Attokaran M. Natural Food Flavors and Colorants

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206 Individual Flavors and Colorants

Wang , Xiuqin ; and Wang , Peixian . 2008 . Chemical constituents of Alpinia plants . Xibei Yaoxue Zazhi 23

( 2 ), C3 – C4 (Chinese) ( Chem. Abstr. 149:528591).

Zhuo , Xin - ming ; and Li , Bo - an . 2007 . Current research progress in the biological activity of ACA, a kind

of natural chemical compound . Guowai Yixue, Yaoxue Fence 34 ( 3 ), 181 – 186 (Chinese) ( Chem. Abstr.

148:345693).

Introduction

Because of its widespread availability, Kaempferia galanga is often referred to some-

what erroneously as “ lesser galanga. ” It is sometimes known as kencur or sand ginger.

In any case, it is one of the three or four “ false ” gingers, resembling galangal rhizome

in ﬂ avor and appearance. It is known to some botanists as “ resurrection lily. ” Generally,

however, it is referred to by its vernacular name.

The rhizome is ground and used in dishes in Bali. The leaves are ﬁ nely sliced and

eaten as a salad in Malaysia. Both the rhizome and leaves are used to ﬂ avor ﬁ sh

curries. Tender leaves are also eaten as a raw vegetable with shrimp paste.

Plant Material

K. galanga is glabrous, perennial, aromatic herb, which is generally pleasing to the

eye. It has two or more leaves which spread ﬂ at on the ground (Warrier 1993 ). The

petiole is very short, round - ovate, thin, and deep green. The ﬂ owers are white with

purple spots, in axillary fascicle with a corolla tube 2.5 cm in length and connected to

one another, producing a quadrate, two - lobed appendage. Its fruits are oblong, three -

celled and three - valved capsules with arillate seeds.

The aromatic undergrowth is the important part of the plant. This has one or more

prominent, vertically oriented, tuberous rootstocks. There can be many secondary

tubers and roots whose tips become tuberous. The rhizome, roots, and leaves have

medicinal properties. The rhizome is bitter, thermogenic, and acrid, and is a carmina-

tive, diuretic, expectorant, digestive, and stimulant. It is recommended for use in

Ayurvedic therapy. It has a peppery, camphoraceous ﬂ avor.

Essential Oil

On grinding using a roller mill, followed by steam distillation, the K. galanga rhizome

yields an essential oil of around 1%. The distillation time with steam at low pressure

is around 24 hours.

The oil is a light or greenish - brown mobile liquid with odor characteristic of the

rhizome, namely, peppery and camphoraceous. Physical characteristics obtained in the

author ’ s lab are as follows.

Galangal: Kaempferia

Kaempferia galanga L ( Zingiberaceae )

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208 Individual Flavors and Colorants

Optical rotation − 3 to − 6 ° at 25 ° C

Refractive index 1.4700 – 1.4855 at 25 ° C

Speciﬁ c gravity 0.8620 – 0.8850

The chemical analyses from a number of commercial producers of galangal oil

are presented in Table 52.1 . The most prominent constituent is ethyl - p - methoxy

cinnamate.

The volatile oil obtained by water distillation of K. galanga can be examined by

GC - MS (Tewtrakul et al. 2005 ). The major components identiﬁ ed are ethyl - p - methoxy

cinnamate (31.77%), methyl cinnamate (23.23%), carvone (11.13%), eucalyptol

(9.59%), and pentadecane (6.41%). While some antimicrobial activity is noticed,

antioxidant activity is negligible. Hot drying of the leaves of K. galanga generally

affects the antioxidant activity (Chan et al. 2009 ).

Uses

The rhizome of the K. galanga is widely used in the culinary practices of Southeast

Asia. In processed foods, the oil is the natural choice, because of freedom from

contamination and ease of standardization. The oil is also useful in medical

preparations.

References

Chan , E.W.C. ; Lim , Y.Y. ; Wong , S.K. ; Lim , K.K. ; Tan , S.P. ; Lianto , F.S. ; and Yong , M.Y. 2009 . Effects of

different drying methods on the antioxidant properties of leaves and tea of ginger spices . Food Chem.

113 ( 1 ), 166 – 172 .

Tewtrakul , S. ; Yuenyongsawad , S. ; Kummee , S. ; and Atsawajaruwan , L. 2005 . Chemical components and

biological activities of volatile oil of Kaempferia galanga Linn. Songklanakarin . J. Sci. Technol. 27 ( 2 ),

503 – 507 .

Warrier , P.K. 1993 . Indian Medicinal Plants . Madras : Orient Longman , vol. 3 , pp. 274 – 278 .

