Dammarane-type saponins from the leaves of Panax notoginseng and their neuroprotective effects on damaged SH-SY5Y cells

Liu, Xin-Yi; Wang, Shan; Li, Chuang‐Jun; Ma, Jie; Chen, Fang-You; Peng, Ying; Wang, Xiaoliang; Zhang, Dongming

doi:10.1016/j.phytochem.2017.09.020

Cited by 36 publications

(18 citation statements)

References 15 publications

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“…Among them, 1-10 were PPD-type saponins. It was suggested that PPD derivatives were the major PNS in P. notoginseng leaves, which was in accordance with the results found by other researchers [6][7][8][9]. As PPTs were reported to be the main PNS in P. notoginseng roots [17], we could not draw the conclusion that P. notoginseng leaves would be a possible replacement of the roots used in clinics.…”

Section: Discussionsupporting

confidence: 66%

“…NO is implicated in a variety of inflammatory conditions, which indicates the agents block NO production might be beneficial for the treatment of inflammatory responses. In this study, pretreatment of notoginsenosides NL-A 1 (1), NL-A 2 (2), NL-B 1 (5), NL-B 2 (6), NL-C 1 -NL-C 3 (8)(9)(10) at noncytotoxic concentration (50 µM) decreased the NO production significantly, which indicated that they have an anti-inflammatory activity. Moreover, the inhibitory effects of all of them were found to be dose-dependent.…”

Section: Discussionmentioning

confidence: 54%

“…The cross peaks from δ H 1.57 (H 3 -26) to δ C 30.6 (C-27), 70.0 (C-25), 142.2 (C-24); δ H 1.56 (H 3 -27) to δ C 30.7 (C-26), 70.0 (C-25), 142.2 (C-24), clarified the above-mentioned description. The NMR data of its aglycone were likable to those of the known compound, 3-O-β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-3β,12β,20(S),25 -tetrahydroxydammar-23-ene-20-O-β-d-glucopyranoside-(1→6)-β-d-glucopyranoside[6]. Thus, its aglycone was elucidated to be 3β,12β,20(S),25-tetrahydroxydammar-23-ene.…”

mentioning

confidence: 66%

“…2 (C-20); δ H 5.66 (H-1 ) to δ C 68.3 (C-6 ) displayed in its HMBC spectrum. The resonance of C-25 were shifted downfield by about 11 ppm, as compared with notoginsenoside Fh5 with 3β,12β,20(S),25-tetrahydroxydammar-23-ene as aglycone [6], indicating that C-25 of compound 1 was substituted by the hydroperoxyl group. Moreover, since the chemical shifts of notoginsenoside NL-A 1 (1) aglycone were identical to those of the known compound, 3β,12β,20S-trihydroxy-25-hydroperoxydammar-23-ene- [13], its aglycone was determined to be 3β,12β,20S-trihydroxy-25-hydroperoxydammar-23-ene.…”

mentioning

confidence: 93%

“…Thus, its aglycone was elucidated to be 3β,12β,20(S),25-tetrahydroxydammar-23-ene. Finally, the linkage positions between sugar and sugar, as well as sugar and aglycone were clarified by the long-range correlation observations from δ H 4.96 (H-1 ) to δ C 89.0 (C-3); δ H 5.18 (H-1 ) to δ C 83.3 (C-20); and δ H 5.65 (H-1 ) to δ C 68.4 (C-6 ).The molecular formula of both notoginsenosides NL-B 2(6) and NL-B 3(7) were determined to be C 58 H98 O 27 , on the basis of the MS analysis (6: m/z 1225.62134 [M − H] − , 7: m/z 1225. 61841 [M − H] − , both calcd.…”

mentioning

confidence: 97%

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

et al. 2019

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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.

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Section: Discussionsupporting

confidence: 66%

Section: Discussionmentioning

confidence: 54%

mentioning

confidence: 66%

mentioning

confidence: 93%

mentioning

confidence: 97%

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

et al. 2019

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Identification and characterization of forced degradation products and stability‐indicating assay for notoginsenosidefc by using UHPLC‐Q‐TOF‐MS and UHPLC‐MS/MS: Insights into stability profile and degradation pathways

Ma¹,

Guan²,

Ju³

et al. 2019

J of Separation Science

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Notoginsenoside Fc, a protopanaxadiol-type saponin, shows multi-pharmacological activities. Chemical stability evaluation plays a crucial role in drug development.In this study, the forced degradation behavior of Notoginsenoside Fc was investigated under hydrolytic and oxidative conditions. A specific ultra high performance liquid chromatography with quadrupole time-of-flight mass spectrometry was developed for the separation, identification, and characterization of the degradation products of Notoginsenoside Fc. Fifty potential degradation products were formed via deglycosylation, dehydration, hydration, isomerization, side-chain cleaving, oxidation, and superoxidation. Notoginsenoside Fc was subjected to different pH solutions, temperatures, and time periods to assess its stability. A sensitive ultra high performance liquid chromatography-tandem mass spectrometry was developed for the quantification of Notoginsenoside Fc, notoginsenoside ST-4, notoginsenoside Ft1, and relative quantification of notoginsenoside Ft2, 20(R)-notoginsenoside Ft2, notoginsenoside SFt3, and notoginsenoside SFt4. The assay was linear over the concentration range (R 2 > 0.997) with the lowest limit of quantification of 0.02 μg/mL for Notoginsenoside Fc, Notoginsenoside ST-4, and Notoginsenoside Ft1. The intra-day precision, inter-day precision, and accuracy of the three analytes were within accepted levels. The degradation kinetics of Notoginsenoside Fc in pH 1 and 3 solutions fits to first-and second-order kinetics, respectively. The degradation of Notoginsenoside Fc is pH-, temperature-, and time-dependent.

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Plant triterpenoid saponins: biosynthesis, in vitro production, and pharmacological relevance

Biswas

Dwivedi

2019

Protoplasma

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Dammarane-type saponins from the leaves of Panax notoginseng and their neuroprotective effects on damaged SH-SY5Y cells

Cited by 36 publications

References 15 publications

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

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

Identification and characterization of forced degradation products and stability‐indicating assay for notoginsenosidefc by using UHPLC‐Q‐TOF‐MS and UHPLC‐MS/MS: Insights into stability profile and degradation pathways

Plant triterpenoid saponins: biosynthesis, in vitro production, and pharmacological relevance

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