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Planta Med 2022; 88(06): 455-465
DOI: 10.1055/a-1449-2642
Natural Product Chemistry and Analytical Studies
Original Papers

Chemical Constituents from Chloranthus elatior and Their Inhibitory Effect on Human Dihydroorotate Dehydrogenase

Qian Yang‡
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
2   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
,
An Jia‡
3   Medical School, Huanghe Science & Technology College, Zhengzhou, Peopleʼs Republic of China
,
Xizi Liu
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
2   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
,
Shiyi Han
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
2   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
,
Siyang Fan
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
2   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
› Author AffiliationsSupported by: the National Natural Science Foundation of China No. 81603279
Supported by: the National Science and Technology Project of China No. 2018ZX09731-016
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Abstract

A new sesquiterpene, chlorantholide G (1), a new sesquiterpene dimer, elatiolactone (2), and 2 new diterpenes, elatiorlabdane B (3) and elatiorlabdane C (4), together with 51 known compounds, were isolated from the aerial parts of Chloranthus elatior. The new structures including their absolute configurations were mainly established by mass spectrometric, NMR, and electronic circular dichroism experiments. All isolated compounds were tested for their anti-hDHODH activity. (4S,6R)-4-hydroxy-6-isopropyl-3-methylcyclohex-2-enone (5) and (4S,5R,9S,10R)-8(17),12,14-labdatrien-18-oic acid (29) were the most active compounds with IC50 values of 18.7 and 30.7 µM, respectively.

Key words

Chloranthus elatior - Chloranthaceae - sesquiterpenes - sesquiterpene dimers - diterpenes - hDHODH inhibition

Supporting Information

    1D/2D NMR and HRESIMS spectra of compounds 1–4, optimized geometries and calculated ECD spectra of conformers of compounds 1–4, details of the peaks in the UPLC-MS profile of the dichloromethane extract as well as NMR data of compounds 5–55 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 19 November 2020

Accepted after revision: 31 March 2021

Article published online:
26 April 2021

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