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Journal of Advanced Research (2016) 7, 499–514 Cairo University Journal of Advanced Research REVIEW Phytochemistry, biological activities and potential of annatto in natural colorant production for industrial applications – A review Shahid-ul-Islam, Luqman J. Rather, Faqeer Mohammad * Department of Chemistry, Jamia Millia Islamia (A Central University), New Delhi 110025, India G R A P H I C A L A B S T R A C T A R T I C L E I N F O Article history: Received 4 September 2015 Received in revised form 5 November 2015 A B S T R A C T Bixa orellana commonly known as annatto is one of the oldest known natural dye yielding plants native to Central and South America. Various parts of annatto have been widely used in the traditional medical system for prevention and treatment of a wide number of health disorders. The plethora of traditional uses has encouraged researchers to identify and isolate * Corresponding author. Tel.: +91 9350114878. E-mail address: faqeermohammad@rediffmail.com (F. Mohammad). Peer review under responsibility of Cairo University. Production and hosting by Elsevier http://dx.doi.org/10.1016/j.jare.2015.11.002 2090-1232 Ó 2015 Production and hosting by Elsevier B.V. on behalf of Cairo University. 500 S.ul-Islam et al. Accepted 16 November 2015 Available online 30 November 2015 Keywords: Annatto Bixin Antibacterial activity Anticancer activity Textile dyeing phytochemicals from all parts of this plant. Carotenoids, apocarotenoids, terpenes, terpenoids, sterols, and aliphatic compounds are main compounds found in all parts of this plant and are reported to exhibit a wide range of pharmacological activities. In recent years annatto has received tremendous scientific interest mainly due to the isolation of yellow–orange natural dye from its seeds which exhibits high biodegradability, low toxicity, and compatibility with the environment. Considerable research work has already been done and is currently underway for its applications in food, textile, leather, cosmetic, solar cells, and other industries. The present review provides up-to-date systematic and organized information on the traditional usage, phytochemistry and pharmacology of annatto. It also highlights its non-food industrial applications in order to bring more interest on this dye plant, identifies the existing gaps and provides potential for future studies. Studies reported in this review have demonstrated that annatto holds a great potential for being exploited as source of drugs and a potential natural dye. However, further efforts are required to identify extract biomolecules and their action mechanisms in exhibiting certain biological activities in order to understand the full phytochemical profile and the complex pharmacological effects of this plant. Ó 2015 Production and hosting by Elsevier B.V. on behalf of Cairo University. Shahid-ul-Islam is a doctorial student doing research work in Dr. Faqeer Mohammad’s group at the Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi, India. His research is focused on natural colorants, biopolymers, green chemistry, and functional textiles. He has numerous academic publications in International journals of high repute to his credit and has also contributed to several internationally recognized books published by John Wiley & Sons, Springer, and Studium Press LLC. His research papers are cited in well-reputed scientific journals published by Nature, The American Chemical Society, and The Royal Society of Chemistry. Additionally two of his papers appeared in ScienceDirect’s Top 25 hottest articles from the Journal of Cleaner Production in 2013, 2014 and 2015. Luqman Jameel Rather is a PhD student working in the field of Natural dyes in Dr. Faqeer Mohammad’s group in Department of Chemistry Jamia