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New Diterpenes from Cultures of the Fungus Engleromyces goetzii and Their CETP Inhibitory Activity.

Wang Y, Zhang L, Wang F, Li ZH, Dong ZJ, Liu JK - Nat Prod Bioprospect (2015)

Bottom Line: One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms.The new compounds were elucidated based on their spectroscopic data.This paper reports the isolation, structural elucidation, and CETP inhibition activity of these compounds.

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

One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms. The new compounds were elucidated based on their spectroscopic data. In addition, compounds 1-6 were evaluated for their cholesterol ester transfer protein (CETP) inhibition activity. This paper reports the isolation, structural elucidation, and CETP inhibition activity of these compounds.

No MeSH data available.


Selected 2D NMR correlations of 2
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Fig3: Selected 2D NMR correlations of 2

Mentions: Compound 2 was isolated as white powder. The molecular formula C20H30O3 was determined by the HRESIMS analysis (m/z 341.2091 [M+Na]+), which indicated six degrees of unsaturation. The 1H NMR spectrum (Table 2) of 2 exhibited three olefinic protons at δH 5.87 (1H, dd, J = 17.5, 10.7 Hz), 4.97 (1H, dd, J = 17.5, 1.0 Hz) and 4.88 (1H, dd, J = 10.7, 1.0 Hz), one oxygen-bearing methine at δH 3.95 (1H, m) and three methyls at δH 0.98 (3H, s), 1.08 (3H, s) and 1.31 (3H, s). The 13C NMR spectrum showed 20 carbon resonances including one carbonyl, four olefinic carbons, one oxygen-bearing methine, three methyls, seven methylenes, one methine and three quaternary carbons. Comparison of NMR data of 2 with those of 7-deoxyrosenonolactone (6) [16], revealed the presence of the characteristic signals of a rosane-type diterpene. The resonances at δC 129.5 and 138.8 in the 13C NMR spectrum of 2 suggested there was an additional double bond in 2. The HMBC correlations from δH 2.42 and 1.86 to δC 129.5, δH 1.31 to δC 129.5; δH 2.22 and 1.97 to δC 138.8 as well as δH 0.98 to δC 138.8, indicated that the new double bond located between C-5 and C-10. Based on the analysis, the oxygen linkage between C-10 and C-18 in 6 was broken and formed a carboxyl at C-18 in 2, which was confirmed by the HMBC correlations from δH 2.21, 1.41 and 1.31 to δC 180.9. In addition, the resonance of δC 21.7 (t) in 6 is down shifted to δC 66.2 (d) in 2, indicated the methylene is oxidized by a hydroxyl. The HMBC correlations from δH 2.42, 2.21, 1.86 and 1.41 to carbon at δC 66.2, as well as the 1H–1H COSY correlations from δH 3.95 to δH 2.42, 2.21, 1.86 and 1.41, suggesting the hydroxyl was attached to C-2. The ROSEY spectrum showed cross peaks between CH3-20/H-2, H-1β/CH3-20, H-1α/H-8, H-8/H-6α, CH3-19/H-6α and CH3-17/H-8 suggested CH3-20, H-2, H-1β in the same side, and H-1α, H-8, H-6α, CH3-19 and CH3-17 in the opposite side (Fig. 3). The detailed analysis of chemical shift and coupling constant led to the determination that compound 2 was elucidated as engleromycenolic acid B.Table 2


New Diterpenes from Cultures of the Fungus Engleromyces goetzii and Their CETP Inhibitory Activity.

Wang Y, Zhang L, Wang F, Li ZH, Dong ZJ, Liu JK - Nat Prod Bioprospect (2015)

Selected 2D NMR correlations of 2
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4402584&req=5

Fig3: Selected 2D NMR correlations of 2
Mentions: Compound 2 was isolated as white powder. The molecular formula C20H30O3 was determined by the HRESIMS analysis (m/z 341.2091 [M+Na]+), which indicated six degrees of unsaturation. The 1H NMR spectrum (Table 2) of 2 exhibited three olefinic protons at δH 5.87 (1H, dd, J = 17.5, 10.7 Hz), 4.97 (1H, dd, J = 17.5, 1.0 Hz) and 4.88 (1H, dd, J = 10.7, 1.0 Hz), one oxygen-bearing methine at δH 3.95 (1H, m) and three methyls at δH 0.98 (3H, s), 1.08 (3H, s) and 1.31 (3H, s). The 13C NMR spectrum showed 20 carbon resonances including one carbonyl, four olefinic carbons, one oxygen-bearing methine, three methyls, seven methylenes, one methine and three quaternary carbons. Comparison of NMR data of 2 with those of 7-deoxyrosenonolactone (6) [16], revealed the presence of the characteristic signals of a rosane-type diterpene. The resonances at δC 129.5 and 138.8 in the 13C NMR spectrum of 2 suggested there was an additional double bond in 2. The HMBC correlations from δH 2.42 and 1.86 to δC 129.5, δH 1.31 to δC 129.5; δH 2.22 and 1.97 to δC 138.8 as well as δH 0.98 to δC 138.8, indicated that the new double bond located between C-5 and C-10. Based on the analysis, the oxygen linkage between C-10 and C-18 in 6 was broken and formed a carboxyl at C-18 in 2, which was confirmed by the HMBC correlations from δH 2.21, 1.41 and 1.31 to δC 180.9. In addition, the resonance of δC 21.7 (t) in 6 is down shifted to δC 66.2 (d) in 2, indicated the methylene is oxidized by a hydroxyl. The HMBC correlations from δH 2.42, 2.21, 1.86 and 1.41 to carbon at δC 66.2, as well as the 1H–1H COSY correlations from δH 3.95 to δH 2.42, 2.21, 1.86 and 1.41, suggesting the hydroxyl was attached to C-2. The ROSEY spectrum showed cross peaks between CH3-20/H-2, H-1β/CH3-20, H-1α/H-8, H-8/H-6α, CH3-19/H-6α and CH3-17/H-8 suggested CH3-20, H-2, H-1β in the same side, and H-1α, H-8, H-6α, CH3-19 and CH3-17 in the opposite side (Fig. 3). The detailed analysis of chemical shift and coupling constant led to the determination that compound 2 was elucidated as engleromycenolic acid B.Table 2

Bottom Line: One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms.The new compounds were elucidated based on their spectroscopic data.This paper reports the isolation, structural elucidation, and CETP inhibition activity of these compounds.

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

One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms. The new compounds were elucidated based on their spectroscopic data. In addition, compounds 1-6 were evaluated for their cholesterol ester transfer protein (CETP) inhibition activity. This paper reports the isolation, structural elucidation, and CETP inhibition activity of these compounds.

No MeSH data available.