WO2023091112A1 - Ace-2 enzyme inhibitory effects of essential oils obtained from the aerial parts of the plants origanum majorana, origanum minutiflorum, origanum onites and origanum vulgare - Google Patents
Ace-2 enzyme inhibitory effects of essential oils obtained from the aerial parts of the plants origanum majorana, origanum minutiflorum, origanum onites and origanum vulgare Download PDFInfo
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- WO2023091112A1 WO2023091112A1 PCT/TR2022/051145 TR2022051145W WO2023091112A1 WO 2023091112 A1 WO2023091112 A1 WO 2023091112A1 TR 2022051145 W TR2022051145 W TR 2022051145W WO 2023091112 A1 WO2023091112 A1 WO 2023091112A1
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- origanum
- minutiflorum
- onites
- majorana
- vulgare
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- 239000000341 volatile oil Substances 0.000 title claims abstract description 27
- 240000007673 Origanum vulgare Species 0.000 title claims abstract description 17
- 240000000783 Origanum majorana Species 0.000 title claims abstract description 15
- 241001518075 Origanum minutiflorum Species 0.000 title claims abstract description 14
- 235000006669 Origanum minutiflorum Nutrition 0.000 title claims abstract description 14
- 240000004373 Origanum onites Species 0.000 title claims abstract description 14
- 235000000003 Origanum onites Nutrition 0.000 title claims abstract description 14
- 235000010677 Origanum vulgare Nutrition 0.000 title claims abstract description 12
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 10
- 102000004190 Enzymes Human genes 0.000 title abstract description 11
- 108090000790 Enzymes Proteins 0.000 title abstract description 11
- 108090000975 Angiotensin-converting enzyme 2 Proteins 0.000 claims description 24
- 102100035765 Angiotensin-converting enzyme 2 Human genes 0.000 claims description 13
- 235000006297 Origanum majorana Nutrition 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 235000007746 carvacrol Nutrition 0.000 claims description 8
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims description 8
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 claims description 8
- 241000711573 Coronaviridae Species 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000003319 supportive effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 230000005764 inhibitory process Effects 0.000 description 13
- 102000053723 Angiotensin-converting enzyme 2 Human genes 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 4
- 241001678559 COVID-19 virus Species 0.000 description 3
- 241000246358 Thymus Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 208000025721 COVID-19 Diseases 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 241001529744 Origanum Species 0.000 description 1
- 235000011203 Origanum Nutrition 0.000 description 1
- 229940096437 Protein S Drugs 0.000 description 1
- 102000029301 Protein S Human genes 0.000 description 1
- 108010066124 Protein S Proteins 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 239000012676 herbal extract Substances 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
Definitions
- the invention relates to the ACE-2 enzyme inhibitory effects of essential oils obtained from the aerial parts, preferably leaves of the plants Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgar e.
- Angiotensin-converting enzyme 2 in short, is an enzyme bound to the outer surface of cells in the arteries, lungs, kidneys, heart, and intestines. ACE2 accelerates the hydrolysis of the angiotensin II hormone, which is a vasoconstrictor, to angiotensin, thereby reducing blood pressure. ACE-2 enzyme is located in the natural balance of our body and some disorders can be associated with this enzyme.
- Natural resources have become very popular in the treatment of diseases. Products and phytochemicals obtained from plants have been included in the preparations used in the pharmaceutical field from the past to the present. Natural products have attracted special attention with these effects because the products of plant origin give very good results in the fight against microorganisms. Today, very successful results have started to be obtained from herbal extracts and natural substances.
- Muchtaridi Muchtaridi et al. summarizes natural flavonoids that have potential efficacy against COVID-19 through ACE2 receptor inhibition. However, these plants do not include Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare plants and the essential oils thereof.
- the primary object of the invention is to obtain essential oils with antiviral effects from the aboveground parts, preferably from the leaves of four different thyme plants, Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare.
- Origanum majorana preferably from the leaves of four different thyme plants, Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare.
