Picrocrocin (BioDeep_00000000941)

 

Secondary id: BioDeep_00001867570

human metabolite PANOMIX_OTCML-2023 Antitumor activity natural product


代谢物信息卡片


(R)-2,6,6-trimethyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohex-1-ene-1-carbaldehyde

化学式: C16H26O7 (330.1678)
中文名称: 青霉素, 苦番紅花素
谱图信息: 最多检出来源 Viridiplantae(plant) 11.78%

分子结构信息

SMILES: CC1=C(C(CC(C1)OC2C(C(C(C(O2)CO)O)O)O)(C)C)C=O
InChI: InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/m1/s1

描述信息

Picrocrocin is a glycoside formed from glucose and safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste and is the chemical most responsible for the taste of saffron. It is believed that picrocrocin is a degradation product of the carotenoid zeaxanthin (Wikipedia).
Picrocrocin is a beta-D-glucoside of beta-cyclocitral; the precursor of safranal. It is the compound most responsible for the bitter taste of saffron. It is functionally related to a beta-cyclocitral.
Picrocrocin is a natural product found in Crocus tommasinianus, Crocus sativus, and Crocus vernus with data available.
Isolated from saffron (stamens of Crocus sativus). Food colour and flavouring ingredient
Picrocrocin, an apocarotenoid found in Saffron. Picrocrocin shows anticancer effect. Picrocrocin exhibits growth inhibitory effects against SKMEL-2 human malignant melanoma cells[1].
Picrocrocin, an apocarotenoid found in Saffron. Picrocrocin shows anticancer effect. Picrocrocin exhibits growth inhibitory effects against SKMEL-2 human malignant melanoma cells[1].

同义名列表

21 个代谢物同义名

(R)-2,6,6-trimethyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohex-1-ene-1-carbaldehyde; (R)-2,6,6-Trimethyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohex-1-enecarbaldehyde; (4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde; (4R)-2,6,6-trimethyl-4-{[(2R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde; (4R)-2,6,6-Trimethyl-4-[(2R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde; 1-Cyclohexene-1-carboxaldehyde, 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-, (4R)-; 1-Cyclohexene-1-carboxaldehyde, 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-, (R)-; 1-Cyclohexene-1-carboxaldehyde, 4-(ss-D-glucopyranosyloxy)-2,6,6-trimethyl-, (4R)-; (4R)-4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-CARBOXALDEHYDE; (R)-4-(beta-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde; 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde; (1R)-4-formyl-3,5,5-trimethylcyclohex-3-en-1-yl beta-D-glucopyranoside; PICROCROCIN [MI]; UNII-ON5B022511; saffron-bitter; Saffronbitter; Safranbitter; Picrocrocine; Picrocrocin; ON5B022511; Picrocrocin



