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Three bianthraquinone derivatives from the mangrove endophytic fungus Alternaria sp. ZJ9-6B from the South China Sea.

Huang CH, Pan JH, Chen B, Yu M, Huang HB, Zhu X, Lu YJ, She ZG, Lin YC - Mar Drugs (2011)

Bottom Line: Their structures were elucidated by one- and two-dimensional NMR spectroscopy, MS data analysis and circular dichroism measurements.Compounds 1, 2 and 3 were first isolated alterporriols with a C-2-C-2' linkage.The crystallographic data of tetrahydroaltersolanol B (7) was reported for the first time.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China.

ABSTRACT
Three new bianthraquinone derivatives, alterporriol K (1), L (2) and M (3), along with six known compounds were obtained from extracts of the endophytic fungus Alternaria sp. ZJ9-6B, isolated from the mangrove Aegiceras corniculatum collected in the South China Sea. Their structures were elucidated by one- and two-dimensional NMR spectroscopy, MS data analysis and circular dichroism measurements. Compounds 1, 2 and 3 were first isolated alterporriols with a C-2-C-2' linkage. The crystallographic data of tetrahydroaltersolanol B (7) was reported for the first time. In the primary bioassays, alterporriol K and L exhibited moderate cytotoxic activity towards MDA-MB-435 and MCF-7 cells with IC₅₀ values ranging from 13.1 to 29.1 μM.

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Key HMBC, NOE and 1H-1H COSY correlations of 1–3.
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f3-marinedrugs-09-00832: Key HMBC, NOE and 1H-1H COSY correlations of 1–3.

Mentions: Compound 1 was isolated as a red amorphous powder. HR-EIMS at m/z = 586.1471 [M]+ indicated the molecular formula C32H26O11 (calcd. for C32H26O11, 586.1470). Compound 1 exhibited strong optical rotation (c = 1.0, MeOH) which indicated the possibility of an asymmetric centre and/or axial chirality (Figure 2). The IR spectrum (KBr) exhibited a weak shoulder at 1652 cm−1 and an intense band at 1638 cm−1 for carbonyl groups. The UV spectrum displayed bands at 224, 280 and 437 nm, suggesting a quinonoid chromophore. The 1H NMR spectrum (Table 1) showed a pair of chelated hydroxyl resonances (δH = 13.61 and 13.15 ppm), four aromatic protons (δH = 7.67, 7.55, 6.92 and 6.88 ppm), two methoxyl protons (δH = 3.68 and 3.66 ppm), two singlet methyls (δH = 2.18 and 1.07 ppm), two methylene protons (δH = 2.53 and 2.72 ppm, δH = 2.20 and 2.34 ppm), and oxygenated methine (δH = 3.51 ppm). The 13C NMR spectrum displayed four carbonyl signals (δC = 183.6, 187.8, 181.1 and 186.7 ppm), twenty signs of aromatic carbons, one quaternary carbon (δC = 69.0 ppm), one methine (δC = 70.1 ppm) and two methylenes (δC = 29.1 and 36.1 ppm). These data implied that compound 1 possessed a bianthranquinone scaffold, including an anthraquinone unit and a tetrahydroanthraquinone unit (Figure 1) [5,13]. The unsubstituted carbons for two aromatic rings of the anthraquinone unit were located at C-8′ (δC = 130.3 ppm; δH = 7.67 ppm, d, J = 0.8 Hz), C-5′ (δC = 110.5 ppm; δH = 7.55 ppm, d, J = 0.8 Hz) and C-3′ (δC = 103.8 ppm; δH = 6.921 ppm, s) by the HMBC correlations (Figure 3). In the tetrahydroanthraquinone unit, one aromatic proton at H-3 (δH = 6.88 ppm, s) and the protons in the alicyclic ring, including one oxygenated methine H-5 (δH = 3.51 ppm, ddd, J = 5.4, 5.5, 12.5 Hz) and two methylene protons H-6 (δH = 2.53 and 2.72 ppm) and H-7 (δH = 2.20 and 2.34 ppm) were observed.