Table 52.1. Constituents of galangal oil

Constituents Content (%)

α - Pinene 1 – 2

Camphene 2 – 3

3 - Carene 8 – 14

Limonene 3 – 6

Ethyl - p - methoxy cinnamate 30 – 44

Introduction

This is another type of galangal (also written galanga) plant which is used in South

and Southeast Asia, both in cookery and in medicine. There is considerable confusion

about the different members of the galangal. This rhizome is popularly known as

“ China root. ” Lesser galangal differs from greater galangal ( Alpinia galanga ) and

Kaempferia galanga .

Long before the plant was botanically classiﬁ ed, the rhizome was in use in Europe

for over half a millennium. The root originated on Hainan Island in Southern China.

It was cultivated in the coastal regions of South China and was exported from

Shanghai. Like greater galangal, this root also has an Arabian connection; the name

“ galanga ” is derived from the Arabic. However, in many historical descriptions, the

three varieties of galangal roots are confused.

Even in use for cooking, the availability of the galangal plant may be the deciding

factor, as all three varieties have similar ﬂ avor characteristics of pungent and spicy

notes. They are all related to ginger, thereby justifying the name of “ false ginger ”

given to galangal roots.

Plant Material

The lesser galangal herb is about 2 m in height, with the elongated narrow leaves

characteristic of ginger. The leaf is parallel, smooth - veined, and sharply acuminate

with a length of about 30 cm and breadth of 5 – 10 cm. Flowers are simple terminal

spikes and have short, superior, and tubular calyx and white corolla consisting of three

lobes. There is a large ovate labellum with red veins. Each ﬂ ower has a single stamen

that bears the anther and a pistil with an inferior ovary and a thin style.

The lesser galangal rhizome itself has branches. The total length of the rhizome is

4 – 7 cm and its thickness less than 2 cm. Generally, they are cut transversely into

imperfect cylindrical shapes with whitish scars left by stems, which are removed. The

outside color is reddish brown, with pale colored inner matter. The aroma of the

rhizome is similar to other galangals, that is, peppery and pungent combined with a

camphoraceous note. The dried material is tough and difﬁ cult to break.

Earlier literature shows starch as a major component. It has a volatile oil and resin-

ous component containing nonvolatile fractions such as galangal, galangin, and

Galangal: Lesser

Alpinia ofﬁ cinarum Hance ( Zingiberaceae )

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210 Individual Flavors and Colorants

kaempferid. Galangin is a dioxyﬂ avanol. Kaempferid actually consists of three parts,

fusing at 220 ° C, insoluble in water but soluble in ether.

China root galangal is a stimulant, carminative, and ﬂ atulent. It is useful in treating

stomach disorders, vomiting, and fever. It is a good medicine for cattle.

Essential Oil

Very limited information is available about commercial production of lesser galangal ’ s

volatile oil. However, there is a report from Indrayan et al. (2007) about the analysis

of oil obtained by hydrodistillation of the rhizome collected from West Bengal, India.

1,8 - Cineole (53.39%) is the major constituent. Also reported are δ - 3 - carene (8.96%),

β - pinene (4.29%), camphene (2.81%), limonene (2.80%), isocaryophyllene (2.52%),

camphor (2.35%), α - pinene (2.27%), γ - terpinene (2.23%), and γ - cardinene (2.17%).

The oil also shows antibacterial activity against both gram - positive and gram - negative

bacteria and antifungal activity against Candida albicans .

Uses

The rhizome is used in many culinary practices in Asia. The oil has a convenient ﬂ avor

for use in processed foods. In addition, extracts with medicinal properties can be

developed.

Reference

Indrayan , A.K. ; Garg , S.N. ; Rathi , A.K. ; and Sharma , V. 2007 . Chemical composition and antimicrobial

activity of Alpinia ofﬁ cinarum rhizome . Indian J. Chem. B Org. Chem. 468 ( 12 ), 2060 – 2063 .

Introduction

In recent years, the garcinia fruit has attracted much attention because of the ability

of the acid from the fruit to control the weight of its consumer. However, the fruit,

popularly known as “ Malabar tamarind, ” has for years been a favorite in South Asia

as a much liked acidulant in food. People of Southwest India and Sri Lanka use the

dried rind in ﬁ sh curries and other food preparations. To some extent, it is an acquired

taste as its sourness is combined with astringency. It is believed that its high level of

acid can preserve food very effectively. In the days before the refrigerator became a

household item this was an important consideration.

