1 Achiote () orellana

Common names: Achiote, annatto, annatto , arnato tree, lipstick, lipstick tree. Vernacular/regional names: Arabic: atshyut, galuga; Bulgarian: achiote, ačiote; Chinese: hong mu, yan zhi mu, yan zhi shu; Czech: annata; Danish: annatobusken, orleantræ, smørfarve- træ; Dutch: achiote, anatto, annotto, orleaan, rocou; Estonian: annatopõõsa; Finnish: annaatto; German: anatto, anat- tosamen, anattostrauch, annatto; Hindi: induriya, sindhuri; Hungarian: bjoul, orleánfa, orleánfa, ruku; Indonesia: kes- umba, kesumba kling; Italian: annatto, anotto; Japanese: achiote, anatoo, anatto, be-ni-no-ki; Korean: a chi o te, a na to, a-ci-o-te, anato, bik sa sok; Lao: dok kham, sa ti; Malay: jarak belanda, kunyit jawa; Polish: arnota; Portuguese: açafroa, aça- froa do brasil, acafroeira da terra anato, colorau, urucú, urucú- bravo, urucú, urucum; Russian: achiote, annatto; Sanskrit: rakhtabija, shonapushpi, sinduri; Spanish: achihuite achiote, Name currently accepted: achiote caspi, achiotl, achote; Swedish: annattobuske; Turkish: Authority: Linn. arnatto; Vietnamese: diêù nhuôm, ht iu màu (Katzer, 2012; Taxonomic serial no.: 22251 (ITIS, 2016) Lim, 2012; Anon., 2013a). A ­detailed listing of the vernacular names can be seen in Lim (2012). Synonyms: Bixa americana Poir, Bixa katangensis Delpierre, Bixa odorata R. Cuiz & Pav ex G. Don., Bixa orellana var. leio­ carpa (Kuntze) Standl and L.O. Williams, Bixa orellana f. leio­ carpa (Kuntze) J.F. Macbr., Bixa purpurea Sweet., Bixa tinctaria Introduction Salisb., Bixa upatensis Ram Goyena, Orellana americana (Poir.) Kuntze, Orellana americana var. leiocarpa Kuntze, Orellana Achiote, more commonly known as annatto in the English- orellana (L.) Kuntze (Anon., 2010). speaking world, is a native of tropical America from where it has Family: (Kingdom: Plantae; Subkingdom: spread to most of the tropical and subtropical world and natural- Viridiplantae; Infrakingdom: Streptophyta; Superdivision: ized. The seeds of this tree are covered with bright yellowish-or- Embryophyta; Division: Tracheophyta; Subdivision: Spermato­ ange to reddish- powder (called pulp) that forms a widely phytina; Class: Magnoliopsida; Superorder: Rosanae; Order: used food colour. It is distributed as well as cultivated widely in ; Family: Bixaceae; : Bixa; Species: orellana; its native land in Central and . As an introduced Binomial: Bixa orellana L.). it is cultivated in many countries, including Angola, Brunei,

