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FULL PAPER Eight-Membered Cyclic 1,2,3-Trithiocane Derivatives From FULL PAPER Eight-Membered Cyclic 1,2,3-Trithiocane Derivatives from Perophora viridis, an Atlantic Tunicate Toma´sˇ Rˇ ezanka*[a] and Valery M. Dembitsky[b] Keywords: Natural products / Sulfur heterocycles / NMR spectroscopy / Mass spectrometry Two novel sulfur derivatives, one of which is a glycoside, troscopy and mass spectrometry. The compounds gave posit- containing substituted 1,2,3-trithiocane cycles were isolated ive results in the brine shrimp toxicity assay and the sea ur- from Perophora viridis which was collected off the Atlantic chin test. coast of North Carolina. They were characterized by spectro- ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, scopic methods, mainly 1H NMR, 13C NMR, IR and UV spec- 2002) Introduction contained sulfur (color reactions according to Kates[21]) were subjected to semipreparative RP-HPLC, leading to the Marine tunicates belonging to the class Ascidiacea have isolation of two major compounds. One compound was been the subject of extensive chemical and biological in- isolated as an opaque amorphous solid and showed signific- vestigations. Numerous indole alkaloids,[1,2] tyrosine deriv- ant UV absorbances at 258 nm (cisoid diene) and 205 nm atives,[3] guanines,[4] pyrazine alkaloids[5] and piperidine al- (α,β-unsaturated acid). In the IR spectrum, diagnostic Ϫ kaloids[6] have been isolated and identified from tunicates. peaks were observed for a hydroxyl group (3550 cm 1) and Ϫ With the continued chemical interest in these marine organ- an α,β-unsaturated acid (1705 cm 1). isms, an increasing number of non-nitrogen containing met- Compound 1 shows a molecular ion at m/z ϭ 360.0884, abolites have also been isolated, for example longithor- compatible with the formula C16H24O3S3. The presence of ols[7,8,9] and diterpenes.[10] Tunicates have also proved to be a 1,2,3-trithiocane ring in 1 was suggested by the observa- a rich source of a broad spectrum of sulfur-containing nat- tion of three sequential losses of 32S in the low resolution ϩ ϩ ϩ ural products with fascinating structures and different bio- mass spectrum, i.e. 360 [M ], 328 [M Ϫ S], 296 [M Ϫ [11,12] ϩ Ϫ 1 logical activities. The first compound in this series was S2] and 264 [M S3]. The H NMR spectroscopic data varacin,[13] and other such compounds include lissoclino- for 1 are compiled in Table 1. The 1H-1H connectivities of toxins[14,15] and trithianes.[16,17] compound 1, H-8Ј to H-7Ј and H-6Ј to the methyl on C-6Ј, were elucidated by DQF-COSY. The relative 5Ј,6Ј-trans and 6Ј,7Ј-trans configurations were deduced from the vicinal ϭ ϭ Results and Discussion coupling constants J5Ј,6Ј 10.2 Hz and J6Ј,7Ј 10.4 Hz (see Table 1). These relative stereochemistries, which were fur- ther confirmed by NOESY correlations of H-5Ј/H-2, H-9Ј/ In the course of our program devoted to the search for H-6Ј, H-9Ј/H-3 and H-7Ј/H-10Ј (see Figure 1), are compat- new compounds from marine animals,[18,19] we found that ible with the relative stereochemistry of compound 1. the extract from Perophora viridis collected near Cape Hat- The absolute configuration at C-7Ј in 1 was determined teras (NC, USA) exhibited considerable biological activity. to be R by the modified Mosher method.[22,23] The ∆δ ϭ Lyophilized animals were extracted with a CH Cl /MeOH 2 2 δ Ϫ δ values in the trithiocane of the MTPA ester of 1 mixture according to the procedure of Bligh and Dyer.[20] S R are shown in Figure 1. The positive ∆δ values for the hydro- The upper (water/methanol) phase was subjected to chro- gen atoms oriented on the right side of the MTPA plane matography on Sephadex LH-20, and two fractions that and the negative ∆δ values for those located on the left side of the MTPA plane in the 7-hydroxy-trithiocane derivative [a] Institute of Microbiology Ј Videnˇska´ 1083, Prague, 14220 Czech Republic point to the R-configuration at C-7 . Fax: (internat.) ϩ42-02/41062347 The 13C NMR spectrum shows a total of 16 carbon res- E-mail: [email protected] onances indicating 16 total carbons. By comparing the 13C [b] Department of Pharmaceutical Chemistry and Natural Products, School of Pharmacy, Hebrew University of Jerusalem NMR spectroscopic data, two terminal methylene units P. O. Box 12065, Jerusalem 91190, Israel were recognized in the 6-carbon side chain (C-1ЈЈ to C-6ЈЈ). 