Further New Sesquiterpene Lactones from Artemisia herba-alba subsp. valentina

Sanz, Juan F.; Falcó, Enrique; Marco, J. Alberto

doi:10.1021/np50070a024

Cited by 27 publications

(8 citation statements)

References 8 publications

(9 reference statements)

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“…Its composition was dominated by the sesquiterpene davanone and monoterpenes p-cymene, 1,8-cineole, chrysanthenone, cis-chrysanthenyl acetate, c-terpinene, myrcene and camphor. In addition, an appreciable number of sesquiterpene lactones have been isolated in Spanish A. herba-alba (Gomis et al, 1979;Marco et al, 1989Marco et al, , 1992Marco, 1989;Sanz et al, 1990aSanz et al, , 1990b.…”

Section: Introductionmentioning

confidence: 99%

Composition and infraspecific variability of Artemisia herba-alba from southern Spain

Salido

Valenzuela

Altarejos

et al. 2004

Biochemical Systematics and Ecology

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The composition of the essential oils of 16 individual plants of Artemisia herba-alba Asso ssp. valentina (Lam.) Marcl. (at the full bloom stage) growing wild in four different locations from southern Spain were investigated by capillary GC and GC-MS in combination with retention indices. Among the 60 identified constituents (accounting for 80.6-95.0% of the oils), 33 have been reported for the first time in Spanish A. herba-alba oil and 17 of them have not been previously described in A. herba-alba oil. From the analysis of the oil samples, it could be deduced that a noticeable chemical polymorphism typified this taxon. Four groups of essential oils exhibited a single compound with percentages near 30% or higher: davanone, 1,8-cineole, chrysanthenone and cis-chrysanthenol. Two further oil types showed p-cymene and cis-chrysanthenyl acetate as major components in moderate amounts (ca. 20%). All of these types of essential oils have not been previously found in A. herba-alba from Spain and the appearance of such considerable amount of p-cymene is described here for the first time in A. herba-alba. #

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Section: Introductionmentioning

confidence: 99%

Composition and infraspecific variability of Artemisia herba-alba from southern Spain

Salido

Valenzuela

Altarejos

et al. 2004

Biochemical Systematics and Ecology

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“…In both the 1 H and 13 C NMR spectra, the distinct signals for an acetyl group (δ H 1.93, 3H, s; δ C 21.0 and 172.5), an α-substituted acrylic acid (δ H 5.66, 1H, s and 6.19, 1H, s; δ C 126.6, 143.5, and 170.0), a terminal double bond (δ H 4.63, 1H, s and 4.79, 1H, s; δ C 107.9 and 152.7), and two oxygenated carbons (δ H 5.39, td, J = 11.3 and 5.1 Hz; δ C 73.1, δ C 75.0) were observed. These 1D NMR data were similar to those of 5-hydroxycostic acid, differing only in the acetyl residue. HMBC correlations from H 3 -14 and H 2 -15 to C-5 and from H-8 to the acetyl carbonyl carbon revealed that the 2D structure of 12 is 8- O -acetyl-5-hydroxycostic acid.…”

Section: Resultsmentioning

confidence: 99%

Nitric Oxide Inhibitory Sesquiterpenoids and Its Dimers from Artemisia freyniana

Zhang

Ren

et al. 2018

J. Nat. Prod.

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Two new disesquiterpenoids (1 and 2) and 11 new (3-13) and 10 known (14-23) sesquiterpenoids were isolated from the whole plants of Artemisia freyniana. Their structures were elucidated by spectroscopic data analysis and comparison with published NMR data. The absolute configurations of the new isolates (1-13) were assigned based on single-crystal X-ray diffraction data and comparison of the experimental and calculated ECD data. The eremophilane derivatives 8 and 9 possess an unprecedented 2-isopropyl-3,7,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1 H-indene scaffold, and a putative biosynthetic pathway for these compounds is proposed. Compounds 4, 5, and 9 exhibited inhibitory effects against LPS-stimulated nitric oxide (NO) production in RAW 264.7 macrophage cells with IC values of 10.8, 12.6, and 11.7 μM, respectively.

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“…Nauplii were collected after incubation for 24 h, then kept under the same conditions for another 24 h. Samples (triplicates) were dissolved in DMSO (2 mg /400 μL), then diluted serially and the volume was adjusted to 5 mL with seawater. Nauplii (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were added to each set of vials containing the samples.…”

Section: Brine Shrimp Bioassaymentioning

confidence: 99%

“…The sesquiterpene lactones 2-5 were previously isolated from the same plant, while compound 6 from T. santolinoides is reported here for the first time. [20]. The configuration at H-4 and Me-9 was determined unambiguously as α (equatorial) by comparing the 13 C NMR chemical shift of C-13 with the literature [21].…”

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confidence: 99%

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Cytotoxic Sesquiterpene Lactones of Egyptian Tanacetum santolinoides

Youssef

Ramadan

Ibrahim

et al. 2007

Natural Product Communications

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The chloroform soluble fraction of the methanolic extract of the aerial parts of Tanacetum santolinoides afforded six sesquiterpene lactones. Tanacetolide A (1) was isolated for the first time from a natural source, in addition to five known sesquiterpene lactones. The structures were established on the basis of extensive studies of their 1D and 2D (1 H-1 H COSY, HMQC, HMBC, HOHAHA and NOESY) NMR spectra and FAB mass spectral determinations. The compounds showed good cytotoxic activity when tested using the brine shrimp bioassay.

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Further New Sesquiterpene Lactones from Artemisia herba-alba subsp. valentina

Cited by 27 publications

References 8 publications

Composition and infraspecific variability of Artemisia herba-alba from southern Spain

Composition and infraspecific variability of Artemisia herba-alba from southern Spain

Nitric Oxide Inhibitory Sesquiterpenoids and Its Dimers from Artemisia freyniana

Cytotoxic Sesquiterpene Lactones of Egyptian Tanacetum santolinoides

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