Polyacetylenes from the Roots of Swietenia macrophylla King

Abstract

A phytochemical investigation of the roots of Swietenia macrophylla led to the isolation of seven polyacetylenes, including five new compounds (15) and two known ones (67). Their structures were elucidated by extensive spectroscopic analysis and detailed comparison with reported data. All the isolates were tested for their cytotoxicity against the human hepatocellular carcinoma cell line BEL-7402, human myeloid leukemia cell line K562, and human gastric carcinoma cell line SGC-7901. Compounds 1 and 6 showed moderate cytotoxicity against the above three human cancer cell lines with IC50 values ranging from 14.3 to 45.4 μM. Compound 4 displayed cytotoxicity against the K562 and SGC-7901 cancer cell lines with IC50 values of 26.2 ± 0.4 and 21.9 ± 0.3 μM, respectively.

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

“…All compounds isolated were tested for their cytotoxicity against the human hepatocellular carcinoma cell line BEL-7402, human leukemia cell line K562, and human gastric carcinoma cell line SGC-7901. Only the panaxydiol-type polyacetylenes 70 and 71 showed moderate cytotoxicity against the above three human cancer cell lines, with IC 50 values ranging from 14.3 to 45.4 µM, whereas the other panaxydiol-type polyacetylenes (chemical structures not shown) were inactive (IC 50 > 50 µM) [170]. From Toona ciliata var.…”

“…The importance of unsaturated double bonds and, in particular, a terminal double bond for the cytotoxicity of C 17 acetylenic oxylipins, as described in previous sections, was confirmed in a study on polyacetylenes isolated from the roots of Swietenia macrophylla King (Meliaceae), commonly known as mahogany. The investigation of potential cytotoxic compounds from the roots of this plant led to the isolation of several panaxydiol-type polyacetylenes that did not possess any terminal double bond [170]. All compounds isolated were tested for their cytotoxicity against the human hepatocellular carcinoma cell line BEL-7402, human leukemia cell line K562, and human gastric carcinoma cell line SGC-7901.…”

Variation on a theme: the structures and biosynthesis of specialized fatty acid natural products in plants

“…Recent reports of new polyacetylenes sometimes provide missing details or describe variants on this theme (for example, Murata et al., 2017, Figure 2). Other newly reported molecules are relatively extreme examples within these general structural constraints, such as compounds with four or more carbon–carbon double or triple bonds (for example, Appendino et al., 2009; Liu et al., 2018, Figure 2) or highly acetylated compounds (for example, Mi et al., 2019; Figure 2).…”

“…In addition to heterocyclic rings, polyacetylenes can also bear functional group modifications (Figure 2, green ovals). These can include, for example, acetylation (structures reported by, e.g., Chen et al., 2015; Mi et al., 2019; Figure 2) and glycosylation (structures from, e.g., Guo et al., 2017; Pollo et al., 2013; Figure 2), as well as esterification and amidation (such as structures recently reported in Althaus et al., 2017; Blagojević et al., 2017; Figure 2; reviewed in Negri, 2015). The addition of ring arrangements and functional group modifications to the repertoire of polyacetylene variability considerably increases the structural space occupied by polyacetylenes.…”