Colladocin - a new triterpenoid coumarin from Colladonia triguetra

Sesquiterpene Phenylpropanoid and Sesquiterpene Chromone Derivatives from Ferula pallida

“…The HREIMS of 2 gave an intense parent ion peak, corresponding to a molecular formula of C 25 H 32 O 6 . Its 1 H and 13 C NMR data were also very similar to those of pallidones C-F. 1 Both the 1 H and 13 C NMR data of 2 indicated two double bonds. In the 1 H NMR spectrum of 2, 11′-CH 3 and 12′-CH 3 were singlets, indicating that C-10′ was a quaternary carbon.…”

“…Compound 1 was obtained as a colorless oil, and its HREIMS indicated a molecular formula of C 25 H 34 O 6 . 1 H and 13 C NMR data of 1 were very similar to those of pallidones C-F. 1 The double bond and the carbonyl group of the sesquiterpene unit were conjugated according to their NMR spectral data (δ H 6.07, br s, H-7′; δ C 201.5, C-8′; δ C 157.0, C-6′; δ C 124.2, C-7′). This was confirmed by the correlations of H-7′ with C-8′, C-9′, C-6′, and C-13′ and of H-9′ with C-8′, C-7′, C-11′, and C-12′ in the HMBC spectrum of 1.…”

“…In the HMBC spectrum of 3, the correlations of H-5 with C-4, C-7, and C-9; OMe with C-6, C-7, and C-8; H-15′ with C-1′, C-2′, and C-3; and H-1′ with C-4, C-2, C-14′, and C-3′ confirmed that C-1′ of the sesquiterpene unit was attached to C-3 of the chromone and that the methoxy group was attached to C-7. On the basis of the above analysis, and combined with the 13 C NMR spectral data (δ C-2′ 95.2, δ C-2 167.1, DEPT spectrum indicated both C-2′ and C-2 were quaternary carbons) and the molecular formula of 3, it was deduced that C-2 and C-2′ were linked by an oxygen atom.…”

“…The double bond at C-6′ has an E configuration based on the chemical shifts of C-5′ (δ C 41.3) and C-13′ (δ C 19.4). [2][3][4] The relative configuration was determined as 8S*, 1′R*, and 2′R* by comparison of the 13 C NMR data with those of pallidones C-F 1 and confirmed by the correlations of H-3′ with H-15′ and H-8 and of H-1′ with H-14′ in the NOESY spectrum. All of the 1 H and 13 C NMR assignments of 1 were made on the basis of 1 H-1 H COSY, HSQC, HMBC, and NOESY data.…”

“…The configuration of the double bond of the sesquiterpene unit was determined to be 5′E based on the 13 C NMR spectral data (δ C 16.6, C-13′). [2][3][4] In the NOESY spectrum of 3, the correlations of H-5′ with H-7′; H-13′ with H-4′; H-1′ with H-14′; and H-15′ with H-3′ suggested not only that the double bond was 5′E, but also that the relative stereochemistry of 3 was 1′R* and 2′R*.…”