Coumarins ofFerula penninervis

Ermatov, N. E.; Ban'kovskii, A. I.; Perel'son, M. E.

doi:10.1007/bf01134229

Cited by 2 publications

(6 citation statements)

References 3 publications

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“…ESI-Q-TOF-MS data were recorded in positive mode; 100-1700 m/z mass range; 325 • C gas temperature; 12 L/min nitrogen flow; 30 psi nebulizer pressure; 65 V skimmer; 3500 V capillary voltage; 140 V fragmentor; 20 V collision energy. Full structural characterization was achieved in CD 3 OD by 1D NMR ( 1 H-NMR; 13 C-DEPTQ-NMR) and 2D NMR (correlation spectroscopy, COSY; heteronuclear multiple-bond correlation, HMBC; multiplicity-edited heteronuclear single-quantum correlation, edited-HSQC; rotating-frame Overhauser enhancement spectroscopy, ROESY) spectroscopic experiments. LNCaP, PNT2 and N87 cells were grown in RPMI-1640 medium; PC3 cells were cultured in Ham's F12; DU145, Caco-2 and BJ cells were maintained in EMEM.…”

Section: Structure Elucidationmentioning

confidence: 99%

“…(syn. Ferula olgae Regel & Schmalh., feather-veined giant fennel) is a perennial herbaceous plant species spread in the dry and hot regions of Central Asia [ 13 ]. In Kazakh traditional folk medicine, the roots are used internally (decocts) or externally (tinctures, compresses) to treat epilepsy, neurosis, rheumatism and various inflammatory diseases, gastroduodenal ulcers, dyspepsia, wounds, abscesses and tumours [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

“…UV (methanol) λ max 254 nm; HREIMS m/z 391.1773 [M + H] + (calcd for C 21 H 27 O 7 + , ∆ = -5.62 ppm); HRMS/MS(+) m/z 331.1561, 303.1242, 261.1134, 243.1031, 215.1072 1. H NMR (CD 3 OD, 600 MHz) δ 1.21 (3H, d, J = 7.0 Hz, H-8d), 1.24 (3H, d, J = 7.0 Hz, H-8c), 1.61 (3H, s, H-13), 2.10 (3H, s, H-11b), 2.25 (3H, s, H-14), 2.25 (3H, s, H-15), 2.61 (1H, hept, J = 7.0 Hz, H-8b), 2.65 (1H, dd, J = 19.1, 10.9 Hz, H-9 ), 2.79 (1H, dd, J = 19.1, 3.3 Hz, H-9 ), 3.63 (1H, dd, J = 10.9, 9.7 Hz, H-7), 3.94 (1H, d, J = 11.4 Hz, H-5), 4.69 (1H, t, J = 11.4, 9.7 Hz, H-6), 5.60 (1H, td, J = 10.9, 3.3 Hz, H-8), 6.19 (1H, s, H-3);13 C NMR (CD 3 OD, 151 MHz) δ 19.0 (C-8d), 19.3 (C-8c), 20.2 (C-15), 20.3 (C-14), 20.7 (C-13), 20.7 (C-11b), 35.4 (C-8b), 44.4 (C-9), 48.5 (C-7), 48.8 (C-5), 68.7 (C-8), 79.4 (C-11), 80.2 (C-6), 130.6 (C-1), 136.3 (C-3), 147.7 (C-10), 171.3 (C-11a), 173.1 (C-4), 175.6 (C-12), 177.3 (C-8a), 197.6 (C-2). Compound 3: UV (methanol) λ max 253 nm; HREIMS m/z 403.1773 [M + H] + (calcd for C 22 H 27 O 7 + , ∆ = -5.40 ppm); HRMS/MS(+) m/z 343.1609, 321.1403, 303.1287, 261.1174, 243.1065.…”

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confidence: 99%

“…1 H NMR (600 MHz) and13 C NMR (151 MHz) data of ferupennin P (2) and ferupennin Q (6) in CD 3 OD; δ in ppm; J in Hz.…”

mentioning

confidence: 99%

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Liquid-Liquid Chromatography Separation of Guaiane-Type Sesquiterpene Lactones from Ferula penninervis Regel & Schmalh. and Evaluation of Their In Vitro Cytotoxic and Melanin Inhibitory Potential

