IL283292B2 - Antiviral active cinnamon extract and process - Google Patents
Antiviral active cinnamon extract and processInfo
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- IL283292B2 IL283292B2 IL283292A IL28329221A IL283292B2 IL 283292 B2 IL283292 B2 IL 283292B2 IL 283292 A IL283292 A IL 283292A IL 28329221 A IL28329221 A IL 28329221A IL 283292 B2 IL283292 B2 IL 283292B2
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Description
Antiviral active Cinnamon extract and process TECHNOLOGICAL FIELD This present invention relates to a cinnamon extract and a process for obtaining the extract by natural water extract of Cinnamon Cassia bark in large scale.
BACKGROUND ART References considered to be relevant as background to the presently disclosed subject matter are listed below:- WHO Influenza (seasonal) factsheets 2018, available at:https://www.who.int/news-room/fact-sheets/detail/influenza-(seasonal)- Killbourne, E.D., Zhang, Yan, B., Lin, Mei-Chen 2006 "Influenza pandemic of the 20th century" Emerging Infections Diseases (Centers for Disease Control and Prevention) 12 (1), 299- Premanathan et al, Indian J Med Res . 2000 Sep;112:73-7.- Fink, R.C., Roschek, B., Alberte, R.S., 2009 International Medical Press 2040-2066- Barak, I., Ovadia,M. Natural inhibitor of influenzaA-PR8 extracted from cinnamon. 18th ICAR meeting, April 11-14, 2005, Barcelona, Spain. Antiviral Research Vol 65, A65- Ovadia, M., Kallily, Y., Bernstein, E. 2009. Cinnamon fraction neutralizes avian influenza H5N1 both in-vitro and in-vivo. 22nd ICAR meeting, 3-May 2009, Miami Beach, Florida. Antiviral Research Vol. 82(2), A35- Sevillia, G. Kamensky, M., Finger, A., Ovadia, M.2007. Cinnamon Extract Inhibits Avian Influenza H9N2 Both in-vitro and in-vivo. Options for the control of Influenza VI., p. 467-469- Munazza, F., Zaidi, N.S., Amraiz, D., Afzal F. 2016 In Vitro Antiviral Activity of Cinnamomum cassia and its Nanoparticles Against H7NInfluenza A Virus. J. Microbiol. Biotechnol. (2016), 26(1), 151-159- Kallily, I. Kamensky, M. Finger, A. Ovadia, M. 2010. Immunization against Newcastle disease virus using cinnamon fraction. Modern Veterinary Vaccines and Adjuvants (MVVA) conference, November 17-19, Budapest Hungary.- Gueta, K., Kamensky, M. Finger, A., Ovadia, M. 2008. Immunization against Newcastle Disease Virus Using Cinnamon Fraction. Annual meeting of Veterinary Institute Bet- Dagan. Israel Journal of Veterinary Medicine Vol. 63(2)- Klaus A ., Wöhrlin F., Lindtner O., Heinemeyer G., Lampen A. 2010- Toxicology and risk assessment of coumarin: focus on human data. 2010 028016069-01 - Mol. Nutra Food Res.2010 Feb;54(2):228-39.
Acknowledgement of the above references herein is not to be inferred as meaning that these are in any way relevant to the patentability of the presently disclosed subject matter.
BACKGROUND Various Viral infections have major impact on global health. Despite the availability of vaccines, Influenza is still associated with significant morbidity and mortality. The World Health Organization estimates that worldwide, annual influenza epidemics result in about 3-5 million cases of severe illness and about 290,000 to 690,0deaths (Influenza (Seasonal) World Health Organization 2018).Few viral pandemics outbreaks occurred during the last century at about 10 years intervals (Killbourne et al. 2006), requiring development of new vaccines, or modification of existing vaccines to fit new strains. Currently the COVID 19 outburst significantly affects the everyday life of every human being! The novel coronavirus (COVID-19) pandemic is a major medical challenge with high morbidity and mortality. The high rate of infection, together with significant progression rates to acute respiratory distress syndrome (ARDS) and pneumonitis, places high stress on the global medical and economic communities. Due to the anticipated long development time, vaccines, which are major weapon in disease prophylaxis, are not yet available. Moreover, vaccines, even when available, are usually much less efficacious for older population and the immune- compromised patients. They are relatively expensive, require refrigeration in storage and transportation, and are therefore hardly applicable in developing countries and isolated territories.