Millia Islamia, New Delhi. He earned his M.Sc. Chemistry in 2010 from University of Kashmir, Srinagar. He qualified CSIR-NET in 2011. His research is focused on thermodynamic and kinetic adsorption studies of natural colorants on wool, and development of fluorescent textiles. Faqeer Mohammad is a Senior Assistant Professor in the Department of Chemistry, at Jamia Millia Islamia, (A Central University), New Delhi, India. He received his M. Sc, M.Phil and Ph.D in 1975, 1979, and 1982, respectively, from Aligarh Muslim University, Aligarh, UP, India. During his PhD he was awarded with JRF and SRF Research Fellowships from UGC and CSIR. He has published numerous research articles, reviews and book chapters all in the journals of International repute. He has until now supervised 20 graduate M. Sc and 4 Ph.D theses. His research interests are in the field of natural dyes and their applications. Introduction Bixa orellana L. commonly known as annatto belongs to the family Bixaceae. It is 3–6 m high bush native to Central and South America and is one of the oldest known natural dye yielding plants, Fig. 1. It was named after the Spanish conquistador Francisco de Orellana and has been used earlier for body painting, treatment for heartburn and stomach distress, sunscreen, and repelling insects, and to ward off evil [1]. Annatto has been used for centuries in many parts of the world for the prevention and treatment of a number of heath disorders such as constipation, fevers, heartburn, asthma, scabies, ulcers, diarrhea, stomach upset, skin diseases, measles, anecdotal treatment of diabetes, allergy, leprosy, infectious diseases, burns, measles, gonorrhea, diarrhea, asthma, angina, tumors, skin problems, and urinary infections (oral and topic) [2,3]. The pulp from seeds of this plant has long been used topically by indigenous people to enhance the beauty of lips which has led to the origin of B. orellana’s nick name as lipstick tree [4]. Annatto has enormous number of applications in coloring and bleaching of dairy food products especially bakery products, cream deserts, butter milk deserts, rice flour, and corn starch [5–7]. Extensive research studies carried out in the last few decades have shown isolation of several different classes of phytoconstituents including carotenoids, apocarotenoids, sterols, aliphatic compounds, monoterpenes and sesquiterpenes, triterpenoids, volatile oils and other miscellaneous compounds from all parts of this plant [8–10]. These phytochemicals exhibit a wide range of pharmacological activities that include antibacterial, antifungal, antioxidant, anti-inflammatory, anticancer, enhanced gastrointestinal motility, neuropharmacological, anticonvulsant, analgesic, and antidiarrheal activities [11–15]. Modern investigations on this plant have revealed the presence of natural reddish-yellow dye in seeds of B. orellana. The fruit of the B. orellana tree consists of 10–50 seeds of the size of grape seeds covered with a thin layer of soft, slightly sticky vermilion pulp [16]. Seeds are characterized by substantial amount of carotenoid compounds mainly apocarotenoid bixin, nor-bixin and other less important cryptoxanthin, lutein, zeaxanthin, and methylbixin [17–19]. Numerous pieces of research have been conducted on B. orellana plant over the last few years; however, there is a paucity of comprehensive review Phytochemistry and biological activities of Bixa orellana Fig. 1 501 (a) Plant (b) leaves and flower, and (c) seeds and dye. articles on this potential natural dye plant [4,6,14]. Keeping in view the tremendous interest in this dye containing plant, we herein summarize up-to-date information on the phytochemistry, and biological activities of annatto. Finally this review also highlights its important industrial applications with critical analysis