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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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CD Spectra of 2 and 3. Recorded in MeOH at amibient temperature.
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f4-marinedrugs-09-00832: CD Spectra of 2 and 3. Recorded in MeOH at amibient temperature.

Mentions: An interesting feature of the isolated bianthquinones is their optical activity. Ab initio calculations of CD spectra for several phenylanthraquinones with chiral axes have recently been reported [17,18]. Specific optical rotation of compounds 2 and 3 showed and −30, respectively. CD spectra of 2 and 3 recorded in methanol showed a near quasi-mirror image pattern (Figure 4). In the case of 2, the CD spectrum consists of a small positive band at 480 nm, followed by two moderate negative bands in the 300–400 nm regions, and a stronger negative band centered at 220 nm, then a stronger positive band at 264 nm. For 3, the sequence of bands is similar but their signs are inverted. The CD spectra of 2 and 3 reflect contributions from a chiral axis and three chiral centers. The chiral axis occurring within the chromophore is expected to dominate the observed CD spectrum [18,19] (Figure 4).The chiral center C-7 is expected to have a much smaller contribution to the observed CD spectrum. With these results, compounds 2 and 3 were deduced as two diastereomers and atropisomers [20].


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)

CD Spectra of 2 and 3. Recorded in MeOH at amibient temperature.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f4-marinedrugs-09-00832: CD Spectra of 2 and 3. Recorded in MeOH at amibient temperature.
Mentions: An interesting feature of the isolated bianthquinones is their optical activity. Ab initio calculations of CD spectra for several phenylanthraquinones with chiral axes have recently been reported [17,18]. Specific optical rotation of compounds 2 and 3 showed and −30, respectively. CD spectra of 2 and 3 recorded in methanol showed a near quasi-mirror image pattern (Figure 4). In the case of 2, the CD spectrum consists of a small positive band at 480 nm, followed by two moderate negative bands in the 300–400 nm regions, and a stronger negative band centered at 220 nm, then a stronger positive band at 264 nm. For 3, the sequence of bands is similar but their signs are inverted. The CD spectra of 2 and 3 reflect contributions from a chiral axis and three chiral centers. The chiral axis occurring within the chromophore is expected to dominate the observed CD spectrum [18,19] (Figure 4).The chiral center C-7 is expected to have a much smaller contribution to the observed CD spectrum. With these results, compounds 2 and 3 were deduced as two diastereomers and atropisomers [20].

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