Rosmanol

1 Salvia sp.

NMR, HS-SPME-GC/MS, and HPLC/MS(n) Analyses of Phytoconstituents and Aroma Profile of Rosmarinus eriocalyx.[Pubmed:28657166]

Chem Biodivers. 2017 Oct;14(10).

In this work, a comprehensive study on the chemical constituents of the aerial parts of Rosmarinus eriocalyx (Lamiaceae), an aromatic shrub traditionally consumed as a food and herbal remedy in Algeria, is presented. The aroma profile was analysed by headspace solid phase microextraction (HS-SPME) coupled with gas chromatography-mass spectrometry (GC/MS), whereas the crude extract constituents were analyzed by (1) H-NMR and by high performance liquid chromatography coupled with mass spectrometry (HPLC/MS(n) ). Thirty-nine volatile compounds, most of them being monoterpenes, have been identified, with camphor, camphene, and alpha-pinene as the most abundant constituents. (1) H-NMR analysis revealed the presence of phenolic compounds and betulinic acid while HPLC/MS(n) allowed the identification of glycosilated and aglyconic flavonoids as well as phenylpropanoid derivatives. Some of these constituents, namely as betulinic acid, Rosmanol, and cirsimaritin were reported for the first time in R. eriocalyx.

Diterpenes from rosemary (Rosmarinus officinalis): Defining their potential for anti-cancer activity.[Pubmed:26170168]

Cancer Lett. 2015 Oct 28;367(2):93-102.

Recently, rosemary extracts standardized to diterpenes (e.g. carnosic acid and carnosol) have been approved by the European Union (EU) and given a GRAS (Generally Recognized as Safe) status in the United States by the Food and Drug Administration (FDA). Incorporation of rosemary into our food system and through dietary selection (e.g. Mediterranean Diet) has increased the likelihood of exposure to diterpenes in rosemary. In consideration of this, a more thorough understanding of rosemary diterpenes is needed to understand its potential for a positive impact on human health. Three agents in particular have received the most attention that includes carnosic acid, carnosol, and Rosmanol with promising results of anti-cancer activity. These studies have provided evidence of diterpenes to modulate deregulated signaling pathways in different solid and blood cancers. Rosemary extracts and the phytochemicals therein appear to be well tolerated in different animal models as evidenced by the extensive studies performed for approval by the EU and the FDA as an antioxidant food preservative. This mini-review reports on the pre-clinical studies performed with carnosic acid, carnosol, and Rosmanol describing their mechanism of action in different cancers.

New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts.[Pubmed:25200369]

Fitoterapia. 2014 Dec;99:78-85.

Five new terpenoid glycosides, named as officinoterpenosides A(1) (1), A(2) (2), B (3), C (4), and D (5), together with 11 known ones, (1S,4S,5S)-5-exo-hydrocamphor 5-O-beta-D-glucopyranoside (6), isoRosmanol (7), Rosmanol (8), 7-methoxyRosmanol (9), epiRosmanol (10), ursolic acid (11), micromeric acid (12), oleanolic acid (13), niga-ichigoside F(1) (14), glucosyl tormentate (15), and asteryunnanoside B (16), were obtained from the aerial parts of Rosmarinus officinalis L. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). Among the new ones, 1 and 2, 3 and 4 are diterpenoid and triterpenoid glycosides, respectively; and 5 is a normonoterpenoid. For the known ones, 6 was isolated from the Rosmarinus genus first, and 15, 16 were obtained from this species for the first time.

Determination and Pharmacokinetic Study of Three Diterpenes in Rat Plasma by UHPLC-ESI-MS/MS after Oral Administration of Rosmarinus officinalis L. Extract.[Pubmed:28587218]

Molecules. 2017 Jun 4;22(6). pii: molecules22060934.

Rosmarinus officinalis L. is commonly used as a spice and flavoring agent. Diterpenes are the main active compounds of R. officinalis. An Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry (UHPLC-ESI-MS/MS) method was developed for the determination of carnosol, Rosmanol, and carnosic acid isolated from R. officinalis in rat plasma, and applied to a pharmacokinetic study after oral administration of R. officinalis extract. Sample preparation involved a liquid-liquid extraction of the analytes with ethyl acetate. Butylparaben was employed as an internal standard (I.S.). Chromatographic separation was carried out on a C18 column (ACQUITY UPLC((R)) HSS T3, 1.8 mum, 2.1 mm x 100 mm) with a gradient system consisting of the mobile phase solution A (0.1% formic acid in water) and solution B (acetonitrile) at the flow rate of 0.3 mL/min. The quantification was obtained using multiple reaction monitoring (MRM) mode with electrospray ionization (ESI). The UHPLC-MS/MS assay was validated for linearity, accuracy, precision, extraction recovery, matrix effect and stability. This study described a simple, sensitive and validated UHPLC-MS/MS method for the simultaneous determination of three diterpene compounds in rat plasma after oral administration of R. officinalis extract, and investigated on their pharmacokinetic studies as well.

