Sophoraflavanone G

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Sophoraflavanone G
Sophoraflavanone G structure.png
Names
IUPAC name
(2S)-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-4H-chromen-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3/t15-,23+/m1/s1 X mark.svgN
    Key: XRYVAQQLDYTHCL-CMJOXMDJSA-N X mark.svgN
  • InChI=1/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3/t15-,23+/m1/s1
    Key: XRYVAQQLDYTHCL-CMJOXMDJBK
  • [H][C@@](CC=C(C)C)(Cc1c(O)cc(O)c2C(=O)C[C@H](Oc12)c1ccc(O)cc1O)C(C)=C
Properties
C
25H
28O
6
Molar mass 424.48622 g/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
No known hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sophoraflavanone G [1] is a volatile phytoncide, released into the atmosphere, soil and ground water, by members of the Sophora genus. Due to an increase in the rates of antibiotic-resistant bacteria, scientific efforts have focused on finding either naturally-made or genetically modified compounds that can treat and or prevent these harmful and sometimes deadly bacteria. Sophoraflavanone G, due to its use as a phytoncide, has been found to impact the growth of antibiotic-resistant bacteria and enhance the effect of currently used antibiotics.

Contents

Background information on phytoncides

1st discovered by B.P. Tokin, the word “phytoncide” literally means, exterminated by the plant. Phytoncides are a biologically active substance of plant origin that kills or inhibits growth and development of bacteria, microscopic fungi, and protozoa. Phytoncides play an important role in plant immunity and in the relationships between organisms within an ecosystem. [2]

The ability to produce phytoncides is a quality common among plants. The release of phytoncides increase when a plant is injured. Phytoncide compound composition's vary depending on whether the compound is considered a glycoside, terpenoid, or other secondary metabolites (not found in the major classes of natural compounds). [3]

Categories of phytoncides

There are two categories of phytoncides: 1) Nonexcretory phytoncides (found in the protoplasma of cells) and 2) Volatile phytoncides (released into the atmosphere, soil and water) Examples of plants releasing each type of phytoncide are: (nonexcretory)onion, garlic, and horseradish, and (volatile) pine, oak, eucalyptus, and members of the Sophora genus. [3]

Sophora Flavescens Sophora flavescens.jpg
Sophora Flavescens

Some phytoncides effect only insects feeding on the plant, acting on the insect's autonomic nervous system. Other phytoncides target mainly microbes. The antimicrobial potency and range of phytoncides vary greatly among species. Some can kill many types of protozoa, bacteria, fungi, and insects within minutes or seconds, while others may take hours or only harm the pest. In addition to acting as a “plant protector”, phytoncides can also impede the reproduction of pests. [3]

General effect on environment

Regarding how phytoncides effect a plant's immunity, for example, 1 hectare of pine forest will release approximately 5 kg of volatile phytoncides into the atmosphere in one day, reducing the amount of microflora in the air and essentially sterilizing the atmosphere among the forest, containing only about 200-300 bacterial cells/m3. This effect is found more commonly in coniferous forests as opposed to deciduous; something to consider when planning resort locations and urban landscaping. [3]

General uses of phytoncides

Because of the antimicrobial properties of phytoncides, extensive research has been done to investigate their use in medicine, as a plant protector in greenhouses, and in the shipping and storing of perishables like fruits and vegetables.

One volatile phytoncide, sophoraflavanone G, is of particular interest, due to its use in treating methicillin-resistant staphylococcus aureus and vancomycin-resistant enterococci bacteria.

Sophoraflavanone G

USDA Map of North American plant hardiness zones USDA Hardiness zone map.jpg
USDA Map of North American plant hardiness zones

Sophoraflavanone G is among the volatile category of phytoncides, released into the atmosphere, soil, and ground water by the plant species Sophora flavescens , [4] Sophora pachycarpa, and Sophora exigua; all found to grow within the United States in a variety of soil types, within temperate conditions, no lower than 0 °F (US zone 6 - yellow areas shown to the right). Sophoraflavanone G is released in order to protect the plant against harmful protozoa, bacteria, and fungi. Sophoraflavanone G, also called kushenin (in traditional Chinese medicinal recipes), is a flavonoid compound.

Flavonoids

Flavonoids are a class of secondary metabolites found in plants that fulfill a wide variety of functions. They are most commonly known as plant pigments in flower petals to attract pollinators and for their antioxidant activities, providing some hope for consumers regarding medicinal uses, potentially cancer treatment. It has not been until recently that their use as a phytoncide was made known. [5]

Toxicity

No known toxicity reports against humans have been found related to phytoncides, including Sophoraflavanone G.