© P.N. Ravindran 2017. The Encyclopedia of & (P.N. Ravindran) 1 2 Achiote

Cambodia, Dominican Republic, , Indonesia, , from the seeds. They are: methyl (7Z, 9Z, 9′Z )-apo-6′-­ Kenya, Laos, Malaysia, Myanmar, the , , lycopenoate, methyl (9Z )-apo-8′-lycopenoate, methyl 1(all-E)- Tanzania, Thailand, the USA, Vietnam and Zanzibar. The an- apo-8′-lycopenoate, methyl (all-E)-8-apo-beta-carotene-8′-oate, cient people of Central and South America, especially the Mayas methyl (all-E)-apo-6′-lycopenoate, 6-geranylgeranyl-8′-methyl- and , regarded achiote extract as a substitute for blood and 6, 8′diapocaroten-6-8′dioate, 6′-geranylgeranyl-6′-methyl-(9Z)-6, 6′- hence held it sacred. The extract was used as an ink and to write diapocaroten-6-6′-dioate and 6-geranylgeranyl-6′-methyl-6-6′- the ancient scriptures of the Mayas. It was used as a beauty aid, diapocaroten-6-6′-dioate. Seeds also contain the C-40 carotenes as hair dye and lip paint, hence the common name ‘lipstick tree’ such as phytene, phytofluene, z-carotene and neurosporine (Jansen, 2005; Taylor, 2005; Ravindran et al., 2012). (Lim, 2012). More than 100 volatile compounds have been detected in aqueous and organic extracts and more than 50 of these have Botanical Notes already been identified. Thirty-five components were identi- fied in the seed oil. Of these, (Z,E)-farnesyl acetate (11.6%), Achiote or annatto tree is a large evergreen reaching the occidentalol acetate (9.7%), spathulenol (9.6%) and ishwarane stature of a small tree on full growth, at which it is about 7–8 m (9.1%) are the major components (Pino and Correa, 2003). high. Leaves are ovate, simple, spirally arranged, stipulate, Galindo-Cuspinera et al. (2002) reported the presence of 107 more or less cordate to truncate at the base, apex acuminate, volatile compounds in oil-soluble and water-soluble achiote ex- glabrous and are borne on long petioles. Flowers are in terminal tracts. They identified 51 aromatic compounds and also tentatively panicles carrying up to about 50 flowers. Flowers are fragrant, identified the compounds responsible for the characteristic fra- each flower with 5–6 glands. are 4–5, free, obovate, ca- grance. The following classes of compounds were identified in ducous; petals are 4–7, obovate, pinkish, whitish or purplish the aqueous and oily fractions: alcohols, aldehydes, alkanes, tinged. Stamens are numerous, anthers violet. The pistil is alkenes, ketones, esters and acids, heterocyclic compounds, about 1.5–1.6 cm long, one-celled, ovary superior, and stigma monoterpenes (geraniol, linalool) and sesquiterpenes. Seed short, two-lobed. Achiote flowers are bee-pollinated; fruit takes volatile oil components are mainly: bornyl acetate, α-caryophyllene, 5–6 months to reach maturity. Fruit is a capsule, hemispherical, copaene, α-cubebene, (+)-cyclosativene, geranyl phenylacetate, ovoid or broadly elongated, red to reddish purple or green 1-heptanetiol, 3-methylpyridine, 4-methylpyridine, γ-elemene, when mature and covered with bristles. Seeds are numerous in β-humulene, isoledene, β-pinene, seline-6-en-4-ol, δ-selinene, each capsule, obovoid and covered with a reddish-orange pow- (−)-spathulenol and (+)-ylangene (Alves de Lima et al., 2003; dered seed coat. Chromosome numbers reported are 2n = 14, Lim, 2012; Vilar