Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects
During a phytochemical investigation of the unripe fruits of <i>Rubus chingii</i> Hu (i.e., Fructus Rubi, a traditional Chinese medicine named “Fu-Pen-Zi”), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (<b>1</b>, &l...
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MDPI AG
2021-03-01
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| author | Jiang Wan Xiao-Juan Wang Nan Guo Xi-Ying Wu Juan Xiong Yi Zang Chun-Xiao Jiang Bing Han Jia Li Jin-Feng Hu |
| author_facet | Jiang Wan Xiao-Juan Wang Nan Guo Xi-Ying Wu Juan Xiong Yi Zang Chun-Xiao Jiang Bing Han Jia Li Jin-Feng Hu |
| author_sort | Jiang Wan |
| collection | DOAJ |
| description | During a phytochemical investigation of the unripe fruits of <i>Rubus chingii</i> Hu (i.e., Fructus Rubi, a traditional Chinese medicine named “Fu-Pen-Zi”), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (<b>1</b>, <b>2</b>, and <b>4</b>–<b>10</b>), five oleanane-type (<b>3</b>, <b>11</b>–<b>14</b>), and six cucurbitane-type (<b>15</b>–<b>20</b>) triterpenoids, together with five <i>ent</i>-kaurane-type diterpenoids (<b>21</b>–<b>25</b>). Among them, (4<i>R</i>,5<i>R</i>,8<i>R</i>,9<i>R</i>,10<i>R</i>,14<i>S</i>,17<i>S</i>,18<i>S</i>,19<i>R</i>,20<i>R</i>)-2,19α,23-trihydroxy-3-oxo-urs-1,12-dien-28-oic acid (rubusacid A, <b>1</b>), (2<i>R</i>*,4<i>S</i>*,5<i>R</i>*,8<i>R</i>*,9<i>R</i>*,10<i>R</i>*,14<i>S</i>*,17<i>S</i>*, 18<i>S</i>*,19<i>R</i>*,20<i>R</i>*)-2α,19α,24-trihydroxy-3-oxo-urs-12-en-28-oic acid (rubusacid B, <b>2</b>), (5<i>R</i>,8<i>R</i>,9<i>R</i>,10<i>R</i>, 14<i>S</i>,17<i>R</i>,18<i>S</i>,19<i>S</i>)-2,19α-dihydroxy-olean-1,12-dien-28-oic acid (rubusacid C, <b>3</b>), and (3<i>S</i>,5<i>S</i>,8<i>S</i>,9<i>R</i>, 10<i>S</i>,13<i>R</i>,16<i>R</i>)-3α,16α,17-trihydroxy-<i>ent</i>-kaur-2-one (rubusone, <b>21</b>) were previously undescribed. Their chemical structures and absolute configurations were elucidated on the basis of spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds <b>1</b> and <b>3</b> are rare naturally occurring pentacyclic triterpenoids featuring a special <i>α,β</i>-unsaturated keto-enol (diosphenol) unit in ring A. Cucurbitacin B (<b>15</b>), cucurbitacin D (<b>16</b>), and 3<i>α</i>,16<i>α</i>,20(<i>R</i>),25-tetrahydroxy-cucurbita-5,23- dien-2,11,22-trione (<b>17</b>) were found to have remarkable inhibitory effects against NF-<i>κ</i>B, with IC<sub>50</sub> values of 0.08, 0.61, and 1.60 μM, respectively. |
| first_indexed | 2024-03-10T12:48:56Z |
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| id | doaj.art-fbb89ba723ed49f6b9d78446633a9fa2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:48:56Z |
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| series | Molecules |
| spelling | doaj.art-fbb89ba723ed49f6b9d78446633a9fa22023-11-21T13:15:50ZengMDPI AGMolecules1420-30492021-03-01267191110.3390/molecules26071911Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory EffectsJiang Wan0Xiao-Juan Wang1Nan Guo2Xi-Ying Wu3Juan Xiong4Yi Zang5Chun-Xiao Jiang6Bing Han7Jia Li8Jin-Feng Hu9Minhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaMinhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaMinhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaMinhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaMinhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai 