**Application of Saponin-Containing Plants in Foods and Cosmetics**

Yukiyoshi Tamura, Masazumi Miyakoshi and Masaji Yamamoto

Additional information is available at the end of the chapter

http://dx.doi.org/10.5772/53333

## **1. Introduction**

Saponins are a class of natural products which are structurally constructed of aglycone (tri‐ terpene or steroid) and sugars (hexose and/or uronic acid). The name 'saponin' comes from soap as its containing plants agitated in water form soapy lather. Saponins are widely dis‐ tributed in many plants and are relatively widespread in our foodstuffs and herbal prepara‐ tions. Saponins traditionally used as a natural detergent. In addition to this physical property, plant-derived triterpenoid and steroidal saponins have historically received a number of industrial and commercial applications ranging from their use as sources of raw materials for the production of steroid hormones in the pharmaceutical industry, to their use as food additives and as ingredients in photographic emulsions, fire extinguishers and other industrial applications which take advantage of their generally non-ionic surfactant proper‐ ties [1-3]. They also exhibit a variety of biological activities, and have been investigated to‐ ward the development of new natural medicines and prove the efficacy of traditional herbal medicines [4]. Other interesting biological applications for various specific saponins include their uses as anti-inflammatory [5], hypocholesterolemic [6] and immune-stimulating [7] whose properties are widely recognized and commercially utilized.

As to the application of saponins to foods and cosmetics, it is indispensable that sufficient amounts of plant resources are available, and that the content of saponins must be high. Fur‐ thermore, a plant must have a long history of human use as foodstuffs or ingredients of cos‐ metics, and their safety should be officially guaranteed.

The saponins of Quillaja bark and licorice root are widely utilized in the world. The *Quillaja saponaria* (Rosaceae) tree has remained of special interest, because of its bark containing 9-10

© 2012 Tamura et al.; licensee InTech. This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. © 2012 The Author(s). Licensee InTech. This chapter is distributed under the terms of the Creative Commons Attribution License http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

% saponins. A large amount of Quillaja saponin is utilized in photosensitized film as a sur‐ factant. It is used also in beverages, food ingredients, shampoos, liquid detergents, tooth‐ pastes and extinguishers as an emulsifier and long-lasting foaming agent. Recently, the saponin mixture possesses the immunoadjuvant property and has pharmaceutical applica‐ tion as suspension stabilizer [8].

**3.** *Sapindus* **pericarps**

are shown in Figure 1.

zi-saponin Y1 showed no activity.

candidiasis.

Addition of an antifungal and antiyeast ingredient to cosmetics is desirable for the protec‐ tion of skin against, and prevention of, dandruff generation, dermatomycosis and cutaneous

Application of Saponin-Containing Plants in Foods and Cosmetics

http://dx.doi.org/10.5772/53333

87

Significant antiyeast activity was observed for the crude saponin fraction from the pericarps of *Sapindus mukurossi* (Sapindaceae), a tall tree that grows abundantly in China and Japan. Pericaps of this plant have been used as a natural detergent, and are utilized as foamingstabilizing agents in chemical fire extinguishers in Japan. The pericarps have also been used as an antitussive, anti-inflammatory and anthelmintic agent as well as for treatment of der‐ matomycosis. In Japan, the pericarps is called "enmei-hi", which means "life prolonging pericarps", and in China, it has been called "wu-huan-zi", which means "non-illness fruit".

**4. Antifungal and antiyeast oleanane-saponins of** *Sapindus* **pericarps**

The percarps were extracted with hot 90% MeOH. A suspension of the MeOH-extract in H2O was chromatographed on a column of highly porous polymer (Diaion H-20) eluting with H2O and 50%- and 85%-MeOH, successively. 85%-MeOH eluate gave a saponin-mix‐ ture (mono- and bis-desmosides, SP-mix). Hederagenin (1) was obtained from SP-mix by usual acid hydrolysis. Saponins 2-7 were isolated from SP-mix, such as monodesmosides: saponin A (2), sapindoside B (3), saponin C (4), sapindoside A (5), mukurozi-saponin E1 (6) etc. and bisdesmosides: mukurozi-saponin Y1 (7) etc. [10]. The structures of these saponins

Antidermatophytic activities of these saponins are shown in Table 2. All the monodesmo‐ sides exhibited strong growth inhibition. It is noteworthy that activity of sapindoside A is almost as strong as that of griseofulvin, the well-known antidermatophytic antibiotic. Gri‐ seofulvin does not show inhibitory activity against a pathogenic yeast, *Candida albicans*, while these monodesmosides ehhibited significant inhibition. The bisdesmosides, mukuro‐

It was found that while purified monodesmosides of pericarps are sparingly soluble in wa‐ ter, their solubility was greatly increased in the presence of bisdesmosides [10]. These phe‐

Figure 1 showed antidermatophytic activity against *Tricophyton rubrum* was investigated for a variety of oleanane saponins. Saponins 8-10 were separated from roots of *Anemone rivularis* [11]. Saponins 11-13 were isolated from bupleurum roots [12], and saponins 14 and 15 were prepared from 11 and 12, respectively by the reference [13]. Saponin 16 was isolated from

nomena are important for the biological activities of the pericarps.

**5. Structure-antifungal activity relationship**

Nearly 50,000 tons of licorice roots (*Glycyrrhiza* spp., Leguminosae) are consumed on a year basis. Licorice extract and its major saponin, glycyrrhizin (yield: more than 2.5%), are used as a medicine and as a sweetener and flavor enhancer in foods and cigarettes [9].

It is known that the deterioration of cooked foods is caused mainly by yeast, and that many skin diseases are due to infection by dermatophytic fungi and yeasts. In an expansion of utilization of saponins in foods and cosmetics, we have examined antifungal and antiyeast saponins.

## **2. Screening of antiyeast saponins**

Crude saponin fractions from several plants were subjected to an antiyeast screening test us‐ ing *Candida albicans* and/or *Saccharomyces cerevisiae*. Preparation of saponin fraction for screening test was following methods. Each plant material was extracted with hot 50% of MeOH. A suspension of the MeOH-extract in H2O was chromatographed on a column of Diaion HP-20 eluting with 40%-, and MeOH. The MeOH eluate (crude saponin fraction) was subjected to the screening test.

Inhibitory activity against each yeast was determined using agar dilution method. The in‐ hibitory activity of the samples was assessed as the minimum inhibitory concentration (MIC), the lowest concentration tested at which no growth was observed.

Table 1 shows the screening results of antiyeast activity tests of crude saponin mixtures from several plants. The saponin fraction from licorice root, quillaja bark, gypsophila root and soy bean seed showed no activity (MIC:>1000μg/ml) and that of hedera leaf, marronier seed, ginseng root, camellia seed, saponaria rhizome and tea seed showed a weak activity (MIC:500∼1000μg/ml), wheras crude saponin fraction from pericarps of *Sapindus mukurossi* and the stems of Mohave yucca exhibited significant activity, the active principles of both these materials were further investigated in detail.


