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.
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Keywords:
Isodon excisoides; ent-kaurane diterpene; cytotoxic activity; structure-activity relationship
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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. https://doi.org/10.3390/molecules200917544
AMA 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(9):17544-17556. https://doi.org/10.3390/molecules200917544
Chicago/Turabian StyleDai, Li-Ping; Li, Chun; Yang, Han-Ze; Lu, Yan-Qing; Yu, Hong-Yan; Gao, Hui-Min; Wang, Zhi-Min. 2015. "Three New Cytotoxic ent-Kaurane Diterpenes from Isodon excisoides" Molecules 20, no. 9: 17544-17556. https://doi.org/10.3390/molecules200917544
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