Santolinolide B [(2R,3S,4S)-4-hydroxy-2,5-dimethyl-3-vinyl-5-hexenoic acid lactone]. A new irregular monoterpene from Artemisia tridentata tridentata

Epstein, William W.; Gaudioso, Larry A.

doi:10.1021/jo01332a006

Cited by 27 publications

(6 citation statements)

References 4 publications

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“…Artemisia exhibits significant intraspecies variations in terpenes present in their essential oils [ 16 , 26 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 ]. For example, the variation in volatile components of these plants may occur during plant maturation at different altitudes.…”

Section: Resultsmentioning

confidence: 99%

Neutrophil Immunomodulatory Activity of Farnesene, a Component of Artemisia dracunculus Essential Oils

Schepetkin

Özek

et al. 2022

Pharmaceuticals

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Despite their reported therapeutic properties, not much is known about the immunomodulatory activity of essential oils present in Artemisia species. We isolated essential oils from the flowers and leaves of five Artemisia species: A. tridentata, A. ludoviciana, A. dracunculus, A. frigida, and A. cana. The chemical composition of the Artemisia essential oil samples had similarities and differences as compared to those previously reported in the literature. The main components of essential oils obtained from A. tridentata, A. ludoviciana, A. frigida, and A. cana were camphor (23.0–51.3%), 1,8-cineole (5.7–30.0%), camphene (1.6–7.7%), borneol (2.3–14.6%), artemisiole (1.2–7.5%), terpinen-4-ol (2.0–6.9%), α-pinene (0.8–3.9%), and santolinatriene (0.7–3.5%). Essential oils from A. dracunculus were enriched in methyl chavicol (38.8–42.9%), methyl eugenol (26.1–26.4%), terpinolene (5.5–8.8%), (E/Z)-β-ocimene (7.3–16.0%), β-phellandrene (1.3–2.2%), p-cymen-8-ol (0.9–2.3%), and xanthoxylin (1.2–2.2%). A comparison across species also demonstrated that some compounds were present in only one Artemisia species. Although Artemisia essential oils were weak activators of human neutrophils, they were relatively more potent in inhibiting subsequent neutrophil Ca2+ mobilization with N-formyl peptide receptor 1 (FPR1) agonist fMLF- and FPR2 agonist WKYMVM, with the most potent being essential oils from A. dracunculus. Further analysis of unique compounds found in A. dracunculus showed that farnesene, a compound with a similar hydrocarbon structure as lipoxin A4, inhibited Ca2+ influx induced in human neutrophils by fMLF (IC50 = 1.2 μM), WKYMVM (IC50 = 1.4 μM), or interleukin 8 (IC50 = 2.6 μM). Pretreatment with A. dracunculus essential oils and farnesene also inhibited human neutrophil chemotaxis induced by fMLF, suggesting these treatments down-regulated human neutrophil responses to inflammatory chemoattractants. Thus, our studies have identified farnesene as a potential anti-inflammatory modulator of human neutrophils.

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Section: Resultsmentioning

confidence: 99%

Neutrophil Immunomodulatory Activity of Farnesene, a Component of Artemisia dracunculus Essential Oils

Schepetkin

Özek

et al. 2022

Pharmaceuticals

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“…A chilar pool approach for the synthesis of santolinolides A (213, Scheme 42) and B (214) [117] was reported by Fernandes et al [116] The Johnson-Claisen rearrangement was used as a key step. The chiral diol 208 obtained from diethyl (R,R)-tartrate was transformed into allyl alcohol 209.…”

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 99%

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

2013

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The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration.

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“…10 Previous reports on the essential oils of A tridentata indicate the plant to be composed largely of camphor (20%-45%), camphene (3%-21%), 1,8-cineole (12%-30%), thujone (6%), and borneol (5%). [11][12][13][14][15][16] In addition, several irregular monoterpenoids have been isolated and characterized, [17][18][19][20][21] including artemiseole, lyratrol, lyratral, neolyratrol, rothrockene, trans-chrysanthemol, santolinolides A, B, and C, 1-(3-hydroxymethyl-2,2-dimethylcyclopropyl)-2-methyl-2-propen-1-one, and 1-(3-hydroxymethyl-2,2-dimethylcyclopropyl)-2-methyl-1-propanone. Sesquiterpene lactones are major components of the nonvolatile phytochemicals found in A tridentata.…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition and Terpenoid Enantiomeric Distribution of the Essential oil of Artemisia tridentata Subsp. tridentata From Southwestern Idaho

Swor

Satyal

Timsina³

et al. 2022

Natural Product Communications

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Big sagebrush ( Artemisia tridentata) is a common shrub growing in the cold intermountain regions of western North America. The plant is an important food source for herbivores and was used in Native American traditional medicine. In this work, the essential oils were obtained from 3 individuals of A tridentata subsp. tridentata growing in southwestern Idaho. The essential oils were analyzed by gas chromatographic methods including chiral gas chromatography. The major components in the essential oils were yomogi alcohol (5.8%-30.8%), santolina epoxide (1.7%-10.5%), camphor (5.2%-20.1%), and ( Z)-tagetone (0.9%-8.9%). ( + )-α-Pinene, ( + )-β-pinene, ( + )-verbenone, ( − )-( E)-β-caryophyllene, and ( − )-δ-cadinene were the only enantiomers observed for these compounds. Camphene and camphor, on the other hand, showed wide variability in enantiomeric distribution. The enantiomeric distributions in A tridentata subsp. tridentata differ widely compared to other Artemisia species. There are large variations in the chemical compositions in A tridentata, both between subspecies and within subspecies.

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Santolinolide B [(2R,3S,4S)-4-hydroxy-2,5-dimethyl-3-vinyl-5-hexenoic acid lactone]. A new irregular monoterpene from Artemisia tridentata tridentata

Cited by 27 publications

References 4 publications

Neutrophil Immunomodulatory Activity of Farnesene, a Component of Artemisia dracunculus Essential Oils

Neutrophil Immunomodulatory Activity of Farnesene, a Component of Artemisia dracunculus Essential Oils

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

Chemical Composition and Terpenoid Enantiomeric Distribution of the Essential oil of Artemisia tridentata Subsp. tridentata From Southwestern Idaho

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