Characterization of Antiproliferative Activity Constituents from Artocarpus heterophyllus

Abstract

Artocarpus heterophyllus is an evergreen fruit tree cultivated in many tropical regions. Previous studies have shown that some of its compositions exhibited potential tyrosinase inhibition activities. This study indentified 8 new phenolic compounds, artoheterophyllins E-J (1-6), 4-geranyl-2',3,4',5-tetrahydroxy-cis-stilbene (7), and 5-methoxymorican M (8) and 2 new natural compounds (9 and 10), 2,3-dihydro-5,7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl)-4H-benzopyran-4-one and 6-[(1S,2S)-1,2-dihydroxy-3-methylbutyl]-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one, together with 23 known compounds (11-33), from the ethanol extract of the wood of A. heterophyllus. The structures of the eight new compounds (1-8) and two new natural compounds were established by extensive 1D- and 2D-NMR experiments. The anticancer effects of the isolated compounds were examined in MCF-7, H460, and SMMC-7721 human cancer cell lines by MTT assay. Compounds 5, 11, 12, and 30 significantly reduced the cell viabilities of these cell lines. Especially, compounds 11 and 30 resulted in more potent cytotoxicity than the positive control, 5-fluorouracil (5-Fu), in SMMC-7721 cell line, with IC50 values of 15.85 and 12.06 μM, whereas compound 30 exhibited more potent cytotoxicity than 5-Fu in NCI-H460 cell line, with an IC50 value of 5.19 μM. In addition, this study suggests that compounds 11 and 30 from the wood of A. heterophyllus have anticancer potential via MAPK pathways.

Structure elucidation and NMR assignments of two new flavanones from the roots of Artocarpus heterophyllus

“…The IR and UV data indicated that 2 possessed flavanone skeleton. The 1 H-NMR spectrum of 2 was very similar to that of the known compound 3, [2] and a comparison of those of 2 and 3 showed the signals of the following protons: an aromatic ABX spin system at δ 7. C NMR spectrum of 2, the chemical shift values of all the carbon atoms except that of C-6 were similar to those of the relevant carbon atoms of 3.…”

“…[2,6] The anti-respiratory burst activities of the four isolated compounds 1-4 were biologically evaluated by determining luminol-dependent chemiluminescence in rat PMNs. All of these compounds exhibited significantly suppressive activity on respiratory burst of rat PMNs.…”

“…In South China, A. heterophyllus is popularly cultivated for its edible fruits, while its root has been used as a folk medicine for subdhing swelling and detoxicating. [1] Previous work on this plant reported a series of flavonoids and 2-arylbenzofurons, which possessed various biological activities including cytotoxicity, [2] tyrosinase inhibitory, [3] antiinflammatory [4] and antioxidant effects, [5] and so on. The present phytochemical investigation on the roots of A. heterophyllus led to the isolation of two new flavanones, artoheterones A and B (1 and 2), as well as two known ones, 2,3-dihydro-5,7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one (3) [2] and artocarpanone (4) [6] (Fig.…”

Prenylflavonoids from the Twigs of <i>Artocarpus nigrifolius</i>

“…[2][3][4] Previous phytochemical research on plants of this genus led to diverse prenylated flavonoids and stilbenoids with interesting biological activities such as cytotoxic, [5][6][7][8][9][10] antiinflammatory, [11][12][13][14][15] antioxidant, 16,17) antimalarial, 18,19) and antifungal activities, 20) as well as tyrosinase inhibitory activities 21,22) and 5α-reductase inhibitory activities. 23) As part of our ongoing efforts to discover novel potential anticancer leads from Moraceous plants, 24) two new prenylated flavones (2, 12) along with 13 known compounds (1, 3-11, 13-15) have been isolated from the twigs of Artocarpus nigrifolius C. Y. WU for the first time.…”

Inhibition of Hepatocarcinogenesis by ArtinM via Anti-proliferative and Pro-apoptotic Mechanisms

“…Recently, extracts isolated from Artocarpus heterophyllus (jackfruit) reported to show anti-proliferative properties on human cancer cell lines and murine B-cell lymphoma (11,12). ArtinM is a d-mannose-binding lectin found in the seeds of Artocarpus heterophyllus that interacts with N-glycans and is associated with receptors on the surface of phagocytic cells to induce production of inflammatory mediators, such as tumor necrosis factor alpha (TNFα) (13), interleukin 12 (IL12) and interferon gamma (IFNγ) (14).…”