Three new prenylated flavonoids from Macaranga denticulata and their anticancer effects

Yang, Da‐Song; Li, Zi-Lei; Peng, Weibing; Yang, Yongping; Wang, Xue; Liu, Kechun; Li, Xiaoli; Xiao, Wei‐Lie

doi:10.1016/j.fitote.2015.04.001

Cited by 23 publications

(10 citation statements)

References 20 publications

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“…Analyses of ESI-MS and 1D-NMR, along with the comparison of spectral data in the literature established the structure of compound 3 as stigmast-4-ene-6β-ol-3-one or 6β-hydroxyenone. [8,9] Compound 4 was isolated as white solid. The ESI-MS of 4 appeared the pseudomolecular ion peak at m/z 427 [M+H] + .…”

Section: Extraction and Isolationmentioning

confidence: 99%

Chemical constitutents 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. 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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Section: Extraction and Isolationmentioning

confidence: 99%

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

Ngan

Phượng

et al. 2018

Vietnam Journal of Chemistry

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“…Analyses of ESI-MS and 1D-NMR, along with the comparision of spectral data in the literature established the structure of compound 3 as stigmast-4-ene-6β-ol-3-one or 6β-hydroxyenone. [8,9] Compound 4 was isolated as white solid. The ESI-MS of 4 appeared the pseudomolecular ion peak at m/z 427 [M+H] + .…”

Section: Resultsmentioning

confidence: 99%

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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“…The FT-IR showed absorption bands at v max 3414, 1657, 1610, and 1475 cm −1 indicating the presence of hydroxy, α , β -unsaturated carbonyl and aromatic ring functionalities, respectively. The UV absorption maximum at 366, 327, and 271 nm was typical for a flavonol-type compound [15]. The presence of a substituted flavonol skeleton was suggested by the analysis of 1 H and 13 C-NMR spectroscopic data (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Phenolic Compounds from Fruit Glandular Trichomes of Macaranga tanarius

Doan

Nguyễn

Trinh

et al. 2019

Journal of Analytical Methods in Chemistry

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A new flavonoid, macatanarin D (1), together with five known stilbenes (2-6), was isolated from fruit glandular trichomes of Macaranga tanarius. Their structures were elucidated on the basis of spectroscopic methods and through comparison with data reported in the literature. All isolated compounds were evaluated for their cytotoxic activities against KB and MCF-7 cell lines. Compounds 3, 4, and 5 showed the strongest activities against both cell lines with IC50 values in the range of 0.03–0.12 μM, and compound 2 only showed a significant cytotoxicity against KB cell line (IC50 = 0.26 μM) and a moderate cytotoxicity against MCF-7 (IC50 = 10.4 μM). Compounds 1 and 6 showed weak cytotoxic activities against KB cell line with IC50 values of 29.3 and 24.7 μM, respectively.

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Three new prenylated flavonoids from Macaranga denticulata and their anticancer effects

Cited by 23 publications

References 20 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)

Cytotoxic Phenolic Compounds from Fruit Glandular Trichomes of Macaranga tanarius

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