201203, ChinaInstitute of Natural Medicine and Health Products, School of Advance Study, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Taizhou 318000, ChinaMinhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai 201203, ChinaMinhang Hospital & School of Pharmacy, Fudan University, Shanghai 201199, ChinaDuring a phytochemical investigation of the unripe fruits of <i>Rubus chingii</i> Hu (i.e., Fructus Rubi, a traditional Chinese medicine named “Fu-Pen-Zi”), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (<b>1</b>, <b>2</b>, and <b>4</b>–<b>10</b>), five oleanane-type (<b>3</b>, <b>11</b>–<b>14</b>), and six cucurbitane-type (<b>15</b>–<b>20</b>) triterpenoids, together with five <i>ent</i>-kaurane-type diterpenoids (<b>21</b>–<b>25</b>). Among them, (4<i>R</i>,5<i>R</i>,8<i>R</i>,9<i>R</i>,10<i>R</i>,14<i>S</i>,17<i>S</i>,18<i>S</i>,19<i>R</i>,20<i>R</i>)-2,19α,23-trihydroxy-3-oxo-urs-1,12-dien-28-oic acid (rubusacid A, <b>1</b>), (2<i>R</i>*,4<i>S</i>*,5<i>R</i>*,8<i>R</i>*,9<i>R</i>*,10<i>R</i>*,14<i>S</i>*,17<i>S</i>*, 18<i>S</i>*,19<i>R</i>*,20<i>R</i>*)-2α,19α,24-trihydroxy-3-oxo-urs-12-en-28-oic acid (rubusacid B, <b>2</b>), (5<i>R</i>,8<i>R</i>,9<i>R</i>,10<i>R</i>, 14<i>S</i>,17<i>R</i>,18<i>S</i>,19<i>S</i>)-2,19α-dihydroxy-olean-1,12-dien-28-oic acid (rubusacid C, <b>3</b>), and (3<i>S</i>,5<i>S</i>,8<i>S</i>,9<i>R</i>, 10<i>S</i>,13<i>R</i>,16<i>R</i>)-3α,16α,17-trihydroxy-<i>ent</i>-kaur-2-one (rubusone, <b>21</b>) were previously undescribed. Their chemical structures and absolute configurations were elucidated on the basis of spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds <b>1</b> and <b>3</b> are rare naturally occurring pentacyclic triterpenoids featuring a special <i>α,β</i>-unsaturated keto-enol (diosphenol) unit in ring A. Cucurbitacin B (<b>15</b>), cucurbitacin D (<b>16</b>), and 3<i>α</i>,16<i>α</i>,20(<i>R</i>),25-tetrahydroxy-cucurbita-5,23- dien-2,11,22-trione (<b>17</b>) were found to have remarkable inhibitory effects against NF-<i>κ</i>B, with IC<sub>50</sub> values of 0.08, 0.61, and 1.60 μM, respectively.https://www.mdpi.com/1420-3049/26/7/1911<i>Rubus chingii</i> HuRosaceaetriterpenoidsrubusacidsditerpenoidsrubusone |
| spellingShingle | Jiang Wan Xiao-Juan Wang Nan Guo Xi-Ying Wu Juan Xiong Yi Zang Chun-Xiao Jiang Bing Han Jia Li Jin-Feng Hu Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects Molecules <i>Rubus chingii</i> Hu Rosaceae triterpenoids rubusacids diterpenoids rubusone |
| title | Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects |
| title_full | Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects |
| title_fullStr | Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects |
| title_full_unstemmed | Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects |
| title_short | Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (<i>Rubus chingii</i> Hu) and Their NF-kappa B Inhibitory Effects |
| title_sort | highly oxygenated triterpenoids and diterpenoids from fructus rubi i rubus chingii i hu and their nf kappa b inhibitory effects |
| topic | <i>Rubus chingii</i> Hu Rosaceae triterpenoids rubusacids diterpenoids rubusone |
| url | https://www.mdpi.com/1420-3049/26/7/1911 |
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