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16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells

Molecules (Basel, Switzerland), 2019-06, Vol.24 (13), p.2366 [Peer Reviewed Journal]

2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. ;2019 by the authors. 2019 ;ISSN: 1420-3049 ;EISSN: 1420-3049 ;DOI: 10.3390/molecules24132366 ;PMID: 31248041

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Title:
16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells
Author: Hurtado-Díaz, Israel ; Sánchez-Carranza, Jessica Nayelli ; Romero-Estrada, Antonio ; González-Maya, Leticia ; González-Christen, Judith ; Herrera-Ruiz, Maribel ; Alvarez, Laura
Subjects: 16-hydroxy-lycopersene ; Absolute configuration ; Acridine orange ; Alcohol ; Alcohols ; Animals ; Annexin V ; anti-inflammatory activity ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Antioxidants - chemistry ; Antioxidants - isolation & purification ; Antioxidants - pharmacology ; Antiproliferatives ; Apoptosis ; Apoptosis - drug effects ; Bcl-2 protein ; Boraginaceae - chemistry ; Cancer ; Caspase-3 ; Cell cycle ; Cell death ; Cytotoxicity ; Diabetes ; Edema ; Ethidium bromide ; G1 phase ; Humans ; In vitro methods and tests ; Inflammation ; Lipopolysaccharides ; Macrophages - drug effects ; Macrophages - immunology ; Macrophages - metabolism ; Magnetic Resonance Spectroscopy ; Mice ; Mitochondria ; Molecular Structure ; Mortality ; Nitric oxide ; Nitric Oxide - biosynthesis ; NMR ; Nuclear magnetic resonance ; Plant Extracts - chemistry ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; polyisoprenoid alcohols ; RAW 264.7 Cells ; Staining ; Terpenes - chemistry ; Terpenes - isolation & purification ; Terpenes - pharmacology ; Tournefortia hirsutissima
Is Part Of: Molecules (Basel, Switzerland), 2019-06, Vol.24 (13), p.2366
Description: Three polyisoprenoid alcohols were isolated from the leaves of Tournefortia hirsutissima by a bioassay-guided phytochemical investigation. The compounds were identified as 16-hydroxy-lycopersene (Compound 1), (Z ,E ,ω)-dodecaprenol (Compound 2) and (Z ,E ,ω)-tridecaprenol (Compound 3). Compound 1, an unusual polyisoprenoid, was characterized by 1D and 2D NMR. We also determined the absolute configuration at C-16 by the modified Mosher's method. The in vitro antiproliferative and anti-inflammatory activities of the isolated compounds were evaluated. Among isolates, Compound 1 moderately inhibited the nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. On the other hand, Compound 1 displayed selective antiproliferative activity against HeLa, PC3, HepG2 and Hep3B cancer cells and was less potent against IHH non-cancerous cells. Compound 1 in Hep3B cells showed significant inhibition of cell cycle progression increasing the sub-G phase, suggesting cell death. Acridine orange/ethidium bromide staining and Annexin V-FITC/PI staining demonstrated that cell death induced by Compound 1 in cells Hep3B was by apoptosis. Further study showed that apoptosis induced by Compound 1 in Hep3b cells is associated with the increase of the ratio of Bax/Bcl-2, and caspase 3/7 activation. These results suggest that Compound 1 induce apoptotic cell death by the mitochondrial pathway. To our knowledge, this is the first report about the presence of polyprenol Compounds 1-3 in T. hirsutissima, and the apoptotic and anti-inflammatory action of Compound 1.
Publisher: Switzerland: MDPI AG
Language: English
Identifier: ISSN: 1420-3049
EISSN: 1420-3049
DOI: 10.3390/molecules24132366
PMID: 31248041
Source: Open Access: DOAJ Directory of Open Access Journals
AUTh Library subscriptions: ProQuest Central
GFMER Free Medical Journals
MEDLINE
PubMed Central
Alma/SFX Local Collection

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16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells

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