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Juncaceae Species as Promising Sources of Phenanthrenes: Antiproliferative Compounds from Juncus maritimus Lam.

ABSTRACT: Juncaceae family represents an abundant source of phenanthrenes. In continuation of our work aiming at the isolation of biologically active compounds from Juncaceae species, Juncus maritimus Lam. was subjected to phytochemical and pharmacological investigations. The isolation process was carried out by using combined extraction and chromatographic methods. The structures of the obtained chemical compounds were elucidated by spectroscopic analysis, including HRESIMS, 1D (¹H, ¹³C-JMOD), and 2D (¹H-¹H-COSY, HSQC, HMBC, NOESY) NMR spectra. Four new [maritins A-D (1-4)] and seven known phenanthrenes (5-11) were isolated from the plant, of which two (4 and 11) are phenanthrene dimers composed of effusol monomers. Maritin C (3) has an unusual 4,5-ethanophenanthrene skeleton most likely produced by biosynthetic incorporation of a vinyl group into a cyclohexadiene ring. Compounds 1-11 were tested for their antiproliferative activity on seven human tumor cell lines (HeLa, HTM-26, T-47D, A2780, A2780cis, MCF-7, KCR) and one normal cell line (MRC-5) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The dimeric phenanthrenes showed strong antiproliferative activity against T-47D cells with IC₅₀ values of 9.1 and 6.2 µM, respectively.

SUBMITTER: Kusz N

PROVIDER: S-EPMC7918049 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Juncaceae Species as Promising Sources of Phenanthrenes: Antiproliferative Compounds from Juncus maritimus Lam.

Kúsz Norbert N Stefkó Dóra D Barta Anita A Kincses Annamária A Szemerédi Nikoletta N Spengler Gabriella G Hohmann Judit J Vasas Andrea A

Molecules (Basel, Switzerland) 20210213 4

Juncaceae family represents an abundant source of phenanthrenes. In continuation of our work aiming at the isolation of biologically active compounds from Juncaceae species, Juncus maritimus Lam. was subjected to phytochemical and pharmacological investigations. The isolation process was carried out by using combined extraction and chromatographic methods. The structures of the obtained chemical compounds were elucidated by spectroscopic analysis, including HRESIMS, 1D (1H, <su ...[more]

PMID: 33668621

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Project description:Bioactive lipophilic compounds were investigated in 14 leguminous tree species of timber, agroforestry, medicinal or ornamental use but little industrial significance to elucidate their potential in food additive and supplement production. The tree species investigated were: Acacia auriculiformis, Acacia concinna, Albizia lebbeck, Albizia odoratissima, Bauhinia racemosa, Cassia fistula, Dalbergia latifolia, Delonix regia, Entada phaseoloides, Hardwickia binata, Peltophorum pterocarpum, Senegalia catechu, Sesbania sesban and Vachellia nilotica. The hexane-extracted oils of ripe seeds were chromatographically analysed for their fatty acid composition (GC-MS), tocochromanol (RP-HPLC/FLD), squalene and sterol (GC-FID) content. A spectrophotometrical method was used to determine total carotenoid content. The results showed generally low oil yield (1.75-17.53%); the highest was from H. binata. Linoleic acid constituted the largest proportion in all samples (40.78 to 62.28% of total fatty acids), followed by oleic (14.57-34.30%) and palmitic (5.14-23.04%) acid. The total tocochromanol content ranged from 100.3 to 367.6 mg 100 g-1 oil. D. regia was the richest and the only to contain significant amount of tocotrienols while other oils contained almost exclusively tocopherols, dominated by either α-tocopherol or γ-tocopherol. The total carotenoid content was highest in A. auriculiformis (23.77 mg 100 g-1), S. sesban (23.57 mg 100 g-1) and A. odoratissima (20.37 mg 100 g-1), and ranged from 0.7 to 23.7 mg 100 g-1 oil. The total sterol content ranged from 240.84 to 2543 mg 100 g-1; A. concinna seed oil was the richest by a wide margin; however, its oil yield was very low (1.75%). Either β-sitosterol or Δ5-stigmasterol dominated the sterol fraction. Only C. fistula oil contained a significant amount of squalene (303.1 mg 100 g-1) but was limited by the low oil yield as an industrial source of squalene. In conclusion, A. auriculiformis seeds may hold potential for the production of carotenoid-rich oil, and H. binata seed oil has relatively high yield and tocopherol content, marking it as a potential source of these compounds.

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Juncaceae Species as Promising Sources of Phenanthrenes: Antiproliferative Compounds from Juncus maritimus Lam.

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Juncaceae Species as Promising Sources of Phenanthrenes: Antiproliferative Compounds from <i>Juncus maritimus</i> Lam.

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