Antimutagenic action of the triterpene betulinic acid isolated from Scoparia dulcis (Scrophulariaceae)

Freitas, Perla Lopes de; Dias, Ana Carolina Soares; Moreira, Vanessa; Monteiro, Sílvio Gomes; Pereira, Silma Regina Ferreira

doi:10.4238/2015.august.19.7

Cited by 7 publications

(2 citation statements)

References 29 publications

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“…13 C NMR (100 MHz, CDCl 3 ) δ 171.0 (C-28), 150.9 (C-20), 109.4(C-30), 80.9 (C-3), 55.4 (C-17), 50.4 (C-18), 48.3 (C-5), 48.0 (C-9), 42.9 (C-19), 40.9 (C-4), 40.0 (C-8), 38.4 (C-13), 38.1 (C-1), 37.8 (C-22), 37.1 (C-10), 35.6 (C-7), 34.2 (C-14), 29.9 (C-12), 27.9 (C-12), 27.4 (C-2), 25.1 (C-15), 23.7 (C-16), 21.3 (C-23), 20.9 (C-24), 19.3 (C-29), 18.2 (C-11), 16.5 (C-25), 16.19 (C-6), 15.9 (C-26), 14.5 (C-27). This was in accordance with the data reported in the literature (de Freitas et al 2015).…”

Section: Betulinic Acid (10)supporting

confidence: 94%

X anthium Orientale subsp. Italicum (Moretti) Greuter: bioassay-guided isolation and its chemical basis of antitumor cytotoxicity

Lei

Yang

et al. 2019

Natural Product Research

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Inspired by the allelopathetic effects of Xanthium orientale subsp. italicum (Moretti) Greuter, bioassay-guided isolation was employed to identify its antitumor constitutes and clarify the chemical basis of its multitarget activity. Among four fractions of X. orientale extraction, TCM-fr and PE-fr were discovered to exhibit significant cytotoxicity aganist HepG 2 and A549 cells, which were further isolated by chromatographic methods to yield 16 compounds, including 6 active ones: xanthatin (1), xanthinosin (2), lupeol (6), oleanolic acid (9), betulinic acid (10) and emodin ( 12) with IC 50 of 10~120μM. The systematically study of antitumor constitutes has firstly provided a chemical basis for the multitarget and synergistic anticancer activity of the genus Xanthium. The method presented could be utilized to guide the exploitation and promising utilization of X. orientale on cancer therapy.

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Section: Betulinic Acid (10)supporting

confidence: 94%

X anthium Orientale subsp. Italicum (Moretti) Greuter: bioassay-guided isolation and its chemical basis of antitumor cytotoxicity

Lei

Yang

et al. 2019

Natural Product Research

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“…Indeed, the parent triterpenoid ursolic acid decreased H 2 O 2 ‐induced DNA damage in the colonic cell line Caco‐2 by a similar extent (>40%) to that of TRF and CDDO, albeit at 50‐fold higher concentration of 5 μM . Triterpenoids from R. rosifolius fruits have previously been shown to have beneficial effects against human colon cancer cells and triterpenoids from Scoparia dulcis roots exerted antimutagenic activity using the in vivo SMART assay . To our knowledge, this study is the first to demonstrate DNA damage reduction and the modulation of Nrf2/ARE pathway by triterpenoids (both CDDO and TRF) in the normal cell line CCD841‐CoN.…”

Section: Discussionmentioning

confidence: 62%

Novel colon‐available triterpenoids identified in raspberry fruits exhibit antigenotoxic activities in vitro

McDougall

Allwood

Pereira-Caro

et al. 2016

Molecular Nutrition Food Res

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Abbreviations: CDDO = 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid; FAV = fruit and vegetables; GI = gastrointestinal; TRF = triterpenoid-rich fraction;Key words: Raspberries, metabolic profiling, triterpenoids, colon cancer, ileal fluid ABSTRACT Scope: Ileostomy studies provide a unique insight into digestion of food, allowing identification of physiologically relevant dietary phytochemicals and their metabolites important to gut health. We previously reported the consistent increase of components in ileal fluids of ileostomates after consumption of raspberries with use of non-targeted LC-MS n techniques and data deconvolution software highlighting two major unknown components (m/z 355 and 679). Methods and results:In-depth LC-MS n analyses suggested that the ileal m/z 355 components were p-coumaroyl glucarates. These compounds have not been identified previously and were confirmed in raspberry extracts after partial purification. The major ileal component with m/z 679 was a glycoside with an aglycone of m/z 517 and was present as two peaks in extracts of whole puree, unseeded puree and isolated seeds. These components were purified using Sephadex LH20 and C18 SPE units and identified as major, novel raspberry triterpenoid glycosides. This triterpenoid-enriched fraction (100 nM)protected against H 2 O 2 -induced DNA damage in both colon cancer and normal cell lines and altered expression of cytoprotective genes. Conclusion:The presence of these novel raspberry triterpenoid components in ileal fluids indicates that they would be colon-available in vivo, so confirmation of their anti-cancer bioactivities is of key physiological relevance.www.mnf-journal.comThis article is protected by copyright. All rights reserved.Two major unknown components present in ileal fluids after intake of raspberries were identified as triterpenoid glycosides and p-coumaroyl glucarates using LC-MS n analysis. The triterpenoids were purified from raspberries and were shown to have genoprotective effects at sub-micromolar levels against H 2 O 2 -induced damage in colon cell lines. Therefore these novel triterpenoids combine established colonic bioavailability with potential bioactivity at physiological doses. INTRODUCTIONThere is great interest in the possibility that non-nutritive components could directly contribute to the health benefits attributable to a diet rich in fruit and vegetables (FAV) [1][2][3].One set of phytochemicals of specific interest are the (poly)phenols as are found in high concentrations in certain beverages and FAV, such as berries, and have been attributed a range of important bioactivities [4][5][6][7][8][9]. However, an important issue with ascribing any potential health benefit is the long held view that the bioavailability of many (poly)phenol classes is low. For example, urinary recoveries of anthocyanins, which reflect passage through the circulatory system, are typically <<1% of intake [10], although recent studies with Although previous targeted liquid chromatography mass spectrometry (LC-MS n ) analyses[...

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Maternal Health in Central America: The Role of Medicinal Plants in the Pregnancy-Related Health and Well-Being of Indigenous Women in Central America

Locklear

Mahady

Michel

et al. 2018

Global Maternal and Child Health

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Antimutagenic action of the triterpene betulinic acid isolated from Scoparia dulcis (Scrophulariaceae)

Cited by 7 publications

References 29 publications

X anthium Orientale subsp. Italicum (Moretti) Greuter: bioassay-guided isolation and its chemical basis of antitumor cytotoxicity

X anthium Orientale subsp. Italicum (Moretti) Greuter: bioassay-guided isolation and its chemical basis of antitumor cytotoxicity

Novel colon‐available triterpenoids identified in raspberry fruits exhibit antigenotoxic activities in vitro

Maternal Health in Central America: The Role of Medicinal Plants in the Pregnancy-Related Health and Well-Being of Indigenous Women in Central America

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