WO2023128989A1 - Inhibitory effects of standardized extracts of rosmarinus officinalis leaves on cox-1, cox-2 and lox enzymes - Google Patents
Inhibitory effects of standardized extracts of rosmarinus officinalis leaves on cox-1, cox-2 and lox enzymes Download PDFInfo
- Publication number
- WO2023128989A1 WO2023128989A1 PCT/TR2022/051139 TR2022051139W WO2023128989A1 WO 2023128989 A1 WO2023128989 A1 WO 2023128989A1 TR 2022051139 W TR2022051139 W TR 2022051139W WO 2023128989 A1 WO2023128989 A1 WO 2023128989A1
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- Prior art keywords
- cox
- rosmarinus officinalis
- rosmarinic acid
- officinalis leaves
- extract
- Prior art date
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- 239000000284 extract Substances 0.000 title claims abstract description 32
- 241001530490 Salvia rosmarinus Species 0.000 title claims abstract description 24
- 235000015639 rosmarinus officinalis Nutrition 0.000 title claims abstract description 24
- 102000004190 Enzymes Human genes 0.000 title claims description 4
- 108090000790 Enzymes Proteins 0.000 title claims description 4
- 101100496968 Caenorhabditis elegans ctc-1 gene Proteins 0.000 title claims 2
- 101100221647 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cox-1 gene Proteins 0.000 title claims 2
- 101150062589 PTGS1 gene Proteins 0.000 title claims 2
- 230000002401 inhibitory effect Effects 0.000 title description 2
- 101150071146 COX2 gene Proteins 0.000 title 1
- 101100114534 Caenorhabditis elegans ctc-2 gene Proteins 0.000 title 1
- 101150000187 PTGS2 gene Proteins 0.000 title 1
- 101150070593 lox gene Proteins 0.000 title 1
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 claims abstract description 50
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 claims abstract description 25
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 claims abstract description 25
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229940121363 anti-inflammatory agent Drugs 0.000 claims abstract description 24
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 24
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 7
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 5
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229960001259 diclofenac Drugs 0.000 claims description 3
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 3
- 229960001680 ibuprofen Drugs 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 238000009472 formulation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 5
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 239000007942 layered tablet Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006191 orally-disintegrating tablet Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- -1 sachet Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
Definitions
- the present invention relates to a standardized extract of Rosmarinus officinalis L. leaves over rosmarinic acid for use as an anti-inflammatory agent.
- the inventors aim to develop anti-inflammatory agents derived from herbal or natural sources, which can be standardized in terms of the amount of pharmaceutically active substances contained therein.
- the present invention is directed to a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent or to compounds comprising rosmarinic acid in any proportion, for example, 0.5% - 99%, preferably plant extracts comprising 0.5% - 99% rosmarinic acid, in particular preferably Rosmarinus officinalis leaves extracts comprising 0.5% - 95% rosmarinic acid, for example, Rosmarinus officinalis leaves extracts comprising 0.5% - 2% rosmarinic acid.
- a natural anti-inflammatory agent is provided to patients with a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent according to the invention.
- the present invention is directed to a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent.
- Another embodiment of the invention is directed to a standardized extract of Rosmarinus officinalis leaves comprising at least 0.5%, preferably 0.5-2% rosmarinic acid for use as an anti-inflammatory agent.
- the amount of % rosmarinic acid mentioned in the scope of the invention is determined by any method of analysis used in the determination of rosmarinic acid in the extract of Rosmarinus officinalis leaves, for example, HPLC and/or HPTLC device analysis, according to the Turkish Pharmacopoeia-II monographs (European pharmacopeia adaptation) - 2016 (Ministry of Health of Republic of Turkey, Turkish Medicines and Medical Devices Agency, I. Edition, 2016).
- anti-inflammatory agent used here includes agents that show the effect as COX-1 and/or COX-2 and/or LOX inhibitors.
- the ratio % mentioned in the context of the present invention is a relative ratio and refers to the amount of rosmarinic acid compared to the total amount of substance in the Rosmarinus officinalis leaves extract sample subjected to analysis. For example, if the area of the entire peak obtained in the HPLC analysis of the Rosmarinus officinalis leaves extract sample is expressed as 100, the area of the peak corresponding to rosmarinic acid in Rosmarinus officinalis leaves extract sample according to the invention should be at least 0.5.