*C.a: Candida albicans, S.c.: Saccharomyces cerevisiae*, NT: not tested

**Table 1.** Antiyeast activities of crude saponin fractions (MIC μg/ml)

## **3.** *Sapindus* **pericarps**

% saponins. A large amount of Quillaja saponin is utilized in photosensitized film as a sur‐ factant. It is used also in beverages, food ingredients, shampoos, liquid detergents, tooth‐ pastes and extinguishers as an emulsifier and long-lasting foaming agent. Recently, the saponin mixture possesses the immunoadjuvant property and has pharmaceutical applica‐

Nearly 50,000 tons of licorice roots (*Glycyrrhiza* spp., Leguminosae) are consumed on a year basis. Licorice extract and its major saponin, glycyrrhizin (yield: more than 2.5%), are used

It is known that the deterioration of cooked foods is caused mainly by yeast, and that many skin diseases are due to infection by dermatophytic fungi and yeasts. In an expansion of utilization of saponins in foods and cosmetics, we have examined antifungal and antiyeast saponins.

Crude saponin fractions from several plants were subjected to an antiyeast screening test us‐ ing *Candida albicans* and/or *Saccharomyces cerevisiae*. Preparation of saponin fraction for screening test was following methods. Each plant material was extracted with hot 50% of MeOH. A suspension of the MeOH-extract in H2O was chromatographed on a column of Diaion HP-20 eluting with 40%-, and MeOH. The MeOH eluate (crude saponin fraction) was

Inhibitory activity against each yeast was determined using agar dilution method. The in‐ hibitory activity of the samples was assessed as the minimum inhibitory concentration

Table 1 shows the screening results of antiyeast activity tests of crude saponin mixtures from several plants. The saponin fraction from licorice root, quillaja bark, gypsophila root and soy bean seed showed no activity (MIC:>1000μg/ml) and that of hedera leaf, marronier seed, ginseng root, camellia seed, saponaria rhizome and tea seed showed a weak activity (MIC:500∼1000μg/ml), wheras crude saponin fraction from pericarps of *Sapindus mukurossi* and the stems of Mohave yucca exhibited significant activity, the active principles of both

Licorice root >1000 >1000 Ginseng root 1000 1000 Quillaja bark >1000 >1000 Camellia seed 1000 1000 Gypsophila root >1000 >1000 Saponaria rhizome NT 1000 Hedera leaf 1000 1000 Tea seed 500 500 Soy been seed NT >1000 Yucca stem NT 250 Marronier seed 1000 1000 Sapindus pericarp 250 250

**C.a. S.c. C.u. S.c.**

(MIC), the lowest concentration tested at which no growth was observed.

as a medicine and as a sweetener and flavor enhancer in foods and cigarettes [9].

tion as suspension stabilizer [8].

86 Alternative Medicine

**2. Screening of antiyeast saponins**

these materials were further investigated in detail.

*C.a: Candida albicans, S.c.: Saccharomyces cerevisiae*, NT: not tested

**Table 1.** Antiyeast activities of crude saponin fractions (MIC μg/ml)

subjected to the screening test.

Addition of an antifungal and antiyeast ingredient to cosmetics is desirable for the protec‐ tion of skin against, and prevention of, dandruff generation, dermatomycosis and cutaneous candidiasis.

Significant antiyeast activity was observed for the crude saponin fraction from the pericarps of *Sapindus mukurossi* (Sapindaceae), a tall tree that grows abundantly in China and Japan. Pericaps of this plant have been used as a natural detergent, and are utilized as foamingstabilizing agents in chemical fire extinguishers in Japan. The pericarps have also been used as an antitussive, anti-inflammatory and anthelmintic agent as well as for treatment of der‐ matomycosis. In Japan, the pericarps is called "enmei-hi", which means "life prolonging pericarps", and in China, it has been called "wu-huan-zi", which means "non-illness fruit".

## **4. Antifungal and antiyeast oleanane-saponins of** *Sapindus* **pericarps**

The percarps were extracted with hot 90% MeOH. A suspension of the MeOH-extract in H2O was chromatographed on a column of highly porous polymer (Diaion H-20) eluting with H2O and 50%- and 85%-MeOH, successively. 85%-MeOH eluate gave a saponin-mix‐ ture (mono- and bis-desmosides, SP-mix). Hederagenin (1) was obtained from SP-mix by usual acid hydrolysis. Saponins 2-7 were isolated from SP-mix, such as monodesmosides: saponin A (2), sapindoside B (3), saponin C (4), sapindoside A (5), mukurozi-saponin E1 (6) etc. and bisdesmosides: mukurozi-saponin Y1 (7) etc. [10]. The structures of these saponins are shown in Figure 1.

Antidermatophytic activities of these saponins are shown in Table 2. All the monodesmo‐ sides exhibited strong growth inhibition. It is noteworthy that activity of sapindoside A is almost as strong as that of griseofulvin, the well-known antidermatophytic antibiotic. Gri‐ seofulvin does not show inhibitory activity against a pathogenic yeast, *Candida albicans*, while these monodesmosides ehhibited significant inhibition. The bisdesmosides, mukuro‐ zi-saponin Y1 showed no activity.

It was found that while purified monodesmosides of pericarps are sparingly soluble in wa‐ ter, their solubility was greatly increased in the presence of bisdesmosides [10]. These phe‐ nomena are important for the biological activities of the pericarps.

## **5. Structure-antifungal activity relationship**

Figure 1 showed antidermatophytic activity against *Tricophyton rubrum* was investigated for a variety of oleanane saponins. Saponins 8-10 were separated from roots of *Anemone rivularis* [11]. Saponins 11-13 were isolated from bupleurum roots [12], and saponins 14 and 15 were prepared from 11 and 12, respectively by the reference [13]. Saponin 16 was isolated from roots of *Kalopanax septemlobus* [14]. Saponin 17-20 were isolated from brans of *Chenopodium quinoa* [15, 16], and saponin 21 from rhizome of *Thladiantha hookeri* var. *pentadactyla* [17], de‐ rivative 1 (22) was prepared from 21, and derivative 2 (23) from 22 [16].

nin fraction against common fungi was not so strong, while it exhibited remarkable growthinhibitory effects against the following dermatophytic fungi and pathogenic yeast, *Tricophyton rubrum*, *T. mentagrophytes*, *Sabouraudites canis*, and *Epidermophyton floccosum* (which are known as dermatophytic fungi) and against *Candida albicans*, a pathogenic yeast

5

Me COOMe Me COOMe Me

R3


**MIC** (μg/ml)

R3

H H

which causes cutaneous candidiasis.

R1O

RO

R1O

R1O

R1O

R1O

R2

CH2OH

23

3

O

CH2OH

CH2OH

R2

COOR2

COOR'

28

**8**. Saponin CP4 **9**. Huzhangoside A **10**. Huzhangoside B

**11**.Saikosaponin a **12**. Saikosaponin b **13**. Saikosaponin c

> **14.** Saikosaponin b1 **15**. Saikosaponin b2


R1

**1.** hederagenin <sup>H</sup> **2.** Saponin A -Ara(p)-2-Rha-3-Ara(p) **3.** Sapindoside B -Ara(p)-2-Rha-3-Xyl **4.** Saponin C -Ara(p)-2-Rha-3-Ara(f) **5.** Sapindoside A -Ara(p)-2-Rha **6.** Mukurozi-saponin E1 -Ara-(p)-2-Rha-3-Xyl-4-Ac **7.** Mukurozi-saponin-Y1 -Ara(p)-2-Rha-3-Xyl

CH2OH CH2OH Me

R2 R3


R1 R2



R1 R2



R1 R2


CHO CH2OH CH2OH CH2OH


R1

H H -(Glc)2-Rha

R2

R R'

