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Home , Corydalis cava, Eschscholzia, Eschscholzia californica, Protopine, Reticuline

IAJPS 2017, 4 (02), 257-263 Ali Esmail Al-Snafi ISSN 2349-7750

CODEN (USA): IAJPBB ISSN: 2349-7750

INDO AMERICAN JOURNAL OF PHARMACEUTICAL SCIENCES

http://doi.org/10.5281/zenodo.344931

Available online at: http://www.iajps.com Review Article

ESCHSCHOLZIA CALIFORNICA: A PHYTOCHEMICAL AND PHARMACOLOGICAL - REVIEW Ali Esmail Al-Snafi Department of Pharmacology, College of Medicine, Thi qar University, Iraq.

Received: 10 February 2016 Accepted: 25 February 2017 Published: 28 February 2017 Abstract: Phytochemical analysis of californica showed that both aerial parts and roots contained , the latter being richer than the former, it contained up to 1.6% alkaloids. The alkaloids most commonly reported in included , chelirubine, macarpine, dihydromacarpine, californidine, , dihydrochelerythrine, chelilutine, dihydrochelilutine, sanguirubine, escholtzine, N-methyllaurotetanine, caryachine, O-methylcaryachine, , , , methyl laurotetanine, hunnemanine, norsanguinarine, pavine (6S,12S-neocaryachine-7-O- methyl ether N-metho salt), 1-(3-hydroxy-4-methoxybenzyl)-2-methyl-6,7-methylenedioxy-1,2,3,4-tetra hydroisoquinoline, as well as the dihydro-intermediates. The also contained a of colours including , red and yellow due to its different carotenoid composition. Six flavonol 3-O-glycosides were isolated from the aerial parts of Eschscholtzia californica. Flavonoids, in the Eschscholzia californica, occurred mainly as quercetin isorhamnetine glycosides. The previous pharmacological studies revealed that the plant possessed antifungal, , anxiolytic, sedative, behavioural activities and beneficial effect in vasomotor headache with an interesting mechanisms. This review was designed to discuss the chemical constituents and pharmacological effects of Eschscholzia californica. Keywords: Eschscholzia californica, pharmacology, contents, chemicals, therapeutic Corresponding author: Ali Esmail Al-Snafi, QR code Department of Pharmacology, College of Medicine, Thi qar University, Iraq. Cell: +9647801397994. E mail: [email protected]

Please cite this article in press as Ali Esmail Al-Snafi, Eschscholzia Californica: A Phytochemical and Pharmacological - Review, Indo Am. J. P. Sci, 2017; 4(02).

www.iajps.com Page 257 IAJPS 2017, 4 (02), 257-263 Ali Esmail Al-Snafi ISSN 2349-7750

