| Reference | [1]. J BUON. 2018 Jul-Aug;23(4):1163-1168.<br />
Picrocrocin exhibits growth inhibitory effects against SKMEL- 2 human malignant melanoma cells by targeting JAK/ STAT5 signaling pathway, cell cycle arrest and mitochondrial mediated apoptosis.<br />
Yu L(1), Li J, Xiao M.<br />
Author information: (1)Department of Dermatology of Shanghai Eighth People's Hospital, Shanghai 200235, China.<br />
PURPOSE: Melanoma is one of the lethal types of skin malignancies and is responsible for significant morbidity and mortality across the globe. In this study the anticancer effects of picrocrocin on the human SK-MEL-2 malignant melanoma cell line were evaluated along with its mode of action. METHODS: The effect of picrocrocin was evaluated on SKMEL- 2 cells by MTT assay. Apoptosis was determined by DAPI and annexin V/PI staining. The effects on reactive oxygen species (ROS), mitochondrial membrane potential (MMP) and cell cycle analysis were performed by flow cytometry. Expression of the proteins (JAK/STAT5) was estimated by western blotting. RESULTS: Picrocrocin exerted growth inhibitory effects on the SK-MEL-2 melanoma cells. The IC50 of picrocrocin against the SK-MEL-2 cells was 20 μM at 24-h incubation. The antiproliferative activity of picrocrocin was due to apoptosis and cell cycle arrest. In addition, picrocrocin enhanced the ROS levels and decreased the MMP levels of SK-MEL-2 cells. Finally, picrocrocin inhibited the JAK/STAT5 signalling pathway in the SK-MEL-2 melanoma cells. CONCLUSIONS: Taken together, these results indicate that picrocrocin can prove to be an important molecule in the search of more efficient therapies for melanoma.<br />
PMID: 30358226 [Indexed for MEDLINE]<br />
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[2]. J Agric Food Chem. 2011 Jan 12;59(1):249-55. doi: 10.1021/jf102828v. Epub 2010 Dec 8.<br />
Picrocrocin kinetics in aqueous saffron spice extracts (Crocus sativus L.) upon thermal treatment.<br />
Sánchez AM(1), Carmona M, Jarén-Galán M, Mosquera MI, Alonso GL.<br />
Author information: (1)Cátedra de Química Agrícola, ETSI Agrónomos de Albacete, Universidad de Castilla-La Mancha, Albacete, Spain.<br />
The kinetics of picrocrocin degradation in aqueous extracts of saffron upon thermal treatment from 5 to 70 °C have been studied, together with the degradation of purified picrocrocin in water at 100 °C. The best fits to experimental data were found for a second-order kinetics model. Picrocrocin showed high stability with half-life periods (t(1/2)) ranging from >3400 h at 5 °C in saffron extracts to 9 h in the experiments with purified picrocrocin at 100 °C. In saffron extracts, the evolution of the rate constant (k) with temperature showed maximum values at 35 °C, and filtration of the extracts contributed to picrocrocin stability. In the case of purified picrocrocin, the generation of safranal in the first 5 h (yield up to 7.4%) was confirmed. Spectrometric parameters used in saffron quality control (E(1cm)(1%) 257 nm and ΔΕ(pic)) were not appropriate for documenting the evolution of picrocrocin.<br />
DOI: 10.1021/jf102828v PMID: 21141822 [Indexed for MEDLINE]<br />
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[3]. New Phytol. 2019 Oct;224(2):725-740. doi: 10.1111/nph.16079. Epub 2019 Aug 29.<br />
UGT709G1: a novel uridine diphosphate glycosyltransferase involved in the biosynthesis of picrocrocin, the precursor of safranal in saffron (Crocus sativus).<br />
Diretto G(1), Ahrazem O(2), Rubio-Moraga Á(2), Fiore A(1), Sevi F(1), Argandoña J(2), Gómez-Gómez L(2).<br />
Author information: (1)Italian National Agency for New Technologies, Energy, and Sustainable Development, Casaccia Research Centre, 00123, Rome, Italy. (2)Instituto Botánico, Departamento de Ciencia y Tecnología Agroforestal y Genética, Universidad de Castilla-La Mancha, Campus Universitario s/n, 02071, Albacete, Spain.<br />
Saffron, a spice derived from the dried red stigmas of Crocus sativus, is one of the oldest natural food additives. The flowers have long red stigmas, which store significant quantities of the glycosylated apocarotenoids crocins and picrocrocin. The apocarotenoid biosynthetic pathway in saffron starts with the oxidative cleavage of zeaxanthin, from which crocins and picrocrocin are derived. In the processed stigmas, picrocrocin is converted to safranal, giving saffron its typical aroma. By a targeted search for differentially expressed uridine diphosphate glycosyltransferases (UGTs) in Crocus transcriptomes, a novel apocarotenoid glucosyltransferase (UGT709G1) from saffron was identified. Biochemical analyses revealed that UGT709G1 showed a high catalytic efficiency toward 2,6,6-trimethyl-4-hydroxy-1-carboxaldehyde-1-cyclohexene (HTCC), making it suited for the biosynthesis of picrocrocin, the precursor of safranal. The role of UGT709G1 in picrocrocin/safranal biosynthesis was supported by the absence or presence of gene expression in a screening for HTCC and picrocrocin production in different Crocus species and by a combined transient expression assay with CsCCD2L in Nicotiana benthamiana leaves. The identification of UGT709G1 completes one of the most highly valued specialized metabolic biosynthetic pathways in plants and provides novel perspectives on the industrial production of picrocrocin to be used as a flavor additive or as a pharmacological constituent.<br />