- the invention relates to pharmaceutical compositions comprising a standardized extract of Rosmarinus officinalis leaves suitable for use as an anti-inflammatory agent comprising at least 0.5%, preferably in the range of 0.5-2% rosmarinic acid.
- Another aspect of the invention is the use of another anti-inflammatory agent in addition to the said active ingredient in pharmaceutical compositions comprising a standardized extract of Rosmarinus officinalis leaves comprising at least 0.5%, preferably 0.5-2%, rosmarinic acid as the active ingredient.
- said additional anti-inflammatory agents may be ibuprofen or diclofenac.
- Combinations according to the invention may be formulated in the same dosage form or different dosage forms.
- the combination formulations according to the invention are formulated in different dosage forms, the said formulations may be used at different times or simultaneously or sequentially.
- Formulations according to the invention may be formulated in a dosage form suitable for oral or topical use.
- Oral formulations may be in any of the forms of tablet, capsule, extended- release capsule, delayed-release capsule, syrup, emulsion, suspension, coated tablet, layered tablet, orally disintegrating tablet, effervescent tablet, sachet, sublingual tablet.
- Topical formulations may be in any of the forms of ointment, cream, gel, hydrogel, or lotion.
- Formulations according to the invention may comprise at least one pharmaceutically acceptable excipient in addition to the extract of Rosmarinus officinalis leaves comprising at least 0.5% rosmarinic acid.
- Said excipient may not have any therapeutic effect but may be used to fulfill a requirement arising during the preparation or preservation or use of the formulation.
- agents of natural origin suitable for use as anti-inflammatory agents have been developed.
- the invention is of interest to both end-users in the healthcare sector and drug developers. Examples
- Example 1 IC50 values for COX-1 and COX-2 inhibition of Rosmarinus officinalis leaves extract according to the invention and comparison thereof with known anti-inflammatory agents
- Rosmarinus officinalis leaves extract used in the study whose results are given below comprises 0.8% rosmarinic acid.
- Example 1 When the results in Example 1 are evaluated, it is seen that the standardized extract of Rosmarinus officinalis leaves according to the invention over rosmarinic acid shows better or significantly close anti-inflammatory effect than anti-inflammatory agents used commercially for a long time, although it is a natural extract.
- the anti-inflammatory effect mentioned here is shown through COX-1 and/or COX-2 inhibition.
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- 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)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent.
Description
INHIBITORY EFFECTS OF STANDARDIZED EXTRACTS OF
ROSMARINUS OFFICINALIS L. LEAVES ON COX-1, COX-2 AND LOX ENZYMES
Technical Field
The present invention relates to a standardized extract of Rosmarinus officinalis L. leaves over rosmarinic acid for use as an anti-inflammatory agent.
State of the Art
Diseases caused by inflammation are frequently encountered. Inflammations that occur in different parts of the body for different reasons are tried to be treated with various conventional drugs. However, treatment with these agents is sometimes inadequate and the discovery of novel and natural anti-inflammatory agents is of great importance.
One of the most common problems in the commercial use of therapeutic agents of natural origin is that the amount of pharmaceutically active substances in the extracts obtained from natural products is not constant. The variation in this amount, which may vary depending on the region or period of collection of the plant, prevents the development of reproducible and standardizable formulations using plant-based extracts.
Considering the state of the art, it is obvious that there is a need for pharmaceutical quality anti-inflammatory agents that can be both obtained from herbal or natural sources and standardized in terms of the amount of substances that show pharmaceutical activity.
Aim of the Invention
The inventors aim to develop anti-inflammatory agents derived from herbal or natural sources, which can be standardized in terms of the amount of pharmaceutically active substances contained therein.
Brief Description of the Invention
The present invention is directed to a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent or to compounds comprising rosmarinic acid in any proportion, for example, 0.5% - 99%, preferably plant extracts
comprising 0.5% - 99% rosmarinic acid, in particular preferably Rosmarinus officinalis leaves extracts comprising 0.5% - 95% rosmarinic acid, for example, Rosmarinus officinalis leaves extracts comprising 0.5% - 2% rosmarinic acid.
Since the standardized extracts in terms of rosmarinic acid are used in the invention, the results of the study are reproducible and debatable.
Furthermore, since there are not many agents that selectively inhibit COX and LOX enzymes, a natural anti-inflammatory agent is provided to patients with a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent according to the invention.
