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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https://www.mdpi.com/1420-3049/24/13/2366

Israel Hurtado-Díaz ¹,Jessica Nayelli Sánchez-Carranza ²,Antonio Romero-Estrada ¹,Leticia González-Maya ²,Judith González-Christen ²,Maribel Herrera-Ruiz ³ andLaura Alvarez ^1,*

¹

Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca 62209, Morelos, Mexico

²

Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca 62209, Morelos, Mexico

³

Centro de Investigación Biomédica del Sur, Instituto Mexicano del Seguro Social, Xochitepec 62790, Morelos, Mexico

^*

Author to whom correspondence should be addressed.

Academic Editors: Ewa Swiezewska and Liliana Surmacz

Molecules 2019, 24(13), 2366; https://doi.org/10.3390/molecules24132366

Received: 13 June 2019 / Revised: 24 June 2019 / Accepted: 24 June 2019 / Published: 26 June 2019

(This article belongs to the Special Issue Plant Isoprenoids)

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Abstract

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), (Z₈,E₃,ω)-dodecaprenol (Compound 2) and (Z₉,E₃,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 1moderately 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-G₁ 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. View Full-Text

Keywords: 16-hydroxy-lycopersene; polyisoprenoid alcohols; Tournefortia hirsutissima; anti-inflammatory activity; apoptosis

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Hurtado-Díaz, I.; Sánchez-Carranza, J.N.; Romero-Estrada, A.; González-Maya, L.; González-Christen, J.; Herrera-Ruiz, M.; Alvarez, L. 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 2019, 24, 2366.

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The toxicological assessment of ethanolic whole-plant extract of Eleucine indica in Wistar albino rats

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Introduction: Eleucine indica is a medicinal plant used by the Ibibios of Nigeria in the treatment of malaria but its safety with chronic use has not been determined. This study was to evaluate the toxicological effects of the extract in adult albino Wistar rats. Methods: The rats of both sexes were randomized into 5 groups of 6 animals per group and orally administered with extract (200, 400 and 600 mg/kg) for groups 2-4, respectively. Group 1 received distilled water (10 mL/kg) orally and served as negative control while group 5 was administered with 100 mg/kg of silymarin orally. Drugs were administered on alternate days for 28 days at 09.00 am. Toxic manifestations and mortality were monitored daily and weight changes of animals were recorded every week. On day 29, after an overnight fast, the animals were weighed, anaesthetized with light chloroform. An autopsy was performed during which any macroscopic abnormalities were noted. The brain, heart, liver, spleen, kidney and lungs were weighed immediately after removal. Samples of these organs were fixed in 10% formalin and kept in that solution for further histopathological examination. Data were analysed using one-way analysis of variance (ANOVA) followed by Tukey Kramer multiple comparison post-test. Results: The results showed that organ weights were not affected but animal weights increased significantly (P < 0.01-0.001). Relative organ weights were not affected. The extract caused, at low doses, slight inflammation of the liver, spleen, lungs, kidneys and brain. With high dose of the extract, the spleen and lungs showed moderate inflammation. The lungs also showed moderate interstitial fibrosis. Conclusion: Based on these results, the plant has a potential to damage the lungs when used on the long term. Its use as herbal remedy should be for short periods at a time.

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Your work has been cited Dear Cheryl Lans, Congratulations - Your article has been cited. The information is based on your article's DOI (digital object identifier) and CrossRef (crossref.org).

Your article: Medicinal plant treatments for fleas and ear problems of cats and dogs in British Columbia, Canada Cited by: Russo, Rosario et al.: Pharmaco-Toxicological Aspects of Herbal Drugs Used in Domestic Animals Natural Product Communications. Volume: 4. Issue: 12. 2009 Katerere, David et al.: Ethnoveterinary Botanical Medicine. 2010 Neves, Arminda et al.: Ear mites: tackling a persistent problem The Veterinary Nurse. Volume: 1. Issue: 1. 2010 Umpiérrez, María Laura et al.: Plant essential oils as potential control agents of varroatosis Phytochemistry Reviews. Volume: 10. Issue: 2. 2011 Lans, Cheryl et al.: Organic parasite control for poultry and rabbits in British Columbia, Canada Journal of Ethnobiology and Ethnomedicine. Volume: 7. Issue: 1. 2011 Riaz, Muhammad et al.: Common mullein, pharmacological and chemical aspects Revista Brasileira de Farmacognosia. Volume: 23. Issue: 6. 2013 Kamiie, Yuki et al.: Essential oil composition of Lavandula angustifolia “Hidcote”: Comparison of hydrodistillation and supercritical fluid extraction methods Transactions of the Materials Research Society of Japan. Volume: 39. Issue: 4. 2014 Godara, R. et al.: In vitro acaricidal activity of ethanolic and aqueous floral extracts of Calendula officinalis against synthetic pyrethroid resistant Rhipicephalus (Boophilus) microplus Experimental and Applied Acarology. Volume: 67. Issue: 1. 2015

