Rosemary-Derived Drugs and Bioactive Compounds: A Patent Review

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1		Ahmed Fatimi	--	3024	2023-06-30 21:22:57	\|
2	format	Jason Zhu	-1 word(s)	3023	2023-07-03 04:41:04	\|

This entry is adapted from the peer-reviewed paper 10.3390/ddc2010011

Medicinal plants are widely employed in the treatment of human and animal diseases all over the world. Based on their ethnopharmacological uses and applications, the majority of medications are developed from isolated compounds of medicinal plants. Rosemary, one of these medicinal plants, is utilized in medicine due to its analgesic and antibacterial properties. Additionally, it serves as an antioxidant, carminative, and analgesic for muscles and joints, and is employed for the treatment of minor wounds, rashes, headaches, and circulation problems. Furthermore, an ethanolic extract of rosemary has been shown to have antidiabetic activity. Regarding other health pathologies, rosemary has revealed its protective action against types of cancer and cardiovascular diseases.

Rosmarinus officinalis rosemary rosmarinic acid carnosic acid Drugs Natural products

1. Introduction

Medicinal plants are widely employed in the treatment of human and animal diseases all over the world. Based on their ethnopharmacological uses and applications, the majority of current medications are developed from isolated compounds of medicinal plants ^[1]. Rosemary, one of these medicinal plants, is utilized in medicine due to its analgesic and antibacterial properties. Additionally, it serves as an antioxidant, carminative, and analgesic for muscles and joints, and is employed for the treatment of minor wounds, rashes, headaches, and circulation problems ^[2]^[3]^[4]^[5]^[6]. Furthermore, an ethanolic extract of rosemary has been shown to have antidiabetic activity ^[7]. Regarding other health pathologies, rosemary has revealed its protective action against types of cancer and cardiovascular diseases ^[8]^[9].

Historically, botanists identified the species of rosemary as Rosmarinus hortensis angustiore folium. However, in 1753, Carl Linnaeus (or Carl von Linné) formally classified it as Rosmarinus officinalis. As a result, Rosmarinus officinalis Linné (L.) has been widely accepted as a synonym for this plant species ^[10]. Rosmarinus officinalis L. (R. officinalis) is a fragrant, evergreen, perennial shrub with needle-like leaves that can be found growing wild in temperate regions of the Mediterranean such as Morocco, Spain, Portugal, Turkey, and others ^[11]. It is a versatile herb used both in culinary and medicinal practices, and its flowers, stems, and leaves can be extracted to produce essential oils, aromas, and fragrances ^[12]^[13]^[14]. The most commonly used extraction methods to obtain the bioactive compounds from R. officinalis are distillation, hydrodistillation, and supercritical fluid extraction ^[15].

2. Selection of Relevant Patents

This section presents examples of innovation and practical applications of R. officinalis, as evidenced by patents and inventions. The patents described in this section are the most pertinent and noteworthy patents pertaining to R. officinalis between 2002 and 2022, providing a clear understanding of the current status of patents in this field. Thirteen relevant patent documents, including six patent applications and seven granted patents, were selected according to the theory of relevance scoring. Briefly, relevance was based on the query matching score used in Elasticsearch (or Lucene), which uses a Boolean model to find matching documents and a formula called the practical scoring function to calculate relevance ^[16].

Table 1. Summary of relevant patents for R. officinalis between 2002 and 2022.

