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11 pages, 1745 KB

Open AccessArticle

A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity

by Felipe Escobar-Montaño, Antonio J. Macías-Sánchez, José M. Botubol-Ares, Rosa Durán-Patrón and Rosario Hernández-Galán

Plants 2024, 13(6), 842; https://doi.org/10.3390/plants13060842 - 14 Mar 2024

Cited by 2 | Viewed by 1833

Abstract

Premyrsinane-type diterpenoids have been considered to originate from the cyclization of a suitable 5,6- or 6,17-epoxylathyrane precursor. Their biological activities have not been sufficiently explored to date, so the development of synthetic or microbial approaches for the preparation of new derivatives would be desirable. Epoxyboetirane A (4) is an 6,17-epoxylathyrane isolated from Euphorbia boetica in a large enough amount to be used in semi-synthesis. Transannular cyclization of 4 mediated by Cp₂Ti^IIICl afforded premyrsinane 5 in good yield as an only diasteroisomer. To enhance the structural diversity of premyrsinanes so their potential use in neurodegenerative disorders could be explored, compound 5 was biotransformed by Mucor circinelloides NRRL3631 to give rise to hydroxylated derivatives at non-activated carbons (6–7), all of which were reported here for the first time. The structures and absolute configurations of all compounds were determined through extensive NMR and HRESIMS spectroscopic studies. Full article

(This article belongs to the Section Phytochemistry)

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32 pages, 5158 KB

Open AccessReview

Myrsinane-Type Diterpenes: A Comprehensive Review on Structural Diversity, Chemistry and Biological Activities

by Eduarda Mendes, Cátia Ramalhete and Noélia Duarte

Int. J. Mol. Sci. 2024, 25(1), 147; https://doi.org/10.3390/ijms25010147 - 21 Dec 2023

Cited by 10 | Viewed by 3587

Abstract

Euphorbia species are important sources of polycyclic and macrocyclic diterpenes, which have been the focus of natural-product-based drug research due to their relevant biological properties, including anticancer, multidrug resistance reversal, antiviral, and anti-inflammatory activities. Premyrsinane, cyclomyrsinane, and myrsinane diterpenes are generally and collectively designated as myrsinane-type diterpenes. These compounds are derived from the macrocyclic lathyrane structure and are characterized by having highly oxygenated rearranged polycyclic systems. This review aims to describe and summarize the distribution and diversity of 220 myrsinane-type diterpenes isolated in the last four decades from about 20 Euphorbia species. Some myrsinane diterpenes obtained from Jatropha curcas are also described. Discussion on their plausible biosynthetic pathways is presented, as well as isolation procedures and structural elucidation using nuclear magnetic resonance spectroscopy. Furthermore, the most important biological activities are highlighted, which include cytotoxic and immunomodulatory activities, the modulation of efflux pumps, the neuroprotective effects, and the inhibition of enzymes such as urease, HIV-1 reverse transcriptase, and prolyl endopeptidase, among other biological effects. Full article

(This article belongs to the Special Issue Natural Product Chemistry and Biological Research)

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22 pages, 1482 KB

Open AccessArticle

LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity

by Milka Jadranin, Danica Savić, Ema Lupšić, Ana Podolski-Renić, Milica Pešić, Vele Tešević, Slobodan Milosavljević and Gordana Krstić

Plants 2023, 12(24), 4181; https://doi.org/10.3390/plants12244181 - 16 Dec 2023

Cited by 2 | Viewed by 3085

Abstract

Euphorbia seguieriana ssp. seguieriana Necker (ES) and Euphorbia cyparissias (EC) with a habitat in the Deliblato Sands were the subject of this examination. The latexes of these so far insufficiently investigated species of the Euphorbia genus are used in traditional medicine for the treatment of wounds and warts on the skin. To determine their chemical composition, non-targeted screening of the latexes’ chloroform extracts was performed using liquid chromatography coupled with quadrupole time-of-flight mass spectrometry employing an electrospray ionization source (LC-ESI QTOF MS). The analysis of the obtained results showed that the latexes of ES and EC represent rich sources of diterpenes, tentatively identified as jatrophanes, ingenanes, tiglianes, myrsinanes, premyrsinanes, and others. Examination of the anticancer activity of the ES and EC latex extracts showed that both extracts significantly inhibited the growth of the non-small cell lung carcinoma NCI-H460 and glioblastoma U87 cell lines as well as of their corresponding multi-drug resistant (MDR) cell lines, NCI-H460/R and U87-TxR. The obtained results also revealed that the ES and EC extracts inhibited the function of P-glycoprotein (P-gp) in MDR cancer cells, whose overexpression is one of the main mechanisms underlying MDR. Full article

(This article belongs to the Special Issue New Insights in the Research of Bioactive Compounds from Plant Origin with Nutraceutical and Pharmaceutical Potential II)

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12 pages, 1891 KB

Open AccessArticle

Diterpenoids from Euphorbia gedrosiaca as Potential Anti-Proliferative Agents against Breast Cancer Cells

by Zeinab Yazdiniapour, Mohammad Hossein Sohrabi, Newsha Motinia, Behzad Zolfaghari, Pegah Mehdifar, Mustafa Ghanadian and Virginia Lanzotti

