Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C<sub>17</sub>-Sesquiterpenoids and a Study of Their Phytotoxic Activity

Cárdenas, David M.; Rial, Carlos; Varela, Rosa M.; Molinillo, José M. G.; Macías, Francisco A.

doi:10.1021/acs.jnatprod.1c00396

Cited by 7 publications

(7 citation statements)

References 34 publications

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“…Merosesquiterpenoids are a recently discovered group of natural products. [ 11‐12 ] These compounds have been found to have fascinating structures and exhibit relatively potent biological activities.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var. hupehensis and Their Anti‐inflammatory Activities

Zhang

Yang

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryIn this study, 27 new sesquiterpenoids: twenty monomers and seven dimers, with diverse structures, along with one known chlorajaponilide F (25) were isolated from the aerial parts of Chloranthus henryi var. hupehensis. Structurally, chlorahupetolides A (1) and B (2), two eudesmane‐type merosesquiterpenoids with an undescribed C18 carbon framework, and chlorahupetene E (18) are the first example of dimers comprising two eudesmane sesquiterpenoids bridged by a four‐membered ring in the Chloranthus. Their structures were characterized by nuclear magnetic resonance (NMR), electronic circular dichroism (ECD), and X‐ray diffraction analysis. In the RAW264.7 macrophages model of inflammation induced by LPS, compounds 12, 18, and 25 significantly reduced NO production in a dose dependent manner and without cytotoxicity. The mRNA expression of COX‐2 was considerably inhibited by treatments with compounds 12, 18, and 25.

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Section: Background and Originality Contentmentioning

confidence: 99%

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var. hupehensis and Their Anti‐inflammatory Activities

Zhang

Yang

et al. 2023

Chin. J. Chem.

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“…Only a few medical activities have been reported; [13][14][15][16] however, no information on their application in agriculture can be found. In our previous reports, 19,20 we noticed that some of the C 17 -sesquiterpenoids, as well as some intermediates synthesized without the ⊍-methylene-γ-butyrolactone moiety presented good phytotoxic activity, in some cases even better than the parent SL. This fact attracted our attention that these molecules may hide a key to a possible novel MoA.…”

Section: Introductionmentioning

confidence: 79%

“…Isoalantolactone (1) and alantolactone (4) were isolated by column chromatography from Inula helenium roots and dehydrocostuslactone (7) was isolated by the same means from Saussurea lappa root extract. A detailed description of the isolation procedures and the synthesis of all the molecules tested (2, 3, 5, 6 and 8–14) was described in our previous works 19,20 …”

Section: Methodsmentioning

confidence: 99%

“…A detailed description of the isolation procedures and the synthesis of all the molecules tested (2, 3, 5, 6 and 8-14) was described in our previous works. 19,20 2.2 Seeds and fungi origin S. lycopersicum, L. sativa (cv Romana), A. cepa and L. sativum seeds were generously provided by FITÓ. E. crus-galli and L. perenne seeds were purchased from Herbiseed (Reading, UK).…”

Section: Isolation and Synthesis Of The Tested Moleculesmentioning

confidence: 99%

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Evaluation of the phytotoxic and antifungal activity of C₁₇‐sesquiterpenoids as potential biopesticides

