2013
DOI: 10.1021/np300893n
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Cytotoxicity and Modulation of Cancer-Related Signaling by (Z)- and (E)-3,4,3′,5′-Tetramethoxystilbene Isolated from Eugenia rigida

Abstract: Bioassay-guided fractionation of the leaves of Eugenia rigida yielded three stilbenes, (Z)-3,4,3',5'-tetramethoxystilbene (1), (E)-3,4,3',5'-tetramethoxystilbene (2), and (E)-3,5,4'-trimethoxystilbene (3). Their structures were determined using 1D- and 2D-NMR spectroscopy and HRESIMS. The sterically hindered Z-stereoisomer 1, a new natural product, was prepared by time-dependent photoisomerization of the E-isomer (2) under UV irradiation at λ254 nm, while 2,3,5,7-tetramethoxyphenanthrene (5) was identified at … Show more

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Cited by 39 publications
(33 citation statements)
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References 24 publications
(35 reference statements)
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“…Each mixture was resolved by silica gel PLC column chromatography using a gradient of EtOAc- n -hexane to separate the Z product from the residual E isomer. Spectral data of compounds 5 - 8 are in perfect agreement with those reported in the literature (35-37). …”
Section: Methodssupporting
confidence: 88%
“…Each mixture was resolved by silica gel PLC column chromatography using a gradient of EtOAc- n -hexane to separate the Z product from the residual E isomer. Spectral data of compounds 5 - 8 are in perfect agreement with those reported in the literature (35-37). …”
Section: Methodssupporting
confidence: 88%
“…This plant, present in Brazil and Argentina and distributed in the Caribbean islands, has been used traditionally for the treatment of leukaemias. Earlier investigation of E. rigida exhibited ( E )- and ( Z )-3,4,3′,5′-tetramethoxystilbenes and 4,3′,5′-trimethoxyresveratrol with cytotoxic and cancer-related signal-modulating activities [ 26 ]. The crude ethanolic extract was inactive in the initial screens against P. falciparum , but the AHTS-derived COMBI 79575-c5 had potent activity against 3D7 and K1 strains, with respective EC 50 values of 0.6 and 0.19 µg/mL; other COMBIs were inactive.…”
Section: Resultsmentioning
confidence: 99%
“…Although we previously reported the synthesis of TMS and TMF hybrid analogs and their growth inhibitory effects on various cancer cells [16], only percent growth inhibition values were determined. In this study, we examined the mechanism involved in the cytotoxicity of hybrid TMS-TMF compounds in human cervical carcinoma cells.…”
Section: Discussionmentioning
confidence: 99%
“…The molecular hybridization of anti-cancer agents is an effective strategy to generate novel ligands with improved anti-cancer activity relative to the parent molecules [13][14][15][16]. By adopting this strategy, we recently reported the synthesis of natural product hybrids that could induce potential anti-proliferative activity [16].…”
Section: Introductionmentioning
confidence: 99%
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