INTRODUCTION: Eschscholzia californica var. ambigua (Greene) In the last few decades there has been an Jeps., Eschscholzia californica var. compacta exponential growth in the field of herbal medicine. (Lindl.) Jeps., Eschscholzia californica var. It is getting popularized in developing and crocea (Benth.) Jeps., Eschscholzia californica var. developed countries owing to its natural origin and douglasii (Hook. & Arn. ex Torr. & A.Gray) Jeps., lesser side effects. Plant derivates had been Eschscholzia californica var. luxurians Fedde, employed by population to prevent different kind Eschscholzia californica var. maritima (Greene) of diseases for centuries. The knowledge of plant Jeps., Eschscholzia californica var. peninsularis properties was acquired by ancient civilization that (Greene) Munz, Eschscholzia californica var. passed down from generation to generation until stricta (Greene) Jeps., Eschscholzia calosperma today. are a valuable source of a wide range Greene, Eschscholzia chartacea Fedde, of secondary metabolites, which are used as Eschscholzia clevelandi Greene, Eschscholzia pharmaceuticals, agrochemicals, flavours, cognata Greene, Eschscholzia columbiana fragrances, colours, biopesticides and food Greene,Eschscholzia compacta (Lindl.) Walp., additives [1-25]. Phytochemical analysis of Eschscholzia confinis Greene, Eschscholzia Eschscholzia californica showed that both aerial crocea Benth., Eschscholzia crocea var. parts and roots contained alkaloids, the latter being sanctarum (Greene) Fedde, Eschscholzia cucullata richer than the former, it contained up to 1.6% Greene, Eschscholzia cyathifera Greene, alkaloids. The alkaloids most commonly reported Eschscholzia debilis Greene, Eschscholzia in Eschscholzia californica included sanguinarine, diversiloba Greene, Eschscholzia douglasii (Hook. dihydrosanguinarine chelirubine, macarpine, & Arn. ex Torr. & A.Gray) Walp., Eschscholzia dihydromacarpine, californidine, chelerythrine, douglasii Hook. & Arn., Eschscholzia eastwoodiae dihydrochelerythrine, chelilutine, dihydro Greene, Eschscholzia floribunda Greene, chelilutine, sanguirubine, escholtzine, N-methyl Eschscholzia floribunda var. gorgonica Greene, laurotetanine, caryachine, O-methylcaryachine, Eschscholzia floribunda var. gracillima Fedde, protopine, allocryptopine, reticuline, methyl Eschscholzia foeniculacea Greene, Eschscholzia laurotetanine, hunnemanine, norsanguinarine, glauca Greene, Eschscholzia granulata Greene, pavine alkaloid (6S,12S-neocaryachine-7-O-methyl Eschscholzia granulata var. minuscula Fedde, ether N-metho salt), 1-(3-hydroxy-4-methoxy Eschscholzia helleriana Greene, Eschscholzia benzyl)-2-methyl-6,7-methylenedioxy-1,2,3,4-tetra helleriana var. tilingii Fedde, Eschscholzia inflata hydroisoquinoline, as well as the dihydro- Greene, Eschscholzia isostigma Greene, intermediates. The plant also contained a variety of Eschscholzia juncea Greene, Eschscholzia lacera colours including orange, red and yellow due to its Greene, Eschscholzia leptandra Greene, different carotenoid composition. Six flavonol 3-O- Eschscholzia leptomitra Greene, Eschscholzia glycosides were isolated from the aerial parts of leucosticte Greene, Eschscholzia marcida Greene, Eschscholtzia californica. Flavonoids, in the Eschscholzia marcida var. monticola Greene, Eschscholzia californica, occurred mainly as Eschscholzia maritima Greene. Eschscholzia quercetin isorhamnetine glycosides. The previous menziesiana Greene, Eschscholzia menziesiana pharmacological studies revealed that the plant var. anemophila Greene, Eschscholzia menziesiana possessed antifungal, analgesic, anxiolytic, var. coarctata Fedde, Eschscholzia menziesiana sedative, behavioural activities and beneficial var. nesiaca Fedde, Eschscholzia menziesiana var. effect in vasomotor headache with an interesting recedens Greene, Eschscholzia microloba Greene, mechanisms. This review will discuss the chemical Eschscholzia nitrophila Greene, Eschscholzia constituents and pharmacological effects of oregana Greene, Eschscholzia peninsularis Eschscholzia californica. Greene, Eschscholzia physodes Greene, Eschscholzia picta Greene,Eschscholzia Synonyms: pseudoinflata Fedde, Eschscholzia recta Greene, Chelidonium multifidum Moç. & Sessé ex DC., Eschscholzia revoluta Greene, Eschscholzia Chryseis caespitosa Torr. & A. Gray, Chryseis revoluta var. caudatocalyx Fedde, Eschscholzia californica (Cham.) Lindl., Chryseis compacta rigida Greene,Eschscholzia robusta Greene, Lindl., Chryseis crocea Lindl., Chryseis douglasii Eschscholzia rosea., Eschscholzia sanctarum Hook. & Arn. ex Torr. & A.Gray, Chryseis Greene, Eschscholzia scariosa Greene, hypecoides Torr. & A.Gray, Chryseis tenuifolia Eschscholzia scariosa var. dichasiophora Fedde, Torr. & A.Gray, Eschscholzia absinthiifolia Eschscholzia setchellii Fedde, Eschscholzia Greene, Eschscholzia ambigua Greene, shastensis Greene, Eschscholzia straminea Greene, Eschscholzia angularis Greene, Eschscholzia Eschscholzia stricta Greene, Eschscholzia apiculata Greene, Eschscholzia benedicta Greene, tenuisecta Greene, Eschscholzia thermophila Eschscholzia bernardina Greene, Eschscholzia Greene, Eschscholzia tristis Fedde, Eschscholzia bernardina var. coarctata Fedde, Eschscholzia vernalis Greene, Eschscholzia xylorrhiza Greene, biolettii Greene, Eschscholzia brandegeei Greene, www.iajps.com Page 258 IAJPS 2017, 4 (02), 257-263 Ali Esmail Al-Snafi ISSN 2349-7750

