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Tumor Inhibitors. 126. New Cytotoxic Neolignans from Aniba Megaphylla

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Tumor Inhibitors. 126. New Cytotoxic Neolignans from Aniba Megaphylla 586 J. Org. Chem., Vol. 43, No. 4, 1978 Kupchan et al. New Cytotoxic Neolignans from Aniba megaphylla Mez.1*2 S. Morris IK~pchan,~Kenneth L. Stevens,*4Eric A. Rohlfing, Barry R. Sickles, Albert T. Sneden,* Richard W. Miller, and Robert F. Bryan* Department of Chemistry, Uniuersity of Virginia, Charlottesuille, Virginia 22901 Received June 30,1977 The isolation and elucidation of the structure and stereochemistry of megaphone (l),a new cytotoxic neolignan from Aniba rnegaphylla Mez., are reported. Chemical and spectral evidence supported structure 1 for megaphone, and a direct x-ray crystallographic analysis confirmed the structure and established the stereochemistry. Two addi- tional new cytotoxic neolignans, megaphone acetate (2) and megaphyllone acetate (3), were isolated and their struc- tures deduced in light of the structure of 1. The lack of activity of these neolignans as inhibitors of mitosis in sea ur- chin eggs is discussed in terms of structural features. An alcoholic extract of Aniba megaphylla Mez. (Laura- Chart I. Fractionation of the Cytotoxic Extract from ceae)5 was found to demonstrate inhibitory activity in vitro Aniba megaphylla Mez. against cells derived from human carcinoma of the naso- dried ground roots of A. meqaphylla (1 kg) pharynx (KB)? Systematic fractionation of the active ethanol I extract (Chart I) guided by KB activity led to the isolation of I hot 95% ethanol extraction three new cytotoxic neolignans, megaphone (l),megaphone acetate (2), and megaphyllone acetate (3). ethanolic extract A (81.3 4) partition between water and chloroform chl oroforrrI so 1 u bl e water soluble fraction C (50.5 g) fraction B (12.2 9) I We partition between H,OIMethanol (1:9) 1, P= '- 1 and Skellysolve B 3 2_. R= CGCk3 I Skellysolve B soluble Methanol soluble Chromatography of fraction H over silica gel gave a fraction fraction E (5.7 g) fraction D which crystallized from chloroform-ether to afford mega- I phone (1).On the basis of high-resolution mass spectrometry partition between HiO/Methanol (?:E) and carbon tetrachloride and confirmation by elemental analysis, megaphone was as- 1 signed the molecular formula C22H3006. The NMR spectrum I I carbon tetrac9lorlde Methanol soluble exhibited signals at 6 3.88 (6 H), 3.83 (3 H), and 3.46 (3 H), soluble fraction G fraction F representing three aromatic and one aliphatic methoxyl groups and suggesting that megaphone was either a lignan or partition between h2Gl Methanol (4 6) neolignan. The NMR spectrum also showed a singlet at 6 6.66 Aand chloroform (2 H) and a doublet at 6 4.64 (1 H) which, when considered with the hydroxyl stretching band at 3600 cm-l in the infrared Flethanol soluble chloroform soluble 'raction I +raction P (IR) spectrum, indicated a benzyl alcohol moiety with the Publication Date: February 1, 1978 | doi: 10.1021/jo00398a013 aromatic ring symmetrically substituted. In order to confirm (1H, br)] and a secondary methyl group [6 0.77 (3 H, d, J = this partial structure, megaphone was oxidized using Jones 7.1 Hz)]. In the NMR spectrum of 4, the doublet for the sec- Downloaded by UNIV OF BRISTOL on October 27, 2009 | http://pubs.acs.org reagent to give d.ione 4.,C22H2806. The two-proton singlet was ondary methyl group shifted to 6 1.18, indicating that it was in close proximity to the benzylic alcohol. Additionally, in the NMR spectrum of 4, the signal for the proton on the carbon Me@yype \ Mb a to the secondary methyl group appeared as a quartet at 6 4.04 (1 H, J = 7.5 Hz), indicating that this carbon was attached OMe to two quaternary carbons. The data thus accounted for all but one site of unsaturation, 4 suggesting that there was an additional ring which included shifted downfield in the NMR spectrum of 4, and, in the IR the a$-unsaturated ketone. The 13C NMR spectrum of spectrum, the hydroxyl band disappeared and a new carbonyl megaphone confirmed the presence of all the above moieties, band appeared at 1590 cm-l, thus confirming the presence and the presence of six quaternary carbons was indicated- of an aryl ketone. four in the aromatic moiety, one in the carbonyl group, and The IR spectrum of 1 showed the presence of an a,P-un- one in the cyclohexenone ring. Consequently, the cyclohexe- saturated carbonyl moiety (1670 cm-'), and the NMR spec- none ring must also contain one methylene carbon. In