Uses of Sophoraflavanone G: antimicrobial agent against MRSA and VRE

In result to the increasing cases of MRSA and VRE, a tremendous amount of research has gone into finding reliable methods of controlling and potentially preventing antibiotic-resistant strains of bacteria. One promising candidate for the treatment of these deadly bacteria is sophoraflavanone G. Throughout the scientific literature, it has been cited that sophoraflavanone G has had considerable success against antibiotic-resistant bacteria like S. aureus and Enterococci.

Staphylococcus aureus and Enterococcus are two of the leading causes of nosocomial (contracted while in a health facility) infections in hospitals and nursing homes, and reports on methicillin-resistant staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) in hospitals have increased worldwide.

S.aureus Staphylococcus aureus VISA 2.jpg
S.aureus
Enterococcus Enterococcus histological pneumonia 01.png
Enterococcus

MRSA involves a strain of Staphylococcus aureus bacteria that normally lives on the skin and sometimes in the nasal passages of healthy people. In addition, these particular strains of S. aureus do not respond to some of the antibiotics used to treat staph infections. The bacteria can cause infection when they enter the body through a cut, sore, catheter, or breathing tube. Once infected, the case can be minor and local, or more serious, involving complications with the major tissues within the patient, specifically heart, lungs, blood, and bone. Serious staph infections are more common in people with weak immune systems, particularly patients in hospitals and long-term healthcare facilities and those who are healthy, but otherwise in close contact with many individuals through shared use of equipment and personal items, like athletes and children in daycare. [6]

Serious staph infections are quite difficult to treat, due to increasing numbers of antibiotic-resistant strains of S. aureus in the population. If left untreated, serious staph infections can result in organ failure and death. [6]

Enterococcus are normally present in the human intestines, female genital tract and often within the environment. When these bacteria cause infections, usually within the urinary tract, bloodstream, or in wounds associated with catheters or surgical procedures, the common antibiotic used to treat these cases is Vancomycin. In some instances, enterococci have become resistant to this drug and are, in result, referred to as vancomycin-resistant enterococci (VRE). Most of these infections occur within the long-term healthcare setting. [7]

Serious VRE infections are common among those who have been previously treated with the antibiotic vancomycin and hospitalized for long periods of time, those who have a weak immune system, any patients who have recently undergone surgery or those individuals with medical devices that stay inside their bodies for long periods of time (mainly catheters). VRE is often spread by the contaminated hands of caregivers, or directly after those infected with VRE, touch surfaces. VRE is not spread through the air by coughing or sneezing. [7]

Research into antimicrobial activity of Sophoraflavanone G

Research conducted in Japan, in 1995, report that the use of sophoraflavanone G completely inhibits the growth of 21 strains of methicillin-resistant S. aureus at concentrations of 3.13-6.25 µg/mL. When this compound is combined with vancomycin, minocycline, and rifampicin, the rates of inhibition increased, indicating a partially synergistic effect with anti-MRSA antibiotics (Sato et al. 1995). [8] Similarly in Iran, in 2006, a research group reported that the antibacterial activity of gentamicin was enhanced through the use of sophoraflavanone G, citing that bacterial colonies of S. aureus, on TLC plates showed a significant decrease (4x) in growth while in the presence of small amounts (.03 µg/mL) of this compound (Fakhimi et al. 2006). [9] Additional studies, done in South Korea in 2009 and Romania in 2010, support these findings of partially synergistic effects between sophoraflavanone G and various antibiotics, adding that when used either alone, or in conjunction with ampicillin and oxacillin (Cha et al. 2009), [10] and ampicillin, gentamicin, minocycline, and vancomycin hydrochloride (Duka et al. 2010), [3] sophoraflavanone G increases the number of antibiotic-resistant bacteria (MRSA & VRE) killed within plated colonies (based on FIC indices).

Additional uses of Sophoraflavanone G

In addition to the use of sophoraflavanone G as treatment against bacteria and other microflora present within the environment, by plants and humans alike, this compound has also been reported to be useful in the treatment of a variety of maladies, ranging from Eicosanoid-related skin inflammation such as atopic dermatitis, to treating more serious medical issues like malaria and myeloid leukemia.

