Sesquiterpene Lactones from the Roots of Ferula varia and Their Cytotoxic Activity

Suzuki, Kyoko; Okasaka, Mamoru; Kashiwada, Yoshiki; Takaishi, Yoshihisa; Honda, Gisho; Ito, Michiho; Takeda, Yoshio; Khojimatov, Olim K.; Ashurmetov, Ozodbek; Sekiya, Michiko; Ikeshiro, Yasumasa

doi:10.1021/np0703996

Cited by 44 publications

(31 citation statements)

References 17 publications

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“…The 1 H-and 13 C-NMR spectra showed the signals due to two tert-methyl groups, two vinyl methyl groups, two methylenes, two methines, four oxygen-bearing methines, one quaternary carbon, one oxygen-bearing quaternary carbon, one exo-methylene, one sp 2 methine, two sp 2 quaternary carbons, two carbonyl carbons, and a glucosyl moiety. The data for the aglycone moiety were similar to those of a eudesmane-type sesquiterpene lactone with an angeloyl group (1β-angeloyloxy-11β-hydroxy-5βH,6αH,7αH,10α-methyleudesm-2(3),5(15)-diene-6,12-olide, I) previously isolated from the EtOAc-soluble fraction of this plant, 3) except for the observation of the signals due to two additional oxygenbearing methines and a sugar moiety, as well as the absence of a disubstituted olefinic signal. The existence of the eudesmane-type sesquiterpene lactone structure with three oxygen-bearing functions and an angeloyl group was also supported by 2D-NMR spectral analysis.…”

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confidence: 73%

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Sesquiterpene Lactone Glycosides from the Roots of Ferula varia

Kurimoto

Suzuki

Okasaka

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Seven new sesquiterpene lactone glycosides (1-7) were isolated from the H 2 O-soluble fraction from the MeOH extract of the roots of Ferula varia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of compounds 1 and 2 were determined by modified Mosher's method.Key words Ferula varia; sesquiterpene lactone glycoside; Umbelliferae; UzbekistanWe have been investigating medicinal plants of Uzbekistan in search of new drug leads.

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“…The molecular formula of 6 was established as C 26 H 38 O 13 by HR-ESI-MS. The 1 H and 13 C NMR spectra were correlated with those of I, 3) except for the observation of signals due to two sugar moieties and the absence of signals arising from an angeloyl group. The two sugar moieties were confirmed as glucose and apiose by acid hydrolysis of 6.…”

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confidence: 96%

Sesquiterpene Lactone Glycosides from the Roots of Ferula varia

Kurimoto

Suzuki

Okasaka

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…We have been investigating the herbal medicines of Uzbekistan with the aim of searching for novel drug leads (Umbelliferae [1][2][3][4][5][6][7][8][9][10], Compositae [11][12][13][14], Guttiferae [15,16], Polygonaceae [17], Cupressaceae [18], Paeoniaceae [19]). The aerial parts of Mediasia macrophylla (Umbelliferae) have been used traditionally as a perfume; an appetite enhancer; a natural preservative; and for treatment of rheumatism, nephritis, eczema, herpes, and injury [20].…”

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confidence: 99%

Four new glucosides from the aerial parts of Mediasia macrophylla

et al. 2010

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As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1'S)-(4-hydroxyphenyl) ethane-1',2'-diol 2'-O-β-glucopyranoside (1), 3-(4'-methoxyphenyl)-propanol 1-O-β-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-β-glucopyranoside (3), 1-O-angeloyl-β-glucopyranose (4), on the basis of spectral analysis.

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“…[9][10][11] Recent pharmacological research has demonstrated that different extracts of Ferula species contain sesquiterpene derivatives that have in particular proven to be cytotoxic on several cancer cell lines. 2,12 In addition, the extracts have been reported to have antimicrobial, anthelmintic, anticonvulsant, antispasmodic, antihyperglycemic, antihyperlipidemic, and antioxidant activities. [13][14][15][16][17][18]…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity of Sesquiterpenoids Isolated from Endemic Ferula tenuissima Hub.-Mor & Peşmen

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2019

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Amaç: Endemik Ferula tenuissima köklerinin fitokimyasal yönden incelenmesi ve elde edilen saf bileşiklerin PC-3 üzerinde sitotoksik etkilerinin belirlenmesidir. Gereç ve Yöntemler: F. tenuissima 'nın açık havada kurutulmuş ve toz haline getirilmiş kökleri (1 kg, 24 saat boyunca 30°C'de sonikasyonda n-hexane, kloroform (CHCl 3) ve metanol (MeOH) (3×2 L, her biri) ile sırasıyla ekstre edilmiştir. Ekstraktlar daha sonra süzülmüştür. Sıvı ekstreler, vakum altında kuruluğa kadar uçurulmuştur. Kromatografik yöntemler ile bileşikler elde edilmiş ve bileşiklerin yapıları spektral yöntemler ile belirlinmiştir (1D-, 2D NMR ve LC-MS). Bileşiklerin PC-3 üzerindeki sitotoksik aktiviteleri WST yöntemi ile test edilmiştir. Bulgular: Endemik F. tenuissima'nın kurutulmuş köklerinin fitokimyasal incelemesi yapılmış ve üç seskiterpen esteri izole edilmiştir. Teferidin, ferutinin ve elaeochytrin-A daukan tip seskiterpen esterleri olarak belirlenmiştir. Biyoaktivite çalışmasında, ferutinin en yüksek sitotoksik aktiviteyi IC 50 : 19.7 µM ile göstermiştir. Sonuç: F. tenuissima köklerinin ana bileşiklerinin daukan seskiterpenler ve ferutininin PC-3 hücreleri üzerinde potansiyel bir etkiye sahip olduğunu göstermektedir. Anahtar kelimeler: Ferula tenuissima, daukan seskiterpen ester, sitotoksite, prostat kanseri Objectives: This was a phytochemical study of endemic Ferula tenuissima roots and determined the cytotoxic activity of pure compounds on PC-3. Materials and Methods: Air-dried and powdered roots of F. tenuissima (1 kg) were extracted consecutively with n-hexane, chloroform (CHCl 3), and methanol (MeOH) (3×2 L, each) by sonication at 30°C for 24 h. The extracts were then filtered. The solvents were separately evaporated under reduced pressure to dryness. The compounds were isolated by chromatographic methods and their structures were determined by spectral methods (1D and 2D NMR and LC-MS). The compounds were tested for their cytotoxic activities versus the PC-3 cell line by WST assay. Results: A phytochemical investigation of the dried roots of endemic F. tenuissima was performed and three sesquiterpene esters were isolated. The daucane-type sesquiterpenes teferidin, ferutinin, and elaeochytrin-A were identified. In the bioactivity study, ferutinin exhibited the highest cytotoxic activity, with an IC 50 value of 19.7 µM. Conclusion: The results indicate that the main compounds of F. tenuissima roots are daucane sesquiterpenes and ferutinin has a potential effect on PC-3 cells.

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Sesquiterpene Lactones from the Roots of Ferula varia and Their Cytotoxic Activity

Cited by 44 publications

References 17 publications

Sesquiterpene Lactone Glycosides from the Roots of <i>Ferula varia</i>

Sesquiterpene Lactone Glycosides from the Roots of <i>Ferula varia</i>

Four new glucosides from the aerial parts of Mediasia macrophylla

Cytotoxic Activity of Sesquiterpenoids Isolated from Endemic <i>Ferula tenuissima</i> Hub.-Mor & Peşmen

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