Detailed Description of the Invention
The present invention is directed to a standardized extract of Rosmarinus officinalis leaves over rosmarinic acid for use as an anti-inflammatory agent.
Another embodiment of the invention is directed to a standardized extract of Rosmarinus officinalis leaves comprising at least 0.5%, preferably 0.5-2% rosmarinic acid for use as an anti-inflammatory agent.
The amount of % rosmarinic acid mentioned in the scope of the invention is determined by any method of analysis used in the determination of rosmarinic acid in the extract of Rosmarinus officinalis leaves, for example, HPLC and/or HPTLC device analysis, according to the Turkish Pharmacopoeia-II monographs (European pharmacopeia adaptation) - 2016 (Ministry of Health of Republic of Turkey, Turkish Medicines and Medical Devices Agency, I. Edition, 2016).
The term anti-inflammatory agent used here includes agents that show the effect as COX-1 and/or COX-2 and/or LOX inhibitors.
The ratio % mentioned in the context of the present invention is a relative ratio and refers to the amount of rosmarinic acid compared to the total amount of substance in the Rosmarinus officinalis leaves extract sample subjected to analysis. For example, if the area of the entire peak obtained in the HPLC analysis of the Rosmarinus officinalis leaves extract sample is expressed as 100, the area of the peak corresponding to rosmarinic acid in Rosmarinus officinalis leaves extract sample according to the invention should be at least 0.5.
In a further aspect, the invention relates to pharmaceutical compositions comprising a standardized extract of Rosmarinus officinalis leaves suitable for use as an anti-inflammatory agent comprising at least 0.5%, preferably in the range of 0.5-2% rosmarinic acid.
Another aspect of the invention is the use of another anti-inflammatory agent in addition to the said active ingredient in pharmaceutical compositions comprising a standardized extract of Rosmarinus officinalis leaves comprising at least 0.5%, preferably 0.5-2%, rosmarinic acid as the active ingredient.
In one embodiment of the invention, said additional anti-inflammatory agents may be ibuprofen or diclofenac.
Combinations according to the invention may be formulated in the same dosage form or different dosage forms.
If the combination formulations according to the invention are formulated in different dosage forms, the said formulations may be used at different times or simultaneously or sequentially.
Formulations according to the invention may be formulated in a dosage form suitable for oral or topical use. Oral formulations may be in any of the forms of tablet, capsule, extended- release capsule, delayed-release capsule, syrup, emulsion, suspension, coated tablet, layered tablet, orally disintegrating tablet, effervescent tablet, sachet, sublingual tablet. Topical formulations may be in any of the forms of ointment, cream, gel, hydrogel, or lotion.
Formulations according to the invention may comprise at least one pharmaceutically acceptable excipient in addition to the extract of Rosmarinus officinalis leaves comprising at least 0.5% rosmarinic acid. Said excipient may not have any therapeutic effect but may be used to fulfill a requirement arising during the preparation or preservation or use of the formulation.
Industrial Applicability
Thanks to the invention, agents of natural origin suitable for use as anti-inflammatory agents have been developed.
In this respect, the invention is of interest to both end-users in the healthcare sector and drug developers.
Examples
Example 1 : IC50 values for COX-1 and COX-2 inhibition of Rosmarinus officinalis leaves extract according to the invention and comparison thereof with known anti-inflammatory agents
Rosmarinus officinalis leaves extract used in the study whose results are given below comprises 0.8% rosmarinic acid.
When the results in Example 1 are evaluated, it is seen that the standardized extract of Rosmarinus officinalis leaves according to the invention over rosmarinic acid shows better or significantly close anti-inflammatory effect than anti-inflammatory agents used commercially for a long time, although it is a natural extract. The anti-inflammatory effect mentioned here is shown through COX-1 and/or COX-2 inhibition. The better COX-1 and COX-2 inhibition compared to ibuprofen and diclofenac, which have been frequently used anti-inflammatory agents in the pharmaceutical market for many years, suggests that these natural standardized extracts may be important anti-inflammatory agents.
Furthermore, it can be seen from the table above that the standardized extract of Rosmarinus officinalis leaves according to the invention over rosmarinic acid is more effective on COX-2, and that this extract according to the invention does not have the stomach irritant effect often seen in some anti-inflammatory agents. In this respect, the standardized extracts according to the invention are superior to the agents available in the known art.