- essential oils of four different thyme species were investigated in terms of ACE-2 enzyme inhibition. At this point, as a natural agent, these essential oils separately gave very good results in terms of ACE-2 enzyme inhibition at a concentration of 20 micrograms/mL.
- the object of the invention is to discover and develop effective, natural and domestic agents against the coronavirus, which is of great importance for human health, by obtaining Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare essential oils.
- the pharmaceutical composition obtained by the invention can be used in the preparation of the drug to be used in the treatment of coronavirus disease.
- the pharmaceutical composition obtained by the invention can also be used as a supportive treatment in the treatment of coronavirus disease.
- Figure 1 % inhibition rate of essential oils of the aboveground parts of Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare against Angiotensinconverting enzyme 2 (ACE2).
- ACE2 Angiotensinconverting enzyme 2
- the present invention is a pharmaceutical composition and comprises the essential oils of the aerial parts of the oregano species Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare, and has inhibitory effects against the angiotensin-converting enzyme 2 (ACE2).
- the pharmaceutical composition of the invention optionally comprises at least one pharmaceutically acceptable excipient.
- the invention has shown the effect of high ACE2 enzyme inhibition of Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare oregano essential oils.
- Origanum majorana should be an essential oil containing 15-30% carvacrol, Origanum minutiflorum containing 70-80% carvacrol, Origanum onites containing 70-85% carvacrol and Origanum vulgare containing 60-70% carvacrol.
- ACE2 enzyme inhibition is since these components are at the specified rates.
- the said pharmaceutically acceptable excipient may be selected from the group consisting of binders, dispersants, diluents, lubricants, brighteners, granulation agents, lubricants, coloring agents, buffering agents, emulsifying agents, solvents, or combinations of two, three or four of them.
- the essential oils were obtained by water-steam distillation.
- the water vapor and volatile components of the dry plant were dragged and collected in a graded burin with the help of a cooler.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Botany (AREA)
- Mycology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Food Science & Technology (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Nutrition Science (AREA)
- Biotechnology (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the ACE-2 enzyme inhibitory effects of essential oils obtained from the aerial parts of the plants Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare.
Description
ACE-2 ENZYME INHIBITORY EFFECTS OF ESSENTIAL OILS OBTAINED FROM THE AERIAL PARTS OF THE PLANTS ORIGANUM MAJORANA, ORIGANUM MINUTIFLORUM, ORIGANUM ONITES AND ORIGANUM VULGARE
Technical Field
The invention relates to the ACE-2 enzyme inhibitory effects of essential oils obtained from the aerial parts, preferably leaves of the plants Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgar e.
State of the Art of the Invention (Prior Art)
Angiotensin-converting enzyme 2, ACE2 in short, is an enzyme bound to the outer surface of cells in the arteries, lungs, kidneys, heart, and intestines. ACE2 accelerates the hydrolysis of the angiotensin II hormone, which is a vasoconstrictor, to angiotensin, thereby reducing blood pressure. ACE-2 enzyme is located in the natural balance of our body and some disorders can be associated with this enzyme.
Especially since December 2019, this enzyme has come to the fore in coronavirus-induced infections, which have caused very serious health problems in the world, and materials that are thought to be effective against coronavirus through ACE-2 enzyme inhibition have been tried and published. ACE2 has been recognized as the specific receptor of the SARS-CoV-2 virus. The strong interaction of the protein S of the SARS-CoV-2 virus and the catalytic region of the ACE2 enzyme is the first step in the formation of the disease. Drug studies for SARS-CoV-2 are still ongoing due to the recent history of the disease, and there are no clear treatments with definite solutions in this regard. Although the effect of some treatments on the virus and the course of the disease has been proven, the detailed analysis continues and this issue remains a serious problem in the world.
Natural resources have become very popular in the treatment of diseases. Products and phytochemicals obtained from plants have been included in the preparations used in the pharmaceutical field from the past to the present. Natural products have attracted special
attention with these effects because the products of plant origin give very good results in the fight against microorganisms. Today, very successful results have started to be obtained from herbal extracts and natural substances.