addi- trum exhibited a doublet at 6 7.00 (1 H, J = 10.5 Hz) and a tion, signals were observed for two carbons with general doublet of doublets centered at 6 6.02 (1 H, J = 10.5,2.2 Hz) structure A. One signal was ascribed to the benzylic carbon which could be assigned to the a and p protons, respectively, in a cis-a,P-unsaturated carbonyl system. Oxidation of 1 to afford 4 gave little change in either the IR or the NMR signals assigned to this moiety, indicating that the a,P-unsaturated carbonyl portion of the molecule was unaffected. Further inspection of the NMR spectrum of 1 revealed the presence of an allyl group [6 5.83 (1 H, m), 5.30 (1H, br), 5.19 A 0022-326317811943-0586$01.00/0 0 1978 American Chemical Society New Cytotoxic Neolignans 3.Org. Chern., VoE. 43, No. 4, 1978 587 Table I. Atomic Parameters for the Nonhydrogen Atomsa Atom x la vlb 2 IC B 7706 (8) 1283 (7) 5130 (8) 3.4 8802 (9) 819 (8) 4937 (8) 3.8 10168 (8) 1067 (7) 5887 (8) 3.5 10105 (9) 1798 (7) 6915 (8) 3.7 8684 (10) 2225 (7) 7130 (8) 3.9 7338 (9) 1993 (8) 6191 (8) 3.7 11672 (10) -229 (10) 4940 (10) 5.6 12248 (12) 2991 (9) 7447 (11) 6.6 7345 (11) 3269 (9) 8473 (9) 5.2 5897 (8) 1123 (7) 4084 (8) 3.4 5845 (8) 1956 (7) 2904 (8) 3.5 6608 (10) 1472 (9) 1828 (9) 4.4 4182 (10) 3272 (8) 1200 (9) 4.6 5298 (12) 4225 (9) 1576 (10) 6.0 5062 (17) 5225 (11) 1693 (13) 9.9 4154 (9) 2398 (7) 2366 (8) 3.8 3527 (10) 3028 (7) 3425 (8) 3.6 1879 (11) 3144 (9) 3297 (10) 5.7 867 (10) 2563 (10) 2373 (10) 5.4 1306 (9) 1797 (8) 1429 (9) 4.5 3025 (9) 1425 (7) 1830 (8) 3.8 -179 (14) 389 (9) 54 (12) 6.8 Figure 1. Stereoscopic view (ORTEP) of the molecular conforma- 11579 (6) 664 (6) 5804 (6) 5.0 tion. 11450 (7) 2060 (6) 7873 (6) 5.0 8770 (7) 2930 (6) 8184 (6) 4.8 5772 (6) 0000 (-)b 3566 (6) 4.2 and the other to the carbon in the cyclohexenone ring attached 4429 (7) 3475 (6) 4384 (5) 4.7 to the methoxyl group. 358 (7) 815 (6) 1359 (6) 5.3 Oxidized megaphone (4) showed a one-proton doublet of a Positional parameters for the hydrogen atoms (see supple- doublets at 6 2.90 (J -= 10.5, 12.5 Hz) which could be assigned mentary material) are given as fractions of the unit-cell edges to one of the methylene protons in the cyclohexenone ring. ( x104)with esd’s, in parentheses, on the same scale. Equivalent Irradiation of this signal partially collapsed the multiplet at anisotropic thermal parameters (see supplementary material) ar~ 6 4.30 (MeO-CH), and irradiation of the multiplet at 6 4.30 given in A2. * Held fixed to define the origin. partially collapsed thie doublet of doublets, thus confirming that the methylene group was in close proximity to the MeO-CH moiety. 85:lOO. The temperature dependence was shown by the ratio Hydrogenation of megaphone (1) in EtOH gave an oil which in pyridine-d5 at 46 and at 83 “C which was 100:95 and 100:54, analyzed for C22H3.40,: (by high-resolution mass spectrometry) respectively. and showed hydroxyl bands in the IR spectrum [3600 (s) and In both megaphone hemiketal (6) and tetrahydromega- 3425 cm-1 (br)] but no carbonyl group. Attempts to oxidize phone hemiketal(5), the methyl group occurs at high field in the product with Jones reagent were unsuccessful, suggesting the NMR spectrum, Le., 6 0.60 (J = 7.5 Hz) and 0.62 (J = 7.6 that the secondary alcohol was no longer present. Therefore, Hz), respectively, thus indicating a cis relationship to the ar- a hemiketal structure, 5, was proposed for the product of the Publication Date: February 1, 1978 | doi: 10.1021/jo00398a013 omatic system, as found in similar neolignans from other hydrogenation reaction. The NMR data were also consistent Aniba species such as porosin.7~~The coupling constant of the with such a structure. benzylic proton (6 5.25, J = 9.7 Hz) in 5 indicated a gauche Downloaded by UNIV OF BRISTOL on October 27, 2009 | http://pubs.acs.org arrangement to the adjacent proton. Examination of the double doublet at 6 2.90 (one proton of the ring methylene Me0,floM group) showed coupling constants of 12.7 and 10.5 Hz, one of which was the geminal coupling constant. The other, because MeO’ \ of its magnitude, must be the result of a 1,2-trans diaxial in- OM teraction; hence, the aliphatic methoxyl group was in an 5 equatorial position. From these data the structure of megaphone could be as- Careful reexamination of the NMR spectrum of megaphone signed as 1. To confirm this structure, and to establish the (1) revealed “spurious” signals, e.g., 6 0.60 (d, J = 7.5 Hz), 3.37 molecular conformation and absolute stereochemistry, a direct (s), and 6.48 (9).
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