Limits...
Six New 9,19-Cycloartane Triterpenoids from Cimicifuga foetida L.

Zhu GL, Zhu DF, Wan LS, Peng XR, Bao NM, Zhang ZR, Zhou L, Qiu MH - Nat Prod Bioprospect (2016)

Bottom Line: Six new 9,19-cycloartane triterpene derivatives, as well as 3 known analogues (7-9), were isolated from the roots of Cimicifuga foetida L.Their structures were established on the basis of extensive spectroscopic analyses (IR, UV, ORD, HRESIMS, 1D and 2D NMR).

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences (CAS), Kunming, 650201, People's Republic of China.

ABSTRACT
Six new 9,19-cycloartane triterpene derivatives, as well as 3 known analogues (7-9), were isolated from the roots of Cimicifuga foetida L. Their structures were established on the basis of extensive spectroscopic analyses (IR, UV, ORD, HRESIMS, 1D and 2D NMR).

No MeSH data available.


Key HMBC () and 1H-1H COSY () correlations of compounds 3, 4 and 6
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4940256&req=5

Fig2: Key HMBC () and 1H-1H COSY () correlations of compounds 3, 4 and 6

Mentions: Compound 3 was isolated as a white powder, showing [M + Na]+ ion at m/z 657.3602 in the HR-ESIMS consistent with the empirical molecular formula C35H54O10 (calcd 657.3615), requiring 9 sites of unsaturation. The IR and UV spectra exhibited absorption bands for hydroxyl group (3431 cm−1) and conjugated double bond (λmax 249 nm; 1631 cm−1), respectively. The 1H NMR spectrum exhibited a sec-methyl signal at δH 1.42 (3H, d, J = 6.4 Hz), six tert-methyls at δH 0.95–1.54 (each 3H, s), two olefinic methine signals at δH 5.92 (1H, br s) and 6.11 (1H, br s), and an anomeric methine signal at δH 4.85 (1H, d, J = 7.6 Hz). The 13C NMR showed 35 carbon resonances (Table 2), of which 30 were attributed to a triterpene skeleton and five to a pentose. A DEPT NMR experiment permitted differentiation of the 30 carbon signals into seven methyls, five methylenes, eleven methines (including five oxygenated and two olefinic signals), and seven quaternary carbons (including two oxygenated and two olefinic signals). The diagnostic signals of two oxygen-bearing methine carbons at δC 90.6 (C-24) and 70.4 (C-23), and a ketal carbon at δC at 112.7 suggested that 3 was a cimigenol-type triterpene compound. Further inspection of the 1D NMR and HSQC spectra of 3, the characteristic cyclopropane methylene resonances H2-19 and two quaternary carbons (C-9 and C-10) were not observed at the characteristic high magnetic field. Besides, comparison the NMR spectra of 3 with those of 12β-hydroxycimigenol-3-O-β-d-xylopyranoside [17], the signals due to C-9, C-10, C-11, and C-19 showed a downfield shift from δC 20.5, 26.1, 40.6, and 30.8 to 140.3, 138.7, 135.9, and 129.6, respectively, in 3. Such evidences indicated that 3 was a 9,10-seco-9,19-cyclolanostane glycoside with two double bonds. And the location of the double bonds (C10=C19 and C9=C11) could be further deduced. This was further supported by IR, UV and 2D NMR spectra (Fig. 2). Furthermore, the configurations of C-23 and C-24 were assigned as R and S, respectively, by the same way as 1. Ultimately, the structure of 3 was determined as 12β-hydroxy-10,19:9,11-didehydro-9,10-seco-cimigenol-3-O-β-d-xylopyranoside.Fig. 2


Six New 9,19-Cycloartane Triterpenoids from Cimicifuga foetida L.

Zhu GL, Zhu DF, Wan LS, Peng XR, Bao NM, Zhang ZR, Zhou L, Qiu MH - Nat Prod Bioprospect (2016)

Key HMBC () and 1H-1H COSY () correlations of compounds 3, 4 and 6
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4940256&req=5

Fig2: Key HMBC () and 1H-1H COSY () correlations of compounds 3, 4 and 6
Mentions: Compound 3 was isolated as a white powder, showing [M + Na]+ ion at m/z 657.3602 in the HR-ESIMS consistent with the empirical molecular formula C35H54O10 (calcd 657.3615), requiring 9 sites of unsaturation. The IR and UV spectra exhibited absorption bands for hydroxyl group (3431 cm−1) and conjugated double bond (λmax 249 nm; 1631 cm−1), respectively. The 1H NMR spectrum exhibited a sec-methyl signal at δH 1.42 (3H, d, J = 6.4 Hz), six tert-methyls at δH 0.95–1.54 (each 3H, s), two olefinic methine signals at δH 5.92 (1H, br s) and 6.11 (1H, br s), and an anomeric methine signal at δH 4.85 (1H, d, J = 7.6 Hz). The 13C NMR showed 35 carbon resonances (Table 2), of which 30 were attributed to a triterpene skeleton and five to a pentose. A DEPT NMR experiment permitted differentiation of the 30 carbon signals into seven methyls, five methylenes, eleven methines (including five oxygenated and two olefinic signals), and seven quaternary carbons (including two oxygenated and two olefinic signals). The diagnostic signals of two oxygen-bearing methine carbons at δC 90.6 (C-24) and 70.4 (C-23), and a ketal carbon at δC at 112.7 suggested that 3 was a cimigenol-type triterpene compound. Further inspection of the 1D NMR and HSQC spectra of 3, the characteristic cyclopropane methylene resonances H2-19 and two quaternary carbons (C-9 and C-10) were not observed at the characteristic high magnetic field. Besides, comparison the NMR spectra of 3 with those of 12β-hydroxycimigenol-3-O-β-d-xylopyranoside [17], the signals due to C-9, C-10, C-11, and C-19 showed a downfield shift from δC 20.5, 26.1, 40.6, and 30.8 to 140.3, 138.7, 135.9, and 129.6, respectively, in 3. Such evidences indicated that 3 was a 9,10-seco-9,19-cyclolanostane glycoside with two double bonds. And the location of the double bonds (C10=C19 and C9=C11) could be further deduced. This was further supported by IR, UV and 2D NMR spectra (Fig. 2). Furthermore, the configurations of C-23 and C-24 were assigned as R and S, respectively, by the same way as 1. Ultimately, the structure of 3 was determined as 12β-hydroxy-10,19:9,11-didehydro-9,10-seco-cimigenol-3-O-β-d-xylopyranoside.Fig. 2

Bottom Line: Six new 9,19-cycloartane triterpene derivatives, as well as 3 known analogues (7-9), were isolated from the roots of Cimicifuga foetida L.Their structures were established on the basis of extensive spectroscopic analyses (IR, UV, ORD, HRESIMS, 1D and 2D NMR).

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences (CAS), Kunming, 650201, People's Republic of China.

ABSTRACT
Six new 9,19-cycloartane triterpene derivatives, as well as 3 known analogues (7-9), were isolated from the roots of Cimicifuga foetida L. Their structures were established on the basis of extensive spectroscopic analyses (IR, UV, ORD, HRESIMS, 1D and 2D NMR).

No MeSH data available.