et al., 2014). Demczuk and Ribani (2015) gave 16 (Iqbal, 1993; Green, 1995; Jansen, 2005; Orwa et al., 2009; an update on the chemistry and use of achiote. Lim, 2012; IPCN, 2016). The dye obtained by water extraction is mainly nor-bixin Achiote can be propagated either using seeds or and both the α- and β-isomers of nor-bixin are present in the vegetatively using stem cuttings, budding, air-layering and also extract. Bixin [α-bixin or (−)-bixin] present in the seed is un- through tissue culture methods. Genetic variability exists with stable and gets converted to its stable isomer iso-bixin (or trans- respect to fruit colour, shape, flower colour and also in the con- bixin or β-bixin). Bixin is formed as the monomethyl ether of tent of pigments. Pigment content is related to fruit shape; nor-bixin, a dicarboxylic acid, so gets easily hydrolysed back to hemispherical fruit has about 5% pigments, conical fruit about its dicarboxylic acid form, nor-bixin, which happens during the 3–3.58% and oval fruit has around 1.5–2%. The plant starts alkali extraction process. Nor-bixin is present in the plant tissue bearing fruit in about 3 years; yield of a mature tree varies in its potassium salt form. The oil extract of the seed contains from 300 to 600 kg per ha (Iqbal, 1993; Jansen, 2005; Orwa free bixin. In the free acid state, both bixin and nor-bixin are et al., 2009). insoluble in water but readily soluble in organic and in aqueous alkaline solutions; solubility is highest at pH 8 with decreased stability at pH 4–8 (Preston and Rickard, 1980; Khan and Abourashed, 2010). Giridhar et al. (2014) reviewed the ex- Chemical Notes traction, analysis and processing of achiote dye. Scotter (2009) reviewed in detail the colour chemistry and technology of The orange-red (or the yellowish-orange) colour of the seed achiote. coat is contributed by the apo-, bixin (′Z-6,6′-diapo- Achiote leaves on analysis gave flavonoid bisulfates (Harborne, carotene-6,6′-dioate) and its derivative nor-bixin. Nor-bixin is 1975), sterols, tannins, saponins (Shilpi et al., 2006) and an es- formed through the removal of the methyl ester moiety from sential oil comprising mainly sesquiterpenes with ishwarane as bixin. Besides these two, other phytochemicals present are: iso- the major compound (Lawrence and Hogg, 1973). Radhika and bixin, beta-carotene, cryptoxanthin, lutein, zeaxanthin, orellin, Nasreen Begum (2010) reported the presence of phytochemi- bixein, bixol, bixaghanene, crocetin, ishwarane, ellagic acid, cals such as carbohydrates, steroids, alkaloids, proteins, flavon- salicylic acid, threonine, tomentosic acid, tryptophan and oids, terpenoids, phenolics, tannins and glycosides in achiote phenylalanine. Analytical data on achiote seeds gave the fol- leaves. The roots have been found to contain the triterpene lowing information on the composition: 40–45% starch, 3.5–5.5% tomentosic acid (Schneider et al., 1965). Bixaghanene, bixein, sucrose, 0.3–0.9% , 3% fixed oil, 4.5–5.5% pig- bixol, crocetin, ellagic acid, isobixin, phenylalanine, salicylic ments and 13–16% protein (Taylor, 2005; Vilar et al., 2014). acid, threonine and tryptophan are the other phytochemicals Mercadante et al. (1997, 1999) isolated eight apocarotenoids present (Venugopalan et al., 2011). Achiote 3