Luca

Gaweł-Bęben

Strzępek-Gomółka

et al. 2021

IJMS

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Ferula penninervis Regel & Schmalh. is a perennial plant used in Kazakh traditional folk medicine to treat epilepsy, neurosis, rheumatism, gastroduodenal ulcers, dyspepsia, wounds, abscesses or tumors. The aim of this work was to isolate series of sesquiterpene lactones from a crude methanolic root extract and investigate their in vitro cytotoxic potential against androgen-dependent prostate cancer LNCaP and epithelial prostate PNT2 cells, as well as to evaluate their melanin production inhibitory effects in murine melanoma B16F10 cells stimulated with α-melanocyte-stimulating hormone (αMSH). Two new (penninervin P and penninervin Q) and five known (olgin, laferin, olgoferin, oferin and daucoguainolactone F) guaiane-type sesquiterpene lactones were isolated with the use of a simple and fast liquid-liquid chromatography method. Olgin and laferin showed the most promising cytotoxic effects in LNCaP cells (IC50 of 31.03 and 23.26 μg/mL, respectively). Additionally, olgin, laferin, olgoferin, and oferin (10 μg/mL) potently impaired melanin release (40.67–65.48% of αMSH + cells) without influencing the viability of B16F10 cells. In summary, our findings might indicate that guaiane-type sesquiterpene lactones from F. penninervis could be regarded as promising candidates for further research in discovering new therapeutic agents with anti-prostate cancer and skin depigmentation properties.

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Section: Structure Elucidationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

“…1 H NMR (600 MHz) and13 C NMR (151 MHz) data of ferupennin P (2) and ferupennin Q (6) in CD 3 OD; δ in ppm; J in Hz.…”

mentioning

confidence: 99%

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Liquid-Liquid Chromatography Separation of Guaiane-Type Sesquiterpene Lactones from Ferula penninervis Regel & Schmalh. and Evaluation of Their In Vitro Cytotoxic and Melanin Inhibitory Potential

Luca

Gaweł-Bęben

Strzępek-Gomółka

et al. 2021

IJMS

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“…For extraction of coumarins methanol and water, n-hexane, dichloromethane, ethyl acetate, and chloroform were used. The discovery of prenylated coumarins (5-8) was mentioned in the early works of Batirov et al, Nabiev et al,Ermatov et al,[17][18][19][20][21][22].…”

Section: Coumarinsmentioning

confidence: 99%

Coumarins of genus Ferula L. (Apiaceae Lindl.)

Khosnutdinova

Gemejiyeva

Karzhaubekova

et al. 2023

Eurasian Chem.-Technol. J.

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The biologically active coumarins from Ferula L. species of the family Apiaceae Lindl. for the period 1970 to 2022 have been reviewed. The phytochemical investigation of different parts of Ferula L., including gum resin, leaves, fruits, seeds, roots, rhizomes, and resins led to the separation of different types of coumarins. Nearly 185 coumarins were isolated from 35 species of Ferula L. growing in different countries. Coumarins are represented mainly by umbelliferone (7-O-hydroxycoumarin) derivatives substituted in the C-7 position of aglycone, furanocoumarins and metabolites have terpene fragments, esters and glycosides. Umbelliferon is found as a taxon for the genus Ferula L. Some «unusual» metabolites have a furan fragment attached to the pyrone ring. Coumarins are of the psoralen type, containing a furan ring in the C-6 and C-7 positions of the primary skeleton. The rare coumarins with terpene fragments (hemiterpene, monoterpen, sesquiterpene) were reported. The biological activities of some extracts and individual metabolites such as antiinflammatory, cytotoxicity, antibacterial, antileishmanial, antiviral, antigenotoxic, antitumor, anticoagulant, antioxidant, antimycobacterial, inhibition a-glucosidase, antileishmanial were found.

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Coumarins ofFerula penninervis

Cited by 2 publications

References 3 publications

Liquid-Liquid Chromatography Separation of Guaiane-Type Sesquiterpene Lactones from Ferula penninervis Regel & Schmalh. and Evaluation of Their In Vitro Cytotoxic and Melanin Inhibitory Potential

Liquid-Liquid Chromatography Separation of Guaiane-Type Sesquiterpene Lactones from Ferula penninervis Regel & Schmalh. and Evaluation of Their In Vitro Cytotoxic and Melanin Inhibitory Potential

Coumarins of genus Ferula L. (Apiaceae Lindl.)

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