Antioxidant activity of lipid-soluble phenolic diterpenes from rosemary
01 Apr 1996-Journal of the American Oil Chemists' Society (Springer-Verlag)-Vol. 73, Iss: 4, pp 507-514
TL;DR: A high-performance liquid chromatography method for analyzing the phenolic diterpenes present in rosemary (Rosmarinus officinalis L.) and commercial rosemary extracts is reported in this article.
Abstract: A high-performance liquid chromatography method for analyzing the phenolic diterpenes present in rosemary (Rosmarinus officinalis L.) and commercial rosemary extracts is reported. Carnosic acid was the major phenolic diterpene present in rosemary leaves, with lesser amounts of 12-methoxycarnosic acid and carnosol. Several commercial rosemary extracts also were analyzed by this method, and in addition to these three compounds other phenolic diterpenes, such as 7-methoxyrosmanol, 7-methoxy-epirosmanol, and rosmanol, were found in some samples. These latter three compounds seem to be artifacts, produced from carnosic acid by oxidation and cyclization. The major phenolic diterpenes were isolated, and their relative antioxidatn activities in soybean oil were measured by the Rancimat. The potency of carnosic acid was more than twice that of any other compound. The antioxidant activity of pure carnosic acid was compared to butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and tertiary butylhydroquinone (TBHQ) and was several times greater than BHT and BHA but less than TBHQ. Nuclear magnetic resonance data for several of the compounds that were incompletely characterized in previous literature are reported.
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TL;DR: An overview of natural antioxidants, their mechanisms of action, and potential applications can be found in this article, where the authors provide an overview of the potential applications of these natural antioxidants.
Abstract: While use of synthetic antioxidants (such as butylated hydroxytoluene and butylated hydroxyanisole) to maintain the quality of ready-to-eat food products has become commonplace, consumer concern regarding their safety has motivated the food industry to seek natural alternatives. Phenolic antioxidants can inhibit free radical formation and/or interrupt propagation of autoxidation. Fat-soluble vitamin E (α-tocopherol) and water-soluble vitamin C (L-ascorbic acid) are both effective in the appropriate matrix. Plant extracts, generally used for their flavoring characteristics, often have strong H-donating activity thus making them extremely effective antioxidants. This antioxidant activity is most often due to phenolic acids (gallic, protocatechuic, caffeic, and rosmarinic acids), phenolic diterpenes (carnosol, carnosic acid, rosmanol, and rosmadial), flavonoids (quercetin, catechin, naringenin, and kaempferol), and volatile oils (eugenol, carvacrol, thymol, and menthol). Some plant pigments (anthocyanin and anthocyanidin) can chelate metals and donate H to oxygen radicals thus slowing oxidation via 2 mechanisms. Tea and extracts of grape seeds and skins contain catechins, epicatechins, phenolic acids, proanthocyanidins, and resveratrol, all of which contribute to their antioxidative activity. The objective of this article is to provide an overview of natural antioxidants, their mechanisms of action, and potential applications.
1,393 citations
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05 Oct 2012
TL;DR: Herbs, spices and their active components as natural antimicrobials in foods Effect of natural antioxidants in herbs and spices on shelf life of foods is studied.
Abstract: Herbs, spices and their active components as natural antimicrobials in foods Effect of natural antioxidants in herbs and spices on shelf life of foods Ajowan Aniseed Asafoetida Allspice Capers and caperberries Caraway Celery Chervil Fennel and fennel seed Galangal Kaffir lime leaf Lavender Lemongrass Lovage Nigella Oregano Poppy Sesame Star anise Tarragon Tamarind Other significant herbs and spices.
682 citations
TL;DR: In this paper, the authors present the results on stabilization of lipids and lipid-containing foods with different herbs and spices (ground materials or extracts) and reports the structure of the main antioxidatively acting compounds isolated from them.
