Davana Oil Research Articles

Artemisia pallens Wall. ex. DC: A comprehensive review

Davana (Artemisia pallens Wall. ex DC) is a well-known and precious essential oil-bearing plant under the family Compositae (Asteraceae). It is an erectly grown herbaceous plant exclusively cultivated as a short-term crop in south India during winter. It is distributed in the northern hemisphere in subtropical Africa, South Africa, West America, and South America; however, it is indigenous to southern India. The yearly productivity of davana oil typically falls between 8 to 10 tones. Davana oil is mainly used to flavor pastries, cakes, tobacco, and some beverages. It consists of diverse phyto-molecules and is an important and unique commodity in the fragrance, flavor, and liquor industries. It has excellent biological potential and contains volatile and nonvolatile constituents such as terpenoids, flavonoids, and alkaloids, which have high pharmacological values. Several investigations have focused on validating the importance of chemical constituents and the biological efficacy of essential oils and various extracts in multiple industries. The review focuses on the complete agronomic practices, botany, breeding, biotechnology, and chemistry of davana essential oil (DEO), viz, volatile and nonvolatile constituents, phytomedicinal and pharmacological properties, which may help researchers achieve their future goals for approaching its industrial or commercial viability as a natural product ingredient.

Comparative Evaluation of the Essential Oil Content of Asteraceae Family Medicinal Plants

Background: The Asteraceae family comprises the largest flowering plant species, which have also been proven to have medicinal value for various illnesses due to the presence of numerous volatile and non-volatile constituents. Objective: The study aims to compare the volatile phytoconstiteunts presence in the essential oils of Asteraceae family plants including Roman Chamomile Oil (Chamaemelum nobile), German Chamomile Oil (Matricaria chamomilla), Davana Oil (Artemisia pallens), Wormwood Oil (Artemisia absinthium), Armoise Oil (Artemisia vulgaris), Tansy Oil (Tanacetum vulgare), Yarrow Oil (Achillea millefolium), Tarragon Oil (Artemisia dracunculus), Tagetes Oil (Tagetes erecta) and Immortelle Absolute Oil (Helichrysum italicum) as simultaneous estimation using the novel methods. Methods: Roman chamomile, German chamomile, davana, wormwood, armoire, tansy, yarrow, tarragon, tagetes, and immortelle absolute oils were extracted by steam distillation from their respective Asteraceae species and carried out the gas chromatography analysis. Results: The result was that GC-MS analysis of selected essential oils contains terpenes and terpenoids in major amounts. Among the detected volatile constituents in crucial oils Methyl Chavicol was found higher 75.63% in Tarragon Oil compared to other constituents followed Neryl acetate (60.25%) found in the immortelle absolute oil, Cis davanone (55.36%) was found in the davana oil, Ocimene (45.58%) in the tagetes oil, α-bisabololoxide B (45.26%) in the German chamomile oil, Beta thujone (50.65%) in the tansy oil, Alpha thujone (40.21%) in the wormwood oil and Camphor (38.65%) in the armoise oil. 1,8-Cineole, Alpha pinene, and Camphene were found in three oils (Wormwood oil, Armoise oil and Yarrow oil) among the selected oils. result: The results revealed the majority of terpenes and terpenoid-natured compounds. Methyl Chavicol (75.634%) was the highest content found in the tarragon oil when compared to the compounds found in the ten Asteraceae essential oils. The compounds such as Neryl acetate (60.251%) werefound in the immortelle absolute oil, Cis davanone (55.3640%) was found in the davana oil, Ocimene (45.5856%) in the tagetes oil, α-bisabololoxide B (45.2655%) in the German chamomile oil, Beta thujone (50.6520%) in the tansy oil, Alpha thujone (40.2150%) in the wormwood oil and Camphor (38.654%) in the armoise oil. 1,8-Cineole, Alpha pinene and Camphene were the compounds found in three of the ten Asteraceae essential oils Conclusion: Finally, we concluded that species from the same family (Asteraceae) were biologically synthesized with different volatile constituents. Hence, each essential oil has a unique biochemical fingerprint. These findings will help the food industry in relation to natural flavoring.