of the existing gaps and potential for future studies. Method An extensive and systematic review of the existing literature was collected from scientific journals, books, reports and worldwide accepted databases (Scopus, ScienceDirect, Scifinder, Medline, Springer, and Google Scholar) using different search key words such as annatto, B. orellana, phytochemistry, pharmacology, antibacterial activity and dye. Phytochemistry Phytochemical screening of Bixa orellana carried out so far has led to the isolation and identification of a number of structurally diverse chemical compounds. There are many chemical constituents including carotenoids, apocarotenoids, sterols, aliphatic compounds, monoterpenes and sesquiterpenes, triterpenoids, and other miscellaneous compounds that have been identified and isolated mostly from seeds, seed coats and leaves of this plant. In this part of the review, we describe the major chemical constituents, their structures and their isolation from different parts of this plant, Table 1. Carotenoids The main compounds found in B. orellana plant are carotenoids and apocarotenoids. Several phytochemical studies have been performed on isolation and identification of carotenoids and apocarotenoids of various extracts. Most of the carote- noids have been isolated from seed and seed coats. Bixin (1) [methylhydrogen-(90 Z)-6,60 -diapocarotene-6,60 -dioate] is the major carotenoid compound present in B. orellana seed coat and accounts for 80% in addition to the presence of other carotenoids in trace amounts [20,21]. Tirimanna identified and isolated b-carotene, cryptoxanthin, lutein (2), zeaxanthin (3), and methyl bixin (4) in addition to bixin and nor-bixin (5) from seeds by thin layer chromatography [19]. Chemical investigation of methanol seed extract has resulted in the identification of the apocarotenoids methyl bixin (dimethylhydrogen(90 Z)-6,60 -diapocarotene-6,60 -dioate) (4) [22]. In a series of phytochemical investigations Mercadante et al. reported a number of apocarotenoids from B. orellana seed coat. In 1996, they successfully isolated methyl-90 Z-apo-60 -lycopenoate (6) from the seed coats [23]. Methyl-(7Z,9Z,90 Z)-apo-60 -lycopenoate (7), methyl-(9Z)apo-80 -lycopenoate (8), methyl-(all-E)-apo-80 -lycopenoate (9), and methyl-(all-E)-apo-60 -lycopenoate (10) were also isolated from seed coat of B. orellana [17]. In 1997, six minor diapocarotenoids and one C14-carotenoid derivative were isolated from the seed coat and were named dimethyl-(9Z,90 Z)-6,60 -dia pocarotene-6,60 -dioate (4), methyl-(9Z)-100 -oxo-6,100 -diapocar oene-6-oate (11), methyl-(9Z)-60 -oxo-6,50 -diapocaroene-6-oate (12), methyl-(9Z)-60 -oxo-6,60 -diapocaroene-6-oate (13), and m ethyl-(4Z)-4,8-dimethyl-12-oxododecyl-2,4,6,8,10-pentaenoate (14) [24]. In another study conducted two years later, 6-geranyl geranyl-80 -methyl-6,80 -diapocaroten-6,80 -dioate (15), 6-geranyl geranyl-60 -methyl(90 Z)-6,60 -diapocaroten-6,60 -dioate (16) and 6-geranylgeranyl-60 -methyl-6,60 -diapocaroten-6,60 -dioate (17) were also successfully obtained from seeds of B. orellana [8]. The chemical structures of isolated carotenoids are shown in Fig. 2. Terpenoids and terpenes Terpenoids mainly C20-terpene alcohol all-geranylgeraniol as a major chemical component in Bixa orellena were isolated 502 Table 1 S. no. S.ul-Islam et al. Chemical constituents of Bixa orellana. Classification Components Plant part References Methylhydrogen-(90 Z)-6,60 -diapocarotene-6, 60 -dioate (Bixin) Lutein Zeaxanthin Dimethyl-(9Z,90 Z)-6,60 -diapocarotene-6,60 -dioate NorBixin Methyl (90 Z)-apo-60 -lycopenoate Methyl-(7Z,9Z,90 Z)-apo-60 -lycopenoate Methyl-(9Z)-apo-80 -lycopenoate Methyl-(all-E)-apo-80 -lycopenoate Methyl-(all-E)-apo-60 -lycopenoate Methyl (9Z)-100 -oxo-6,100 -diapocaroten-6-oate Methyl (9Z)-60 -oxo-6,50 -diapocaroten-6-oate Methyl (9Z)-60 -oxo-6,60 -dioapocarotene-6-oate Methyl-(4Z)-4,8-dimethyl-12-oxododecyl-2,4,6,8,10-pentaenoate 6-Geranylgeranyl-80 -methyl-6, 80 -diapocaroten-6, 80 -dioate 6-Geranylgeranyl-60 -methyl (90 Z)-6, 60 -diapocaroten-6,60 -dioate 6-Geranylgeranyl-60 -methyl-6,60 -diapocaroten-6, 60 -dioate Trans-bixin Seed coat Seeds Seeds Seed coat Seeds Seed coat Seed coat Seed coat Seed coat Seed coat Seeds Seeds Seeds Seeds Seeds Seeds Seeds Seeds [22] [19] [19] [22,24] [86] [23] [23,24] [23] [23] [17] [24] [24] [24] [24] [8] [8] [8] [103] Farnesylacetone Geranylgeranyl octadecanoate Geranylgeranyl formate d-Tocotrienol b-Tocotrienol Seeds Seeds Seeds Seeds Seeds [22] [22] [22] [25] [25] b-Humulene a-Carpophyllene a-Copaene a-Elemene Cis-ocimene Tomentosic acid Roots Leaves and roots Leaves and roots Leaves Leaves Roots [26] [12,26] [12,26] [12] [12] [104] (Z,E)- farnesyl acetate (11.6%) Occidentalol acetate (9.7%) Spathulenol (9.6%) Ishwarane (9.1%) Seed oil Seed oil Roots, seed oil Seed oil [27] [27] [26,27] [27,105] Acetic acid 2-Butanamine Pentanoic acid Phenol Pantolactone Benzoic acid Phytol Stigmasterol Sitosterol Leucocyanidin Ellagic acid Luteolin Apigenin Roots Roots Roots Roots Roots Roots Leaves Leaves Leaves Leaves Leaves Leaves Leaves [10] [10] [10] [10] [10] [10] [37] [37] [37] [28] [28] [28] [28] Carotenoids (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) Terpenoids (19) (20) (21) (22) (23) Terpenes (24) (25) (26) (27) (28) (29) Volatile compounds (30) (31) (32) (33) Other compounds (34) (35) (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) by Jondiko and Pattenden. Other terpenes that were isolated and characterized for the first time include farnesylacetone (19), geranylgeranyl octadecanoate (20), geranylgeranyl formate (21), d-tocotrienol (22) and b-tocotrienol (23) [22]. Frega et al. reported the presence of tocotrienols mainly dtocotrienol from lipid fraction of annatto seeds using thinlayer chromatography. Sesquiterpenes are also a major group of volatile compounds found in annatto extracts [25]. In one of the recent studies on annatto b-humulene (24) was the major compound present in annatto extract along with its isomer caryophyllene (25) which was present in smaller quantities. Several other sesquiterpenes found usually in water-soluble as well as in oil-soluble extracts include a-copaene (26), and a-elemene (27) [26]. Figs. 3 and 4 depict the chemical structures for all the isolated terpenes and terpenoids. Phytochemistry and biological activities of Bixa orellana Fig. 2 Chemical structures of carotenoids. 503 504 S.ul-Islam et al. Fig 2. (continued) Volatile compounds (essential oils) Table 1 presents a list of volatile compounds isolated from different parts of B. orellana. Up to now very few studies have been performed on the extraction and identification of volatile compounds from Bixa orellana. One hundred and seven compounds from oil and water soluble annatto extracts were detected by GC/MS in one of the recent studies carried by Phytochemistry and biological activities of Bixa orellana 505 characterized from seed oil were (Z,E)-farnesyl acetate (30) (11.6%), occidentalol acetate (31) (9.7%), spathulenol (32) (9.6%) and ishwarane (33) (9.1%) [27]. Chemical structures are shown in Figs. 5 and 6. Other miscellaneous compounds Table 1 lists some other miscellaneous compounds and their chemical structures are given in Fig. 6. GC/MS analysis showed the presence of six major components 2-butanamine (35), acetic acid, pentanoic acid (36), phenol (37), pantolactone (38) and benzoic (39) [10]. Three new flavone bisulfates have been found in the leaves of Bixa orellana. They have been identified as 7-bisulfates of epigenin and luteolin and 8-bisulfate of hypolaetin, confirmed by synthesis [28]. Pharmacodynamics