Alternative approach to the development of a new vaccine, is separation and isolation of compounds which are already available in nature. More specifically- Plant sources with proven and active anti-viral and anti-inflammatory properties.Cinnamon has been valued for its medicinal properties for thousands of years, and is classified as a medicinal plant in many countries around the world. The ground bark powder and its extracts are consumed broadly both as spice and as food supplement. Modern science supports the following Cinnamon properties: (a) loaded with powerful antioxidants such as polyphenols; (b) the antioxidants in cinnamon have anti- 028016069-01 inflammatory effect; (c) cinnamon can dramatically reduce insulin resistance; (d)cinnamon reduce blood sugar levels, having a potent anti-diabetic effect. Further, cinnamon exhibit significant antiviral properties: (1) a laboratory study looking at HIV- infected cells found that cinnamon was the most effective treatment of all 69 medicinal plants studied, (Premanathan et al,. 2000); (2) test-tube studies have shown that cinnamon can help fight HIV-1, the main type of HIV virus in humans, (Fink et al, 2009); (3) cinnamon aqueous extract showed ability to inhibit various strains of Influenza A including H1N1 (Barak& Ovadia, 2005), Avian influenza H5N1 (Ovadia et al 2009), H9N2 (Sevillia et al, 2007), H7N3 (Munazza et al, 2016); (4) cinnamon aqueous extract exhibited antiviral activity on Newcastle virus (Kallily et al, 2010) and Sendai virus (Gueta& Ovadia, 2005); (5) high molecular weight Cinnamon extract performed in large variety of viral applications as demonstrated by M. Ovadia in USP9364511 (2006). Cinnamon High Molecular Weight Fraction enables a unique inactivation of enveloped viruses and can be applied in the prevention/treatment of specific viral infections. The pre-clinical work suggest that this Cinnamon extract immediately inhibits viral activity by adhering to the viral envelope. This process is not membrane destructing, but rather the virus remains intact, enabling the immune system to recognize it and produce protective antibodies.
GENERAL DESCRIPTION The preset invention is directed to a polyphenol extract from cinnamon bark in the form of nanoparticles and to an improved large-scale process for obtaining the extract that was shown to exhibit broad anti-viral properties. The polyphenol extract is characterized by its molecular weight, water solution, viscosity and its particle size when measured by Dynamic Light Scattering (DLS) and/or Transmission electron microscopy (TEM). The polyphenol extract is obtained solely by physical separation processes with no chemical reactions or chemical additives. Thus, the present invention is directed to a polyphenol extract from cinnamon bark that is slightly water soluble where the water solution indicates a nano-dispersion characterized by;- having a molecular weight of less than 10KD when determined by aqueous Gel Permeation Chromatography (GPC);- intrinsic viscosity in water of 0.1-1.0 using Ubbelohde viscometer. 028016069-01 The polyphenol extract according to the present invention is in the form of nanoparticles in the size of 100-500 nanometer when determined by Dynamic Light Scattering (DLS) and/or Transmission electron microscopy (TEM). Preferably, the particle size may be in the range of 100-nanometer.
The polyphenol extract preferably has a molecular weight in the range of 3-5 KD, most preferably about 4KD when determined by GPC. The intrinsic viscosity is 0.25 or less. The size of the nanoparticles are about 150 nanometer.The present invention is further directed to a cinnamon extract obtained by a process comprising:- mixing cinnamon powder, pulp or flakes with an aqueous phosphate buffer solution to obtain an aqueous solution that is agitated;- centrifuging the aqueous solution to obtain a supernatant;- heating the supernatant followed by cooling;- passing the supernatant through a GAP filter to obtain a crude extract;- exposing the crude extract to ultrafiltration or nanofiltration having a cutoff membrane of 1 KD to 10 KD and collection the retentate having a volume of about 10% of the crude extract;- optionally re-exposing the retentate of the ultrafiltration or nanofiltration process to a second round;- concentrating the obtained retentate or combined retentate to obtain a liquid or powder product.
