Markhasphingolipid A, new phytosphingolipid from the leaves of Markhamia stipulata var. canaense V.S. Dang

Abstract

Markhasphingolipid A, new phytosphingolipid from the leaves of Markhamia stipulata var. canaense V.S. Dang From the leaves of Markhamia stipulata var. canaense V.S. Dang, one new phytosphingolipid, named markhasphingolipid A (6), together with five known compounds, 4',7-O-dimethylapigenin (1), narigenin (2), tectoquinone (3), mollic acid (4), 1-hexadecanoyl-sn-glycerol (5) were classified by various chromatographic methods. Their structures were designated by IR, UV, HR-ESI-MS, HR-ESI-MS/MS and NMR experiments. All compounds were recognized for the first time from this species. The cytotoxicity of all n-hexane fractions and isolated compounds (5 & 6) against three human cancer cell lines (HeLa, HepG2, and MCF-7) were evaluated by SRB assay. All n-hexane fractions expressed cytotoxic effect on three tested cancer cell lines (at the concentration of 100 μg/mL, percent of cytotoxicity ranged from 55.81 to 95.83%) as well as compound 5 (IC 50 ranged from 48.51 to 63.30 μM) whereas fraction H.I and compound 6 did not show activity.

Sphingolipid metabolism, transport, and functions in plants: Recent progress and future perspectives

“…A high-performance liquid chromatography (HPLC) analysis identified the major plant C18 LCBs, including t18:1(Z), t18:1(E), t18:0, d18:1(Z), d18:1(E), and d18:0 ( Chen et al., 2006 ). Plants also contain traces of another four C18 LCBs (d18:2(4E,8E), d18:2 (4E,8Z), t18:2 [with unknown structure], and a unique d18:1 [with a C10=C11 double bond]), one C20 LCB t20:0, and special d21:1 or d22:1 LCBs (the last two LCBs contain a C7=C8 double bond), which have been validated by either mass spectrometry (MS) or nuclear magnetic resonance (NMR) ( Kimberlin et al., 2013 ; Ngo et al., 2020 ; Panzenboeck et al., 2020 ; Wang et al., 2020a ). However, the two common LCBs d20:0 and d20:1, which are detected in animals and Saccharomyces cerevisiae , are rarely reported in plant samples ( De Castro Levatti et al., 2017 ; Zhu et al., 2020 ).…”

“…t18:0 and t18:1 with hydroxy and non-hydroxy fatty acyl chains N. tabacum Kimberlin et al. 2013 additionally distinguished 40 t20:0-based sphingolipids: t20:0-based Cers, hCers, GlcCers and GIPC A. thaliana LC-ESI-MS/MS Cacas et al., 2013 distinguished GIPCs with different head groups in different plants: Hex-IPC; Hex(R1)-HexA-IPC; Hex-Hex(R1)-HexA-IPC Hex-(HexA) 3 -IPC; (HexA) 4 -IPC; PenHexHex(R1)-HexA-IPC (Hex) 2 Hex(R1)-HexA-IPC; Pen(Hex) 2 Hex(R1)-HexA-IPC (Pen) 2 HexHex(R1)-HexA-IPC; Pen(Hex) 3 Hex(R1)-HexA-IPC (Pen) 2 (Hex) 2 Hex(R1)-HexA-IPC; (Pen) 3 HexHex(R1)-HexA-IPC (Pen) 4 HexHex(R1)-HexA-IPC 23 plant species MALDI-Q-TOF-MS and ESI-MS/MS Tarazona et al., 2015 detected sphingolipids together with other lipids via an enhanced multiplexed LC-MS platform for broad and in-depth analysis of plant lipids: 31 ceramide species; 24 hexosylceramide species 36 GIPC species A. thaliana UPLC-MS Fang et al., 2016 detected different monosaccharide compositions of GIPC headgroups, including Ara, GlcN, Gal, Glc, Man, and GlcA A. thaliana LC-MS/MS and HPAEC-PAD Cacas et al., 2016 detected sphingolipids with odd number fatty acyl chains A. thaliana and N. tabacum GC-MS detected different monosaccharide compositions of GIPC headgroups MALDI-TOF-MS Ishikawa et al., 2018 detected 166 sphingolipids with d18:0, d18:1, d18:2, t18:0, t18:1 LCBs A. thaliana LC-MS/MS detected 100 sphingolipids (containing odd number fatty acyl chains) Oryza sativa Wang et al., 2020a Identified a new glycosylsphingolipid with odd number LCBs and fatty acyl chain Psychotria serpens NMR and MS (LC-MS, and GC-MS) Ngo et al., 2020 Identified the new phytosphingolipid markhasphingolipid A Markhamia stipulata var . canaense V.S.…”