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A Viscidane Diterpene and Polyacetylenes from Cultures of Hypsizygus marmoreus.

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

Bottom Line: Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5).Their structures were elucidated on the basis of extensive spectroscopic studies.Compound 1 is the first finding of viscidane diterpene in mushrooms.

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, 650204, China.

ABSTRACT

Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5). Their structures were elucidated on the basis of extensive spectroscopic studies. Compound 1 is the first finding of viscidane diterpene in mushrooms. Compounds 1, 3 and 5 were tested for cytotoxicity against human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7 and SW-480. None of the compounds showed cytotoxic activity (IC50 > 40 µM).

No MeSH data available.


Related in: MedlinePlus

Key ROESY correlations of 1
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Fig2: Key ROESY correlations of 1

Mentions: Compound 1, obtained as oil, had the molecular formula C20H32O5 based on the HRESIMS (pos.), showing a quasi-molecular ion peak at m/z 375.2147 (calcd for C20H32O5Na, 375.2147) with five degrees of unsaturation. In accordance with the molecular formula, 20 carbon resonances were resolved in the 13C NMR spectrum (Table 1), including a saturated ketone at δC 222.0 (s), a set of signals at δC 149.0 (s), 134.3 (s), 121.4 (d), 114.6 (t) assignable to a terminal double bond and a trisubstituted one, three oxygen-bearing carbons at δC 78.7 (d), 74.6 (s) and 70.2 (d), as well as three methyl signals at δC 27.2 (q), 26.4 (q) and 23.5 (q). The 1H NMR spectrum (Table 1), in combination with the HSQC spectrum, exhibited three vinyl signals at δH 5.35 (1H, br. s), 5.08 (1H, br. s) and 4.77 (1H, br. s), four oxygen-bearing protons at δH 4.01 (1H, br. dd, J = 8.7, 4.7 Hz), 3.83 (1H, dd, J = 11.4, 5.3 Hz), 3.71 (1H, dd, J = 11.4, 5.8 Hz) and 3.06 (1H, br. s), three spin-coupled protons at δH 3.05 (1H, dd, J = 8.8, 4.4 Hz), 2.53 (1H, dd, J = 19.4, 8.8 Hz) and 2.41 (1H, dd, J = 19.4, 4.4 Hz), and three tertiary methyls signals at δH 1.67 (3H, s), 1.24 (3H, s), and 1.22 (3H, s). According to the degrees of unsaturation, this molecule contained two rings. The above NMR character was very similar with that of a known compound viscida-3,11(18),14-triene [20]. Nevertheless there were obvious differences: the absence of a trisubstituted double bond signals, a doublet methyl signals and two high field methylene signals, instead a saturated carbonyl carbon signal and four oxygen-bearing carbon signals were observed. The carbonyl and hydroxymethyl were posited at C-8 and C-7 respectively, as established by the HMBC correlations (Table 1) of δH 3.83 (1H, dd, J = 11.4, 5.3 Hz, H-19a) and 3.71 (1H, dd, J = 11.4, 5.8 Hz, H-19b) with δC 45.1 (s, C-1), 58.7 (d, C-7) and 222.0 (s, C-8); of δH 2.45 (1H, dd, J = 5.8, 5.3 Hz, H-7), 2.53 (1H, dd, J = 19.4, 8.8 Hz, H-9a), 2.41 (1H, m, H-9b), 3.05 (1H, m, H-10), 3.83 (1H, dd, J = 11.4, 5.3 Hz, H-19a) and 3.71 (1H, dd, J = 11.4, 5.8 Hz, H-19b) with δC 222.0 (s, C-8). HMBC correlations also evidenced that C-13, C-14 and C-15 in 1 were hydroxylated. From ROESY experiment (Fig. 2), the significant correlations of H-10/H-19 and H-19/H-6 were observed, indicating α-orientation of these protons. In combination with the comparison of relevant NMR chemical shifts and 1H–1H coupling constants with those of analogues [21, 22], the configuration of 1 was established as shown in Fig. 1. Accordingly, the structure of 1 was determined and named as 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol.Table 1


A Viscidane Diterpene and Polyacetylenes from Cultures of Hypsizygus marmoreus.