Application of Saponin-Containing Plants in Foods and Cosmetics

http://dx.doi.org/10.5772/53333

89

H H H H H H -Glc-2- Glc

**MIC**(μg/ml) **>400 >400 >400**

**MIC**(μg/ml)

**MIC**(μg/ml)

**MIC**(μg/ml)

**MIC**(μg/ml)

**>400 >400**

**>400 >400 >400**

**>400 >400 >400 >400 >400**

**>400 >400 >400 >400**


CH2OH

COOR2

COOR3

**Figure 1.** Structure and antifungal activities of saponins on *Tricophyton rubrum*

. Kalopanax-saponin B . Quinoa-saponin 3 . NH-saponin F . Quinoa-saponin 4 . Quinoa-saponin 2

**21.** Thlandioside H1 . derivative 1 . derivative 2 . Hederagenin-3-Ara

Figure 1 Structure and antifungal activities of saponins on *Tricophyton rubrum*

R2

R3

R3

It was disclosed that for growth inhibition, the presence of free 28-COOH, 23-OH and 3-*O*-gly‐ cosyl groups is essential (Figure 2). A sugar moiety was prerequisite for the antifungal activity of oleanane saponin. All the bisdesmosides of hederagein, such as kalopanaxsaponin B (16), the 28-COOH of which is glycosylated, showed no activity. Mono- and bisdesmosides of olea‐ nolic acid, such as saponin CP4 (8), which lack a 23-OH, also showed no growth inhibition. Sai‐ kosaponins, the active principles of *Bupleurum* radix, lack a 28-COOH, exhibiting no activity. Thalandioside H1 (21), a bisdesmoside which was isolated from *Thandiantha hookeri* var. *penta‐ phyla* in yield of 10% without any chromatography (Nie et al., 1989), showed no activity, while a monodesmoside of hederagein derived from this bisdesmoside, exhibited activity. Activity was also obserbed for hederagenin-3-*O*-α-L-arabinoside (24) which was prepared from 17 [18].


**Table 2.** Antimicrobial activities of saponins and saponin mixture (**SP-mix**) against dermatophytes (**MIC**:μg/ml)

## **6. Antimicrobial activity of the saponin fraction of** *Sapindus* **pericarps**

For commercial utilization as ingredient in cosmetics, the saponin fraction was prepared as follows. The methanolic extract was subjected to chromatography on Diaion HP-20. After re‐ moval of other water-soluble constituents by elution with water and then 50% of MeOH, the saponin fraction was obtained by elution with 80% MeOH.

The saponin fraction showed moderate antibacterial activity against Gram-positive bacteria, while no activity was obserbed against Gram-negative bacteria (Table 3).

A summarized in Table 4, the saponin fraction exhibited growth inhibition against food de‐ teriorating yeasts, *Pichia nakazawae*, *Debaryomyces hansenii* and *Hansenula anomala*, as well as against *Malassezia furfur* which is associated with dandruff generation. The activity of sapo‐ nin fraction against common fungi was not so strong, while it exhibited remarkable growthinhibitory effects against the following dermatophytic fungi and pathogenic yeast, *Tricophyton rubrum*, *T. mentagrophytes*, *Sabouraudites canis*, and *Epidermophyton floccosum* (which are known as dermatophytic fungi) and against *Candida albicans*, a pathogenic yeast which causes cutaneous candidiasis.

roots of *Kalopanax septemlobus* [14]. Saponin 17-20 were isolated from brans of *Chenopodium quinoa* [15, 16], and saponin 21 from rhizome of *Thladiantha hookeri* var. *pentadactyla* [17], de‐

It was disclosed that for growth inhibition, the presence of free 28-COOH, 23-OH and 3-*O*-gly‐ cosyl groups is essential (Figure 2). A sugar moiety was prerequisite for the antifungal activity of oleanane saponin. All the bisdesmosides of hederagein, such as kalopanaxsaponin B (16), the 28-COOH of which is glycosylated, showed no activity. Mono- and bisdesmosides of olea‐ nolic acid, such as saponin CP4 (8), which lack a 23-OH, also showed no growth inhibition. Sai‐ kosaponins, the active principles of *Bupleurum* radix, lack a 28-COOH, exhibiting no activity. Thalandioside H1 (21), a bisdesmoside which was isolated from *Thandiantha hookeri* var. *penta‐ phyla* in yield of 10% without any chromatography (Nie et al., 1989), showed no activity, while a monodesmoside of hederagein derived from this bisdesmoside, exhibited activity. Activity was also obserbed for hederagenin-3-*O*-α-L-arabinoside (24) which was prepared from 17 [18].

rivative 1 (22) was prepared from 21, and derivative 2 (23) from 22 [16].

*Trichophyton mentagrophytes*

saponin fraction was obtained by elution with 80% MeOH.

while no activity was obserbed against Gram-negative bacteria (Table 3).

\* positive control

88 Alternative Medicine

*T. rubrum*

**SP-mix** 25 25 25 12.5 50 . saponin A 6.25 6.25 6.25 3.13 12.5 . sapindoside B 6.25 6.25 3.13 3.13 12.5 . saponin C 6.25 6.25 6.25 3.13 25 . sapindoside A 3.13 1.56 3.13 1.56 12.5 . mukurozi-saponin E1 6.25 6.25 6.25 3.13 12.5 . Mukurozi-saponin Y1 >100 >100 >100 >100 >100 . Hederagenin >100 >100 >100 >100 >100 griseofulvin\* 3.13 1.56 0.78 1.56 >100

**Table 2.** Antimicrobial activities of saponins and saponin mixture (**SP-mix**) against dermatophytes (**MIC**:μg/ml)

**6. Antimicrobial activity of the saponin fraction of** *Sapindus* **pericarps**

For commercial utilization as ingredient in cosmetics, the saponin fraction was prepared as follows. The methanolic extract was subjected to chromatography on Diaion HP-20. After re‐ moval of other water-soluble constituents by elution with water and then 50% of MeOH, the

The saponin fraction showed moderate antibacterial activity against Gram-positive bacteria,

A summarized in Table 4, the saponin fraction exhibited growth inhibition against food de‐ teriorating yeasts, *Pichia nakazawae*, *Debaryomyces hansenii* and *Hansenula anomala*, as well as against *Malassezia furfur* which is associated with dandruff generation. The activity of sapo‐

*Epidermophyton floccosum*

*Sabouraudites*

*Candida albicans*

*canis*

5

**MIC** (μg/ml)

**Figure 1.** Structure and antifungal activities of saponins on *Tricophyton rubrum*

Figure 1 Structure and antifungal activities of saponins on *Tricophyton rubrum*

**Figure 2.** Structure-antimicrobial activity relationship of oleanane-type saponin analogues


7

It is difficult to use *Sapindu*s saponin fraction as a food ingredient without long-term toxicity test, because we have no history of this fraction or *Sapindus* extract as a foodstuff. Furthr‐ more, it tastes very bitter, changing the taste of foods. On the other hand, the extract has been used as a folk detergent,and is listed in the Japanese Cosmeic Ingredient Codex (JCIC), being authorized as an ingredient in cosmetics by the Ministry of Health and Welfare in Ja‐ pan. We reconfirmed the safety of the saponin fraction by dermal toxicity tests. It did not show primary dermal irritant, sentitization, phototoxicity or photosensitization effects. The present study strongly suggests that the saponins of the pericarps as an ingredient in toilet‐ ries, are valuable not only as detergents, but also for the prevention of dermatomycosis, cu‐

