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Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans.

Chu R, Wan LS, Peng XR, Yu MY, Zhang ZR, Zhou L, Li ZR, Qiu MH - Nat Prod Bioprospect (2016)

Bottom Line: Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee.Their chemical structures were elucidated by extensive spectroscopic analyses.Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

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, Kunming, 650201, China.

ABSTRACT
Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

No MeSH data available.


Related in: MedlinePlus

Key correlations in 2D NMR spectra of compound 5
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Fig4: Key correlations in 2D NMR spectra of compound 5

Mentions: 20-nor-cofaryloside II (5) possessed the molecular formula of C23H36O5, according to the HRESIMS analysis at m/z [M − H]− 391.2488 (calcd for 391.2490). Analyses of 5′s 1H and 13C NMR data indicated the existence of 23 carbon resonances, and C-21 (δC 104.2 s), C-22 (δC 26.9 q) and C-23 (δC 26.9 q) suggesting that the structure of compound 5 had the same ketal ring as compound 3 and this deduction was further supported by HMBC correlations from H2-17, H3-22 and H3-23 to C-21. The other 20 carbon signals showed that compound 5 was similar to 4 while the chemical shift of the oxygenated sp3 quaternary carbon C-10 (δC 77.1) of 5 was upfield shifted comparing to that of 4 (δC 90.6), and the molecular weight of 5 was 18 units more than that of 4 along with the degrees of unsaturation decrease by one. Therefore, the lactone linkage which assigned between COOH-19 and OH-10 was ring opened in 5. The relative configuration of 5 (Fig. 4) was same with 4. Thus, the structure was defined as 10α-hydroxy- 16α,17-[(1-methylethylidene)bis(oxy)]-9β-methyl-20-nor-ent-kauran-19-oic acid, and named 20-nor- cofaryloside II.Fig. 4


Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans.

Chu R, Wan LS, Peng XR, Yu MY, Zhang ZR, Zhou L, Li ZR, Qiu MH - Nat Prod Bioprospect (2016)

Key correlations in 2D NMR spectra of compound 5
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4940257&req=5

Fig4: Key correlations in 2D NMR spectra of compound 5
Mentions: 20-nor-cofaryloside II (5) possessed the molecular formula of C23H36O5, according to the HRESIMS analysis at m/z [M − H]− 391.2488 (calcd for 391.2490). Analyses of 5′s 1H and 13C NMR data indicated the existence of 23 carbon resonances, and C-21 (δC 104.2 s), C-22 (δC 26.9 q) and C-23 (δC 26.9 q) suggesting that the structure of compound 5 had the same ketal ring as compound 3 and this deduction was further supported by HMBC correlations from H2-17, H3-22 and H3-23 to C-21. The other 20 carbon signals showed that compound 5 was similar to 4 while the chemical shift of the oxygenated sp3 quaternary carbon C-10 (δC 77.1) of 5 was upfield shifted comparing to that of 4 (δC 90.6), and the molecular weight of 5 was 18 units more than that of 4 along with the degrees of unsaturation decrease by one. Therefore, the lactone linkage which assigned between COOH-19 and OH-10 was ring opened in 5. The relative configuration of 5 (Fig. 4) was same with 4. Thus, the structure was defined as 10α-hydroxy- 16α,17-[(1-methylethylidene)bis(oxy)]-9β-methyl-20-nor-ent-kauran-19-oic acid, and named 20-nor- cofaryloside II.Fig. 4

Bottom Line: Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee.Their chemical structures were elucidated by extensive spectroscopic analyses.Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

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, Kunming, 650201, China.

ABSTRACT
Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

No MeSH data available.


Related in: MedlinePlus