The cinnamon extract is characterized by- having a molecular weight of less than 10KD when determined by aqueous Gel Permeation Chromatography (GPC);- an intrinsic viscosity in water of 0.1-1.0 when determined by Ubbelohde viscometer;being in the form of nanoparticles in a size of 100-500 nanometer when determined by Dynamic Light Scattering (DLS) and/or Transmission electron microscopy (TEM).Preferably, the particle size may be in the range of 100-nanometer. 028016069-01 The present invention is yet further directed to a polyphenol extract or a cinnamon extract or use as an antiviral agent inhibiting viral replication. The polyphenol extract or cinnamon extract may be formulated into lozenges, candy, foods such as ice cream and beverages, may be incorporated into compressed tablets or loaded in hard shell capsules for oral intake, or may be dispersed in water for nasal spray or ocular delivery to treat viral infections.
BRIEF DESCRIPTION OF THE DRAWINGS In order to better understand the subject matter that is disclosed herein and to exemplify how it may be carried out in practice, embodiments will now be described, by way of non-limiting example only, with reference to the accompanying drawings, in which:F ig. 1A: provides pictorial demonstrations of the cinnamon extract (a) – powder; (b) – supernatant; (c) - diluted supernatant; (d) - lyophilized particulate of the extract.F ig. 1B: demonstrates the interaction of the cinnamon extract with FeCldemonstrating the presence of hydroxyls.F ig. 2 provides a FT-IR analysis of the cinnamon extract.F ig. 3 provides Gel Permeation Chromatography (GPC) of the cinnamon extract.Figs 4A and 4B provide Transmission Electron Microscopy (TEM) images of the cinnamon extract.
DETAILED DESCRIPTION OF EMBODIMENTS The present invention makes use of cinnamon, preferably cinnamon cassia for extracting at least one fraction of the cinnamon previously found to have antiviral activity by a process that employs membrane technology. The resultant extract product is polyphenol nanoparticles characterized by shape, size, molecular weight, viscosity. The membrane technology according to the present invention includes filtration with organic or mineral membranes, membranes with a variety of cutoff sizes to be used at different stages of the process. In particular, the present invention makes use of ultrafiltration or nanofiltration of an aqueous or buffer extraction of crude cinnamon or an ultrafiltration of an aqueous or buffer extraction of a previously CO2 supercritical or non-polar organic solvent extraction of cinnamon, where process is conducted without the involvement of any chemical reagents other than the aqueous solution or the aqueous buffer. The 028016069-01 cinnamon source may be natural cinnamon bark, waste or residue of the flavor industry, that is either de-oiled and/or de-fatted cinnamon pulp, flake, or powder or did not undergo a process of de-oiling or de-fatting. Hence, the present invention is directed to an improved process of cinnamon extraction that can use a source of cinnamon that avoids undesired compounds.According to the present invention cinnamon bark whether crude cinnamon or waste from the flavor industry, is either grounded or subject to CO2 supercritical or nonpolar organic solvent extraction of dried bark cinnamon cassia to obtain pulp, flakes, and the pulp or flakes are mixed with an aqueous solution that may be an aqueous solution comprising a buffer, preferably phosphate buffer. The cinnamon can be mixed with a cold or hot aqueous solution or under ambient conditions. The phosphate buffer when used is in a concentration of 0.01- 0.05M, preferably, 0.02M, 0.03M or 0.04M. The ratio between the cinnamon source in any of its forms and the aqueous solution water comprising the buffer or not buffer being in the range of 1: 3 – 1-50, preferably 1:5 -1:30. The solution is mixed for a period of several hours. The mixture is stirred at ambient temperature, or under cold or hot conditions. The mixture is stirred for a period between 3 and 30 hours, preferably, 3, 4, 5, 6, 7, 8, 10 to 20, 21, 