Abstract
Four new protopanaxatriol-type triterpenes (1–2) and glucosides (3–4), were isolated from the rot roots of Panax notoginseng (Burk.) Chen, along with four known ones (5–8). Their structures were elucidated on the basis of extensive spectroscopic analysis (HRESIMS, NMR, UV, IR, and OR) and acidic hydrolysis. The possible transformation pathway of these compounds were also speculated from ginsenoside Rg1. Compound 1, with a unique α,β-unsaturated ketene in its side chain, showed significant inhibitory effects against NO production on Murine macrophage cells (IC50 = 4.12 ± 0.20 μM) and comparable cytotoxicities against five human cancer cell lines (myeloid leukemia HL-60, lung cancer A-549 cells, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480) to positive control, cisplatin (DDP).Graphical
Highlights
Panax notoginseng (Burk.) Chen (Araliaceae), a well-known member called Sanqi or Tianqi in Ginseng family for the treatment of cardiovascular diseases, has been domesticated and cultivated for more than 400 years in the southwest of China [1]
Previous HPLC-HRMS study revealed that the oxidation levels of constituents in roots of P. notoginseng are significantly increased after being infected by root rot diseases [7]
This led to the identification of four new (1–4) and four known (5–8) triterpenes and saponins (Fig. 1), and their possible transformation pathway were speculated in this paper
Summary
The air-dried rot roots of P. notoginseng were crushed into small grains and extracted with MeOH. The NMR data of 1 were similar to those of 20(S)-protopanaxatriol (PPT) [8], except for an additional ketone (δC 203.2), the shielding of C-25 (δC 145.2 vs δC 150.4 in PPT), and the appearance of a terminal vinyl at C-25 (δC 124.9) This indicated 1 to be a PPT-type triterpene with an α,β-unsaturated ketone (C-24) on the side chain. The 1H-NMR spectrum of 3 showed an anomeric proton signal of the β-d-glucopyranosyl moiety at δH 5.26 (d, J = 7.7 Hz), an active hydrogen at δH 14.37 (s) and two olefinic protons in a disubstituted E-double bond at δH 6.08 (d, J = 15.7 Hz) and δH 6.21 (m). At primary concentration of 50 μM for NO inhibition and 40 μM for cytotoxicity, the other compounds 2–8 displayed no obvious anti-inflammatory and cytotoxic activities
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