Bitter Orange (Citrus Aurantium) Powder

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Whole herbs and extracts are both very different products.

Whole botanicals in some cases contain every part of a botanical including roots or stems while extract contains a specific botanical compound and is measured to a specific amount. 

Extracts come with standards set by potency percentage so your order will always match what was advertised.

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A whole ingredient contains the entire botanical, including the roots, stem, flower etc.

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Herbal extracts are often 'standardized' to contain a certain amount of a compound or active ingredient. Standardization ensures that every batch of a botanical extract contains the same amount of the advertised compound. For example, Acerola 10% may be standardized to 10% vitamin C. Every batch of that product will have at least 10% of that active compound.

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If it's a 4:1 extract, for example, that means that four parts of the original plant are going into one part of the final extract, making it a concentrated powder.

Think of it this way: Ratio of dry plant material (X) to final extract quantity(Y).

X : Y

Y = weight of dry plant material

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The concept here is that the essential activity of the dry plant material (X) is found in the quantity of extract (Y). Or in other words, Y quantity of the extract is equivalent to X quantity of the dry plant.

For example, a botanical ingredient listed as a 4:1 extract means that 4 kg of raw herbs were extracted down to 1 kg of dried powdered extract.

Citrus genus is a prominent staple crop globally. Long-term breeding and much hybridization engendered a myriad of species, each characterized by a specific metabolism generating different secondary metabolites. Citrus aurantium L., commonly recognized as sour or bitter orange, can exceptionally be distinguished from other Citrus species by unique characteristics. It is a fruit with distinctive flavor, rich in nutrients and phytochemicals which possess different health benefits. This paper presents an overview of the most recent studies done on the matter. It intends to provide an in-depth understanding of the biological activities and medicinal uses of active constituents existing in C. aurantium. Every plant part is first discussed separately with regards to its content in active constituents. All extraction methods, their concepts and yields, used to recover these valuable molecules from their original plant matrix are thoroughly reported.

Citrus aurantium L., also known as sour orange, bitter orange, Seville orange, or bigarade, is an evergreen tree that can grow up to 5 meters tall. Renowned for its scented white flowers, it is believed to have originated in eastern Africa and Syria and was cultivated in the United States, Spain, and Italy [ 8 ]. A large number of studies were carried out on the bioactivity of C. aurantium compounds. The focus of this review article is to compile and document the recent studies performed over the last decade on the bioactive molecules existing in C. aurantium plant, unraveling their biological effects and potential medicinal virtues. Furthermore, methods used for their extraction from the original plant parts, are comprehensively overviewed.

Citrus, genus of the family Rutaceae, includes various species of diverse sizes and forms, commonly known as lemons, limes, oranges, mandarins, citrons and grapefruits [ 1 , 2 ]. They are one of the central horticultural crops with universal agricultural production with '100 million tons per year [ 3 ]. Previously, Citrus plants were associated with herbal medicine in many Asian countries such as Japan, China, and Korea. They are in recent years commercialized for their fruits and juice, or used as additives in several industries [ 4 ]. Other than being rich in vitamin C and vitamins B, Citrus fruits contain minerals, macronutrients such as carbohydrates, dietary fibers, crude proteins, lipids, and phenolic compounds with important health-promoting properties [ 5 , 6 ]. On the other hand, essential oils obtained from Citrus species are extensively used in food and beverages, perfumes, pharmaceutical, and cosmetic industries [ 7 ].

2. C. aurantium Active Constituents

Plant secondary metabolites, or phytochemicals, have well-established properties that are of pivotal importance to human health, comprising, among others, anti-cancer, antiproliferative, hypolipidemic, and cardio-protective activities [8]. Their potent antioxidant activity is evidently linked to their natural ability to hunt free radicals and disrupt radical chains. The C. aurantium plant is teeming with phytochemicals. Flavonoids, the major bioactive compounds contained in C. aurantium, are grouped into flavanones, flavones and flavonols. Limonoids, such as limonin and nomilin, and alkaloids, such as p-synephrine, are also encountered [9]. In the following, and as shown in , C. aurantium parts including juice, flowers, seeds, leaves and peels are methodically discussed regarding their content in bioactive molecules. It is noteworthy to mention that the chemical composition or the percentage of biomolecules is obviously affected by the geographical area, growing season, and the period of harvest.

2.1. C. aurantium Juice

C. aurantium juice is mainly used in salad dressings as an alternative to lemon juice, providing its typical flavor [10]. C. aurantium juice was reported to contain 86% of phenolic acids out of total phenolic compounds [11]. In a study on Tunisian bitter orange, Jabri Karoui and Marzouk () demonstrated that aroma compounds consisted mainly of monoterpene hydrocarbons including the volatile limonene (92%), followed by α-phellandrene (2%), and α-thujene (1%). Oxygenated sesquiterpenes were found in the juice as well with caryophyllene oxide as the main component (1.4%). Regarding phenolic compounds, phenolic acids represent alone 71% with p-coumaric (18%) and ferulic acids (19%) as the most common ones, followed by flavonoids reaching 23% with rutin being the principal one [12]. According to a more recent study undertaken on some Citrus varieties, the total phenol content of C. aurantium juice was 295 ± 4 mg GAE/g (gallic acid equivalent/g of fresh juice) and the flavonoid content was 26 mg Eq Q/g (quercetin equivalent per g of fresh juice) [13]. This study demonstrated that juice extracts of C. aurantium and C. maxima varieties exhibited the highest levels of total phenols and antioxidant activities when compared to C. clementina, C. limon, and C. sinensis.