22, 23, 24 or 30 hours at ambient temperature. The mixing of the cinnamon material and the buffer may also be a two-step process, wherein initially the cinnamon source, is mixed with the buffer at a ratio of 1:4- 1:7, preferably 1:5 in ball mill for a period 2-5, preferably 3 hours followed by further dilution to a ratio of 1:18- 1:22, preferably 1:20 and agitated for additional 5-8, preferably 6 hours. The polyphenol extract was obtained as dry dark brown fine powder having slightly solubility in water (Figure 1A). Turning in particular to Fig. 1A, are given four appearances of the extract: (a) Cinnamon extract powder that was obtained by the process of the present application; (b) the supernatant concentrate; (c) diluted supernatant; (d) lyophilized water-soluble fraction of the cinnamon extract. The color and appearance of the supernatant and the lyophilized material that were obtained for both untreated (water, no pH adjusted) and treated (pH adjusted to 10 using NaOH) cinnamon extract remain similar.The presence of phenolic group was assessed by the reaction of the dried extract with FeCl3 and the color change from brown to purple associated with the interaction (Figure 1B). Turning to in particular to Fig. 1B, are given (A) the cinnamon extract dissolved in water; (B) an aqueous FeCl3 solution; (C) the result of the addition of the 028016069-01 aqueous FeCl3 to the cinnamon extract that gives the dark greenish violet color precipitate indicative of the presence of phenolic group.Further, when the cinnamon extract heated to 300ºC, some part was melted and the other part is not. This is due to the presence of mixture of organic and inorganic compounds. The presence of a rather high percentage of oxygen is also confirmed by the elemental analysis given below (Example 1).The extract powder of this invention is farther formulated into lozenges, candy, and functional foods such as ice cream and beverages. The particles may be incorporated into compressed tablets or loaded in hard shell capsules for oral intake. The cinnamon extract powder may be dispersed in water for nasal spray or ocular delivery to treat viral infections.The term "about" as used throughout the application is understood as the indicated value having a range of ±10%.The following experiments were done for characterization of the polyphenol extract obtained by extraction from cinnamon and determining its properties. Generally, the extraction is done by the methods that are described in IL application No. 277753.
Examples Example 1: Elemental analysis of cinnamon extractElemental analysis of cinnamon extract shows the percentages of carbon, hydrogen and nitrogen are: 52.52%, 4.64% and 0.00 % N, respectively. In addition, the results revealed that the absence of nitrogen atoms. These results clearly indicate the presence of a high percentage of oxygen atoms, which confirm the polyhydroxy compound.
Example 2: Solubility measurement:The solubility test for the cinnamon extract powder was performed in water (no pH adjustment) and at pH 10 (pH adjusted using NaOH). 100 mg of the material was dispersed in the 3 mL of the aqueous medium and kept on overnight mixing at high speed. Thereafter, the aqueous mixture was centrifuged at 10,000 rpm for 30 min at 40C. Both the precipitate and the supernatant (soluble fraction) were collected in separate vials and lyophilized. 028016069-01 The water/solvent solubility of the cinnamon extract was determined by adding 100 mg of the extract powder in 1 ml of solvent or water at pH7 or pH10. After 24 hours of agitation, the mixture was centrifuged at 4000 rpm for 10 min. and the clear supernatant was isolated and lyophilized. The soluble part was 30 mg and the insoluble part was mg (3% solubility). Among organic solvents, cinnamon extract had some solubility in DMSO (0.7%) and sparingly soluble in ethanol and chloroform. The solubility of cinnamon extract in various solvents is given in Table 2. The clear supernatant was in fact a dispersion of nanoparticles of 145-180 nm as determined by particle size analyzer, Dynamic Light Scattering (DLS).