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

7 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

31 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 12 AKT1, ANXA5, ARHGAP45, CASP3, EEF1A2, KEAP1, MAPK1, MARCKSL1, PTGS2, STAT5A, TBCE, TCIM
Peripheral membrane protein 2 ANXA5, PTGS2
Endoplasmic reticulum membrane 3 GUCY2C, HMOX1, PTGS2
Nucleus 11 AKT1, CASP3, EEF1A2, HMOX1, KEAP1, MAPK1, MMP2, MYB, NCOR2, STAT5A, TCIM
cytosol 10 AKT1, ANXA5, ARHGAP45, CASP3, HMOX1, KEAP1, MAPK1, MYB, STAT5A, TCIM
nuclear body 1 NCOR2
centrosome 1 MAPK1
nucleoplasm 10 AKT1, ATP2B1, CASP3, HMOX1, KEAP1, MAPK1, MYB, NCOR2, STAT5A, TCIM
RNA polymerase II transcription regulator complex 2 MYB, STAT5A
Cell membrane 5 AKT1, ATP2B1, GUCY2C, KCNH2, MARCKSL1
Lipid-anchor 1 MARCKSL1
Cytoplasmic side 1 HMOX1
lamellipodium 1 AKT1
ruffle membrane 1 ARHGAP45
Multi-pass membrane protein 2 ATP2B1, KCNH2
Synapse 3 ATP2B1, EEF1A2, MAPK1
cell cortex 1 AKT1
cell surface 1 KCNH2
glutamatergic synapse 3 AKT1, ATP2B1, CASP3
Golgi apparatus 1 MAPK1
neuronal cell body 1 CASP3
postsynapse 1 AKT1
presynaptic membrane 1 ATP2B1
sarcolemma 1 ANXA5
plasma membrane 9 AKT1, ARHGAP45, ATP2B1, GUCY2C, KCNH2, MAPK1, MARCKSL1, MMP2, TCIM
synaptic vesicle membrane 1 ATP2B1
Membrane 8 AKT1, ANXA5, ARHGAP45, ATP2B1, HMOX1, KCNH2, MYB, NCOR2
basolateral plasma membrane 1 ATP2B1
caveola 2 MAPK1, PTGS2
extracellular exosome 4 ANXA5, ATP2B1, MARCKSL1, MMP9
endoplasmic reticulum 3 HMOX1, KEAP1, PTGS2
extracellular space 3 HMOX1, MMP2, MMP9
perinuclear region of cytoplasm 2 HMOX1, KCNH2
mitochondrion 2 MAPK1, MMP2
protein-containing complex 2 AKT1, PTGS2
intracellular membrane-bounded organelle 1 ATP2B1
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 GUCY2C
extracellular region 5 ANXA5, ARHGAP45, MAPK1, MMP2, MMP9
mitochondrial outer membrane 1 HMOX1
centriolar satellite 1 KEAP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 ANXA5
Secreted, extracellular space, extracellular matrix 1 MMP9
microtubule cytoskeleton 1 AKT1
nucleolus 1 TCIM
midbody 1 KEAP1
Early endosome 1 MAPK1
cell-cell junction 1 AKT1
vesicle 1 AKT1
Cell projection, ruffle membrane 1 ARHGAP45
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton 2 MARCKSL1, TBCE
Cytoplasm, cytoskeleton, spindle 1 MAPK1
focal adhesion 2 ANXA5, MAPK1
microtubule 1 TBCE
spindle 2 AKT1, MAPK1
extracellular matrix 1 MMP2
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 3 ANXA5, MMP2, MMP9
lateral plasma membrane 1 ATP2B1
nuclear speck 1 TCIM
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK1
sarcomere 1 MMP2
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 2 NCOR2, STAT5A
cell projection 1 ATP2B1
mitotic spindle 1 MAPK1
cytoskeleton 2 MAPK1, MARCKSL1
Nucleus, nucleolus 1 TCIM
actin filament 1 KEAP1
Basolateral cell membrane 1 ATP2B1
Cul3-RING ubiquitin ligase complex 1 KEAP1
Membrane, caveola 1 MAPK1
monoatomic ion channel complex 1 KCNH2
Nucleus speckle 1 TCIM
Presynaptic cell membrane 1 ATP2B1
pseudopodium 1 MAPK1
inward rectifier potassium channel complex 1 KCNH2
voltage-gated potassium channel complex 1 KCNH2
ficolin-1-rich granule lumen 2 MAPK1, MMP9
secretory granule lumen 1 ARHGAP45
endoplasmic reticulum lumen 2 MAPK1, PTGS2
nuclear matrix 2 MYB, NCOR2
transcription repressor complex 1 NCOR2
tertiary granule lumen 1 MMP9
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
azurophil granule lumen 2 ARHGAP45, MAPK1
immunological synapse 1 ATP2B1
Single-pass type IV membrane protein 1 HMOX1
vesicle membrane 1 ANXA5
ribonucleoprotein complex 1 TBCE
death-inducing signaling complex 1 CASP3
cytoplasmic side of lysosomal membrane 1 EEF1A2
ribosome 1 TBCE
inclusion body 1 KEAP1
endothelial microparticle 1 ANXA5
photoreceptor ribbon synapse 1 ATP2B1
eukaryotic translation elongation factor 1 complex 1 EEF1A2


