Journal of Pharmacology & Clinical Research ISSN: 2473-5574

Review Article J of Pharmacol & Clin Res - Volume 3 Issue 2 July 2017 Copyright © All rights are reserved by Afroze Alam DOI: 10.19080/JPCR.2017.03.555609 Pharmacology and Phytochemistry of from

Disha Choudhary and Afroze Alam*1,2,3 1Institute of Pharmacy, Shri Jagdish Prasad Jhabarmal Tibrewala University, 2Narayan Institute of Pharmacy, India 3School of Pharmacy, Shoolini University, India Submission: June 16, 2016; Published: July 13, 2017 *Corresponding author: Afroze Alam, Narayan Institute of Pharmacy, Jamuhar, Sasaram (Rohtas)-821305(Bihar)-India, Tel: ; Fax: ; Email: ;

Abstract

Iris is the largest and most complicated of family . Irises are mainly used as the ornamental , due to their colorful iris species species of iris have resulted in the isolation of flowers, or in the perfume industry, due to their violet like fragrance, but lot of were also used in many part of the worldsiris as medicinal plants for healing of a wide spectrum of diseases. The investigations of various variety of secondary metabolites. Approximately more than two hundred compounds have been reported from the genus which includes flavonoids, isoflavonoids and their glycosides, benzoquinones triterpenoids and stilbenes glycosides.

This genus is rich in isoflavonoidsIris which have a wide range of biological activity including anti-inflammatory, antioxidant and cancer chemo preventive properties. Nowadays phytochemical and pharmacological investigations bring new knowledge about chemical compounds in roots, and flowers of the species, about their chemical content and possible pharmacological and medicinal usage. This review brings suchtogether as cancer, results cardiovascular of the iris research disorder, in last and few osteoporosisor decades, putting against together the bacterial the information and viral about infections. the isolation of and their associated pharmacological activities. The reviews also signify the direct benefits of consumption of rich-diet and reduction of various diseases Keywords:

Cancer; Glycoside; Isoflavone; Iris species; Osteoporosis; Phytochemical investigation

Introduction General Introduction R1 O isolated from various species of Iris. The recognition of ‘clover Isoflavones are the most well-known of the disease’ in Australian sheep in the 1940s led to the investigation

Trifolium subterraneum of estrogenic activity of isoflavones [1]).The sheep whose diet L., Fabaceae) suffered from a reproductive disorder that reduced was predominately subterranean clover ( the lambing rates and involved abnormal lactation, changes OH O in the sex organs, permanent infertility, prolapsed uterus and R2 Figure 1: Common structure of Isoflavones. maternal dystocia [2] Isoflavones constitute the largest group Table 1: Different Substitutions of natural isoflavone. of natural isoflavonoids with large number of new structures of traditional medicine has promoted the increasing interest in Isoflavones R R reported in every year. The occurrence of isoflavonoids in plants 1 2 the search for biologically active constituents from both legume H OH and non-legume sources specially Iridaceae OH OH found in the family Iridaceae, in particular Iris species have a [3]. Isoflavones OH OCH3 H OCH 1). 3 characteristic 5, 6, 7-trioxygenation pattern [4] (Figure 1) (Table

J of Pharmacol & Clin Res 3(2): JPCR.MS.ID. 555609 (2017) 001 Journal of Pharmacology & Clinical Research

Occurrence these molecules mainly isolated from Iris species

Most members of the Fabaceae [12], which are species reportedOCH 3to be a rich source of isoflavones.H family contain significant HO O has found that the highest levels of genistein and daidzein HO O quantities of isoflavones. Analysis of levels in various in psoralea (Psoralea corylifolia). Various legumes including OCH3 (Glycine max L.), green bean (Phaseolus vulgaris L.), OH O H3CO OCH3 alfalfa sprout (Medicago sativa L.), mung bean sprout (Vigna OH OCH3 OH O radiata Vigna unguiculata Pueraria lobata L.), and red clover blossom and red clover sprout L.), cowpea ( L.), root ( H (Trifolium pratense L.) have been studied for their estrogenic OH H HO HO O O O O

