9

Oils from Herbs, Spices, and Fruit Seeds

Liangli (Lucy) Yu, John W. Parry, and Kequan Zhou
University of Maryland College Park, Maryland

1. INTRODUCTION Edible seed oils are important common food ingredients. Fatty acids are primary nutritional components found in edible seed oils. Growing evidence has suggested that individual fatty acids may play different roles in human health. Diets rich in a specic fatty acid may provide potential prevention of a number of health problems or diseases. For instance, o3 (n-3) unsaturated fatty acids may have health benets including the prevention of cancer, heart disease, hypertension, and autoimmune disorders. Currently, consumers growing interest in improving their dietary nutrition is driving the development of novel seed oils having unique fatty acid proles and other benecial components, including phytosterols and natural antioxidants. It is the purpose of this chapter to summarize the edible fruit, spice, or herb seed oils with unique fatty acid proles. Physicochemical properties and other benecial components of these oils, such as phytosterols and tocopherols, may also be included. The seed oils are presented according to their primary or distinguishing fatty acid (s), including oleic, linoleic, a-linolenic, and g-linolenic acids. Seed oils containing only small amounts of benecial fatty acids but signicant quantities of other valuable components (natural antioxidants) are also included.

Baileys Industrial Oil and Fat Products, Sixth Edition, Six Volume Set. Edited by Fereidoon Shahidi. Copyright # 2005 John Wiley & Sons, Inc.

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2.

EDIBLE SEED OILS RICH IN a-LINOLENIC ACID (18:3n3)

Alpha-linolenic acid (18:3n-3) is an 18-carbon fatty acid with three double bonds at carbons 9, 12, and 15. It is an essential n-3 fatty acid that is a required nutrient for human beings and can be obtained through diets including both plant and animal sources. Alpha-linolenic acid can be converted by elongases and desaturases to other benecial n-3 fatty acids, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which are implicated in normal brain development, normal vision, and a decreased risk of heart disease. Novel dietary sources of n-3 fatty acids are desired for those who do not consume adequate amounts of sh or shbased food products rich in long-chain n-3 fatty acids. This section summarized fruit, spice, and herb seed oils rich in a-linolenic acid (18:3n-3). These include black raspberry, red raspberry, boysenberry, marionberry, blueberry, cranberry, sea buckthorn, basil, and hemp seed oils. 2.1. Black Raspberry Seed Oil (Rubus occidentalis L., cv Jewel) Black raspberry is a member of the genus Rubus from the Roseacea family, which is also known as caneberries. The majority of black raspberry crops are located in the Northwest region of the United States, predominantly in Oregon. The annual harvests for black raspberries in Oregon in 2002 and 2003 were 3.02 million pounds and 2.70 million pounds, respectively. Nearly 99.5% of the total crop goes into postharvest production (http://www.nass.usda.gov/or/berries03.pdf), and seeds are a major byproduct thereof. The fatty acid prole of two cold-pressed black raspberry seed oils demonstrated high concentrations of both n-3 and total unsaturated fatty acids. The concentration of a-linolenic acid (18:3n-3) was 35% of total fats, and unsaturated fatty acids comprised 9899% (Table 1). Linoleic acid was the predominant fatty acid (Table 1); however, the ratios of n-6 to n-3 fatty acids were very low at 1.6:1. The other measurable fatty acids included oleic (18:1n-9) and palmitic (16:0) acids (Table 1). The overall fatty acid composition of black raspberry seed oil was very similar to red raspberry seed oil (1) (Table 1). 2.2. Red Raspberry Seed Oil (Rubus ideaus) Red Raspberry is a production crop grown throughout the world, and the total worldwide annual production is typically around 250,000 metric tons (http://www.oregon-berries.com). The majority of commercial raspberries are grown in Eastern Europe, followed by Northern and Western Europe, the United States, and Chile. Like black raspberries, red raspberries are also grown in the Northwest region of the United States, and total production in the years 2002 and 2003 was 42.2 metric tons (MT) and 38 MT, respectively (http:// www.nass.usda.gov/or/berries03.pdf). Red raspberry seed oils, extracted by either hexane (2) or cold-pressing (3), were examined for their fatty acid compositions. Both methods detected very similar

TABLE 1. Fatty Acid Compositions (g Fatty Acid/100-g Oil) of Fruit Seed Oils Relatively High in a-Linolenic Acid (18:3n-3).* Fatty Acid 16:0 18:0 18:1 18:2n-6 18:3n-3 others n-6/n-3 Black Raspberry(1) 1.21.6 trace 6.27.7 55.957.9 35.235.3 nd 1.591.63 Red Raspberry(2, 1.22.7 1.0 12.012.4 53.054.5 29.132.4 nd 1.641.87
3)

Boysenberry(3) 4.2 4.5 17.9 53.8 19.5 nd 2.75

Marionberry(3) 3.3 3.1 15.1 62.8 15.7 nd 3.99

Blueberry(3) 5.7 2.8 22.8 43.5 25.1 nd 1.73

Cranberry(35) 3.07.8 0.21.9 20.027.8 35.044.31 22.335.0 2.58 1.162.0

Buckthorn(6) Buckthorn(6) sinensis rhamnoides 7.79.6 2.13.3 12.926.1 38.243.6 20.236.3 1.92.5 1.072.00 6.78.2 2.34.1 13.720.0 36.743.0 25.436.0 1.83.8 1.021.62

Buckthorn(7) mongolica 8.6 3.3 17.9 38.6 29.1 2.1 1.33

* Black raspberry, Red raspberry, Boysenberry, Marionberry, Blueberry, Cranberry, Buckthorn sinesis, Buckthorn rhamnoides, and Buckthorn mongolica, stand for black raspberry, red raspberry, boysenberry, marionberry, blueberry, cranberry, buckthorn sinesis, buckthorn rhamnoides, and buckthorn mongolica seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected.

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OILS FROM HERBS, SPICES, AND FRUIT SEEDS

fatty acid proles and high concentrations of a-linolenic acid, an n-3 fatty acid (Table 1). The crude oil from the hexane extract contained 29.1% a-linolenic acid and the extra virgin cold-pressed seed oil had 32.4% a-linolenic acid. Both of these samples were also very comparable in their fatty acid compositions compared with the black raspberry seed oil discussed above (Table 1). In addition to its a-linolenic acid content, red raspberry seed oil may contain a signicant level of tocopherols and other natural antioxidants (2, 3). Total tocopherol was 97-mg/100-g oil and 61-mg/100-g oil in the hexane-extracted and the cold-pressed oils, respectively (2, 3), whereas the antioxidant activity, measured as the oxygen radical absorbing capacity (ORAC), was 48.8-mmoles trolox equivalents per gram of oil (3). Trolox, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, is a water-soluble analog of a-tocopherol and widely used as a standard antioxidant compound.