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

Key ROESY correlations of 1
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4402581&req=5

Fig2: Key ROESY correlations of 1
Mentions: Compound 1, obtained as oil, had the molecular formula C20H32O5 based on the HRESIMS (pos.), showing a quasi-molecular ion peak at m/z 375.2147 (calcd for C20H32O5Na, 375.2147) with five degrees of unsaturation. In accordance with the molecular formula, 20 carbon resonances were resolved in the 13C NMR spectrum (Table 1), including a saturated ketone at δC 222.0 (s), a set of signals at δC 149.0 (s), 134.3 (s), 121.4 (d), 114.6 (t) assignable to a terminal double bond and a trisubstituted one, three oxygen-bearing carbons at δC 78.7 (d), 74.6 (s) and 70.2 (d), as well as three methyl signals at δC 27.2 (q), 26.4 (q) and 23.5 (q). The 1H NMR spectrum (Table 1), in combination with the HSQC spectrum, exhibited three vinyl signals at δH 5.35 (1H, br. s), 5.08 (1H, br. s) and 4.77 (1H, br. s), four oxygen-bearing protons at δH 4.01 (1H, br. dd, J = 8.7, 4.7 Hz), 3.83 (1H, dd, J = 11.4, 5.3 Hz), 3.71 (1H, dd, J = 11.4, 5.8 Hz) and 3.06 (1H, br. s), three spin-coupled protons at δH 3.05 (1H, dd, J = 8.8, 4.4 Hz), 2.53 (1H, dd, J = 19.4, 8.8 Hz) and 2.41 (1H, dd, J = 19.4, 4.4 Hz), and three tertiary methyls signals at δH 1.67 (3H, s), 1.24 (3H, s), and 1.22 (3H, s). According to the degrees of unsaturation, this molecule contained two rings. The above NMR character was very similar with that of a known compound viscida-3,11(18),14-triene [20]. Nevertheless there were obvious differences: the absence of a trisubstituted double bond signals, a doublet methyl signals and two high field methylene signals, instead a saturated carbonyl carbon signal and four oxygen-bearing carbon signals were observed. The carbonyl and hydroxymethyl were posited at C-8 and C-7 respectively, as established by the HMBC correlations (Table 1) of δH 3.83 (1H, dd, J = 11.4, 5.3 Hz, H-19a) and 3.71 (1H, dd, J = 11.4, 5.8 Hz, H-19b) with δC 45.1 (s, C-1), 58.7 (d, C-7) and 222.0 (s, C-8); of δH 2.45 (1H, dd, J = 5.8, 5.3 Hz, H-7), 2.53 (1H, dd, J = 19.4, 8.8 Hz, H-9a), 2.41 (1H, m, H-9b), 3.05 (1H, m, H-10), 3.83 (1H, dd, J = 11.4, 5.3 Hz, H-19a) and 3.71 (1H, dd, J = 11.4, 5.8 Hz, H-19b) with δC 222.0 (s, C-8). HMBC correlations also evidenced that C-13, C-14 and C-15 in 1 were hydroxylated. From ROESY experiment (Fig. 2), the significant correlations of H-10/H-19 and H-19/H-6 were observed, indicating α-orientation of these protons. In combination with the comparison of relevant NMR chemical shifts and 1H–1H coupling constants with those of analogues [21, 22], the configuration of 1 was established as shown in Fig. 1. Accordingly, the structure of 1 was determined and named as 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol.Table 1

Bottom Line: Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5).Their structures were elucidated on the basis of extensive spectroscopic studies.Compound 1 is the first finding of viscidane diterpene in mushrooms.

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, 650204, China.

ABSTRACT

Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5). Their structures were elucidated on the basis of extensive spectroscopic studies. Compound 1 is the first finding of viscidane diterpene in mushrooms. Compounds 1, 3 and 5 were tested for cytotoxicity against human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7 and SW-480. None of the compounds showed cytotoxic activity (IC50 > 40 µM).

No MeSH data available.


Related in: MedlinePlus