HO OH OH OCH3 activity [5]. Highly processed foods made from legumes, such as H3CO H3CO OH O , retain most of their isoflavone content, with the exception OCH3 biochanin A), alfalfa OH O of fermented , which has increased levels.Other dietary OCH3 OH (formononetin), and peanut (genistein 7-Glycoside sources of isoflavones include chick pea ( Iristectoriginin-B found in the Iridaceae family (Iris species).In tissue; they H ) [6]. Isoflavones are also most often occur as glycosides or their respective malonates or HO O

OCH3 acetyl conjugates, rendering them even more water-soluble [7]. H3CO and disease states led to the investigation of a series of bioactive OH O Epidemiological studies indicating associations between diet OH plant compounds, called . Some of these non- Iristectoriginin-B

Figure 2: Structure of Isoflavone from different Iris species. nutrient plant chemicals, such as phytoestrogens were shown to structurally and functionally similar to human . There Pharmacology of Isoflavones confer significant long-term health benefits. Phytoestrogens are Antioxidant and Antimicrobial (Antibacterial and Antifungal) Activity of isoflavones: Rigano Det al. are two types of phytoestrogens, the and the isoflavones. genistein are especially rich in isoflavones. They contain the glycosides and . We herein report the use of this . isoflavones and daidzein and their respective β- [13] explained theantioxidant activity of isoflavonoids Iris Chromatographic separation of a methanolic extract from and flavonoids from of species. Iris pseudopumila aglycone (Isoflavone) as a versatile molecule isolated from Phytochemistry of Isoflavones rhizomes led to the isolation of two new natural compounds, and isoscutellarein, along with determined on the basis of spectroscopic evidence. Isolated one of the most distinctive chemical features of the genus Iris 9 isoflavonoids and 4 flavonoids. Their structures were The presence of isoflavones in rhizomes or aerial parts is [8]. using the luminol-dependent chemiluminescence assay, irigenin and its 7-glucoside iridin in , of . compounds were evaluated for their antioxidant activity One of the earliest reports on this genus was of the isoflavones with as a positive control. Irilone and Their chemical structures were determined by Baker [9]. The rarely observed outside Iris. Within Iris showed significant antioxidant activity [13]. Rigano Det al. isoflavone irigenin has a unique substitution pattern, which is and cytotoxicity of different extracts from Iris pseudopumila accompanied by one or more related structures but particularly [14] explained comparative free radical scavenging potential , irigenin is frequently Tineo I. tectorum Maxim. Some flowers and rhizomes. in vitro antioxidant by tectorigenin, first obtained from Iris and cytotoxic activities of different extracts from Iris pseudopumila thirty other isoflavones have been described variously from The aim of this study was to evaluate the from Thunb (aerial parts), I. nigricans Dinsm. Tineo rhizomes species. A recent review described several new structures (rhizomes) and I. kashmiriana Baker(rhizomes flowers and . The radical scavenging activity was ) [10]. Finally, assessed by means of DPPH assay. The antioxidant activity was the Leguminosae and at least a dozen other dicotyledonous lipid peroxidation of liposomes. Methanolic and chloroform it should be emphasized that isoflavones, while occurring in assessed by means of two tests: bleaching of β-carotene and families, are relatively rare in the . There are pseudopumila of 101 and 83 µg mL , respectively. Iridaceae, in Festuca L.(Gramineae) 50 extracts from the flowers of I. showed−1 a significant and Hemerocallis L Hemerocallidaceae only two reports outside the antiradical effect with IC 50 of 18 µg mL ) and . (now ) [11] (Figure 2). As regards to lipid peroxidation, the best activity was showed−1 chloroform extract of rhizomes (IC50 33 µg mL ). The cytotoxic The unique structural pattern associated with the isoflavones by methanolic extract of flowers (IC −1 prompted us to undertake the phytochemical investigation of activity was carried out using the Sulforhodamine B (SRB)