and potential applications Fig. 3 Chemical structures of terpenoids. Galindo-Cuspinera et al. using dynamic headspace-solvent desorption technique. The main volatile compounds identified were pentanol and hexanol, 3-hexenol, nonanal, hexanal, and 2-heptenal, dimethylcyclohexane, dimethylhexane and 2-methylheptane, 3-penten-2-one, 3-octanone, 4-methyl-3-penten2-one, 4-hydroxy-4-methyl-2-pentanone, 6-methyl-5-hepten2-one, acetic acid, ethyl butyrate, 1,2-propanediol-2-acetate, 3-methylpyridine, p-xylene and toluene, d-elemene, a-pinene, limonene, b-myrcene, eucalyptol, b-phellandrene, and terpinen-4-ol [26]. Pino and Correa detected thirty-five compounds from seed oil of this plant using GC/MS technique. The major components Fig. 4 Many pharmacological investigations have been initiated by researchers all over the globe over the past few decades due to varied ethnomedical uses of B. orellana. A wide range of biological activities has been described in the literature including antibacterial and antifungal activities, antioxidant and free radical scavenging activities, anti-inflammatory activity, anticarcinogenic activity, enhanced gastrointestinal motility, and neuropharmacological and anticonvulsant activities through detailed observation with respect to its ethnomedical uses. An overview of pharmacological and therapeutic profile of B. orellana is described below in detail and briefly summarized in Table 2. Antibacterial and antifungal activities Inhibitory actions of the methanol leaf and seed extracts were tested against bacterial and fungal strains. Leaf (MIC = 1000 lg/ml) extracts were more effective and possessed antimicrobial activity against a wide variety of bacteria and fungi, showing greatest activity against Salmonella typhi (MIC = 31.25 lg/mL) and Acinetobacter Chemical structures of terpenes. 506 S.ul-Islam et al. Fig. 5 Fig. 6 Chemical structures of volatile compounds. Chemical structures of other compounds. Pharmacological effects of Bixa orellana. Antibacterial and antifungal activity Antioxidant and free radical scavenging activity Anti-inflammatory activity Details Extracts/compounds In vitro/In vivo References – In vitro [32] 24 mg/mL In vitro [33] – In vitro [14] – – 2.0 mg/mL 5 mg/mL 3.0 lg/mL – In vitro [37] [3] In vitro In vitro [40] [42] 5.5–48.9% relative to 0.25 and 2.5 lg/mL ascorbic acid 2.9–41.5% 33% 2.5 or 5.0 mg/kg In vitro [44] In vitro [45] – 150 mg/kg In vitro [46] – 50 mg/kg and 150 mg/kg In vitro [46] – 50 mg/kg and 150 mg/kg In vitro [47] – – 200 mg/kg and 400 mg/kg In vitro – In vitro [48] [10] 19% and 33.60% 50 lg/mL [50] 21.50, 20.00, 19.50, 17.00, 19.00, 22.50, 22.00 (leave extract) and 20.00, 17.00, 19.00, 14.50, 19.00, 18.00, 20.00 (seed extract), respectively. 21.6 15.8 15.20 10-14 >14 – 17 15–17 11.0, 1.0, 3.0 and 7.0, respectively In vitro 507  Broad spectrum antibacterial activity against Ethanolic leaves and seeds Bacillus subtilis, Staphylococcus aureus, Strep- extract tococcus pyogenes, Salmonella typhi, Pseudomonas aeruginosa, Escherichia coli and Candida albicans  Showed differential in vitro antimicrobial activity against B. pumilus Ethanolic leave extract Ethanolic hypocotyls extract Ethanolic root extract Acetone extracts DMSO extracts Dichloromethane/ ishwarane Methanolic crude extract Hexane extract 95% ethanol leaves extract  Activity against reactive oxygen and nitrogen Ethyl acetate extract, composed species (H2O2, HOCl, O2, .NO, and ONOO of hypolaetin and caffeoyl acid derivative species)  antioxidant activity via 2,2-diphenyl-1-picryl- Seed extract hydrazyl (DPPH) radical scavenging activity and iron (III) oxide reducing power using Bixin ascorbic acid (vitamin C) as a reference standard  Reduced total number of chromosome aberrations, inhibited the increase in lipid peroxidation, and renal glutathione