Patent Number	Document Type ¹	Publication Date	Simple Families	Extended Families	Summary	Ref.
US6391344B2	GP	2002-05-21	4	4	Drug-based rosemary extract useful for the treatment of senile dementia, in particular, Alzheimer’s-type dementia	^[17]
US6638523B1	GP	2003-10-28	2	2	Method of treating ulcers comprising rosemary-derived formulations	^[18]
WO2006/065522A2	PA	2006-06-22	24	27	Oral compositions containing rosemary extracts, which were added to different dentifrice compositions	^[19]
US2007/0053999A1	PA	2007-03-08	39	39	Pharmaceutical compositions for the treatment of cardiovascular and cerebrovascular diseases using rosmarinic acid	^[20]
EP2062899A1	PA	2009-05-27	1	17	Process for the preparation of carnosol from carnosic acid	^[21]
CN102199092A	PA	2011-09-28	1	1	Producing two antioxidant agents from the branches and leaves of R. officinalis	^[22]
US8299034B2	GP	2012-10-30	11	11	Pharmaceutical composition to promote bone growth and maintain bone health with rosemary or caraway extracts	^[23]
WO2014/195291A1	PA	2014-12-11	6	6	Food preservative with antioxidant properties comprising carnosic acid and carnosol from a plant of the Lamiaceae family such as rosemary	^[24]
US9011936B2	GP	2015-04-21	3	3	R. officinalis leaf extracts for pharmaceutical applications	^[25]
CN105777530A	PA	2016-07-20	2	2	Novel process for extracting carnosic acid from R. officinalis	^[26]
CN106860229A	PA	2017-06-20	1	1	Formulation for designing an anti-allergic day cream based on rosemary extract	^[27]
CN111202766A	PA	2020-05-29	1	1	Development of an antiviral drug against pneumonia with a composition based on rosemary extracts	^[28]
US11259488B2	GP	2022-03-01	2	2	Rosemary line rich in carnosic acid up to 9% of dry weight	^[29]

3. Review Based on Relevant Patents

In 2002, Kosaka et al. invented a drug-based rosemary extract useful for the treatment of senile dementia, in particular, Alzheimer’s-type dementia. They aimed to promote the synthesis of nerve growth factor (NGF), which is normally secreted from nerve cells and has an excellent effect on nerve-denaturing diseases. In their granted patent, the inventors claimed a method of promoting the synthesis of nerve growth factor in subjects who need it by using rosemary extract, sage extract, or a mixture of both. The embodiments must contain carnosic acid, carnosol, or both, obtained by extracting rosemary or sage with ethanol or a mixture of water and ethanol. Embodiments can be presented in the form of medicines or food preparations. The in vitro tests presented in the patent description demonstrate that the invented preparations, based on carnosic acid, carnosol, sage extract, or rosemary extract, effectively promote the synthesis of NGF and avoiding the adverse effects of previous drug solutions ^[17].

One year later, Miyazaki et al. invented a method of treating ulcers using rosemary-derived formulations. More specifically, in their granted patent, they described and claimed a method of treating and preventing ulcers (alcoholic ulcers and stress ulcers) by administering sufficient and effective doses of rosemary or sage extracts to a sick person, the active ingredients of which are carnosic acid and carnosol. They proposed using their invention as an oral-consumption drug (e.g., tablet, capsule, or syrup) or as a food supplement. They recommended, on the one hand, favoring carnosic acid and carnosol extracted from rosemary or sage over synthetic products, and, on the other hand, a concentration of active products between 0.1 and 500 mg per kilogram of body weight ^[18].

Another application of rosemary-based extracts concerns dentifrice compositions. For this purpose, Trivedi et al. (2006) proposed an invention for oral compositions containing rosemary extracts, which were added to different dentifrice compositions resulting in toothpaste, mouthwashes, and other compositions. The use of this preparation makes it possible to treat and prevent several oral diseases, such as gingivitis, dental plaque formation, and other similar oral problems. The inventors claimed that the active ingredients of their preparations are ursolic acid and carnosic acid extracted from rosemary. These agents had an antibacterial, antioxidant, and/or anti-inflammatory effect in the oral cavity. Based on other claims, these agents must be present in concentrations ranging from 0.01 to 5% w/w in a mixture containing a humectant, an abrasive material, a fluorine-releasing compound, and an anionic polycarboxylate polymer. To prove the concept, the inventors reported in their patent application the results of two compositions realized through artificial mouth tests. The two compositions tested, using 0.2% w/w rosemary extract, showed improved anti-plaque efficacy, respectively, by 53 and 54% compared to the negative control. The same proposed compositions, formulated with 0.3% w/w of rosemary extract, show improved antioxidant efficacy compared to a negative control in a lipid peroxide assay. The optical densities of the two embodiments were, respectively, about 0.72 and 0.74, compared to 0.81 for the control. It was shown that the anti-inflammatory efficacy and effect against gingivitis of certain embodiments based on rosemary extract were enhanced by the addition of an antibacterial agent such as triclosan ^[19].