How to cite this article: Disha C, Afroze A. Pharmacology and Phytochemistry of Isoflavonoids from Iris Species. J of Pharmacol & Clin Res. 2017; 3(2): 002 555609. DOI: 10.19080/JPCR.2017.03.555609. Journal of Pharmacology & Clinical Research

assay. The chloroform extract from rhizomes demonstrated a 50value of 0.12 mg/ good cytotoxic activity against amelanotic melanoma cancer ml followed by the aqueous extract with an IC of 57 µg mL . The results obtained 50 ml. Phytochemical analysis revealed the presence of isoflavone, support the ethno medical claims for the−1 plant. Al-Khateebet al may be responsible for antimicrobial and antioxidant activities cell line (C32) with an IC flavonoids, terpenoids, saponins, alkaloids and tannins which Iris In Vitro antimicrobial activity of Iris nigricance methanolic extract containingphenolic compounds. pseudacorus In this study, the effects of antibacterial activity [15], investigated antioxidant and antimicrobial activities of [16]. Ramtin et al [17], of essential oils, native plant northern of ,

Iris nigricans It has been observed from results that the flowers extract of were investigated for some selected bacteria The influence have the highest radical scavenging activity with the micro-broth dilution methods against standard strains of the of essential oils was tested by the using of disk diffusion and lowest IC50 value of 2.549 μg/ml followed by the leaves extracts with an IC50 value of 26.436 μg/ml. While the rhizomes extracts and minimum bactericidal concentration (MBC) of essential oils picked out bacteria. Minimum inhibitory concentrations (MIC) have the lowest radical scavenging activity with an IC50 value of 40.064 μg /ml. The results indicated that the antioxidant activity crude extracts. The phytochemical analysis of different parts of were utilized for this goal [17]. of flowers extract was higher than ascorbic acid and the other activity of methanolic extract from Iris pseudopumila rhizomes. Rigano D et al. [18] investigated antibacterial and allopathic the presence of major phytocompounds as phenolic compounds Did “ Antimicrobial screening of Iris aitchisonii (rhizomes, leaves and flowers) extracts indicated (Bakar) Boiss” might be responsible for the antioxidant activity. Preliminary Iris aitchisonii (xanthones isoflavonoids and flavonoids) and acids, which The present study was an attempt to verify the ethno botanical antibacterial and antifungal activities of methanolic extracts of knowledge of (Bakar) Boiss, a local plant, on Iris nigricans Minimum Inhibitory Concentration (MIC) of its crude extracts. scientific lines by evaluating the antimicrobial activity including (rhizomes, leaves and flowers) were evaluated. amongst all. These activities may be attributed to the presence for obtaining its crude extracts in petroleum ether, chloroform, The extract have showed promising antibacterial activity The plant material after its collection was subjected to maceration and antifungal potential, i.e. 45±1.73mm and 57±1.0mm against of phenolic components (Isoflavone, Flavonoids and Xanthones) methanol and water. The results indicated highest antibacterial Pseudomonas aeruginosa and Aspergillus niger respectively. MIC which can disrupt the cell membranes or inhibit the synthesis of value of the methanolic extract against Staphylococcus aureus certainAntifungal enzymes Activity: [15]. The antifungal activity of methanolic and Pseudomonas aeruginosa extracts of Iris nigricans Anti-proliferative Activity: was Afroze 0.002μg/mL et al. [19].(2017) reported (rhizomes, leaves and flowers) were Iris screened and observed that leaves extract shows stronger inhibition zone of leaves extract against Candida albicans kashmiriana antifungal activity than rhizomes and flowers extracts. The two new glycosides and related isoflavonoids from Baker and subjected to structure elucidation was 15 mm while the inhibition zone of the well-known followed by their biological evaluation. Isolated compounds 1H NMR, 13C antifungal agent nystatin that was 17 mm. Therefore, the were characterized and identified by a combination of NMR, DEPT, 2-D NMR and mass spectrometry coupled antifungal activity of leaves extract was comparable to that various spectroscopic technique vis. UV, IR, scavenging and antibacterial activity of essential oil and in silico library of of nystatin [15]. Ilyas et al (2012) proposed free radical solvent extracts of with chemical analysis. Furthermore, an (Mill) was investigated. isolated isoflavones and its analogues were designed. NF- mass spectrometry (GC-MS) and a total of 38 types of The essential oil was analyzed by Gas chromatography kappa B (transcription factor that facilitates angiogenesis, target to evaluate the anticancer and antioxidant activity of inflammation, invasion and metastasis) was selected as a volatile organics were identified. The essential oil consists chiefly of alkanes (36.5%), acids (19.1%), ketones (11.7%), isoflavones and its analogues. The cell cycle specificity of the alcohols (9.0%), arylpropanoids (6.8%) and aldehydes cytotoxicity was further analyzed by corresponding analysis, (4.1%) accompanied by relatively much smaller amounts using flow cytometer. of monoterpenes (1.0%). The antimicrobial activity of 5,7,8-trihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one,5,7,8- activity against Salmonella typhimuriumand Klebsiella Most of the compounds exhibit moderate activity, whereas the essential oil and ethanolic extract shows an important trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one,5,7,8- pneumonia triacetoxyoxy-3-(4-methoxyphenyl)-4H-chromen-4-one and 3.12 mg/ml. Furthermore, the free radical scavenging assay with minimum inhibitory concentration (MIC) of 6,7-diacetoxyoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