Table 2: Solubility of cinnamon extract in various solvents No.S.Solvent Solubility* 1Water (DDW, pH7 or pH10)3.0% 2 DMSO 0.7%Ethanol Sparingly soluble (<0.2%)Chloroform Sparingly soluble (<0.2%) Example 3: Dynamic Light Scattering (DLS) and zetapotential measurement: The diluted sample of soluble fraction of the cinnamon extract in water was tested for any presence of nanoparticulate using DLS. The results reveal that the soluble fraction of the cinnamon extract which was prepared without any pH treatment showed the presence of nanoparticulate with size of 148.6+23.5 nm. On the other hand, the soluble fraction of the cinnamon extract which was prepared with pH treatment showed the presence of nanoparticulate with size of 187.4+110.4 nm. The zeta potential data reveal a high negative charge on the surface of the nanoparticles (Table 3). If the nanoparticles in suspension have a large negative potential, then they will tend to repel each other and there will be no tendency for the particles to come together. Therefore, we did not observe any sedimentation in the samples when kept undisturbed over time at room temperature. The surface charge was simultaneously determined using the same diluted solution. DLS and zetapotential was performed using Zetasizer (Nano ZS, Malvern Instruments, UK) 028016069-01 equipped with inbuilt software. Particle size analysis of the clear supernatant indicated that the extract is in the form of nanoparticles of 100-200, preferably at 120-150 nm. This indicate that the compound is not water soluble but insoluble nanoparticles of the compound. The results are given in Table 2 below.
Table 3: DLS and surface charge determination of the soluble fraction of cinnamon powder in water.Sample Size(nm)/DLSPDI Zetapotential (mV)Solubleobtainedtreatment fractionwithout148.6+23.5 0.403+0.124 -22.2+5.90 Soluble fractionafter NaOH treatment187.4+110.4 0.473+0.110 -22.2+7.41 Example 4: Example FT-IR analysis of cinnamon extract:FT-IR spectrum was obtained in neat condition using a Smart iTR ATR sampling accessory for Nicolet iS10 spectrometer with a diamond crystal (Thermo Scientific, Massachusetts) and given in Figure 2. The broad frequency observed at 3269 cm-confirms the hydroxy groups present in the extract. The band detected at 2927 cm-confirms the aliphatic C-H stretching frequency. The bands seen in the region of 16cm-1 and 1107 cm-1 confirm the C=C and C-O stretching frequencies respectively. 028016069-01 Further an NMR analysis of cinnamon extract was also done as follows further confirming the presence of both aromatic and hydroxyl groups. 1H NMR spectra was obtained on a Varian 300 MHz spectrometer, in tubes with 5 mm outside diameters. D2O or DMSO-d6 served as a solvent and shift reference. The 1H NMR spectra of cinnamon extract in DMSO-d6 and D2O was determined. The NMR spectra shows the presence of a broad peak in the range of 7.47-9.70 ppm confirming the presence of aromatic protons. The broad peaks in the range of 4.006.00 ppm exhibit the presence of hydroxyl groups. The peaks at 1.24 ppm and 3. ppm confirms the presence of aliphatic protons.
Example 5: TEM measurement:Transmission electron microscopy (TEM) was used to understand the exact shape of the nanoparticles. The TEM analysis was performed using JEOL JEM-1400Plus by applying ∼10μL of samples resuspended in DDW to a 200- or 400-mesh copper grid covered by carbon-stabilized Formvar film (SPI, West Chester, PA). The samples were dried overnight before scans were performed. The nanoparticles were sequentially stained with negative stain NanoVan® (Methylamine Vanadate) and the images were analyzed using inbuilt software (SoftImaging System GmbH, Münstar, Germany).Turning to Fig. 3, TEM measurements indicate that the nanoparticles were nearly spherical. As shown in Fig. 2A, the nanoparticles of the fraction that was obtained without any pH treatment was more spherically shaped than compared to the soluble fraction that was obtained after the NaOH treatment Fig. 2B. Overall, the size obtained from the DLS data matches with the TEM images for the nanoparticles.
Example 6: Viscosity of the cinnamon extract:The water solubility of the cinnamon extract was determined at room temperature by adding 100 mg of the extract powder in 1 ml of water or pH10 solution. After 24 hours the mixture was centrifuged and the clear supernatant was isolated that contain 30 mg/ml. Viscosity measurement of the supernatant indicted low viscosity of 0.23 (for 1% in water 25oC using Ubbelohde viscometer). 028016069-01 Example 7: GPC analysis of cinnamon extractThe molecular weight of cinnamon extract was estimated by gel permeation chromatography (GPC) system and eluted with water. Molecular weight was determined relative to pullulan standards with a molecular weight range of 500–100,000 Da. The molecular weight of the cinnamon extract is ~4,000 Da (Figure 4).