Eschscholzia yainacensis Greene and Eschscholzia sanguinarine, dihydrosanguinarine chelirubine, yainacensis var. modocensis Fedde [26]. macarpine, dihydromacarpine, californidine, chelerythrine, dihydrochelerythrine, chelilutine, dihydrochelilutine, sanguirubine, escholtzine, N- Taxonomic classification: methyllaurotetanine, caryachine, O- Kingdom: Plantae; Subkingdom: Viridiplantae; methylcaryachine, protopine, allocryptopine, Infrakingdom: Streptophyta ; Superdivision: reticuline, methyl laurotetanine, hunnemanine, Embryophyta; Division: Tracheophyta; norsanguinarine, pavine alkaloid (6S,12S- Subdivision: Spermatophytina; Class: neocaryachine-7-O-methyl ether N-metho salt), 1- Magnoliopsida; Superorder: Ranunculanae; (3-hydroxy-4-methoxybenzyl)-2-methyl-6,7- Order: ; Family: ; methylenedioxy-1,2,3,4-tetra hydroisoquinoline, : Eschscholzia; : Eschscholzia as well as the dihydro-intermediates [38-45]. californica [27]. The amounts of alkaloids isolated from the aerial Common names: part of Eschscholzia californica were: protopine : Arabic: Khishkhash ; Chinese: hua ling 0.514 ± 0.038, californidine: 12.5 ± 1.8, cao; English: California-, Golden poppy; allocryptopine: 0.0120 ± 0.0023, eschscholtzine: French: Eschscholzie de Californie, Pavot de 8.700 ± 0.51, sanguinarine: 0.0191 ± 0.0050, Californie; German: Kalifornischer Mohn; chelerythrine: 0.068 ± 0.011, reticuline: 1.095 ± Spanish: Amapolla de California; Swedish: 0.16, n-methyllaurotetanine: 5.68 ± 0.72 and Sömntuta [28-29]. caryachine: 0.410 ± 0.065 mg/ kg dry weight [44].