Relevance of the carnosic acid/carnosol ratio for the level of rosemary diterpene transfer and for improving lamb meat antioxidant status.[Pubmed:24423523]

Food Chem. 2014 May 15;151:212-8.

The aim of the present work was to evaluate whether the relation between the concentrations of the two major diterpenes present in two typified rosemary extracts affects their levels of deposition and antioxidant capacity in different lamb tissues. The composition of the extracts expressed as percentage of weight/weight was 1:1 (14-16)% and 2:1 (25-11)% (carnosic acid-carnosol), respectively. Thirty weaned lambs were assigned randomly to three homogeneous groups. One group was fed a basal diet as a control and the diets of the other two were enriched with rosemary extracts 1:1 and 2:1, respectively. HPLC-ESI-MS/TOF identified a metabolite (C19H22O3) described for the first time in lamb tissues, along with carnosol, carnosic acid, Rosmanol and carnosol-p-quinone. The results obtained corroborate the importance of the presence of carnosol in the dietary administration of rosemary extract as a way of improving the stability of the diterpene fraction during feed manufacturing and the level of deposition and antioxidant efficacy of diterpenes after ruminal fermentation.

[Identification of the chemical compositionsof Verbena officinalis L. extract by high performance liquid chromatography-photodiode array-high resolution mass spectrometry].[Pubmed:29048857]

Se Pu. 2017 Sep 8;35(9):987-994.

To investigate the main chemical compositions of Verbena officinals L. extract, a qualitative high performance liquid chromatography-photodiode array-high resolution mass spectrometry (HPLC-PDA-HRMS) method was established. The structures of the compounds detected were identified by analyzing the chromatographic profiles and the corresponding mass spectra obtained by full scan and MS(n) full scan. Twenty one compounds including iridoid glycosides, flavonoids, triterpenoids, phenylpropanoids and phenolic diterpenoids were identified, and six of them were not reported in other literatures about Verbena officinalis L. extract, such as carnosic acid, carnosol, Rosmanol, isoRosmanol, rosmarinic acid and acacetin-7-O-rutinoside. This method is simple, rapid, accurate and sensitive. It provides a reliable scientific basis for the identification of the authenticity and quality control of Chinese medicinal materials.

Phytochemical Profiling of Flavonoids, Phenolic Acids, Terpenoids, and Volatile Fraction of a Rosemary (Rosmarinus officinalis L.) Extract.[Pubmed:27869784]

Molecules. 2016 Nov 19;21(11). pii: molecules21111576.

This paper presents a comprehensive analysis of the phytochemical profile of a proprietary rosemary (Rosmarinus officinalis L.) extract rich in carnosic acid. A characterization of the (poly)phenolic and volatile fractions of the extract was carried out using mass spectrometric techniques. The (poly)phenolic composition was assessed by ultra-high performance liquid chromatography-electrospray ionization-mass spectrometry (UHPLC-ESI-MS(n)) and a total of 57 compounds were tentatively identified and quantified, 14 of these being detected in rosemary extract for the first time. The rosemary extract contained 24 flavonoids (mainly flavones, although flavonols and flavanones were also detected), 5 phenolic acids, 24 diterpenoids (carnosic acid, carnosol, and Rosmanol derivatives), 1 triterpenoid (betulinic acid), and 3 lignans (medioresinol derivatives). Carnosic acid was the predominant phenolic compound. The volatile profile of the rosemary extract was evaluated by head space solid-phase microextraction (HS-SPME) linked to gas chromatography-mass spectrometry (GC-MS). Sixty-three volatile molecules (mainly terpenes, alcohols, esters, aldehydes, and ketones) were identified. This characterization extends the current knowledge on the phytochemistry of Rosmarinus officinalis and is, to our knowledge, the broadest profiling of its secondary metabolites to date. It can assist in the authentication of rosemary extracts or rosemary-containing products or in testing its bioactivity. Moreover, this methodological approach could be applied to the study of other plant-based food ingredients.

Rosmanol could inhibit the oxidation of low density lipoprotein (LPL) and significantly inhibit lipopolysaccharide induced iNOS and COX-2 expression, with anti-inflammatory effect.

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