Organic Chemistry I

PresentationBy Daniel. I. Egbe

Instructor: Professor Wan Jin Jhang

Outline

• Brief introduction about my molecule (properties of saponin).

• Significance of the molecule.

• How is saponin different from other molecules of same kind?

• Hypothesis and aim.

• The synthesis of saponin/Mechanism

Saponin.

• The word saponin comes from a Greek word called sapona, which means soap.

• Saponins are a group of glycosides that can be obtained from many plant species like onion, beans, garlic, and many other plants.

• There are several types of Saponins but generally, they can be divided into ginseng saponin which contains 24 types of saponin and red ginseng saponin which contains 32 types of saponin.

structure

properties

Molecular Weight: 414.6231

Molecular Formula: C27H42O3

Physical State:

Solid

Solubility:

Soluble in water, ethanol, and methanol.

Storage: Store at room temperature

Melting Point:

158 °C

Density: 0.5 g/cm3 at 20 °C

So how significant is saponin to us?Saponins are very important compounds required in the body. In the body, they perform the

following.

Breaks down fat well, accelerates nutrient absorption and digestion;

Anti-inflammatory, antioxidant, and anti-cancer effects*****

Helps erectile dysfunction;

Revitalizes enzymes within cells and improves metabolism;

Stimulates activity of the enzyme involved in the process of bone building and repair, and increase calcium deposition by bone marrow stem cells;

Improves arterial flexibility significantly and decreases blood pressure;

What really makes saponin different from other drugs used in the treatment of cancer????

Saponin obtained from plants is more advantageous than the others because it is flexible. It is very effective and efficient in the body. It is less toxic and has very little side effects.

Hypothesis

The solution to the disastrous cancer problems we have in our societies todays revolves just around us, in the saponin produced from plant classes like Caryophyllaceae (Saponaria vaccaria)

The Plant

Aims

Extracting triterpenoid saponin from higher plants like oats.

Using triterpenoid saponin from plants to fight against cancer in the body.

Synthesis of Saponin

• The first step in the pathway is the cyclization of 2,3-oxidosqualene by β- amyrin synthase (BAS).

• Then the other steps that follow include:

oxidation of β- amyrin at positions 16, 23, and/or 28;

glycosylation at position 28 and, for the major bisdesmosides, position 3;

the acylation of sugars with acetyl and 2-hydroxy-2-methylglutaryl moieties.

Anti-cancer Effects of Saponin

Several studies have shown that saponins protect against cancer through different mechanisms which include: antioxidant effect, direct and select cytotoxicity of cancer cells, immune modulation and the regulation of cell proliferation.

mechanism 

• In the development of cancer, the COX-2/PGE2 signaling pathway plays a very significant role.

• COX-2 (cyclooxygenase 2), is an enzyme that catalyses the first step in the synthesis of prostanoids from arachidonic acid and is involved in inflammatory diseases and carcinogenesis.

• In tumors, COX-2 is upregulated and promotes the release of the pro-inflammatory mediator prostaglandin E2 (PGE2), which is tumor development and progression to act on its cell surface G protein-coupled receptors.

• The saponins downregulate the COX-2 and also induce apoptosis on several cancer cell lines.

References• Han, L.-T., Fang, Y., Li, M.-M., Yang, H.-B., & Huang., a. F. (2013). The

Antitumor Effects of Triterpenoid Saponins from the Anemone flaccida and the Underlying Mechanism. (S. Anant, Ed.) Evidence-Based Complementary and Alternative Medicine, 1-9.

• Kaskiw, M. J., Tassotto, M. L., Moka, M., Tokar, S. L., Pycko, R., Th’ng, J., & Jiang., &. Z.-H. (2009). Structural analogues of diosgenyl saponins: Synthesis and anticancer activity. Bioorganic & Medicinal Chemistry, 1-10. Retrieved from www.elsevier.com/locate/bmc

• Meesapyodsuk, D., Balsevich, J., Reed, D. W., & Covello, a. P. (2007). Saponin Biosynthesis in Saponaria vaccaria. cDNAs Encoding b-Amyrin Synthase and a Triterpene Carboxylic. Plant Physiology, 143, 959-969. Retrieved from www.plantphysiol.org/cgi/doi/10.1104/pp.106.088484