2.2. C. aurantium Flowers

C. aurantium flowers are widely used in the Mediterranean region as a food flavoring agent, and in several beverages and pastries. They are also used in medical products for their anti-depressant, anti-infectious, and sedative properties, and in skin care products [14]. Bitter orange flowers contain several products comprising essential oils, the hydrosol, and the absolute. The hydrosols are the coproducts of the hydrodistillation or the steam distillation of aromatic plants. They are valuable essential oils that are less abundantly present [15]. Absolute is a mixture obtained from the flowers of aromatic plants using ethyl alcohol as an extraction solvent (after precipitating the waxes) [16].

The total phenolic content (TPC) and the total flavonoid content (TFC) in C. aurantium bloom extract represented 4.5 mg GAE/g DW (dry weight) and 4 mg rutin equivalent/g DW respectively [17]. Using RP-HPLC, phenolic and flavonoid contents were identified as gallic acid, caffeic acid, syringic acid, rutin, pyrogallol, naringin and quercetin. A more recent paper showed that the highest TPC and TFC recorded were 81 ± 3 mg GAE/g extract and 20 ± 3 mg QE/g extract respectively in C. aurantium flowers' ethanolic extract, as compared to 1.5 mg GAE/g TPC and 0.4 mg QE/g TFC of the essential oil fraction [16]. Using GC-MS analysis, the same authors identified seventy-seven compounds in the essential oil of C. aurantium flowers, with the most frequent chemical classes being oxygenated monoterpenes, aliphatic hydrocarbons, monoterpene hydrocarbons, and esters [16]. Similarly, the most frequent detected compounds in C. aurantium petals powder were: D-glucuronic acid, D-limonene, octadecenoic acid, daphnetin, hexadecanoic acid, linalool, pyrrolidinone, and phthalic acid [18]. The latter compounds were listed in descending order: 10%, 5.5%, 4%, 3.7%, 2%, 2%, 1.2%, and 1% respectively.

2.3. C. aurantium Seeds

Citrus seeds are known to contain bioactive constituents including limonoids, carotenoids, and phenolic compounds. They were used in Persian medicine as analgesic, anti-irritant properties, and as antidotes against poisons and toxins [19]. As commonly reported in the literature, the most abundant flavonoids in C. aurantium seeds are hesperidin, neohesperidin, naringin, and narirutin. These compounds are of great importance to human health due to their anti-inflammatory, anti-cancer, anti-oxidative, and cardiovascular protective properties [20].

Flavonoids were reported to be the major components (56%) in C. aurantium seeds at the mature stage, whereas phenolic acids were found at more moderate levels (22%) [21]. Flavonoids detected were epigallocatechin, naringin, hesperidin, neohesperidin, naphtorecinol, apigenin, quercetin, resorcinol, catechin, rutin, and kaempherol. Phenolic acids included gallic acid, vanillic acid, syringic acid, rosmarinic acid, p-coumaric acid, and trans-2-hydroxycinnamic acid. A more recent study investigating the concentration of phenolic compounds present in different Citrus seeds corroborates these findings [22]. Phenolic acids found in bitter orange seeds belong to the hydroxybenzoic acids (vanillic acid, 3.3 µg/g DW) and hydroxycinnamic acids (caffeic acid, 5 µg/g DW; trans-ferulic acid, 3 µg/g DW; and p-coumaric acid, 15 µg/g DW) families [22]. TPC yield was nearly 2.5 mg GAE/g DW. In regard to limonin in C. aurantium seeds, its yield varied between 0.5 and 0.6 mg/g DW when using Na-Sal and Na-CuS as hydrotropes for extraction, respectively [23].

Based on a different perspective, Hamedi and coworkers () studied the phytosterols and fatty acid profiles of C. aurantium seed oil. They identified diverse phytosterols including free campesterol (4 mg/g), esterified and free β-sitosterol (2 mg/g and 33 mg/g respectively), and free stigmasterol (10 mg/g). Interestingly, the major fatty acids identified in the seed oil were linoleic acid (50%) and oleic acid (30%) known as omega-6 and omega-9, in addition to other fatty acids (cerotic acid, stearic acid, arachidic acid, palmitic acid, and palmitoleic acid) [19].

2.4. C. aurantium Leaves

Citrus leaves are also a significant source of bioactive constituents including flavonoids, ascorbic acid, and phenolic constituents that are recognized as natural antioxidants [24]. C. aurantium leaves can be used in pharmaceutical industries since they can be integrated in drug formulations [25].