In 2007, a patent application for pharmaceutical compositions for the treatment of cardiovascular and cerebrovascular diseases was filed. Through this application, Wei et al. described and claimed the development of a medicinal composition using plant extracts. The invention was based particularly on different plants used in traditional Chinese medicine. Among the claimed pharmaceutical compositions, an extract based on rosmarinic acid was used in the formulation, and in vivo tests in rats were conducted to prove the concept for the treatment of cardiovascular and cerebrovascular diseases. The proposed drug compositions showed significant therapeutic effects. They induced a significant decrease in neurological symptoms as well as a reduction in the area of cerebral infarction compared to the control rat group. The same compositions showed better effects than positive controls using commercial drugs ^[20].

Two years later, Wehrli developed a process for the preparation of carnosol from carnosic acid. The inventor reported that rosemary or sage extracts contain between 10 and 30% carnosic acid, which can be converted into carnosol, a biologically active form of polyphenol known for its antioxidant action and presumed anti-carcinogenicity. The invented process has the advantage of being easy and effective, in which the first oxidation transforms carnosic acid into quinone, which is then converted into carnosol. The catalyst can be iron or an iron salt, a small amount of water, rosemary needles, or mixtures thereof. The final product of the invented process was carnosol mixed with reaction by-products. The inventor finally described that embodiments may be nutritional as food supplements or pharmaceutical as different galenical preparations (i.e., solid or liquid) for human or animal use ^[21].

The antioxidant activity of R. officinalis was highlighted in a patent application proposed by Xie et al. (2011) ^[22]. The invention focused on technology for producing two antioxidant agents from the branches and leaves of R. officinalis. More specifically, it concerned pharmacological data attesting to the multiple beneficial effects of the agents targeted by this new technique, namely, diterpene phenols (including carnosic acid), which have antioxidant, antitumor, and anti-HIV effects. Effects of rosmarinic acid, among which are its analgesic, anti-inflammatory, antioxidant, antithrombotic, and fibrinolytic activities, were reported. Furthermore, the innovation was characterized by the use of counter-current ultrasound as an extraction method. The extracted liquid, whose solid/liquid ratio was between 1:10 and 1:30, was separated for 30 min by a system of membrane sieves at a temperature ranging from 15 to 65 °C and with the addition of 30 to 85% ethanol, to obtain a fat-soluble component mainly formed by carnosic acid and a water-soluble component mainly formed by rosmarinic acid. This technology for the production of rosemary extracts has the advantages of simplicity, low energy consumption, production efficiency, and safety, due to the homogeneity of the extracted components ^[22].

Another medical application of rosemary extracts was published in 2012. The granted patent was for the use of extracts of aromatic and medicinal plants, including rosemary, for the health benefits of their constituents. The invention by Offord Cavin et al. was a pharmaceutical composition to promote bone growth and maintain bone health with rosemary or caraway extracts. The scientific background in the description of the invention reports that the bone renewal process, and thus bone density, are genetically regulated in humans. According to the inventors, the patent claims were based on the introduction of a phytochemical having the ability to induce genetic expression of a bone morphogenic protein using one or more polyphenols among feruloylnepitrin, foumaroylnepitrin, dehydroxyrosmarinic acid, eupafoline, carnosol, scutellarin, gencwanine, kaempferol, and acacetin. The product may be presented in the form of a medicinal or food preparation, and can be administered orally and/or enterally. Active plant agents can be mixed with a protein source, a fat source, and/or a carbohydrate source. The invention also claims the ability to maintain bone health and prevent bone disorders, as well as their relief and/or treatment. The preparations based on the invented composition act through the inhibition of bone resorption, and thus participate in maintaining adequate bone density in the elderly and after the advent of menopause in women ^[23].

