New diterpene lactone derivatives from Aphanamixis polystachya leaves inhibit nitric oxide production in RAW 264.7 cells

被引:2
作者
Bang, Ngo Anh [1 ,2 ]
Yen, Duong Thi Hai [1 ]
Hang, Dan Thi Thuy [1 ]
Yen, Pham Hai [1 ]
Hoang, Nguyen Huy [1 ]
Trang, Do Thi [1 ]
Dung, Duong Thi [1 ]
Cuc, Nguyen Thi [1 ]
Cuong, Nguyen The [3 ]
Nhiem, Nguyen Xuan [1 ,2 ]
Tai, Bui Huu [1 ,2 ]
Kiem, Phan Van [1 ,2 ]
机构
[1] Vietnam Acad Sci & Technol VAST, Inst Marine Biochem, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
[2] Grad Univ Sci & Technol, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
[3] VAST, Inst Ecol & Biol Resources, 18 Hoang Quoc Viet, Hanoi 10072, Vietnam
关键词
A-D; CONSTITUENTS; LIMONOIDS; MELIACEAE; DIMERS;
D O I
10.1039/d4ra02968b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phytochemical studies on Aphanamixis plants have attracted considerable attention over the past few decades due to the structural diversities and significant biological activities of terpenoids produced by these plants. In the present study, five new acyclic diterpene lactone derivatives, aphanamixionolides A-E (1-5), and three known tirucallane-type triterpenes, namely, piscidinol A (6), hispidone (7), and bourjotinolone A (8), were isolated from the leaves of Aphanamixis polystachya. Their structures were elucidated by comprehensive analyses of HR-ESI-MS and NMR spectroscopic data and by comparison with those reported in the literature. Absolute configurations of the new compounds were determined by experimental and TD-DFT calculated ECD spectra. Compounds 1-8 inhibited NO production with IC50 values of 10.2-37.7 mu M, which are comparable to positive control l-NMMA (IC50: 31.5 mu M).
引用
收藏
页码:20536 / 20542
页数:7
相关论文
共 18 条
[1]   Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity [J].
Bai, Wei ;
Yang, Hong-Ying ;
Jiao, Xing-Zhi ;
Feng, Ke-Na ;
Chen, Jian-Jun ;
Gao, Kun .
JOURNAL OF NATURAL PRODUCTS, 2018, 81 (08) :1777-1785
[2]   Limonoids from Aphanamixis polystachya and Their Antifeedant Activity [J].
Cai, Jie-Yun ;
Chen, Duo-Zhi ;
Luo, Shi-Hong ;
Kong, Ning-Chuan ;
Zhang, Yu ;
Di, Ying-Tong ;
Zhang, Qiang ;
Hua, Juan ;
Jing, Shu-Xi ;
Li, Shun-Lin ;
Li, Sheng-Hong ;
Hao, Xiao-Jiang ;
He, Hong-Ping .
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (03) :472-482
[3]   Guaianolide sesquiterpenes and benzoate esters from the aerial parts of Siegesbeckia orientalis L. and their xanthine oxidase inhibitory activity [J].
Dan Thi Thuy Hang ;
Do Thi Trang ;
Duong Thi Dung ;
Duong Thi Hai Yen ;
Nguyen Huy Hoang ;
Ngo Anh Bang ;
Nguyen Thi Cuc ;
Nguyen Xuan Nhiem ;
Phan Thi Thanh Huong ;
Bui Huu Tai ;
Phan Van Kiem .
PHYTOCHEMISTRY, 2021, 190
[4]   Rhabdastrenones A-D from the sponge Rhabdastrella globostellata [J].
Do Thi Trang ;
Dan Thi Thuy Hang ;
Duong Thi Dung ;
Nguyen Thi Cuc ;
Pham Hai Yen ;
Phan Thi Thanh Huong ;
Le Thi Huyen ;
Nguyen Thi Mai ;
Nguyen Xuan Nhiem ;
Bui Huu Tai ;
Phan Van Kiem .
RSC ADVANCES, 2022, 12 (17) :10646-10652
[5]   Aphapolins A and B: Two Nemoralisin Diterpenoids Isolated from Aphanamixis polystachya (Wall.) R. Parker [J].
Fang, Fu-Hu ;
Huang, Wen-Jun ;
Zhou, Shuang-Yan ;
Han, Zheng-Zhi ;
Li, Man-Yu ;
Liu, Li-Fang ;
Wu, Xiao-Zhen ;
Yao, Xiao-Jun ;
Li, Ya ;
Yuan, Cheng-Shan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (30) :4429-4433
[6]   CONSTITUENTS OF TRICHILIA-HISPIDA (MELIACEAE) .2. A NEW TRITERPENOID, HISPIDONE, AND BOURJOTINOLONE-A [J].
JOLAD, SD ;
HOFFMANN, JJ ;
COLE, JR ;
TEMPESTA, MS ;
BATES, RB .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :3132-3135
[7]   Aphadilactones A-D, Four Diterpenoid Dimers with DGAT Inhibitory and Antimalarial Activities from a Meliaceae Plant [J].
Liu, Jia ;
He, Xiu-Feng ;
Wang, Gai-Hong ;
Merino, Emilio F. ;
Yang, Sheng-Ping ;
Zhu, Rong-Xiu ;
Gan, Li-She ;
Zhang, Hua ;
Cassera, Maria B. ;
Wang, He-Yao ;
Kingston, David G. I. ;
Yue, Jian-Min .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) :599-607
[8]   Tirucallane-type triterpenoids: nmr and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A [J].
McChesney, JD ;
Dou, JH ;
Sindelar, RD ;
Goins, DK ;
Walker, LA ;
Rogers, RD .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1997, 27 (05) :283-290
[9]   Phytochemical investigation of Aglaia andamanica [J].
Puripattanavong, J ;
Weber, S ;
Brecht, V ;
Frahm, AW .
PLANTA MEDICA, 2000, 66 (08) :740-745
[10]   Undescribed sesquiterpene-diterpene heterodimers from the fruits of Aphanamixis polystachya selectively modulate inflammatory markers in RAW 264.7 cells [J].
Tai, Bui Huu ;
Bang, Ngo Anh ;
Yen, Pham Hai ;
Yen, Duong Thi Hai ;
Cuc, Nguyen Thi ;
Dung, Duong Thi ;
Huong, Phan Thi Thanh ;
Trang, Do Thi ;
Nhiem, Nguyen Xuan ;
Cuong, Nguyen The ;
Van Kiem, Phan .
PHYTOCHEMISTRY, 2024, 220