Sesquiterpene Lactones from <i>Daucus glaber</i>

Sallam, Amal; Hitotsuyanagi, Yukio; Mansour, El-Sayed S.; Ahmed, Atallah F.; Gedara, Sahar R.; Fukaya, Haruhiko; Takeya, Koichi

doi:10.1002/hlca.200900126

Cited by 10 publications

(9 citation statements)

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“…Two new and five known guaiane-type sesquiterpene lactones ( Figure 3 and Figure S1 ) were isolated from F. penninervis methanolic root extract. The known compounds were identified as olgin ( 1 ), laferin ( 3 ), olgoferin ( 4 ), oferin (5 ) and daucoguainolactone F ( 7 ) by comparing their spectral data with those reported in spectral libraries and literature [ 15 , 27 , 28 ].…”

Section: Resultsmentioning

confidence: 99%

“…Two new and five known guaiane-type sesquiterpene lactones (Figures 3 and S1) were isolated from F. penninervis methanolic root extract. The known compounds were identified as olgin (1), laferin (3), olgoferin (4), oferin (5) and daucoguainolactone F ( 7) by comparing their spectral data with those reported in spectral libraries and literature [15,27,28]. ) and from H-6 at δH 4.69 (1H, t, J = 11.4, 9.7 Hz, H-6) to H-7 at δH 3.63 (1H, dd, J = 10.9, 9.7 Hz, H-7) indicated that the relative configuration was the same than olgin.…”

Section: Structure Elucidation Of the New Guaiane-type Sesquiterpene Lactonesmentioning

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: Resultsmentioning

confidence: 99%

Section: Structure Elucidation Of the New Guaiane-type Sesquiterpene Lactonesmentioning

confidence: 99%

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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“…A wide range of pharmacologic properties such as antibacterial, antifungal, anthelmintic, hepatoprotective and cytotoxic activities have been reported on D. carota [ 2 ]. Phytochemical studies indicated the presence of sesquiterpenes, chromones, flavonoids, coumarins and anthocyanins from D. carota [ 2 ], sesquiterpene lactone [ 3 ] and phenylpropanoid triesters [ 4 ] from D. glaber (Forssk.) Thell.…”

Section: Introductionmentioning

confidence: 99%

Bioactive Terpenoids and Flavonoids from Daucus littoralis Smith subsp. hyrcanicus Rech.f, an Endemic Species of Iran

et al. 2014

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BackgroundDaucus littoralis Smith subsp. hyrcanicus Rech.f. (Apiaceae) is an endemic species in northern parts of Iran where it is commonly named Caspian carrot. The fruits have been used as condiment.MethodsIn a series of in vitro assays, antioxidant (DPPH and FRAP assays), cytotoxic and antimicrobial activities of different extracts of roots and fruits were evaluated for the first time. The separation and purification of the compounds were carried out on the most potent extracts using various chromatographic methods and identified by spectroscopic data (1H and 13C NMR).ResultsThe results showed that among the extracts only fruit methanol extract (FME) has significant antioxidant activity (IC50 = 145.93 μg.ml-1 in DPPH assay and 358 ± 0.02 mmol FeII/g dry extract in FRAP assay). The radical scavenging activity of FME at 400 μg.ml-1 was comparable with α-tocopherol (40 μg.ml-1) and with BHA (100 μg.ml-1) (p > 0.05). FME did not show any toxicity against cancerous and normal cell lines. Fruit ethyl acetate extract (FEE) had cytotoxic activity against breast carcinoma and hepatocellular carcinoma cells (IC50 168.4 and 185 μg.ml-1, respectively), while it did not possess antioxidant activity in comparison with α-tocopherol and BHA as standard compounds. Ethyl acetate and methanol extract of fruits showed antimicrobial activity against Staphylococcus aureus (MIC: 3.75 mg.ml-1) and Candida albicans (MIC: 15.6 and 7.8 mg.ml-1, respectively). Four terpenoids were isolated form FEE including: β-sitosterol (1), stigmasterol (2), caryophyllene oxide (3), β-amyrin (4). Also, three flavonoids namely quercetin 3-O-β-glucoside (5), quercetin 3-O-β-galactoside (6) and luteolin (7) were isolated from FME.ConclusionThis study showed that FEE and FME of D. littoralis Smith subsp. hyrcanicus Rech.f. had the highest biological activities which may be correlated with in vitro cytotoxic, antimicrobial and antioxidant activities of terpenoids and flavonoids components of the extracts.

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“…Daucus carota [ 100 ]. Salam et al identified six new sesquiterpene lactone esters; daucoguaianolactones A–F ( 131 – 136 ), and one new sesquiterpene lactone; daucoeudesmanolactone A ( 137 ) from the leaves and stems of Daucus glaber [ 101 ], along with the known sesquiterpene lactones talasins A and B and badkhysin. Bioactivity assessment showed that compounds 134 , 137 , and talasins A and B showed moderate cytotoxicity against P-388 leukemia cells [ 101 ].…”

Section: Ulvaceae Umbelliferae and Urticaceaementioning

confidence: 99%

“…Salam et al identified six new sesquiterpene lactone esters; daucoguaianolactones A–F ( 131 – 136 ), and one new sesquiterpene lactone; daucoeudesmanolactone A ( 137 ) from the leaves and stems of Daucus glaber [ 101 ], along with the known sesquiterpene lactones talasins A and B and badkhysin. Bioactivity assessment showed that compounds 134 , 137 , and talasins A and B showed moderate cytotoxicity against P-388 leukemia cells [ 101 ]. From the leaves and stems of the same species, Sallam et al also isolated three new phenylpropanoid triesters, glaberins A–C ( 138 – 140 ), compounds 138 and 139 showing cytotoxicity against P-388 murine lymphocytic leukemia cells with respective IC 50 values of 55 and 44 µg/mL [ 102 ].…”

Section: Ulvaceae Umbelliferae and Urticaceaementioning

confidence: 99%

The Chemistry and Biological Activities of Natural Products from Northern African Plant Families: From Taccaceae to Zygophyllaceae

Ntie‐Kang

Njume

Malange

et al. 2016

Nat. Prod. Bioprospect.

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Traditional medicinal practices have a profound influence on the daily lives of people living in developing countries, particularly in Africa, since the populations cannot generally afford the cost of Western medicines. We have undertaken to investigate the correlation between the uses of plants in Traditional African medicine and the biological activities of the derived natural products, with the aim to validate the use of traditional medicine in Northern African communities. The literature is covered for the period 1959–2015 and part III of this review series focuses on plant families with names beginning with letters T to Z. The authors have focused on curating data from journals in natural products and phytomedicine. Within each journal home page, a query search based on country name was conducted. All articles “hits” were then verified, one at a time, that the species was harvested within the Northern African geographical regions. The current data partly constitutes the bases for the development of the Northern African natural compounds database. The review discusses 284 plant-based natural compounds from 34 species and 11 families. It was observed that the ethnobotanical uses of less than 40 % of the plant species surveyed correlated with the bioactivities of compounds identified.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0091-9) contains supplementary material, which is available to authorized users.

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Sesquiterpene Lactones from Daucus glaber

Cited by 10 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

Bioactive Terpenoids and Flavonoids from Daucus littoralis Smith subsp. hyrcanicus Rech.f, an Endemic Species of Iran

The Chemistry and Biological Activities of Natural Products from Northern African Plant Families: From Taccaceae to Zygophyllaceae

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