Thermo-Oxidative Decomposition of Lovage (Levisticum officinale) and Davana (Artemisia pallens) Essential Oils under Simulated Tobacco Heating Product Conditions

Summary The thermo-oxidative decomposition of lovage (Levisticum officinale) and davana (Artemisia pallens) essential oils has been studied by pyrolysis-gas chromatography/mass spectrometry in 9% oxygen and 91% nitrogen atmosphere at 300 °C to simulate low-temperature tobacco heating conditions. Both lovage and davana oils contain numerous chemical substances; the main components of both oils are various oxygen-containing compounds. Isobenzofuranones are the most important constituents of lovage oil, and their relative intensity changed significantly during oxidative pyrolysis. (Z)-ligustilide underwent two kinds of decomposition reactions: an aromatization reaction resulting in the formation of butylidenephthalide and the scission of the lactone ring with the elimination of carbon dioxide or carbon monoxide. Davanone is the main component of davana oil, which did not decompose considerably during low-temperature oxidative pyrolysis. However, the relative yield of the second most intensive component, bicyclogermacrene, reduced markedly due to bond rearrangement reactions. Davana ether underwent oxidation reactions leading to the formation of various furanic compounds. The changes in the composition of both essential oils could be interpreted in terms of bond splitting, intramolecular rearrangement mechanisms and oxidation reactions of several constituents during low-temperature oxidative pyrolysis. The applied thermo-oxidative method was found to be suitable to study the stability of the essential oils and monitor the decomposition products under simulated tobacco heating conditions. In spite of the complicated composition of the essential oils, no evidence for interaction between the oil components was found. [Beitr. Tabakforsch. Int. 29 (2020) 27–43]

Influence of floatation technique on seed and seedling characters in davana (Artemisia pallens)

Davana ( Artemisia pallens ) is an important high valued annual medicinal and aromatic herb of India belonging to the family Asteraceae. India has a monopoly in production and export trade of davana oil and India stands 3 rd in essential oil production in the world. This study was conducted at the Department of Seed Science and Technology, Tamil Nadu Agricultural University, Coimbatore to upgrade the seed quality of davana seeds. The seeds were subjected to the following seed quality assessment. The observation made on seed recovery (%), 1000 seed weight (mg), germination per cent, seedling length (cm), dry matter production and vigour index. The results revealed that davana seeds upgraded with petroleum ether was found to improve the seed quality parameters viz ., 1000 seed weight (120 mg), germination (71 %) and vigour index (170.0).

Intraspecific variation in essential oil composition of the medicinal plant Lippia integrifolia (Verbenaceae). Evidence for five chemotypes

The aerial parts of Lippia integrifolia (incayuyo) are widely used in northwestern and central Argentina for their medicinal and aromatic properties. The essential oil composition of thirty-one wild populations of L. integrifolia covering most of its natural range was analyzed by GC and GC–MS. A total of one hundred and fifty two terpenoids were identified in the essential oils. Sesquiterpenoids were the dominant components in all but one of the collections analyzed, the only exception being a sample collected in San Juan province where monoterpenoids amounted to 51%. Five clearly defined chemotypes were observed. One possessed an exquisite and delicate sweet aroma with trans-davanone as dominant component (usually above 80%). Another with an exotic floral odour was rich in oxygenated sesquiterpenoids based on the rare lippifoliane and africanane skeletons. The trans-davanone chemotype is the first report of an essential oil containing that sesquiterpene ketone as the main constituent. The absolute configuration of trans-davanone from L. integrifolia was established as 6S, 7S, 10S, the enantiomer of trans-davanone from ‘davana oil’ (Artemisia pallens). Wild plants belonging to trans-davanone and lippifolienone chemotypes were propagated and cultivated in the same parcel of land in Santa Maria, Catamarca. The essential oil compositions of the cultivated plants were essentially identical to the original plants in the wild, indicating that the essential oil composition is largely under genetic control. Specimens collected near the Bolivian border that initially were identified as L. boliviana Rusby yielded an essential oil practically identical to the trans-davanone chemotype of L. integrifolia supporting the recent view that L. integrifolia (Gris.) Hieron. and L. boliviana Rusby are synonymous.