Garcinia also makes food satisfying and ﬁ lling. Generally, in the ancient Ayurvedic

system of medicine, acidic foods activate the metabolism. In ancient times, the natural

gum oleoresin that oozes out from the bark was used for various ointments.

However, it is the fruit that is used as a seasoning and can yield an extract that

becomes a ﬂ avor. The fact that the fruit has special properties to guide metabolism to

effectively control fat accumulation and weight gain is a further bonus.

Plant Material

The garcinia plant is a small evergreen tree. It has a rounded crown and relatively

drooping horizontal branches (Majeed et al. 1994 ). The tree, whose trunk has smooth

bark, attains a height of 5 – 8 m. The leaves are shining dark green and elliptical to

oval - shaped. The ﬂ owers are unisexual, sessile, and axillary. It has four yellowish and

rounded sepals and an equal number of large, rose - colored petals. It has four - or eight -

celled and globular ovaries.

Though smaller in size, the fruit resembles a small yellowish - or reddish - colored

pumpkin in shape. The sweet and sour tasting fruit is globular and has juicy white

pulp inside. The rind is thick and tough. Embedded in the pulp are six to eight seeds.

On drying, the fruit assumes a near black color. It is tougher and less pulpier than

tamarind. Photo 16 shows the garcinia fruit and dried pulp.

Chemistry

About 30% of the fruit is made up of an acid, which has been identiﬁ ed as ( – )hydroxy-

citric acid (Lewis and Neelakantan 1965 ). The structure of this acid is presented in

Garcinia Fruit

Garcinia cambogia Desr ( Guttiferae )

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Photo 16. (A) Garcinia fruit. (B) Dried pulp. See color insert.

212

54 Garcinia Fruit 213

Fig. 54.1 . Hydroxycitric acid is a derivative of citric acid and is found in some tropical

fruits. On storage it can convert into a lactone. The characteristic compound cambogin

has been identiﬁ ed (Rama Rao et al. 1980 ).

Extract

The garcinia fruit has no essential oil. The dried fruit can be extracted with boiling

water. After extraction is repeated three or four times, the extracts are combined,

strained through a suitable ﬁ lter, and concentrated through the evaporation of water.

The thick extract with total soluble solids of 60 – 70 ° Brix comes out as a dark syrupy

liquid. This is used as the ﬂ avor concentrate.

In recent years, emphasis has shifted to the hydroxycitric acid that can be obtained

from the fruit. The acid readily undergoes lactone formation. Lactone is not an effec-

tive chemical for intervention in fat formation. To avoid this, the acid is converted to

a calcium salt, which is more popular, although a potassium derivative can also

be made.

The extraction is done in a stainless steel boiling kettle with a batch size of 300 –

600 kg. Generally, three times the plant ’ s weight in water is used for extraction. About

half the quantity of water is added in the ﬁ rst extraction and the remaining in two

parts in the subsequent extractions. The mixture is heated with a steam jacket and

stirring. The soluble constituents, mainly hydroxycitric acid, go into the water mis-

cella. This is decanted and kept aside. A further two extractions are carried out. The

extraction is done at a temperature of 60 – 70 ° C. The combined extract is concentrated

and then treated with sodium hydroxide to bring the pH to between 8 and 9, while

temperature is maintained at 70 ° C. A calculated quantity of calcium chloride is added

to convert the acid to the calcium derivative. The calcium salt is carefully washed to

remove any excess chemicals. However, excessive or careless washing will remove

some valuable calcium derivative of hydroxycitric acid, which is slightly soluble. A

convenient form of ﬁ ltration and washing is by using a basket centrifuge ﬁ tted with

ﬁ lter cloth. When freed of water, the wet cake is removed and dried in a cabinet dryer

at 90 – 100 ° C. The dry cake is ground to a powder as per customer speciﬁ cation. Since

the calcium hydroxycitrate is used in capsule form, the bulk density has to be adjusted

to ﬁ ll the appropriate capsule.

The calcium derivative of ( – )hydroxycitric acid is a pale brownish - gray powder

with mildly salty taste but with no odor. The particle size is adjusted as per customer

speciﬁ cation. A bulk density of 0.5 – 0.7 g/mL is typical.

The moisture content is kept below 6% for optimal storage. The calcium content

is generally between 18% and 21%. Hydroxycitric acid determined by HPLC using a

Figure 54.1. Hydroxycitric acid.

HOH

214 Individual Flavors and Colorants

pure standard is required to be, as per market need, between 55% and 65%. On dis-

solving at 10% level, the pH must be between 8 and 10.