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COMPARATIVE EVALUATION OF AQUEOUS AND ETHANOL EXTRACTS OF MOMORDICA CHARANTIA SEED ON COAGULATION CASCADE AND PLATELET FUNCTION

https://www.researchgate.net/publication/333932374_COMPARATIVE_EVALUATION_OF_AQUEOUS_AND_ETHANOL_EXTRACTS_OF_MOMORDICA_CHARANTIA_SEED_ON_COAGULATION_CASCADE_AND_PLATELET_FUNCTION

CFP: 4th Annual Meeting of the Canadian Society for Environmental Philosophy

4th Annual Meeting of the Canadian Society for Environmental Philosophy/ Société Canadienne de Philosophie Environnementale (in conjunction with the 56th annual meeting of the Western Canadian Philosophical Association) October 25th-27, University of Lethbridge, Lethbridge, Alberta

CSEP/SCPE KEYNOTE:

PAUL B. THOMPSON

W.K. KELLOGG CHAIR IN AGRICULTURAL, FOOD & COMMUNITY ETHICS

MICHIGAN STATE UNIVERSITY

WCPA KEYNOTE:

ANDREW LIGHT

UNIVERSITY PROFESSOR OF PHILOSOPHY, PUBLIC POLICY, AND ATMOSPHERIC SCIENCES

GEORGE MASON UNIVERSITY

Submissions of papers from all areas of environmental philosophy are welcome. Papers should be no more than 4,000 words (excluding notes), presentable in 25-30 minutes to allow for commentary and discussion, and prepared for anonymous review. The submission deadline is extended to JULY 15 2019.

Please submit papers in electronic form (PDF) and a brief abstract (no more than 150 words) via EasyChair:  https://easychair.org/conferences/?conf=wcpa2019conference

Proposals for panels or symposia are also welcome. Please submit the proposed title of the symposium as well as a collection of abstracts in electronic form (PDF), and a brief abstract (no more than 150 words) indicating that you are proposing a panel/symposium via EasyChair (in the same way as you would submit a paper). Symposia are allotted 2 hours.

Colloquium papers and panels/symposia on environmental topics may be submitted for presentation either on the WCPA main program or the program of the CSEP/SCPE, but will automatically be considered for presentation on both programs. Please indicate if you are submitting with the CSEP/SPCE in mind at the top of your abstract.The CSEP/CSPE will be awarding a Student Essay Prize, so if you are eligible, please indicate this.

For more information about the conference site at the University of Lethbridge, visit: http://www.uleth.ca/artsci/philosophy/western-canadian-philosophical-association-wcpa-conference

Roselle Seed Oil and its Nano-Formulation Alleviated Oxidative Stress, Activated Nrf2 and Downregulated m-RNA Expression Genes of Pro-inflammatory Cytokines in Paracetamol-intoxicated Rat Model

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Roselle (Hibiscus sabdariffa L.) seeds, traditionally used in liver disorders, have recently attracted more attention as a new source of healthy edible oil with anti-inflammatory and antioxidant activities. However, its hepatoprotective effect has not been explored yet. In the current study, the hepatoprotective potential of roselle seed oil (RSO; 0.6, 4 and 8 mL/kg) and its nano-formulation (RSO-NE; 4 and 8 mL/kg), and their possible underlying mechanism were investigated in a paracetamol-induced hepatotoxicity rat model, compared to silymarin. RSO and RSO-NE protected the liver against paracetamol-intoxication and maintained the overall architecture of liver tissues in a dose dependent manner. Additionally, hepatic nuclear factor-erythroid 2-related factor2 (Nrf2) and glutathione (GSH) increased significantly in pre-treated groups, while malondialdehyde (MDA) decreased. Moreover, RSO and RSO-NE significantly inhibited paracetamol-induced mRNA expression of pro-inflammatory cytokines (TNF-α and IL-6). Chemical analysis of RSO showed fatty acids (mainly linoleic, oleic, palmitic and stearic acids), n-eicosane, β-sitosterol and tocopherols as the major constituents, which contributed synergistically to its protective effect. The efficacy of RSO-NE (8 mL/kg) was superior to its corresponding unformulated oil (0.6 mL/kg), indicating its enhanced bioavailability. These findings encourage the use of RSO in development of health promoting products such as food supplements, functional food and nutraceuticals for the prevention of liver disease.

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https://www.researchgate.net/publication/333753679_Roselle_Seed_Oil_and_its_Nano-Formulation_Alleviated_Oxidative_Stress_Activated_Nrf2_and_Downregulated_m-RNA_Expression_Genes_of_Pro-inflammatory_Cytokines_in_Paracetamol-intoxicated_Rat_Model