文献列表

  • Lucía Morote, Ángela Rubio-Moraga, Alberto José López Jiménez, Verónica Aragonés, Gianfranco Diretto, Olivia Costantina Demurtas, Sarah Frusciante, Oussama Ahrazem, José-Antonio Daròs, Lourdes Gómez-Gómez. Verbascum species as a new source of saffron apocarotenoids and molecular tools for the biotechnological production of crocins and picrocrocin. The Plant journal : for cell and molecular biology. 2023 Dec; ?(?):. doi: 10.1111/tpj.16589. [PMID: 38100533]
  • Aarif Ali, Amir Bashir Wani, Bashir Ahmad Malla, Jagadeesha Poyya, Nawab John Dar, Fasil Ali, Sheikh Bilal Ahmad, Muneeb U Rehman, Ahmed Nadeem. Network Pharmacology Integrated Molecular Docking and Dynamics to Elucidate Saffron Compounds Targeting Human COX-2 Protein. Medicina (Kaunas, Lithuania). 2023 Nov; 59(12):. doi: 10.3390/medicina59122058. [PMID: 38138161]
  • Luca Frattaruolo, Federica Marra, Graziantonio Lauria, Carlo Siciliano, Rosita Curcio, Luigina Muto, Matteo Brindisi, Donatella Aiello, Anna Napoli, Giuseppe Fiermonte, Anna Rita Cappello, Marco Fiorillo, Amer Ahmed, Vincenza Dolce. A Picrocrocin-Enriched Fraction from a Saffron Extract Affects Lipid Homeostasis in HepG2 Cells through a Non-Statin-like Mode. International journal of molecular sciences. 2023 Feb; 24(4):. doi: 10.3390/ijms24043060. [PMID: 36834472]
  • Xiongjie Zheng, Jianing Mi, Aparna Balakrishna, Kit Xi Liew, Abdugaffor Ablazov, Rachid Sougrat, Salim Al-Babili. Gardenia carotenoid cleavage dioxygenase 4a is an efficient tool for biotechnological production of crocins in green and non-green plant tissues. Plant biotechnology journal. 2022 11; 20(11):2202-2216. doi: 10.1111/pbi.13901. [PMID: 35997958]
  • Benjamin Moras, Camille Pouchieu, David Gaudout, Stéphane Rey, Anthony Anchisi, Xavier Saupin, Patrick Jame. Authentication of Iranian Saffron (Crocus sativus) Using Stable Isotopes δ13C and δ2H and Metabolites Quantification. Molecules (Basel, Switzerland). 2022 Oct; 27(20):. doi: 10.3390/molecules27206801. [PMID: 36296396]
  • Laurynas Jarukas, Konradas Vitkevicius, Olha Mykhailenko, Ivan Bezruk, Victoriya Georgiyants, Liudas Ivanauskas. Effective Isolation of Picrocrocin and Crocins from Saffron: From HPTLC to Working Standard Obtaining. Molecules (Basel, Switzerland). 2022 Jul; 27(13):. doi: 10.3390/molecules27134286. [PMID: 35807531]
  • Messiah Sarfarazi, Qadir Rajabzadeh, Razieh Tavakoli, Salam A Ibrahim, Seid Mahdi Jafari. Ultrasound-assisted extraction of saffron bioactive compounds; separation of crocins, picrocrocin, and safranal optimized by artificial bee colony. Ultrasonics sonochemistry. 2022 May; 86(?):105971. doi: 10.1016/j.ultsonch.2022.105971. [PMID: 35429897]
  • Bibi Marzieh Razavizadeh, Noora Arabshahi Delooei. Quantification of crocin, picrocrocin and safranal in saffron stigmas obtained from sounded corms with acoustic waves. Phytochemical analysis : PCA. 2021 Nov; 32(6):1059-1066. doi: 10.1002/pca.3047. [PMID: 33884676]
  • Samareh Babaei, Vahid Niknam, Mehrdad Behmanesh. Nitric oxide induced carotenoid contents in Crocus sativus under salinity. Natural product research. 2021 Mar; 35(5):888-892. doi: 10.1080/14786419.2019.1608544. [PMID: 31084371]
