Structure of iskenderolide

Serkerov, S. V.; Aleskerova, A. N.

doi:10.1007/s10600-012-0100-0

Cited by 3 publications

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References 3 publications

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“…Compound 1 (0.1 g) was dissolved in pyridine (3 mL), treated with acetic anhydride (5 mL), heated on a water bath for 5 h, left at room temperature overnight, and worked up by the known method [6] to afford diacetate C 21 H 20 O 9 , mp 120-122°C.…”

Section: Methodsmentioning

confidence: 99%

A new esterified furocoumarin from Heracleum pastinacifolium

Kasumova

Serkerov

2013

Chem Nat Compd

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A new esterified furocoumarin (C 17 H 16 O 7 , mp 151-153°C) of the psoralen group was isolated from the roots of Heracleum pastinacifolium. Its structure was established based on chemical and spectral data.Coumarin derivatives from the roots of Heracleum pastinacifolium C. Koch (Apiaceae Lindl.) were previously reported [1,2].In continuation of the chromatographic separation of total extracted substances from the roots of this plant over a column of Al 2 O 3 , a crystalline compound of formula C 17 H 16 O 7 , mp 151-153°C (CHCl 3 :Me 2 CO), was isolated from fractions 65-66 that were obtained by elution with C 6 H 6 :Me 2 CO (3:1).The IR spectrum of 1 exhibited absorption bands of hydroxyls (3550, 3300 cm 1 ), CO of a G-lactone ring and ester (strong bands at 1740, 1300, and 1140), and an aromatic system (1630).Singlets (3H, Table 1 lists chemical shifts of PMR and 13 C NMR resonances of psoroheraclin and its diacetate) for methyls in the PMR spectrum together with a doublet for a methylene and triplet for a gem-hydroxyl methine indicated that the molecule contained a group that was apparently bonded through an ester bond [OCOCH 2 CHOHCOH(CH 3 ) 2 ]. Broad singlets at 3.65 and 5.15 ppm (1H) belonged to protons of two hydroxyls. In addition to these resonances, the PMR spectrum of 1 showed resonances for furocoumarin skeletal protons (H-3, H-4, H-5, H-8, H-2c).The 13 C NMR spectrum of 1 taken with full suppression of proton spin-spin coupling showed 17 singlets, indicating that the molecule comprised 17 C atoms.It was concluded by comparing the physicochemical properties and spectral data (IR, PMR, 13 C NMR, Dept 135, Dept 90) that 1 was a new coumarin derivative that we called psoroheraclin.According to the Dept 135 13 C NMR spectrum, the molecule contained nine resonances belonging to nine protonated C atoms: 25.0 (CH 3 ), 28.0 (CH 3 ), 71.5 (CH 2 O), 75.0 (CHOH), 91.5 (CH=), 97.0 (CH=),103.5 (CH=), 112.0 (CH=), and 149.0 ppm (CH=). According to the Dept 90 13 C NMR spectrum, six of these belonged to one methine (75.0) and five aromatic C atoms (91.5, 97.0, 103.5, 112.0, 149.0 ppm).Thus, eight resonances that did not appear in the Dept 135 spectrum but were seen in the 13 C NMR spectrum of the compound were related to unprotonated C atoms (C-2, C-6, C-7, C-9, C-10, C-3c, C-2s, C-5s).Acetylation of 1 produced the diacetyl derivative (2) of formula C 21 H 20 O 9 , mp 120-122°C, the IR spectrum of which contained strong absorption bands at 1750, 1280, 1270, and 1250 cm 1 that were characteristic of CO of a G-lactone ring and three esters and at 1625 cm 1 (aromatic C=C). The results from the acetylation showed that 1 contained two hydroxyls. Despite the formation of the diacetyl derivative, one of the hydroxyls was tertiary in nature according to the PMR and 13 C NMR spectra of both 1 and its diacetate (Table 1).Thus, the formation of diacetylpsoroheraclin [2] was confirmed by the PMR spectrum where two 3H singlets characteristic of acetyl methyls were observed in the spectrum of the diacetyl derivative in the ran...

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Section: Methodsmentioning

confidence: 99%

A new esterified furocoumarin from Heracleum pastinacifolium

Kasumova

Serkerov

2013

Chem Nat Compd

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“…After a detailed study from a pharmacological point of view, they were proposed for use in medical practice. Ongoing research on the study of sesquiterpene lactones of species of the genus Artemisia L. expands our knowledge on the detection of the substance of the species within the genus [Serkerov et al, 1985;Serkerov, Aleskerova, 1987, 2011.…”

Section: Sesquiterpene Lactones In the Aerial Part Of Artemisia Maritima Lmentioning

confidence: 99%

Sesquiterpene lactones in the aerial part of Artemisia maritima L.

Serkerov¹

2019

plantfungalres

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Three substances are separated from the above-ground part of Artemisia maritima L. by column chromatography method in an individual state: C 15 H 18 O 3 with a m.p. of 171-172°C (substance 1), C 15 H 18 O 3 with a melting temperature of 130-131°C (substance 2), C 15 H 18 O 4 with a melting point of 201-202°С (substance 3), which are identified as α-santonin, glabellin and artemisin on the basis of 1 H NMR spectra and direct comparison of IR spectra.

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