Cárdenas

Bajsa‐Hirschel

Cantrell

et al. 2022

Pest Management Science

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BACKGROUND Natural products are a promising source for the development of new pesticides with alternative mechanisms of action. In this study, we evaluated the phytotoxic and antifungal activity of a novel family of natural C17‐sesquiterpenoids and performed a study of the effect caused by the elimination of the α‐methylene‐γ‐butyrolactone system and its importance to their biological activity. RESULTS Many tested compounds exhibited a strong phytotoxic activity. Lappalone and pertyolide B were the most potent molecules from the tested group. Lappalone displayed a strong inhibition profile against selected weed species, reaching a half‐maximal inhibitory concentration (IC50) value of 5.0 μm against Echinochloa crus‐galli L. shoot and 5.7 μm against the germination rate of Amaranthus viridis L., as well as a good stimulation of the germination of Phelipanche ramosa L. Pertyolide B demonstrated excellent inhibition against Amaranthus viridis L. (IC50: 56.7, 70.3 and 24.0 μm against the root and shoot growth, and germination rate, respectively) and Allium cepa L. (representative of the Liliaceae family, with IC50 values of 25.3 and 64.4 μm against root and shoot growth). Regarding the antifungal activity, pertyolide B presented significant activity against Colletotrichum fragareae and Fusarium oxysporum with a minimum inhibitory concentration of 6.6 μg μL−1. CONCLUSION The bioassays revealed that frequently the presence of the α‐methylene‐γ‐butyrolactone system is not essential for the bioactivities of sesquiterpene lactones, and suggest that C17‐sesquiterpenoids may function through a different mechanism of action not related to the widely assumed Michael addition. © 2022 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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“…The guaianolide-type skeleton of sesquiterpene lactones makes these substances some of the most promising phytotoxic secondary metabolites employed as natural product-based herbicides. − The application of allelopathy is crucial for the sustainable development of agriculture, and sesquiterpene lactones, which are released by plants to defend themselves against other plants that are competing for resources, have played a key role as lead compounds in this field. Cynara cardunculus is a good source of these sesquiterpene lactones, with aguerin B ( 1 ), cynaropicrin ( 2 ), and grosheimin ( 3 ) (Figure ) being perhaps the most abundant and active guaianolides.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of Cynara Cardunculus Guaiane-type Lactones in Fully Organic Nanotubes Enhances Their Phytotoxic Properties

Mejías

Fernández

Rial

et al. 2022

J. Agric. Food Chem.

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The encapsulation of bioactive natural products has emerged as a relevant tool for modifying the poor physicochemical properties often exhibited by agrochemicals. In this regard, natural guaiane-type sesquiterpene lactones isolated from Cynara cardunculus L. have been encapsulated in a core/shell nanotube@agrochemical system. Monitoring of the F and O signals in marked sesquiterpenes confirmed that the compound is present in the nanotube cavity. These structures were characterized using scanning transmission electron microscopy–X-ray energy-dispersive spectrometry techniques, which revealed the spatial layout relationship and confirmed encapsulation of the sesquiterpene lactone derivative. In addition, biological studies were performed with aguerin B (1), cynaropicrin (2), and grosheimin (3) on the inhibition of germination, roots, and shoots in weeds (Phalaris arundinacea L., Lolium perenne L., and Portulaca oleracea L.). Encapsulation of lactones in nanotubes gives better results than those for the nonencapsulated compounds, thereby reinforcing the application of fully organic nanotubes for the sustainable use of agrochemicals in the future.

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Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C₁₇-Sesquiterpenoids and a Study of Their Phytotoxic Activity

Cited by 7 publications

References 34 publications

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var. hupehensis and Their Anti‐inflammatory Activities

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var. hupehensis and Their Anti‐inflammatory Activities

Evaluation of the phytotoxic and antifungal activity of C₁₇‐sesquiterpenoids as potential biopesticides

Encapsulation of Cynara Cardunculus Guaiane-type Lactones in Fully Organic Nanotubes Enhances Their Phytotoxic Properties

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Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C17-Sesquiterpenoids and a Study of Their Phytotoxic Activity

Cited by 7 publications

References 34 publications

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var. hupehensis and Their Anti‐inflammatory Activities

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var. hupehensis and Their Anti‐inflammatory Activities

Evaluation of the phytotoxic and antifungal activity of C17‐sesquiterpenoids as potential biopesticides

Encapsulation of Cynara Cardunculus Guaiane-type Lactones in Fully Organic Nanotubes Enhances Their Phytotoxic Properties

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Product

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Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C₁₇-Sesquiterpenoids and a Study of Their Phytotoxic Activity

Evaluation of the phytotoxic and antifungal activity of C₁₇‐sesquiterpenoids as potential biopesticides