Regarding anti-inflammatory treatments, research by Kim et al. (2002) reported that sophoraflavanone G inhibited eicosanoid generating enzymes, and prostaglandin production, suggesting its potential use for eicosanoid-related skin inflammation such as atopic dermatitis. [11] In 2004, Youn et al. reported that sophoraflavanone G (in addition to other flavanoids) showed moderate anti-malarial activities based on the EC50 values within mice populations, potentially due to methoxyl groups found within the structure. [12] In addition, sophoraflavanone G has also been said to have implications for the treatment of myeloid leukemia, based on the research findings of Kang et al. (2000), who reported that sophoraflavanone G exhibited cytotoxic activity against human myeloid leukemia HL-60 cells. [13]

Related Research Articles

<i>Staphylococcus aureus</i> Species of Gram-positive bacterium

Staphylococcus aureus is a Gram-positive round-shaped bacterium, a member of the Firmicutes, and is a usual member of the microbiota of the body, frequently found in the upper respiratory tract and on the skin. It is often positive for catalase and nitrate reduction and is a facultative anaerobe that can grow without the need for oxygen. Although S. aureus usually acts as a commensal of the human microbiota it can also become an opportunistic pathogen, being a common cause of skin infections including abscesses, respiratory infections such as sinusitis, and food poisoning. Pathogenic strains often promote infections by producing virulence factors such as potent protein toxins, and the expression of a cell-surface protein that binds and inactivates antibodies. S. aureus is one of the leading pathogens for deaths associated with Antimicrobial resistance and the emergence of antibiotic-resistant strains such as methicillin-resistant S. aureus (MRSA) is a worldwide problem in clinical medicine. Despite much research and development, no vaccine for S. aureus has been approved.

Vancomycin Pharmaceutical drug

Vancomycin is an antibiotic medication used to treat a number of bacterial infections. It is recommended intravenously as a treatment for complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also recommended by mouth as a treatment for severe Clostridium difficile colitis. When taken by mouth it is very poorly absorbed.

Methicillin-resistant <i>Staphylococcus aureus</i> Bacterium responsible for difficult-to-treat infections in humans

Methicillin-resistant Staphylococcus aureus (MRSA) is a group of Gram-positive bacteria that are genetically distinct from other strains of Staphylococcus aureus. MRSA is responsible for several difficult-to-treat infections in humans. It caused more than 100,000 deaths attributable to antimicrobial resistance in 2019.

Methicillin Antibiotic medication

Methicillin, also known as meticillin, is a narrow-spectrum β-lactam antibiotic of the penicillin class.

Vancomycin-resistant <i>Staphylococcus aureus</i> Antibiotica resistant bacteria

Vancomycin-resistant Staphylococcus aureus (VRSA) are strains of Staphylococcus aureus that have become resistant to the glycopeptide antibiotic vancomycin.

Glycopeptide antibiotic

Glycopeptide antibiotics are a class of drugs of microbial origin that are composed of glycosylated cyclic or polycyclic nonribosomal peptides. Significant glycopeptide antibiotics include the anti-infective antibiotics vancomycin, teicoplanin, telavancin, ramoplanin and decaplanin, corbomycin, complestatin and the antitumor antibiotic bleomycin. Vancomycin is used if infection with methicillin-resistant Staphylococcus aureus (MRSA) is suspected.

Tigecycline

Tigecycline, sold under the brand name Tygacil, is an tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline administered intravenously. It was developed in response to the growing rate of antibiotic resistant bacteria such as Staphylococcus aureus, Acinetobacter baumannii, and E. coli. As a tetracycline derivative antibiotic, its structural modifications has expanded its therapeutic activity to include Gram-positive and Gram-negative organisms, including those of multi-drug resistance.

Vancomycin-resistant <i>Enterococcus</i> Bacterial strains of Enterococcus that are resistant to the antibiotic vancomycin

Vancomycin-resistant Enterococcus, or vancomycin-resistant enterococci (VRE), are bacterial strains of the genus Enterococcus that are resistant to the antibiotic vancomycin.

Dicloxacillin

Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

Oxacillin

Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

Oritavancin

Oritavancin, sold under the brand name Orbactiv among others, is a semisynthetic glycopeptide antibiotic medication for the treatment of serious Gram-positive bacterial infections. Its chemical structure as a lipoglycopeptide is similar to vancomycin.

Lysostaphin is a Staphylococcus simulans metalloendopeptidase. It can function as an bacteriocin (antimicrobial) against Staphylococcus aureus.

Targanta Therapeutics Corporation was a biopharmaceutical company headquartered in Cambridge, Massachusetts. The company also had operations in Indianapolis, Montreal and Toronto. Targanta completed its initial public offering on October 9, 2007 and traded on the Nasdaq market under the symbol: TARG. Targanta was acquired by The Medicines Company in 2009.

Dalbavancin

Dalbavancin is a novel second-generation lipoglycopeptide antibiotic medication. It belongs to the same class as vancomycin, the most widely used and one of the few treatments available to patients infected with methicillin-resistant Staphylococcus aureus (MRSA).

Staphylococcal infection Medical condition

A staphylococcal infection or staph infection is an infection caused by members of the Staphylococcus genus of bacteria.

