Three New Cytotoxic ent-Kaurane Diterpenes from Isodon excisoides
1
School of pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450046, China
2
Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China
3
Collaborative Innovation Center for Respiratory Disease Diagnosis and Treatment & Chinese Medicine Development of Henan Province, Zhengzhou 450046, China
4
National Engineering Laboratory for Quality Control Technology of Chinese Herbal Medicine, Beijing 100700, China
5
Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100500, China
6
Henan Province Hospital of TCM, Zhengzhou 450002, China
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Molecules 2015, 20(9), 17544-17556; https://doi.org/10.3390/molecules200917544
Received: 29 July 2015 / Revised: 9 September 2015 / Accepted: 17 September 2015 / Published: 22 September 2015
(This article belongs to the Section Natural Products Chemistry)
Three types of ent-kaurane diterpenoids were isolated from the aerial parts of Isodon excisoides, including three new diterpenoids, 1α,7α,14β-trihydroxy-20-acetoxy-ent-kaur-15-one (1); 1α,7α,14β,18-tetrahydroxy-20-acetoxy-ent-kaur-15-one (2); and 1α-acetoxy-14β-hydroxy-7α,20-epoxy-ent-kaur-16-en-15-one (3); together with six known diterpenes henryin (4); kamebanin (5); reniformin C (6); kamebacetal A (7); kamebacetal B (8); and oridonin (9). The structures of the isolated compounds were elucidated by means of nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry in conjunction with published data for their analogs, as well as their fragmentation patterns. Compounds 5 and 9 were isolated from Isodon excisoides for the first time. To explore the structure-activity relationships of the isolated compounds, they were tested for their cytotoxic effects against five human cancer cell lines: HCT-116, HepG2, A2780, NCI-H1650, and BGC-823. Most of the isolated compounds showed certain cytotoxic activity against the five cancer cell lines with IC50 values ranging from 1.09–8.53 µM. Among the tested compounds, compound 4 exhibited the strongest cytotoxic activity in the tested cell lines, with IC50 values ranging from 1.31–2.07 µM. Compounds 1, 6, and 7 exhibited selective cytotoxic activity.
View Full-Text
Keywords:
Isodon excisoides; ent-kaurane diterpene; cytotoxic activity; structure-activity relationship
▼
Show Figures
Figure 1
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
MDPI and ACS Style
Dai, L.-P.; Li, C.; Yang, H.-Z.; Lu, Y.-Q.; Yu, H.-Y.; Gao, H.-M.; Wang, Z.-M. Three New Cytotoxic ent-Kaurane Diterpenes from Isodon excisoides. Molecules 2015, 20, 17544-17556.
Show more citation formats- Supplementary File 1:
Supplementary (PDF, 8010 KB)