Functional Properties Medicinal uses

The functional properties of achiote seed have been summar- Duke (2002) has provided a list of ailments for which achiote is ized by INCHEM (2004), Khan and Abourashed (2010), indicated. Leaves are applied to the forehead or to sprained Lim (2012), Ravindran et al. (2012) and Vilar et al. (2014). areas to relieve aches. A decoction of leaves is gargled as a cure Duke (2002) has compiled a list of functional properties of for mouth and throat infections, and given internally to relieve achiote. An excellent holistic review is that of Ulbricht et al. colic and to get rid of worms in children. A root decoction is (2012). The major properties are mentioned below. taken orally to control asthma. A macerated seed decoction is taken orally for relief of fever, and the pulp surrounding the Aldose reductase activity: Hot water extract of achiote was shown seed is made into an astringent drink to treat dysentery and to possess potent inhibitory activity on lens aldose reductase kidney infection. Oliguria and jaundice are treated using root (Terashima et al., 1991). teas; infusions of root in water or rum are used to treat venereal Antimicrobial activity: Achiote tree bark was shown to possess diseases. The dye is used as an antidote for prussic acid very high bactericidal activity against Gonococcus (Caceres (hydrogen cyanide) poisoning caused by consuming poorly et al., 1995). Leaf and seed extracts have potent antimicrobial cooked cassava (Manihot esculenta). Seeds are used as an expec- activity, leaf extract being the most effective against Bacillus torant (Taylor, 2005; Orwa et al., 2009; Anon., 2013b). pumilus (Castello et al., 2002; Fleischer et al., 2003). Methanol extract of leaf is strongly bactericidal against the causal agents of dysentery and diarrhoea, including Shigella dysenteriae (Shilpi et al., 2006). Culinary uses and products Anti-inflammatory activity: A study reported significant anti-inflammatory activity of achiote leaf extract against brady- Achiote dye (known more commonly as annatto dye) is a widely kinin-induced inflammation and also suppressed the produc- used food colourant that carries the international code numbers tion of nitric oxide (Yoke Keong et al., 2011). CI# 75120, CAS# 1393-63-1 and EU# E160 (b) (Smith, Anti-diabetic activity: Ponnuswamy et al. (2011) reported the 2006). Owing to its -soluble nature, achiote pigment is widely inhibition of human pancreatic amylase by the methanol ex- used for imparting a red to orange–yellow colour to a variety of tract of leaves indicating the potential of this plant for foods such as , , oils, , ice cream, candy, post-prandial glycaemic control. Seed extract exhibited anti-­ bakery products and rice. The widest use is in the dairy sector, diabetic activity; when tested on dogs it lowered blood glucose where it is used to colour cheese, butter and other such level and increased plasma insulin concentration. Seed extract products. enhanced insulin binding on the insulin receptor as a result of In , the seeds are fried in fat and after re- elevated affinity of the ligand for the receptor and by the moving the seed the coloured oil is used with rice, gravies and stimulation of peripheral utilization of glucose (Russell et al., stew to impart a beautiful golden yellow colour to the dishes. 2005, 2008). The famous Mexican mix known as recado contains Anti-venom activity: An ethanolic extract of leaves was shown to mostly achiote pigments that impart a brilliant colour to meat neutralize the defibrinating and coagulant effects of venom and after marinating it. The Spanish were responsible for introdu- to reduce oedema resulting from Bothrops atrox (a species of cing achiote to the Philippines and Indonesia, where it formed poisonous pit viper) venom. Achiote leaf extract also caused an ingredient in their culinary art. In the Philippines the seed 45–80% neutralization of enzymatic effects of the venom powder is added to stews, and soups, and it is an essen- (Otero et al., 2000; Núñez et al., 2004). tial ingredient in meat marinating mixes. Fresh seed extract in Anti-oxidant activity: A number of studies have indicated a water is also used for colouring rice preparations. strong anti-oxidant effect of achiote seeds, which is attributed Achiote seeds and and powder are widely used in mainly to norbixin (Kovary et al., 2001; Oboh et al., 2011). Vietnam for imparting attractive hues to meat. Batter is col- Lipid-lowering activity: In a preliminary study, Ferreira et al. oured with achiote dye, which then imparts a golden yellow (2013) reported a triglyceride-lowering activity of achiote seed colour to the fried items. Katzer (2012) has summarized the use extract. of achiote in culinary art in various countries. Toxicology: Very rare human allergic reactions have been re- An FAO document on annatto dye has provided the fol- ported for achiote dye. The reactions include IgE-mediated lowing information on the food uses of achiote (Smith, 2006, anaphylaxis, anti-oedema and urticaria (Khan and Auborashed, p. 21). ‘Oil-based achiote preparations are commonly used to 2010). colour foods with high fat content, such as or margarine/shortening (shortening is a process for converting a fat to a solid product at room temperature and used to make crumbly pastry). They are also used extensively in bakery prod- Uses ucts, biscuit fillings, popcorn and snack foods, , dressings and cream desserts. Emulsified achiote colours, in general, may In its native countries, achiote has been put to a variety of uses. advantageously be used in such products as processed cheese, The Agroforestree database of the World Agroforestry Centre ice cream, soup, confectionery and dairy products. The more and the Raintree Tropical Plant Database have provided lists of acid stable emulsified achiote finds its use in such applications uses of achiote (Taylor, 2005; Orwa et al., 2009; Anon., 2013b). as juices, liqueurs, transparent jellies and gelatinous desserts. 4 Achiote