DOI: 10.1111/nph.16079 PMID: 31356694 [Indexed for MEDLINE]<br />
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[4]. Metab Eng. 2020 Sep;61:238-250. doi: 10.1016/j.ymben.2020.06.009. Epub 2020 Jul 3.<br />
Efficient production of saffron crocins and picrocrocin in Nicotiana benthamiana using a virus-driven system.<br />
Martí M(1), Diretto G(2), Aragonés V(1), Frusciante S(2), Ahrazem O(3), Gómez-Gómez L(4), Daròs JA(5).<br />
Author information: (1)Instituto de Biología Molecular y Celular de Plantas (Consejo Superior de Investigaciones Científicas-Universitat Politècnica de València), 46022, Valencia, Spain. (2)Italian National Agency for New Technologies, Energy, and Sustainable Development, Casaccia Research Centre, 00123, Rome, Italy. (3)Instituto Botánico, Departamento de Ciencia y Tecnología Agroforestal y Genética, Facultad de Farmacia, Universidad de Castilla-La Mancha, Campus Universitario S/n, 02071, Albacete, Spain. (4)Instituto Botánico, Departamento de Ciencia y Tecnología Agroforestal y Genética, Facultad de Farmacia, Universidad de Castilla-La Mancha, Campus Universitario S/n, 02071, Albacete, Spain. Electronic address: [email protected]. (5)Instituto de Biología Molecular y Celular de Plantas (Consejo Superior de Investigaciones Científicas-Universitat Politècnica de València), 46022, Valencia, Spain. Electronic address: [email protected].<br />
Crocins and picrocrocin are glycosylated apocarotenoids responsible, respectively, for the color and the unique taste of the saffron spice, known as red gold due to its high price. Several studies have also shown the health-promoting properties of these compounds. However, their high costs hamper the wide use of these metabolites in the pharmaceutical sector. We have developed a virus-driven system to produce remarkable amounts of crocins and picrocrocin in adult Nicotiana benthamiana plants in only two weeks. The system consists of viral clones derived from tobacco etch potyvirus that express specific carotenoid cleavage dioxygenase (CCD) enzymes from Crocus sativus and Buddleja davidii. Metabolic analyses of infected tissues demonstrated that the sole virus-driven expression of C. sativus CsCCD2L or B. davidii BdCCD4.1 resulted in the production of crocins, picrocrocin and safranal. Using the recombinant virus that expressed CsCCD2L, accumulations of 0.2% of crocins and 0.8% of picrocrocin in leaf dry weight were reached in only two weeks. In an attempt to improve apocarotenoid content in N. benthamiana, co-expression of CsCCD2L with other carotenogenic enzymes, such as Pantoea ananatis phytoene synthase (PaCrtB) and saffron β-carotene hydroxylase 2 (BCH2), was performed using the same viral system. This combinatorial approach led to an additional crocin increase up to 0.35% in leaves in which CsCCD2L and PaCrtB were co-expressed. Considering that saffron apocarotenoids are costly harvested from flower stigma once a year, and that Buddleja spp. flowers accumulate lower amounts, this system may be an attractive alternative for the sustainable production of these appreciated metabolites.<br />
DOI: 10.1016/j.ymben.2020.06.009 PMID: 32629020 [Indexed for MEDLINE]<br />
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[5]. J Food Sci. 2016 Jan;81(1):S189-98. doi: 10.1111/1750-3841.13152. Epub 2015 Nov 25.<br />
Sensory Threshold Studies of Picrocrocin, the Major Bitter Compound of Saffron.<br />
Chrysanthou A(1), Pouliou E(1), Kyriakoudi A(1), Tsimidou MZ(1).<br />
Author information: (1)Laboratory of Food Chemistry and Technology, School of Chemistry, Aristotle Univ. of Thessaloniki, 54124, Thessaloniki, Greece.<br />
This study is part of a wider project on the bitter taste of saffron and its preparations. A deeper knowledge on the taste perception of picrocrocin is necessary in order to develop products that satisfy consumer senses and provide them with adequate amounts of saffron major constituents, also appreciated for bioactivity. A systematic approach on the bitterness of picrocrocin, the major responsible compound, was conducted. A panel was trained specifically for the determination of taste detection and recognition thresholds of picrocrocin, which were found to be 5.34 and 7.26 mg/L, respectively, using the Ascending Forced Choice of Limits methodology. The threshold values were examined in water in absence and presence of other saffron constituents and ethanol and were found to decrease when served hot (61 ± 4 °C). Bitterness was enhanced in 40% (v/v) aqueous ethanol. In both aqueous and ethanol extracts, the presence of saffron volatiles improved bitterness perception. The usefulness of the study was tested in the case of commercial saffron based infusions.<br />
DOI: 10.1111/1750-3841.13152 PMID: 26605534 [Indexed for MEDLINE]
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