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Prostanoic Acid Synthesis Essay

Names
IUPAC name
7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid
Identifiers
ChEBI
ChemSpider
  • InChI=1S/C20H38O2/c1-2-3-4-5-6-9-13-18-15-12-16-19(18)14-10-7-8-11-17-20(21)22/h18-19H,2-17H2,1H3,(H,21,22)/t18-,19-/m0/s1
    Key: WGJJROVFWIXTPA-OALUTQOASA-N
  • CCCCCCCCC1CCCC1CCCCCCC(=O)O
Properties
C20H38O2
Molar mass310.52 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Prostanoic acid (7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid) is a saturated fatty acid which contains a cyclopentane ring. Its derivatives are prostaglandins - physiologically active lipid substances. Prostanoic acid is not found in nature, but it can be synthesized in vitro.

Synthesis[edit]

For the first time the synthesis of prostanoic acid from 1-formylcyclopentene was considered in detail in the scientific literature in 1975 by a group of French pharmacists.[1] One year later, a group of Japanese scientists, who worked in the central research laboratory of the "Sankyo Co., Ltd." company (Shinagawa, Tokyo), published another method for obtaining prostanoic acid from 2-[4-hydroxy-5-(methoxymethyl)cyclopent-2-en-1-yl] acetic acid.[2] In 1986, a group of Japanese scientists from Kyushu University in Fukuoka proposed their own scheme for obtaining prostanoic acid from limonene.[3]

See also[edit]

References[edit]

1. Introduction

At the present time, ~60% of approved cancer treatment drugs are of natural origin [1,2,3]. Natural products that exist in marine animals and plants function as anti-mutagenic and anti-carcinogenic and may inhibit one or more stages of carcinogenesis by preventing or delaying cancer development [4]. An estimated 14,000 pharmacologically active compounds have been isolated from marine plants and animals, suggesting an existence of immense diversity within this environment. The marine environment is therefore a rich source for discovering novel lead compounds for the development of new anti-cancer drugs [5,6] and cancer-preventive nutraceuticals. A comprehensive survey of pharmacologic activity was conducted over a period of 15 years by the U.S. National Cancer Institute and found that 4% of the marine species (mainly animals) examined contained anti-tumor compounds. Potential sources of new types of biologically active compounds isolated from marine echinoderms are being applied in biomedical field.

In recent years, attention has been devoted to developing bioactive agents from natural food sources to produce pharmaceutical grade anti-inflammatory supplements. Sea cucumbers are nutrient-rich, invertebrate deep-sea dwellers that have been used for centuries as an anti-inflammatory and anti-disease food source and for treating ailments in Korea, Japan, Indonesia, and China [7,8,9]. Sea cucumbers are usually soft-bodied echinoderms, looking like a cucumber, and they are a diverse group of flexible, elongated, worm-like organisms, with a leathery skin and gelatinous body. Habitually, they tend to live on the sea floor in deep seas. Sea cucumbers are reported in Chinese and Malaysian literature as they are recognized as a tonic and traditional remedy for various diseases. The export and consumption of bioactive components extracted from marine sea cucumbers has increased in western markets as these components become available in supplements for various diseases [10,11,12,13,14,15]. Hence, a comprehensive approach to utilizing biologically active agents derived from natural foods for wellness and towards disease prevention and treatment is necessary.

Sea cucumbers consist of vitamins, minerals, cerebrocides, peptides, and lectins, and also contain unique molecules, such as sulfated polysaccharides, 12-methyltetradecanoic acid (12-MTA), philinopside E, triterpene glycoside compounds, glycosaminoglycan, and chondroitin sulfates [16,17,18,19,20,21,22,23,24,25,26,27]. In sufficient quantities, these unique compounds are known to possess anti-microbial, anti-oxidant, anti-angiogenic, anti-inflammatory, immunomodulatory, and anti-tumoral properties [28,29,30,31] (Figure 1). As supplements, these sea cucumber extracts have been shown to suppress inflammation and increase innate immune responses. In this review, we will discuss the anti-inflammatory, anti-tumorigenic, and immune properties of bioactive agents extracted from sea cucumbers.

Figure 1. Bioactive components of sea cucumber extracts and their biological effects on various human cancer cells and cancer animal models.

Figure 1. Bioactive components of sea cucumber extracts and their biological effects on various human cancer cells and cancer animal models.

3. Immunostimulatory and Anti-Tumor Functions of Sea Cucumber Extracts

A complex of monosulfated cucumariosides with cholesterol isolated from Cucumaria japonica demonstrated immunomodulatory properties in C57Bl6 mice (Figure 2). When administered in low doses, this complex displayed more than twofold stimulation of lysosomal activity on mouse macrophages (Figure 3). In addition, this complex significantly increased the animals’ resistance against bacterial infections elicited by Y. pseudotuberculosis or S. aureus. Furthermore, it increased phagocytosis and ROS formation, and stimulation of IL6 and TNF-α production was observed in lymphocytes [47].

Frondoside A is a monosulfated pentaoside, a component of the glycoside fraction isolated from Cucumaria Frondosa, and is reported to possess immunomodulatory properties when administered in subtoxic doses. A 0.2-μg dose of Frondoside A administered intra-peritoneally (i.p.) to Balb C mice increased lysosomal activity in macrophages in treated animals compared with vehicle-treated controls (Figure 3). Frondoside A increased cell-based immunity in these experiments; this immunity is an important feature for any preventive agent to improve the innate immune responses or in cases in which the host’s immune responses are hampered by cytotoxic agents against the antigen or tumor growth [48] (Figure 2). A triterpene glycoside isolated from Cucumaria japonica, cucumarioside A2-2, showed twofold increased stimulation of lysosomal activity and acted as a Ca2+ agonist in mouse macrophages [49] (Figure 3). Another report suggested similar increased immunostimulatory properties of triterpene glycosides from C. japonica, in which an increase in macrophage lysosomal activity was observed [50] (Figure 2 and Figure 3).

Triterpene glycosides isolated from sea cucumbers (Mensamaria intercedens) were evaluated for their anti-tumorigenic properties in a mouse model of S180 sarcoma and mouse Lewis lung cancer cell lines [51]. A hot water extract of sea cucumber (Stichopus japonicus) was reported to significantly inhibit proliferation and produce concentration-dependent cytotoxicity in human colon cancer Caco-2 cells [52]. Isolated sphingoid bases of sea cucumber (Stichopus variegatus) showed profound cytotoxic effects and decreased cell viability, and induced apoptosis via caspase 3 activity in DLD-1, WiDr, and Caco-2 human colon cancer cells (Figure 2). These in vitro studies of human colon cancer cells suggest that glycosides extracted from sea cucumbers may be good anti-tumor agents for the prevention and treatment of human colon cancer (Table 1).

Table 1. Sea cucumber extracts and their effects on various cancers in in vitro and in vivo models.

CompoundSea cucumberEffectsType of cancerRefs.
Triterpene glycosidesMensamaria intercedensAnti-tumorigenicmouse model of S180 sarcoma and mouse Lewis lung cancer cell lines[51]
Hot water extractStichopus japonicasAnti-proliferation cytotoxicHuman colon cancer CaCo2 cells[52]
Organic extractsHolothuria leucospilota, Holothuria scabra, Stichopus chloronotusAnti-proliferationhuman A549 non-small lung cancer cells and C33A cervical cancer cells[29]
sulfated triterpene glycosidesPearsonothuria graeffei

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