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Three Novel Cantharidin-Related Compounds from the Chinese Blister Beetle, Mylabris Phalerata PALL

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Three Novel Cantharidin-Related Compounds from the Chinese Blister Beetle, Mylabris Phalerata PALL July 2004 Chem. Pharm. Bull. 52(7) 807—809 (2004) 807 Three Novel Cantharidin-Related Compounds from the Chinese Blister Beetle, Mylabris phalerata PALL. Takafumi NAKATANI, Tomoyuki KONISHI, Kazumoto MIYAHARA, and Naoki NODA* Faculty of Pharmaceutical Sciences, Setsunan University; 45–1 Nagaotoge-cho, Hirakata, Osaka 573–0101, Japan. Received January 13, 2004; accepted April 5, 2004 Three novel cantharidin analogues were isolated from the Chinese blister beetle, Mylabris phalerata PALL. (Meloidae), which has been used in traditional Chinese medicine for the treatment of cancer. Their structures were determined on the basis of heteronuclear multiple-bond connectivity and nuclear Overhauser effect spec- troscopy experiments, and chemical data confirmed them to be so-called cantharimides, in which the anhydride oxygen atoms are replaced by the basic amino acid L-lysine, L-ornithine, and L-arginine moieties. Key words Chinese blister beetle; Mylabris phalerata; cantharimide; Meloidae; cantharidin Ј Ј Ј The dried body of the Chinese blister beetle is sold in 1.91), and between 9 -CH3 and H-4 (d 4.46) and Ha-5 (d China as Mylabris, a concoction has been used in traditional 1.91). These observations revealed that compound 1 consists Chinese medicine for the treatment of cancer.1—3) The of two parts, a cantharidin framework and an amino acid ly- species used in medicine are Mylabris phalerata PALL. and sine residue. Moreover, in its HMBC spectrum, H-2 of the M. cichorii LINN. (Meloidae). Among the chemical con- lysine moiety (d 4.42) showed diagnostically important cor- stituents in these species, cantharidin4,5) is a well-known ac- relations with C-1Ј (d 183.3) and C-3Ј (d 183.8) of the can- tive principle, but no other compounds have been isolated. In tharidin framework (Fig. 1). These findings indicate that 1 is our search for biologically active compounds from animal a so-called cantharimide, in which the anhydride oxygen crude drugs originating from invertebrates,6,7) we examined atom in cantharidin is replaced by the nitrogen atom of the the constituents of the Chinese blister beetle, Mylabris a-amino group in the lysine moiety. Confirmation of the ab- phalerata PALL., and isolated three compounds (1—3). Their solute configuration was achieved after the synthesis of com- chemical and spectral data revealed that they are so-called pound 1 as follows (Chart 1). cantharimides, in which the anhydride oxygen atoms are re- placed by the basic amino acid moieties. This paper deals with the isolation and structural elucidation of these com- pounds. Whole bodies of M. phalerata PALL. (3.4 kg) were ex- tracted with MeOH, and the methanolic extract was shaken with CHCl3–MeOH–H2O (1 : 1 : 1) to give an upper and a lower layer. The former was subjected to a combination of Sephadex LH-20, Diaion HP-20, and normal or reverse- phase column chromatography with various solvent systems to give compounds 1 (64.0 mg), 2 (9.1 mg), and 3 (57.2 mg). The high-resolution negative electrospray ionization (HR- ESI) MS of 1 exhibited a (MϪH)Ϫ ion peak at m/z 323.1607, 1 consistent with the molecular formula C16H24N2O5. The H- NMR spectrum of 1 showed six methylene ( 1.33, 1.63, d Fig. 1. NOE and HMBC Correlations of 1 1.64, 1.91, 2.15, 2.86) and three methine signals (d 4.42, 4.46, 4.46), together with two tertiary methyl signals (d 1.17, 1.21). The 13C-NMR spectrum exhibited 16 signals, includ- ing those of two quaternary (d 55.0, 55.3) and three carbonyl carbon signals (d 175.4, 183.3, 183.8). All proton and carbon signals were assigned on the basis of 2D-NMR spectra [1H–1H and 1H–13C shift correlation spectroscopy (COSY) and heteronuclear multiple-bond connectivity (HMBC)]. The COSY spectrum of 1 showed a series of correlation peaks from H-2 (d 4.42) to H-6 (d 2.86). In the HMBC spectrum, Ј the 8 -CH3 proton signal gave a long-range correlation with three carbon signals, C-1Ј (d 183.3), C-3Јa (d 55.0) and C-7Ј (d 85.4). Likewise, significant correlation peaks between the Ј Ј 9 -CH3 proton signal and three carbon signals, C-3 (d 183.8), C-7Јa (d 55.3), and C-4Ј (d 85.3) were observed. Nu- clear Overhauser effect spectroscopy (NOESY) gave NOE Ј Ј Ј correlations between 8 -CH3 and H-7 (d 4.46) and Ha-6 (d Chart 1 * To whom correspondence should be addressed. e-mail: [email protected] © 2004 Pharmaceutical Society of Japan 808 Vol. 52, No. 7 e Treatment of cantharidin with N -(tert-butoxycarbonyl)-L- structure