Eschscholzia californica contained a variety Description: of colours including orange, red and yellow due to California poppy is a flowering herbaceous annual their different carotenoid composition. Some to deep-rooted perennial. California poppy exhibits were white and this has been shown to be a growth form that is low-spreading to erect (0.5 – due to absence of carotenoids [46]. 2 ft) with basal and cauline foliage which is generally blue-green (glaucous) in appearance. The carotenoid isolated from Eschscholzia are ternate, with three finely divided lobes, californica were included: neoxanthin, and are nearly glabrous. Plants produce upright violoxanthin, luteoxanthin, auroxanthin, lutein, flowers on freely branching stems with four satiny zeaxanthin, mutatoxanthin, retro-carotene-triol, petals, colored bright orange to light yellow; eschscholtzxanthin, and ζ – carotene [47]. flowers may also have distinct, darker orange The aqueous ethanolic extract of aerial parts of centers [30-32]. Eschscholtzia californica yielded six flavonol 3-O- Traditional uses: glycosides. Flavonoids, in the Eschscholzia It was used as sedative, analgesic and californica, occurred mainly as quercetin antispasmodic. It is traditionally indicated for isorhamnetine glycosides [48-49]. treating the various physical and psychological Pharmacological effects: conditions including insomnia, bedwetting Analgesic, sedative and anaxiolytic effects: (incontinence), anxiety and nervous tension, The sedative effects of alkaloids detected in particularly in children [28, 33-36]. Indians on the Eschscholzia californica were attributed to western coast used this herb as a general pain chloride-current modulation, which were widely killer, and Indian women would also add this to the expressed in the brain mainly at the inhibitory food of their (unreactive) mates if pregnancy was interneurons. Electrophysiological studies on a desired. Native American used the California recombinant 훼 훽 훾 GABA receptor showed no Poppy in tea to treat headaches, anxiety, insomnia, 1 2 2 A effect of N-methyllaurotetanine at concentrations as a topical analgesic and to relieve tooth pain. lower than 30 휇M. However, (푆)-reticuline While Native American Indians would cut the root and apply the juice of the Poppy’s root to the behaved as positive allosteric modulator at the 훼3, source of their tooth pain. The plant was also used 훼5, and 훼6 isoforms of GABAA receptors. The as a remedy in cases of fever, rapid pulse and depressant properties of aerial parts of spasmodic cough [37]. Eschscholzia californica were assigned to chloride- current modulation by (푆)-reticuline at the 훼훽2훾2 and 훼5훽2훾2 GABAA receptors [44]. Chemical constituents: The aqueous alcohol extract of Eschscholzia Both aerial parts and roots contained alkaloids, the californica was evaluated for benzodiazepine, latter being richer than the former, it contained up neuroleptic, antidepressant, antihistaminic and to 1.6% alkaloids. The alkaloids most commonly analgesic properties. The aqueous alcohol extract reported in Eschscholzia californica included of Eschscholzia californica induced peripheral www.iajps.com Page 259 IAJPS 2017, 4 (02), 257-263 Ali Esmail Al-Snafi ISSN 2349-7750

analgesic effects in mice but did not possess Possible CNS mechanisms: antidepressant, neuroleptic or antihistaminic and The herbal drug Phytonoxon N is indicated in muscle relaxant effects. Furthermore, the extract nervousness induced insomnia, agitation and/or did not protect mice against the convulsant effects anxiety. It is composed of alcoholic drug extracts of pentylenetetrazol. However, the extract showed of the plants cava (20%) and an affinity for the benzodiazepine receptor, and Eschscholzia californica (80%). Both plants were thus, the sedative and anxiolytic effects of the rich in alkaloids derived from tyrosine extract were suppressed by flumazenil, an metabolism. Recent research showed that they antagonist of these receptors [35]. influence the neurotransmitter activity [33].