2,2-diphenyl-1-picrylhydrazyl (DPPH) test system. 50 of the essential oil and extracts were determined using a showed distinct broad-spectrum anticancer activity with IC indicates that these compounds induced cell cycle arrest at G2/M values ranges between 3.8 and 5.6 mg/mL. Cell cycle analysis value of 0.1 mg/ The dichloromethane and water extract 50 possessed strong radical scavenging activity with the lowest IC phase [8] (Figure 3(A & B)).

How to cite this article: Disha C, Afroze A. Pharmacology and Phytochemistry of Isoflavonoids from Iris Species. J of Pharmacol & Clin Res. 2017; 3(2): 003 555609. DOI: 10.19080/JPCR.2017.03.555609. Journal of Pharmacology & Clinical Research

and isoorientin-6-O’’-β

OR3 -D-glucopyranoside showed a selective 1 8 activity against amelanotic melanoma cells with a percentage R2O 8' O In Vitro Activities of 7 2 of inhibition of 83.2 and 79.8, respectively [20]. Wollenweberet Iris germanica A C al. [21] described “Cancer Chemopreventive 3 2' Iris germanica 6 Isoflavones Isolated from ”. Six known isoflavones 4' 1' 5 4 3' were isolated from of , [21]. These B compounds were examined for their cancer chemopreventive 4' 50 value in the range 0.25-4.9 µM. OR1 O 6' potential. They were shown to be potent inhibitors of cytochrome OCH 5' 3 P 450Isoflavones IA activity with as IC phytohormones and phytosterols: Figure 3(A): Glycoside-I. Isoflavones have the phenyl group attached to the 1) R = H, R = Glu, R = H ; 1a) R = -OCOCH3, R = Glu, R = 1 2 3 1 2 3 3-position, whereas in flavones the phenyl group is attached OCOCH ; 3 to the 2-position. The isoflavones are mainly found to occur 1b) R , R , R = H ; 1c) R , R , R = OCOCH ; 1d)R = OCH R =Glu 1 2 3 1 2 3 3 1 3 2 within the Leguminosae (specifically in the sub-family R3 = OCH3 species 1e) R = OCH ; R = -OH, R = OCH ; 1f ) R = OCH ; R = OCOCH Papilionoideae), although the literature shows many other 1 3 2 3 3 1 3 2 3 also found in other botanical families such as the Compositae, R = OCH that contain these chemical moieties Isoflavones are 3 3 the Iridaceae, the Myristicaceae, and the Rosaceous. 1g) R1 , R2, R3 = H ; OCH3 = OH, Glu= Glucose.

stereochemical space that could be occupied by oestrogenic 8 1 These isoflavones can act as steroidal mimics by filling the R O O compounds. It is this special chemistry that helps explain 2 7 8' 2 the effects of many nutritional herbal supplements and A C 6 3 2' 4' 1' topical preparations [22]. The Figure 4 shows daidzein in ER R O 3' 1 5 4 Receptor [23]. B O 6' 4' OCH 5' 3 HO O Figure 3(B): Glycoside-II.

2) R1= H, R2 = Glu, 2a)R1 = -COCH3, R2 = H 2b) R1 , R2, = -COCH3 2c)

R1, R2 = H O OH 2d)R1 = CH3 ; R2 = Glu, 2e) R1= CH3 ; R2 = H, 2f) R1 = CH3 ; R2 = -OCOCH3 Glu= Glucose Figure 3(A,B): Structure of glycoside - I&II and their aglycones (Isoflavones). Diadzein in ER Receptor.