*Yucca* species (Agavaceae), grows widely in North and Central America. Mohave yucca, *Y. schidigera*, has been used as a foodstuff and folk medicine by Native Americans as well as early California settlers to treat a variety of ailments including arthritis and inflammation [3], and is approved for use in food and beverages by the U.S. Food and Drug Administra‐

 R1 R2 R3 R1 R2 R3 R4 schidigera-saponin A1 H S1 H2 **31** schidigera-saponin D1 H S1 H2 eq + ax Me schidigera-saponin A2 H S2 H2 **32** schidigera-saponin D2 H S2 H2 eq + ax Me schidigera-saponin A3 H S3 H2 **33** schidigera-saponin D3 H S3 H2 eq + ax Me schidigera-saponin B1 H S1 O **34** schidigera-saponin D4 H S5 H2 eq + ax Me schidigera-saponin C1 OH S2 H2 **35** schidigera-saponin D5 H S6 H2 eq + ax Me schidigera-saponin C2 OH S4 H2 **36** schidigera-saponin E1 H S1 O eq + ax Me **37** schidigera-saponin F1 OH S2 H2 eq + ax Me

R2O

H

O

O O

OH

O

O O

OH

CH2OH

**Glc'**

**Glc'**

CH2OH

O

O

HO

CH2OH

OH **Gal**

HO

CH2OH

OH **Gal**

O

HOHO

O

HOHO

R3

R1

O

R2O

H

19

R3

18

21

12

R1

2 3 5 O

25

27

**38** schidigera-saponin F2 OH S4 H9 eq + ax Me

Application of Saponin-Containing Plants in Foods and Cosmetics

**Glc"**

CH2OH

HOHO

O

O O

OH

O

O O

OH

CH2OH

CH2OH

**Glc'**

**Glc**

**Glc'**

CH2OH

O

http://dx.doi.org/10.5772/53333

HO

HO

HO

CH2OH

OH **Glc**

O

HOHO

HOHO

O

O

R4

91

Figure 3 Saponins from Mohave yucca

**Figure 3.** Saponins from Mohave yucca

O

O O

OH

O

O O

OH

CH2OH

CH2OH

**Glc'**

HO CH2OH

**Gal**

**Glc'**

taneous candidiasis as well as for dandruff generation.

**8. Mohave Yucca (Yucca schidigera)**

HOHO

HOHO

**Xyl**

**S1: S2: S3:**

**Glc"**

**S4: S5: S6:**

**7.** *Sapindus* **saponin fraction as an antidermatophytic ingredient in**

CH2OH

O

HO

CH2OH

OH **Glc**

HO

HOHO

HOHO

O

HOHO

**Xyl**

**cosmetics**

**Table 3.** Antibacterial activity of saponin mixture (SP-mix)


**Table 4.** Antiyeast and antifungal activity of saponin Mixture (**SP-mix**)

O

O

R4

**38** schidigera-saponin F2 OH S4 H9 eq + ax Me

 R1 R2 R3 R1 R2 R3 R4 schidigera-saponin A1 H S1 H2 **31** schidigera-saponin D1 H S1 H2 eq + ax Me schidigera-saponin A2 H S2 H2 **32** schidigera-saponin D2 H S2 H2 eq + ax Me schidigera-saponin A3 H S3 H2 **33** schidigera-saponin D3 H S3 H2 eq + ax Me

R2O

H

R3

R1

O

R2O

H

19

R3

18

21

12

R1

2 3 5 O

25

27

**30** schidigera-saponin C2 OH S4 H2 **36** schidigera-saponin E1 H S1 O eq + ax Me **37** schidigera-saponin F1 OH S2 H2 eq + ax Me

**Figure 3.** Saponins from Mohave yucca

Figure 3 Saponins from Mohave yucca

COOH

28

CH2OH

**Gram-positive, MIC:μg/ml Gram-negative, MIC:μg/ml**

*aureus* IID 671 400 *Escherichia coli* HUT 215 >400

*epidermidis* IID 866 400 *Pseudomonas aeruginosa* JCM 2776 >400

*Streptococcus mutans* IFO 13955 400 *Alcaligenes faecalis* IFO 13111 >400

*Bacillus subtilis* IFO 3007 400 *Proteus vulgaris* IFO 3851 >400

**Yeast**, **MIC:μg/ml**

*Saccharomyces cerevisiae* IFO 0203 100 *Candida utilis* IFO 0396 100

*Pichia nakazawae* HUT 1688 50 *Hansenula anomala* HUT 7083 50

*Malassezia furfur* IFO 0656 200 *Debaryomyces hansenii* IFO 0018 >400

**Fungi**, **MIC:μg/ml**

*Aspergillus niger* IFO 4343 >400 *Rhizopus nigricans* IFO 4731 >400

*Mucor pusillus* HUT 1185 100 *Penicillium citrinum* IFO 4631 >400

23

3

**Figure 2.** Structure-antimicrobial activity relationship of oleanane-type saponin analogues

RO

**Table 3.** Antibacterial activity of saponin mixture (SP-mix)

**Table 4.** Antiyeast and antifungal activity of saponin Mixture (**SP-mix**)

*Staphylococcus*

90 Alternative Medicine

## **7.** *Sapindus* **saponin fraction as an antidermatophytic ingredient in cosmetics**

It is difficult to use *Sapindu*s saponin fraction as a food ingredient without long-term toxicity test, because we have no history of this fraction or *Sapindus* extract as a foodstuff. Furthr‐ more, it tastes very bitter, changing the taste of foods. On the other hand, the extract has been used as a folk detergent,and is listed in the Japanese Cosmeic Ingredient Codex (JCIC), being authorized as an ingredient in cosmetics by the Ministry of Health and Welfare in Ja‐ pan. We reconfirmed the safety of the saponin fraction by dermal toxicity tests. It did not show primary dermal irritant, sentitization, phototoxicity or photosensitization effects. The present study strongly suggests that the saponins of the pericarps as an ingredient in toilet‐ ries, are valuable not only as detergents, but also for the prevention of dermatomycosis, cu‐ taneous candidiasis as well as for dandruff generation.

7

## **8. Mohave Yucca (Yucca schidigera)**

*Yucca* species (Agavaceae), grows widely in North and Central America. Mohave yucca, *Y. schidigera*, has been used as a foodstuff and folk medicine by Native Americans as well as early California settlers to treat a variety of ailments including arthritis and inflammation [3], and is approved for use in food and beverages by the U.S. Food and Drug Administra‐ tion (FDA) under Title 21 CFR 172.510, FEMA number 3121. Yucca products are currently used in a number of applications. Yucca powder and yucca extract are used as animal feed additives, as in reference [19]. Other applications include the use of the extract of this plant is now utilized as a long-lasting foaming agent in carbonated beverages, root beer, regular and low-alcohol beers, and in shampoos and foaming cosmetics. Recently, the potential of biological activities of saponins and phenolics from this plant was reviewed [20].

