The root bark of Morus alba L. has been used as a blood pressure depressant in China and Japan from old times. The constituents of the root bark were well investigated by T. Nomura 1) and H. Hikino's 2) groups and many flavones and their derivatives were isolated as active principles. The leaves of this plant have also been used as a blood pressure depressant, but the constituents of the leaves have not yet been thoroughly investigated. We have investigated the pharmacological activities of the leaves of this plant and found that the butanol extracts of the leaves inhibit the increase of serum cholesterol and prevent atherosclerosis. 3a,b) In order to investigate the relationship of the constituents and the pharmacological activities of the leaves, we have studied the constituents of the butanol extracts of mulberry leaves. In this paper, we report the isolation and structural elucidation of two novel prenylflavanes (1, 2) and a glycoside (3) of 1 along with six known compounds, isoquercitrin (4), 4) astragalin (5), 5) scopolin (6), 6) skimmin (7), 7) roseoside II (8) 8) and benzyl D-glucopyranoside (9), 9) from the leaves of M. alba. The substitution pattern on the benzene rings was investigated by the analysis of heteronuclear multiple bond correlation spectroscopy (HMBC) spectrum of 1. As shown in (Fig. 2). The results of the NOE experiments and the spectral data mentioned above was satisfactorily explained by the structure (1) shown in Fig. 2. Results and DiscussionCompound 2 was obtained as an amorphous powder, [a] D Ϫ1.6°(cϭ1.0, MeOH). Its CI-MS spectrum showed the [MϩH] ϩ ion peak at m/z 341 corresponding to the molecular formula C 21 H 25 O 4 . Comparison of the 1 H-and 13 C-NMR spectra of 2 with those of 1 suggested that compound 2 is an isomer having the same framework as 1 and the structural difference should be the location of a methoxyl group. In the HMBC spectrum of 2, the methoxyl proton signal at d 3.74 showed a cross peak with the carbon signal at d 157.0 (C-7) which exhibited long range couplings with the proton signals at d 3.63-3.74 (H-1Љ) assignable to the methylene protons of a prenyl group. Furthermore, in the difference NOE experiments, irradiation of the methoxyl proton signal produced significant enhancement of the proton signal at d 6.57 due to February 2001 Chem. Pharm. Bull. 49(2) Two novel prenylflavanes (1, 2) and a glycoside (3) of 1 were isolated along with six known compounds, isoquercitrin (4), astragalin (5), scopolin (6), skimmin (7), roseoside II (8) and benzyl D-glucopyranoside (9), from the leaves of Morus alba. The inhibitory activities of compounds 1, 2 and 3 on the oxidation of human low density lipoprotein (LDL) were investigated.

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Glibenclamide, a sulfonylurea derivative (SU) antidiabetic agent was detected in a health food by three diŠerent methods: TLC, HPLC, and liquid chromatography-mass spectrometry (LC MS). For analysis of SU antidiabetics, the sample was extracted with acetone as a sample solution. TLC analysis of the sample solution showed a speciˆc spot that had the same characteristics as those of glibenclamide standard solution. HPLC analysis monitored using a photo-diode array detector showed that the sample solution had a peak with a unique UV spectrum, with coincided with that of standard glibenclamide. In sample solution, LC MS analysis in positive and negative modes indicated that the (M＋H) ＋ and (M-H) -ions occurred at m/z 494 and m/z 492, respectively. These results indicate that the monoisotopic mass is 493, coincident with that of glibenclamide. Quantitative HPLC analysis showed that the glibenclamide content in the health food was 0.78 mg/capsule (1.55 mg/g of sample contents). Because the initial dosage of glibenclamide for diabetics is 1.25-2.5 mg per day, this health food has su‹cient medicinal eŠect and also has the potential to cause adverse eŠects.

Drugs that have a pharmacological eŠect similar to legal drugs such as narcotics and stimulants are available in the market and widely used. 5-methoxy-N,N-di-iso-propyl-tryptamine (5MeO-DIPT) and a-methyl-tryptamine (AMT) were categorized as narcotics and were speciˆed as legal drugs in April 2005, and also 2,5-dimethoxy-4-n-propylthiophenethylamine (4C-T-7) and N-methyl-a-ethy-3,4-methylenedioxy-phenethylamine (MBDB) were categorized as narcotics and were speciˆed as legal drugs in April 2006, in Japan. We are analyzing these chemical drugs by investigating the market research. It is recognized that during the analysis of chemical drugs, drugs that resemble a structural isomer of a target substance, such as 5MeO-DIPT and 5-methoxy-N,N-di-n-propyl-tryptamine (5MeO-DPT) or 4C-T-7 and 2,5-dimethoxy-4-iso-propylthiophenethylamine (4C-T-4), should be distinguished. The results of TLC, IR, GC-MS and HPLC analyses were compared. 5MeO-DIPT and 5MeO-DPT could be distinguished by TLC and HPLC analyses, but not by IR and GC-MS analysis. The drugs 4-hydroxy-N-methyl-N-iso-propyl-tryptamine (4HO-MIPT) and 4-hydroxy-N,N-di-ethyl-tryptamine (4HO-DET) or could not be distinguished. Moreover, the isomers of 4-hydroxy-N-methyl-Nn-propyl-tryptamine (4HO-MPT) was not found to be present. Thus, we have demonstrated that the chemical drug could be distinguished from each other, and we have also shown that NMR data is essential for the analysis.Key words-abuse drug; structural isomerism; 5-methoxy-N,N-di-iso-propyl-tryptamine; 5-methoxy-N,N-di-npropyl-tryptamine; chemical drug