Figure 4: Diazdein in active site of the ER receptor. Conforti et al. [20], reported anti-proliferative activity on compounds isolated from Iris pseudopumila human cancer cell lines after treatment with polyphenolic Anti-osteoporotic activity: rhizomes. The study described the anti-proliferative properties Iris (Iris pseudacorus) flowers and Jung-Lye Kim et al. [24] reported of Iris pseudopumila Extract Modulating Differentiation of Osteoblasts and osteogenic activity of Yellow Flag constituents isolated from them. The In Vitro cytotoxic activity flowers and rhizomes extracts and fourteen Iris extract (YFIE) and revealed its anti-osteoporotic effects in Osteoclasts. This study investigated the yellow flag osteoblastic MC3T3-E1 mouse cells and RAW 264.7 murine assay against two human cancer cell lines, large lung carcinoma (CORL-23) and amelanotic melanoma (C32), showed that the μg/ml µg/ml YFIE in an osteogenic medium, the bone nodule most anti-proliferative extract was the MeOH extract from against amelanotic melanoma cells. The most anti-proliferative macrophages. When osteoblasts were treated with 1–20 flowers with a percentage of inhibition of 50.9 at 100 3-O-β-D-glucopyranoside and Iris formation by calcium deposits was markedly enhanced compounds against amelanotic melanoma cells were kaempferol- inhibition of 100 and 96.6, respectively, and against large lung during differentiation. Consistently, YFIE stimulated alkaline olidone with a percentage of phosphatase activity and collagen type I secretion with a substantialImmunomodulatory effect on osteoblast activity: proliferation [24] (Figure 4). carcinoma cells with a percentage of inhibition of 82.1 and 84.6, β Iris respectively. Significant activity on the amelanotic melanoma cell Nazir et al. [25] Showed a percentage of inhibition of 89.3. The compounds isovitexin germanica (Iridaceae line was also showed by irigenin-7-O- -D-glucopyranoside, with immunomodulatory activityof isoflavone isolated from ) on T-lymphocytes and cytokines.

How to cite this article: Disha C, Afroze A. Pharmacology and Phytochemistry of Isoflavonoids from Iris Species. J of Pharmacol & Clin Res. 2017; 3(2): 004 555609. DOI: 10.19080/JPCR.2017.03.555609. Journal of Pharmacology & Clinical Research

been largely documented. The estrogenic activities of genistein, Irisolidone) (1) The immunomodulatory activities of two isoflavones, at the molecular, preclinical, and clinical levels to determine their 5,7-dihydroxy-6,4’-dimethoxyisoflavone ( daidzen, and are currently being extensively investigated (2) isolated from Iris germanica (Iridaceae potential for the treatment of chronic diseases such as hormone- and 5,4’-dihydroxy-6,7-methylenedioxyisoflavone (irilone) dependent cancer, cardiovascular diseases, and osteoporosis. ) was reported. Their influence on production of T-lymphocytes (CD4+ IFN-gamma and Th2: IL-4 and IL-5 in a dose-dependent and CD8+ cells) and T-cell cytokines, namely Th1: IL-2, The wide spectrum of pharmacological activities associated phytochemical and pharmacological investigations on various mice. Oral administration of drugs at doses of 0.1-0.8 mg/ with the isoflavones prompted us to compile a review on manner was studied by flow cytometric method in Balb/c