2.3. Boysenberry Seed Oil (Rubus hybrid) Like the other caneberries (black raspberry, red raspberry, marionberry), boysenberry also prefers the growing conditions found in the Northwest region of the United States. However, aside from Oregon, boysenberry is also grown in Northern California as a production crop. In 2002 and 2003, the total boysenberry production in the United States was 2665 tons and 2350 tons, respectively. Also, like the other cold-pressed caneberry seed oils, boysenberry seed oil had a high percentage (19.5%) of n-3 a-linolenic acid and a low n-6 to n-3 ratio of 2.8:1. Total unsaturated fatty acids constituted over 91% of the seed oil and polyunsaturated fatty acids (PUFA) were very high at 73.3%, but stearic, palmitic, and total saturated fatty acids were higher than all other caneberry seed oils (Table 1). Interestingly, the boysenberry seed oil demonstrated the best antioxidative potential using the oxygen radical scavenging capacity (ORAC) test compared with eight other seed oil samples, including blueberry, black raspberry, and red raspberry seed oils, which are known to be rich in antioxidants (3).

2.4. Marionberry (Rubus hybrid) Seed Oil Marionberry is a blackberry hybrid. It is another member of the caneberry family and is also grown in the Northwest United States, specically in Oregon. The production in 2002 was 15,000 MT and in 2003 it was 12,910 MT. Marionberry comprises almost one-half of the total caneberry production in Oregon. In 2004, Parry et al. (3) examined the chemical composition and physicochemical properties of cold-pressed marionberry seed oil. The oil was shown to contain a relatively high percentage of n-3 fatty acids in the form of a-linolenic acid (15.7%) (Table 1). This amount was lower than that of other caneberry seed oils, including black raspberry, red raspberry, and boysenberry seed oils, tested under the same conditions. The n-6 to n-3 fatty acid ratio was 4:1, which was the highest among the tested caneberry group.

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237

2.5. Blueberry Seed Oil (Vaccinium corymbosum) Blueberries are grown in temperate climates throughout the world; however, the largest producers are the United States and Canada. Approximately 42,000 MT are produced annually outside of the United States and Canada. In 2002 and 2003, the United States harvested 87.3 MT and 86.200 MT, respectively. (http://usda.mannlib.cornell. edu/reports/nassr/fruit/pnf-bb/ncit0104.pdf, http://www.ushbc.org/blueberry.htm). The cold-pressed blueberry seed oil investigated by Parry and Yu. (3) demonstrated a high concentration of n-3 fatty acids. Alpha linolenic acid was the sole source of the n-3 and comprised 25.1% of the total fatty acids (Table 1). The ratio of n-6 to n-3 fatty acids was 1.7:1. Linoleic acid (18:2n-6) was the most prevalent fatty acid in the blueberry seed oil followed by a-linolenic, oleic, palmitic (16:0), and stearic (18:0) acids (Table 1). The blueberry seed oil also showed a signicantly higher antioxidant capacity compared with marionberry, black raspberry, cranberry, and pumpkin seed oils using the oxygen radical absorbance capacity (ORAC) test. Therefore, blueberry seed oil may serve as an excellent dietary source of n-3 fatty acids and natural antioxidants. 2.6. Cranberry (Vaccinum macrocarpon) Seed Oil The North American cranberry, Vaccinum macrocarpon, is best adapted to grow at higher latitudes and in bog terrains. It is grown for production in Wisconsin, Maine, New Jersey, Oregon, and Washington in the United States, and British Columbia and Quebec in Canada. Cranberries are also grown in Europe, but are a different species of Vaccinum. The total production in the United States for the year 2002 was 284,200 tons and was projected to be 291,500 tons in 2003 (http://usda.mannlib.cornell.edu/reports/nassr/fruit/zcr-bb/cran0803.pdf). Several studies have conrmed that the seed oil from the North American variety of cranberry contains signicant levels of a-linolenic acid. In a U.S. patent, Heeg et al. (4) reported the a-linolenic acid content of cranberry seed oil to be between 30% and 35% of total fatty acids. In 2003, Parker et al. (5) found 22.3% a-linolenic acid in the cold-pressed cranberry seed oil, and in 2004, Parry et al. (3) determined the oil to contain 32.0% a-linolenic acid from two different lots of the seed oil. The ratios of n-6 to n-3 fatty acids in all were low from 1.2:1 to 2:1. Also, all of the studies documented similar ratios among the rest of the common fatty acids found in cranberry seed oil, including, in order of higher amount present: linoleic, oleic, palmitic, stearic, and eicosadienoic (20:2) acids (Table 1). In addition to a-linolenic acid, cranberry seed oil is rich in natural antioxidants (8). These antioxidants may directly react with free radicals and prevent lipid oxidation in human low-density lipoprotein. 2.7. Sea Buckthorn (Hippophae rhamnoides L.) Seed Oil Sea buckthorn is native to Asia and Europe. It is a hardy plant that is also being considered as a major commercial crop in Canada. It has been used in Tibetan, Mongolian, and Chinese traditional medicine for more than 1000 years, and has demonstrated many benecial health attributes (6). The fruit has a good avor and is rich in nutrients. The whole berries contain a higher concentration of

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OILS FROM HERBS, SPICES, AND FRUIT SEEDS

Vitamin C than strawberry, kiwi, orange, and tomato, and the fruit also contains a higher concentration of Vitamin E than wheat embryo, safower, maize, and soybean (9). In 2001, Yang and Kallio (9) investigated the lipid compositions of two subspecies of Hippophae rhamnoides L. The subspecies were H. rhamnoides L. sinensis and H. rhamnoides L. rhamnoides. Twelve samples of sinensis and nine samples of rhamnoides were grown at different locations in China and Finland, respectively. Among the twenty-one samples there was some variation in the compositions of the seed oils; however, they all had relatively high percentages of a-linolenic acid, g-linolenic acid (18:3n-6), and oleic acid (18:1n-9). All seed oil samples also had an n-6 to n-3 fatty acid ratio under 2:1 (Table 1). Other constituent fatty acids included palmitic, stearic, and vaccinic (18:1n-7) acids. Kallio et al. (7) examined the fatty acid composition of the subspecies sinensis, and mongolica of Hippophae rhamnoides L. Both displayed fatty acid proles very similar to those found in the previous study. The fatty acid composition of Hippophae rhamnoides L. mongolica is shown in Table 1. 2.8. Basil (Ocimum sp.) Seed Oil Basil is a popular herb grown throughout the world and is an ingredient in many recipes. There are more than 50 species, but sweet basil, Ocimum basilicum, is the most common variety (10). In 1996, Angers et al. (10) investigated the fatty acid composition of the seed oils of four species of basil, including Ocimum basilicum, Ocimum canum, Ocimum gratissimum, and Ocimum sanctum. Also, four total different varieties of Ocimum basilicum were tested. All samples were compared with axseed oil and had similar fatty acid proles in regard to a-linolenic, palmitic, and stearic acids. The axseed oil had 52% a-linolenic acid, and the basil seed oils had 57.462.5% a-linolenic acid (Table 2). The n-6 to n-3 fatty acid ratio of the axseed oil was 1:3.2, and
TABLE 2. Fatty Acid Compositions (g Fatty Acid/100-g Oil) of Herb Seed Oils and Other Oils with Relatively High Concentrations of a-Linolenic Acid (18:3 n-3).* Fatty Acid 16:0 16:1 18:0 18:1 18:2 18:3 n-3 18:3 n-6 20:0 20:1 others n-6/n-3 O. Basilicum (basil)(10) 6.88.8 0.20.3 2.02.8 8.711.6 18.321.7 57.462.5 0.10.3 < 0.2 trace trace 0.30.4 Hemp(5,
11, 12)

5.86.7 00.2 2.63.2 9.915.6 53.460.0 15.119.4 03.6 0.81.0 nd 01.8 2.83.5

* O.basilicum (basil) and Hemp stand for O.basilicum (basil) and hemp seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected.