Claims
1. Standardized extract of Rosmarinus officinalis leaves comprising at least 0.50% rosmarinic acid for use as an anti-inflammatory agent.
2. The standardized extract of Rosmarinus officinalis leaves comprising at least 0.50% rosmarinic acid for use as an inhibitor of COX- 1 and/or COX-2 and/or LOX enzyme according to claim 1.
3. An extract according to claims 1 or 2, comprising rosmarinic acid in the range of 0.50-2%.
4. Pharmaceutical compositions comprising a standardized extract of Rosmarinus officinalis leaves comprising at least 0.50% rosmarinic acid as the active ingredient, suitable for use as an anti-inflammatory agent.
5. A pharmaceutical composition according to claim 4, further comprising another antiinflammatory agent.
6. A pharmaceutical composition according to claim 5, wherein the additional antiinflammatory agent is diclofenac or ibuprofen.
7. A pharmaceutical composition according to any one of claims 4-6, formulated in a dosage form suitable for oral or topical use.
5
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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TR2021021391 | 2021-12-28 | ||
TRTR2021/021391 | 2021-12-28 |
Publications (1)
Publication Number | Publication Date |
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WO2023128989A1 true WO2023128989A1 (en) | 2023-07-06 |
Family
ID=87000144
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Application Number | Title | Priority Date | Filing Date |
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PCT/TR2022/051139 WO2023128989A1 (en) | 2021-12-28 | 2022-10-17 | Inhibitory effects of standardized extracts of rosmarinus officinalis leaves on cox-1, cox-2 and lox enzymes |
Country Status (1)
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WO (1) | WO2023128989A1 (en) |
-
2022
- 2022-10-17 WO PCT/TR2022/051139 patent/WO2023128989A1/en unknown
Non-Patent Citations (5)
Title |
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BEGUM NASREEN, SRISAILAM K., MAHESHWAR UMA RAO V.: "Investigation of in vitro anti-inflammatory and COX-2 inhibitory activities of Rosmarinus officinalis", JOURNAL OF CHEMICAL AND PHARMACEUTICAL RESEARCH, JAIPUR: JOURNAL OF CHEMICAL AND PHARMACEUTICAL RESEARCH, IN, vol. 8, no. 4, 1 January 2016 (2016-01-01), IN , pages 327 - 331, XP093078327, ISSN: 0975-7384 * |
LUO CHUNXU, ZOU LIN, SUN HUIJUN, PENG JINYONG, GAO CONG, BAO LIUCHI, JI RENPENG, JIN YUE, SUN SHUANGYONG: "A Review of the Anti-Inflammatory Effects of Rosmarinic Acid on Inflammatory Diseases", FRONTIERS IN PHARMACOLOGY, vol. 11, XP093078324, DOI: 10.3389/fphar.2020.00153 * |
MAKALESI ARAŞTIRMA, YANIT YÜZEY, ILE METODOLOJISI, YAPRAKLARINDAN BIBERIYE, ASIT ROSMARINIK, OPTIMIZASYONU EKSTRAKSIYONUNUN, BULDU: "Optimization of Rosmarinic Acid Extraction from Rosemary Leaves by Surface Response Methodology", vol. 5, no. 2, 31 July 2017 (2017-07-31), pages 441 - 454, XP093078321 * |
NACIYE ERKAN ET AL.: "Antioxidant activities of rosemary (Rosmarinus Officinalis L.) extract, blackseed (Nigella sativa L.) essential oil, carnosic acid, rosmarinic acid and sesamol", FOOD CHEMISTRY, vol. 110, no. 1, 2008, pages 76 - 82, XP029231755, ISSN: 0308-8146, DOI: 10.1016/j.foodchem. 2008.01.05 8 * |
SCHECKEL KRISTEN A., DEGNER STEPHANIE C., ROMAGNOLO DONATO F.: "Rosmarinic Acid Antagonizes Activator Protein-1–Dependent Activation of Cyclooxygenase-2 Expression in Human Cancer and Nonmalignant Cell Lines", THE JOURNAL OF NUTRITION, AMERICAN SOCIETY FOR NUTRITION, US, vol. 138, no. 11, 1 November 2008 (2008-11-01), US , pages 2098 - 2105, XP093078323, ISSN: 0022-3166, DOI: 10.3945/jn.108.090431 * |
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