  • Natalia Moratalla-López, Shirin Parizad, Mina Koohi Habibi, Stephan Winter, Siamak Kalantari, Sayanta Bera, Candida Lorenzo, M Valle García-Rodríguez, Akbar Dizadji, Gonzalo L Alonso. Impact of two different dehydration methods on saffron quality, concerning the prevalence of Saffron latent virus (SaLV) in Iran. Food chemistry. 2021 Feb; 337(?):127786. doi: 10.1016/j.foodchem.2020.127786. [PMID: 32795861]
  • Fateme Sadat Moslemi, Atousa Vaziri, Golandam Sharifi, Javad Gharechahi. The effect of salt stress on the production of apocarotenoids and the expression of genes related to their biosynthesis in saffron. Molecular biology reports. 2021 Feb; 48(2):1707-1715. doi: 10.1007/s11033-021-06219-x. [PMID: 33611780]
  • Maricarmen Martí, Gianfranco Diretto, Verónica Aragonés, Sarah Frusciante, Oussama Ahrazem, Lourdes Gómez-Gómez, José-Antonio Daròs. Efficient production of saffron crocins and picrocrocin in Nicotiana benthamiana using a virus-driven system. Metabolic engineering. 2020 09; 61(?):238-250. doi: 10.1016/j.ymben.2020.06.009. [PMID: 32629020]
  • Javad Mottaghipisheh, Mohammad Mahmoodi Sourestani, Tivadar Kiss, Attila Horváth, Barbara Tóth, Mehdi Ayanmanesh, Amin Khamushi, Dezső Csupor. Comprehensive chemotaxonomic analysis of saffron crocus tepal and stamen samples, as raw materials with potential antidepressant activity. Journal of pharmaceutical and biomedical analysis. 2020 May; 184(?):113183. doi: 10.1016/j.jpba.2020.113183. [PMID: 32105944]
  • Shirin Parizad, Akbar Dizadji, Mina Koohi Habibi, Stephan Winter, Siamak Kalantari, Shahrbanoo Movi, Candida Lorenzo Tendero, Gonzalo L Alonso, Natalia Moratalla-Lopez. The effects of geographical origin and virus infection on the saffron (Crocus sativus L.) quality. Food chemistry. 2019 Oct; 295(?):387-394. doi: 10.1016/j.foodchem.2019.05.116. [PMID: 31174773]
  • Loriana Cardone, Donato Castronuovo, Michele Perniola, Nunzia Cicco, Vincenzo Candido. Evaluation of corm origin and climatic conditions on saffron (Crocus sativus L.) yield and quality. Journal of the science of food and agriculture. 2019 Oct; 99(13):5858-5869. doi: 10.1002/jsfa.9860. [PMID: 31206680]
  • Gianfranco Diretto, Oussama Ahrazem, Ángela Rubio-Moraga, Alessia Fiore, Filippo Sevi, Javier Argandoña, Lourdes Gómez-Gómez. UGT709G1: a novel uridine diphosphate glycosyltransferase involved in the biosynthesis of picrocrocin, the precursor of safranal in saffron (Crocus sativus). The New phytologist. 2019 10; 224(2):725-740. doi: 10.1111/nph.16079. [PMID: 31356694]
  • Zahra Aghaei, Seid Mahdi Jafari, Danial Dehnad. Effect of Different Drying Methods on the Physicochemical Properties and Bioactive Components of Saffron Powder. Plant foods for human nutrition (Dordrecht, Netherlands). 2019 Jun; 74(2):171-178. doi: 10.1007/s11130-019-00729-7. [PMID: 31001725]