Arthropod Deterrents from Artemisia Pallens (Davana Oil) Components

Davanone, a key sesquiterpene component of davana oil, has been synthesized in five convenient steps. Oxygenated sesquiterpenes have been linked to insect deterrent properties. Based on initial screening of davana oil, davanone and its hydroxy precursors have been generated and are being evaluated as arthropod deterrents against disease vectors.

Synthesis of cis- and trans-Davanoids: Artemone, Hydroxydavanone, Isodavanone, and Nordavanone

A concise and versatile synthesis of both <i>cis</i> and <i>trans</i> dia­stereomers of the natural products artemone, hydroxydavanone, isodavanone, and nordavanone has been accomplished. The preparation of <i>trans</i>-davanone is also described. Each synthesis is six to eight steps from geranyl acetate, with differentiation between <i>cis</i> and <i>trans</i> products occurring through a diastereoselective cyclization prior to derivatization. Many of these compounds are minor components of davana oil and have now been synthesized for the first time.

Seed developmental and maturation studies in davana (Artemisia pallens)

Davana (Artemisia pallens) ia an important high valued annual medicinal and aromatic herb of India belonging to the family Asteraceae. India has a monopoly in production and export trade of davana oil and India stands 3 rd in essential oil production in the world. This study was conducted at Department of seed science and technology, TamilNadu Agricultural University, Coimbatore to determine the seed developmental and maturation studies in davana. The bulk davana crop was raised in the field. Individual flower heads were tagged at the time of flower opening. The seeds were collected at 5 days intervals and subjected to the following seed quality assessment. The observation made on seed moisture content (%), 1000 seed weight (mg), germination %, seedling length (cm), dry matter production and vigour index. The results revealed that physiological maturity of davana seeds was attained on 35 th day after anthesis, where in germination percentage (86), seedling length (2.3), vigour Index (198) and dry matter production (1.23mg) were higher.

Stereospecific Total Synthesis of (+)-Davana Acid, (+)-Nordavanone and (+)-Davanone

A short, total synthesis of (+)-davana acid, (+)-nordavanone and (+)-davanone, which are principle components of davana oil, is described. The notable features are the use of the Evans syn aldol reaction and cyclic ether formation by an intramolecular S N 2 displacement reaction as key steps.

GC-MS-Analysis, Antimicrobial Activities and Olfactory Evaluation of Essential Davana (Artemisia pallens Wall. ex DC) Oil from India

An essential oil sample of davana (Artemisia pallens Wall. ex DC.) and a fraction thereof were investigated for their chemical composition using GC and GC-MS. cis-Davanone (45.8%), bicyclogermacrene (9.6%), linalool (2.5%), caryophyllene oxide (2.2%) and phytol (2.1%) were found to be the main constituents of the davana oil sample. The main constituents of the fraction were analyzed as cis-davanone (72.2%), davana ether 2° (5.2%) and ( Z)-ethyl cinnamate (5.2%). Antimicrobial activities of the essential oil, the fraction, some major and reference compounds were evaluated against seven strains of bacteria and one yeast using agar diffusion and agar dilution methods. The davana essential oil showed antimicrobial activities against Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella enterica subsp. enterica and the yeast Candida albicans; the davana fraction was effective against all the tested bacteria and yeast except Pseudomonas aeruginosa and Proteus vulgaris. The oil and the fraction were also olfactorially evaluated.