Example 7: Antiviral activity: Anti-coronavirus activity of Cinnamon extracts – test resultsIntroduction: A study has been conducted on the particular component of the Cinnamon (CF), extracted. The study examined the potential antiviral activity of CF probably by the Spike-hACE2 interactions using Spike-pseudotyped lentivirus.
Note: Viral entry into human cells is mediated by binding of the SARS-CoV-spike protein (S) receptor-binding domain (RBD) to the host cell hACE2 receptor. Hence disruption of this process is one of the main targets of anti SARS-CoV-2 drugs. Accordingly, most of the developed vaccines trigger the production of anti-RBD antibodies.Since SARS-CoV-2 handling requires biosafety level 3 (BSL-3) labs, it is challenging to use it in conventional biological labs. To overcome this difficulty, the experimental setup is based on lentiviruses expressing SARS-CoV-2 Spike proteins that enters cells by mimicking the SARS-CoV-2 entry mechanism. The binding capacity of the lentiviruse used in this study is about 200 times more efficient than the original COVID 19 virus. The ability of Cinnamon extract 1 and 2 to inhibit Spike-hACE2 interactions was determined using Spike-pseudotyped lentivirus that following entry to target cells generate the expression of a red fluorescent protein. FACS measurements of the marker levels in the presence of inhibitory molecules are compared to the marker levels in the absence of inhibitory molecules (Blank samples) to estimate the potential inhibition of the screened molecule. A crude estimation of the material cytotoxicity was determined by measuring the concentration of cells in each sample following 96 hours incubation with the test material.The cinnamon extract insignificantly affects the viability of living cells. Results of the study indicate that the infection rates decreased significantly in the experimental 028016069-01 setup, meaning that CF inhibited most of the viral activity. These results indicate that cinnamon extracts could be effective in blocking SARS-CoV-2 and potentially other viruses. 028016069-01
Claims (15)
1. A polyphenol extract from cinnamon bark in the form of nanoparticles characterized by; - having a molecular weight of 3-6 kDA when determined by aqueous Gel Permeation Chromatography (GPC); - an intrinsic viscosity in water of 0.1-1.0 when determined by Ubbelohde viscometer at a concentration of 1% and 25oC.
2. The polyphenol extract according to claim 1, wherein the nanoparticle size when determined by Dynamic Light Scattering (DLS) and/or Transmission electron microscopy (TEM) is 100-500 nanometer.
3. The polyphenol extract according to claim 1 or 2, having a particle size of 100-1nanometer.
4. The polyphenol extract according to any one of the preceding claim having a molecular weight of 2-4kDA as determined by gel permeation chromatography.
5. The polyphenol extract according to any one of the preceding claims having an intrinsic viscosity of 0.25 at a concentration of 1% and 25oC.
6. The polyphenol extract according to any one of the preceding claims having antiviral activity.
7. A process for obtaining a polyphenol extract from cinnamon comprising: - mixing cinnamon powder, pulp or flakes with an aqueous phosphate buffer solution to obtain an aqueous solution that is agitated; - centrifuging the aqueous solution to obtain a supernatant; - heating the supernatant followed by cooling; - passing the supernatant through a GAP filter to obtain a crude extract; - exposing the crude extract to ultrafiltration or nanofiltration having a cutoff membrane of 3-6kDA and collection the retentate having a volume of about 10% of the crude extract; - optionally re-exposing the retentate of the ultrafiltration or nanofiltration process to a second round; 283292/ 02801606103- - concentrating the obtained retentate or combined retentate to obtain a liquid or powder product.
8. The process according to claim 7 characterized by: - an intrinsic viscosity in water of 0.1-1.0 when determined by Ubbelohde viscometer at a concentration of 1% and 25oC; - being in the form of nanoparticles in a size of 100-500 nanometer when determined by Dynamic Light Scattering (DLS) and/or Transmission electron microscopy (TEM) .
