New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana

Six new 14-membered ring cyclopeptide alkaloids, cambodines A–F (1–6), and two known compounds, frangufoline (7) and lotusanine B (8), were isolated from the root bark extract of Ziziphus cambodiana Pierre. Their structures and configurations were established based on 1D and 2D NMR, HRMS, ECD, and X...

Descripción completa

Detalles Bibliográficos
Autores principales: Lomchoey, Natthakaln, Panseeta, Panomwan, Boonsri, Pornthip, Apiratikul, Nuttapon, Prabpai, Samran, Kongsaeree, Palangpon, Suksamrarn, Sunit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9080573/
https://www.ncbi.nlm.nih.gov/pubmed/35541146
http://dx.doi.org/10.1039/c7ra13050c
_version_ 1784702817692286976
author Lomchoey, Natthakaln
Panseeta, Panomwan
Boonsri, Pornthip
Apiratikul, Nuttapon
Prabpai, Samran
Kongsaeree, Palangpon
Suksamrarn, Sunit
author_facet Lomchoey, Natthakaln
Panseeta, Panomwan
Boonsri, Pornthip
Apiratikul, Nuttapon
Prabpai, Samran
Kongsaeree, Palangpon
Suksamrarn, Sunit
author_sort Lomchoey, Natthakaln
collection PubMed
description Six new 14-membered ring cyclopeptide alkaloids, cambodines A–F (1–6), and two known compounds, frangufoline (7) and lotusanine B (8), were isolated from the root bark extract of Ziziphus cambodiana Pierre. Their structures and configurations were established based on 1D and 2D NMR, HRMS, ECD, and X-ray crystallographic data. Compounds 1 and 3 are rare 5(14)-type cyclopeptide alkaloids that possess an imidazolidin-4-one ring in the terminal unit. The cyclopeptides were tested for their in vitro antiplasmodial, antitubercular, and cytotoxic effects against three cancer cell lines. Compound 3 showed significant antiplasmodial activity against the malarial parasite Plasmodium falciparum, with an IC(50) value of 6.09 μM.
format Online
Article
Text
id pubmed-9080573
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90805732022-05-09 New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana Lomchoey, Natthakaln Panseeta, Panomwan Boonsri, Pornthip Apiratikul, Nuttapon Prabpai, Samran Kongsaeree, Palangpon Suksamrarn, Sunit RSC Adv Chemistry Six new 14-membered ring cyclopeptide alkaloids, cambodines A–F (1–6), and two known compounds, frangufoline (7) and lotusanine B (8), were isolated from the root bark extract of Ziziphus cambodiana Pierre. Their structures and configurations were established based on 1D and 2D NMR, HRMS, ECD, and X-ray crystallographic data. Compounds 1 and 3 are rare 5(14)-type cyclopeptide alkaloids that possess an imidazolidin-4-one ring in the terminal unit. The cyclopeptides were tested for their in vitro antiplasmodial, antitubercular, and cytotoxic effects against three cancer cell lines. Compound 3 showed significant antiplasmodial activity against the malarial parasite Plasmodium falciparum, with an IC(50) value of 6.09 μM. The Royal Society of Chemistry 2018-05-17 /pmc/articles/PMC9080573/ /pubmed/35541146 http://dx.doi.org/10.1039/c7ra13050c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Lomchoey, Natthakaln
Panseeta, Panomwan
Boonsri, Pornthip
Apiratikul, Nuttapon
Prabpai, Samran
Kongsaeree, Palangpon
Suksamrarn, Sunit
New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana
title New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana
title_full New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana
title_fullStr New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana
title_full_unstemmed New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana
title_short New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana
title_sort new bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of ziziphus cambodiana
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9080573/
https://www.ncbi.nlm.nih.gov/pubmed/35541146
http://dx.doi.org/10.1039/c7ra13050c
work_keys_str_mv AT lomchoeynatthakaln newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana
AT panseetapanomwan newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana
AT boonsripornthip newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana
AT apiratikulnuttapon newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana
AT prabpaisamran newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana
AT kongsaereepalangpon newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana
AT suksamrarnsunit newbioactivecyclopeptidealkaloidswithrareterminalunitfromtherootbarkofziziphuscambodiana

Ejemplares similares