  • Sheila Leone, Lucia Recinella, Annalisa Chiavaroli, Giustino Orlando, Claudio Ferrante, Lidia Leporini, Luigi Brunetti, Luigi Menghini. Phytotherapic use of the Crocus sativus L. (Saffron) and its potential applications: A brief overview. Phytotherapy research : PTR. 2018 Dec; 32(12):2364-2375. doi: 10.1002/ptr.6181. [PMID: 30136324]
  • Anastasia Kyriakoudi, Maria Z Tsimidou. Properties of encapsulated saffron extracts in maltodextrin using the Büchi B-90 nano spray-dryer. Food chemistry. 2018 Nov; 266(?):458-465. doi: 10.1016/j.foodchem.2018.06.038. [PMID: 30381212]
  • Fotini N Lamari, Vassilis Papasotiropoulos, Dimitris Tsiris, Stavros E Bariamis, Konstantinos Sotirakis, Efthimia Pitsi, Amalia P Vogiatzoglou, Gregoris Iatrou. Phytochemical and genetic characterization of styles of wild Crocus species from the island of Crete, Greece and comparison to those of cultivated C. sativus. Fitoterapia. 2018 Oct; 130(?):225-233. doi: 10.1016/j.fitote.2018.09.003. [PMID: 30213756]
  • Seyed Iman Hosseini, Naser Farrokhi, Khadijeh Shokri, Mohammad Reza Khani, Babak Shokri. Cold low pressure O2 plasma treatment of Crocus sativus: An efficient way to eliminate toxicogenic fungi with minor effect on molecular and cellular properties of saffron. Food chemistry. 2018 Aug; 257(?):310-315. doi: 10.1016/j.foodchem.2018.03.031. [PMID: 29622216]
  • Benjamin Moras, Loïc Loffredo, Stéphane Rey. Quality assessment of saffron (Crocus sativus L.) extracts via UHPLC-DAD-MS analysis and detection of adulteration using gardenia fruit extract (Gardenia jasminoides Ellis). Food chemistry. 2018 Aug; 257(?):325-332. doi: 10.1016/j.foodchem.2018.03.025. [PMID: 29622218]
  • Syed Imran Bukhari, Mahreen Manzoor, M K Dhar. A comprehensive review of the pharmacological potential of Crocus sativus and its bioactive apocarotenoids. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Feb; 98(?):733-745. doi: 10.1016/j.biopha.2017.12.090. [PMID: 29306211]
  • Sepehr Soleymani, Rezvan Zabihollahi, Sepideh Shahbazi, Azam Bolhassani. Antiviral Effects of Saffron and its Major Ingredients. Current drug delivery. 2018; 15(5):698-704. doi: 10.2174/1567201814666171129210654. [PMID: 29189153]
  • María José Bagur, Gonzalo Luis Alonso Salinas, Antonia M Jiménez-Monreal, Soukaina Chaouqi, Silvia Llorens, Magdalena Martínez-Tomé, Gonzalo L Alonso. Saffron: An Old Medicinal Plant and a Potential Novel Functional Food. Molecules (Basel, Switzerland). 2017 Dec; 23(1):. doi: 10.3390/molecules23010030. [PMID: 29295497]
  • Aubid Hussain Malik, Nasheeman Ashraf. Transcriptome wide identification, phylogenetic analysis, and expression profiling of zinc-finger transcription factors from Crocus sativus L. Molecular genetics and genomics : MGG. 2017 Jun; 292(3):619-633. doi: 10.1007/s00438-017-1295-3. [PMID: 28247040]
  • Afshin Faridi Esfanjani, Seid Mahdi Jafari, Elham Assadpour. Preparation of a multiple emulsion based on pectin-whey protein complex for encapsulation of saffron extract nanodroplets. Food chemistry. 2017 Apr; 221(?):1962-1969. doi: 10.1016/j.foodchem.2016.11.149. [PMID: 27979187]
