The isolation and structure of tetraneurin-A, a new pseudoguaianolide from Parthenium alpinum var. tetraneuris (compositae)

Rüesch, H.; Mabry, Tom J.

doi:10.1016/0040-4020(69)85012-x

Cited by 26 publications

(13 citation statements)

References 10 publications

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“…Especially diagnostic were the 2,3 J C,H HMBC cross‐peaks of 10‐H with C‐1, C‐2, and C‐5, of Me‐15 with C‐1, the ketone C‐4, C‐5, and the oxymethine C‐6, and of 3‐H 2 with C‐4 and C‐5 for the carbon link, whereas the presence of an oxygen link was suggested by the molecular formula and the presence of two still‐unassigned oxygenated carbon atoms. The marked downfield shift of C‐1 ( δ C = 81.9 ppm in 6 , δ C = 86.2 ppm in 10 ) compared to data of dihydrocoronopilin ( 6 )17 further supported this assignment. The relative configuration at C‐5, C‐7, and C‐10 of 10 was assigned on the basis of the ROESY cross‐peaks of Me‐15 with both Me‐14 and 11‐H, whereas the α‐orientation of the oxygen bridge was suggested by the structural similarity of 10 with structurally related compounds 6 and 7 , where the 10‐hydroxy group is α‐oriented.…”

Section: Resultsmentioning

confidence: 57%

“…Along with several known compounds, eight new sesquiterpenoids were eventually isolated and characterized. The known compound obtained belonged to three major classes, namely, sesquiterpene lactones [isoalantolactone ( 1a ),11 dihydroisoalantolactone ( 1b ),12 peruvin ( 3 ),13 damsin ( 4a ),14 dihydrodamsin ( 5a ),15 acetoxydihydrodamsin ( 5b ),16 dihydrocoronopilin ( 6 ),17 and secoambrosanolide ( 11 )18], their acidic precursors [pre‐isoalantolactone ( 2 )19 and damsinic acid ( 8 )20], and daucane alcohols [lasidiol anisate 12 21,22]. Sesquiterpene lactones and acids are widespread in plants from the genus Ambrosia , but, with the exception of peruvin ( 3 ), none of these known compounds had been isolated from American populations of A. artemisiifolia , where the occurrence of sesquiterpene acids and daucanes is unreported.…”

Section: Resultsmentioning

confidence: 99%

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Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter

et al. 2012

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Allergy to common ragweed (Ambrosia artemisiifolia L.) is increasingly important from a clinical standpoint, but surprisingly, little is known on the secondary metabolites of this plant and their potential involvement in the severity of the allergic reactions induced by its pollen. Along with known compounds, eight novel sesquiterpenoids were isolated from the aerial parts of A. artemisiifolia, evidencing the presence of large amounts of electrophilic α,β‐unsaturated carbonyl derivatives. Because compounds of this type were also present in pollen, their reactivity with thiols was investigated and correlated to the activation of TRPA1, a polymodal sensor highly expressed in the aerial pathways and involved in airways sensory irritation, a common complication of allergy to Ambrosia.

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Section: Resultsmentioning

confidence: 57%

Section: Resultsmentioning

confidence: 99%

Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter

et al. 2012

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“…2, a). Although compound 3 has been prepared before as a semisynthetic derivative of tetraneurin A [18], our study represents the first report of its isolation from natural sources.…”

Section: Introductionmentioning

confidence: 97%

Pseudoguaianolides from the Flowers of Parthenium hysterophorus

Das

Mahender

Rao

et al. 2006

Helvetica Chimica Acta

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Two new pseudoguaianolide-type sesquiterpene lactones, named deacetyltetraneurin A (3) and hysterone E (4), were isolated from flowers of the plant Parthenium hysterophorus L., along with the seven known compounds parthenin (1), coronopilin, tetraneurin A, 8-b-hydroxycoronopilin, scopoletin, hysterone D, and conchasin A (2). The structures of all the compounds were deduced by means of elemental analysis and extensive spectroscopic (1D and 2D NMR) studies, and confirmed for 3 and 4 by X-ray crystallographic analysis. Results andDiscussion. -Extraction of the flowers of P. hysterophorus with CH 2 Cl 2 /MeOH 1 : 1 at room temperature yielded a mixture that was subjected to column chromatography (silica gel, hexane/AcOEt/acetone (gradient)). Thus the known compounds parthenin (1) [3], coronopilin [5], tetraneurin A [5], 8-b-hydroxycoronopilin [7], scopoletin [16], hysterone D [15], and conchasin A (2) [17], and the new compounds deacetyltetraneurin A (3) and hysterone E (4) were isolated (Fig. 1). 1 ) Part 56 in the series 'Studies on Phytochemicals', IICT Communication No. 051106.

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“…Parthenin (1) was also reacted with HCOONH 4 and Pd-C. Three products were obtained. Two of them are the natural pseudoguaianolides, dihydroisoparthenin (5) 10 and dihydrocoronopilin (6), 11,12 while the third product (7) is the known diastereoisomer of the latter (6). 12 The α-methylene-γ-butyrolactone moiety (ring C) of the parent compound, 1 was affected in all of these three products, 5-7.…”

Section: Resultsmentioning

confidence: 99%

“…Two of them are the natural pseudoguaianolides, dihydroisoparthenin (5) 10 and dihydrocoronopilin (6), 11,12 while the third product (7) is the known diastereoisomer of the latter (6). 12 The α-methylene-γ-butyrolactone moiety (ring C) of the parent compound, 1 was affected in all of these three products, 5-7. The retention of the ring C of 1 was also not observed when it was treated with NaBH 4 * Results were counted after 24 hours and inhibition zones were measured in millimiters.…”

Section: Resultsmentioning

confidence: 99%