A multicenter, double-blind, randomized, placebo- A 70% ethanol extract of Eschscholzia californica controlled study was carried out in general practice was able to bind to 5-HT1A and 5-HT7 receptors at offices in Paris, France and the Paris area. Men and 100 mug/ml. The results of radioligand-binding women (N = 264) with mild to moderate assay of the isolated pure compounds, showed generalized anxiety disorder as diagnosed that the activity on the 5-HT1A receptor was at least according to the DSMIII- R criteria were partly due to the presence of the participated in the study. Patients received either 2 alkaloid, which showed the highest inhibition of tablets of placebo or Sympathyl® (Laboratoire [3H]8-hydroxy-2-(di-N-propylamino) tetralin Innotech International, Arcueil, France) twice daily ([3H]8-OH-DPAT) binding with an EC50 value of for 3 months. Sympathyl contains 75 mg of dry 155 nM and a Ki of 85 nM [45]. hydroalcoholic extract of the flowering head of hawthorn, 20 mg of dry aqueous extract of The protopine was also act as an inhibitor of both California poppy, and 75 mg of elemental serotonin transporter and noradrenaline transporter magnesium. Efficacy was assessed by change in in vitro assays. 5-hydroxy-DL-tryptophan(5-HTP)- Hamilton anxiety scale total and somatic scores, induced head twitch response (HTR) and tail change in patient self-assessment, number and suspension test were adopted to study whether percentage of responsive subjects (reduction of at protopine has anti-depression effect in mice using least 50% in Hamilton or self-assessment score) reference antidepressant fluoxetine and and the physician's clinical global impression. desipramine as positive controls. In HTR test, Treatment produced a rapid and progressive fall in protopine at doses of 5, 10, 20 mg/kg dose anxiety. There was a significant improvement in dependently increase the number of 5-HTP- the total anxiety score (P = 0.005), somatic score (P induced HTR. Protopine at doses of 3.75 mg/kg, = 0.054), and self-assessment (P = 0.005) in 7.5 mg/kg and 30 mg/kg also produced a dose- patients taking Sympathyl for 3 months [36]. dependent reduction in immobility in the tail suspension test [50]. Behavioural effects: The aqueous-alcoholic extract from Eschscholzia The aqueous extract of Eschscholzia californica californica inhibited the enzymatic degradation of reduced the behavioural parameters measured in a catecholamines as well as the synthesis of familiar environment test in mice (novelty adrenaline. The extract also dramatically shorten preference, locomotion and rearings in two the lag phase in the catalysis of phenolase probably compartments test) at doses above 100 mg/kg and due to their o-diphenol content, furtheremore, in non-familiar environment tests (staircase test) at dopamine beta-hydroxylase, monoamine oxidase doses above 200 mg/kg. The aqueous extract of (MAO-B) and diamine oxidases were inhibited by Eschscholzia californica at a dose a of 25 mg/kg, Eschscholzia californica extracts. These also possessed anxiolytic action since it produced mechanisms could explain the sedative, an increase of the number of steps climbed by mice antidepressive and hypnotic activities of in the staircase test (anticonflict effect) and that of Eschscholzia californica [51]. the time spent by animals in the lit box when they Protopine, and allocryptopine were were confronted with the light/dark choice demonstrated to enhance 3H-gamma-aminobutyric situation [34]. acid (3H-GABA) binding to rat brain synaptic For the treatment of vasomotor headache: membrane receptors. This effect might be indicate Because of the effect of Eschscholzia californica a benzodiazepine-like activity of these alkaloids on endogenous opiates, Eschscholzia californica [52]. (푆)-reticuline behaved as positive allosteric appeared effective in vasomotor headache. modulator at the 훼3, 훼5, and 훼6 isoforms of However, vasomotor headache has a GABAA receptors [44]. multifactorial pathogenesis and one factor is The roots and aerial parts of Eschscholzia anxiety, therefore, therapeutic efficacy of californica were extracted with ethanol, column Eschscholzia californica in headache could be chromatography, preparative TLC, and attributed to its anxiolytic effect [49]. crystallization. Fourteen isoquinoline alkaloids www.iajps.com Page 260 IAJPS 2017, 4 (02), 257-263 Ali Esmail Al-Snafi ISSN 2349-7750

