Additional Flavonoids from the Leaves of Larrea tridentata

Bernhard, Heinz O.; Thiele, K.

doi:10.1055/s-2007-971684

Cited by 13 publications

(4 citation statements)

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“…Structures were assigned with the aid of detailed 1 H and 2D NMR analysis, UV spectroscopy with UV-Vis shift reagents, and by comparison with literature data. While flavonoids 9-11 and 13-14 have been previously reported from L. tridentata[21][22][23][24], compounds 12 and 15 were found for the first time in this species. Flavonoids 11 (IC 50 8.…”

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confidence: 56%

Library-based Discovery of DYRK1A/CLK1 Inhibitors from Natural Product Extracts

et al. 2012

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The dual specificity tyrosine-phosphorylation-regulated kinase DYRK1A possesses diverse roles in neuronal development and adult brain physiology, and increased activity has been linked to neurodegenerative diseases. Very few inhibitors of this kinase have been reported up to now. Screening of a library of > 900 plant and fungal extracts afforded 25 extracts with IC₅₀s < 10 µg/mL against DYRK1A. To identify the active constituents, the extracts were submitted to a process integrating physicochemical data with biological information, referred to as HPLC-based activity profiling. Follow-up investigation of four extracts led to the targeted isolation of harmine (1, IC₅₀ 0.022 µM) from Peganum harmala, emodin (3, IC₅₀ 4.2 µM) from Cassia nigricans, kaempferol (4, IC₅₀ 0.91 µM) from Cuscuta chinensis, and 3,8-di-O-methylherbacetin (11, IC₅₀ 8.6 µM), 3,3',4'-tri-O-methylmyricetin (12, IC₅₀ 7.1 µM) and ombuin (15, IC₅₀ 1.7 µM) from Larrea tridentata as the active constituents. Active extracts and compounds were also tested on the closely related cdc2-like kinase CLK1. Finally, the selectivity profile of compounds was evaluated by including other members of the DYRKs and CLKs families. While the flavonoids and emodin did not show significant differences in the potency of their activities, harmine (1) was most active against DYRK1A, CLK1, and CLK4, and less potent against the other kinases, with selectivity ranging from 2- to 20-fold.

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confidence: 56%

Library-based Discovery of DYRK1A/CLK1 Inhibitors from Natural Product Extracts

et al. 2012

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“…The seven isolated compounds (Fig. ) were characterized as lignans – dihydroguaiaretic acid ( 1 ; Gnabre et al ., ), 4‐ epi ‐larreatricin ( 2 ; Konno et al ., ), 3′‐demethoxy‐6‐ O ‐demethylisoguaiacin ( 3 ; Konno et al ., ) – and flavonoids – 5,4′‐dihydroxy‐3,7,8,3′‐tetramethoxyflavone ( 4 ; Bernhard and Thiel, ), 5,4′‐dihydroxy‐3,7,8‐trimethoxyflavone ( 5 ; Bernhard and Thiel, ), 5,4′‐dihydroxy‐7‐methoxyflavone ( 6 ; Sakakibara et al ., ) and 5,8,4′‐trihydroxy‐3,7‐dimethoxyflavone ( 7 ; Sakakibara et al ., ) – by analysing their NMR spectra and comparing their spectroscopic data with those in literature. 1 H‐ and 13 C‐NMR spectra were obtained on a 400 MHz Bruker NMR spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Antibacterial and Antimycobacterial Lignans and Flavonoids from Larrea tridentata

Favela-Hernández

García

Garza‐González

et al. 2012

Phytotherapy Research

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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.

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“…Herbacetin-7,8-diMe was thus far found only twice as an aglycone, namely in flower heads of Eupatorium gracile (Torrenegra et al, 1984) and in the farinose frond exudate of the fern Cheilanthes argentea (Wollenweber and Roitman, 1991). Herbacetin-3,7,8-triMe was known as an exudate constitutent from Larrea tri dentata (Zygophyllaceae) (Bernhard and Thiele, 1981) and from Cleome spinosa (Wollenweber and Dörr, 1992). Plant sources for further relatively rare methyl derivatives of 8-hydroxygalangin, herbacetin, and gossypetin are found in (Wollenweber, 1988) and (Wollenweber, 1994).…”

Section: Flavonoid Distributionmentioning

confidence: 99%

Rare Flavonoids from Odixia and Ozothamnus spp. (Asteraceae, Gnaphalieae)

Wollenweber

Dörr

Beyer

et al. 1997

Zeitschrift Für Naturforschung C

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Representatives of the genera Odixia and Ozothamnus, Australian Asteraceae belonging to the tribe Gnaphalieae, have been analyzed for the presence of flavonoid aglycones accumulated on leaf and stem surfaces. Fiftytwo more or less lipophilic flavonoids have been identified. Methyl ethers of apigenin, luteolin, kaempferol and quercetin are abundant, while rare methyl ethers of isoscutellarein, 8-hydroxy galangin, herbacetin and gossypetin appear to be characteristic. The distribution of rare flavonoids is discussed

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Additional Flavonoids from the Leaves of Larrea tridentata

Cited by 13 publications

References 0 publications

Library-based Discovery of DYRK1A/CLK1 Inhibitors from Natural Product Extracts

Library-based Discovery of DYRK1A/CLK1 Inhibitors from Natural Product Extracts

Antibacterial and Antimycobacterial Lignans and Flavonoids from Larrea tridentata

Rare Flavonoids from Odixia and Ozothamnus spp. (Asteraceae, Gnaphalieae)

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