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United States Department of Agriculture

Agricultural Research Service

Research Project: Discovery and Development of Natural Product-based Weed Management Methods

Location: Natural Products Utilization Research

Title: Antimicrobial and antiparastic abietane diterpenoids from Cupressus sempervirens

Authors
item Zhang, Jin -
item Rahman, Azia -
item Jain, Surendra -
item Jacob, Melissa -
item Khan, Shabana -
item Tekwani, Babu -
item Muhammad, Llias -

Submitted to: Research and Reports in Medicinal Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 1, 2012
Publication Date: April 11, 2012
Citation: Zhang, J., Rahman, A.A., Jain, S., Jacob, M.R., Khan, S.I., Tekwani, B.L., Muhammad, L. 2012. Antimicrobial and antiparastic abietane diterpenoids from Cupressus sempervirens. Research and Reports in Medicinal Chemistry. 2:1-6.

Interpretive Summary: Cupressus sempervirens L. (Cupressaceae) is a species of cypress native to the eastern Mediterranean region and is naturalized in the USA. A sample of the fruits (cones) of this plant was collected from Oxford, Mississippi during the fall of 2010. The ethanol extract of the powdered cone exhibited potent antileishmnial and antimicrobial activities, as well as moderate antimalarial activity. A bioautography (antibacterial and antifungal) of the extract was carried out to locate active antimicrobial compounds (spots) on TLC plate, which demonstrated two clear zones of inhibition. Therefore, a bioassay-guided fractionation, followed by repeated purification of active fractions using a chromatotron (CPTLC), yielded two potent antileishmanial and antimicrobial diterpenes identified as 6-deoxytaxodione [11-hydroxy-7,9(11),13-abietatrien-12-one] and taxodione, together with ferruginol and sugiol. All the four compounds were evaluated against L. donovani amastigots in THP1 macrophage cultures, of which 6-deoxytaxodione showed most potent activity, similar to standard antileishmanial drug pentamidine. The antileishmanial activity of 6-deoxytaxodione had not been evaluated before, and further evaluation of this compound is in progress.

Technical Abstract: Cupressus sempervirens L. (Cupressaceae) is a species of cypress native to the eastern Mediterranean region. The ethanol extract of the powdered cone (fruits) of this plant, collected from Oxford, Mississippi, USA during the fall of 2010, exhibited potent antimicrobial and antiparastic activities. Bevaluated against L. donovani amastigotes in THP1 macrophage cultures. Both 1 and 2 showed potent activities (IC50 0.8 µg/mL) against methicillin-resistant Staphylococcus aureus. Compounds 1 and 2 had previously been isolated from Clerodendrum eriophyllum, where 2 showed potent cytotoxic activity. However, this is the first report of antimicrobial and antileishmanial activity of compound 1.

Last Modified: 8/22/2014