**S.c.a C.a. b H.a. c P.a. d K.a. e D.h. f**

Application of Saponin-Containing Plants in Foods and Cosmetics

http://dx.doi.org/10.5772/53333

93

 3.13 6.25 3.13 3.13 12.5 6.25 12.5 12.5 3.13 3.13 >100 >100 12.5 12.5 6.25 3.13 >100 >100 >100 >100 >100 >100 >100 >100 100 100 >100 100 >100 >100 >100 >100 >100 >100 >100 >100 6.25 50 3.13 3.13 >100 6.25 25 >100 3.13 3.13 >100 50 6.25 >100 3.13 12.5 >100 6.25 12.5 25 3.13 6.25 50 6.25 12.5 12.5 6.25 3.13 >100 >100 100 >100 100 >100 >100 >100 100 >100 >100 >100 >100 100 >100 >100 >100 100 >100 >100

*<sup>a</sup> Saccharomyces cerevisiae, <sup>b</sup> Candid albicans, cHansenula anomala, <sup>d</sup> Pichia nakazawae, <sup>e</sup> Kloeckera apiculata, <sup>f</sup>*Debaryo‐

**Gram-positive bacteria, MIC (μg/ml)**

*aureus* IFO 3060 1,000 *plantarum* IFO 3070 >1,000 *epidermidis* IID 866 >1,000 *rhamnosus* IFO 12521 >1,000 *Bacillus Enterococcus faecalis* IFO 3971 >1,000 *subtilis* IFO 3007 1,000 *Streptococcus mutans* IFO 13955 >1,000

**Gram-negative bacteria, MIC (μg/ml)**

*Alcaligenes faecalis* IFO 13111 1,000 *aeruginosa* JCM 2776 >1,000 *Proteus vulgaris* IFO 3851 1,000 *fluorescens* JCM 2779 >1,000

*Staphylococcus Bacillus circulans* IFO 3329 >1,000

*aureus* IID 671 1,000 *Lactobacillus*

*Escherichia coli* HUT 215 >1,000 *Pseudomonas*

*myces hansenii*

**Table 5.** Antiyeast activity of *Yucca schidigera* saponins

*licheniformis* IFO 12200 1,000

*Klebsiella pneumoniae* IFO14940 1,000

**Table 6.** Antibacterial acrivity of yucca saponin fraction

## **9. Antiyeast and antifungal spirostanoid saponins from Mohave yucca**

The presence of steroidal saponins in this plant has been reported previously [21,22]. As to the saponin constituents of this plant, a monodesmoside named YS-1 is isolated and identi‐ fied as in [23]. We have conducted the isolation and identification of individual saponins that had not been achieved prior to this study [24,25].

The EtOH extract of this plant was subjected to colomn chromatography on highly porous polymer, Diaion HP-20, which is styrene-divinylbenzene polymer. After successive elution with water and 60% and 80% MeOH, a saponin fraction which showed significant antiyeast activity against *Saccharomyces cerevisiae* was obtained by elution with 90% MeOH. This frac‐ tion was subjected to successive chromatography on silica gel and then octadesysilylated silica gel (ODS) and was finaly separated by HPLC on ODS to give fourteen yucca saponins 25-38.

Figure 3 shows the structure of all of these saponins and their sapogenins. The antiyeast ac‐ tivities of each saponin from *Y. schidigera* against six kinds of yeast, *Saccharomyces cerevisiae* (brewers yeast), *Candida albicans* (a pathogenic yeast) and *Hansenula anomala*, *Pichia nakaza‐ wae*, *Kloeckera apiculata* and *Debaryomyces hansenii* (food-deteriorating yeasts) were deter‐ mined and are summarized in Table 5.

Those saponins having a branched-chain trisaccharide moiety without any oxygen function‐ alities at C-2 and –12 exhibited potent antiyeast activities, while saponins with 2β-hydroxyl (5,6,13, and 14) or 12-keto (4 and 12) groups showed very weak or no activity. A saponin (11) with a disaccharide moiety exhibited relatively low activities. The aglycons showed no antiyeast activity.

## **10. Antimicrobial activity of the saponin fraction**

For the commercial utilization of Mohave yucca, the antimicrobial activity of the saponin fraction which was obtained by column chromatography of the extract on Diaion HP-20 (*vide supra*) was investigated. It showed no or only weak growth inhibition against both Gram-positive and Gram-negative bacteria (Table 6).

#### Application of Saponin-Containing Plants in Foods and Cosmetics http://dx.doi.org/10.5772/53333 93


*<sup>a</sup> Saccharomyces cerevisiae, <sup>b</sup> Candid albicans, cHansenula anomala, <sup>d</sup> Pichia nakazawae, <sup>e</sup> Kloeckera apiculata, <sup>f</sup>*Debaryo‐ *myces hansenii*

#### **Table 5.** Antiyeast activity of *Yucca schidigera* saponins

tion (FDA) under Title 21 CFR 172.510, FEMA number 3121. Yucca products are currently used in a number of applications. Yucca powder and yucca extract are used as animal feed additives, as in reference [19]. Other applications include the use of the extract of this plant is now utilized as a long-lasting foaming agent in carbonated beverages, root beer, regular and low-alcohol beers, and in shampoos and foaming cosmetics. Recently, the potential of

biological activities of saponins and phenolics from this plant was reviewed [20].

that had not been achieved prior to this study [24,25].

mined and are summarized in Table 5.

**10. Antimicrobial activity of the saponin fraction**

Gram-positive and Gram-negative bacteria (Table 6).

25-38.

92 Alternative Medicine

antiyeast activity.

**9. Antiyeast and antifungal spirostanoid saponins from Mohave yucca**

The presence of steroidal saponins in this plant has been reported previously [21,22]. As to the saponin constituents of this plant, a monodesmoside named YS-1 is isolated and identi‐ fied as in [23]. We have conducted the isolation and identification of individual saponins

The EtOH extract of this plant was subjected to colomn chromatography on highly porous polymer, Diaion HP-20, which is styrene-divinylbenzene polymer. After successive elution with water and 60% and 80% MeOH, a saponin fraction which showed significant antiyeast activity against *Saccharomyces cerevisiae* was obtained by elution with 90% MeOH. This frac‐ tion was subjected to successive chromatography on silica gel and then octadesysilylated silica gel (ODS) and was finaly separated by HPLC on ODS to give fourteen yucca saponins

Figure 3 shows the structure of all of these saponins and their sapogenins. The antiyeast ac‐ tivities of each saponin from *Y. schidigera* against six kinds of yeast, *Saccharomyces cerevisiae* (brewers yeast), *Candida albicans* (a pathogenic yeast) and *Hansenula anomala*, *Pichia nakaza‐ wae*, *Kloeckera apiculata* and *Debaryomyces hansenii* (food-deteriorating yeasts) were deter‐

Those saponins having a branched-chain trisaccharide moiety without any oxygen function‐ alities at C-2 and –12 exhibited potent antiyeast activities, while saponins with 2β-hydroxyl (5,6,13, and 14) or 12-keto (4 and 12) groups showed very weak or no activity. A saponin (11) with a disaccharide moiety exhibited relatively low activities. The aglycons showed no

For the commercial utilization of Mohave yucca, the antimicrobial activity of the saponin fraction which was obtained by column chromatography of the extract on Diaion HP-20 (*vide supra*) was investigated. It showed no or only weak growth inhibition against both


**Table 6.** Antibacterial acrivity of yucca saponin fraction


The antiyeast and antifungal activities are summarized in Table 7. The saponin fraction ex‐ hibited potent antiyeast activity. Infection of boiled rice such as "sushi" and "musubi" with *Hansenula anomala* and *Kloeckera apiculata* results in odor smelling like an organic solvent. In‐ fection of cooked beans and processed fish meat with *Candida famata* and *Pichia carsonii* caus‐ es oders smelling like kerosene. *Pichia nakazawae, Debaryomyces hansenii* and *Zygosaccharomyces rouxii* are film-forming yeasts, damaging "soy sauce" and "miso", oriental fermented seasonings. The saponin fraction exhibited strong growth inhibition against these