Muchtaridi Muchtaridi et al. summarizes natural flavonoids that have potential efficacy against COVID-19 through ACE2 receptor inhibition. However, these plants do not include Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare plants and the essential oils thereof.
In their study, Nazim §ekeroglu et al. disclose the antiviral effect of many plants including the species of thyme plant (Origanum vulgare L., Origanum majorana L ). However, it does not disclose that the essential oils obtained from these species show antiviral activity with ACE2 receptor inhibition.
The patent document numbered WO2014/036667 Al describes the method of extracting essential oils from plants, including the Origanum vulgare plant. However, it does not disclose that these essential oils show antiviral activity with ACE2 receptor inhibition.
Brief Description and Objects of the Invention
The primary object of the invention is to obtain essential oils with antiviral effects from the aboveground parts, preferably from the leaves of four different thyme plants, Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare. For this purpose, in vitro experiments including the following steps were performed.
- Analyzing ACE2 enzyme inhibitory effects from the essential oil of Origanum majorana (showing 85.53% ACE2 enzyme inhibition.)
- Analyzing ACE2 enzyme inhibitory effects from the essential oil of Origanum minutiflorum (showing 79.07% ACE2 enzyme inhibition.)
- Analyzing ACE2 enzyme inhibitory effects from the essential oil of Origanum vulgare (showing 74.31% ACE2 enzyme inhibition.)
- Analyzing ACE2 enzyme inhibitory effects from the essential oil of Origanum onites (showing 42.79% ACE2 enzyme inhibition.)
In the invention, essential oils of four different thyme species were investigated in terms of ACE-2 enzyme inhibition. At this point, as a natural agent, these essential oils separately gave very good results in terms of ACE-2 enzyme inhibition at a concentration of 20 micrograms/mL.
The object of the invention is to discover and develop effective, natural and domestic agents against the coronavirus, which is of great importance for human health, by obtaining Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare essential oils.
The pharmaceutical composition obtained by the invention can be used in the preparation of the drug to be used in the treatment of coronavirus disease.
The pharmaceutical composition obtained by the invention can also be used as a supportive treatment in the treatment of coronavirus disease.
Definitions of Figures Describing the Invention
The figures and related descriptions required to better understand the invention are as follows.
Figure 1: % inhibition rate of essential oils of the aboveground parts of Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare against Angiotensinconverting enzyme 2 (ACE2).
Detailed Description of the Invention
The present invention is a pharmaceutical composition and comprises the essential oils of the aerial parts of the oregano species Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare, and has inhibitory effects against the angiotensin-converting enzyme 2 (ACE2).
The pharmaceutical composition of the invention optionally comprises at least one pharmaceutically acceptable excipient.
The invention has shown the effect of high ACE2 enzyme inhibition of Origanum majorana, Origanum minutiflorum, Origanum onites, and Origanum vulgare oregano essential oils.
Origanum majorana should be an essential oil containing 15-30% carvacrol, Origanum minutiflorum containing 70-80% carvacrol, Origanum onites containing 70-85% carvacrol and Origanum vulgare containing 60-70% carvacrol. ACE2 enzyme inhibition is since these components are at the specified rates.
Within the scope of the invention, the said pharmaceutically acceptable excipient may be selected from the group consisting of binders, dispersants, diluents, lubricants, brighteners, granulation agents, lubricants, coloring agents, buffering agents, emulsifying agents, solvents, or combinations of two, three or four of them.
The essential oils were obtained by water-steam distillation. In the Clevenger apparatus, the water vapor and volatile components of the dry plant were dragged and collected in a graded burin with the help of a cooler.
