Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities
Five new arylnaphthalide lignans (1 − 4a/4b), together with five known analogues (5–9), were isolated from whole plants of Saussurea medusa. Compound 4 was characterized as an aryltetralin lignan with an unusual C-7′-C-9 oxygen bridge group, and a chiral HPLC analysis was carried out to afford one p...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-10-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535222004713 |
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| author | Jing-Ya Cao Qi Dong Zhi-Yao Wang Ye Zhao Yu Ren Chang Liu Jun Dang Rui-Tao Yu Yan-Duo Tao |
| author_facet | Jing-Ya Cao Qi Dong Zhi-Yao Wang Ye Zhao Yu Ren Chang Liu Jun Dang Rui-Tao Yu Yan-Duo Tao |
| author_sort | Jing-Ya Cao |
| collection | DOAJ |
| description | Five new arylnaphthalide lignans (1 − 4a/4b), together with five known analogues (5–9), were isolated from whole plants of Saussurea medusa. Compound 4 was characterized as an aryltetralin lignan with an unusual C-7′-C-9 oxygen bridge group, and a chiral HPLC analysis was carried out to afford one pair of enantiomers (4a/4b). Structures of the new compounds were elucidated by extensive spectroscopic and electronic circular dichroism (ECD) calculations. All compounds were firstly isolated from S. medusa, and compounds 1–5, 7 and 8 had never been obtained from the genus Saussurea previously. Furthermore, this is the first report of arylnaphthalide lignans isolated from S. medusa. anti-inflammatory activities of the compounds were evaluated by determining their inhibitory activities on the production of NO by LPS-stimulated RAW 264.7 cells. Compounds (−)-4a and 5 exerted the significant inhibition activities with IC50 values of 13.4 ± 1.5 and 15.7 ± 1.1 μM, respectively, which even exceeded the positive control quercetin (IC50 = 15.9 ± 1.2 μM). Compounds 2, (+)-4b, 6 and 9 exhibited moderate inhibitory activities with IC50 values ranging from 19.7 ± 1.9 to 47.4 ± 3.1 μM. Further analysis by molecular docking showed that almost all the active compounds could interact with the amino acid residues of iNOS proteins, which also supported their anti-inflammatory activities. |
| first_indexed | 2024-04-11T09:54:16Z |
| format | Article |
| id | doaj.art-979e9cb807ab49a091b0401acd892a46 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-11T09:54:16Z |
| publishDate | 2022-10-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-979e9cb807ab49a091b0401acd892a462022-12-22T04:30:42ZengElsevierArabian Journal of Chemistry1878-53522022-10-011510104155Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activitiesJing-Ya Cao0Qi Dong1Zhi-Yao Wang2Ye Zhao3Yu Ren4Chang Liu5Jun Dang6Rui-Tao Yu7Yan-Duo Tao8Qinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, PR China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, PR ChinaQinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, PR ChinaHenan Academy of Science, Zhengzhou 450002, PR ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR ChinaQinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, PR ChinaQinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, PR China; Corresponding authors at: Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, PR China.Qinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, PR China; Corresponding authors at: Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, PR China.Five new arylnaphthalide lignans (1 − 4a/4b), together with five known analogues (5–9), were isolated from whole plants of Saussurea medusa. Compound 4 was characterized as an aryltetralin lignan with an unusual C-7′-C-9 oxygen bridge group, and a chiral HPLC analysis was carried out to afford one pair of enantiomers (4a/4b). Structures of the new compounds were elucidated by extensive spectroscopic and electronic circular dichroism (ECD) calculations. All compounds were firstly isolated from S. medusa, and compounds 1–5, 7 and 8 had never been obtained from the genus Saussurea previously. Furthermore, this is the first report of arylnaphthalide lignans isolated from S. medusa. anti-inflammatory activities of the compounds were evaluated by determining their inhibitory activities on the production of NO by LPS-stimulated RAW 264.7 cells. Compounds (−)-4a and 5 exerted the significant inhibition activities with IC50 values of 13.4 ± 1.5 and 15.7 ± 1.1 μM, respectively, which even exceeded the positive control quercetin (IC50 = 15.9 ± 1.2 μM). Compounds 2, (+)-4b, 6 and 9 exhibited moderate inhibitory activities with IC50 values ranging from 19.7 ± 1.9 to 47.4 ± 3.1 μM. Further analysis by molecular docking showed that almost all the active compounds could interact with the amino acid residues of iNOS proteins, which also supported their anti-inflammatory activities.http://www.sciencedirect.com/science/article/pii/S1878535222004713Saussurea medusaArylnaphthalide lignanAnti-inflammatory activityECD calculationMolecular docking |
| spellingShingle | Jing-Ya Cao Qi Dong Zhi-Yao Wang Ye Zhao Yu Ren Chang Liu Jun Dang Rui-Tao Yu Yan-Duo Tao Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities Arabian Journal of Chemistry Saussurea medusa Arylnaphthalide lignan Anti-inflammatory activity ECD calculation Molecular docking |
| title | Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities |
| title_full | Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities |
| title_fullStr | Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities |
| title_full_unstemmed | Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities |
| title_short | Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities |
| title_sort | arylnaphthalide lignans from saussurea medusa and their anti inflammatory activities |
| topic | Saussurea medusa Arylnaphthalide lignan Anti-inflammatory activity ECD calculation Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S1878535222004713 |
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