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.


Major correlations in 2D NMR spectra of compound 1
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig1: Major correlations in 2D NMR spectra of compound 1

Mentions: Compound 1 had the molecular formula of C37H58O10, which was determined by its HR-EIMS at m/z 662.4414 [M]+. The IR spectrum showed absorption for hydroxyl group at 3425 cm−1. The 1H NMR spectrum (Table 1) showed characteristic cyclopropane methylene signals at δH 0.29 and 0.52 (each 1H, d, J = 3.8 Hz), a secondary methyl at δH 0.86 (d, J = 6.5 Hz), six tertiary methyls at δH 1.01 to 1.52 (each 3H, s), an acetyl group at δH 1.98, and an anomeric proton at δH 4.89 (d, J = 7.6 Hz). The 13C NMR and DEPT spectroscopic data (Table 2) of 1 displayed a characteristic cimigenol-type triterpenoid carbon resonances, corresponding to the methylene carbon of the cyclopropane ring at δC 31.2 (C-19), four oxymethine carbons at δC 89.0 (C-3), 80.6 (C-15), 72.2 (C-23), and 90.5 (C-24), and two oxygened quaternary carbons at δC 112.3 and 71.3. Apart from above data, a glycosidic moiety signals [δC 107.7 (d), 76.1 (d), 75.3 (d), 73.5 (d) and 63.5 (t)] were also obseverd in its 13C NMR spectrum. These data showed similarities as those of cimigenol-3-O-[2′-O-acetyl]-β-d-xylopyranoside [12]. However, a detailed comparison of their 1D NMR spectra revealed that they had different sugar unit. The upfield shift of H-2′ (δH 5.56 → δH 4.08) and the downfield shift of H-4′ (δH 4.30 → δH 5.44) in their 1H NMR spectra, along with the HMBC correlation (Fig. 1) of H-4′ (δH 5.44) with the carbonyl group of the acetoxyl group (δC 171.0) and of the anomeric proton with C-3, indicated that a 4′-O-acetyl-xylopyranosyl at C-3 in 1 replaced the 2′-O-acetyl-xylopyranosyl in cimigenol-3-O-[2′-O-acetyl]-β-d-xylopyranoside. The sugar unit of 1 was further confirmed by comparing its TLC and specific rotation with a standard after acid hydrolysis. Thus, the planar structure of 1 was determined.Table 1


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)

Major correlations in 2D NMR spectra of compound 1
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig1: Major correlations in 2D NMR spectra of compound 1
Mentions: Compound 1 had the molecular formula of C37H58O10, which was determined by its HR-EIMS at m/z 662.4414 [M]+. The IR spectrum showed absorption for hydroxyl group at 3425 cm−1. The 1H NMR spectrum (Table 1) showed characteristic cyclopropane methylene signals at δH 0.29 and 0.52 (each 1H, d, J = 3.8 Hz), a secondary methyl at δH 0.86 (d, J = 6.5 Hz), six tertiary methyls at δH 1.01 to 1.52 (each 3H, s), an acetyl group at δH 1.98, and an anomeric proton at δH 4.89 (d, J = 7.6 Hz). The 13C NMR and DEPT spectroscopic data (Table 2) of 1 displayed a characteristic cimigenol-type triterpenoid carbon resonances, corresponding to the methylene carbon of the cyclopropane ring at δC 31.2 (C-19), four oxymethine carbons at δC 89.0 (C-3), 80.6 (C-15), 72.2 (C-23), and 90.5 (C-24), and two oxygened quaternary carbons at δC 112.3 and 71.3. Apart from above data, a glycosidic moiety signals [δC 107.7 (d), 76.1 (d), 75.3 (d), 73.5 (d) and 63.5 (t)] were also obseverd in its 13C NMR spectrum. These data showed similarities as those of cimigenol-3-O-[2′-O-acetyl]-β-d-xylopyranoside [12]. However, a detailed comparison of their 1D NMR spectra revealed that they had different sugar unit. The upfield shift of H-2′ (δH 5.56 → δH 4.08) and the downfield shift of H-4′ (δH 4.30 → δH 5.44) in their 1H NMR spectra, along with the HMBC correlation (Fig. 1) of H-4′ (δH 5.44) with the carbonyl group of the acetoxyl group (δC 171.0) and of the anomeric proton with C-3, indicated that a 4′-O-acetyl-xylopyranosyl at C-3 in 1 replaced the 2′-O-acetyl-xylopyranosyl in cimigenol-3-O-[2′-O-acetyl]-β-d-xylopyranoside. The sugar unit of 1 was further confirmed by comparing its TLC and specific rotation with a standard after acid hydrolysis. Thus, the planar structure of 1 was determined.Table 1

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.