A new natural methoxyfurocoumarin from Heracleum pastinacifolium

Kasumova, G. K.; Serkerov, S. V.

doi:10.1007/s10600-011-9932-2

Cited by 5 publications

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“…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 range of methyls.…”

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confidence: 72%

“…The purity of the compounds was established on Silufol UV-254 chromatographic plates. Total extracted substances were obtained and coumarin derivatives were isolated by the literature methods [2]. Isolation of Psoroheraclin (1).…”

Section: Methodsmentioning

confidence: 99%

“…It is well known that furan proton resonances appear, as a rule, as two 1H doublets with SSCC of ~1.5-2.5 Hz [2,3]. However, the spectrum had three singlets, one (8.05 ppm) of which was related to a proton of the furan ring.…”

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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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confidence: 72%

Section: Methodsmentioning

confidence: 99%

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A new esterified furocoumarin from Heracleum pastinacifolium

Kasumova

Serkerov

2013

Chem Nat Compd

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“…Our research team has carried out phytochemical studies of this genus via bioassay-guided isolation, allowing the identification of different compounds with pharmaceutical effects existing in the active fractions or extracts. In this way, we have isolated the principal furanocoumarin existing in H. platytaenium, reffering to sphondin that exhibits antioxidant and anticholinesterase activity [82]. It is worth noting that this furanocoumarin has been utilized as a pattern to prepare novel active molecules, especially 4'-Aminomethyl-4,5',8-trimethylpsoralen and 4,5,8 trimethylpsoralen (trioxalen) derivatives [102].…”

Section: Chemical Constituentsmentioning

confidence: 99%

Plants of the Genus Heracleum as a Source of Coumarin and Furanocoumarin

2019

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Heracleum is one of the greatest genera of the Umbelliferae family that has more than 120 species. This genus is represented by 109 species in Asia. Common names for the genus or its species include hogweed and cow parsnip. This paper discusses the phytochemistry, ethnopharmacological use and pharmaceutics of Heracleum species. Many kinds of metabolites have been isolated and identified, that furanocoumarins are among the significant ones. Modern pharmacological studies demonstrated that Heracleum and its active compounds have extensive biological activity, particularly in anticonvulsant, antiinflammatory, antifungal, anticancer, anti-psoriatric, anti-vitiligo and antioxidant activities. In clinical test, Heracleum has successfully been utilized to treat psoriasis, vitiligo, carminative, stomachs, pain killer and anticonvulsant.

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“…Their structures were elucidated using spectroscopic analyses (including Infrared (IR), UV, 1 H and 13 C Nuclear magnetic resonance (NMR), nuclear Overhauser effect (NOE), Heteronuclear multiple bond correlation (HMBC), and High resolution electron impact mass spectrometry (HR‐EI‐MS)). Chemical studies on the root extracts of H. pastinacifolium resulted in the isolation of osthol 6 (Kasumova and Serkerov ). 7‐Isopentenyloxycoumarin 7 was isolated from H. lanatum Michx.…”

Section: Phytochemistrymentioning

confidence: 99%

The Genus Heracleum: A Comprehensive Review on Its Phytochemistry, Pharmacology, and Ethnobotanical Values as a Useful Herb

Bahadori

Dinparast

Zengin

2016

Comp Rev Food Sci Food Safe

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Heracleum species, also known as hogweed, are traditionally used as food additives, spices, and flavoring agents. Moreover, these plants are widely used in folklore medicine for the treatment of many disorders such as inflammation, flatulence, stomachache, epilepsy, psoriasis, and as carminative, wound healing, antiseptic, antidiarrheal, tonic, digestive, pain killer, analgesic, and anticonvulsant agents. The genus Heracleum has broad pharmacological activities: anti-inflammatory, antimicrobial, anticholinesterase, anti-oxidant, antiviral, cytotoxic, and anticarcinogenic. A total of 94 compounds have been isolated from plants of the Heracleum genus, all indicating vital biological activities. Also, about 50 compounds have been identified as major components in their essential oils. The genus is rich in several types of bioactive coumarin compounds, with huge potential for the discovery of new coumarins. Various parts of these plants produce essential oils (mainly aliphatic esters and monoterpenes) with a wide spectrum of biological activities. Heracleum species have great potential for applications in the food, cosmetics, perfumery, and pharmaceutical industries due to their broad ethnobotanical uses and pharmacological properties. Accordingly, this review aims to categorize updated and comprehensive information on ethnobotanical uses, phytochemistry, and pharmacology of Heracleum species in order to open new perspectives for future studies, including possible uses as functional ingredients in food products.

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A new natural methoxyfurocoumarin from Heracleum pastinacifolium

Abstract: 547.314Isobergapten, pimpinellin, isopimpinellin, osthole, and a new natural monomethoxyfurocoumarin were isolated and identified from roots of Heracleum pastinacifolium.

Cited by 5 publications

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A new esterified furocoumarin from Heracleum pastinacifolium

A new esterified furocoumarin from Heracleum pastinacifolium

Plants of the Genus Heracleum as a Source of Coumarin and Furanocoumarin

The Genus Heracleum: A Comprehensive Review on Its Phytochemistry, Pharmacology, and Ethnobotanical Values as a Useful Herb

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