Macrocyclic Diterpenoids from <i>Euphorbia helioscopia</i> and Their Potential Anti-inflammatory Activity

Su, Jun-Cheng; Cheng, Wen; Song, Jian-Guo; Zhong, Yuan‐Lin; Huang, Xiao‐Jun; Jiang, Ren‐Wang; Li, Man‐Mei; Ye, Wen‐Cai; Wang, Ying

doi:10.1021/acs.jnatprod.9b00519

Cited by 44 publications

(33 citation statements)

References 45 publications

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“…The crystallographic data of 3 was collected by using a Rigaku Oxford Diffraction Supernova diffractometer. The crystallographic structure of 3 was solved and refined by using similar methods reported in the literature . The standard CIF file of 3 was deposited with the Cambridge Crystallographic Data Centre with CCDC number of 1983273.…”

Section: Methodsmentioning

confidence: 99%

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

Xia

Chen

Wang

et al. 2020

Chemistry & Biodiversity

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Three new indole diketopiperazine alkaloids, 11-methylneoechinulin E and variecolorin M, and (+)-variecolorin G, along with 12 known analogs, were isolated from a soft coral-associated epiphytic fungus Aspergillus sp. EGF 15-0-3. The structures of the new compounds were unambiguously established by extensive spectroscopic analyses including HR-ESI-MS, 1D and 2D NMR spectroscopy and optical rotation measurements. The absolute configurations of (+)-and (À )-variecolorin G were determined by experimental and quantum-chemical ECD investigations and single-crystal X-ray diffraction analysis. Variecolorin G is a pair of enantiomeric mixtures with a ratio of 1 : 2. Moreover, (+)-neoechinulin A is firstly reported as a natural product. The cytotoxic activities of all the isolated compounds against NCI-H1975 gefitinib resistance (NCI-H1975/GR) cell lines were preliminarily evaluated by MTT method.

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Section: Methodsmentioning

confidence: 99%

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

Xia

Chen

Wang

et al. 2020

Chemistry & Biodiversity

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“…Protein kinase C activation and platelet stimulation abilities [52] E. helioscopia jatrophane (n = 10) Cytotoxic, inhibitory (nitric oxide (NO) [50,64] E. hylonoma ent-isopimarane (n = 9), ent-rosane (n = 1) Inhibitory (NO) [45] E. kansuensis…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

et al. 2021

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Euphorbia species have a rich history of ethnomedicinal use and ethnopharmacological applications in drug discovery. This is due to the presence of a wide range of diterpenes exhibiting great structural diversity and pharmacological activities. As a result, Euphorbia diterpenes have remained the focus of drug discovery investigations from natural products. The current review documents over 350 diterpenes, isolated from Euphorbia species, their structures, classification, biosynthetic pathways, and their structure–activity relationships for the period covering 2013–2020. Among the isolated diterpenes, over 20 skeletal structures were identified. Lathyrane, jatrophane, ingenane, ingenol, and ingol were identified as the major diterpenes in most Euphorbia species. Most of the isolated diterpenes were evaluated for their cytotoxicity activities, multidrug resistance abilities, and inhibitory activities in vitro, and reported good activities with significant half-inhibitory concentration (IC50) values ranging from 10–50 µM. The lathyranes, isopimaranes, and jatrophanes diterpenes were further found to show potent inhibition of P-glycoprotein, which is known to confer drug resistance abilities in cells leading to decreased cytotoxic effects. Structure–activity relationship (SAR) studies revealed the significance of a free hydroxyl group at position C-3 in enhancing the anticancer and anti-inflammatory activities and the negative effect it has in position C-2. Esterification of this functionality, in selected diterpenes, was found to enhance these activities. Thus, Euphorbia diterpenes offer a valuable source of lead compounds that could be investigated further as potential candidates for drug discovery.

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“…At the same time, the special chemic shifts of the natural product can be an effective probe to finger out the unique structure fragments of the metabolites from the complicated secondary metabolites [15][16][17][18]. Guided by 1 H NMR spectroscopic experiments, 11 macrocyclic diterpenes were isolated from the aerial parts of Euphorbia helioscopia using the aromatic protons as probes [17]. The assigned 1 H and 13 C chemical shifts leaded to the targeted isolation of a series of identified spiro compounds from Carthamus oxyacantha [18].…”

Section: Introductionmentioning

confidence: 99%

Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Guo

Zou

2020

Molecules

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Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), and two known compounds, pestaloficin C (3) and arthrinone (4). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds 1–2 were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.

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Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity

Cited by 44 publications

References 45 publications

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

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