were isolated from the ethanolic extract of the methylation. All phenolic hydroxy metabolites roots and aerial parts of Eschscholzia californica. were found to be partly conjugated. The' systematic All isolated compounds were tested for human toxicological analysis procedure using full-scan gas blood acetylcholinesterase (HuAChE) and human chromatography-mass spectrometry after acid plasma butyrylcholinesterase (HuBuChE) hydrolysis, liquid-liquid extraction and microwave- inhibition activity. None of the compounds isolated assisted acetylation allowed the detection of the significantly inhibited both HuAChE and main metabolites of californine and protopine in rat HuBuChE, but two alkaloids urine [55]. showed inhibitory activity against HuBuChE [40]. Side effects and contraindications: The potential effects of ethanolic extracts from This plant was considered child safe and based on Corydalis cava and Eschscholzia californica on normal intake levels there were no known side tyrosinase-catalyzed dimerization and/or oxidation effects from using this herb. The use of the of met-enkephalin were investigated. The results California poppy was not recommended for women showed that the peroxidase-catalyzed dimerization who were pregnant or breast-feeding. Users were via the tyr-residues is especially inhibited by the adviced not to drive or operate heavy machinery Corydalis cava extract. However, the tyrosinase- after using [28, 56]. catalyzed reaction yields five different products A- E, according to their HPLC-retention times. It was contra-indicated in glaucoma. It should not Consisting of the 4:1 (v/v) combination of the be taken with MAOIs, tranquilizers, CNS extracts from Eschscholzia californica and C. cava, depressants (e.g. alcohol, opiates, benzodiazepines, stimulated the formation of minor products A, B anaesthetics, tricyclic anti-depressants, anti- and E, whereas the formation of the major products epileptics), and Pentobarbital [57]. C and D was inhibited. Only products C and D exhibited properties similar to the peroxidase- CONCLUSION: derived dimer. Product A is likely to be identical to This review was design to highlight the chemical DOPA-enkephalin [53]. constituents and pharmacological effects of Eschscholzia californica effect was evaluated on Eschscholzia californica as a promising plant for Tert-Butyl hydroperoxide-induced injury in many pharmacological purposes as a results of isolated rat hepatocytes. Eschscholzia californica effectiveness and safety. showed both anti-lipoperoxidant and antihepatotoxic activity [54]. REFERENCES: 1. Al-Snafi AE. A review on Erodium cicutarium: Antifungal effects: A potential medicinal plant. Indo Am J P Sci 2017; The isoquinoline alkaloids, hunnemanine and 4(01): 110-116. norsanguinarine isolated from methanolic extract 2. Al-Snafi AE. Pharmacology of Echinochloa crus- of the whole Eschscholzia californica, were galli - A review. Indo Am J P Sci 2017; 4(01): 117- checked for their antifungal activity against 122. phytopathogenic fungi, Alternaria melongenae, A. 3. Al-Snafi AE. The pharmacological potential of brassicola, A. brassicae, Curvularia lunata, C. Dactyloctenium aegyptium- A review. Indo Am J P maculans, Helminthosporium pennisetti, H. oryzae, Sci 2017; 4(01): 153-159. H. turcicum, Fusarium undum and F. lini. 4. Al-Snafi AE. Chemical constituents, Hunnemanine exhibited 100 % inhibition of spore pharmacological and therapeutic effects of germination of A. brassicae, H. pennisetti and F. Eupatorium cannabinum- A review. Indo Am J P Sci lini at 1000 ppm whereas norsanguinarine 2017; 4(01): 160-168. exhibited 100 % inhibition of A. brassicicola and 5. Al-Snafi AE. Pharmacology and toxicology of Conium maculatum- A review. The Pharmaceutical C. maculans at the same concentration [38]. and Chemical Journal 2016; 3(2):136-142. http://tpcj.org/download/vol-3-iss-2-2016/TPCJ2016- Metabolism: 03-02-136-142.pdf The metabolism and the toxicological analysis of 6. Al-Snafi AE. The constituents and pharmacology the Eschscholzia californica alkaloids californine of Cnicus benedictus- A review. The Pharmaceutical and protopine was studied in rat urine using gas and Chemical Journal 2016; 3(2):129-135. chromatography-mass spectrometry. The identified http://tpcj.org/download/vol-3-iss-2-2016/TPCJ2016- metabolites indicated that californine was 03-02-129-135.pdf extensively metabolized by N-demethylation 7. Al-Snafi AE. Medicinal importance of Colchicum and/or single or double demethylenation with candidum- A review. The Pharmaceutical and consecutive catechol-O-methylation of one of the Chemical Journal 2016; 3(2):111-117. hydroxy groups. Protopine, however, only 8. Al-Snafi AE. Nutritional value and underwent extensive demethylenation of the 2,3- pharmacological importance of citrus species grown methylenedioxy group followed by catechol-O- www.iajps.com Page 261 IAJPS 2017, 4 (02), 257-263 Ali Esmail Al-Snafi ISSN 2349-7750

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