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Planta Med 2022; 88(14): 1287-1292
DOI: 10.1055/a-1728-2347
Biological and Pharmacological Activity
Original Papers

Cyclooxygenase Enzyme and Lipid Peroxidation Inhibitory Terpenoids and Steroidal compounds as Major Constituents in Cleome viscosa Leaves

Amila Abishake Dissanayake
1   Bioactive Natural Products and Phytoceuticals Laboratory, Department of Horticulture, Michigan State University, East Lansing, Michigan, USA
,
Kambou Georges
2   Institute of Environmental and Agricultural Research – Farakoba, Department of Vegetables Production, Research Laboratory, Burkina Faso
,
Muraleedharan Gopalan Nair 
1   Bioactive Natural Products and Phytoceuticals Laboratory, Department of Horticulture, Michigan State University, East Lansing, Michigan, USA
› Author AffiliationsSupported by: Michigan Agriculture Experiment Station MICL01680
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Abstract

Bioassay guided study of Cleome viscosa Linn. (Cleomaceae) leaves led to the isolation of a new cembrenoid diterpene (1) and three known compounds (2 – 4) from the hexane extract. The chemical structures of these compounds were elucidated by spectroscopic methods such as NMR (1D and 2D), HRMS and IR and identified and afforded compound 1, malabaric acid (2), stigmast-4-en-3-one (3) and stigmast-4-ene-3,6-dione (4). This is the first report of compounds 1 and 2 from C. viscosa Linn. Isolates were evaluated for anti-inflammatory activity using in vitro cyclooxygenase enzyme (COX-1 and -2) inhibitory assays. The novel cembrenoid diterpene (1) exhibited IC50 values of 8.4 µM for COX-1 enzyme and 45.2 µM for COX-2 enzyme, respectively. Similarly, malabaric acid (2) exhibited IC50 values of 11.5 µM for COX-1 enzyme and 46.9 µM for COX-2 enzyme, respectively. Their inhibitory activities were in par with non-steroidal anti-inflammatory drugs aspirin, ibuprofen and naproxen. Sterols 3 and 4 gave IC50 values of 62.6 and 67.9 µM, respectively for COX-1 enzyme while indicating weak COX-2 enzyme inhibition. Lipid peroxidation inhibitory (LPO) and MTT assays were used to determine antioxidant activity of these compounds. Compounds 1 – 4 showed LPO inhibition with IC50 values between 82 and 100 µM and moderate antioxidant activity in the MTT assay. Biological activities reported for these compounds are for the first time and it support anecdotal medicinal claims of C. viscosa Linn. leaves.

Key words

Cleome viscosa Linn. - Capparaceae - diterpenoids - sterols - anti-inflammatory - antioxidant

Supporting Information

    1H and 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC and HRMS spectra for pure compounds 1 – 4 are in supporting information file (Figs. 1S – 26S). The in vitro bioassay assay (anti-inflammatory and antioxidant) results of pure compounds 1 – 4 are also in supporting information (Figs. 27S – 45S).

  • Supporting Information


Publication History

Received: 28 September 2021

Accepted after revision: 25 December 2021

Accepted Manuscript online:
25 December 2021

Article published online:
09 March 2022

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