depletion induced by cisplatin  Effect of aqueous extract of Bixa orellana on Aqueous extract histamine-induced paw edema in rat models  Significantly decrease carageenan, histamine, Pretreatment of aqueous leaf serotonin and bradykinin induced acute and extract After treatment of leaf extract chronic rat paw edema  Inhibits bradykinin-induced inflammation. (lyophilized) and decreases nitric oxide production and vas- Leaf extract Aqueous extract (2-butanamine, cular endothelial growth factor (VEGF)  Produced partial gastroprotective effects acetic acid, pentanoic acid, against 96% ethanol induced injury and phenol, pantolactone and benzoic acid) reduced migration of pro-inflammatory cells  Reduced paw volumes and almost normalized Bixin peritoneal vascular permeability, suspected to be aided by the suppression of other permeability-regulating substances (NO and VEGF)  Inhibited COX-2 and COX-1 enzyme Potency of MIC/dose level extracts/compounds zone of inhibition (mm)/ % Inhibition Phytochemistry and biological activities of Bixa orellana Table 2 Pharmacological effects 508 Table 2 (continued) Pharmacological effects Anti carcinogenic activity Gastrointestinal motility Neuropharmacological activity and Anticonvulsant activity Analgesic activity and Antidiarrheal activity Other pharmacological effects Details Potency of MIC/dose level extracts/compounds zone of inhibition (mm)/ % Inhibition Bixin – 33, 49, 45, and 39 lg/mL – [50] Methanol leaves extract Cis-bixin 52%, 57% and 53% – 500 mg/kg 10–50 lM In vitro In vitro [52] [53] Dichloromethane extract of the air-dried leaves (Ishwarane) Ishwarane Methanol leaves extract (88.38 ± 13.59%) 25, 50, and 100 mg/kg In vitro [37] 79.55% 50 mg/kg 125, 250 and 500 mg/kg 500 mg/kg In vitro In vitro [37] [54] 500 mg/kg In vitro [54] Leaves extract Leaves extract In vitro/In vivo References 250 and 500 mg/kg – [54] Leaves extract 58.45 min (control group) 76.70 and 90.82 min 7.33 and 10.68 min 250 and 500 mg/kg – [54] Methanol leaves extracts 43.60% – In vitro [55] Methanol leaves extracts – 22.36 lg/mL In vitro [54] Methanol extract – 500 mg/kg In vitro [58] Ethanol extracts Whole plant extracts (Root and leaf extract) – 6.0 and 17.40 – – In vitro In vitro [59,60] [61] S.ul-Islam et al.  The cell proliferation inhibitory effects against colon, CNS, stomach, and lung cancer cell lines  Decreased carbon tetrachloride hepatoprotection in rats with decrease in the elevations of liver alanine aminotransferase (ALT), aspartate aminotransferase (AST) and cholesterol  Selectively killed freshly collected patient multiple myeloma cells and highly drug-resistant multiple myeloma cell lines  Prophylactic and gastrointestinal motility  Resulted in a more propulsive movement of the gastrointestinal tract  Delayed intestinal transit of charcoal meal in mice to a statistically significant level (p < 0.01)  Pentobarbitone-induced hypnosis test: Leaves extract was found to reduce the time for onset of sleep compared to the control with results statistically significant  Increases duration of sleep in test animals compared to the control  Strychnine-induced anticonvulsant test: increased the average survival time  Oral glucose tolerance test: lower blood glucose level when administered 45 min before glucose load  Inhibited caster-oil induced diarrhea in mice: Significant decrease in the total number of stools and dose-dependently the total number of feces and the total number of wet feces.  Diuretic effect with a significant increase in urine volume and levels of sodium, potassium and chloride  Used to neutralize snake venom and prevents associated adverse effects  provide partial protection against the edema forming activity and lethality in mice against Bothrops asper and B. atrox venom and potent antigonorrheal activity Extracts/compounds