Isomeric Enhancement of Davanone from Natural Davana Oil Aided by Supercritical Carbon Dioxide

The chemical nature of davanone isolated from natural davana oil via packed column preparative supercritical fluid chromatography with a carbon dioxide-based mobile phase has been defined. Analyses used to characterize davanone included nuclear magnetic resonance spectroscopy, optical rotation, mass spectrometry, headspace solid-phase microextraction, enantiomeric purity via gas chromatography (GC), and GC-coupled olfactometry. For comparison, natural davana oil was subjected to the same types of measurements. The enriched davanone sample was nearly 100% optically pure. This indicates that fractionation of the davana oil with supercritical fluids at near room temperature had little effect on the optical integrity of the sample.

Influence of plant growth stage on the essential oil content and composition in Davana (Artemisia pallens wall.).

The influence of three plant growth stages (full emergence of flower heads, anthesis, and initiation of seed set) on the essential oil content and composition in Davana (Artemisia pallens Wall) was investigated over two successive seasons. The essential oil content was found to be higher at the full emergence of flower heads than at anthesis and initiation of seed set stages. The contents of davanone, the major constituent of davana oil, and linalool decreased while those of (Z)- and (E)-methyl cinnamate, (E)-ethyl cinnamate, bicyclogermacrene, davana ether, 2-hydroxyisodavanone, and farnesol increased from flower heads emergence stage to the initiation of seed set stage. These results support the general practice of harvesting the crop at full bloom stage. Five compounds, viz., (Z)- and (E)-methyl cinnamates, (Z)- and (E)-ethyl cinnamates, and geranyl acetate, were identified for the first time in davana oil.

Fragrant components of oil from Artemisia pallens

The volatile components of the essential oil of Artemisia pallens (davana oil) have been investigated. The oil contained more than 50 compounds, of which 34 are identified. Eight components are reported for the first time of which five are new. 11-Hydroxy-8-oxo-9,10-dehydro-10,11-dihydronerolidol was also isolated indicating a possible role for this compound in the biogenesis of furano-sesquiterpenes of davana oil. The structures are elucidated mainly by spectroscopic methods.

Sesquiterpene ketones related to davanone from Artemisia pallens

Extraction of the aerial parts of Artemisia pallens afforded several sesquiterpene ketones not previously reported from davana oil, including a new 3,4-epoxy derivative of isodavanone, as well as cirsimaritin.

Transformation of davanone : Reductive cleavage of tetrahydrofuran and thermal cyclization of 1:3-diene

Cis- β -davanone ( 1 ) the major but odourless component of davana oil (Artemisia pallens) has been converted into various derivatives to yield the compounds with delicate aroma. The LiAlH 4 reduction resulted into the unusual cleavage of the tetrahydrofuran ring and the major reduction product ( 2 ) after thermal dehydration afforded an unusual electrocyclically rearranged cyclobutene ( 7 ).

Dihydrofurano-terpenoids of davana oil

The essential oil of Artemisia pallens (Davana oil) yielded an unusual monoterpenoid [2-(3-methylbut-2-enyl)-3-methyl-2,5-dihydrofuran ( 4 )] and a novel norditerpenoid [2-(3-methylbut-2-enyl)-5-(5-cinnaamoloxy-2-oxo-1,5-dimethylhex-3-enyl)-3-methyl-2,5-dihydrofuran ( 7 )] formed by the possible condensation of the monoterpenoid ( 4 ) with methyl heptenone ( 3 ). This is the first report of dihydrofurans in the essential oil of A . pallens .

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The structure of davanone a new sesquiterpene from davana: (Artemisia pallens, Wall.)

AbstractStructure I, based on chemical and spectroscopic evidence, is proposed for a new sesquiterpenoid ketone, davanone, isolated from the essential oil of Artemisia pallens, Wall., known as davana oil.