  • M Valle García-Rodríguez, Horacio López-Córcoles, Gonzalo L Alonso, Christos S Pappas, Moschos G Polissiou, Petros A Tarantilis. Comparative evaluation of an ISO 3632 method and an HPLC-DAD method for safranal quantity determination in saffron. Food chemistry. 2017 Apr; 221(?):838-843. doi: 10.1016/j.foodchem.2016.11.089. [PMID: 27979282]
  • Riccardo Nescatelli, Simone Carradori, Federico Marini, Vicky Caponigro, Remo Bucci, Celeste De Monte, Adriano Mollica, Luisa Mannina, Mariangela Ceruso, Claudiu T Supuran, Daniela Secci. Geographical characterization by MAE-HPLC and NIR methodologies and carbonic anhydrase inhibition of Saffron components. Food chemistry. 2017 Apr; 221(?):855-863. doi: 10.1016/j.foodchem.2016.11.086. [PMID: 27979284]
  • Angelo Antonio D'Archivio, Andrea Giannitto, Maria Anna Maggi, Fabrizio Ruggieri. Geographical classification of Italian saffron (Crocus sativus L.) based on chemical constituents determined by high-performance liquid-chromatography and by using linear discriminant analysis. Food chemistry. 2016 Dec; 212(?):110-6. doi: 10.1016/j.foodchem.2016.05.149. [PMID: 27374513]
  • Andreas Chrysanthou, Evangelia Pouliou, Anastasia Kyriakoudi, Maria Z Tsimidou. Sensory Threshold Studies of Picrocrocin, the Major Bitter Compound of Saffron. Journal of food science. 2016 Jan; 81(1):S189-98. doi: 10.1111/1750-3841.13152. [PMID: 26605534]
  • Anastasia Kyriakoudi, Yvonne C O'Callaghan, Karen Galvin, Maria Z Tsimidou, Nora M O'Brien. Cellular Transport and Bioactivity of a Major Saffron Apocarotenoid, Picrocrocin (4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde). Journal of agricultural and food chemistry. 2015 Oct; 63(39):8662-8. doi: 10.1021/acs.jafc.5b03363. [PMID: 26340688]
  • Nikolaos Stavros Koulakiotis, Evangelos Gikas, Gregoris Iatrou, Fotini N Lamari, Anthony Tsarbopoulos. Quantitation of Crocins and picrocrocin in saffron by HPLC: application to quality control and phytochemical differentiation from other crocus taxa. Planta medica. 2015 May; 81(7):606-12. doi: 10.1055/s-0035-1545873. [PMID: 26018797]
  • Afshin Khavari, Azam Bolhassani, Fatemeh Alizadeh, S Zahra Bathaie, Prabha Balaram, Elnaz Agi, Rouhollah Vahabpour. Chemo-immunotherapy using saffron and its ingredients followed by E7-NT (gp96) DNA vaccine generates different anti-tumor effects against tumors expressing the E7 protein of human papillomavirus. Archives of virology. 2015 Feb; 160(2):499-508. doi: 10.1007/s00705-014-2250-9. [PMID: 25395243]
  • Lidia Rodríguez-Neira, María Asunción Lage-Yusty, Julia López-Hernández. Influence of culinary processing time on saffron's bioactive compounds (Crocus sativus L.). Plant foods for human nutrition (Dordrecht, Netherlands). 2014 Dec; 69(4):291-6. doi: 10.1007/s11130-014-0447-4. [PMID: 25373843]
  • M Valle García-Rodríguez, Jéssica Serrano-Díaz, Petros A Tarantilis, Horacio López-Córcoles, Manuel Carmona, Gonzalo L Alonso. Determination of saffron quality by high-performance liquid chromatography. Journal of agricultural and food chemistry. 2014 Aug; 62(32):8068-74. doi: 10.1021/jf5019356. [PMID: 25075549]
