Chlorophyllin

Chlorophyllin
Structural formula of chlorophyllin, sodium salt
Space-filling model of the chlorophyllin molecule, sodium salt
Names
Other names
Natural green 3, E141
Identifiers
11006-34-1 Yes
ChemSpider 4586363 Yes
Jmol-3D images Image
Image
PubChem 5479494
UNII 1D276TYV9O Yes
Properties
C34H31CuN4Na3O6
Molar mass 724.15 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Chlorophyllin refers to any one of a group of closely related water-soluble salts that are semi-synthetic derivatives of chlorophyll, differing in the identity of the cations associated with the anion. Its most common form is a sodium/copper derivative used as a food additive and in alternative medicine. Chlorophyll is present in green leafy vegetables and reaching levels as high as 5.7% in spinach.[1] As a food coloring agent, copper complex chlorophyllin is known as natural green 3 and has the E number E141.[2]

Uses

Cancer prevention

Because chlorophyll does not dissolve in water, food sources of chlorophyll do not bind to mutagenic substances to a significant extent. Chlorophyllin, being water-soluble, can significantly bind to environmental mutagens such as the polycyclic aromatic hydrocarbons benzo[a]pyrene[3] and dibenzo{a,i}pyrene.[1] Chlorophyllin binds to mutagens twenty times better than resveratrol and thousands of times better than xanthines.[4]

Medicine and hygiene

Chlorophyllin is the active ingredient in a number of internally taken preparations intended to reduce odors associated with incontinence, colostomies and similar procedures, as well as body odor in general. It is also available as a topical preparation, purportedly useful for both treatment and odor control of wounds, injuries, and other skin conditions—notably radiation burns.

Chemistry

PEG-Chlorophyllin is conjugated with the following

α-(3-aminopropyl)-ω-methoxypoly(oxyethylene), PEG-NH2, to form the PEG−chlorophyllin conjugate through acid-amide bonds. PEG−chlorophyllin conjugate was stable toward light illumination under anaerobic condition in comparison with chlorophyllin a. The conjugate catalyzed the reduction of methyl viologen in the presence of 2-mercaptoethanol and the evolution of hydrogen gas in the presence of methyl viologen (an electron carrier), 2-mercaptoethanol (an electron donor) and hydrogenase (Scheme 1). Furthermore, the PEG−chlorophyllin conjugate catalyzed the photoreduction of NADP+ or NAD+ in the presence of ascorbate as an electron donor and ferredoxin-NADP+ reductase as the coupling enzyme. Utilizing the reducing power of NADPH generated by the PEG−chlorophyllin conjugate under the illumination, CO2 fixation was accomplished by the synthesis of malate (C4) from pyruvate (C3) and CO2 in the presence of malic enzyme (Scheme 2). These reactions mentioned above can not proceed in the dark or without each enzyme.

References

  1. ↑ 1.0 1.1 Castro DJ, Löhr CV, Fischer KA, Waters KM, Webb-Robertson BJ, Dashwood RH, Bailey GS, Williams DE (2009). "Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesi". CARCINOGENESIS 30 (2): 315–320. doi:10.1093/carcin/bgn280. PMC 2722150. PMID 19073876.
  2. ↑ "Duranat Cu Chlorophyllin WSP (Natural Green 3-1 CI 75810-1)". Retrieved 15 October 2012.
  3. ↑ Keshava C, Divi RL, Einem TL, Richardson DL, Leonard SL, Keshava N, Poirier MC, Weston A (2009). "Chlorophyllin significantly reduces benzo[a]pyrene-DNA adduct formation and alters cytochrome P450 1A1 and 1B1 expression and EROD activity in normal human mammary epithelial cells". ENVIRONMENTAL AND MOLECULAR MUTAGENESIS 50 (2): 134–144. doi:10.1002/em.20449. PMC 2637934. PMID 19152381.
  4. ↑ Osowski A, Pietrzak M, Wieczorek Z, Wieczorek J (2010). "Natural compounds in the human diet and their ability to bind mutagens prevents DNA-mutagen intercalation". JOURNAL OF TOXICOLOGY AND ENVIRONMENTAL HEALTH, PART A 73 (17-18): 1141–1149. doi:10.1080/15287394.2010.491044. PMID 20706936.

External links