EDIBLE SEED OILS RICH IN g-LINOLENIC ACID

239

the basil seed oils were 1:1.61:3.6. Complete fatty acid proles are shown in Table 2. 2.9. Hemp (Cannabis sativa) Seed Oil Hemp is an ancient crop that is still cultivated by many societies and has many different uses. The ber from hemp has been used to make rope, paper, and clothing; hemp is used for medicinal purposes, and its seed oil is commercially available (11). Recent investigations of hemp seed oil (5, 11, 12) reported similar ndings in fatty acid compositions. The n-3 fatty acid, a-linolenic acid, was determined to constitute between 15.1% and 19.4% of total fat (Table 2). Gamma-linolenic acid (18:3n-6) was also detected in two of the studies, and comprised up to 3.6% of total fatty acids (11, 12) (Table 2). The most prevalent fatty acid was linoleic in all of the studies, which was between 53.4% and 60.0% of total fatty acids and was followed by a-linolenic, oleic, palmitic, g-linolenic, and stearic acids. Eicosadienoic, arachidic (20:0), and behenic (22:0) acids were also detected in small quantities.

3.

EDIBLE SEED OILS RICH IN c-LINOLENIC ACID (18:3n6)

Gamma-linolenic acid (18:3n-6) is an important unsaturated fatty acid. It is the precursor for biosynthesis of arachidonic acid that is a precursor for prostaglandin formation. Recently, g-linolenic acid has been recognized for its potential health benets in prevention and treatment of cardiovascular disorders, premenstrual syndrome, atopic eczema, rheumatic arthritis, and alcoholism (13, 14). Seed oils of blackcurrant and other Ribes species, as well as evening primrose seed oils, are rich sources of natural g-linolenic acid. 3.1. Black Currant and Other Ribes Seed Oils Blackcurrant (Ribes nigrum) is cultivated for the production of its berries (15). It is rich in ascorbic acid and exhibited high levels of antioxidant activity (16). Blackcurrant is mainly consumed in the form of juice and the seeds are the byproduct of juice production. Blackcurrant seed oils were analyzed for fatty acid composition, tocopherols, and their prostaglandin E2 production reduction potential (15, 1719). Blackcurrant seed oil is an excellent dietary source of both g-linolenic (18:3n-6) and a-linolenic (18:3n-3) acids. Gamma-linolenic acid constituted 1225% of the total fatty acids, whereas a-linolenic acid comprised the other 1013% (Table 3). The fatty acid composition was dependent on genotype and growing conditions. The seed oils also had signicant levels of tocopherols (18). The total tocopherol content was 1.22.5-mg/g oil, with a mean value of 1.7-mg/g oil for ten oil samples. The major tocopherol in the blackcurrant seed oil was g-tocopherol, but b-tocopherol was not detected in the blackcurrant seed oil. In 1999, Wu et al. (17) investigated the effect of dietary supplementation with blackcurrant seed oil on the immune response of healthy elderly subjects.

TABLE 3. Fatty Acid Composition (g Fatty Acid/100-g Oil) of Seed Oils Relatively High in g-Linolenic Acid.* Fatty Acid 16:0 18:0 18:1 18:2n-6 18:3n-6 18:3n-3 n-6/n-3
*

Blackcurrant(21) 5.3 1.5 14.7 47.0 12.2 13.2 4.5

Blackcurrant(19) 6.06.3 1.31.6 8.99.6 42.743.5 22.024.6 10.011.5 5.76.8

Evening primrose (Oenothera Spp.)(20) 710 1.53.5 611 6580 814 nd N/A

Evening primrose (Oenothera biennis)(14) 9.1 3.1 17.7 64.3 4.9 trace N/A

Evening primrose (Oenothera lamarckiana)(13) 5.87.2 1.53.1 9.220.1 62.074.6 5.59.6 nd N/A

Blackcurrant and Evening primrose stand for Blackcurrant and Evening primrose seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected, whereas N/A stands for not applicable.

EDIBLE SEED OILS RICH IN LINOLEIC ACID

241

The seed oil moderately enhanced immune function through reducing the production of prostaglandin E2, suggesting that blackcurrant seed oil may have potential in preventing cancer, cardiovascular disease, and other health problems. Other Ribes species, including R. grossularia (red-black gooseberries), R. grossularia (yellow gooseberries), R. nigrum (blackcurrants), R. rubrum (red currants), and R. nigrum R. hirtellum ( jostaberries), were also examined for g-linolenic acid concentration and tocopherol content in the seed oils. Among the tested samples, blackcurrant seed oil had greatest level of g-linolenic acid, and all three species of currant had of total concentration of tocopherols over 1.0 mg/g oil (18). 3.2. Evening Primrose Seed Oil Evening primrose (Oenothera spp.) belongs to the Onagraceae family and produces a large number of highly fertile seeds. The roots of evening primrose are used in human diet, whereas its bark, leaves, and essential oil are used for medicinal purposes (http://botanical.com/botanical/mgmh/p/primro70.html) (13, 20). Evening primrose seed oil is a natural source of g-linolenic acid (18:3n-6). Hudson (20) evaluated 192 evening primrose (Oenothera spp.) seed oil samples for their fatty acid compositions. The normal range of g-linolenic acid concentration was 8 14% and the extreme range was 220% of total fatty acids, with a median of 10.4% (Table 3) (20). Linoleic acid normally accounted for 6580% of total fatty acids and the median was 73%, which was as high as that of any known vegetable oil. Another study showed that common evening primrose (Oenothera biennis) seed oil contained 4.9% of g-linolenic acid, along with 64% linoleic acid (14). In addition, the growing conditions were found to alter the g-linolenic acid content in the seed oil. The concentration of g-linolenic acid ranged from 5.59.6% of total fatty acids (Table 3) (13). Ratnayake et al. (14) reported that evening primrose seed oil from Canada contained 64.3% of linoleic acid and 4.9% of g-linolenic acid (Table 3). These previous studies indicate that evening primrose (Oenothera spp.) seed oil contains a signicant level of natural g-linolenic and oleic acids, and linoleic acid is the predominant fatty acid. This topic is discussed in another chapter in this series. 4. EDIBLE SEED OILS RICH IN LINOLEIC ACID (18:2n6) Linoleic acid (18:2n-6) is an essential fatty acid that must be obtained through diets. In this section, fruit, spice, and herb seed oils rich in linoleic acids are summarized. These seed oils include watermelon, melon (Cucumis melo and Colocynthis citrullus), goldenberry, grape, rose fruit, paprika, red pepper, onion, black cumin, and Onagraceae seed oils. Several seed oils may be listed in other sections if they contain signicant level of a special fatty acid. For example, pumpkin seed oils rich in both oleic acid and linoleic acid, are listed under the section named, Edible seed oils rich in oleic acid (18:1n-9).

