New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae

Nguyen, Phi Hung; Sharma, Govinda; Đào, Trọng Tuấn; Uddin, Mohammad Nasir; Kang, Keon Wook; Ndinteh, Derek Tantoh; Mbafor, Joseph Tanyi; Oh, Won Keun

doi:10.1016/j.bmc.2012.08.024

Cited by 43 publications

(26 citation statements)

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“…Both species are indigenous to West Africa and are used as medicinal plants to treat a number of ailments. Isoflavonoids from this species have shown PTP1B inhibition and cytotoxic activity, which give the plant potential to be used as anticancer treatment [16,17]. Extracts from E. mildbraedii are used to treat stomach problems and various diseases associated with bacterial infection, asthma, female infertility, ulcers, and inflammations [36,37].…”

Section: Computational Methodologymentioning

confidence: 99%

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Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

et al. 2020

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This study was aimed at isolating hypaphorine from Erythrina mildbraedii Harms (Fabaceae) and Erythrina addisioniae Hutch. & Datziel (Fabaceae) in order to determine its structural and antibacterial effects. Density functional theory (DFT) calculations and X-ray crystallographic analysis of the isolated hypaphorine was determined. The antibacterial effects of hypaphorine against a number of Gram positive and Gram negative bacterial strains were investigated. The root mean square deviation between the experimental and calculated bond lengths and bond angles of hypaphorine were found to be 0.046 Å and 1.5° respectively. The highest occupied molecular orbital (HOMO) of hypaphorine was delocalised on the indole moiety whereas the lowest occupied molecular orbital (LUMO) was delocalised on the -N(CH 3 ) 3 group and the HOMO-LUMO gap of hypaphorine was 4.65 eV. Hypaphorine inhibited the growth of the Gram-positive bacteria tested, namely Bacillus cereus, B. subtilis, Staphylococcus aureus and S. epidermidis. The lowest minimum inhibitory concentration (MIC) value of 2 mg/mL was exhibited against Mycobacterium smegmatis, Staphylococcus aureus and B. subtilis. The theoretical and experimental results from this study showed that hypaphorine is capable of forming quadrupole moments thus explaining its antibacterial effects on Gram positive bacteria. Graphic abstractroot hair formation and stimulates curling of the roots which aids in these symbiotic relationships [7]. Hypaphorine has thus been detected in a number of ectomycorrhizal fungal species like Pisolithus tinctorius [1,11,12]. In these symbiotic relationships, hypaphorine inhibits the effect of IAA in the fungi by blocking membrane-bound IAA receptors thus inducing abnormal proliferation of hyphae that extend intracellularly into plant tissues.

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Section: Computational Methodologymentioning

confidence: 99%

“…Stem bark of E. addisoniae and E. mildbraedii were collected from trees in Yaounde (Centre region of Cameroon) and Buea (South West region of Cameroon) that had been used previously [16,17]. The stem barks were identified and compared to existing voucher specimens of E. addisoniae (No.…”

Section: Materials and Bacterial Strainsmentioning

confidence: 99%

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

et al. 2020

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“…The most popular method used for extraction of isoflavonoids is maceration with either MeOH or EtOH containing various percentages of H 2 O at room temperature followed by liquid-liquid Flavonoids -From Biosynthesis to Human Health fractionation using solvents with different polarities [6,10,[19][20][21][22][23][24][25][26][27][28][29][30][31][32]. Another method of extraction used MeOH or EtOH under reflux or in soxhlet apparatus [5,[33][34][35][36].…”

Section: Extraction and Purificationmentioning

confidence: 99%

Isoflavonoids

Foudah¹,

Abdel-Kader²

2017

Flavonoids - From Biosynthesis to Human Health

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Isoflavonoids are interesting class of natural products due to their positive effects on human health. Isoflavonoids include isoflavones, isoflavanones, isoflavans, rotenoids and pterocarpans. Although they are reported from many plant families, most isoflavonoids are produced by the subfamily Papilionaceae of the Fabaceae. Various chromatographic methods have been applied for the purification of isoflavonoids. Simple Ultra Violet (UV) absorption spectra as well as both One and two dimensional NMR (1D-and 2D-NMR) are critical for the identification of isoflavonoids. Each class of isoflavonoids has its unique feature in both 1 H-and 13 C-NMR that enable their proper characterization. High Resolution Mass Spectrometry (HRMS) is a substantial tool in such challenge. In vitro experiments indicated that isoflavonoids possess antioxidant, antimutagenic, antiproliferative as well as cancer preventive effects. Epidemiological studies provide support for some of these effects on human. Members of this class also are reported to have antimicrobial activity. In this chapter, isoflavones, isoflavanones, isoflavans, homoisoflavonoids and isoflavenes will be discussed in relation to their occurrence, methods of purification, spectral characters helpful in structure elucidation as well as their biological importance.

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“…8,9 Prenylated stilbenoids and isoflavanoids from the root bark of Erythrina species have also been reported to possess inhibitory activities against neuraminidases from influenza viruses and have shown activities against breast cancer lines and a commercially available protein tyrosine phosphatase 1B. [10][11][12] We now describe the isolation and structure elucidation of three new and three known prenylated flavanones and their cytotoxic activities against H4IIE hepatoma cells.…”

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Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

et al. 2015

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Extracts of Erythrina addisoniae are frequently used in the traditional medicine of Western Africa, but only insufficient information about active compounds is available. From the stem bark of Erythrina addisoniae, three new (1, 2, 4) and three known (3, 5, 6) flavanones were isolated: addisoniaflavanones I and II, containing either a 2´´,3´´-epoxyprenyl moiety (1) or a 2´´,3´´-dihydroxyprenyl moiety (2) were shown to be highly toxic (MTT-assay: EC 50 -values of 5.25 +/-13.5 and 8.5 +/-15.2 µM, respectively) against H4IIE hepatoma cells. The cytotoxic potential of the other isolated flavanones was weaker (range of EC 50 -values between 15 and >100 µM). Toxic effects of addisoniaflavanone I and II were detectable after 3 h (MTT assay). Both compounds induced an apoptotic cell death (caspase 3/7 activation, nuclear fragmentation) in the hepatoma cells and, at high concentrations, also necrosis (membrane disruption: ethidium bromide staining), Formation of DNA strand breaks was not detectable after incubation with these compounds (comet assay). In conclusion, the new prenylated flavanones addisoniaflavanones I and II may be of interest for pharmacological purposes (e.g. potential use as cytostatic drugs) due to their high cytotoxic and pro-apoptotic potential.

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New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae

Cited by 43 publications

References 20 publications

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

Isoflavonoids

Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

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