Chinese Journal of Organic Chemistry >
Diterpenoids from Mangrove Plant Excoecaria agallocha L. and Their Anti-neuroinflammatory Activities
Received date: 2024-04-17
Revised date: 2024-05-27
Online published: 2024-07-10
Supported by
National Natural Science Foundation of China(82204275); National Natural Science Foundation of China(82160653); Hainan Provincial Natural Science Foundation(323MS014)
Normal-phase and reversed-phase silica gel column chromatography and semi-preparative high performance liquid chromatography were applied to study the chemical constituents of the stems and twigs of the Hainan mangrove plant, Excoecaria agallocha L. A new 3,4-seco-ent-kaurane diterpenoid, named agallochanin acid A (1), and a rare ent-tetranorlabdane diterpenoid, named agallochanin acid B (2), along with four known diterpenoids were isolated. Their structures including absolute configurations were characterized via HR-ESI-MS, extensive 1D and 2D NMR investigations and calculated and experimental electronic circular dichroism (ECD) data. All isolates were tested for their inhibitory effects on NO production in lipopolysaccharide (LPS)-activated BV-2 cells. ent-3,4-Seco-17-oxo-kaur-4(19),15(16)-dien-3-oic acid (3) and ent-15-hydroxy- labda-8(17),13E-dien-3-one (5) exhibited considerable anti-neuroinflammatory activities with IC50 values of (14.32±1.99) and (4.24±0.37) μmol/L.
Junyi Li , Lu Yang , Mingbin Chen , Yong Rao , Zhongping Jiang , Ling Huang . Diterpenoids from Mangrove Plant Excoecaria agallocha L. and Their Anti-neuroinflammatory Activities[J]. Chinese Journal of Organic Chemistry, 2024 , 44(11) : 3526 -3530 . DOI: 10.6023/cjoc202404024
| [1] | Zhan Z. J.; Li S.; Chu W.; Yin S. Nat. Prod. Rep. 2022, 39, 2132 |
| [2] | Li M.-Y.; Xiao Q.; Pan J. Y.; Wu J. Nat. Prod. Rep. 2009, 26, 281. |
| [3] | Flora of China Editorial of Committee of Chinese Academy of Sciences Flora of China, Vol. 44, Science Press, Beijing, 1997, p. 6 (in Chinese). |
| [3] | (中国科学院中国植物志编辑委员会, 中国植物志, 第六卷, 科学出版社, 北京, 1997, p. 6.) |
| [4] | Subhan N.; Alam M. A.; Ahmed F.; Shahid I.; Nahar L.; Sarker S. Rev. Bras. Farmacogn. 2008, 18, 521. |
| [5] | Arumugam M.; Pawar U.; Gomathinayagam M.; Lakshmanan G.; Panneerselvam R. Int. Res. J. Pharm. 2012, 3, 235. |
| [6] | Chan E.; Oshiro N.; Kezuka M.; Kimura N.; Baba K.; Chan H. J. Appl. Pharm. Sci. 2018, 8, 166. |
| [7] | Prakash S.; Khan M.; Khan H.; Zaman A. Phytochemistry 1983, 22, 1836. |
| [8] | Anjaneyulu A.; Rao V. Phytochemistry 2000, 55, 891. |
| [9] | Jiang Z.P.; Yu Y.; Shen L. Bioorg. Chem. 2020, 104, 104206. |
| [10] | Wang J. D.; Zhang W.; Li Z. Y.; Xiang W. S.; Guo Y. W.; Krohn K. Phytochemistry 2007, 68, 2426. |
| [11] | Batsa A. J.; Periyasamy K. Int. J. Pharm. Biol. Sci. 2013, 3, 392. |
| [12] | Babuselvam M.; Ravikumar S.; Mohamed Farook K. A.; Abideen S.; Peer Mohamed M.; Uthiraselvam M. J. Appl. Pharm. Sci. 2012, 2, 108. |
| [13] | Erickson K. L.; Beutler J. A.; Cardellina J. H. II.; McMahon J. B.; Newman D. J.; Boyd M. R. J. Nat. Prod. 1995, 58, 769. |
| [14] | Laith A. A.; Najiah M. J. Microbiol. Antimicrob. 2014, 6, 29. |
| [15] | Jiang Z. P.; Luan Z. L.; Liu R. X.; Zhang Q.; Ma C. Z.; Shen L.; Wu J. Mar. Drugs 2018, 16, 488. |
| [16] | Jiang Z. P.; Zou B. H.; Li X. J.; Liu J. J.; Shen L.; Wu J. Fitoterapia 2019, 133, 159. |
| [17] | Chen Y. M.; Yang Y. H.; Li X. N.; Zou C.; Zhao P. J. Molecules 2015, 20, 16924. |
| [18] | Suwancharoen S.; Chonvanich O.; Roengsumran S.; Pornpakakul S. Chem. Nat. Compd. 2012, 48, 583. |
| [19] | Li Y.; Liu J.; Yu S.; Proksch P.; Gu J.; Lin W. H. Phytochemistry 2010, 71, 2124. |
| [20] | Wang J. D.; Dong M. L.; Zhang W.; Shen X.; Guo Y. W. Nat. Prod. Rep. Dev. 2006, 945 (in Chinese). |
| [20] | (王继栋, 董美玲, 张文, 沈旭, 郭跃伟, 天然产物研究与开发, 2006, 945.) |
| [21] | Zhang W. F.; Xiao D. Q.; Mao W.; Xia H. B. Signal Transduction Targeted Ther. 2023, 8, 267. |
| [22] | Kwon H. S.; Koh S. H. Transl. Neurodegener. 2020, 9, 42. |
/
| 〈 |
|
〉 |