  • Mehdi Rabani-Foroutagheh, Yousef Hamidoghli, Seyed Ahmad Mohajeri. Effect of split foliar fertilisation on the quality and quantity of active constituents in saffron (Crocus sativus L.). Journal of the science of food and agriculture. 2014 Jul; 94(9):1872-8. doi: 10.1002/jsfa.6506. [PMID: 24288269]
  • Lina Cossignani, Eleonora Urbani, Maria Stella Simonetti, Angela Maurizi, Claudia Chiesi, Francesca Blasi. Characterisation of secondary metabolites in saffron from central Italy (Cascia, Umbria). Food chemistry. 2014 Jan; 143(?):446-51. doi: 10.1016/j.foodchem.2013.08.020. [PMID: 24054265]
  • Anastasia Kyriakoudi, Andreas Chrysanthou, Fani Mantzouridou, Maria Z Tsimidou. Revisiting extraction of bioactive apocarotenoids from Crocus sativus L. dry stigmas (saffron). Analytica chimica acta. 2012 Nov; 755(?):77-85. doi: 10.1016/j.aca.2012.10.016. [PMID: 23146397]
  • Sándor Gonda, Péter Parizsa, Gyula Surányi, Gyöngyi Gyémánt, Gábor Vasas. Quantification of main bioactive metabolites from saffron (Crocus sativus) stigmas by a micellar electrokinetic chromatographic (MEKC) method. Journal of pharmaceutical and biomedical analysis. 2012 Jul; 66(?):68-74. doi: 10.1016/j.jpba.2012.03.002. [PMID: 22464563]
  • Nikolaos Stavros Koulakiotis, Ernst Pittenauer, Maria Halabalaki, Anthony Tsarbopoulos, Günter Allmaier. Comparison of different tandem mass spectrometric techniques (ESI-IT, ESI- and IP-MALDI-QRTOF and vMALDI-TOF/RTOF) for the analysis of crocins and picrocrocin from the stigmas of Crocus sativus L. Rapid communications in mass spectrometry : RCM. 2012 Mar; 26(6):670-8. doi: 10.1002/rcm.6142. [PMID: 22328221]
  • Ana M Sánchez, Manuel Carmona, Manuel Jarén-Galán, M Isabel Mínguez Mosquera, Gonzalo L Alonso. Picrocrocin kinetics in aqueous saffron spice extracts (Crocus sativus L.) upon thermal treatment. Journal of agricultural and food chemistry. 2011 Jan; 59(1):249-55. doi: 10.1021/jf102828v. [PMID: 21141822]
  • N Esmaeili, H Ebrahimzadeh, K Abdi, S Safarian. Determination of some phenolic compounds in Crocus sativus L. corms and its antioxidant activities study. Pharmacognosy magazine. 2011 Jan; 7(25):74-80. doi: 10.4103/0973-1296.75906. [PMID: 21472084]
  • Angela Rubio-Moraga, Almudena Trapero, Oussama Ahrazem, Lourdes Gómez-Gómez. Crocins transport in Crocus sativus: the long road from a senescent stigma to a newborn corm. Phytochemistry. 2010 Sep; 71(13):1506-13. doi: 10.1016/j.phytochem.2010.05.026. [PMID: 20573363]
  • Seyed Ahmad Mohajeri, Hossein Hosseinzadeh, Fariborz Keyhanfar, Javad Aghamohammadian. Extraction of crocin from saffron (Crocus sativus) using molecularly imprinted polymer solid-phase extraction. Journal of separation science. 2010 Aug; 33(15):2302-9. doi: 10.1002/jssc.201000183. [PMID: 20589782]
  • C Priscila del Campo, Manuel Carmona, Luana Maggi, Charalabos D Kanakis, Eirini G Anastasaki, Petros A Tarantilis, Moschos G Polissiou, Gonzalo L Alonso. Picrocrocin content and quality categories in different (345) worldwide samples of saffron ( Crocus sativus L.). Journal of agricultural and food chemistry. 2010 Jan; 58(2):1305-12. doi: 10.1021/jf903336t. [PMID: 20028014]