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OILS FROM HERBS, SPICES, AND FRUIT SEEDS

4.1. Watermelon (Citrullus vulgaris) Seed Oil Watermelon (Citrullus vulgaris) is taxonomically classied as a member of the Curcubitaceae family, which is also known as the gourd family. Other gourds include pumpkins, cucumbers, squash, and other melons. It prefers warm climate growing conditions and is produced worldwide where conditions permit. Over 1200 varieties have been cultivated and about 250 varieties are grown in North America, http:// www.watermelon.org/index.asp?adsp&htypeabout&pid39. The worlds production of watermelons in 2002 was over 81 million metric tons (MMT) and approximately 71% of that was grown in China. The U.S. production in both 2002 and 2003 was over 1.7 MMT (http://usda.mannlib.cornell.edu/reports/nassr/ fruit/pvg-bban/vgan0104.txt). Watermelon seeds are consumed as snack food worldwide and are used to prepare edible oil in some countries. Watermelon seed oil was prepared and evaluated for its physicochemical properties (22, 23). The seed oil consisted of 59.6% linoleic acid (18:2n-6) and 78.4% total unsaturated fatty acids (Table 4). The predominant fatty acid in the oil was linoleic acid, which was followed by oleic, palmitic, and stearic acids. Linolenic, palmitoleic, and myristic acids were minor constituents. The refractive index, acid value, peroxide value, and free fatty acids of watermelon seed oil were determined to be 1.4696 (25 C), 2.82 (mg KOH/g oil), 3.40 (mequiv oxygen/kg oil), and 1.41 (% as oleic acid), respectively. The saponication value of watermelon seed oil was 201 (mg KOH/g oil), and its iodine value was 115 (g iodine/100-g oil), which was signicantly higher than pumpkin at 109 (g iodine/100-g oil) (22, 23). 4.2. Melon (Cucumis melo) Seed Oil Melon, Cucumis melo, is a member of the Cucurbitaceae family and grows best in tropical regions. The pulp of the fruit has pleasant avor and taste, and the seeds are generally treated as waste; however, medicinal effects have been reported for the seeds (24, 25). Hexane-extracted seed oil of Cucumis melo hybrid AF-522 was determined to contain 64 g of linoleic acid per 100 g of total fatty acids (Table 4) (24). Signicant amounts of oleic, palmitic, and stearic acids were also detected in the melon seed oil. The specic gravity (28 C), refractive index (28 C), and iodine value of the seed oil were 0.9000, 1.4820, and 112, respectively, under the experimental conditions (24). Earlier in 1986, Lazos (25) extracted the oil from Cucumis melo seeds and examined its physicochemical properties (25). Linoleic acid was the primary fatty acid and accounted for 64.6% of the total fat (w/w), along with 20.1% oleic acid, and 14.7% total saturated fatty acids (Table 4). Iodine value and refractive index (40 ) of the seed oil were 124.5 and 1.4662, respectively. 4.3. Melon (Colocynthis citrullus L.) Seed Oil Colocynthis citrullus L (melon) is a tropical vine that is native to West Africa. The esh from the fruit of this melon is bitter and inedible; the edible part of the fruit is the seed (33). Nwokolo and Sim (26) examined the fatty acid composition of

TABLE 4. Fatty Acid Composition (g Fatty Acid/100-g Oil) of Fruit Seed Oils Relatively High in Linoleic Acid.* Fatty Acid Watermelon(22, 11.3 10.2 18.1 59.6 0.4 21.5 78.4
23)

Melon (cucumis melo)(24, 9.09.5 4.95.6 19.420.1 64.164.6 0.20.3 14.715.2 84.485.1

25)

Melon (Colocynthis citrullus L.)(26, 11.812.1 9.010.7 13.514.5 57.765.4 2.1 21.125.3 74.677.5

27)

Goldenberry(28) 7.3 2.5 11.7 76.4 0.3 11.9 88.1

Grape(29,

30)

Rose(31) 1.73.1 1.72.5 14.718.4 48.654.4 16.418.4 11.618.1 81.888.3

Paprika(22,

23, 32)

16:0 18:0 18:1 18:2n-6 18:3n-3 Total saturated Total unsaturated

5.814.2 8.6 13.731.9 50.177.8 5.0 8.414.4 85.591.5

11.213.8 3.23.7 9.814.6 67.874.4 nd 15.017.6 82.584.9

* Watermelon, Melon (Cucumis melo), Melon (Colocynthis citrullus L.), Goldenberry, Grape, Rose, and Paprika stand for Watermelon, Melon (Cucumis melo), Melon (Colocynthis citrullus L.), goldenberry, grape, rose, and paprika seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected.

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OILS FROM HERBS, SPICES, AND FRUIT SEEDS

Colocynthis citrullus seed oil and found that it contained a relatively high percentage of linoleic acid that accounted for 57.7% of total fatty acids (Table 4) (26). Oleic acid was the second major fatty acid (14.5%). The seed oil contained about 25.3% saturated fatty acids (Table 4). Moussata and Akoh (27) also reported a similar fatty acid prole of Colocynthis citrullus L. seed oil. The primary fatty acid was linoleic acid, contributing 65.4% of total fats. The other signicant fatty acids included oleic (13.5%), palmitic (12.1%), and stearic (9.0%) acids (Table 4). 4.4. Goldenberry (Physalis peruviana L.) Seed Oil Goldenberry, (Physalis peruviana L.), also known as cape gooseberry, is a perennial native to the Andes. It is also cultivated in the United States, South Africa, East Africa, India, New Zealand, Australia, and Great Britain (34). It is related to both tomatoes and chile peppers and prefers growing in well draining soils like tomatoes. Goldenberry has a pleasant avor that is similar to tomatoes and is eaten in many ways, including in salads, cooked dishes, chocolate covered desserts, jams, preserves, and natural snacks (28). The fruit is an excellent source of Vitamins A and C as well as minerals. Goldenberry seed oil was prepared by extracting lyophilized ground seed meal with chloroform-methanol and was characterized for fatty acid composition (28). The fatty acid composition of the seed oil is shown in Table 4. Linoleic acid was the predominant fatty acid and constituted 76.1% of total fat. Combined monounsaturated fatty acids were 12.2%, linolenic acid was 0.33%, and total polyunsaturated fatty acids were 76.1%. These data suggest that goldenberry seed oil may serve as an excellent dietary source for linoleic acid, the essential n-6 fatty acid, and may be a good choice for consumers seeking a greater intake of total unsaturated fatty acids. The fat-soluble Vitamins E and K, carotene, and phytosterols were also detected in the goldenberry seed oil (28). Total tocopherols were 29.7 mg/g oil, including 0.9-mg a-, 11.3-mg b-, 9.1-mg g-, and 8.4-mg d-tocopherols. The total Vitamin K content was 0.12-mg/g oil, and the b-carotene concentration was 1.30-mg/g oil. In addition, signicant levels of phytosterols were also detected. The major phytosterol in the goldenberry seed oil was campesterol, having a concentration of 6.5-mg/g oil. Other phytosterols, including ergosterol, stigmasterol, lanosterol, b-sitosterol, 5-avenosterol, and 7-avenosterol, were also detected in the seed oil. 4.5. Grape Seed Oil (Vitis spp.) World grape production was 61.2 million tons in 2001 (http://www.winetitles. com.au/awol.overview/world.asp). Grape seeds are byproducts from the manufacturing of grape juice, jam, jelly, and wine. In 1998, Abou Rayan et al. (29) investigated the characteristics and composition of Egyptian-grown Cabarina red grape seed oil. Crude grape seed oil was extracted with hexane at room temperature. Linoleic acid was the major fatty acid detected and comprised more than 50% of

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245

the total fatty acids (Table 4) (29). Oleic acid was the second major fatty acid in the seed oil, along with signicant levels of palmitic and stearic acids. This nding is consistent with a previous observation in which linoleic acid accounted for 62% of the total fatty acids in grape seed oil (Table 4) (30). Iodine value (IV) and peroxide value (PV) were also determined according to the methods described in AOCS, 1983. The measured IV was 130-g iodine/100-g oil, and the PV was determined to be 2.92-mequiv peroxide/kg oil.

