3,5-Nonadiyne Isolated from the Rhizome of Cachrys ferulacea Inhibits Endogenous Nitric Oxide Release by Rat Peritoneal Macrophages

Dokovic, Dejan; Bulatovic, Vanja M.; Božić, Biljana; Kataranovski, Milena; Zrakić, Tomislav M.; Kovačević, Nada

doi:10.1248/cpb.52.853

Cited by 25 publications

(19 citation statements)

References 9 publications

(7 reference statements)

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“…Most of the Prangos species are reported to possess diverse pharmacological activities viz. anti-microbial [1] , anti-oxidant [2] , cytotoxic [3] , [4] , anti-helmintic and aphrodisiac [5] , besides, their use in the treatment of haemorrhoids, wounds and leukoplakia [6] . In Central Asia, the extracts of Prangos species have been used to stop bleeding and heal scars [4] .…”

Section: Introductionmentioning

confidence: 99%

Isolation, Cytotoxicity Evaluation and HPLC-Quantification of the Chemical Constituents from Prangos pabularia

et al. 2014

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Phytochemical analysis of the dichloromethane:methanol (1∶1) extract of root parts of Prangos pabularia led to the isolation of twelve cytotoxic constituents, viz., 6-hydroxycoumarin (1), 7-hydroxycoumarin (2), heraclenol-glycoside (3), xanthotoxol (4), heraclenol (5), oxypeucedanin hydrate (6), 8-((3,3-dimethyloxiran-2-yl)methyl)-7-methoxy-2H-chromen-2-one (7), oxypeucedanin hydrate monoacetate (8), xanthotoxin (9), 4-((2-hydroxy-3-methylbut-3-en-1-yl)oxy)-7H-furo[3,2-g]chromen-7-one (10), imperatorin (11) and osthol (12). The isolates were identified using spectral techniques in the light of literature. 3-(4,5-dimethyl thiazol-2yl)-2,5-diphenyltetrazolium bromide (MTT) cytotoxicity screening of the isolated constituents was carried out against six human cancer cell lines including lung (A549 and NCI-H322), epidermoid carcinoma (A431), melanoma (A375), prostate (PC-3) and Colon (HCT-116) cell lines. Osthol (12) exhibited the highest cytotoxicity with IC50 values of 3.2, 6.2, 10.9, 14.5, 24.8, and 30.2 µM against epidermoid carcinoma (A431), melanoma (A375), lung (NCI-H322), lung (A549), prostate (PC-3) and colon (HCT-116) cell lines respectively. Epidermoid carcinoma cell line A431 was sensitive to most of the compounds followed by lung (A549) cancer cell line. Finally a simple and reliable HPLC method was developed (RP-HPLC-DAD) and validated for the simultaneous quantification of these cytotoxic constituents in Prangos pabularia. The extract was analyzed using a reversed-phase Agilent ZORBAX eclipse plus column C18 (4.6×250 mm, 5 µm) at 250 nm wavelength using a gradient water-methanol solvent system at a flow rate of 0.8 ml/min. The RP-HPLC method is validated in terms of recovery, linearity, accuracy and precision (intra and inter-day validation). This method, because of shorter analysis time, makes it valuable for the commercial quality control of Prangos pabularia extracts and its future pharmaceutical preparations.

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Section: Introductionmentioning

confidence: 99%

Isolation, Cytotoxicity Evaluation and HPLC-Quantification of the Chemical Constituents from Prangos pabularia

et al. 2014

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“…The flowers are followed by narrowly ellipsoid to globose fruits, which may possess five straight to plicate wings (Davis, 1989;Rechinger, 1987). Some members of the genus are popular as sedative, digestive, tonic and aphrodisiac herbs, and they have been used in the treatment of intestinal worms, haemorrhoids, leukoplakic disease and bleeding in different regions of central Asia, Caucasia and the Mediterranean for a long time (Dokovic et al, 2004;Shikishima et al, 2001;Ulubelen et al, 1995).…”

Section: Introductionmentioning

confidence: 99%

Chemical variation of the essential oil ofPrangos ulopteraDC. at different stages of growth

Razavi¹,

Nazemiyeh²,

Delazar³

et al. 2011

Natural Product Research

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In the current investigation, the influence of the plant growth stages (prior to emergence of flower heads or vegetative, anthesis and fruiting) on the essential oil content and composition in the aerial parts of Prangos uloptera DC. was studied. Quantitative and qualitative differences were found among oil of aerial parts at three phenological stages. The principle compounds of the oil before emergence of flower heads were saferole (21.6%) and α-pinene (20%), while the oil at anthesis was composed of α-bisabolol (30.5%), saferole (19.11%) and (+)-spathulenol (12.9%). The oil at fruiting stage displayed γ-terpinene (35.5%) and trans-anethole (23.5%) as major constituents. These findings may confer valuable information regarding chemical composition of P. uloptera DC., which could be beneficial in the fields of herbal medicine.

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“…The stem oil was characterized by 1,8-cineole (19.0 %) and α-pinene (10.3 %) [61]. The root oil was found to be rich in β-phellandrene (11.8-32.1 %) and δ-3-carene (22.5-25.8 %) [72,73] and 3,5-nonadiyne (85 %) [74]. The significant variability observed in the various studies can be mainly ascribed to differences in geographic origin (related, for example, to pedoclimatic factors), phenological stage, and genetics of the samples.…”

Section: Essential Oilsmentioning

confidence: 99%

“…3,5-Nonadiyne, isolated from the root essential oil of P. ferulacea collected in Montenegro, selectively inhibited the endogenous nitric oxide release in rat peritoneal macrophages (IC 50 = 6.7 µM) without inhibiting T cell proliferation [74].…”

Section: Other Propertiesmentioning

confidence: 99%

The Nonvolatile and Volatile Metabolites of Prangos ferulacea and Their Biological Properties

et al. 2019

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Prangos ferulacea (L.) Lindl. (Fam. Apiaceae), an orophilous species of eastern Mediterranean and western Asia, possesses a number of biological properties that are worthy of exploitation in different fields. Phytochemical investigations revealed the presence of coumarins, prenyl-coumarins, and furano-coumarins as the main constituents of this species, as well as several flavonoids. Among prenyl-coumarins, osthol is a promising apoptotic agent quite selective toward cancer cells. In addition, the essential oils have been extensively investigated, and several chemotypes have been identified. This work reviews the literature on this species published between 1965 and 2018, describes its volatile and nonvolatile metabolites, and outlines its pharmacological effects.

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3,5-Nonadiyne Isolated from the Rhizome of Cachrys ferulacea Inhibits Endogenous Nitric Oxide Release by Rat Peritoneal Macrophages

Cited by 25 publications

References 9 publications

Isolation, Cytotoxicity Evaluation and HPLC-Quantification of the Chemical Constituents from Prangos pabularia

Isolation, Cytotoxicity Evaluation and HPLC-Quantification of the Chemical Constituents from Prangos pabularia

Chemical variation of the essential oil ofPrangos ulopteraDC. at different stages of growth

The Nonvolatile and Volatile Metabolites of Prangos ferulacea and Their Biological Properties

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