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Molecules 2014, 19(3), 2819-2828; doi:10.3390/molecules19032819
Article

New Thiophene and Flavonoid from Tagetes minuta Leaves Growing in Saudi Arabia

1,* , 2
,
3
 and
4
1 Department of Pharmacognosy, Faculty of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia 2 Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt 3 Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt 4 National Center for Natural Products Research, Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
* Author to whom correspondence should be addressed.
Received: 28 January 2014 / Revised: 25 February 2014 / Accepted: 25 February 2014 / Published: 4 March 2014
(This article belongs to the Section Natural Products)
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Abstract

Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-O-caffeoyl-β-D-glucopyranoside) (9), in addition to seven known compounds: quercetin-3,6-dimethyl ether (2), quercetin-3-methyl ether (3), quercetin (4), axillarin-7-O-β-D-glucopyranoside (5), quercetagetin-3,7-dimethoxy-6-O-β-D-glucopyranoside (6), quercetagetin-7-methoxy-6-O-β-D-glucopyranoside (7), and quercetagetin-6-O-β-D-glucopyranoside (8). The compounds were identified by UV, IR, 1D, 2D NMR, and HRESIMS spectral data. They showed significant antioxidant activity, comparable with that of propyl gallate. Compounds 8 and 3 showed weak to moderate antileishmanial and antimalarial activities, with IC50 values of 31.0 μg/mL and 4.37 μg/mL, respectively.
Keywords: Tagetes minuta; Asteraceae; thiophene; quercetagetin; antioxidant; antimicrobial; antileishmanial; antimalarial Tagetes minuta; Asteraceae; thiophene; quercetagetin; antioxidant; antimicrobial; antileishmanial; antimalarial
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Al-Musayeib, N.M.; Mohamed, G.A.; Ibrahim, S.R.M.; Ross, S.A. New Thiophene and Flavonoid from Tagetes minuta Leaves Growing in Saudi Arabia. Molecules 2014, 19, 2819-2828.

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