Abstract: There is a growing interest in natural antioxidants found in plants because of the world-wide trend toward the use of natural additives in food and cosmetics. Herbs and spices are one of the most important targets to search for natural antioxidants from the point of view of safety. This review presents the results on stabilization of lipids and lipid-containing foods with different herbs and spices (ground materials or extracts) and reports the structure of the main antioxidatively acting compounds isolated from them. The review presents information about the antioxidative effects of rosemary, sage, oregano, thyme, ginger, summer savory, black pepper, red pepper, clove, marjoram, basil, peppermint, spearmint, common balm, fennel, parsley, cinnamon, cumin, nutmeg, garlic, coriander, etc. Among the herbs of the Labiatae family, rosemary has been more extensively studied and its extracts are the first marketed natural antioxidants. Sage and oregano, which belong to the same family, have gained the interest of many research groups as potential antioxidants.
428 citations
TL;DR: The photoprotection conferred by the xanthophyll cycle and the antioxidant function of tocopherols, lutein and diterpenes may help to avoid irreversible damage in severe drought, making possible the recovery of functional membranes after the autumn rainfalls.
Abstract: Two-year-old rosemary (Rosmarinus officinalis L.) plants were subjected to severe stress by exposure to prolonged drought during a Mediterranean summer. Severely stressed plants recovered completely after the autumn rainfalls although the relative water content remained below 35% for 3 months and the chlorophyll content of leaves was reduced by up to 85% during the drought. In severe stress: (i) α-tocopherol increased 9-fold per g dry weight and 20-fold per unit of chlorophyll; (ii) lutein and β-carotene contents decreased on a dry-weight basis, but an 80% increase in lutein and constant levels of β-carotene were observed on a chlorophyll basis; (iii) there were transient and sustained increases in the de-epoxidation state of the xanthophyll cycle; and (iv) the highly oxidised abietane diterpene isorosmanol increased 8-fold as a result of the oxidation of carnosic acid. With the autumn rainfalls, water status, α-tocopherol and violaxanthin recovered first and the levels of photosynthetic pigments and abietane diterpenes increased later. The photoprotection conferred by the xanthophyll cycle and the antioxidant function of tocopherols, lutein and diterpenes may help to avoid irreversible damage in severe drought, making possible the recovery of functional membranes after the autumn rainfalls. Besides, chlorophyll loss reduces the amount of photons absorbed by leaves, which enhances the photoprotective and antioxidant capacity of leaves per amount of photons absorbed, since the ratios of xanthophylls, α-tocopherol and abietane diterpenes to chlorophyll increase.
400 citations
Cites background from "Antioxidant activity of lipid-solub..."
...Ternes 1992; Richeimer et al. 1996 ) depending on the origin of the plant, its water status and the environmental growth conditions....
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TL;DR: Results indicate high selectivity of the subcritical water toward the most active compounds of rosemary such as carnosol, rosmanol, carnosic acid, methyl carnosate, and some flavonoids such as cirsimaritin and genkwanin.
Abstract: Subcritical water extraction at several temperatures ranging from 25 to 200 °C has been studied to selectively extract antioxidant compounds from rosemary leaves. An exhaustive characterization of the fractions obtained using subcritical water at different temperatures has been carried out by LC-MS, and the antioxidant activities of the extracts have been measured by a free radical method (DPPH). Results indicate high selectivity of the subcritical water toward the most active compounds of rosemary such as carnosol, rosmanol, carnosic acid, methyl carnosate, and some flavonoids such as cirsimaritin and genkwanin. The antioxidant activity of the fractions obtained by extraction at different water temperatures was very high, with values around 11.3 μg/mL, comparable to those achieved by SFE of rosemary leaves. A study of the effect of the temperature on the extraction efficiency of the most typical rosemary antioxidant compounds has been performed. Keywords: Antioxidant activity; antioxidant compounds; rose...
384 citations
References
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TL;DR: Both carnosol and carnosic acid stimulated DNA damage in the bleomycin assay but they scavenged hydroxyl radicals in the deoxyribose assay.