Many studies were done on C. aurantium leaves; they are known to contain various essential oils including mainly limonene, linalool, α-terpineol, and linalyl acetate [26,27]. Phytochemical analysis of C. aurantium leaves reflected the presence of several compounds including flavanoids, phytosterols, carbohydrates, saponins, volatile oil, tannins, terpenoids, and proteins [28]. In the same study, 35 compounds were identified after reading the GC-MS profile of C. aurantium essential oil obtained through hydrodistillation. The major essential oils identified were eucalyptol (43%), sabinene (17%), β-linalool (15%), α-terpineol (8%), α-pinene (1.3%), β-myrcene (1.2%), 4-terpineol (1.1%), β-pinene (1%), D-limonene (1%), and O-cymene (1%) [28].

TPC and TFC in seven species of Citrus leaves (C. clementina, C. aurantifolia, C. limon, C. navel, C. hamlin, C. aurantium, and C. grandis) were studied. The TPC of C. aurantium leaves in aqueous extracts was 70 ± 2 mg GAE/g DW, but it was only 8 mg GAE/g DW in the methanolic extract. TFC in C. aurantium leaves was 12 ± 2 mg QE/g DW in aqueous extract compared to 5 mg QE/g DW in the methanolic extract [24], confirming that aqueous extraction was more efficient in extracting phenolics and flavonoids. In the same way, a study performed in Algeria on the peels and leaves of seven varieties of oranges showed that C. aurantium L. cv. Bigarade leaves had the highest level of TPC [29]. The authors listed the phenolic compounds of C. aurantium leaves as follows: total phenols (44 GAE/g DW), flavonoids (3 mg QE/g DW), flavonols (1.5 mg QE/g DW), proantho-cyanidins (4.5 mg CE/g DW), hydrolyzable tannins (33 ± 2 TAE/g DW), polymerized phenols (8 mg TAE/g DW), and soluble phenols (3 mg GAE/g DW). Furthermore, Haraoui and coworkers () examined the TPC in leaf extracts and juice of ten varieties of Citrus thriving in Algeria. C. aurantium leaves exhibited the highest level of total phenols (107 ± 2 mg GAE/g DW) as compared to other Citrus species, and one of the highest flavonoid's content (14 mg Eq Q/g DW) [13]. The latter two studies emphasized the richness of C. aurantium in phenolic and flavonoid compounds as compared to other Citrus species.

2.5. C. aurantium Peels

At an industrial scale, the juice yield from Citrus is approximately half the fruit weight, while the residual part mass is mostly made of peels (40'50%). Thousands of tons of Citrus peels are produced yearly as waste from processing industries. They can cause serious problems for disposal and can greatly pollute the environment since only a small amount is utilized and the remaining bulk is burned [30]. Nevertheless, these peels contain a multitude of volatile oils such as sesquiterpenes, monoterpenes and their derivatives, and many other constituents including flavones and alkaloids such as octopamine, synephrine, N-methylthyramine, and carotenoids [31,32]. They are considered as safe products commonly used in various industries: in cosmetics, perfumes, body care products, and soap industries (due to their marketable fragrance) and in foods, beverages, and ice cream industries as flavoring and acidifying agents [33,34,35,36].

C. aurantium has a thick peel that is richer in pectin than the sweet orange peel [25], and that contains higher amounts of essential oils when compared with other Citrus species [37]. The essential oil content in C. aurantium peels ranged between 0.1 and 1.7% [36] with limonene being the most abundant volatile component [38,39]. Details of compounds found in Italian C. aurantium peel were provided as follows: monoterpene hydrocarbons representing 72.5% while oxygenated monoterpenes representing 7% with the major component limonene (66%) [40]. Recently, a slightly different chemical composition of the essential oils of C. aurantium peel was reported. The major volatile components identified were monoterpene hydrocarbons (51%) and oxygenated monoterpenes (46%)'mainly: limonene (49%), linalool (32%), linalyl acetate (12%), myrcene (1.2%), geranial (1%), neral (0.5%), β-pinene (0.5%), γ-terpinene (0.4%), sabinene (0.3%), geranyl acetate (0.2%), and β-caryophyllene (0.1%) [41]. Additionally, Jabri Karoui and Marzouk () studied the bioactive contents of Tunisian C. aurantium peel. They investigated the aroma compounds using gas chromatography (GC), and gas chromatography mass spectrometry (GC-MS), and the phenolic compounds using reversed-phase high-performance liquid chromatography. The major volatile compound found in C. aurantium peel was limonene (90%) and the main phenolic compounds were phenolic acids (74%) followed by flavonoids (23%). The most common phenolic compounds found in the peel of C. aurantium were p-coumaric (25%) and ferulic acids (24%) [12]. Finally, pectin yield from C. aurantium peel was around 28% (with TPC 40 ± 3 mg GAE/g of pectin), consisting of 65% of galacturonic acid [42]. Using a different extraction method, the same team previously showed that pectin yield in C. aurantium peel was 29%, containing 71% of galacturonic acid [43].

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