The antioxidant activity of R. officinalis was highlighted in another patent application published in 2014. The invention concerned an antioxidant composition that can be used as a food preservative of natural origin and is therefore a good substitute for poorly perceived chemical antioxidants. Indeed, the background reported in the description of the patent application insists on the importance of developing natural, economical, and effective food preservatives to meet the demand of the food industry. For this purpose, Torben et al. proposed a composition (e.g., an emulsion-based food) based on two plant extracts, one comprising carnosic acid and carnosol from a plant of the Lamiaceae family such as rosemary or sage, and the other comprising pregnane glycosides obtained from a plant of the genus Caralluma. These two compounds can be mixed beforehand for direct use or separated as a kit from the two components to be mixed when used with adequate dosage. The invented composition is intended to inhibit the oxidation of foodstuffs. Its proposed applications are multiple, including but not limited to the protection of raw or cooked foods such as meat, seafood, pasta sauces, pasteurized soups, mayonnaise, salad dressings, oil-in-water emulsions, and various dairy products. Furthermore, this antioxidant composition was also proposed as consumable by pets in the form of a supplement or food constituent ^[24].

As mentioned in the introduction, R. officinalis is able to produce bioactive compounds by extraction from flowers, stems, or leaves. In this regard, He et al. proposed, through a patent application published in 2015, an invention that highlighted R. officinalis leaf extracts for pharmaceutical applications. This invention exploits the properties of the active constituents of rosemary to reduce important health problems such as type II diabetes, obesity, and cardiovascular disease. More specifically, the claimed composition consists of about 40 to 65% w/w carnosic acid, about 2 to 10% w/w carnosol, and about 2 to 10% w/w 12-O-methylcarnosic acid. It allows the sick person to attain noticeable improvements. This pharmaceutical composition makes it possible to reduce the oxidation of low-density lipoproteins in cases of cholesterol-related disorders, increase the activity of a receptor activated by a peroxisome proliferator involved in lipid metabolism and energy homeostasis, inhibit the activity of pancreatic lipase, decrease fasting blood glucose, reduce fasting plasma insulin levels in diabetic people, and reduce weight and body fat in individuals suffering from or at risk of obesity. The results of in vivo experiments in mice were reported to confirm the efficacy of the invention. Mice fed for 16 weeks with a diet rich in fat and treated with the invented composition based on rosemary extract dosed with 50% w/w carnosic acid showed statistically lower blood glucose than a positive control of mice fed with a similar rich diet without administration of the invented composition. The sacrifice of these mice allowed the determination of their amount of fat, and a considerable decrease in fat mass was noted in treated mice compared to control mice. In vitro results were also reported. The inhibition effect of pancreatic lipase on the invented composition, dosed at 20% w/w carnosic acid, was compared with that of a commercially recognized drug. The assay revealed that the invented composition had significant pancreatic inhibitory activity, confirming its utility in the treatment of obesity ^[25].

As described above, several inventions have been concerned with extracting and purifying bioactive compounds from plants, including rosemary. In 2016, Lin et al. developed a novel process for extracting carnosic acid from R. officinalis. The description of the invention reports the benefits of carnosic acid, in particular the effect of reducing weight and body lipids, the prevention of cardiovascular disease, and an antitumor effect. In this patent application, the inventors claimed a method of extracting carnosic acid from dried and powdered rosemary leaves. The method described involved the filtration of rosemary powder in several steps with an ethanol solution of 85–95% v/v for a period of between 1 and 2 h at a temperature ranging from 78 to 80 °C. Carnosic acid was then obtained following the crystallization of the filtrate. The method invented aimed to overcome the problems found during the examination of the prior art. This invention has the advantage of reducing the cost of production through a simple and fast process that exploits a large part of the plant. This new process claims high product purity and adaptability to large-scale industrial production ^[26].