Tedizolid Oxazolidinone-class antibiotic

Tedizolid, is an oxazolidinone-class antibiotic. Tedizolid phosphate is a phosphate ester prodrug of the active compound tedizolid. It was developed by Cubist Pharmaceuticals, following acquisition of Trius Therapeutics, and is marketed for the treatment of acute bacterial skin and skin structure infections.

Ceftaroline fosamil

Ceftaroline fosamil (INN), brand name Teflaro in the US and Zinforo in Europe, is a cephalosporin antibiotic with anti-MRSA activity. Ceftaroline fosamil is a prodrug of ceftaroline. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria. It retains some activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria, but its effectiveness is relatively much weaker. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection.

Anthracimycin

Anthracimycin is a polyketide antibiotic discovered in 2013. Anthracimycin is derived from marine actinobacteria. In preliminary laboratory research, it has shown activity against Bacillus anthracis, the bacteria that causes anthrax, and against methicillin-resistant Staphylococcus aureus (MRSA).

Teixobactin is a peptide-like secondary metabolite of some species of bacteria, that kills some gram-positive bacteria. It appears to belong to a new class of antibiotics, and harms bacteria by binding to lipid II and lipid III, important precursor molecules for forming the cell wall.

Kerry L. LaPlante is an American pharmacist, academic and researcher. She is a Professor of Pharmacy and the Chair of the Department of Pharmacy Practice at the University of Rhode Island, an Adjunct Professor of Medicine at Brown University, an Infectious Diseases Pharmacotherapy Specialist, and the Director of the Rhode Island Infectious Diseases Fellowship and Research Programs at the Veterans Affairs Medical Center in Providence, Rhode Island.

References

  1. ↑ "Sophoraflavanone G." European Bioinformatics Institute. 17 October 2009.
  2. ↑ "Phytoncide". The Great Soviet Encyclopedia, 3rd Edition (1970-1979).
  3. 1 2 3 4 5 Duka, R., and Ardelean, D. “Phytoncides and Phytoalexins – Vegetal Antibiotics.” Jurnal Medical Aradean (Arad Medical Journal) 13 (2010): 19-25.
  4. ↑ Sophora flavescens (5 February 2011)
  5. ↑ Flavonoids (8 April 2011)
  6. 1 2 "Methicillin-resistant Staphylococcus aureus; Community-acquired MRSA (CA-MRSA); Hospital-acquired MRSA (HA-MRSA)". National Institute of Health. 30 May 2009.
  7. 1 2 "Healthcare-associated infections". Centers for Disease Control and Prevention. 24 November 2010.
  8. ↑ Sato, M., Tsuchiya, H., Takase, I., Kureshiro, H., Tanigaki, S. and Iinuma, M. “Antibacterial activity of flavanone isolated from Sophora exigua against methicillin-resistant Staphylococcus aureus and its combination with antibiotics.” Phytotherapy Research 9 (1995): 509–512.
  9. ↑ Fakhimi A, Iranshahi M, Emami SA, Amin-Ar-Ramimeh E, Zarrini G, Shahverdi AR. “Sophoraflavanone G from Sophora pachycarpa enhanced the antibacterial activity of gentamycin against Staphylococcus aureus.” Zeitschrift für Naturforschung C. (Journal of Biosciences) Sep-Oct(9-10) 2006:769-72
  10. ↑ Cha J., Moon S., Kim J., Jung E., Lee Y. “Antibacterial activity of sophoraflavanone G isolated from the roots of sophora flavescens against methicillin-resistant staphylococcus aureus.” Phytotherapy Research 23 Sep(9) 2009: 1326-31.
  11. ↑ Kim D., Chi Y., Son K., Chang H., Kim J., Kang S., and Kim H. “Effects of sophoraflavanone G, a prenylated flavonoid from Sophora flavescens on cyclooxygenase-2 and in vivo inflammatory response.” Archives of Pharmacal Research Jun 25(3) 2002:329-35.
  12. ↑ Youn Chul Kim, Hye-Sook Kim, Yusuke Wataya, Dong Hwan Sohn, Tai Hyun Kang, Myung Soo Kim, Yong Man Kim, Geon-Mok Lee, Jong-Duk Chang and Hyun Park, “Antimalarial Activity of Lavandulyl Flavanones Isolated from the Roots of Sophora flavescens”, Biological & Pharmaceutical Bulletin 27 (2004): 748-750.
  13. ↑ Tai-Hyun Kang, Sei-Joon Jeong, Won-Gil Ko, Na-Young Kim, Byung-Hoon Lee, Masanori Inagaki, Tomofumi Miyamoto, Ryuichi Higuchi, and Youn-Chul Kim. “Cytotoxic Lavandulyl Flavanones from Sophora flavescens.” Journal of Natural Products 5 (2000):680–681.
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