Mechanism of Action

During metabolism, in the Krebs cycle, citrates are converted into acetyl coenzyme

A with the help of an enzyme system, citrate lyase (Majeed et al. 1994 ). When ( – )

hydroxycitrate is fed during this phase, part of the enzyme will be utilized by this

acid, and thereby formation of acetyl coenzyme A is slowed. The acetyl unit is the

building block of fat synthesis. Therefore, consumption of ( – )hydroxycitric acid brings

about a slowing of fat synthesis and hence fat accumulation. But for effective inter-

vention, hydroxycitric acid has to be in straight chain form and not as a lactone. This

is achieved by conversion to a metal derivative. Calcium hydroxycitrate is liberated

to free acid which remains in straight chain form for some time so that it can function

effectively. The best time to take the calcium salt is about 1 hour before the main meal.

In the marketing process, some micronutrients are added to increase its value. Calcium

itself is a good nutrient, and for this reason potassium salt has disadvantages.

Recently, the role of hydroxycitric acid as an inhibitor of ATP - citrate lyase, as well

as its structure and characteristics, has been reviewed (Yamada et al. 2007 ).

Uses

The water extract of the Malabar tamarind can be used in place of the fruit itself. The

extract can be used even in places where fruits are not available. The extract is par-

ticularly appreciated by South Indians who have settled abroad, as they can procure

their favorite seasoning for use in their well - liked ﬁ sh curries. The extract, being

acidic, will help in preservation of food preparations.

The garcinia fruit ’ s greatest value is its use as a supplement to regulate weight. The

calcium derivative when taken before the main meals helps in regulating metabolism

to reduce formation of triglycerides.

References

Lewis , Y.S. ; and Neelakantan S. 1965 . ( - )Hydroxy citric acid — the principal acid in the fruits of Garcinia

cambogia Desr . Phytochemistry 4 , 619 – 625 .

Majeed , Muhammed ; Rosen , Robert ; McCarty , Mark ; Conte , Anthony ; Patel , Dilip ; and Butrym , Eryc .

1994 . Citrin: A Revolutionary, Herbal Approach to Weight Management . Burlingame, CA : New Editions ,

pp. 1 – 69 .

Rama Rao , A.V. ; Venkataswamy , G. ; and Pendre , A.D. 1980 . Comboginol and combogin . Tetrahedron Lett.

21 , 1975 – 1978 .

Yamada , Takashi ; Hida , Hiroyuki ; and Yamada , Yasuhiro . 2007 . Chemistry, physiological properties and

microbial production of hydroxy citric acid . Appl. Microbiol. Biotechnol . 75 ( 5 ), 977 – 982 .

Introduction

Garlic belongs to the onion family. It was known to ancient Romans and Egyptians,

was referred to in writings from the time of Moses, and is believed to have originated

in West Asia. In the pre - Christian era, citizens of Greece and Rome thought that garlic

had supernatural qualities; thus, sailors carried it hoping that it would save them from

the dangers of the sea. There is mention that Israelites developed a taste for garlic

during their journey from Egypt.

Though many diverse qualities were attributed to garlic by ancient people, its

primary value is for food ﬂ avoring. There are, however, groups of people who detest

its ﬂ avor and avoid its consumption. Some elite groups in China used to consider

garlic ﬂ avor in food as objectionable as it causes an offensive smell in the breath of

people who eat it.

Plant Material

Garlic is the underground bulb of a perennial plant with ﬂ at leaves and small white

ﬂ owers. Since the valued part of the plant is under the earth, the plant has to be pulled

out of the ground to be used, so in effect it needs replanting each season. The bulb

consists of 6 – 35 smaller bulblets called “ cloves ” which are surrounded by a thin white,

yellow, or pink paper - like sheath. Photo 16 shows the garlic bulb and cloves.

Garlic needs a slightly richer soil than does the onion. A well - drained, moderately

clayey soil is suitable. Ideally, it needs a cool, humid period for growth and a relatively

dry season while maturing. The crop will be ready in 4 – 5 months, when the top turns

slightly yellow or brown. After plucking from the earth, the bulbs are cured for

3 – 4 days in the shade before being stored in ambient conditions after removing the

top vegetative parts.

Garlic is grown in many different regions of the world which are free of extremes

of climate. The largest producer of garlic is China, which, according to statistics,

grows 75% of the estimated world production of 15,000 – 16,000 tonnes. Other produc-

ers are India (4%), South Korea (2%), Russia (1.6%), and the United States (1.4%).

In the United States, most production is centered around Gilroy in California, which

calls itself the “ Garlic Capital of the World. ” However, with the development of

Silicon Valley and consequent growth of building construction, that position is fast

changing.

Garlic

Allium sativum L ( Alliaceae )

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