4.6. Rose Fruit (Rosa canina L.) Seed Oil Rose, Rosa canina L., also known as dogberry or hop fruit, is in the Rosaceae family. The fruit of this particular species of rose is generally used to prepare a stew. The seeds from Rosa canina L. were investigated for their chemical composition and nutritional values for medicinal purposes. Seed oils were prepared from fruits grown at three locations in Turkey and evaluated for their fatty acid composition (31). Linoleic acid was the primary fatty acid detected, which ranged from 48.654.4% of total fatty acids, followed by a-linolenic acid (16.418.4%) and oleic acid (14.718.4%) (Table 4). The seed oil contained approximately 85% total unsaturated fatty acids, indicating that Rosa canina L. seed oil may be an excellent source for unsaturated and essential fatty acids.

4.7. Paprika (Capsicum annuum) Seed Oil Paprika (Capsicum annuum) is a commonly used avor enhancer, and following production, the seeds are treated as waste. Paprika seed oils have been evaluated for their physicochemical properties (22, 23, 32). Paprika seed oil contained more than 82% of total unsaturated fatty acids, with polyunsaturated fatty acids comprising 67.8% of total fatty acids (Table 4) (22, 23). Oleic acid was the second major fatty acid at approximately 15% of the total. This fatty acid prole was consistent with a previous observation by Domokos et al. (32) on the fatty acid prole of Hungarian paprika seed oils. Linoleic acid comprised 74.4% of the total fat, whereas oleic and palmitic acid made up 9.8% and 11.2% of total fat, respectively (32). The paprika seed oil was determined to contain 870 mg/kg oil total tocopherols, 380 mg/kg oil carotenoids, and 0.92% phytosterols (32).

4.8. Apple Seed Oil In 1997, the production of apples was 44.7 MMT worldwide, and 84% of that was processed (http://www.geocities.com/perfectapple/prod.html). In 20002001, the worldwide apple production reached a record high of 48 MMT (http://www.fas.usda. gov/htp/circular/2003/3-7-03%2520Web%2520Art.%Updates//World%2520Apple% 2520Situation%25202002-03.pdf). Apple seeds are a byproduct of processing. In 1971, Morice et al. (35) investigated the seed oils from three different varieties

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TABLE 5. Fatty Acid Composition (g/100-g Fatty Acids) of Apple Seed Oils.*(35) Fatty Acid 16:0 16:1 18:0 18:1 18:2 18:3 20:0 20:1 20:2 22:0
*

Granny Smith 6.87.1 0.10.2 1.02.1 24.427.4 62.164.1 0.20.4 0.61.1 0.20.3 0.10.7 0.10.2

Sturmer 4.86.4 0.1 1.52.5 32.836.6 52.158.3 0.5 0.71.7 0.20.4 0.10.7 0.10.3

Dougherty 5.76.8 0.10.2 1.32.1 34.642.1 48.256.1 0.6 0.60.9 0.20.3 0.00.3 0.1

Golden Delicious 8.5 0.5 nd 31 59 0.5 0.5 nd nd trace

Granny Smith, Sturmer, Dougherty, and Golden Delicious stand for seed oil of four varieties of apple. Numbers correspond to the references cited. nd stands for not detected.

of apples: Granny Smith, Sturmer, and Dougherty, and compared them with the seed oils prepared from other apple varieties. The results showed similarities in the fatty acid proles among the varieties (Table 5). Oleic and linoleic acids consisted of 8595% of the total fatty acids in all tested samples (35). The investigators also examined other physicochemical properties of apple seed oils. The Granny Smith apple seed oil had an iodine value of 127-g iodine/100-g oil; the Sturmer had an IV of 122.4-g iodine/100-g oil, and the Doughertys IV was 119-g iodine/ 100-g oil. Apple seed oils may be useful as a dietary source for linoleic and oleic acids. 4.9. Red Pepper Seed Oil Chili peppers, Capsicum sp. are members of the Solanaceae family. They originated in South America but are now grown worldwide. They are eaten in many dishes throughout the world and provide the feeling of hotness when eaten. There is a very large range of hotness among the Capsicum species, which depends on their concentration of capsaicin. Some selected peppers ranging from lowest in concentration of capsaicin include bell, Anaheim, jalapeno, Hungarian wax, serrano, cayenne, and habanero. Red pepper seeds are byproducts from the production of red pepper powder. For centuries in South America, peppers have been used to treat such ailments as gastrointestinal disorders, and it is also thought to benet those suffering from circulatory diseases. Capsaicin, the spicy chemical in peppers, has also been shown to be a potent anti-inammatory in vivo (36). The roasted red pepper seed oil contained an extremely high concentration of linoleic acid, approximately 74%, and a high total unsaturated fat level (Table 6) (37). The fatty acid prole was very similar to that of both goldenberry seed (Physalis peruviana L.) and safower oils (36). The iodine value of roasted red pepper seed oil was determined to be 137-g iodine/100-g oil.This shows that there is a high degree of unsaturation in the oil. Oxidative stabilities of the roasted red

EDIBLE SEED OILS RICH IN LINOLEIC ACID

247

TABLE 6. Fatty Acid Composition (g Fatty Acid/100-g Oil) of Herb Seed Oils Relatively High in Linoleic Acid.* Fatty Acid 16:0 18:0 18:1 18:2n-6 18:3n-3
*

Red Pepper(37) 13.4 2.1 10.2 73.9 0.4

Onion(38) 9.1 4.4 34.3 44.6 0.3

Onion(3) 5.66.2 0.63.5 26.730.1 63.7 nd

Black Cumin(39) 13.013.1 3.2 24.0 57.057.3 nd

Onagraceae(40) 8.010.9 2.43.5 8.713.1 71.580.0 nd

Red pepper, Onion, Black cumin, and Onagraceae stand for red pepper, onion, black cumin, and Onagraceae seed oil. Numbers correspond to the references cited. nd stands for not detected.

pepper seed oil were tested at different roasting times. As roasting time increased, the oxidative stability of the oil increased signicantly. 4.10. Onion Seed Oil Onion (Allium cepa) seeds contained about 23.6% crude fat. The seed oil was analyzed for its chemical composition. The onion seed oil contained 44.6% linoleic acid and 34.3% oleic acid (Table 6) (38). The total unsaturated fatty acids comprised of 79% of the oil. A greater concentration of linoleic acid was determined in the cold-pressed onion seed oil obtained from Botanical Oil Co. (Spooner, WI). Linoleic acid accounted for 63.7% of total fatty acids, and oleic acid ranged from 26.730.1%. The total unsaturated fatty acids were about 90% (3). In summary, onion seed oil may serve as a dietary source of essential n-6 fatty acid and oleic acid. 4.11. Black Cumin (Nigella sativa L.) Seed Oil Black cumin (Nigella sativa) is an annual spicy herb. It has been used for many years as a food preservative and a traditional medicine for protection against and a therapeutic remedy against a number of health disorders (41). Black cumin seed and its oil have also been used for medicinal purposes (39). According to rsel (39), the seed contained about 2835% oil. Black cumin Ramadan and Mo seed oil contained a relatively high level of unsaturated fatty acids ($ 84%) of the total fatty acids (Table 6). The major fatty acid in the seed oil was linoleic acid, which accounted for about 57% of the total fatty acids, followed by oleic acid from 23.924.1%, along with a small amount of palmitic and stearic acids. However, the iodine value of the seed oil was only 48.4-g iodine/100-g oil, which is much lower than the expected value relating to the level of unsaturation. 4.12. Seed Oils of Some Onagraceae Rich in Linoleic Acid Onagraceae contains about 36 genera and 300 species; it can grow in mud, sand, rocks, or on grassy plains and occurs chiey in the temperate zone of the New

