their effects on the melanogenesis of B16 melanoma 4A5 cells. Compound 1 exerted an inhibitory effect at 100 μM whereas compound 3 promoted melanogenesis at the same concentration, even though these two compounds contain the same aglycon structure. The dose-dependent activities of compounds 1 and 3 on melanin synthesis were investigated.
Keywords	dose response ; melanin ; melanogenesis ; melanoma ; nuclear magnetic resonance spectroscopy ; Polaskia chichipe ; spectral analysis ; triterpenoid saponins
Language	English
Dates of publication	2017-10
Size	p. 606-616.
Publishing place	Springer Singapore
Document type	Article
ZDB-ID	1201350-x
ISSN	1340-3443
ISSN	1340-3443
DOI	10.1007/s11418-017-1082-9
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Amyloid β aggregation inhibitory activity of triterpene saponins from the cactus Stenocereus pruinosus.

Fujihara, Koji / Shimoyama, Takuya / Kawazu, Ryo / Sasaki, Hiroaki / Koyama, Kiyotaka / Takahashi, Kunio / Kinoshita, Kaoru

Journal of natural medicines

2020 Volume 75, Issue 2, Page(s) 284–298

Abstract: Six new triterpene saponins (1-5,7) and 3 known saponins (6,8,9) were isolated from MeOH extracts of the cactus Stenocereus pruinosus. The structures of the isolated saponins were elucidated using MS, IR, and comprehensive NMR measurements. To develop ... ...

Abstract	Six new triterpene saponins (1-5,7) and 3 known saponins (6,8,9) were isolated from MeOH extracts of the cactus Stenocereus pruinosus. The structures of the isolated saponins were elucidated using MS, IR, and comprehensive NMR measurements. To develop drugs for treating Alzheimer's disease (AD) on the basis of the amyloid cascade hypothesis, the isolated saponins were evaluated for inhibition of BACE1 activity and amyloid beta (Aβ) aggregation using thioflavin-T assay, and triterpenes as an aglycone moiety and an alkaline hydrolysate of the saponins were also evaluated. One saponin, stenoside A (7), exhibited inhibitory activity related to Aβ aggregation and its degree of Aβ aggregation was 40.6% at 100 μM.
MeSH term(s)	Alzheimer Disease/drug therapy ; Amyloid beta-Peptides/antagonists & inhibitors ; Cactaceae/chemistry ; Humans ; Saponins/chemistry ; Triterpenes/chemistry
Chemical Substances	Amyloid beta-Peptides ; Saponins ; Triterpenes
Language	English
Publishing date	2020-11-24
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-020-01463-0
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Triterpenoid saponins from Polaskia chichipe Backbg. and their inhibitory or promotional effects on the melanogenesis of B16 melanoma cells.

Fujihara, Koji / Takahashi, Kunio / Koyama, Kiyotaka / Kinoshita, Kaoru

Journal of natural medicines

2017

Abstract: Five new oleanane-type saponins 1-5 together with a known saponin 6 and a steroidal glycoside 7 were isolated from Polaskia chichipe Backbg., and their structures were determined from their 1D and 2D NMR and HRFABMS spectral data. The six isolated ... ...

Abstract	Five new oleanane-type saponins 1-5 together with a known saponin 6 and a steroidal glycoside 7 were isolated from Polaskia chichipe Backbg., and their structures were determined from their 1D and 2D NMR and HRFABMS spectral data. The six isolated saponins 1-6 were tested for their effects on the melanogenesis of B16 melanoma 4A5 cells. Compound 1 exerted an inhibitory effect at 100 μM whereas compound 3 promoted melanogenesis at the same concentration, even though these two compounds contain the same aglycon structure. The dose-dependent activities of compounds 1 and 3 on melanin synthesis were investigated.
Language	English
Publishing date	2017-05-11
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-017-1082-9
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Zs.A 2692: Show issues

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Article: Meroterpenoids with BACE1 Inhibitory Activity from the Fruiting Body of Boletinus asiaticus

Yatsu, Genki / Kino, Yoshihiro / Sasaki, Hiroaki / Satoh, Jun-ichi / Kinoshita, Kaoru / Koyama, Kiyotaka

Journal of natural products. 2019 June 25, v. 82, no. 7

2019

Abstract: BACE1 inhibitory activity-guided fractionation of an extract of the fruiting body of Boletinus asiaticus yielded five novel meroterpenoids (1–5) and one known compound (6; asiaticusin A). The structures of these compounds were determined by ... ...

Abstract	BACE1 inhibitory activity-guided fractionation of an extract of the fruiting body of Boletinus asiaticus yielded five novel meroterpenoids (1–5) and one known compound (6; asiaticusin A). The structures of these compounds were determined by interpretation of NMR, MS, and IR spectral data. The five new compounds contain 4-hydroxybenzoic acid and geranylgeranoic acid units. Compounds 4–6 possessed BACE1 inhibitory activity (IC50 values: 14.7, 11.4, and 2.0 μM, respectively).
Keywords	4-hydroxybenzoic acid ; fractionation ; fruiting bodies ; inhibitory concentration 50 ; meroterpenoids ; nuclear magnetic resonance spectroscopy ; spectral analysis
Language	English
Dates of publication	2019-0625
Size	p. 1797-1801.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.8b01092
Database	NAL-Catalogue (AGRICOLA)

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