Application of Saponin-Containing Plants in Foods and Cosmetics

http://dx.doi.org/10.5772/53333

95

The saponin fraction showed less activity against common fungi, while it significantly inhib‐

Potassium sorbate has been utilized in foods as a preservative. Its antiyeast activity depends upon pH. Between pH 5.0 – 3.0, potassium sorbate completely inhibited the growth of yeast at the concentration of 0.05%, while at less acidic pH (near neutral), the activity decreased remarkably. In contrast to this, such pH dependence was not observed for the yucca saponin fraction. In the range of pH 6.3 – 3.0, it entirely inhibited the growth of yeasts at the concen‐

**11. Effects of several culture conditions against antimicrobial activity of**

The inhibitory effects of yucca extract on the growth of the yeasts isolated from ume-zuke, a salted Japanese apricot fruit product were investigated with (2% or 5%) or without sodium chloride (Table 8). From the results of MICs of yucca extract without sodium chloride, the genera *Debaryomyces, Kloeckera, Pichia, Saccharomyces* and *Zygosaccharomyces* are sensitive to yucca extract, while the genera *Cryptococcus, Rhodotorula* and *Sporobolomyces* are tolerate to yucca extract. For the difference between these yeasts, latter yeast belong anamorphic basi‐

The inhibitory effect was enhanced and showed a broad antiyeast spectrum when yucca ex‐

Table 9 shows the effects of several cultural conditions against antiyeast activity of yucca extract. The antiyeast activity of yucca extract was strengthened under the condition of chemical and physical conditions, low pH, alcohol, heating and high OP. While the highpolymer substances, such as polysaccharides and protein reduced antiyeast activity of yucca extract. It is interested that antiyeast activity of yucca extract was inhibited by free unsaturated fatty acids, palmitoleic acid, oleic acid and linoleic acid. On the other hand, saturated fatty acids, palmitic acid and stearic acid and oils composed of unsaturated fat‐ ty acids, olive oil, soybean oil and egg lecithin had no effect on the antiyeast activity of

food-deteriorating yeasts.

tration of 0.03%.

**yucca extract**

diomycetous genera.

yucca extract.

ited the growth of dermatophytic yeast and fungi.

tract was used in combination with sodium chloride.

**Table 7.** Antiyeast and antifungal acrivity of yucca saponin fraction

The antiyeast and antifungal activities are summarized in Table 7. The saponin fraction ex‐ hibited potent antiyeast activity. Infection of boiled rice such as "sushi" and "musubi" with *Hansenula anomala* and *Kloeckera apiculata* results in odor smelling like an organic solvent. In‐ fection of cooked beans and processed fish meat with *Candida famata* and *Pichia carsonii* caus‐ es oders smelling like kerosene. *Pichia nakazawae, Debaryomyces hansenii* and *Zygosaccharomyces rouxii* are film-forming yeasts, damaging "soy sauce" and "miso", oriental fermented seasonings. The saponin fraction exhibited strong growth inhibition against these food-deteriorating yeasts.

**Yeast, MIC (μg/ml)** *Saccharomyces Kloeckera apiculata* IFO 154 62.5

<sup>5</sup> *Debaryomyces*

<sup>3</sup> *Zygosacharomyces*

*laurentii* IFO 609 125 *rouxii* IFO 845 31.3 *Pichia rouxii* IFO 1130 31.3

**Fungi, MIC (μg/ml)**

*niger* IFO 4343 >1,000 *awamoi* HUT 2014 >1,000 *oryzae* HUT 2065 >1,000 *awamoi* HUT 2015 >1,000 *oryzae* HUT 2175 125 *Mucor pusillus* HUT 1185 15.6

*oryzae* HUT 2192 >1,000 *formosaensis* IFO 4756 >1,000 *sydowii* HUT 4097 >1,000 *nigricans* IFO 4731 >1,000

**Dermatophytic yeast and fungi, MIC (μg/ml)** *Tricophyton Sabouraudites canis* IFO 7863 31.3

15.

31. 3

*hanenii* IFO 18 31.3

*hanenii* IFO 27 62.5

*hanenii* IFO 47 31.3

*hanenii* IFO 7011 125

*Candida famata* IFO 664 31.3

*Penicillium expansum* IFO 5453 >1,000

*Candida albicans* TIMM 0134 62.5

<sup>6</sup> *Epidermophyton floccosum* IFO 9045 31.3

62.

31. 3

62. 5

31. 3

31. 3

31.

31. 3

31. 3

*Aspergillus Aspergillus*

*oryzae* HUT 2188 >1,000 *Rhizopus*

*cerevisiae* IMO 293

*cerevisiae* HUT 2075

*cerevisiae* JCM 2223

*anomala* HUT 7083

*nalazawae* HUT 1688

*carsonii* IFO 946

*rubrum* IFO 5807

*mentagrophytes* IFO 5809

\* food deteriorating yeast \*\* film-forming yeast in soy sauce

**Table 7.** Antiyeast and antifungal acrivity of yucca saponin fraction

*Hansenulla* sp.

94 Alternative Medicine

*Cryptococcus sp.*

The saponin fraction showed less activity against common fungi, while it significantly inhib‐ ited the growth of dermatophytic yeast and fungi.

Potassium sorbate has been utilized in foods as a preservative. Its antiyeast activity depends upon pH. Between pH 5.0 – 3.0, potassium sorbate completely inhibited the growth of yeast at the concentration of 0.05%, while at less acidic pH (near neutral), the activity decreased remarkably. In contrast to this, such pH dependence was not observed for the yucca saponin fraction. In the range of pH 6.3 – 3.0, it entirely inhibited the growth of yeasts at the concen‐ tration of 0.03%.

## **11. Effects of several culture conditions against antimicrobial activity of yucca extract**

The inhibitory effects of yucca extract on the growth of the yeasts isolated from ume-zuke, a salted Japanese apricot fruit product were investigated with (2% or 5%) or without sodium chloride (Table 8). From the results of MICs of yucca extract without sodium chloride, the genera *Debaryomyces, Kloeckera, Pichia, Saccharomyces* and *Zygosaccharomyces* are sensitive to yucca extract, while the genera *Cryptococcus, Rhodotorula* and *Sporobolomyces* are tolerate to yucca extract. For the difference between these yeasts, latter yeast belong anamorphic basi‐ diomycetous genera.

The inhibitory effect was enhanced and showed a broad antiyeast spectrum when yucca ex‐ tract was used in combination with sodium chloride.

Table 9 shows the effects of several cultural conditions against antiyeast activity of yucca extract. The antiyeast activity of yucca extract was strengthened under the condition of chemical and physical conditions, low pH, alcohol, heating and high OP. While the highpolymer substances, such as polysaccharides and protein reduced antiyeast activity of yucca extract. It is interested that antiyeast activity of yucca extract was inhibited by free unsaturated fatty acids, palmitoleic acid, oleic acid and linoleic acid. On the other hand, saturated fatty acids, palmitic acid and stearic acid and oils composed of unsaturated fat‐ ty acids, olive oil, soybean oil and egg lecithin had no effect on the antiyeast activity of yucca extract.