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World, primarily on the Pacic coast. Family members include evening primrose, fushia, suncups, willowherb, and clarkia (http://1.1911encyclopedia.org/O/ON/ ONAGRACEAE.htm). The seeds of selected Onagraceae, including Oenothera picensis, O. indecora, Ludwigia longifolia, and O. L. peruviana were analyzed for their physicochemical characteristics (40). Linoleic acid was the predominant fatty acid in all tested seed oils, comprising 71.580.0% of the total fatty acids (Table 6) (40). These Onagraceae seed oils may be excellent dietary sources of the essential n-6 fatty acid (18:2n-6).

5. EDIBLE SEED OILS RICH IN OLEIC ACID (18:1n-9) Oleic acid is an n-9 monounsaturated fatty acid (MUFA). Growing evidence suggests that diets rich in oleic acid may serve as an alternative choice to a low-fat blood cholesterol reducing diet, modulate immune function, and may delay the development of atherosclerosis (4244). Oleic acid is the predominant fatty acid in olive, canola, peanut, and specially produced sunower seed oils. Oleic acid is not an essential fatty acid; it is synthesized in vivo through the desaturation of stearic acid (18:0). Oleic acid is also rich in a number of other edible oils, including mango, cherry, date, pumpkin, naked seed squash, uted pumpkin, carob bean germ, American gingseng, Khaya senegalensis, and Moringa oleifera seed oils. 5.1. Mango Seed Kernel Oil Mango seed kernels contain about 412% total fat (4547). Mango seed kernel oil is rich in oleic acid (Table 7), and exhibited 42% (47), 3459% (45), and 4144% of total fatty acids (46). Stearic acid is the other major fatty acid in mango seed kernel
TABLE 7. Fatty Acid Composition (g/100-g Fatty Acids) of Fruit Seed Oils Rich in Oleic Acid.* Fatty Acid 12:0 14:0 16:0 16:1 18:0 18:1 18:2n-6 18:3n-3 20:0 Other FA
*

Mango(4547) nd nd 618 nd 2657 3459 113 nd <4 nd

Cherry(48) nd nd 6.89.4 0.40.6 1.62.1 23.937.5 40.048.9 <1 < 1.3 10.313.3

Date(49) 16.917.8 10.812.1 10.210.4 0.2 2.82.8 43.545.0 8.78.2 0.6 0.50.6 3.64.1

Fluted Pumpkin(26) nd 0.6 17.1 nd 15.0 35.4 27.1 1.2 1.7 nd

Carob Bean Germ(50) nd < 0.1 7.814.2 nd 3.010.0 20.438.5 43.659.2 0.31.3 nd nd

Mango, Cherry, Date, and Fluted pumpkin stand for mango, cherry, date, and uted pumpkin seed oil, respectively. Carob bean germ stands for carob bean germ oil. Numbers correspond to the references cited. nd stands for not detected.

EDIBLE SEED OILS RICH IN OLEIC ACID

249

oil and may account for up to 57% of the total fat. In addition, palmitic and linoleic acids were detected in the oil along with trace amounts of a-linolenic acid (45, 47). 5.2. Cherry Seed Oil The cherry tree (Prunus avium L.) is a member of the Rosaceae family. Cherry seed contains about 18% oil on a dry weight basis (48). Signicant levels of oleic acid were detected in the cherry seed oils prepared by hexane extraction using a Soxhlet apparatus. Oleic acid comprised 2438% of the total fatty acids from three different varieties of cherry fruits (Table 7) (48). Linoleic acid was the major fatty acid in the cherry seed oil, and ranged 4049% in the seed oil, along with a-eleostearic (18:n-5), palmitic, stearic, arachidonic, and a-linolenic acids (Table 7). alphaeleostearic acid (9c,11t,13t), comprising 1013% of cherry seed oil, is a conjugated isomer of a-linolenic acid (9c,12c,15c). alpha-eleostearic acid was not detected in other previously studied seed oils from prunoids including peach, apricot, and plum seed oils. 5.3. Date Seed Oil Dates (Phoenix dactylifera L.) are popular in most Middle Eastern countries and serve as a major source of food and nutrients (51, 52). Oil contents and fatty acid proles of date seeds may vary among individual varieties. Date seeds contained 2024% total fat (49). Oleic acid was the primary fatty acid in the date seed oil and had a concentration of 43.545% of total fatty acids. This was followed by lauric (12:0), myristic (14:0), palmitic (16:0), linoleic (18:2n6), capric (10:0), and stearic (18:0) acids along with trace amounts of other fatty acids (Table 7). Date seed oil may serve as an excellent dietary source of oleic acid with a minor amount of linoleic acid. 5.4. Fluted Pumpkin (Telfaria occidentalis) Seed Oil The uted pumpkin (Telfaria occidentalis) is a tropical gourd native to West Africa. It is taxonomically classied as a member of the Curcubitaceae family. The fruits are very large and weigh up to 13 kg, but only the seeds are edible (33). The seeds are very rich in both protein and fat, containing approximately 28% and 55%, respectively, from whole oven-dried uted pumpkin seeds (26). The fatty acid prole of uted pumpkin seeds demonstrated a high oleic acid content of 35.4% and a total saturated fatty acid concentration over 34% (Table 7) (26). Signicant level of linoleic acid (18:2n-6) was also detected in the seed oil. 5.5. Carob Bean Germ Seed Oil Carob (Ceratonia siliqua L), a tree in the Leguminosae family, is widely cultivated in the south and east of the Mediterranean region. The pulp tastes sweet and is used as a food source (50). The seed germ contains about 5% oil. Oleic acid