biological activities of various plants which are reported to be a kg per oral dose showed 1 to possess stimulatory activity the Iris species rich source of isoflavones. In conclusion, there is no doubt that on T-cells and Th1 cytokine production, while as 2 acted as and related phenolic constituents. Many of these are potentially contain a heterogeneous collection of isoflavone an immunosuppressant for both cells and cytokines. The methylated products of 1 and 2 showed a similar trend to that are still needed to establish an exhaustive structural activity decreased revealing the importance of free phenolic groups useful as taxonomic markers, but further detailed surveys of their parent compounds but their activity was drastically relationship as potent bioactive candidate. Acknowledgment forTraditional their immunomodulatary and Economical activities Importance [25]. of Genus Iris: Several cultures have used species of Iris as food, ornamental, condimental, or medicinal plants. The Navajo, the largest The authors thank to Narayan Institute of Pharmacy and Native American tribe of North America, used decoctions Narayan Medical College & Hospital, Jamuhar-821305, Sasaram of – Bihar (India). We also thank to School of Pharmaceutical of the same species as an emetic [26] Pieces of the rhizome Sciences Shoolini University, Solan, (H.P) to facilitate part of this were used to relieve toothaches, or Referenceswork. earaches [27]. The mashed roots of were 1. infusions of dry roots of the same species applied to wounds, presumably as an antiseptic and the state of research. Phytother Res 17(8): 845-869. Ososki AL, Kennelly EJ (2003) Phytoestrogens: a review of the present were used to calm 2. pain. Leaves or leaf-sap were used as a dye, to give the blue problem of sheep on subterranean clover pastures in Western Australia.Bennetts Aust HW, Vet Uuderwood J 22(1): 2-12. EJ, Shier FL (1946) A specific breeding color to tattoos. The use of the leaves, macerated with salt, sugar, and other spices was recommended to clean the skin 3. phytoestrogens as a replacement for traditional estrogen replacement and cure skin diseasesx [28]. was used in India as Iris species are of considerable therapy.Glazier MG, Arch Bowman Intern MedMA (2001) 161(9): A 1161-1172.reviews of the evidence for the use of anthelmintic and diuretic, and, mixed with other species, to economic importance in ornamental horticulture and the 4. treat venereal diseases [29]. Irisgladiolus, and Irisfreesia. Woźniak D, Matkowski A (2015) Belamcandae chinensis rhizoma–a Several other genera (e.g., , , , 5. cut-flower industry, especially review of phytochemistry and bioactivity. Fitoterapia 107: 1-4. and ) are cultivated in gardens in both tropical and Tsao R, Papadopoulos Y, Yang R, Young JC, McRae K (2006) Isoflavone temperate areas. and Homeria are poisonous and profiles of red clovers and their distribution in different parts harvested 6. at different growing stages. J Agric Food Chem 54(16): 5797-5805. notably in southern Africa proteins. J Agric Food Chem 49(3): 1069-1086. Friedman M, Brandon DL (2001) Nutritional and health benefits of soy pose significant problems in cattle- and sheep-raising areas, 7. Dillard CJ, German JB (2000) Phytochemicals: nutraceuticals and Conclusion human health. J Sci Food Agric 80(12): 1744-1756. 8. Iris kashmiriana Isoflavonoids and flavonoids are prominent plant secondary Alam A, Jaiswal V, Akhtar S, Jayashree BS, Dhar KL (2017) Isolation of by humans as dietary constituents. Although not considered metabolites with variable phenolic structures and are consumed isoflavones from Baker as potential anti proliferative 9. agentsLee SJ, targetingAhn JK, Khanh NF-kappaB. TD, Chun Phytochemistry SC, Kim SL, et 136: al. (2007)70-80. Comparison nutrients and thus essential for life, ingestion may 55(23):of isoflavone 9415-9421. concentrations in soybean (Glycine max (L.) Merrill) play a significant role in health and disease Numerous studies sprouts grown under two different light conditions. J Agric Food Chem have shown an association between isoflavone-rich dietary 10. Nat Prod Rep 15(3): 241-260. consumption and reduced cancer risk, particularly breast and act as inhibitors of the multidrug resistance transporter MRP1 Boland GM, Donnelly DM (1998) Isoflavonoids and related compounds. prostate cancers It has been shown that some isoflavones can 11. 2(3): 371-390. Umezawa T (2003) Diversity in biosynthesis. Phytochem Rev by influencing the biophysical properties of membranes. The 12. osteoporosis, and menopausal symptoms in addition to their experimental approaches, and dereplication strategies for the preventive role of isoflavones in cancer cardiovascular diseases, discoveryMichel T, of Halabalaki novel phytoestrogens M, Skaltsounis from ALnatural (2013) sources. New Planta concepts, Med 79(7): 514-532. antioxidant anti-inflammatory and estrogenic activities has

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How to cite this article: Disha C, Afroze A. Pharmacology and Phytochemistry of Isoflavonoids from Iris Species. J of Pharmacol & Clin Res. 2017; 3(2): 006 555609. DOI: 10.19080/JPCR.2017.03.555609.