Cyclic farnesyl-coumarin and farnesyl-chromone derivatives from Ferula communis subsp. Communis

Miski, Mahmut; Jakupovic, Jasmin

doi:10.1016/0031-9422(90)85054-j

Cited by 60 publications

(14 citation statements)

References 9 publications

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“…The 4 CH 2 groups of the side chain at C(2'') appeared as m at d 1.75 ± 1.70 (CH 2 (1)), 2.22 ± 2.15 (CH 2 (2)), 1.97 ± 1.93 (CH 2 (5)), and 2.06 ± 2.01 (CH 2 (6)) [7]. The (CH 2 (4'') group gave rise to 2 dd (ABX) at (12)) [5].…”

supporting

confidence: 57%

“…398.2093) indicating ten degrees of unsaturation. The IR spectrum exhibited the typical absorptions for OH (3250 cm À1 ), conjugated CO (1707 cm À1 ), and aromatic moieties (1610 and 1470 cm À1 ), while the characteristic UV absorptions at 289, 260, 248, and 243 nm indicated the presence of a benzopyran skeleton for 1 [5]. The 1 H-and 13 C-NMR (Tables 1 and 2), HMBC, HMQC, and NOESY data established that baigene…”

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confidence: 99%

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Newα-Glucosidase Inhibitors from the Mongolian Medicinal PlantFerula mongolica

Choudhary

Baig

Nur-E-Alam

et al. 2001

HCA

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The four new and four known sesquiterpenoid derivatives 1 ± 4 and 5 ± 8, respectively, were isolated from the air-dried roots of Ferula mongolica. The structures of these compounds were determined by spectroscopic methods and found to be rel-(4), (4E,8E)-1-(2-hydroxy-4-methoxyphenyl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (5), the rel-(2R,3S) diastereoisomer 6 of 2, the rel-(2R,3S) diastereoisomer 7 of 4, and (4E,8E)-1-(2,4-dihydroxyphenyl)-5,9,13trimethyltetradeca-4,8,12-trien-1-one (8). These compounds were tested as inhibitors against the enzyme aglucosidase. The compounds 1 ± 6 and 8 exhibited significant inhibitory activity and, therefore, represent a new class of a-glucosidase inhibitors. HÀC(5') 7.91 (d, J 8.7) 7.94 (d, J 8.5) 7.50 (d, J 8.5) 7.58 (d, J 9.4) 6.49 (dd, J 2.5, 8.5) 7.93 (d, J 8.7) 7.57 (d, J 9.3) 6.49 (dd, J 2.5, 8.5) HÀC(6') 6.88 (dd, J 2.2, 8.7) 6.90 (dd, J 2.0, 8.5) 6.80 (dd, J 2.0, 8.5) 6.96 (dd, J 2.2, 9.4) 7.79 (d, J 8.9) 6.90 (dd, J 2.2, 8.7) 6.95 (dd, J 2.3, 9.4) 7.79 (d, J 8.9) HÀC(8') 6.76 (d, J 2.2) 6.81 (d, J 2.0) 6.73 (d, J 2.0) 6.93 (d, J 2.2) ± 6.81 (d, J 2.2) 6.93 (d, J 2.3) ±

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confidence: 57%

mentioning

confidence: 99%

Newα-Glucosidase Inhibitors from the Mongolian Medicinal PlantFerula mongolica

Choudhary

Baig

Nur-E-Alam

et al. 2001

HCA

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“…For example, the molecular modeling studies of a group of coumarin-specific PTs also might provide interesting information, because currently characterized coumarin PTs have variable regioselectivity and prenyl donor preferences (Karamat et al, 2014;Munakata et al, 2014Munakata et al, , 2016. Furthermore, O-farnesylated as well as C-farnesylated coumarins have been reported as plant natural products (Miski and Jakupovic, 1990;Gliszczyńska and Brodelius, 2012), suggesting that there are additional unidentified PTs with novel catalytic functions in their biosynthesis. In this way, coumarin-specific PTs may be the most diversified group of aromatic PTs involved in plant secondary metabolism, along with RdPT1, which has a close evolutionary relationship with coumarin PTs.…”

Section: Molecular and Biochemical Characterization Of Rdpt1mentioning

confidence: 99%

An Aromatic Farnesyltransferase Functions in Biosynthesis of the Anti-HIV Meroterpenoid Daurichromenic Acid

et al. 2018

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Rhododendron dauricum produces daurichromenic acid, an anti-HIV meroterpenoid, via oxidative cyclization of the farnesyl group of grifolic acid. The prenyltransferase (PT) that synthesizes grifolic acid is a farnesyltransferase in plant specialized metabolism. In this study, we demonstrated that the isoprenoid moiety of grifolic acid is derived from the 2-C-methyl-d-erythritol-4-phosphate pathway that takes place in plastids. We explored candidate sequences of plastid-localized PT homologs and identified a cDNA for this PT, RdPT1, which shares moderate sequence similarity with known aromatic PTs. RdPT1 is expressed exclusively in the glandular scales, where daurichromenic acid accumulates. In addition, the gene product was targeted to plastids in plant cells. The recombinant RdPT1 regiospecifically synthesized grifolic acid from orsellinic acid and farnesyl diphosphate, demonstrating that RdPT1 is the farnesyltransferase involved in daurichromenic acid biosynthesis. This enzyme strictly preferred orsellinic acid as a prenyl acceptor, whereas it had a relaxed specificity for prenyl donor structures, also accepting geranyl and geranylgeranyl diphosphates with modest efficiency to synthesize prenyl chain analogs of grifolic acid. Such a broad specificity is a unique catalytic feature of RdPT1 that is not shared among secondary metabolic aromatic PTs in plants. We discuss the unusual substrate preference of RdPT1 using a molecular modeling approach. The biochemical properties as well as the localization of RdPT1 suggest that this enzyme produces meroterpenoids in glandular scales cooperatively with previously identified daurichromenic acid synthase, probably for chemical defense on the surface of R. dauricum plants.

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“…Ferula communis subsp. communis [22][23][24] and F. tingitana [25,26] from Subgenus Ferula yield several sesquiterpene coumarin ethers and sesquiterpene esters; F. elaeochytris Korov. [27], F. orientalis [28], F. rigidula [29], F. haussknechtii [30] and F. lycia Boiss.…”

Section: Introductionmentioning

confidence: 99%

A New Ferula (Apiaceae) Species from Southwest Anatolia: Ferula pisidica Akalın & Miski

Akalin

Tuncay

Olcay

et al. 2020

Plants

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Ferula pisidica is a novel endemic species found in the vicinity of Karaman province of inner Mediterranean Region of Turkey. F. pisidica is morphologically distinct from F. haussknechtii and F. brevipedicellata by habit, sheaths, terminal leaf lobes, and mericarp size as well as by chemotaxonomic differences. The new species is described by morphological, carpological, ecological and phytochemical characteristics. Its relationships with the other related species and proposed conservation status will be reviewed.

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Cyclic farnesyl-coumarin and farnesyl-chromone derivatives from Ferula communis subsp. Communis

Cited by 60 publications

References 9 publications

Newα-Glucosidase Inhibitors from the Mongolian Medicinal PlantFerula mongolica

Newα-Glucosidase Inhibitors from the Mongolian Medicinal PlantFerula mongolica

An Aromatic Farnesyltransferase Functions in Biosynthesis of the Anti-HIV Meroterpenoid Daurichromenic Acid

A New Ferula (Apiaceae) Species from Southwest Anatolia: Ferula pisidica Akalın & Miski

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