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contributed to 2039% of the total fatty acids, but only a small portion of that was on the sn-2 position of the triacylglycerol. Linoleic acid ranged 4459%, whereas palmitic and stearic acids accounted for 814% and 310% of the total fatty acids, respectively, along with minor amount of linolenic and myristic acids (Table 7). In addition, b-sitosterol was the primary sterol compound and contributed to 74% of the total sterols. Other sterol compounds included stigmasterol (17% of total sterol), campesterol (6%), and cholesterol (4.4%). 5.6. Pumpkin (Curcubita sp.) Seed Oil Pumpkin, Curcubita sp., is a member of the gourd family, Curcubitaceae, that also includes melons, cucumbers, squash, and gac. In 2003, the United States production of pumpkins was approximately 335,000 MT (http://usda.mannlib.cornell.edu/ reports/nassr/fruit/pvg-bban/vgan0104.txt). In some mid-eastern African countries, dried pumpkin seeds have been used to treat tapeworm when eaten on an empty stomach (53). Also, for many years in Europe, pumpkin seeds have been used as a remedy for micturition. Pumpkin seed oil has also shown possible benecial affects in retarding the progression of hypertension (54), potential anti-inammatory activity in arthritis (55), and may be effective in reducing the risk of bladder-stone disease (56). The fatty acid compositions of the seed oils prepared from a combination of two different pumpkin species (pepo and mixta) are shown in Table 8 (25). The seed oil contained 37.8% oleic acid and 43.1% linoleic acid and was fairly high in unsaturated fats (81%). Among the four pumpkin seed oil samples analyzed by Spangenberg and Orgrinc (57), oleic acid content was consistent and ranged 30.233.9% of total fatty acids (57), along with 24.547.9% linoleic acid (Table 8). In addition, the oil of unroasted pumpkin seed kernel (Cucurbita mixta) contained 21.4% oleic acid and 58.9% linoleic acid (58). A recent study of pumpkin seed oil detected 55.6% linoelic acid and 20.4% oleic acid in the total fatty acids, with a total unsaturated fatty acid concentration of 76.5% (22, 23). The iodine value for the pumpkin seed oil was 103-g iodine/100-g oil (25), and the refractive index was 1.4616 (40 C) (25), 1.4706 (25 C) (22, 23), and 1.4615 (60 C) (58). The ORAC value of roasted pumpkin seed oil was determined to be 1.1-m moles TE/g oil, and was the lowest in comparison with six other fruit seed oils tested that included blueberry, red raspberry, black raspberry, boysenberry, and cranberry seed oils (3). Phytosterols were also detected in pumpkin seed oil (22, 23). The seed oils from African pumpkin (squash) (Cucurbita pepo L.) were evaluated for their fatty acid proles and the presence of other phytochemicals (53). The seed oils contained 2836% oleic acid. The primary fatty acid was linoleic acid, along with palmitic and stearic acids, with a total unsaturated fatty acid concentration of 7783%. Alpha-tocopherol was determined at a concentration up to 3.0 mg/ 100 g. These data suggest that pumpkin seed oil may be a better choice for consumers who prefer high unsaturation, or both linoleic and oleic acids. Seed oils from species of Cucurbita with minimal pericarp, called naked seed squash, are discussed below.

TABLE 8. Fatty Acid Composition (g Fatty Acid/100-g Oil) of Cucurbita Seed Oils Relatively High Oleic Acid.* Fatty Acid 16:0 18:0 18:1 18:2n-6 18:3n-3
*

Pumpkin(25) 12.7 5.4 37.8 43.1 0.3

Pumpkin (C. Pepo)(57) 13.649.2 4.811.2 30.233.9 24.547.9 0.40.9

Pumpkin(58) 13.8 5.9 21.4 58.9 nd

Pumpkin (Cucurbita sp)(22, 13.4 10.0 20.4 55.6 nd

23)

African Pumpkin(53) 11.114.0 4.88.2 28.335.5 43.051.9 0.3

Pumpkin(3) 6.6 3.5 42.0 47.8 nd

Squash(60) 6.624.4 1.210.2 1031.6 39.377.2 nd

Squash(59) 12.815.8 5.28.3 46.660.4 9.627.9 0.10.8

Pumpkin and Squash stand for pumpkin and squash seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected.

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5.7. Naked Seed Squash (Curcubita pepo L.) Seed Oil Squash (Curcubita foetidissima, C. pepo, and C. lagenaria) has been consumed worldwide for thousands of years. The fruits are used as vegetables and desserts, and seeds are consumed as nuts or used to prepare edible oils (61). Normally, each plant produces 19 fruits weighing 0.4712.67 kg, and each fruit may have 16393 seeds (59). The weight of the individual naked seeds ranged from 46 223 mg. Seeds of the naked seed squash varieties are preferred for direct consumption and further processing. In 1996, Idouraine et al. (59) reported that the crude oil content in the nine selected naked seed squash lines (C. pepo L.) ranged 3444% on a dry weight basis. The seed oil of the selected naked seed squash was rich in oleic acid, which made up 4760% of the total fatty acids. Other major fatty acids were linoleic, palmitic, and stearic acids, along with a small amount of other long-chain fatty acids. The total unsaturated fatty acids ranged from 7079% for the nine tested seed oils (59). These were in consistent with earlier observations that oleic acid was the major fatty acid and constituted 4650% of the seed oils for all progeny lines (62, 63). In summary, the seed oil of Curcubita pepo may serve as edible oil rich in unsaturated fatty acid and oleic acid. In addition, other studies reported that linoleic acid was the predominant fatty acid in the seed oils of squash varieties (Curcubita foetidissima) with a range of 3977%, whereas the level of oleic acid was 1032% (25, 60, 64). Interestingly, a signicant level of conjugated dienoic acids was detected in the seed oils of Curcubita foetidissima. It is widely accepted that conjugated linoleic acids may have a number of health benets, such as anticarcinogenesis, reducing body weight, antiatherosclerotic activity, and antioxidant activity (65). Future research is required to further conrm the presence of the conjugated dienoic acids in the seed oils of Curcubita foetidissima and identify their chemical structures. In summary, seed oil of Curcubita foetidissima may serve as edible oil rich in unsaturated fatty acid and linoleic acid.

5.8. American Ginseng Seed Oil American ginseng (Panax quinquefolium L.), native to North America, is one of the most widely used medicinal herbs. American ginseng seed oil prepared by hexane or methylene chloride extraction at ambient temperature was analyzed for fatty acid prole and phytosterol content (66). The seed oils contained about 86.887.5% oleic acid, 10.010.5% linoleic acid, and 2.6% total saturated fatty acids (Table 9). Signicant levels of phytosterols were observed in the American ginseng seed oils prepared with hexane and CH2Cl2 (66). Squalene was the major phytosterol compound with a concentration of 502514-mg/100-g oil, followed by b-sitosterol and stigmasterol at levels of 164177-mg/100-g oil and 9395-mg/100-g oil, respectively. Phytosterols are thought to benet human health through lowering cholesterol and increasing antioxidant activity (71, 72). American ginseng seed oil would therefore be a desirable dietary source for oleic acid, squalene, and total phytosterols.

EDIBLE SEED OILS RICH IN OLEIC ACID

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TABLE 9. Fatty Acid Composition (g/100-g Fatty Acids) of Seed Oils Rich in Oleic Acid.* Fatty Acid 14:0 16:0 16:1 18:0 18:1n-9 18:2n-6 18:3n-3 20:0
*

American Ginsengo(66) K. Senegalensis(67) M. Oleifera(68, 69) M. Oleifera Mbololo(70) nd 2.22.3 nd 0.30.4 86.887.5 9.9510.5 nd nd nd 21.4 nd 10.4 64.6 nd nd nd < 0.1 5.96.5 1.01.8 5.77.2 66.976.0 0.61.3 < 0.2 3.04.0 0.1 5.76.0 0.1 1.421.57 73.675.4 0.7 0.2 2.52.7

American ginsengo, K. senegalensis, M. Oleifera, and M. oleifera Mbololo stand for American ginsengo, K. senegalensis, M. oleifera Mbololo, and M. Oleifera seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected.