**Yeast**

*K. apiculata* 4631 2000 1000 62.5 *K. apiculata* 12219 2000 2000 500 *K. corticis* 217 1000 1000 NG *K. corticis* 236 2000 250 NG *K. corticis* 12828 500 250 NG *K. japonica* 12220 500 500 250 NG : No growth recognized without yucca extract

\*unsatulated fatty acid, \*\*triglycerides, \*\*\*osmotic pressure

**Table 9.** Effects of the cultural condition against antiyeast activity of yucca extract

foods and fermented seasonings is now under development [26].

activity of yucca saponin fraction

USFA\* TG\*\*

a:↑strengthen, ↓reduce, →no change

antiyeast activity

**MIC (μg/ml)**

*Kloeckera Zygosaccharomyces*

*K. apiculata* 203 1000 1000 500 *Z. bailii* 213 2000 250 NG *K. apiculata* 208 1000 500 500 *Z. rouxii* 214 500 250 250 *K. apiculata* 258 1000 1000 500 *Z. rouxii* 215 250 250 250 *K. apiculata* 266 >2000 >2000 2000 *Z. rouxii* 216 125 125 250

**Table 8.** Antiyeast activity of yucca extract against 64 yeasts isolated from foods and effect of NaCl on antiyeast

**12. Utilization of the yucca extract as an anti-food deteriorating agents**

Yucca extract is non-toxic and non-mutagenic. It is recognized as safe for human food use by U.S.FDA (listed in 21 CFR 172.510). The extract is tasteless and odourless, exerting no influ‐ ence on the taste of foods. It is readily soluble in water and stable on heating. Based on the present study, commercial application of the extract for extending the shelf life of cooked

**low pH heating alcohol polysaccharide protein lipid high**

↑<sup>a</sup> ↑ ↑ ↓ ↓ ↓ → ↑

**Yeast**

Application of Saponin-Containing Plants in Foods and Cosmetics

**NaCl NaCl 0% 2% 5% 0% 2% 5%**

**MIC (μg/ml)**

http://dx.doi.org/10.5772/53333

97

**OP\*\*\***


**Yeast**

96 Alternative Medicine

**MIC (μg/ml)**

*C. albicans* 221 1000 500 250 *P.anomala* 201 500 250 250 *C. guilliermondii* 212 >2000 1000 500 *P.anomala* 202 250 250 250 *C. guilliermondii* 213 >2000 2000 500 *P.anomala* 203 250 125 125 *C. guilliermondii* 222 1000 500 250 *P.anomala* 204 500 250 250 *C. guilliermondii* 224 1000 250 250 *P.anomala* 206 250 125 125 *C. guilliermondii* 227 >2000 >2000 2000 *P.anomala* 211 500 250 250 *C. krusei* 222 >2000 >2000 1000 *P.anomala* 216 500 250 125 *C. lipolytica* 223 62.5 62.5 62.5 *P.anomala* 219 500 250 250 *C. parapsilosis* 224 1000 500 500 *P.anomala* 223 500 250 250 *C. tropicalis* 225 >2000 >2000 1000 *P.anomala* 256 500 250 250 *C. valida* 226 1000 500 125 *P.anomala* 260 250 250 250 *C. versatilis* 228 500 250 250 *P.anomala* 261 500 250 250 *C. zeylanoides* 229 250 250 125 *P.anomala* 262 500 250 250 *Cryptococcus P.anomala* 265 500 250 250 *C. neoformans* 231 >2000 >2000 1000 *P. farinosa* 207 250 250 125

*D.hansenii* 201 1000 125 62.5 *R. rubra* 233 >2000 1000 500

*D.hansenii* 214 1000 1000 1000 *S. cerevisiae* 203 500 250 62.5 *D.hansenii* 215 1000 1000 2000 *S. cerevisiae* 208 250 250 62.5 *D.hansenii* 220 2000 2000 >2000 *S. farmentati* 209 500 250 62.5 *D.hansenii* 225 1000 2000 2000 *S. fibullgera* 211 2000 1000 1000 *D.hansenii* 263 >2000 2000 1000 *S. servazzii* 210 2000 1000 1000

*G. candidum* 218 500 125 NG *S. pombe* 212 62.5 NG NG

*Hansenula S. albo-rubescens* 234 >2000 >2000 2000

*Issatchenkia T. delbrieckii* 4188 500 125 62.5 *I. orientalis* 237 125 125 62.5 *T. delbrieckii* 4952 500 500 250

*Candida Pichia*

*Debaryomyces Rhodotorula*

*D.hansenii* 206 1000 1000 2000 *Saccharomyces*

*Geotrichum Shizosaccharomyces*

*G. capitatum* 219 2000 1000 NG *Sporobolomyces*

*H. saturnus* 202 1000 500 250 *Torulaspora*

**Yeast**

**NaCl NaCl 0% 2% 5% 0% 2% 5%**

**MIC (μg/ml)**

**Table 8.** Antiyeast activity of yucca extract against 64 yeasts isolated from foods and effect of NaCl on antiyeast activity of yucca saponin fraction


**Table 9.** Effects of the cultural condition against antiyeast activity of yucca extract

## **12. Utilization of the yucca extract as an anti-food deteriorating agents**

Yucca extract is non-toxic and non-mutagenic. It is recognized as safe for human food use by U.S.FDA (listed in 21 CFR 172.510). The extract is tasteless and odourless, exerting no influ‐ ence on the taste of foods. It is readily soluble in water and stable on heating. Based on the present study, commercial application of the extract for extending the shelf life of cooked foods and fermented seasonings is now under development [26].

Figure 4 shows the application of yucca extract to sponge cake. Addition of 0.2% of yucca extract to sponge cake had effective on the growth of fungi and yeasts stored in room for one week.

The application of yucca extract to strawberry jam was showed in Figure 5. The jam mixed 0.02% and 0.04% of yucca extract and stored in room for one week shows no change, where‐ as control jam was contaminated by fungi.

(Yucca (0.2%)) (Controll)

acceptable natural preservatives. Many plant extracts possess antimicrobial activity against a range of bacteria, yeast and fungi, but the variations in quality and quantity of their bioac‐

Application of Saponin-Containing Plants in Foods and Cosmetics

http://dx.doi.org/10.5772/53333

99

Based on the present study, mukurozi extract and yucca extract are considered to be effec‐ tive for the preservation of foods and cosmetics. Both mukurozi and yucca plants have been consumed by humans for a long time. These plants also have wide application due to little

Thus our works demonstrate that the saponin fraction from Sapindus pericarps and Mohave yucca stems can be recommended as alternative preservations for foods and cosmetics.

[1] Leung AY, Encyclopedia of Common Natural Ingredients Used in Food, Drugs and

[2] Hostettmann K, Marston, Saponins, Cambridge University Press, Cambridge, 1995

Drugs and Cosmetics, 2nd ed., John Wiley and Sons, New York, 1996

[3] Leung AY, Foster S. Encyclopedia of Common natural Ingredients Used in Food,

[4] Waller GR, Yamasaki K. Proceedings of an American Chemical Society Symposium

[5] Balandrin MF, Commercial Utilization of Plant-derived Saponins: An Overview of medicinal, Pharmaceutical and Industrial Applications, In: Waller GR and Yamasaki

[6] Oakenfull D. Saponins in the treatment of hypercholesterolemia, In: Spiller GA (ed.)

[7] Klausner A. Adjuvants: a real shot in the arm for recombinant vaccines. Bio/Technol‐

[8] Setten DC, Werken G. Molecular Structures of Saponins from *Quillaja saponaria* Moli‐ na. In: Waller GR and Yamasaki K. (eds) Saponins Used in traditional and Modern

K. (eds) Saponins Used in Food and Agriculture: Plenum Press; 1996. p1-14

Handbook of Lipids in Human Nutrition. CRC Press; 1996. p107-112

tive constituents is major disadvantage to their industrial uses.

