Nitensidine A, a guanidine alkaloid from Pterogyne nitens, induces osteoclastic cell death

Autoren

Yasuhiro Tajima
Hayato Murase
Kazuhiro Satake
Yuji Mitani
Luis Octavio Regasini
Vanderlan da Silva Bolzani
Thomas Efferth
Hiroshi Nakagawa

DOI

10.1007/s10616-013-9590-2

eISSN

1573-0778

ISSN

0920-9069

Ausgabe der Veröffentlichung

4

Zeitschrift

Cytotechnology

Sprache

en

Online publication date

2013

Paginierung

585 - 592

Datum der Veröffentlichung

2015

Status

Published

Herausgeber

Springer Science and Business Media LLC

Herausgeber URL

http://dx.doi.org/10.1007/s10616-013-9590-2

Datum der Datenerfassung

2022

Titel

Nitensidine A, a guanidine alkaloid from Pterogyne nitens, induces osteoclastic cell death

Ausgabe der Zeitschrift

67

Data source: Crossref

Abstract

Nitensidine A is a guanidine alkaloid isolated from Pterogyne nitens, a common plant in South America. To gain insight into the biological activity of P. nitens-produced compounds, we examined herein their biological effects on osteoclasts, multinucleated giant cells that regulate bone metabolism by resorbing bone. Among four guanidine alkaloids (i.e., galegine, nitensidine A, pterogynidine, and pterogynine), nitensidine A and pterogynine exhibited anti-osteoclastic effects at 10 μM by reducing the number of osteoclasts on the culture plate whereas galegine and pterogynidine did not. The anti-osteoclastic activities of nitensidine A and pterogynine were exerted in a concentration-dependent manner, whereas nitensidine A exhibited an approximate threefold stronger effect than pterogynine (IC50 values: nitensidine A, 0.93 ± 0.024 μM; pterogynine, 2.7 ± 0.40 μM). In the present study, the anti-osteoclastic effects of two synthetic nitensidine A derivatives (nitensidine AT and AU) were also examined to gain insight into the structural features of nitensidine A that exert an anti-osteoclastic effect. The anti-osteoclastic effect of nitensidine A was greatly reduced by substituting the imino nitrogen atom in nitensidine A with sulfur or oxygen. According to the differences in chemical structures and anti-osteoclastic effects of the four guanidine alkaloids and the two synthetic nitensidine A derivatives, it is suggested that the number, binding site, and polymerization degree of isoprenyl moiety in the guanidine alkaloids and the imino nitrogen atom cooperatively contribute to their anti-osteoclastic effects.

Addresses

Department of Applied Biological Chemistry, College of Bioscience and Biotechnology, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi, 487-8501, Japan.

Autoren

Yasuhiro Tajima
Hayato Murase
Kazuhiro Satake
Yuji Mitani
Luis Octavio Regasini
Vanderlan da Silva Bolzani
Thomas Efferth
Thomas Efferth
Hiroshi Nakagawa

DOI

10.1007/s10616-013-9590-2

eISSN

1573-0778

Externe Identifier

PubMed Identifier: 23892478
PubMed Central ID: PMC4474991

Open access

false

ISSN

0920-9069

Ausgabe der Veröffentlichung

4

Zeitschrift

Cytotechnology

Sprache

eng

Medium

Print-Electronic

Online publication date

2013

Paginierung

585 - 592

Datum der Veröffentlichung

2015

Status

Published

Datum der Datenerfassung

2013

Titel

Nitensidine A, a guanidine alkaloid from Pterogyne nitens, induces osteoclastic cell death.

Sub types

research-article
Journal Article

Ausgabe der Zeitschrift

67

Files

https://europepmc.org/articles/PMC4474991?pdf=render

Data source: Europe PubMed Central

Abstract

Nitensidine A is a guanidine alkaloid isolated from Pterogyne nitens, a common plant in South America. To gain insight into the biological activity of P. nitens-produced compounds, we examined herein their biological effects on osteoclasts, multinucleated giant cells that regulate bone metabolism by resorbing bone. Among four guanidine alkaloids (i.e., galegine, nitensidine A, pterogynidine, and pterogynine), nitensidine A and pterogynine exhibited anti-osteoclastic effects at 10 μM by reducing the number of osteoclasts on the culture plate whereas galegine and pterogynidine did not. The anti-osteoclastic activities of nitensidine A and pterogynine were exerted in a concentration-dependent manner, whereas nitensidine A exhibited an approximate threefold stronger effect than pterogynine (IC50 values: nitensidine A, 0.93 ± 0.024 μM; pterogynine, 2.7 ± 0.40 μM). In the present study, the anti-osteoclastic effects of two synthetic nitensidine A derivatives (nitensidine AT and AU) were also examined to gain insight into the structural features of nitensidine A that exert an anti-osteoclastic effect. The anti-osteoclastic effect of nitensidine A was greatly reduced by substituting the imino nitrogen atom in nitensidine A with sulfur or oxygen. According to the differences in chemical structures and anti-osteoclastic effects of the four guanidine alkaloids and the two synthetic nitensidine A derivatives, it is suggested that the number, binding site, and polymerization degree of isoprenyl moiety in the guanidine alkaloids and the imino nitrogen atom cooperatively contribute to their anti-osteoclastic effects.

Date of acceptance

2013

Autoren

Yasuhiro Tajima
Hayato Murase
Kazuhiro Satake
Yuji Mitani
Luis Octavio Regasini
Vanderlan da Silva Bolzani
Thomas Efferth
Hiroshi Nakagawa

Autoren-URL

https://www.ncbi.nlm.nih.gov/pubmed/23892478

DOI

10.1007/s10616-013-9590-2

Externe Identifier

PubMed Central ID: PMC4474991

ISSN

0920-9069

Ausgabe der Veröffentlichung

4

Zeitschrift

Cytotechnology

Sprache

eng

Country

United States

Paginierung

585 - 592

Datum der Veröffentlichung

2015

Status

Published

Datum, an dem der Datensatz öffentlich gemacht wurde

2015

Titel

Nitensidine A, a guanidine alkaloid from Pterogyne nitens, induces osteoclastic cell death.

Sub types

Journal Article

Ausgabe der Zeitschrift

67

Data source: PubMed

Nitensidine A, a guanidine alkaloid from Pterogyne nitens, induces osteoclastic cell death

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