5.9. Khaya senegalensis Seed Oil Khaya senegalensis is a dry land mahogany that grows to about 30 m in height and 3 m in girth; it is widely distributed in the savanna region of Nigeria. The seed of Khaya senegalensis contains about 53% oil. The seed oil has been used to treat certain local ailments. Oleic acid was the predominant fatty acid in the seed oil and accounted for 65% of the total fatty acid, along with 21% palmitic and 10% stearic acids (Table 9) (67). The seed oil had a saponication value of 186-mg KOH/100-g oil, a density of 0.962, a refractive index of 1.4690 (20 C), and an iodine value of 68.0-g iodine/100-g oil (67). 5.10. Moringa oleifera Seed Oil Moringa oleifera, native to the western and sub-Himalayam tracts of India and other countries in Asia, Africa, the Middle East, Central America, and the Caribbean islands, is the most common and broadly distributed species of the Moringaceae family (73). The leaves, owers, fruits, and roots of the tree are used as vegetables (70). Each fruit generally contains about 20 seeds, which have an average weight of 0.3 g, with the kernel responsible for 7075% of the weight. The seed oils of Moringa oleifera were extracted and analyzed for chemical compositions (68, 69). The seed oil was a rich source of monounsaturated fatty acid, especially 18:1 that contributed to 74.476.0% of the total fatty acids (Table 9) (68, 69). A signicant amount of phytosterols was detected in the seed oil (68). The major sterols were b-sitosterol (46.65% of total sterol), stigmasterol (19%), campesterol (16%), and 5-avenasterol (10.7%), along with a number of others. The seeds of M. oleifera variety Mbololo yielded 26%, 31%, and 36% crude oil by cold-pressing, hexane extraction, and chloroform-methanol extraction (1:1, v/v), respectively (70). The seed oil was rich in total monounsaturated fatty acids and contained 7475% oleic acid (Table 9). The total saturated fatty acids were

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OILS FROM HERBS, SPICES, AND FRUIT SEEDS

1921% in the seed oil, with small amounts of linoleic and a-linolenic acids. The density of the seed oils prepared by solvent extraction and cold-pressing ranged from 0.88090.9182 g/mL at 24 C, which is similar to that of olive oil at 0.915 g/ mL at the same temperature. The refractive index (ND40 C) was 1.45491.4591 and the smoke point was 198202 C for the seed oils. The seed oil prepared by cold-pressing had a greater viscosity of 103 mPa s, whereas the oil prepared by solvent extraction exhibited a viscosity of 5766 mPa s, which is more comparable with that of olive oil (74 mPa s) (70). In addition, the seed oil of M. oleifera variety Mbololo contained greater concentrations of total sterols and tocopherols than olive oil. The primary sterol in the Mbololo seed oil was b-sitosterol with signicant levels of stigmasterol, campesterol, and 5-avenasterol, as well as small amounts of other sterol compounds (70). Thus, seed oil of M. oleifera may serve as a dietary source of oleic acid, sterols, and tocopherols.

6. OTHER SPECIAL SEED OILS OF FRUIT, SPICE, AND HERB 6.1. Gac (Momordica cochinchinensis) Gac (Momordica cochinchinensis Spreng) is another member of the gourd family (Curcubitaceae). The gac fruit is round and about 1822 cm in diameter. It is native to Asia and is both consumed as food and used in traditional medicine. The seeds comprise about 16% of the total fresh weight of the fruit. Ishida et al. (74) examined gac seed oil for its fatty acid composition. The oil was determined to contain an average of 60.5% stearic acid. Palmitic and arachidic acids were two other saturated fats found in the gac seed oil, and the total percent of saturated fatty acids ranged from 60.5% to 79.2%. The most prevalent unsaturated fatty acid was linoleic acid at 20.3%, with an interesting variety of others including palmitoleic (16:1), oleic (18:1n-9), cis-vaccenic (18:1n-11), a-linolenic acid (18:3n-3), eicosa-11-enoic acid (20:1n-11), and eicosa-13-enoic acid (20:1n-13) (Table 10).

TABLE 10. Fatty Acid Composition (g /100-g Fatty Acids) of Gac and Pomegranate Seed Oils.* Fatty Acid 16:0 18:0 18:1 18:2n-6 18:3n-3 18:3n-5 others Pomegranate(75) 4.8 2.3 6.3 6.6 nd 65.3 nd Gac(74) 5.26.2 54.571.7 4.811.2 11.225.0 0.40.6 nd 3.04.1

* Pomegranate and Gac stand for pomegranate and gac seed oil, respectively. Numbers correspond to the references cited. nd stands for not detected.

SUMMARY

255

6.2. Pomegranate Seed Oil Pomegranate (Punica granatum), of the Punicaceae family, is a small tree grown in Iran, India, and the United States, as well as in most Near and Far East countries (75). Pomegranate is used as a table fruit and is also processed into juice. Pomegranate preparations, including the juice of the fruit, the dried pericarp, the bark, and the roots, have been used in folk medicines to treat colic, colitis, dysentery, diarrhea, menorrhagia, oxyuriasis, parasis, headache, vermifugal, carminative, antispasmodic, taenicidal, and emmenagogue (75). Seeds are byproducts form the juice manufacture. Cold-pressed pomegranate seed oil was prepared and analyzed for fatty acid composition, inhibitory effects against both cyclo-oxygenase and lipoxygenase, antioxidant properties, and total phenolic content (75). The major fatty acid was punicic acid (18:3n-5), which comprised 65% of total fatty acids, along with linoleic, oleic, palmitic, and stearic acids (Table 10). The seed oil contained about 150 ppm total phenolics on an oil weight basis. The oil extract, at a concentration of 5 mg/mL total phenolics, exhibited 37% inhibition of the sheep cyclo-oxygenase activity under experimental conditions (75). On a same weight concentration basis, the oil extract resulted in 75% inhibition of the soybean lipoxygenase activity, whereas butylated hydroxy anisole (BHA) had a 92% inhibition under the same experimental conditions. The oil extract also showed strong antioxidant activity in the coupled oxidation system of carotene and linoleic acid, and the antioxidant capacity was comparable with that of BHA and green tea extract on the same weight concentration basis (75). These data suggest the potential application of pomegranate seed oil as anti-inammatory agent and for general health promotion. 7. SUMMARY There is an increasing demand for edible oils with special fatty acid proles and other benecial components for improving nutritional status. A number of studies have been conducted to screen for and evaluate the chemical composition and potential nutraceutical applications of fruit, spice, and herb seed oils. Among the discussed edible seed oils, some have unique fatty acid compositions, such as black raspberry and hemp seed oils rich in a-linolenic acid and date and naked seed squash seed oils rich in oleic acid, whereas blackcurrant seed oil is rich in g-linolenic acid. The oils of selected fruit, spice, and herb seeds may also contain signicant levels of phytosterols, tocopherols, carotenoids, and natural antioxidants. The chemical composition of edible seed oil determines the potential health benet and applications for the oil. Individual edible seed oils may be preferred by special groups of consumers for preventing and treating a selected health problem or for general health promotion. Great opportunities are available in the research and development of specialty seed oils and the oil-based nutraceutical products from fruit, spice, and herb seeds for improving human health. More research is required to screen and characterize the fatty acids and bioactive components in the fruit, spice, and herb seeds to develop novel edible seed oils for optimum human nutrition.

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