9. The process of claim 7 or 8, having a nanoparticle size of 100-170 nanometer.
10. The process according to any one of claims 7-9, wherein the polyphenol extract from cinnamon obtained by the process has a molecular weight of 2-6KD as determined by gel permeation chromatography.
11. The process according to any one of claims 7-10, wherein the polyphenol extract from cinnamon obtained by the process has an intrinsic viscosity of less than 0.5 at a concentration of 1% and 25oC.
12. The process according to any one of claims 7-11, wherein the polyphenol extract from cinnamon obtained by the process has antiviral activity.
13. The polyphenol extract of any one of claims 1-6 is farther formulated into lozenges, candy, foods such as ice cream and beverages.
14. The polyphenol extract of any one of claims 1-6 incorporated into compressed tablets or loaded in hard shell capsules for oral intake.
15. The polyphenol extract obtained by the process according to any one of claims 7- dispersed in water for nasal spray or ocular delivery to treat viral infections.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL283292A IL283292B2 (en) | 2021-05-19 | 2021-05-19 | Antiviral active cinnamon extract and process |
| US18/246,911 US20230372424A1 (en) | 2020-10-01 | 2021-10-01 | Antiviral active cinnamon extract and process |
| PCT/IL2021/051186 WO2022070198A1 (en) | 2020-10-01 | 2021-10-01 | Antiviral active cinnamon extract and process |
| EP21874742.6A EP4221732A4 (en) | 2020-10-01 | 2021-10-01 | Antiviral active cinnamon extract and process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL283292A IL283292B2 (en) | 2021-05-19 | 2021-05-19 | Antiviral active cinnamon extract and process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| IL283292A IL283292A (en) | 2022-12-01 |
| IL283292B1 IL283292B1 (en) | 2025-06-01 |
| IL283292B2 true IL283292B2 (en) | 2025-10-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| IL283292A IL283292B2 (en) | 2020-10-01 | 2021-05-19 | Antiviral active cinnamon extract and process |
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| Country | Link |
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| IL (1) | IL283292B2 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060073220A1 (en) * | 2004-07-08 | 2006-04-06 | Daugherty F J | Cinnamon extract enriched for polyphenols and methods of preparing same |
| US20070292540A1 (en) * | 2006-03-23 | 2007-12-20 | Gow Robert T | Extracts and Methods Comprising Cinnamon Species |
| US20130035380A1 (en) * | 2011-08-01 | 2013-02-07 | Akay Flavours & Aromatics Pvt Ltd. | Process for selective extraction of bioactive and bioavailable cinnamon polyphenols and procyanidin oligomers and a stable composition thereof |
| WO2018209293A2 (en) * | 2017-05-11 | 2018-11-15 | The Regents Of The University Of California | Nanoscale multiple emulsions and nanoparticles |
-
2021
- 2021-05-19 IL IL283292A patent/IL283292B2/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060073220A1 (en) * | 2004-07-08 | 2006-04-06 | Daugherty F J | Cinnamon extract enriched for polyphenols and methods of preparing same |
| US20070292540A1 (en) * | 2006-03-23 | 2007-12-20 | Gow Robert T | Extracts and Methods Comprising Cinnamon Species |
| US20130035380A1 (en) * | 2011-08-01 | 2013-02-07 | Akay Flavours & Aromatics Pvt Ltd. | Process for selective extraction of bioactive and bioavailable cinnamon polyphenols and procyanidin oligomers and a stable composition thereof |
| WO2018209293A2 (en) * | 2017-05-11 | 2018-11-15 | The Regents Of The University Of California | Nanoscale multiple emulsions and nanoparticles |
Non-Patent Citations (1)
| Title |
|---|
| FATIMA, MUNAZZA, ET AL., IN VITRO ANTIVIRAL ACTIVITY OF CINNAMOMUM CASSIA AND ITS NANOPARTICLES AGAINST H7N3 INFLUENZA A VIRUS, 28 January 2016 (2016-01-28) * |
Also Published As
| Publication number | Publication date |
|---|---|
| IL283292A (en) | 2022-12-01 |
| IL283292B1 (en) | 2025-06-01 |
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