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

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...

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Main Authors: Fan Sun, Jingya Ruan, Wei Zhao, Ying Zhang, Guilin Xiang, Jiejing Yan, Mimi Hao, Lijie Wu, Yi Zhang, Tao Wang
Format: Article
Language:English
Published: MDPI AG 2019-12-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/1/139
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spelling doaj-a58895501a1541b1a5c213e2dc850de72020-11-25T02:56:45ZengMDPI AGMolecules1420-30492019-12-0125113910.3390/molecules25010139molecules25010139New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory ActivitiesFan Sun0Jingya Ruan1Wei Zhao2Ying Zhang3Guilin Xiang4Jiejing Yan5Mimi Hao6Lijie Wu7Yi Zhang8Tao Wang9Tianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaTianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaTianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaInstitute of TCM, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaWenshanMiaoxiangSanqi Limited Company, South KaihuaRoad, Wenshan 663000, ChinaInstitute of TCM, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaInstitute of TCM, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaTianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaTianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaTianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaInflammation 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 <i>Panax notoginseng</i>. 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<sub>1</sub>&#8722;NL-A<sub>4</sub> (<b>1</b>&#8722;<b>4</b>), NL-B<sub>1</sub>&#8722;NL-B<sub>3</sub> (<b>5</b>&#8722;<b>7</b>), NL-C<sub>1</sub>&#8722;NL-C<sub>3</sub> (<b>8</b>&#8722;<b>10</b>), and NL-D (<b>11</b>) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds <b>4</b> and <b>11</b> 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 <b>1</b>, <b>2</b>, <b>5</b>, <b>6</b>, and <b>8</b>&#8722;<b>10</b> were found to play an important role in suppressing NO levels at 50 &#956;M, without cytotoxicity. All inhibitory activities were found to be dose-dependent.https://www.mdpi.com/1420-3049/25/1/139<i>panax notoginseng</i> leavesdammarane-type triterpenoid saponinsnotoginsenosides nlraw 246.7 cellanti-inflammatory activity
collection DOAJ
language English
format Article
sources DOAJ
author Fan Sun
Jingya Ruan
Wei Zhao
Ying Zhang
Guilin Xiang
Jiejing Yan
Mimi Hao
Lijie Wu
Yi Zhang
Tao Wang
spellingShingle Fan Sun
Jingya Ruan
Wei Zhao
Ying Zhang
Guilin Xiang
Jiejing Yan
Mimi Hao
Lijie Wu
Yi Zhang
Tao Wang
New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory Activities
Molecules
<i>panax notoginseng</i> leaves
dammarane-type triterpenoid saponins
notoginsenosides nl
raw 246.7 cell
anti-inflammatory activity
author_facet Fan Sun
Jingya Ruan
Wei Zhao
Ying Zhang
Guilin Xiang
Jiejing Yan
Mimi Hao
Lijie Wu
Yi Zhang
Tao Wang
author_sort Fan Sun
title New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory Activities
title_short New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory Activities
title_full New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory Activities
title_fullStr New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory Activities
title_full_unstemmed New Dammarane-Type Triterpenoid Saponins from <i>Panax notoginseng</i> Leaves and Their Nitric Oxide Inhibitory Activities
title_sort new dammarane-type triterpenoid saponins from <i>panax notoginseng</i> leaves and their nitric oxide inhibitory activities
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-12-01
description 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 <i>Panax notoginseng</i>. 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<sub>1</sub>&#8722;NL-A<sub>4</sub> (<b>1</b>&#8722;<b>4</b>), NL-B<sub>1</sub>&#8722;NL-B<sub>3</sub> (<b>5</b>&#8722;<b>7</b>), NL-C<sub>1</sub>&#8722;NL-C<sub>3</sub> (<b>8</b>&#8722;<b>10</b>), and NL-D (<b>11</b>) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds <b>4</b> and <b>11</b> 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 <b>1</b>, <b>2</b>, <b>5</b>, <b>6</b>, and <b>8</b>&#8722;<b>10</b> were found to play an important role in suppressing NO levels at 50 &#956;M, without cytotoxicity. All inhibitory activities were found to be dose-dependent.
topic <i>panax notoginseng</i> leaves
dammarane-type triterpenoid saponins
notoginsenosides nl
raw 246.7 cell
anti-inflammatory activity
url https://www.mdpi.com/1420-3049/25/1/139
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