In 2017, Yan developed a formulation for designing an anti-allergic day cream based on rosemary extract. This invention confirmed another pharmaceutical application of R. officinalis. The description provided in the application addressed the problem of aggression suffered by skin cells in the external environment. In some cases of allergies and weak immune reactions, damaged skin is not repaired, causing accelerated aging of the skin. According to patent claims, the invented rosemary-based cream offered a skin preparation using a formulation that incorporates 1.3% by weight of rosemary extract. In some embodiments, this preparation had a relaxing and moisturizing anti-inflammatory effect on the skin and limited problems of spots, eczema, wrinkles, and allergies ^[27].

The development of an antiviral drug against pneumonia with a composition based on rosemary extracts was confirmed through a patent application published in 2020. The active agents of this drug composition were rosmarinic acid, carnosic acid, and carnosol, with a mass ratio of 1:3:5, respectively. Although the production of antiviral drugs from plants is a promising research method, Hu et al. explained that the goal of the invention was to develop an antiviral against pneumonia using a simple method for the first time. Furthermore, the invention description reported test results of the invented composition that reduces the ratio of lung weight to wet weight of tissues, reduces the total content of proteins in the lungs, inhibits serum release, and regulates the release of cytokines involved in the immune response inflammation, which relieves damage due to infection. The results also showed a clear inhibition of H3N2 influenza virus replication in the lungs ^[28].

Carnosic acid can be extracted from rosemary and could play a key role as an antioxidant in food or animal foods, as well as in care products. However, wild-type rosemary contains only about 2 to 3% w/w of this acid. Following a long clonal breeding program, a patent application concerning rosemary’s high carnosic acid was published in 2022. Narasimhamoorthy et al. claimed a rosemary line rich in carnosic acid up to 9% w/w of its dry weight, obtained following a series of selective clonings made from existing rosemary by self-pollination or cross-pollination. The invention description provided in the patent stated that no line with such characteristics has ever been observed in nature. From the cultivar line, a node or cutting can be used to grow identical plants that have, in addition to the richness of carnosic acid, promising agronomic characteristics such as robustness, stability, and high production of biomass, which increase the yield of carnosic acid ^[29].