depicted in Fig. 2. lysine in the presence of triethylamine in toluene at 200 °C Compound 3 showed a (MϪH)Ϫ ion peak at m/z 351.1666 for 48 h gave 1a. Deprotection of 1a with trifluoroacetic acid in its negative HR-ESI-MS, consistent with the molecular 1 13 13 gave 1b. The H- and C-NMR spectra of 1b were in good formula C16H24N4O5. This was confirmed by the C-NMR accord with those of 1, and its optical rotation showed the spectrum presenting signals for all 16 carbons of the molecu- same sign as that of 1. On the basis of all the above chemical lar formula including three carbonyl carbons (d 177.3, 186.3, and spectral data, the structure of 1 was determined to be 186.7), together with an additional nitrogen-substituted car- (2S)-6-amino-2-[(3aR*,4S*,7R*,7aS*)-3a,7a-dimethyl-1,3- bon (d 159.2). In the HMBC spectrum of 3, similar to those dioxo-4,7-epoxyoctahydroisoindol-2-yl]-hexanoic acid (Fig. of 1 and 2, significant correlations, including cross peaks be- 2). tween H-2 methine of the amino acid group and C-1Ј and C- Compound 2 provided a (MϪH)Ϫ ion peak at m/z 309.1450 3Ј of the cantharidin skeleton were observed. From these in the negative HR-ESI-MS, corresponding to the molecular findings, compound 3 is considered to be an analogue of 1 formula C15H22N2O5, which was one methylene group less and 2 differing only in the amino acid residue, that is, the ly- than that of 1. The 1H- and 13C-NMR spectra of compound 2 sine unit in 1 is replaced by the arginine moiety. were closely related to those of 1, except for the absence of To determine the absolute stereochemistry, we attempted the methylene proton (d 1.33) and the carbon (d 24.4) sig- to prepare compound 3 under the same conditions as de- nals observed in 1. These findings suggest that 2 is an ana- scribed for 1 and 2. However, no product could be obtained w logue of 1 in that the lysine moiety of 1 is replaced by the or- due to the poor solubility of N -(tert-butoxycarbonyl)-L-argi- nithine residue. This was confirmed by its HMBC and nine in toluene. The configuration at C-2 of the arginine moi- NOESY spectral data. ety remained unclear, but this is also considered to have an d Ϫ Condensation of cantharidin and N -(tert-butoxycar- L-form because it has optical rotation similar ([a]D 21.1°) Ϫ Ϫ bonyl)-L-ornithine, followed by deprotection in the same to those of 1 ([a]D 23.3°) and 2 ([a]D 26.9°). manner as described for 1, gave product 2b. The 1H- and 13C- Compounds 1—3 isolated in this study could be artifacts NMR spectra of 2b were almost identical to those of 2, and formed by condensation between cantharidin and the basic its optical rotation showed the same sign as that of 2. Ac- amino acids L-lysine, L-ornithine, and L-arginine. This possi- cordingly, the configuration at C-2 of the amino acid residue bility was excluded, however, since these compounds were was concluded to be an L-form, and thus compound 2 has the detected by TLC of the MeOH extract. Recently, many 8,9-dinorcantharidin analogues with vari- ous amino acid moieties, called norcantharimids, have been synthesized and tested for inhibitory activity against protein phosphatases 1 and 2A by McCluskey et al.8) They reported that these compounds with a basic amino acid D- or L-histi- dine residue are more potent inhibitors, whereas those with a neutral or an acidic amino acid residue have poor activity. This information leads us to expect that the three cantharim- ides obtained in this study have strong inhibitory activity against protein phosphatases 1 and 2A, because they consist of basic amino acid moieties. The biological activities of Fig. 2. Structures of 1, 2, and 3 these compounds will be examined in future investigations. Table. 1H- and 13C-NMR Spectral Data of 1—3 123(D2O) Position d C d H d C d H d C d H Cantharidin-1Ј 183.3 183.1 186.3 3Ј 183.8 183.7 186.7 4Ј 85.3 4.46 (dd, 5.4, 6.0) 85.5 4.47 (dd, 4.2, 4.2) 86.7 4.63 (dd, 6.0, 6.0) 5Ј 24.6 1.91 (m), 1.63 (m) 24.8 1.92 (m), 1.63 (m) 25.9 1.97 (m), 1.63 (m) 6Ј 24.8 1.91 (m), 1.63 (m) 25.1 1.92 (m), 1.63 (m) 26.2 1.97 (m), 1.63 (m) 7Ј 85.4 4.46 (dd, 5.4, 6.0) 85.6 4.47 (dd, 4.2, 4.2) 86.8 4.63 (dd, 6.0, 6.0) 3Јa 55.0 55.3 56.7 7Јa 55.3 55.6 56.9 8Ј 12.4 1.17 (s) 12.6 1.17 (s) 14.1 1.20 (s) 9Ј 12.6 1.21 (s) 12.9 1.21 (s) 14.3 1.24 (s) 1 175.4 174.9 177.3 2 56.5 4.42 (dd, 4.8, 10.8) 56.6 4.42 (dd, 7.8, 7.8) 57.8 4.50 (dd, 8.4, 8.4) 3 29.1 2.15 (2H, m) 27.3 2.16 (2H, m) 27.8 2.08 (2H, m) 4 24.4 1.33 (2H, m) 26.2 1.62 (2H, m) 28.4 1.48 (2H, m) 5 27.9 1.64 (2H, m) 40.4 2.90 (2H, m) 43.2 3.21 (m), 3.18 (m) 6 40.6 2.86 (2H, m) CϭNH 159.2 d (ppm) from TMS as an internal standard in CD3OD or D2O [coupling constants (Hz) in parentheses].
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