Phytotoxic lignans ofLeucophyllum frutescens

Rimando, Agnes M.; Dayan, Franck E.; Mikell, Julie Rakel; Moraes, Rita M.

doi:10.1002/(sici)1522-7189(199902)7:1<39::aid-nt38>3.0.co;2-2

Cited by 29 publications

(8 citation statements)

References 12 publications

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“…8 Known as cenizo, L. frutescens is a medicinal plant of Mexican traditional medicine, which has long been used to treat lung complaints and specifically tuberculosis. A review of the literature revealed few phytochemical reports for the plant genus, with only one report each on the isolation of phytotoxic lignans from the species 9 and on calmodulin inhibitors from the closely related L. ambiguum . 10 Our work was aimed at the bioassay-guided isolation of the anti-TB active principles of L. frutescens and their detailed structure elucidation, including 13 C INADEQUATE and 1 H NMR full spin analysis, as well as by density functional theory (DFT) calculated vibrational circular dichroism (VCD) spectra of two diastereomers, which were compared in silico to the experimental VCD spectrum of 1 .…”

Section: Introductionmentioning

confidence: 99%

Stereochemical Analysis of Leubethanol, an Anti-TB-Active Serrulatane, fromLeucophyllum frutescens

et al. 2011

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Bioactivity-guided fractionation of the methanolic root bark extract of Leucophyllum frutescens (Berl.) I.M. Johnst. led to the identification of leubethanol (1), a new serrulatane-type diterpene with activity against both multi drug-resistant and drug-sensitive strains of virulent Mycobacterium tuberculosis. Leubethanol (1) was identified by 1D/2D NMR data, as a serrulatane closely related to erogorgiane (2), and exhibited anti-TB activity with minimum inhibitory concentrations in the range 6.25–12.50 µg/mL. Stereochemical evidence for 1 was gleaned from 1D and 2D NOE experiments, 1H-NMR full spin analysis, as well as by comparison of the experimental vibrational circular dichroism (VCD) spectrum to density functional theory calculated VCD spectra of two diastereomers.

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Section: Introductionmentioning

confidence: 99%

Stereochemical Analysis of Leubethanol, an Anti-TB-Active Serrulatane, fromLeucophyllum frutescens

et al. 2011

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“…Metabolites from Leucophyllum species have shown phytotoxic, calmodulin inhibitory, hepatoprotective, antituberculosis, , antimicrobial, , and cytotoxic activities . A few phytochemical analyses of Leucophyllum species can be found in the literature, such as those of L. frutescens , ,, L. ambiguum , and L. texanum . The metabolites isolated from these species include furanolignans, diterpenes, betaines, sterols, and flavones.…”

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confidence: 99%

Furofuranone Lignans from Leucophyllum ambiguum

et al. 2020

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Eight furofuranone lignans with an endo,endo relationship between the oxygen atoms, an exo,exo relationship between the aryl groups, and a chair,chair conformation (1−4 and 6−9), in addition to the α-amino acid (3S)-hydroxy-3′,4′-dimethoxy-L-phenylalanine (5), veratric acid (10), and β-sitosterol (11), were isolated from the powdered and defatted airdried aerial parts of Leucophyllum ambiguum. Four of these lignans, ciquitins A−D, 1−4, were isolated for the first time as natural products. The structures of these compounds were established based on their spectrometric/spectroscopic data. Additionally, single-crystal X-ray crystallography confirmed the structure of ciquitin A (1), and derivatization with (9S)-naproxen and X-ray diffraction crystallography data established its absolute configuration. Ciquitins A (1) and B (2) possess a 9-hydroxy group; this chemical characteristic grants these species conformational isomerism not seen in the other six lignans. The conformers of 1 and 2 are distinguishable via their 1 H and 13 C NMR spectroscopic data. This is the first report of this phenomenon, and hence, a complete assignment of the signals in both spectra of each conformer for each compound is presented. Compounds 1−9 were found to exhibit potent inhibitory activity in the 1.0 × 10 −3 to 2.2 μM range against acetylcholinesterase, an enzyme directly involved in the etiology of Alzheimer's disease and senile dementia. Thus, these natural products are promising agents that are potentially useful for the treatment of neurological degeneration.

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“…162 Kobusin (5), fargesin (11) and epieudesmin (22) were assayed for inhibitory activity against nitric oxide production in LPS stimulated RAW 264.7 cell, but all lignans were inactive. 163 Rimando et al 164 studied furofuran lignans epiyangambin (27), diayangambin (28), diasesartemin (4) and epiaschantin (9) for their phytotoxicity. Diayangambin (28) was the most phytotoxic to Lactuca sativa, showing strong inhibitory activity.…”

Section: Biological Activity Of Furofuran Lignansmentioning

confidence: 99%

Furofuran lignans of Artemisia genus: Isolation, biosynthesis and biological activity

Ickovski

Pavlović

Palić

et al. 2020

JSCS

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Since ancient times, medicinal plants and pharmacologically active products obtained from different natural sources play an important role in human health. Plants belonging to the genus Artemisia possess a great biological potential and it is a well-studied genus in the fields such as systematics (including molecular phylogenetics) and genome organization. Many species of the genus (e.g., A. absinthium, A. annua, A. vulgaris, A. abrotanum, A. arborescens) are widely exploited, because of their high economic value as medicines, food and ornamentals. Withal, in such a large genus, some hiatus must inevitably exist, concerning attainments and potentials that individual species possess. Most of the studies are focused on bioactivity and pharmacology of sesquiterpene lactones. Lignans are unjustly neglected, even though they as well exhibit a wide range of bioactivities. Motivated by that fact, we tried to consolidate findings on bioactive lignans accumulated through the years, with the logical perspectives on further work on isolation and identification of new bioactive lignans and the exploitation of lignans as substances of potential pharmacological interest.

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Phytotoxic lignans ofLeucophyllum frutescens

Cited by 29 publications

References 12 publications

Stereochemical Analysis of Leubethanol, an Anti-TB-Active Serrulatane, fromLeucophyllum frutescens

Stereochemical Analysis of Leubethanol, an Anti-TB-Active Serrulatane, fromLeucophyllum frutescens

Furofuranone Lignans from Leucophyllum ambiguum

Furofuran lignans of Artemisia genus: Isolation, biosynthesis and biological activity

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