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Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity

[Image: see text] Pinus eldarica is a medicinal tree used in traditional herbal medicine for the treatment of bronchial asthma and various skin diseases. As part of our ongoing search for bioactive phytochemicals with novel structures in natural products, we performed a phytochemical analysis of the...

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Autores principales: Jeong, Se Yun, Na, Myung Woo, Park, Eon Chung, Kim, Jin-Chul, Kang, Dong-Min, Hamishehkar, Hamed, Ahn, Mi-Jeong, Kim, Jung Kyu, Kim, Ki Hyun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9404486/
https://www.ncbi.nlm.nih.gov/pubmed/36033661
http://dx.doi.org/10.1021/acsomega.2c04147
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author Jeong, Se Yun
Na, Myung Woo
Park, Eon Chung
Kim, Jin-Chul
Kang, Dong-Min
Hamishehkar, Hamed
Ahn, Mi-Jeong
Kim, Jung Kyu
Kim, Ki Hyun
author_facet Jeong, Se Yun
Na, Myung Woo
Park, Eon Chung
Kim, Jin-Chul
Kang, Dong-Min
Hamishehkar, Hamed
Ahn, Mi-Jeong
Kim, Jung Kyu
Kim, Ki Hyun
author_sort Jeong, Se Yun
collection PubMed
description [Image: see text] Pinus eldarica is a medicinal tree used in traditional herbal medicine for the treatment of bronchial asthma and various skin diseases. As part of our ongoing search for bioactive phytochemicals with novel structures in natural products, we performed a phytochemical analysis of the methanol (MeOH) extract from P. eldarica needles collected in Iran. Phytochemical investigation of the MeOH extract, aided by liquid chromatography–mass spectrometry-based analysis, resulted in the isolation and identification of three labdane-type diterpenes (1–3), including a new and relatively unique norlabdane-type diterpene with a peroxide moiety, eldaricoxide A (1). The chemical structures of the isolated labdane-type diterpenes were elucidated by analyzing the spectroscopic data from 1D and 2D NMR and high-resolution electrospray ionization-mass spectrometry. The absolute configuration of eldaricoxide A (1) was established by employing a computational method, including electronic circular dichroism calculation and specific optical rotation. An anti-Helicobacter pylori test was conducted, where compound 3 exhibited the most potent antibacterial activity against H. pylori strain 51, inducing 72.7% inhibition (MIC(50) value of 92 μM), whereas eldaricoxide A (1) exhibited moderate antibacterial activity against H. pylori strain 51, inducing 54.5% inhibition (MIC(50) value of 95 μM). These findings demonstrated that the identified bioactive labdane-type diterpenes 1 and 3 can be applied in the development of novel antibiotics against H. pylori for the treatment of gastric and duodenal ulcers.
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spelling pubmed-94044862022-08-26 Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity Jeong, Se Yun Na, Myung Woo Park, Eon Chung Kim, Jin-Chul Kang, Dong-Min Hamishehkar, Hamed Ahn, Mi-Jeong Kim, Jung Kyu Kim, Ki Hyun ACS Omega [Image: see text] Pinus eldarica is a medicinal tree used in traditional herbal medicine for the treatment of bronchial asthma and various skin diseases. As part of our ongoing search for bioactive phytochemicals with novel structures in natural products, we performed a phytochemical analysis of the methanol (MeOH) extract from P. eldarica needles collected in Iran. Phytochemical investigation of the MeOH extract, aided by liquid chromatography–mass spectrometry-based analysis, resulted in the isolation and identification of three labdane-type diterpenes (1–3), including a new and relatively unique norlabdane-type diterpene with a peroxide moiety, eldaricoxide A (1). The chemical structures of the isolated labdane-type diterpenes were elucidated by analyzing the spectroscopic data from 1D and 2D NMR and high-resolution electrospray ionization-mass spectrometry. The absolute configuration of eldaricoxide A (1) was established by employing a computational method, including electronic circular dichroism calculation and specific optical rotation. An anti-Helicobacter pylori test was conducted, where compound 3 exhibited the most potent antibacterial activity against H. pylori strain 51, inducing 72.7% inhibition (MIC(50) value of 92 μM), whereas eldaricoxide A (1) exhibited moderate antibacterial activity against H. pylori strain 51, inducing 54.5% inhibition (MIC(50) value of 95 μM). These findings demonstrated that the identified bioactive labdane-type diterpenes 1 and 3 can be applied in the development of novel antibiotics against H. pylori for the treatment of gastric and duodenal ulcers. American Chemical Society 2022-08-15 /pmc/articles/PMC9404486/ /pubmed/36033661 http://dx.doi.org/10.1021/acsomega.2c04147 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Jeong, Se Yun
Na, Myung Woo
Park, Eon Chung
Kim, Jin-Chul
Kang, Dong-Min
Hamishehkar, Hamed
Ahn, Mi-Jeong
Kim, Jung Kyu
Kim, Ki Hyun
Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity
title Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity
title_full Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity
title_fullStr Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity
title_full_unstemmed Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity
title_short Labdane-type Diterpenes from Pinus eldarica Needles and Their Anti-Helicobacter pylori Activity
title_sort labdane-type diterpenes from pinus eldarica needles and their anti-helicobacter pylori activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9404486/
https://www.ncbi.nlm.nih.gov/pubmed/36033661
http://dx.doi.org/10.1021/acsomega.2c04147
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