Claims
CLAIMS A pharmaceutical composition, characterized in that it comprises the essential oils of the aerial parts of oregano species Origanum majorana, Origanum minutiflorum, Origanum onites, and/or Origanum vulgare. A composition according to claim 1, characterized in that the essential oil concentration is 20 micrograms/mL. A composition according to claim 1, characterized in that the essential oil of
Origanum majorana contains 15-30% of carvacrol. A composition according to claim 1, characterized in that the essential oil of Origanum minutiflorum contains 70-80% of carvacrol. A composition according to claim 1, characterized in that the essential oil of Origanum vulgare contains 60-70% of carvacrol. A composition according to claim 1, characterized in that the essential oil of Origanum onites contains 70-85% of carvacrol. A composition according to claim 1, characterized in that it is inhibitory against angiotensin-converting enzyme 2 (ACE2). A composition according to claim 1, characterized in that it is used in the preparation of the drug to be used in the treatment of coronavirus disease. A composition according to claim 1, characterized in that it is used as a supportive treatment in the treatment of coronavirus disease.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22813362.5A EP4436560A1 (en) | 2021-11-22 | 2022-10-17 | Ace-2 enzyme inhibitory effects of essential oils obtained from the aerial parts of the plants origanum majorana, origanum minutiflorum, origanum onites and origanum vulgare |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2021018188 | 2021-11-22 | ||
| TR2021/018188 TR2021018188A2 (en) | 2021-11-22 | ACE-2 ENZYME INHIBITORY EFFECTS OF ESSENTIAL OILS OBTAINED FROM THE APRIL PARTS OF ORIGANUM MAJORANA, ORIGANUM MINUTIFLORUM, ORIGANUM ONITES AND ORIGANUM VULGARE PLANTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023091112A1 true WO2023091112A1 (en) | 2023-05-25 |
Family
ID=86397612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/TR2022/051145 WO2023091112A1 (en) | 2021-11-22 | 2022-10-17 | Ace-2 enzyme inhibitory effects of essential oils obtained from the aerial parts of the plants origanum majorana, origanum minutiflorum, origanum onites and origanum vulgare |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2023091112A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014036667A1 (en) | 2012-09-07 | 2014-03-13 | Pontificia Universidad Catolica De Chile | Essential oils from thymus vulgaris (thyme) and origanum vulgare (oregano) and compositions containing same |
-
2022
- 2022-10-17 WO PCT/TR2022/051145 patent/WO2023091112A1/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014036667A1 (en) | 2012-09-07 | 2014-03-13 | Pontificia Universidad Catolica De Chile | Essential oils from thymus vulgaris (thyme) and origanum vulgare (oregano) and compositions containing same |
Non-Patent Citations (4)
| Title |
|---|
| DE CARVALHO FERNANDA OLIVEIRA ET AL: "Would carvacrol be a supporting treatment option effective in minimizing the deleterious effects of COVID-19?", NAUNYN-SCHMIEDEBERG'S ARCHIVES OF PHARMACOLOGY, SPRINGER, DE, vol. 394, no. 12, 20 October 2021 (2021-10-20), pages 2471 - 2474, XP037619280, ISSN: 0028-1298, [retrieved on 20211020], DOI: 10.1007/S00210-021-02170-7 * |
| MARRELLI MARIANGELA ET AL: "Origanumspp.: an update of their chemical and biological profiles", PHYTOCHEMISTRY REVIEWS, KLUWER, NL, vol. 17, no. 4, 30 March 2018 (2018-03-30), pages 873 - 888, XP036571861, ISSN: 1568-7767, [retrieved on 20180330], DOI: 10.1007/S11101-018-9566-0 * |
| PELVAN EBRU ET AL: "Development of propolis and essential oils containing oral/throat spray formulation against SARS-CoV-2 infection", JOURNAL OF FUNCTIONAL FOODS, ELSEVIER BV, NL, vol. 97, 18 August 2022 (2022-08-18), XP087186554, ISSN: 1756-4646, [retrieved on 20220818], DOI: 10.1016/J.JFF.2022.105225 * |
| ZHANG HAIBO ET AL: "Angiotensin-converting enzyme 2 (ACE2) as a SARS-CoV-2 receptor: molecular mechanisms and potential therapeutic target", INTENSIVE CARE MEDICINE, SPRINGER BERLIN HEIDELBERG, BERLIN/HEIDELBERG, vol. 46, no. 4, 3 March 2020 (2020-03-03), pages 586 - 590, XP037077565, ISSN: 0342-4642, [retrieved on 20200303], DOI: 10.1007/S00134-020-05985-9 * |
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