Yukiyoshi Tamura, Masazumi Miyakoshi and Masaji Yamamoto

Cosmetics, John Wiley and Sons, New York, 1980

on Saponins: August 20-24, 1995, Chicago, Illinois

ogy 1988; 6(7), 773-777

Medicine: Plenum Press; 1996. p185-193

Maruzen Pharmaceuticals Co. Ltd.,Hiroshima, Japan

pH or food component interaction.

**Author details**

**References**

**Figure 4.** Application of yucca extract to sponge cake

**Figure 5.** Application of yucca extract to strawberry jam

### **13. Conclusion**

The microbial safety of foods and cosmetics continues to be a major concern to consumers, regulatory agencies and food industries throughout the world. Although synthetic antimi‐ crobials are approved in many countries, the recent trend has been for use of natural preser‐ vatives, which necessitates the exploration of alternative sources of safe, effective and acceptable natural preservatives. Many plant extracts possess antimicrobial activity against a range of bacteria, yeast and fungi, but the variations in quality and quantity of their bioac‐ tive constituents is major disadvantage to their industrial uses.

Based on the present study, mukurozi extract and yucca extract are considered to be effec‐ tive for the preservation of foods and cosmetics. Both mukurozi and yucca plants have been consumed by humans for a long time. These plants also have wide application due to little pH or food component interaction.

Thus our works demonstrate that the saponin fraction from Sapindus pericarps and Mohave yucca stems can be recommended as alternative preservations for foods and cosmetics.

## **Author details**

Figure 4 shows the application of yucca extract to sponge cake. Addition of 0.2% of yucca extract to sponge cake had effective on the growth of fungi and yeasts stored in room for

The application of yucca extract to strawberry jam was showed in Figure 5. The jam mixed 0.02% and 0.04% of yucca extract and stored in room for one week shows no change, where‐

(Yucca (0.2%)) (Controll)

(Controll) (Yucca 0.02%) (Yucca 0.04%)

The microbial safety of foods and cosmetics continues to be a major concern to consumers, regulatory agencies and food industries throughout the world. Although synthetic antimi‐ crobials are approved in many countries, the recent trend has been for use of natural preser‐ vatives, which necessitates the exploration of alternative sources of safe, effective and

one week.

98 Alternative Medicine

as control jam was contaminated by fungi.

**Figure 4.** Application of yucca extract to sponge cake

**Figure 5.** Application of yucca extract to strawberry jam

**13. Conclusion**

Yukiyoshi Tamura, Masazumi Miyakoshi and Masaji Yamamoto

Maruzen Pharmaceuticals Co. Ltd.,Hiroshima, Japan

## **References**


[9] Hayashi H, Sudo H. Economic importance of licorice. Plant Biotechnology 2009; 26, 101-104

[25] Miyakoshi M, Yamasaki K. et al. Antiyeast steroidal saponins from *Yucca schidigera* (Mohawa Yucca), a new anti-food deteriorating agent. Journal of Natural Products

Application of Saponin-Containing Plants in Foods and Cosmetics

http://dx.doi.org/10.5772/53333

101

[26] Otoguro C, Tamura Y. et al. Inhibitory effect of yucca extract on the growth of filmforming yeasts isolated from Ume-zuke, salted Japanese apricot fruit. Nihon Shoku‐

2000; 63(3), 332-338

hin Hozo Kagaku Kaishi. 1998; 24(1), 3-10


[25] Miyakoshi M, Yamasaki K. et al. Antiyeast steroidal saponins from *Yucca schidigera* (Mohawa Yucca), a new anti-food deteriorating agent. Journal of Natural Products 2000; 63(3), 332-338

[9] Hayashi H, Sudo H. Economic importance of licorice. Plant Biotechnology 2009; 26,

[10] Kimata H, Tanaka O. et al. Saponins of pericarps of *Sapindus mukurossi* Gaertn. and solubilization of monodesmosides by bisdesmosides. Chemical Pharmaceutical Bul‐

[11] Mizutani K, Tanaka O. et al. Saponins from *Anemone rivularis*. Planta Medica 1984;

[12] Ishii H, Yoshimura Y. et al. Isolation, characterization and nuclear magnetic response spectra of new saponins from the roots of *Bupleurum falcatum* L. Chemical Pharma‐

[13] Kimata H, Tanaka O. et al. Saponins of Juk-Siho and roots of *Bupleurum longeradiatum*

[14] Shao CJ, Tanaka O. et al. Saponins from roots of *Kalopanax septemlobus* (Thunb.) Koidz., Ciqui: Structure of kalopanax-saponin C, D, E and F. Chemical Pharmaceuti‐

[15] Kizu H, Namba T. et al. Studies on Nepalese crude drugs. III. On the saponins of *Hedera nepalensis* K. Koch. Chemical Pharmaceutical Bulletin 1985; 33(8), 3324-3329 [16] Mizui F, Tanaka O. et al. Saponins from brans of quinoa, *Chenopodium quinoa* Willd. I.

[17] Nie R, Tanaka O. et al. A triterpenoid saponin from *Thladiantha hookeri* var. *pentadac‐*

[18] Fujita M, Tanaka O. et al. The study on the constituents of *Clematis* and *Akebia* spp. II. On the saponins isolated from the stem of *Akebia quinata* Decne. (1). Yakugaku Zasshi

[19] Cheeke PR, Biological Effects of Feed and Forage Saponins. In: Waller GR and Yama‐ saki K. (eds) Saponins Used in Food and Agriculture: Plenum Press; 1996. p377-385 [20] Cheeke PR, Oleszek W. Anti-inflammatory and anti-arthritis effects of Yucca schidi‐

[21] Wall ME, Eddy CR. Steroidal sapogenins, Journal of Biological Chemistry 1952;

[22] Kaneda N, Staba JE. et al. Steroidal constituents of *Yucca schidigera* plants and tissue

[23] Kameoka H, Miyazawa M. 65th Spring National Meeting of the Chemical Society of

[24] Tanaka O, Tamura Y. et al. Application of saponins in foods and cosmetics: Saponins of Mohave yucca and *Sapindus mukurossi*. In: Waller GR and Yamasaki K. (eds) Sapo‐

nins Used in Food and Agriculture: Plenum Press; 1996. p1-11

Turcz. Chemical Pharmaceutical Bulletin 1982; 30(12), 4373-4377

Chemical Pharmaceutical Bulletin 1988; 36(4), 1415-1418

*tyla*. Phytochemistry 1989; 28(6), 1711-1715

gera: reviw. Journal of Inflammatory 2006;3:6.

cultures. Phytochemistry 1987; 26(5), 1425-1429

Japan 1993; 28-31 March, Tokyo, Japan 1993

101-104

100 Alternative Medicine

50(4), 327-331

letin 1983; 31(6), 1998-2005

ceutical Bulletin 1980; 28(8), 2367-2383

cal Bulletin 1989; 37(2), 311-314

1974; 94(2), 194-198

198(2), 533-543

[26] Otoguro C, Tamura Y. et al. Inhibitory effect of yucca extract on the growth of filmforming yeasts isolated from Ume-zuke, salted Japanese apricot fruit. Nihon Shoku‐ hin Hozo Kagaku Kaishi. 1998; 24(1), 3-10

**Section 3**

**Therapeutic Potential**