2400 WILEY-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002 1434Ϫ193X/02/0714Ϫ2400 $ 20.00ϩ.50/0 Eur. J. Org. Chem. 2002, 2400Ϫ2404 Eight-Membered Cyclic 1,2,3-Trithiocane Derivatives from an Atlantic Tunicate FULL PAPER Table 1. 1Hand13C NMR signals of compound 1 1H 13C 1 Ϫ 170.0 2 6.05 (d, J ϭ 15.5 Hz, 1 H) 120.1 3 7.04 (dd, J ϭ 15.5, 9.1 Hz, 1 H) 151.2 4ЈϪ 45.8 5Ј 2.48 (dd, J ϭ 10.2, 9.1 Hz, 1 H) 52.1 6Ј 1.71 (ddd, J ϭ 10.4, 10.2, 6.6 Hz, 1 H) 35.6 7Ј 3.44 (ddd, J ϭ 10.4, 10.4, 3.5 Hz, 1 H) 75.7 8Ј ax 2.70 (dd, J ϭ 13.5, 10.4, Hz, 1 H) 38.4 eq 2.79 (dd, J ϭ 13.5, 3.5 Hz, 1 H) 9Ј 1.08 (d, J ϭ 6.6 Hz, 1 H) 14.8 10Ј 1.84 (s, 3 H) 21.2 1ЈЈ 1.54 (m, 1 H), 1.37 (m, 1 H) 36.1 2ЈЈ 2.06 (m, 2 H) 30.4 3ЈЈ Ϫ 149.2 4ЈЈ 6.37 (dd, J ϭ 16.9, 10.8 Hz, 1 H) 138.5 5ЈЈ 5.07 (d, J ϭ 10.8 Hz, 1 H) 114.4 5.15 (d, J ϭ 16.9 Hz, 1 H) 6ЈЈ 4.88 (s, 1 H), 5.01 (s, 1 H) 109.7 One of these, δH/δC ϭ 5.07, 5.15/114.4 (C-5ЈЈ), displays clas- sical[24] cis and trans couplings of 10.8 and 16.9 Hz, respect- ively, to δH/δC ϭ 6.37/138.5 (C-4ЈЈ). Conversely, the other terminal methylene, δH/δC ϭ 4.88, 5.01/109.7 (C-6ЈЈ), does not display any splitting, and is thus connected to a qua- ternary carbon, C-3ЈЈ. Furthermore, HMBC correlations between H-6ЈЈ and C-4ЈЈ, and H-5ЈЈ and C-3ЈЈ, place these two ethylene units adjacent to each other. Also, position C- 2ЈЈ was determined to be adjacent to C-3ЈЈ from HMBC correlations between H-2ЈЈ and C-4ЈЈ, H-4ЈЈ and C-2ЈЈ, and H-6ЈЈ and C-2ЈЈ. Position C-1ЈЈ was then evident on the basis of the COSY correlations between H-1ЈЈ and H-2ЈЈ. The 1H NMR spectrum contains a series of coupled res- onances spanning the chemical shift region from δ ϭ 1.08 to 3.44 ppm. A DEPT spectrum confirmed that these pro- tons are associated with one methyl, one methylene and Figure 1. Structure of the new sulfur derivative 1 from Perophora three methine groups. DEPT, COSY and HMQC analysis viridis collected off the Atlantic coast of North Carolina; the 1 identified the partial structure (YCH2-HCX-HCR-HCR - HMBC correlations and ChemDraw 3D-MM2 models (with and 2 without of hydrogens) of compound 1 are included YCR -CH3), with Y probably being S, on the basis of the associated 13C NMR shifts (δ ϭ 38.4 and 45.8 ppm, re- spectively). The COSY data observed are as follows: H-7Ј/ 1 1 H2-8Ј, H-6Ј; H-6Ј/H-7Ј, H-5Ј; H-5Ј/H-6Ј, H-9Ј. The protons DQF-COSY and H- H decoupling experiments to be a de- of each methine (methylene) are not equivalent and show rivative of trithiocane. The relative 5Ј,6Ј-trans,6Ј,7Ј-trans a complicated coupling in the 1H NMR spectrum, which and 7Ј,8Ј-cis configurations were deduced from the vicinal indicates that this partial structure is integrated into an coupling constants of H-5ЈϪH-8Ј See Table 2 and Fig- eight-membered ring. ure 2). The (E)-3ЈЈЈЈ-thiomethylacrylate ester was assigned These correlations, and ChemDraw 3D modeling, led to using a combination of spectroscopic data. The IR band at the elucidation of the complete stereochemistry, including 1655 cmϪ1 and UV absorption at 257 nm are in a good the chirality, of compound 1, as illustrated in Figure 1. agreement with literature values.[25] The HMBC experiment Consequently, the structure of 1 was determined to be shows a correlation from the thiomethyl signal (H-4ЈЈЈЈ)at (2E,4ЈR,5ЈS,6ЈS,7ЈR)-3-{7Ј-hydroxy-4Ј,6Ј-dimethyl-4Ј-(3ЈЈ- δ ϭ 2.28 ppm to the olefinic carbon signal at δ ϭ 147.8 methylenepent-4ЈЈ-enyl)-[1Ј,2Ј,3Ј]-trithiocan-5Ј-yl}acrylic ppm (C-3ЈЈЈЈ), which was correlated to the H-3ЈЈЈЈ signal acid. at δ ϭ 7.24 ppm in the HSQC spectrum. Further HMBC Compound 2 shows a molecular ion (determined by correlations from the H-3ЈЈЈЈ proton signal to signals at δ ϭ HRFABMS) at m/z ϭ 708.2240, compatible with the for- 113.4 ppm (C-2ЈЈЈЈ) and δ ϭ 165.4 ppm (C-1ЈЈЈЈ) completed mula C30H48N2O9S4. In the same manner as described the assignment. The J2ЈЈЈЈ,3ЈЈЈЈ coupling constant of 14.5 Hz above, the planar constitution of 2 was determined by and the ROESY correlation from C-4ЈЈЈЈ to H-2ЈЈЈЈ defined Eur.
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