Total phenols, antioxidant activity expressed as DPPH radical scavenging activity of
Abstract
Smilax (Smilacaceae) is a genus of about 350 species, found in temperate, tropical and subtropical zones worldwide. The plants belonging to this genus are found throughout Asia, Europe, Oceania and the Americas. Species of the genus Smilax commonly called sarsaparilla are characterized as climbers, with long, thin thorny stem. The branches have tendrils which attach to other plants or objects and grow steadily upward. The roots of these plants have been used for centuries in Asia and the Americas as a tonic, diuretic and sudorific. The rhizome, roots, stems and leaves of sarsaparilla are used in traditional medicine. In the scientific literature, there are several reports on immunomodulatory properties, anticonvulsant, antibacterial, antifungal, anticancer, antidiabetic and antioxidant properties. However, there are no reports which explain the antioxidant activity of sarsaparilla extracts as a function of phenolic compound structures, such as flavonoids and phenylpropanoids. In this chapter, the relevance of phenolic chemical structure in antioxidant and anticancer activity of sarsaparilla extracts will be described. Special emphasis is placed on phenylpropanoid glycosides that consist of a sucrose core. These compounds are evidence of chemotaxonomy in the genus Smilax.
Keywords
- Smilax
- phenolic compounds
- antioxidant activity
- anticancer activity
- phenylpropanoids
- flavonoids
1. Introduction
The genus
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F1.png)
Figure 1.
(A)
The rhizome, roots, stems and, occasionally, leaves of sarsaparilla are used as food and in traditional medicine. These plants are known to have immunomodulatory, antioxidant, antibacterial, antifungal and diuretic properties. Additionally, they are used for relief from climatery [1]. Also, the genus
In recent years, interest in the study of the genus
There are reports about the antioxidant property expressed as DPPH• radical scavenging activity of species of the genus
Therefore, this review will describe
2. Genus Smilax
The review is organized by species, and the principal uses in traditional medicine for every species discussed are described. The methods of extraction and purification of phenolic compounds are briefly mentioned. Also, the methods used to evaluate antioxidant and anticancer activities are discussed. Various reports make evident the diversity of the chemical structure of phenolic compounds and their relation to corresponding biological properties
2.1. Smilax aspera
Longo
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F2.png)
Figure 2.
Anthocyanin glycosides isolated from
2.2. Smilax bockii
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F3.png)
Figure 3.
Four flavonols (three aglycones and one glucoside), three flavanones (one aglycone and two glycosides) and one phenylpropanoid ester isolated from
2.3. Smilax bracteata
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F4.png)
Figure 4.
Two flavan-3-ol glycosides and one stilbene isolated from
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F5.png)
Figure 5.
Phenylpropanoid glycosides with a sucrose core isolated from
In a later study, Zhang
2.4. S. campestris
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F6.png)
Figure 6.
Chemical structure of rutin, a flavonol glycoside isolated from
2.5. Smilax china
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F7.png)
Figure 7.
Two flavan-3-ol aglycones isolated from
Kuo
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F8.png)
Figure 8.
Phenylpropanoid glycosides with a sucrose core (five smilasides, two helionoside and one smiglaside) isolated from
Li
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F9.png)
Figure 9.
One flavanonol (
2.6. Smilax corbularia
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F10.png)
Figure 10.
Flavononol rhamnosides (
2.7. Smilax domingensis
2.8. Smilax excelsa
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F11.png)
Figure 11.
Two phenylpropanoids (
2.9. Smilax fluminensis
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F12.png)
Figure 12.
Flavonol glycoside (
2.10. Smilax glabra
The second most-studied species, after
Xia
Trinh
Zhang
Moreover, there have been several chemical studies to isolate and characterize phenolic compounds from different parts of
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F13.png)
Figure 13.
Flavonoids and smiglasides isolated from
Xu
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F14.png)
Figure 14.
Flavonoids and phenylpropanoids isolated from
2.11. Smilax glycyphylla
Huang
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F15.png)
Figure 15.
Phenolic compounds isolated from 80% ethanol extract of
2.12. Smilax lanceaefolia
The root of
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F16.png)
Figure 16.
Flavanonol glycoside from methanol extract of
2.13. Smilax riparia
The roots and rhizomes of
Wang
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F17.png)
Figure 17.
Phenylpropanoids from 95% ethanol extract of
2.14. Smilax scobinicaulis
The roots of
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F18.png)
Figure 18.
Flavones from 95% ethanol extract of
2.15. Smilax sebeana
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F19.png)
Figure 19.
Phenolic compounds from methanol extract of
2.16. Smilax trinervula
![](http://cdnintech.com/media/chapter/53603/1512345123/media/F20.png)
Figure 20.
Two neolignans (
3. Conclusions
The polar extracts of
Specie (part of plant) Extract/fraction |
Total phenols (mg GAE/g dm) | DPPH●
Radical scavenging activity IC50 (μg/mL) |
---|---|---|
|
Ref. [17] | |
Ethanol extract | – | 13.6 |
Hexane fraction | – | 405.5 |
Dichloromethane fraction | – | 298.9 |
Ethyl acetate fraction | – | 108.9 |
Butanol fraction | – | 2.1 |
|
Ref. [19] | Ref. [19] |
Methanol extract | – | – |
Chloroform fraction | 142.6 | 302.2 |
Ethyl acetate fraction | 401.6 | 85.5 |
Butanol fraction | 206.8 | 210.9 |
Water fraction | 97.3 | 224.9 |
|
Ref. [29] | Ref. [29] |
Water extract | 30.6 | 1190 |
Infusion | 35.7 | 1240 |
Ethanol extract | 30.1 | 1490 |
Ethyl acetate extract | 8.8 | 2660 |
|
Ref. [44] | Ref. [44] |
Water extract | 29.41 | 236 |
Ethanol fraction a | 109.8 | 58 |
Methanol extract | 152.3 | 43 |
|
Ref. [55] | |
95% ethanol extract | – | 2520 |
95% ethanol fraction | – | 1460 |
Ethyl acetate fraction | – | 1330 |
Methanol fraction | – | 1000 |
Table 1.
This fraction was obtained from water extract.
GAE mg: milligrams of gallic acid equivalent, dm: dry matter, IC50: extract concentration necessary to decrease 50% the initial concentration of DPPH•. The fractions were obtained from a partition of corresponding extract.
Acknowledgments
The authors thank Carol Ann Hayenga for her English assistance in the preparation of this manuscript. Support was provided by the Universidad Tecnológica de la Mixteca.
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