Water-soluble achiote dye has traditionally been used for col- yields a water-soluble gum that is similar to gum arabic. The dye ouring cheese, but is now used in many other applications. As from the seed was used by Native Americans as war paint and was the basic water-soluble achiote is not acid-proof (precipitation used in dying wool, cotton and silk, but the colour rapidly fades below pH 7), it is normally not used in clear acidic solutions when exposed to light and air. The dye is used in manufacturing (clear soft drinks without pulp), but it is very suitable in acidic cosmetics. Seeds contain a characteristic, pleasant-smelling oil. foodstuffs having a matrix or solid structure. Some present ap- A waxy substance that has a paralytic action on mammalian plications of the water soluble achiote colour include intestinal parasites is present in the seed coat. Bixin extracted casing, , puddings, tomato , breakfast cereals, from the seed coat is used in India as an insect repellent (Taylor, butter desserts, fillings, smoked fish and pet food. 2005; Orwa et al., 2009; Lim, 2012; Anon., 2013b). The basic nature of achiote extracts makes it suitable in products where the pigment is absorbed by protein and/or starch. These characteristics are extremely valuable for use of Products achiote in products like cheese and breakfast cereals. As the water-soluble achiote also exists in a powdered form, applica- The following categories are recognized internationally (Smith, tions can be extended to powdered products like instant des- 2006): serts, dip mixes, health food powders and fibre tablets. These products will become yellow or orange yellow when reconsti- Annatto A: -extracted bixin paste, solvent removed tuted. Solvent-extracted achiote is used in a variety of ways. (min. 20% bixin; now not an item of trade). Solvent extraction is used to produce achiote of greater than Annatto B: Solvent-extracted crystallized bixin, dried crystals 90% purity. The solvent extract is then subsequently dissolved (min. 80% bixin). or suspended in oil, aqueous alkali with or without a carrier Annatto C: Solvent-extracted crystallized bixin, saponified, such as propylene glycol to yield the final application form. hydrolysed, acid-precipitated, washed and dried (min. 70% This type of product is very useful when formulating colour- bixin). ants with special functions. Good examples would be acid and Annatto D: Oil-processed bixin suspension (no solvent used) brine-stabilized achiote, food products where light tolerance (min. 10% bixin). and long shelf-life are required and special colour blends con- Annatto E: Aqueous-processed bixin, dried into a granular taining achiote and other natural colourant, such as curcumin, powder (min. 25% bixin). and carmine’(Smith, 2006). Annatto F: Alkali-processed norbixin, acid-precipitated and There are many recipes from countries that make use of dried into a granular powder. The pH of a 10% solution is less achiote seed, its extract and dye. Information on such recipes is than 5 (min. 35% bixin). available widely in the public domain, as well as in recipe books Annatto G: Alkali-processed norbixin, mildly alkaline, dried (Anon., 2015, 2016a,b). (no acid-precipitation step) (min. 15% bixin).

Other uses Safety Issues

Achiote dye is used as an ingredient in hair oils, shoe polish, There is no evidence to indicate any toxic effect of achiote soap, cosmetics and pharmaceutical products. It can also be (annatto) dye, except for the rare mild allergic reactions re- used as an adsorption-indicator in argentometric titrations. ported in some sensitive individuals. A well-defined WHO/ Bixa meal, which remains after extraction of the pigment FAO jointly sponsored investigation indicated the safety of from the seed, is a useful additive to poultry feed and can replace achiote dye. There is no cumulative action even at 15% levels 30% of the in the food. The seed embryo contains a poi- in vegetable oil or 10% in water. Extensive studies are indica- sonous alkaloid, however, so it is not wise to use the residues from tive of the absolute safety of annatto dye (Anon., 1974). The the extraction process directly. The flowers are an important No-Observed-Adverse-Effect-Level (NOAEL) was judged to source of nectar for honey production. It is a good fuel wood; it be a dietary level of 0.1% (69 mg/kg body weight/day for is said that fire can be started by the friction of two pieces of the males, 76 mg/kg body weight/day for females) of annatto ex- soft wood. Fibre for rope-making has been obtained from the tract (norbixin) under experimental conditions (Hagiwara bark of the achiote tree. Bark from the branches of the et al., 2003).

References

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