Flavonoids from Eight Tropical Plant Species That Inhibit the Multidrug Resistance Transporter ABCG2

Versiani, Muhammad Ali; Diyabalanage, Thushara; Ratnayake, Ranjala; Henrich, Curtis J.; Bates, Susan E.; McMahon, James B.; Gustafson, Kirk R.

doi:10.1021/np100797y

Cited by 28 publications

(15 citation statements)

References 30 publications

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“…Two milbemycin compounds (Gao et al, 2011), two novel acrylonitrile derivatives (Yamazaki et al, 2011), and a number of benzo(a)quinolizin-4-ones (Kanintronkul et al, 2011) showed chemosensitizing properties attributable to modulation of P-gp, whereas X-shaped poly-(ethylene oxide)-poly(propylene oxide) block copolymers (poloxamines) inhibited P-gp and BCRP in hepatic carcinoma cell lines (Cuestas et al, 2011). A number of flavonoid compounds from various plant species were shown to inhibit BCRP function (Versiani et al, 2011) and to inhibit vinblastine-stimulated P-gp activity but to promote daunorubicinstimulated P-gp activity in leukemic T cells (Tran et al, 2011). Limonin and other citrus compounds enhanced doxorubicin cytotoxicity in MDR CEM/ADR5000 leukemia cells (El-Readi et al, 2010).…”

Section: Downloaded Frommentioning

confidence: 99%

Drug Efflux Transporters and Multidrug Resistance in Acute Leukemia: Therapeutic Impact and Novel Approaches to Mediation

Xia

Smith

2012

Mol Pharmacol

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Section: Downloaded Frommentioning

confidence: 99%

Drug Efflux Transporters and Multidrug Resistance in Acute Leukemia: Therapeutic Impact and Novel Approaches to Mediation

Xia

Smith

2012

Mol Pharmacol

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“…This compound gave NMR parameter which is suitable with 4′-Omethyl-8-isoprenyleriodictyol from M. conifera [5].…”

Section: Resultsmentioning

confidence: 94%

Chemical Composition and Anticancer Activity of Macaranga hosei Leaves

Marliana¹,

Astuti²,

Kosala³

et al. 2018

Asian J. Chem.

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INTRODUCTIONMacaranga is one genus of the family Euphorbiaceae comprising of ± 300 species. In Indonesia, this plant known as "Mahang". The distribution of Macaranga plants is relatively wide, other than Indonesia, can also be found in Africa, Madagascar, Asia, the east coast of Australia and the Pacific islands [1].According to previous studies, phenolics such as flavonoids and stilbenoids can be isolated from this genus. The uniqueness of flavonoids and stilbenoids from this genus is the presence of terpenoids at aromatic core such as prenyl, geranyl, farnesyl and geranyl [2,3]. Prenylated flavonoids including flavanone derivatives mostly can be found in M. triloba, M. trichocarpa, M. conivera and M. lowii [3-6]. Flavonol derivatives can be obtained from M. gigantea, M. recurvate, M. pruinosa, M. rizhinoides and M. bicolor [2,5,7-9]. Dihydroflavone derivatives mostly can be attained in M. conivera, M. alnifolia, M. pruinosa and M. lowii [6,8,10,11].Previous studies have revealed that the presence of isoprenoid chains plays an important role for the biological activity of prenylated aromatic compounds which made them possess better bioactivity than their mother compounds without derivatization or modification [12] The anticancer activity of methanolic extract and ethyl acetate fraction of Macaranga hosei leaves against HeLa cell lines were evaluated by [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] (MTT) assay. Both extracts displayed anticancer activity with IC50 values of 36.18 and 7.01 µM, respectively, which can be suggested that M. hosei is a great potential source of anticancer agents. In addition, two isoprenylated flavanones, 4'-O-methyl-8-isoprenyl eriodictyol (1) and 6-isoprenyl eriodictyol (2) have been isolated from ethyl acetate fraction. The structures of both compounds have been elucidated based on their spectroscopic data, including 1D and 2D NMR spectra.

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“…Compound 1 depicted a negative Cotton effect originating from a π π* transition at 290 nm, and this was adequately indicative of a 2S configuration. 12,13) The stereochemistry of C-9 still remains to be determined since the inadequate rotating frame nuclear Overhauser enhancement spectroscopy (ROESY) correlations and the failure to obtain suitable crystal for single X-ray diffraction analysis. Based on these results, the structure of 1 (neougonin A) was assigned as 5,7,3′,4′-tetrahydroxy-6-(2,6-dimethyl-6-vinyl-2-hexenyl)-flavanone.…”

Section: Resultsmentioning

confidence: 99%

Anti-inflammatory Prenylated Flavonoids from <i>Helminthostachys zeylanica</i>

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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1) The rhizomes of H. zeylanica are used in a popular antipyretic and anti-inflammatory Chinese herbal medicine known as "Daodi-Ugon." 1,2) This plant has also been shown to exhibit hepatoprotective activity.3,4) Numerous bioactive flavonoids containing prenyl or geranyl groups have been isolated from the rhizomes of H. zeylanica.2-6) Our current systematic phytochemical investigation of this plant led to the isolation of two new prenylflavonoids, neougonins A (1) and B (2), along with nine known flavonoids (Fig. 1). In addition, compound 1 showed significant inhibition of nitric oxide (NO) production with an IC 50 value of 3.32 µM. We report herein the isolation, structural elucidation and biological evaluation of the isolated compounds. Results and DiscussionThe dried whole plants of H. zeylanica were extracted with 95% EtOH, and the concentrated extract was suspended in water and partitioned with EtOAc. The EtOAc fraction was subjected to repeated column chromatography (MCI CHP 20P, 75-150 µm), and octadecyl silica (ODS)) and semi-preparative HPLC to yield two new prenylated flavonoids, neougonins A (1) and B (2), together with nine known flavonoids.Compound 1 was isolated and purified as a yellow amorphous powder. A molecular ion peak at m/z 424.1887 in the high resolution-electron ionization (HR-EI)-MS indicated a molecular formula of C 25 H 28 O 6 , corresponding to 12 degrees of unsaturation. The IR spectrum of 1 showed the presence of hydroxy (ν max 3407 cm ) and carbonyl (ν max 1637 cm −1 ) groups. The UV spectrum showed a disparate course of spectra with maxima at 230 (sh) nm, 298 (sh) nm. Generally, the spectra corresponded to the π π* and n π* electronic transitions of the flavanone skeleton.

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Flavonoids from Eight Tropical Plant Species That Inhibit the Multidrug Resistance Transporter ABCG2

Cited by 28 publications

References 30 publications

Drug Efflux Transporters and Multidrug Resistance in Acute Leukemia: Therapeutic Impact and Novel Approaches to Mediation

Drug Efflux Transporters and Multidrug Resistance in Acute Leukemia: Therapeutic Impact and Novel Approaches to Mediation

Chemical Composition and Anticancer Activity of Macaranga hosei Leaves

Anti-inflammatory Prenylated Flavonoids from <i>Helminthostachys zeylanica</i>

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