New Dammarane-Type Triterpenoid Saponins from Panax notoginseng Leaves and Their Nitric Oxide Inhibitory Activities

Abstract

Inflammation is a very common and important pathological process that can cause many diseases. The discovery of anti-inflammatory drugs and the treatment of inflammation are particularly essential. Dammarane-type triterpenoid saponins (PNS) were demonstrated to show anti-inflammatory effects in the leaves of Panax notoginseng. Chromatographies and spectral analysis methods were combined to isolate and identify PNS. Moreover, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, eleven new dammarane-type triterpenoid saponins, notoginsenosides NL-A 1 -NL-A 4 (1-4), NL-B 1 -NL-B 3 (5-7), NL-C 1 -NL-C 3 (8-10), and NL-D (11) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds 4 and 11 were characterized by the malonyl substitution at 3-position. The 3-malonyl substituted dammarane-type terpennoids were first obtained from natural products. In addition, compounds 1, 2, 5, 6, and 8-10 were found to play an important role in suppressing NO levels at 50 µM, without cytotoxicity. All inhibitory activities were found to be dose-dependent.

New 12,23-Epoxydammarane Type Saponins Obtained from Panax notoginseng Leaves and Their Anti-Inflammatory Activity

“…Different from our previous research [ 7 , 8 ], a new 12,23-epoxydammarane skeleton has been found in this paper, and its superior in vitro anti-inflammatory activites, compared with the other compounds reported earlier [ 7 , 8 ], made it more promising to become the target of new anti-inflammatory drugs. What is more, the results of the Western blot assays provided more evidence for its further development.…”

“…Moreover, the planar structure of 1 was determined by the long-range correlations displayed from H 3 -18 to C-7–9, C-14; H 3 -19 to C-1, C-5, C-9, C-10; H 3 -21 to C-17, C-20, C-22; H 3 -23 to C-12, C-24, C-25; H 3 -26 to C-24, C-25, C-27; H 3 -27 to C-24–26; H 3 -28 to C-3–5, C-29; H 3 -29 to C-3–5, C-28; H 3 -30 to C-8, C-13–15; H-1′ to C-3; H-1″ to C-20; H-1‴ to C-6″ in its HMBC experiment ( Figure 2 ). The chemical shifts of protons and carbons in A and B rings resembled notoginsenoside NL-A 1 [ 7 ], which suggested that the A and B rings of notoginsenoside NL-I ( 1 ) were identical to it. Moreover, the NOE correlations observed between δ H 1.49 (H-9) and δ H 3.67 (H-12); δ H 3.67 (H-12) and δ H 3.22 (H-17), 4.86 (H-23); δ H 3.22 (H-17) and δ H 4.86 (H-23) in the NOESY spectrum ( Figure 2 ) indicated that H-12 and H-23 were α-orientation, like H-9, while the β-orientations of H-13 and 21-CH 3 were confirmed by the cross peaks observed between δ H 1.59 (H-13) and δ H 0.94 (H 3 -18), 1.51 (H 3 -21).…”

“…Owing to the gradual scarcity of its resources, the other parts of P. notoginseng have gradually become a research hotspot in recent years. In a previous study, we found that the dammarane triterpenoid saponins in P. notoginseng leaves had an excellent inhibitory effect on the production of nitric oxide from LPS-activated RAW 264.7 cells [ 7 , 8 ].…”

Panax notoginseng saponins improves healing of high glucose‐induced wound through the GSK‐3β/β‐catenin pathway

“…16 Dammarane-type triterpenoid saponins could inhibit NO activities in a dose-dependent manner. 17 Treatment of porcine circovirus 2-infected porcine lung cells with PNS resulted in a significant reduction in intracellular NO content and xanthine oxidase activity, which suggested that PNS could regulate the oxidative stress of immune cells. 18 PNS decreased serum MDA, lactate dehydrogenase, myocardial tissue superoxide dismutase, and reactive oxygen species.…”

Herbal Active Ingredients: Potential for the Prevention and Treatment of Acute Lung Injury

“…By summarizing the structure-activity relationship of saponins, the anti-inflammatory activities of the compounds were found to be closely related to the types of substituted sugar groups and to increase with the number of substituted sugar groups. In addition, the positions and number of hydroxyl groups on the mother nucleus have a strong influence on the anti-inflammatory activities of saponins [ 46 ].…”