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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 1
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Fig2: Selected 2D NMR correlations of 1

Mentions: Compound 1 was obtained as colorless oil, displayed an [M+Na]+ ion at m/z 341.2096 on the positive HRESIMS analysis, corresponding to the molecular formula C20H30O3 with six degrees of unsaturation. The 1H NMR spectrum of 1 (Table 1) exhibited two methyls at δH 1.28 (3H, s) and 0.80 (3H, s), five olefinic protons at δH 5.69 (1H, ddd, J = 17.1, 10.0, 10.0 Hz), 5.16 (1H, dd, J = 10.0, 2.2 Hz), 5.00 (1H, dd, J = 17.1, 2.2 Hz), 4.67 (1H, br.s) and 4.57 (1H, br.s). The 13C NMR spectrum showed 20 carbon resonances, including one carboxyl, four sp2 olefinic carbons, one oxygen-bearing methine, two tertiary methyls, six methylenes, four methines as well as two quaternary carbons. These data suggested compound 1 might be a tricyclic diterpene. The 1H and 13C NMR spectral data of 1 were similar to those of auricularic acid [15], which indicated that 1 was a cleistanthane-type diterpene. However, there are certain differences as follows: the resonance of C-2 at δC 19.5 in auricularic acid is down shifted to δC 65.3 in 1, suggesting that the methylene at C-2 was replaced by an oxygen-bearing methine. Furthermore, the HMBC correlations from δH 2.41, 2.13, 1.00, 0.93 to carbon at δC 65.3, and the 1H–1H COSY correlations from δH 4.14 to δH 2.41, 2.13, 1.00 and 0.93 in 1, indicating that the oxygen-bearing methane was placed at C-2. According to the molecular formula, we can conclude the oxygen-bearing methine at C-2 in 1 was substituted by a hydroxyl. In the ROSEY spectrum, the observed cross peaks of CH3-20/H-6β, H-2/CH3-20, CH3-20/H-8, H-8/H-15 and H-15/H-7β suggested that H-2, H-8, H-15 H-7β, H-6β and CH3-20 were in the same side, whereas the cross peaks of H-6α/CH3-19, H-9/H-14, H-7α/H-14 and H-7α/H-5 indicated that H-6α, CH3-19, H-9, H-14, H-7α, H-14 and H-5 lied on the opposite side (Fig. 2). Therefore, 1 was determined as engleromycenolic acid A.Table 1


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 1
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig2: Selected 2D NMR correlations of 1
Mentions: Compound 1 was obtained as colorless oil, displayed an [M+Na]+ ion at m/z 341.2096 on the positive HRESIMS analysis, corresponding to the molecular formula C20H30O3 with six degrees of unsaturation. The 1H NMR spectrum of 1 (Table 1) exhibited two methyls at δH 1.28 (3H, s) and 0.80 (3H, s), five olefinic protons at δH 5.69 (1H, ddd, J = 17.1, 10.0, 10.0 Hz), 5.16 (1H, dd, J = 10.0, 2.2 Hz), 5.00 (1H, dd, J = 17.1, 2.2 Hz), 4.67 (1H, br.s) and 4.57 (1H, br.s). The 13C NMR spectrum showed 20 carbon resonances, including one carboxyl, four sp2 olefinic carbons, one oxygen-bearing methine, two tertiary methyls, six methylenes, four methines as well as two quaternary carbons. These data suggested compound 1 might be a tricyclic diterpene. The 1H and 13C NMR spectral data of 1 were similar to those of auricularic acid [15], which indicated that 1 was a cleistanthane-type diterpene. However, there are certain differences as follows: the resonance of C-2 at δC 19.5 in auricularic acid is down shifted to δC 65.3 in 1, suggesting that the methylene at C-2 was replaced by an oxygen-bearing methine. Furthermore, the HMBC correlations from δH 2.41, 2.13, 1.00, 0.93 to carbon at δC 65.3, and the 1H–1H COSY correlations from δH 4.14 to δH 2.41, 2.13, 1.00 and 0.93 in 1, indicating that the oxygen-bearing methane was placed at C-2. According to the molecular formula, we can conclude the oxygen-bearing methine at C-2 in 1 was substituted by a hydroxyl. In the ROSEY spectrum, the observed cross peaks of CH3-20/H-6β, H-2/CH3-20, CH3-20/H-8, H-8/H-15 and H-15/H-7β suggested that H-2, H-8, H-15 H-7β, H-6β and CH3-20 were in the same side, whereas the cross peaks of H-6α/CH3-19, H-9/H-14, H-7α/H-14 and H-7α/H-5 indicated that H-6α, CH3-19, H-9, H-14, H-7α, H-14 and H-5 lied on the opposite side (Fig. 2). Therefore, 1 was determined as engleromycenolic acid A.Table 1

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.