References

Andrade, J.M.; Faustino, C.; Garcia, C.; Ladeiras, D.; Reis, C.P.; Rijo, P. Rosmarinus officinalis L.: An update review of its phytochemistry and biological activity. Future Sci. OA 2018, 4, 283.
Sagor, A.T.M.; Reza, M.H.; Tabassum, N.; Sikder, B.; Ulla, A.; Subhan, N.; Hossain, H.M.; Alam, A.M. Supplementation of Rosemary Leaves (Rosmarinus officinalis) Powder Attenuates Oxidative Stress, Inflammation and Fibrosis in Carbon Tetrachloride (CCl4) Treated Rats. Curr. Nutr. Food Sci. 2016, 12, 288–295.
Rašković, A.; Milanović, I.; Pavlović, N.; Ćebović, T.; Vukmirović, S.; Mikov, M. Antioxidant activity of rosemary (Rosmarinus officinalis L.) essential oil and its hepatoprotective potential. BMC Complement. Altern. Med. 2014, 14, 225.
Wang, W.; Li, N.; Luo, M.; Zu, Y.; Efferth, T. Antibacterial Activity and Anticancer Activity of Rosmarinus officinalis L. Essential Oil Compared to That of Its Main Components. Molecules 2012, 17, 2704–2713.
Jiang, Y.; Wu, N.; Fu, Y.-J.; Wang, W.; Luo, M.; Zhao, C.-J.; Zu, Y.-G.; Liu, X.-L. Chemical composition and antimicrobial activity of the essential oil of Rosemary. Environ. Toxicol. Pharmacol. 2011, 32, 63–68.
Peng, C.-H.; Su, J.-D.; Chyau, C.-C.; Sung, T.-Y.; Ho, S.-S.; Peng, C.-C.; Peng, R.Y. Supercritical fluid extracts of rosemary leaves exhibit potent anti-inflammation and anti-tumor effects. Biosci. Biotechnol. Biochem. 2007, 71, 2223–2232.
Malek, A.; Sadaka, W.M.M.; Hamo, S.; Al-Mahbashi, M.H. Evaluation of Antidiabetic Activity of Rosmarinus officinalis var. prostratus Growing in Syria in Alloxan Diabetic Rats. Curr. Bioact. Compd. 2021, 17, 187–193.
Sánchez-Camargo, A.d.P.; Herrero, M. Rosemary (Rosmarinus officinalis) as a functional ingredient: Recent scientific evidence. Curr. Opin. Food Sci. 2017, 14, 13–19.
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Kosaka, K.; Miyazaki, T.; Ito, H. Method of Promoting Synthesis of Nerve Growth Factor. Granted Patent US6391344B2, 21 May 2002.
Miyazaki, T.; Kosaka, K.; Ito, H. Method of Treating Ulcers. Granted Patent US6638523B1, 28 October 2003.
Trivedi, H.M.; Xu, T.; Worrell, C.L.; Panaligan, K. Oral Compositions Containing Extracts of Rosmarinus and Related Methods. Patent Application WO2006065522A2, 22 June 2006.
Wei, F.; Li, D.; Luo, C.; Yue, H.; Chen, Q.; Huang, Z. Pharmaceutical Composition for the Treatment of Cardiovascular and Cerebrovascular Diseases. Patent Application US20070053999A1, 8 March 2007.
Wehrli, C. Process for Producing Carnosol from Carnosic Acid. Patent Application EP2062899A1, 27 May 2009.
Xie, K.; Zhang, M.; Fan, Y. Production Technology for Acquiring Two Antioxidant Agents from Rosmarinus officinalis L. Patent Application CN102199092A, 28 September 2011.
Offord Cavin, E.; Williamson, G.; Courtois, D.; Lemaure, B.; Touche, A.; Soon Grace, I.N.G.; Ameye, L. Nutritional Compositions for Promotion of Bone Growth and Maintenance of Bone Health Comprising Extracts of for Example Rosemary or Caraway. Granted Patent US8299034B2, 30 October 2012.
Torben, I.; Lars, M.; Jørn, M.; Niels, C. Antioxidant Composition. Patent Application WO2014195291A1, 11 December 2014.
He, K.; Roller, M.; Ibarra, A.; Bai, N.; Dikansky, J. Extract of Rosmarinus officinalis L. leaves for Pharmaceutical Applications. Granted Patent US9011936B2, 21 April 2015.
Lin, T.; Li, J. Method for Extracting Carnosic Acid from Rosmarinus Officinalis. Patent Application CN105777530A, 20 July 2016.
Yan, C. Preparation Method of Enzyme Anti-Allergic Day Cream. Patent Application CN106860229A, 20 June 2017.
Hu, W.; Zhang, R.; Yu, J.; Yu, H.; Zhang, L.; Zhao, R. Application of Rosemary Extract in Antiviral Pneumonia Medicine. Patent Application CN111202766A, 29 May 2020.
Narasimhamoorthy, B.; Greaves John, A.; Zhao, L.; Qiu, Z.; Cox, J.; Baker, J. Rosemary (Rosmarinus officinalis L.) with High Carnosic Acid Denominated KI937. Granted Patent US11259488B2, 1 March 2022.

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Ahmed Fatimi

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1. Introduction

2. Selection of Relevant Patents

3. Review Based on Relevant Patents

References