Related Experiment Video
Updated: Jun 13, 2026
09:50
Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Flavonoids and phenolic compounds from Rosmarinus officinalis
Naisheng Bai1, Kan He, Marc Roller
1Naturex, Inc., South Hackensack, New Jersey 07606, USA.
Journal of Agricultural and Food Chemistry
|April 20, 2010
Summary
Rosemary (Rosmarinus officinalis) leaf extracts yielded 15 compounds, including a new flavonoid. Several compounds, particularly carnosic acid and carnosol, demonstrated significant antiproliferative activity against human cancer cell lines and modest anti-inflammatory effects.
Area of Science:
- Phytochemistry
- Natural Products Chemistry
- Pharmacology
Background:
- Rosmarinus officinalis (rosemary) is a widely used herb with a history of medicinal applications.
- Flavonoids and phenolic compounds are known for their diverse biological activities.
- Investigating the chemical constituents of R. officinalis can lead to the discovery of novel therapeutic agents.
Purpose of the Study:
- To isolate and characterize chemical compounds from the leaves of Rosmarinus officinalis.
- To evaluate the cytotoxic effects of isolated compounds against human cancer cell lines.
- To assess the anti-inflammatory potential of these compounds in a macrophage model.
Main Methods:
- Isolation of compounds using chromatographic techniques.
- Structure elucidation employing Nuclear Magnetic Resonance (NMR) spectroscopy and High-Resolution Mass Spectrometry (HRMS).
- Cytotoxicity assays using HepG2, COLO 205, and HL-60 cancer cell lines.
- Anti-inflammatory activity assessment via nitrite production inhibition in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages.
Main Results:
- Fifteen compounds were isolated, including one novel flavonoid, 6''-O-(E)-feruloylhomoplantaginin, and fourteen known compounds.
- Carnosic acid (14) and carnosol (15) exhibited potent antiproliferative activity against HL-60 cells (IC50 values of 1.7 and 5.5 µM, respectively) and COLO 205 cells (IC50 values of 32.8 and 29.9 µM, respectively).
- Compounds 14 and 15 also showed modest anti-inflammatory activity by inhibiting nitrite production in LPS-treated macrophages, alongside compounds 8 (luteolin) and 5 (luteolin 3'-O-beta-D-glucuronide).
Conclusions:
- The study successfully identified and characterized several compounds from Rosmarinus officinalis, highlighting a new flavonoid.
- Carnosic acid and carnosol are promising candidates for further investigation as anticancer agents due to their significant antiproliferative effects.
- The anti-inflammatory properties of these rosemary compounds warrant further research for potential therapeutic applications.
Related Concept Videos
01:17Oxidation of Phenols to Quinones
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
01:25Aromatic Compounds: Overview
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
In 1825, Faraday isolated benzene...
01:20Radical Autoxidation
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
02:59Cancer Prevention
Several factors can increase the risk of cancer in an individual. About 50% of cancer cases can be prevented by adopting a healthy lifestyle, regular exercise, eating healthy, and following a modest cancer prevention diet. Epidemiological studies have consistently shown that populations with vegetable and fruit-rich diets have reduced the incidence of cancer. On the other hand, populations who have a diet rich in animal fat, red meat, junk food, or high calories are predisposed to cancer.
Some...
Some...
02:26Defenses Against Pathogens and Herbivores
Plants present a rich source of nutrients for many organisms, making it a target for herbivores and infectious agents. Plants, though lacking a proper immune system, have developed an array of constitutive and inducible defenses to fend off these attacks.