Anacolosins A–F and Corymbulosins X and Y, Clerodane Diterpenes from <i>Anacolosa clarkii</i> Exhibiting Cytotoxicity toward Pediatric Cancer Cell Lines

Cai, Shengxin; Risinger, April L.; Petersen, Cora L.; Grkovic, Tanja; O’Keefe, Barry R.; Mooberry, Susan L.; Cichewicz, Robert H.

doi:10.1021/acs.jnatprod.8b01015

Cited by 19 publications

(16 citation statements)

References 18 publications

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“…Their relative and AC were assessed using a combination of 1 H NMR coupling constant data, ROESY experiments, ECD, and VCD spectroscopy. 59 A sample of 9,12-cyclomulin-13-ol (91) ( Figure 25), a constituent of Azorella and Laretia species, becomes available from Laretia acaulis. Its AC has been established by VCD in combination with DFT calculations.…”

Section: Monoterpenoids the Formulas Of The 28 Monoterpenoids Includmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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Section: Monoterpenoids the Formulas Of The 28 Monoterpenoids Includmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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“…The molecular formula of cuscutaroside B ( 2 ) was determined to be C 17 H 24 O 9 based on the 13 C NMR data (Table 1 ) and the HRESIMS ion peak at m/z 395.1313 [M + Na] + (calcd for C 17 H 24 NaO 9 , 395.1318). The 1 H and 13 C NMR data of 2 (Table 1 ) indicated the presence of one 6-methyl-2 H -pyran-2-one moiety ( δ C 171.3, 167.2, 164.8, 101.5, and 91.6) [ 12 ], one β -glucopyranosyl group [ δ H 5.05 (d, J = 7.5 Hz)], and one 2-methylbutyryl group ( δ C 178.2, 42.3, 27.9, 17.0, and 11.9) [ 13 ]. Compound 2 was deduced as a 2-methylbutyryl derivative of 4-( β -glucopyranosyloxy)-6-methyl-2 H -pyran-2-one by the COSY and HMBC correlations (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The molecular formula of cuscutaroside B (2) was determined to be C 17 H 24 O 9 based on the 13 C NMR data (Table 1) [13]. Compound 2 was deduced as a 2-methylbutyryl derivative of 4-(β-glucopyranosyloxy)-6-methyl-2H-pyran-2-one by the COSY and HMBC correlations (Fig.…”

Section: Structural Elucidationmentioning

confidence: 99%

Chemical Constituents from the Whole Plant of Cuscuta reflexa

Aung

Xia

Hein

et al. 2020

Nat. Prod. Bioprospect.

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Two new 2H-pyran-2-one glucosides, cuscutarosides A (1) and B (2), and one new steroidal glucoside, 7β-methoxy-β-sitosterol 3-O-β-glucopyranoside (3), together with 12 known compounds (4–15) were isolated from the whole plant of Cuscuta reflexa (Convolvulaceae) collected from Myanmar. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. The antiobesity activity of these isolates was evaluated using porcine pancreatic lipase (PPL), and the antiplatelet aggregation activity was screened using rabbit platelets induced by thrombin, platelet-activating factor (PAF), arachidonate (AA), or collagen. 7β-Methoxy-β-sitosterol 3-O-β-glucopyranoside (3) showed weak PPL inhibitory activity. Cuscutaroside A (1), its acetylated derivative (1a), and scrophenoside B (8) showed weak inhibitory activity against rabbit platelet aggregation induced by collagen. Compound 1a also showed inhibitory activity against rabbit platelet aggregation induced by AA. Graphic Abstract

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“…Most anticancer drugs are accompanied by side-effects and nonspecificity. Hence, there is a great interest in finding safe, selective, and effective anticancer drugs [23,24]. In this regard, human cancer cell lines are considered essential models to evaluate the efficacy of anticancer agents, with breast, liver, colon, and prostate cell lines being the four major types of cell lines tested [25,26].…”

Section: Introductionmentioning

confidence: 99%

Characterization of Possible α-Glucosidase Inhibitors from Trigonella stellata Extract Using LC–MS and In Silico Molecular Docking

Elwekeel

Amir

Mohamed

et al. 2022

Plants

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The current study accentuates the significance of performing the multiplex approach of LC-HRESIMS, biological activity, and docking studies in drug discovery, taking into consideration a review of the literature. In this regard, the investigation of antioxidant and cytotoxic activities of Trigonella stellata collected from the Egyptian desert revealed a significant antioxidant capacity using DPPH with IC50 = 656.9 µg/mL and a moderate cytotoxicity against HepG2, MCF7, and CACO2, with IC50 values of 53.3, 48.3, and 55.8 µg/mL, respectively. The evaluation of total phenolic and flavonoid contents resulted in 32.8 mg GAE/g calculated as gallic acid equivalent and 5.6 mg RE/g calculated as rutin equivalent, respectively. Chemical profiling of T. stellata extract, using LC-HRESIMS analysis, revealed the presence of 15 metabolites, among which eleven compounds were detected for the first time in this species. Interestingly, in vitro testing of the antidiabetic activity of the alcoholic extract noted an α-glucosidase enzyme inhibitory activity (IC50 = 559.4 µg/mL) better than that of the standard Acarbose (IC50 = 799.9 µg/mL), in addition to a moderate inhibition of the α-amylase enzyme (IC50 = 0.77 µg/mL) compared to Acarbose (IC50 = 0.21 µg/mL). α-Glucosidase inhibition was also virtualized by binding interactions through the molecular docking study, presenting a high binding activity of six flavonoid glycosides, as well as the diterpenoid compound graecumoside A and the alkaloid fenugreekine. Taken together, the conglomeration of LC-HRESIMS, antidiabetic activity, and molecular docking studies shed light on T. stellata as a promising antidiabetic herb.

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Anacolosins A–F and Corymbulosins X and Y, Clerodane Diterpenes from Anacolosa clarkii Exhibiting Cytotoxicity toward Pediatric Cancer Cell Lines

Cited by 19 publications

References 18 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Chemical Constituents from the Whole Plant of Cuscuta reflexa

Characterization of Possible α-Glucosidase Inhibitors from Trigonella stellata Extract Using LC–MS and In Silico Molecular Docking

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