Clerodanes and other constituents of Cleidion spiciflorum

Macaranga denticulata is a 15‐18 m tall plant with rounded edges and long, rounded bark, 5 mm wide black covered with glands. In traditional medicine, this plant was used to treat fulminant hepatitis, dysentery, and urinary retention. In previous studies, we reported 13 isolated compounds from the fruits of Macaranga denticulata. This work presented the isolation and structural characterizations of seven compounds: 5‐((E)‐3,5‐dihydroxystyryl)‐3‐((E)‐3,7‐dimethylocta‐2,6‐dien‐1‐yl)benzen‐1,2‐diol (1), poilaneic acid (2), stigmast‐4‐en‐6β‐ol‐3‐one (3), epi‐taraxerol (4), rel‐5‐(3S,8S‐dihydroxy‐1R,5S‐dimethyl‐7‐oxa‐6‐oxobicyclo[3,2,1]‐oct‐8‐yl)3‐methyl, 2Z,4E‐pentadienoic acid (5), ellagic acid 3,3'‐dimethyl ether‐4‐O‐β‐D‐glucopyranoside (6), 3‐hydroxypropanoic acid (7). The structures of the isolated compounds were elucidated from their mass and NMR spectral data.

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“…Analyses of 13 13 C-NMR, and comparison with reported data [10,11] established compound 4 as epitaraxerol.…”

Section: Extraction and Isolationmentioning

confidence: 95%

Chemical constitutents from fruits of Macaranga denticulata (Euphorbiaceae) (Part 2)

Ngan

Phượng

et al. 2018

Vietnam Journal of Chemistry

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“…The 13 C-NMR and DEPT of 4 spectra showed the signals of 30 carbons, including eight methyl groups, ten methylene groups, five methine groups and seven quaternary carbons. Analyses of 13 13 C-NMR, and comparision with reported data [10,11] established compound 4 as epitaraxerol. 2 and an E-form of an olefin moiety in the molecule.…”

Section: Resultsmentioning

confidence: 70%

Chemical constituents from fruits of Macaranga denticulata (Euphorbiaceae) (Part 2)

Ngan

Phượng

et al. 2018

Vietnam Journal of Chemistry

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Macaranga denticulata is a 15‐18 m tall plant with rounded edges and long, rounded bark, 5 mm wide black covered with glands. In traditional medicine, this plant was used to treat fulminant hepatitis, dysentery, and urinary retention. In previous studies, we reported 13 isolated compounds from the fruits of Macaranga denticulata. In this study, we describe the isolation and structural characterizations of seven compounds: 5‐((E)‐3,5‐dihydroxystyryl)‐3‐((E)‐3,7‐dimethylocta‐2,6‐dien‐1‐yl)benzen‐1,2‐diol (1), poilaneic acid (2), stigmast‐4‐en‐6β‐ol‐3‐one (3), taraxerol (4), rel‐5‐(3S, 8S‐dihydroxy‐1R,5S‐dimethyl‐7‐oxa‐6‐oxobicyclo[3,2,1]‐oct‐8‐yl)3‐methyl, 2Z,4E‐pentadienoic acid (5), ellagic acid 3,3'‐dimethyl ether‐4‐O‐β‐D‐glucopyranoside (6), 3‐hydroxypropanoic acid (7). The structures of the isolated compounds were established on the basis of their spectral data, including mass and NMR spectrometry.

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“…Their structures were assigned on the basis of NMR analysis, ESI and HRESI mass spectrometry, and chemical methods. The known compounds were identified as chavicol β- d -glucopyranoside ( 1 ), 2-de- O -methyleugenol β- d -glucopyranoside ( 2 ), anol β- d -glucopyranoside ( 3 ), bractin ( 6 ), ellagic acid ( 12 ), and gallic acid ( 13 ) by their spectroscopic and physicochemical data.…”

Section: Resultsmentioning

confidence: 99%

“…Their structures were assigned on the basis of NMR analysis, ESI and HRESI mass spectrometry, and chemical methods. The known compounds were identified as chavicol β-D-glucopyranoside (1), 23 2-de-O-methyleugenol β-D-glucopyranoside (2), 23 anol β-D-glucopyranoside (3), 24 bractin (6), 25 ellagic acid (12), 26 and gallic acid (13) 27 by their spectroscopic and physicochemical data. The molecular formula of brevipetin A (4) was deduced as C 15 H 20 O 7 based on the sodium adduct ion, [M + Na] + (m/z 335.1108), in the HRESIMS data (calcd for C 15 H 20 O 7 Na, 335.1107), and this formula corresponds to six indices of hydrogen deficiency.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Anti-inflammatory Ellagitannins from Cleidion brevipetiolatum for the Treatment of Rheumatoid Arthritis

et al. 2019

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Six new ellagitannins, brevipetins B–G (5 and 7–11), and a new phenolic glucoside, brevipetin A (4), along with six known compounds were isolated from the traditional Chinese medicinal plant Cleidion brevipetiolatum. Their structures and absolute configurations were determined by spectroscopic analyses, chemical methods, and TD-DFT-ECD calculations. Compounds 5–11 exhibited NO inhibitory effects with IC50 values of 1.9–8.2 μM, and 9 showed the most potent inhibitory effect (IC50: 1.9 μM). An in vivo anti-inflammatory assessment of 9 showed that it exerts therapeutic effects in both the carrageenan-induced rat paw edema and collagen-induced arthritis (CIA) models at 50 mg/kg oral administration. The enhanced protein and mRNA expression levels of iNOS (inducible nitric oxide synthase) and COX-2 (cyclooxygenase-2) in LPS-stimulated RAW 264.7 cells were dose-dependently suppressed by 9. An anti-inflammatory mechanistic study revealed that 9 suppressed NF-κB activity by inhibiting IκBα phosphorylation and blocking translocation of p65 from the cytosol to the nucleus. Therefore, 9 might have the potential to be developed as a lead compound for relieving rheumatoid arthritis.

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Clerodanes and other constituents of Cleidion spiciflorum

Cited by 7 publications

References 14 publications

Chemical constitutents from fruits of Macaranga denticulata (Euphorbiaceae) (Part 2)

Chemical constitutents from fruits of Macaranga denticulata (Euphorbiaceae) (Part 2)

Chemical constituents from fruits of Macaranga denticulata (Euphorbiaceae) (Part 2)

Anti-inflammatory Ellagitannins from Cleidion brevipetiolatum for the Treatment of Rheumatoid Arthritis

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