Antibacterial and Antimycobacterial Lignans and Flavonoids from Larrea tridentata

Abstract

Three lignans and four flavonoids were isolated and characterized from Larrea tridentata and compounds were tested against 16 bacterial species/strains. Results showed that: dihydroguaiaretic acid (1) had activity towards methicillin resistant (MR) Staphylococcus aureus (minimum inhibitory concentration (MIC) 50 µg/mL) and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis (MIC 12.5-50 µg/mL); 4-epi-larreatricin (2) was active against Enterobacter cloacae (MIC 12.5 µg/mL), as well as sensitive (MIC 50 µg/mL) and MDR strains of M. tuberculosis (MIC 25 µg/mL). 3'-Demethoxy-6-O-demethylisoguaiacin (3) displayed activity against sensitive and resistant S. aureus (MIC 25 µg/mL), Enterococcus faecalis (MIC 12.5 µg/mL), Escherichia coli (MIC 50 µg/mL), E. cloacae (MIC 12.5 µg/mL) and MDR strains of M. tuberculosis (MIC 12.5 µg/mL). 5,4'-Dihydroxy-3,7,8,3'-tetramethoxyflavone (4) and 5,4'-dihydroxy-3,7,8-trimethoxyflavone (5) were active against M. tuberculosis MDR strains having MIC values of 25 and 25-50 µg/mL, respectively, while 5,4'-dihydroxy-7-methoxyflavone (6) was active against S. aureus (MIC 50 µg/mL) and E. faecalis (MIC 50 µg/mL). We concluded that lignan 3 is the main compound responsible for the antibacterial activity of L. tridentata. Lignans 1 and 2 as well as flavonoid 6 contribute with some degree of antibacterial activity. On the other hand, compounds 1, 2, 3, 4 and 5 contributed to the antimycobacterial activity found in L. tridentata.

Prospecting for Bioactive Constituents from Traditional Medicinal Plants through Ethnobotanical Approaches

“…48) This result could provide a pharmacological basis to inhibit PRRSV replication. 27) In addition, many other plant-derived substances from TMPs such as Murraya koenigii, Erythrina caffra, Corydalis saxicola, Larrea tridentate, Holarrhena antidysenterica, and Melampyrum arvense exerted antiviral, 49,50) antibacterial, 51,52) and antiprotozoal 53,54) activities.…”

Plants: A Source for New Antimycobacterial Drugs

“…In Mexico, Larrea tridentata Coville., Zygophyllaceae, has been used as a traditional medicine against respiratory infections and tuberculosis, and its antimycobacterial activity was confirmed using the chloroform extract. In 2012, Favela-Hernández et al reported 5,4′-dihydroxy-3,7,8,3′-tetramethoxyflavone (43) and 5,4′-dihydroxy-3,7,8-trimethoxyflavone (44) from this plant as having activity against both sensitive and MDR forms with MICs of 25 and 25-50 µg/mL, respectively [28]. Limnophila geoffrayi Bon., Scrophulariaceae, a common ingredient in northeastern Thailand curry, is an antipyretic, expectorant, and a lactogogue.…”

“…Adhatoda vasica Ness., Acanthaceae, which is used in the treatment of colds, cough, and other respiratory disorders, contains antimicrobial compounds. Alkaloids present in the hexane extract like vasicine acetate (1) and 2-acetyl ben- [21] dihydroguaiaretic acid (50 µg/mL) (12.5-50 µg/mL) [28] pisonin B (25 µg/mL) [32] falcarindiol (26.7 µg/mL) [65] 2′-nortiliacorinine and tiliacorine (3.1 µg/mL) (3.1 µg/mL) [12] pinocembrin (3.5 µg/mL) [18] (E)-3,2′,4′-trihydroxy-3′-methoxychalcone (174.8 µM) [21] 4-epi-larreatricin (50 µg/mL) (25 µg/mL) [28] [33] licarin A (25 µg/mL) (3.12-12.5 µg/mL) [42] linoleic acid and oleic acid (100 µg/mL) (100 µg/mL) [46] 1,3 dimethoxy-2-methyl-5-pentyl benzene (≤ 2.5 µg/mL) [66] 13′-bromo-tiliacorinine (3.1-6.2 µg/mL) (1.5-3.1 µg/mL) [12] kanzanol C, 4-hydroxylonchocarpin, stipulin, and amentoflavone (9.76 -> 39.06 µg/mL) [19] aminoacetate derivative of diospyrin (> 10 -≤ 50 µg/mL) (> 10 -≤ 50 µg/mL) [34] licarin B (50 µg/mL) (12.5-50 µg/mL) [42] undecanal (100 µg/mL) (50-200 µg/mL) [46] 3-methoxy-2-methyl-5-pentyl phenol (≤ 2.58 µg/mL) [66] Mauritine M (IC 50 − 72.8 µM) [13] genistein (35 µg/ml) [20] diospyrin (100 µg/mL) (100 µg/mL) [34] eupomatenoid-7…”

“…prop-2-en-1-one (30 µg/mL) [45] cordiachrome C (1.5 µg/mL) [52] aromatic alkene, and pyrrolidine amide (25 µg/mL) [69] 5,4′-dihydroxy-3,7,8,3′-tetramethoxy flavones (> 50 µg/mL) (25 µg/mL) [28] palmarumycin JC2 (6.25 µg/mL) [39] Isobavachalcone (18 µg/mL) [45] globiferin (6.2 µg/mL) [52] tetrahydroxy squalene (10 µg/mL) [70] 5,4′-dihydroxy-3,7,8-trimethoxyflavone (> 50 µg/mL) (25-50 µg/mL) [28] α-tocopheryl quinone (25 µg/mL) [40] scopoletin (42 µg/mL) [45] diol derivative of labdane (250 µg/mL) [53] trans,trans-1,7,diphenylhepta-4,6-dien-3-one (> 128 µg/mL) [71] nevadensin and isothymusin (200 µg/mL) [29] 2′,5′′-dimethoxysesamin (63 µg/mL) [47] dioxime derivative of labdane and labdane (500 µg/mL) [53] xanthones (10 µg/mL) [72] pisonivanone (12.5 µg/mL) [32] ethoxycubebin (62.4 µM) [49] caniojane (25 µg/mL) [54] continued phytol derivatives (15.6-50 µg/mL) [64] phytol (100 µg/mL) [64] zylamine (2) inhibited both the sensitive and MDR strains of M. tuberculosis at minimum inhibitory concentrations (MIC) of 50 and 200 µg/mL, respectively [8]. Justicia adhatoda L., Acanthaceae, is known as vasaka in the Indian system of medicine.…”

“…The hexane extract of the plant showed antimycobacterial activity against both sensitive and MDR forms of M. tuberculosis at a concentration of 100-200 µg/mL [46]. The lignans dihydroguaiaretic acid (75) and 4-epi-larreatricin (76) were extracted from L. tridentata Coville., Zygophyllaceae, where 75 and 76 showed activity against both sensitive and MDR forms, with 75 being the most active against MDR forms [28]. A furolignan, 2′,5′′-dimethoxysesamin (77) obtained from the root bark of Leucophyllum frutescens I. M.…”