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Pure Appl. Chem., 2009, Vol. 81, No. 6, pp. 1019-1026

http://dx.doi.org/10.1351/PAC-CON-08-09-03

Published online 2009-04-24

Structure-activity relationships of antitubercular scalaranes: Heteronemin revisited

Sunan Jaisamut1, Suriyan Thengyai1, Supreeya Yuenyongsawad1, Chatchanok Karalai2, Anuchit Plubrukarn3,1* and Khanit Suwanborirux3

1 Marine Natural Products Research Unit, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
2 Department of Chemistry, Faculty of Science, Prince of Songkhla University, Hat-Yai, Songkhla 90112, Thailand
3 Center of Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Patumwan, Bangkok 10330, Thailand

References

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  • 10. The sponge was identified by Dr. Somchai Bussarawit of Phuket Marine Biology Center. The voucher specimen (PMBC 24608) is deposited at Phuket Marine Biology Center, Phuket, Thailand.
  • 11. The sponge was extracted in MeOH, and the crude MeOH-extract was partitioned to yield a hexane-extract, which was subjected to a series of chromatographic separation (SiO2, hexane:EtOAc:acetone 7:2:1; then SiO2, gradient hexane:EtOAc 7:3 1:1) to yield 6 (5 mg). 12epi-deacetyl-19α-acetoxy-20α-methoxyscalaran (6). White solid; [α]D +7.1 (c 0.21, CHCl3); UV (MeOH) λmax (log ε) 208 (4.47), 218 (4.45) nm; IR (neat) νmax 3444, 1734 cm1; 1H NMR (500 MHz, CDCl3) δ 6.45 (d, J = 3.0 Hz; H-19), 5.79 (dd, J = 6.5, 3.0 Hz; H-16), 5.09 (s; H-20), 3.38 (d, J = 12.0, 4.5 Hz; H-12), 3.32 (s, 3H; 20-OCH3), 2.81 (t, J = 3.0 Hz; H-18), 2.08 (m; H15a), 2.04 (s, 3H; 19-OCOCH3), 1.95 (m; H-15b), 1.64 (m; H-11a), 1.56 (m; H-1a), 1.51 (m; H-7a), 1.45 (m; H-2a), 1.40 (m; H-6a), 1.33 (m; H-11b), 1.29 (m,; H-2b), 1.26 (m; H-6b), 1.24 (m; H-3a), 1.15 (dd, J = 11.0, 5.5 Hz; H-14), 1.07 (td, J = 13.0, 3.5 Hz; H-3b), 0.86 (m; H9), 0.85 (m; H-7b), 0.83 (s, 3H; H-24), 0.81 (m; H-1b), 0.78 (s, 6H; H-21 & H-23), 0.74 (s, 3H; H22), 0.72 (dd, J = 14.0, 2.0 Hz; H-5), 0.69 (s, 3H; H-26); 13C NMR (125 MHz, CDCl3) δ 171.0 (19-OCOCH3), 135.8 (C-17), 121.8 (C-16), 104.6 (C-20), 99.6 (C-19), 80.5 (C-12), 58.6 (C-9), 56.8 (C-18), 56.4 (C-5), 54.6 (20-OCH3), 53.1 (C-14), 42.0 (C-7), 41.3 (C-3), 39.9 (C-1), 39.2 (C-13), 37.5 (C-10), 37.3 (C-8), 33.2 (C-21), 33.3 (C-4), 27.6 (C-11), 22.4 (C-15), 21.3 (C-22), 21.3 (19-OCOCH3), 18.5 (C-6), 18.0 (C-2), 17.3 (C-24), 16.5 (C-23), 8.8 (C-25); HR-ESIMS m/z [M+Na]+ 483.3071 (calcd for C28H44O5Na 483.3087).
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