Three bianthraquinone derivatives from the mangrove endophytic fungus Alternaria sp. ZJ9-6B from the South China Sea.

Huang CH, Pan JH, Chen B, Yu M, Huang HB, Zhu X, Lu YJ, She ZG, Lin YC - Mar Drugs (2011)

Key HMBC, NOE and 1H-1H COSY correlations of 1–3.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3111185&req=5

f3-marinedrugs-09-00832: Key HMBC, NOE and 1H-1H COSY correlations of 1–3.
Mentions: Compound 1 was isolated as a red amorphous powder. HR-EIMS at m/z = 586.1471 [M]+ indicated the molecular formula C32H26O11 (calcd. for C32H26O11, 586.1470). Compound 1 exhibited strong optical rotation (c = 1.0, MeOH) which indicated the possibility of an asymmetric centre and/or axial chirality (Figure 2). The IR spectrum (KBr) exhibited a weak shoulder at 1652 cm−1 and an intense band at 1638 cm−1 for carbonyl groups. The UV spectrum displayed bands at 224, 280 and 437 nm, suggesting a quinonoid chromophore. The 1H NMR spectrum (Table 1) showed a pair of chelated hydroxyl resonances (δH = 13.61 and 13.15 ppm), four aromatic protons (δH = 7.67, 7.55, 6.92 and 6.88 ppm), two methoxyl protons (δH = 3.68 and 3.66 ppm), two singlet methyls (δH = 2.18 and 1.07 ppm), two methylene protons (δH = 2.53 and 2.72 ppm, δH = 2.20 and 2.34 ppm), and oxygenated methine (δH = 3.51 ppm). The 13C NMR spectrum displayed four carbonyl signals (δC = 183.6, 187.8, 181.1 and 186.7 ppm), twenty signs of aromatic carbons, one quaternary carbon (δC = 69.0 ppm), one methine (δC = 70.1 ppm) and two methylenes (δC = 29.1 and 36.1 ppm). These data implied that compound 1 possessed a bianthranquinone scaffold, including an anthraquinone unit and a tetrahydroanthraquinone unit (Figure 1) [5,13]. The unsubstituted carbons for two aromatic rings of the anthraquinone unit were located at C-8′ (δC = 130.3 ppm; δH = 7.67 ppm, d, J = 0.8 Hz), C-5′ (δC = 110.5 ppm; δH = 7.55 ppm, d, J = 0.8 Hz) and C-3′ (δC = 103.8 ppm; δH = 6.921 ppm, s) by the HMBC correlations (Figure 3). In the tetrahydroanthraquinone unit, one aromatic proton at H-3 (δH = 6.88 ppm, s) and the protons in the alicyclic ring, including one oxygenated methine H-5 (δH = 3.51 ppm, ddd, J = 5.4, 5.5, 12.5 Hz) and two methylene protons H-6 (δH = 2.53 and 2.72 ppm) and H-7 (δH = 2.20 and 2.34 ppm) were observed.

Bottom Line: Their structures were elucidated by one- and two-dimensional NMR spectroscopy, MS data analysis and circular dichroism measurements.Compounds 1, 2 and 3 were first isolated alterporriols with a C-2-C-2' linkage.The crystallographic data of tetrahydroaltersolanol B (7) was reported for the first time.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China.

ABSTRACT
Three new bianthraquinone derivatives, alterporriol K (1), L (2) and M (3), along with six known compounds were obtained from extracts of the endophytic fungus Alternaria sp. ZJ9-6B, isolated from the mangrove Aegiceras corniculatum collected in the South China Sea. Their structures were elucidated by one- and two-dimensional NMR spectroscopy, MS data analysis and circular dichroism measurements. Compounds 1, 2 and 3 were first isolated alterporriols with a C-2-C-2' linkage. The crystallographic data of tetrahydroaltersolanol B (7) was reported for the first time. In the primary bioassays, alterporriol K and L exhibited moderate cytotoxic activity towards MDA-MB-435 and MCF-7 cells with IC₅₀ values ranging from 13.1 to 29.1 μM.

Show MeSH
Related in: MedlinePlus