Metabolites 2023, 13(2), 225; https://doi.org/10.3390/metabo13020225 - 3 Feb 2023

Cited by 7 | Viewed by 2615

Abstract

Isolated diterpenes from various species of Euphorbia are important compounds for drug discovery with a broad spectrum of structures and biological effects. In this study, Euphorbia gedrosiaca, one of the endemic species of Iran, was analyzed in terms of the presence and structural determination of diterpenoid compounds. They were extracted with dichloromethane/acetone (2:1) from aerial parts of this plant and purified by chromatographic methods such as MPLC and HPLC. Four premyrsinane compounds and one myrsinane diterpene were isolated from Euphorbia gedrosiaca. They were characterized by extensive 1D and 2D NMR and HRMS analyses. Additionally, their activities were evaluated against two breast cancer cell lines, MDA-MB-231 and MCF-7, by MTT proliferation assay. They exhibited cytotoxic effects in a dose-dependent manner with promising results, which can help to find possible therapeutic application of diterpenoids in breast cancer treatment. Full article

(This article belongs to the Special Issue Natural Products: Chemical Profiling, Computational Studies and Bioactivities)

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13 pages, 1397 KB

Open AccessArticle

Euphosantianane E–G: Three New Premyrsinane Type Diterpenoids from Euphorbia sanctae-catharinae with Contribution to Chemotaxonomy

by Abdelsamed I. Elshamy, Tarik A. Mohamed, Saud L. Al-Rowaily, Ahmed M. Abd-ElGawad, Basharat A. Dar, Abdelaaty A. Shahat and Mohamed-Elamir F. Hegazy

Molecules 2019, 24(13), 2412; https://doi.org/10.3390/molecules24132412 - 29 Jun 2019

Cited by 22 | Viewed by 3941

Abstract

Euphorbia species were widely used in traditional medicines for the treatment of several diseases. From the aerial parts of Egyptian endemic plant, Euphorbia sanctae-catharinae, three new premyrsinane diterpenoids, namely, euphosantianane E–G (1–3), alongside four known triterpenes, 9,19-cyclolanostane-3β,24S-diol (4), 25-methoxycycloartane-3β,24S-diol (5), 25-methylenecycloartan-3β,24R-diol (6), and 25-methylenecycloartan-3β,24S-diol (7), were isolated and identified. The chemical structures were proven depending upon spectroscopic analysis, including FTIR, HRFABMS, and 1D/2D-NMR. The chemotaxonomic significance of the isolated compounds, especially diterpenes from E. sanctae-catharinae compared to those documented from different Euphorbia species was also studied via agglomerative hierarchical clustering (AHC). The Egyptian endemic Euphorbia sanctae-catharina was grouped with E. bupleuroides, E. fidjiana, E. fischeriana, E. pithyusa subsp. cupanii, E. prolifera, and E. seguieriana, where myrsinol diterpenoids were the characteristic compounds. Full article

(This article belongs to the Section Medicinal Chemistry)

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16 pages, 2792 KB

Open AccessReview

Macrocyclic Diterpenoids from Euphorbiaceae as A Source of Potent and Selective Inhibitors of Chikungunya Virus Replication

by Simon Remy and Marc Litaudon

Molecules 2019, 24(12), 2336; https://doi.org/10.3390/molecules24122336 - 25 Jun 2019

Cited by 25 | Viewed by 5546

Abstract

Macrocyclic diterpenoids produced by plants of the Euphorbiaceae family are of considerable interest due to their high structural diversity; and their therapeutically relevant biological properties. Over the last decade many studies have reported the ability of macrocyclic diterpenoids to inhibit in cellulo the cytopathic effect induced by the chikungunya virus. This review; which covers the years 2011 to 2019; lists all macrocyclic diterpenoids that have been evaluated for their ability to inhibit viral replication. The structure–activity relationships and the probable involvement of protein kinase C in their mechanism of action are also detailed. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products)

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12 pages, 2227 KB

Open AccessArticle

Euphosantianane A–D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae

by Mohamed-Elamir F. Hegazy, Ahmed R. Hamed, Mahmoud A. A. Ibrahim, Zienab Talat, Eman H. Reda, Nahla S. Abdel-Azim, Faiza M. Hammouda, Seikou Nakamura, Hisashi Matsuda, Eman G. Haggag, Paul W. Paré and Thomas Efferth

Molecules 2018, 23(9), 2221; https://doi.org/10.3390/molecules23092221 - 1 Sep 2018

Cited by 22 | Viewed by 4803

Abstract

Euphorbia species are rich in diterpenes. A solvent extraction of Euphorbia sanctae-catharinae, a species indigenous to the Southern Sinai of Egypt, afforded several premyrsinane diterpenoids (1–4) as well as previously reported metabolites (5–13) that included three flavonoids. Isolated compounds were chemically characterized by spectroscopic analysis. Identified compounds were bioassayed for anti-proliferative activity in vitro against colon (Caco-2) and lung (A549) tumor cell lines. Compound 9 exhibited robust anti-proliferative activity against A549 cells (IC₅₀ = 3.3 µM). Absolute configurations for 8 versus 9 were determined by experimental and TDDFT-calculated electronic circular dichorism (ECD) spectra. Full article

(This article belongs to the Section Medicinal Chemistry)

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