Goniolanceolatins A–H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus

Abstract

Eight new bis-styryllactones, goniolanceolatins A−H (1−8), possessing a rare α,β-unsaturated δ-lactone moiety with a (6S)-configuration, were isolated from the CH 2 Cl 2 extract of the stembark and roots of Goniothalamus lanceolatus Miq., a plant endemic to Malaysia. Absolute structures were established through extensive 1D-and 2D-NMR data analysis, in combination with electronic dichroism (ECD) data. All of the isolates were evaluated for their cytotoxicity against human lung and colorectal cancer cell lines. Compounds 2 and 4 showed cytotoxicity, with IC 50 values ranging from 2.3 to 4.2 μM, and were inactive toward human noncancerous lung and colorectal cells. Compounds 1, 3, 6, 7, and 8 showed moderate to weak cytotoxicity. Docking studies of compounds 2 and 4 showed that they bind with EGFR tyrosine kinase and cyclin-dependent kinase 2 through hydrogen bonding interactions with the important amino acids, including Lys721,

Dereplication of a Dichloromethane Extract of Goniothalamus lanceolatus Leaves using UHPLC-ESI-ORBITRAP HRMS

“…Higher confidence in annotation was achieved by comparison with seven reference standards (Level 1). These standards were the styryl-lactones (Figure 2) isolated by our team from the barks and roots part of G. lanceolatus (Rasol et al 2018;Bihud et al 2019). The structural elucidations of these standards were confirmed from their MS/MS, UV and NMR data.…”

“…We used the biological source keyword Goniothalamus (genus) and this yielded 197 compounds. To supplement this database, an in-house library generated from the previously isolated 24 compounds of G. lanceolatus (roots and barks extracts) was added (Rasol et al, 2018;Bihud et al, 2019). All the isolated reference compounds had not yet been reported in the Goniothalamus database generated from DNP.…”

“…In our previous study, we focused on the isolation of secondary metabolites from G. lanceolatus extracts for cytotoxicity and anti-cancer properties. This study reports the presence of styryl-lactones, acetogenins, and alkaloid derivatives (Rasol et al, 2018;Bihud et al, 2019). There is no published data available to date on the possible anti-dengue activity of G. lanceolatus.…”

Synthesis and crystal structure of (±)-Goniotamirenone C

“…Many species of Goniothalamus have been used as folk medicines for the treatment of common illnesses and as a tonic. Goniothalamus is well known as a rich source of styryllactones, with over 100 compounds isolated and identified (Meesakul et al, 2020;Jaidee et al, 2019, Bihud et al, 2019. However, chlorinated styryllactones are rarely reported in the Annonaceae family.…”

Goniothalamus lanceolatus extract inhibits the growth of human ovarian cancer cells through migration suppression and apoptosis induction

“…The newly discovered alkaloids of goniolanceolactam and 2-acetyl-3-amino-1,4naphthoquinone isolated from the dichloromethane (DCM) root extract were reported to have a cytotoxic effect on human colon and lung cancer cells (Rasol et al, 2018a). Moreover, eight new bis-styryllactones and goniolanceolatins A−H, and four known styryllactones with a rare (6S)-styrylpyrone and (1S)pyranopyrone moieties were also isolated from the GL (Bihud et al, 2019). These compounds have been reported to be associated with antimalarial properties against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum (Kaharudin et al, 2020).…”