土坛树中高度氧化的杜松烷型倍半萜及其生物活性研究
收稿日期: 2023-09-04
修回日期: 2023-10-31
网络出版日期: 2023-11-15
基金资助
海南省重点研发项目(ZDYF2022SHFZ286); 海南省重点研发项目(ZDYF2021SHFZ072); 国家自然科学基金(21662012); 海南省院士创新平台(YSPTZX202030); 中央引导地方科技发展专项(ZY2022HN08); 海南师范大学“大学生创新创业训练计划”(202311658005)
Studies on the Highly Oxidized Cadinane Sesquiterpenes from Alangium salviifolium and Their Bioactivities
Received date: 2023-09-04
Revised date: 2023-10-31
Online published: 2023-11-15
Supported by
Key R&D Projects in Hainan Province-Social Development(ZDYF2022SHFZ286); Key R&D Projects in Hainan Province-Social Development(ZDYF2021SHFZ072); National Natural Science Foundation of China(21662012); Innovation Platform for Academicians of Hainan Province(YSPTZX202030); Central Government Guides Local Science and Technology Development(ZY2022HN08); Hainan Normal University “Innovative Entrepreneurship Training Program for College Students”(202311658005)
从海南民间药用植物土坛树树皮中分离得到2个新的高度氧化的杜松烷型倍半萜类化合物alansalene A (1)和2,7-二羟基-4-异丙基-1-甲基-6-萘醛(5)以及5个已知的同系物, 通过NMR、HR-ESI-MS等多种现代波谱技术确定了其化学结构. 体外抗炎活性显示, 化合物alangene D (2)具有突出的抗炎活性, 其IC50=(2.98±0.11) μmol/L强于阳性对照药物地塞米松[IC50=(39.62±0.12) μmol/L]. 体外α-葡萄糖苷酶抑制活性显示, 化合物alangene F (3)和2,7-二羟基-4-异丙基-6-甲基萘-1-甲醛(6)表现出强的α-葡萄糖苷酶抑制活性, 其IC50值为分别为(111.85±1.80)和(18.55±0.68) μmol/L [阳性对照阿卡波糖IC50=(478.75±27.14) μmol/L].
魏艳梅 , 余章昕 , 杜怡益 , 王平淑 , 岑福凌 , 李小宝 , 陈光英 . 土坛树中高度氧化的杜松烷型倍半萜及其生物活性研究[J]. 有机化学, 2024 , 44(4) : 1363 -1367 . DOI: 10.6023/cjoc202309005
Two new highly oxidized cadinane sesquiterpenes of alansalene A (1) and 2,7-dihydroxy-4-isopropyl-1-methyl- 6-naphthaldehyde (5), and five known analogues were isolated from the barks of Alangium salviifolium, which is a folk medicinal plant in Hainan. The structures were elucidated by spectroscopic methods (1D and 2D NMR, HR-ESI-MS). Compound alangene D (2) exhibited stronger anti-inflammatory activity in vitro with IC50 value of (2.98±0.11) μmol/L to that of dexamethasone [IC50=(39.62±0.12) μmol/L]. Alangene F (3) and 2,7-dihydroxy-4-isopropyl-6-methylnaphthalene-1- carbaldehyde (6) displayed potential α-glucosidase inhibitory activities with IC50 values of (111.85±1.80) and (18.55±0.68) μmol/L, respectively, which were stronger than that of acarbose [IC50=(478.75±27.14) μmol/L].
| [1] | Editorial Board of Flora of China Flora of China, Science Press, Beijing, China, 1983, 52, 160. (in Chinese) |
| [1] | (中国植物志编辑委员会, 中国植物志, 科学出版社, 北京, 1983, 52, 160.) |
| [2] | Chen J.; Han W. D.; Mo D. M.; Wang X. L. Guangdong For. Sci. Technol. 2012, 28, 77. (in Chinese) |
| [2] | (陈杰, 韩维栋, 莫定鸣, 王秀丽, 广东林业科技, 2012, 28, 77.) |
| [3] | Panara K.; Singh P. K.; Rawat P.; Kumar V.; Maruf M.; Patel K.; Ravikumar R. K.; Kumar V. Eur. J. Med. Plants 2016, 12, 1. |
| [4] | Shravya S.; Vinod B. N.; Sunil C. Bull. Fac. Pharm. (Cairo Univ.) 2017, 55, 217. |
| [5] | Yagi N.; Nakahashi H.; Kashima Y.; Miyazawa M. J. Oleo Sci. 2014, 63, 1223. |
| [6] | Sakurai N.; Nakagawa G. K. Ito J.; Sakurai Y.; Nakanishi Y.; Bastow K. F.; Cragg G.; Lee K. H. Phytochemistry 2006, 67, 894. |
| [7] | Cai Y. S.; Wang C.; Tian C.; Sun W. T.; Chen L.; Xiao D.; Zhou S. Y.; Qiu G. F.; Yu J. Q.; Zhu K. K.; Yang S. P. J. Nat. Prod. 2019, 82, 2645. |
| [8] | Hu X. Y.; Wei X.; Zhou Y. Q.; Liu X. W.; Li J. X.; Zhang W.; Wang C. B.; Zhang L. Y.; Zhou Y. Fitoterapia 2020, 147, 104773. |
| [9] | Pailee P.; Prachyawarakorn V.; Ruchirawat S.; Mahidol C. Chem.-Asian J. 2015, 10, 910. |
| [10] | Stipanovic R. D.; Greenblatt G. A.; Beier R. C.; Bell A. A. Phytochemistry 1981, 20, 729. |
| [11] | Zhang Y.; Liu Y. B.; Li Y.; Ma S. G.; Li L.; Qu J.; Zhang D.; Chen X. G.; Jiang J. D.; Yu S. S. J. Nat. Prod. 2013, 76, 1058. |
| [12] | Kubo I.; Muroi H.; Kubo A.; Chaudhuri S.; Sanchez Y.; Ogura T. Planta Med. 1994, 60, 218. |
| [13] | Dirsch V.; Stuppner H.; Vollmar A. Planta Med. 1998, 64, 423. |
| [14] | Cao X.; Yang L.; Dai H. F.; Wei Y. M.; Huang S. Z.; Wang H.; Cai C. H.; Wang L.; Mei W. L.; Chen H. Q. Phytochem. Lett. 2021, 44, 164. |
| [15] | Gerlier D.; Thomasset N. J. Immunol. Methods 1986, 94, 57. |
/
| 〈 |
|
〉 |