  • Hossein Hosseinzadeh, Mohammad Hadi Modaghegh, Zahra Saffari. Crocus sativus L. (Saffron) extract and its active constituents (crocin and safranal) on ischemia-reperfusion in rat skeletal muscle. Evidence-based complementary and alternative medicine : eCAM. 2009 Sep; 6(3):343-50. doi: 10.1093/ecam/nem125. [PMID: 18955256]
  • Luana Maggi, Manuel Carmona, Amaya Zalacain, Magdalena Martínez Tomé, María Antonia Murcia, Gonzalo Luis Alonso. Parabens as agents for improving crocetin esters' shelf-life in aqueous saffron extracts. Molecules (Basel, Switzerland). 2009 Mar; 14(3):1160-70. doi: 10.3390/molecules14031160. [PMID: 19325516]
  • Ana M Sánchez, Manuel Carmona, Marin Prodanov, Gonzalo L Alonso. Effect of centrifugal ultrafiltration on the composition of aqueous extracts of saffron spice (Crocus sativus L.). Journal of agricultural and food chemistry. 2008 Aug; 56(16):7293-301. doi: 10.1021/jf801105x. [PMID: 18620411]
  • Matthias Lechtenberg, Dirk Schepmann, Michael Niehues, Nils Hellenbrand, Bernhard Wünsch, Andreas Hensel. Quality and functionality of saffron: quality control, species assortment and affinity of extract and isolated saffron compounds to NMDA and sigma1 (sigma-1) receptors. Planta medica. 2008 Jun; 74(7):764-72. doi: 10.1055/s-2008-1074535. [PMID: 18496783]
  • Nunzio D'Agostino, Daniele Pizzichini, Maria Luisa Chiusano, Giovanni Giuliano. An EST database from saffron stigmas. BMC plant biology. 2007 Oct; 7(?):53. doi: 10.1186/1471-2229-7-53. [PMID: 17925031]
  • Takashi Ochiai, Hiroshi Shimeno, Ken-Ichi Mishima, Katsunori Iwasaki, Michihiro Fujiwara, Hiroyuki Tanaka, Yukihiro Shoyama, Akihisa Toda, Reiko Eyanagi, Shinji Soeda. Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo. Biochimica et biophysica acta. 2007 Apr; 1770(4):578-84. doi: 10.1016/j.bbagen.2006.11.012. [PMID: 17215084]
  • Filkrat Abdullaev Jafarova, Heriberto Caballero-Ortega, Leticia Riverón-Negrete, Rogelio Pereda-Miranda, Roberto Rivera-Luna, Juan Manuel Hernández, Israel Pérez-López, Javier J Espinosa-Aguirre. [In vitro evaluation of the chemopreventive potential of saffron]. Revista de investigacion clinica; organo del Hospital de Enfermedades de la Nutricion. 2002 Sep; 54(5):430-6. doi: . [PMID: 12587418]
  • Hossein Hosseinzadeh, Hani M Younesi. Antinociceptive and anti-inflammatory effects of Crocus sativus L. stigma and petal extracts in mice. BMC pharmacology. 2002 Mar; 2(?):7. doi: 10.1186/1471-2210-2-7. [PMID: 11914135]
  • J Escribano, G L Alonso, M Coca-Prados, J A Fernandez. Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro. Cancer letters. 1996 Feb; 100(1-2):23-30. doi: 10.1016/0304-3835(95)04067-6. [PMID: 8620447]
  • P A Tarantilis, G Tsoupras, M Polissiou. Determination of saffron (Crocus sativus L.) components in crude plant extract using high-performance liquid chromatography-UV-visible photodiode-array detection-mass spectrometry. Journal of chromatography. A. 1995 May; 699(1-2):107-18. doi: 10.1016/0021-9673(95)00044-n. [PMID: 7757208]
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