Abstract: 1. Carnosol and carnosic acid have been suggested to account for over 90% of the antioxidant properties of rosemary extract.2. Purified carnosol and carnosic acid are powerful inhibitors of lipid peroxidation in microsomal and liposomal systems, more effective than propyl gallate.3. Carnosol and carnosic acid are good scavengers of peroxyl radicals (CCl3O2) generated by pulse radiolysis, with calculated rate constants of 1–3 × 106M-1 S-1 and 2.7 × 107M-1 S-1 respectively.4. Carnosic acid reacted with HOCl in such a way as to protect the protein α1-antiproteinase against inactivation.5. Both carnosol and carnosic acid stimulated DNA damage in the bleomycin assay but they scavenged hydroxyl radicals in the deoxyribose assay. The calculated rate constants for reaction with ·OH in the deoxyribose system for carnosol and carnosic acid were 8.7 × 1010M-1 and 5.9 × 1010M-1 S-1 respectively.6. Carnosic acid appears to scavenge H2O2, but it could also act as a substrate for the peroxidase system.7. Carnosic acid a...
491 citations
TL;DR: The antioxidant compounds of oleoresin of sage (Salvia officinalis) were separated by column chromatography and high-performance liquid chromatography as discussed by the authors, and the major compounds were identified by IR, MS, and 1 H NMR spectrometry as carnosol, carnosic acid, rosmadial, rosmanol, epirosmanol and methyl carnosate.
Abstract: The antioxidant compounds of oleoresin of sage (Salvia officinalis) were separated by column chromatography and high-performance liquid chromatography. Sir major compounds were purified and identifred by IR, MS, and 1 H NMR spectrometry as carnosol, carnosic acid, rosmadial, rosmanol, epirosmanol, and methyl carnosate. Their antioridative activity was measured with an accelerated test, and their content was quantified in sage and in four commercial rosemary extracts
406 citations
29 Apr 1983
TL;DR: In this article, the authors present a review of the sensory properties of almost 450 Maillard reaction products, with an emphasis on mutagen production and food technology aspects, with emphasis on lysine losses.
Abstract: Various aspects of the Maillard reaction (a non-enzymatic reaction that gives food its flavor and color during frying, roasting, and baking) are discussed for food scientists and nutritionists in 29 technical papers. The papers are organized into 7 sections, covering: historical development; chemical aspects (6 papers); flavors, tastes, and odors of cooked foods (6 papers); food technology aspects (3 papers); nutritional aspects, with emphasis on lysine losses (6 papers); in vivo Maillard reactions (2 papers); and toxicological aspects, with emphasis on mutagen production (5 papers). A literature review of the sensory properties of almost 450 Maillard reaction products is included. (wz)
260 citations
TL;DR: In this article, a reverse-phase high-performance liquid chromatography system was used to quantitate the content of carnosol, carnosic acid and ursolic acid in the rosemary extracts.
Abstract: Rosemary (Rosemarinus officinalis L.) leaves were extracted with three different solvents, namely hexane, acetone and methanol. A reverse-phase high-performance liquid chromatography system in combination with a mass detector was used to quantitate the content of carnosol, carnosic acid and ursolic acid in the rosemary extracts. All rosemary extracts showed strong inhibitory effects on lipid oxidation and soybean lipoxygenase activity.
190 citations
"Antioxidant activity of lipid-solub..." refers background or methods or result in this paper
...There also are several reports that identify the compounds that are chiefly responsible for the antioxidant properties of rosemary extracts and that establish carnosic acid (CA) as the major phenolic diterpene present in fresh rosemary (7,14, 15 ,19-21)....
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...However, commercial and laboratory extraction, bleaching, and deodorization procedures apparently produce additional quantities of CAR and other artifacts, such as rosmanol, epirosmanol, MR, epi-MR, and rosmaridiphenol (4-9,12, 15 )....
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...Several phenolic abietane diterpenes have been isolated from rosemary (4-13) (see Fig. 1), and several reports have been written that address the antioxidant potency of pure compounds and extracts by methods that generally measure the prolongation of induction periods for the onset of rancidity ( 14-19 )....
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...Chen et aL ( 15 ) reported that this method correlated well over a range of temperatures with the active oxygen method....
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...Chen et al. ( 15 ) reported that, in lard, CA had about 1.2 stimes greater activity than CAR in delaying rancidity in the Rancimat....
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