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Chemical Constituents of the Japanese Liverwort Plagiochasma Pterospermum

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Chemical Constituents of the Japanese Liverwort Plagiochasma Pterospermum J. Hattori Bot. Lab. No. 85: 239- 244 (Nov. 1998) CHEMICAL CONSTITUENTS OF THE JAPANESE LIVERWORT PLAGIOCHASMA PTEROSPERMUM 1 1 TOSHIHIRO HASHIMOT0 , HIROSHI IRITA and y OSHINORI ASAKA w A 1 ABSTRACT. From the ether and ethyl acetate extracts of the Japanese liverwort, Plagiochasma pterospermum (Aytoniaceae), the sesquiterpene alcohol, ( + )-gymnomitr-8(12)-en-9a-ol, the triterpene alcohol, a-zeorin and two macrocyclic bis(bibenzyls), pakyonol and riccardin C have been isolated, together with p-hydroxybenzaldehyde and their structures elucidated. P. pterospermum is chemically very similar to P. appendiculata, and Reboulia hemisphaerica, belonging to the same family as that of the Plagiochasma. INTRODUCTION Liverworts are rich sources of terpenoids and phenolic compounds, several of which show interesting pharmacological activity (Asakawa, 1990). We are continuing to study the chemical constituents of liverworts from view point of biological activity of the isolated compounds and the chemosystematic study of bryophytes (Asakawa 1982, 1995). The Plagiochasma species belonging to the Aytoniaceae are rare thalloid liverworts and there are P. p.terospermum Mass. ( = P. intermedium Linden b. et Gott. var. nipponicum (Horik.) Inoue), P.japonicum (Steph.) Mass. in Japan, P. hodgsoniae Ham!. in New Zealand, P. rupestre in Europe and South America and P. algericum in Europe. We have reported the isolation and the structure elucidation of a new bis(bibenzyl), marchantin H (12) from P. pterospermum (Tori et al. 1988). Markham and Poter (l 978) reported the presence of three fl.avonoids, apigenin-7-0-glucuronide, kaemp­ ferol-3-0-rhamnosylglucoside and quercetin-3-0-rhamnosylglucoside from P. rupestre. Harrison et al. (1992) also found that P. rupestre contained two elemane- and one longipinane-type sesquiterpenoids, together with a-zeorin ( = hop-6a,22-diol) (11) and a flavone methyl ether. The Pakistani P. appendiculata elaborates three bis­ bibenzyls, marchantins A (15), B (16) and C (17), along with /3-caryophyllene (3) and {3-caryophyllene oxide (4). (Konoshima 1998). In order to study comparative biochemistry of the species belonging to the Aytoniaceae, we reinvestigated the chemical constituents of the Japanese P. pterospermum. Here we report the isolation and structures of the terpenoids and phenolic compounds from P. pterospermum. 1 Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. 240 J. Hattori Bot. Lab. No. 85 I 9 9 8 RESULTS AND DISCUSSION The air-dried P. pterospermum was ground and the powder was extracted with ether and then ethyl acetate. Two extracts were combined and a small amount of the viscous extract was analyzed by TLC and GC-MS. The presence of /3-elemene (1), <5-elemene (2), /3-caryophyllene (3), /3-barbatene (5), /3-bazzanene (6), gymnomitr- 8(12)-en-9a-ol (7), gymnomitr-8(12)-en-9{3-ol (8), gymnomitr-8(12)-en-9-one (9) and gymnomitran-9-one (10) of which compound 7 was the major component. The remaining extract was chromatographed on silica gel and Sephadex LH-20 to give ( + )-gymnomitr-8(12)-en-9cx-ol (7), cx-zeorin (11), pakyonol (13), riccardin C (14) and p-hydroxybenzaldehyde. Their structures were confirmed by the 1 H and 13C NMR spectra including two dimension techniques, high resolution mass spectrometry, IR and UV spectra. Their spectral data and physical constants were identical to those of authentic samples and to those of the references. The triterpene alcohol, cx-zeorin (11) has been isolated from two liverworts, Plagiochasma rupestre (Harrison et al. 1992) and Conocephalumn japonicum (Toyota & Asakawa 1993). The distribution of the triterpenoids is very rare in liverworts, however, they are widespread in mosses (Asakawa 1995). Riccardin C (12) is one of the popular cyclic bis(bibenzyls) in liverworts. It has been found in Reboulia hemisphaerica (Asakawa 1995; Asakawa & Matsuda 1982). Pakyonol (13) has been isolated from M annia fragrans belonging to the Aytoniaceae (Huneck et al. 1988). The sesquiterpene alcohol (7) has been isolated from European wild Reboulia hemisphaerica belonging to the Aytoniaceae and its in vitro cultured gametophyte (Morais et al. 1988). P. pterospermum is chemically similar to P. appendiculata since both species produces marchantin series (12 and 15-17). The elemane and longipinane type sesquiterpenoids found in P. rupestre (Harrison et al. 1992) were neither isolated from nor detected in P. pteroseprmum. In Table I, the chemical constituents of Plagiochasma, Mannia, Reboulia species which belongs to the Aytoniaceae have been shown. These three genera produce cyclic bis(bibenzyls) which have been isolated from the Marchantiaceae. Thus the Aytoniaceae are chemically related to the Marchantiaceae family. Among the Mannia, Plagiochasma and Reboulia, the Plagiochasma is chemically much more closer to the Reboulia because both genera produce the same triterpene alcohol (11), barbatane­ type sesquiterpenoids (7, 9, 10) and cyclic bis(bibenzyl) (14), although the distribu­ tion of the other sesquiterpenes are different from each other (Asakawa 1995). These chemical results are identical to morphological similarity of both genera. EXPERIMENT AL General 1H and 13C NMR spectra were recorded on a Varian Unity 600, a JEOL JNM GX-400 or a Varian Gemini 200 spectrometer. The solvent used for NMR spectra was CDC1 3 . Mass spectra were measured on a JEOL AX-500 spectrometer. The specific optical rotation was taken on a JASCO DIP-140 polarimeter in CHC1 3 solution. Silica gel (200-300 mesh) was used for column chromatography using n-hexane and ethyl T. HASHIMOTO et al. : Chemical constituents of Plagiochasrna pterosperrnurn 241 (1) (2) (3) (4) (9) (10) OH OMe OH OH OH HO HO OH R (15): R=H (12) (13) (14) (16): R=OH OH (1) ~-Elemene (10) Gymnomitran-9-one (2) S-Elemene (11) a-Zeorine (3) ~-Caryophyllene (12) Marchantin H (4) 13-Caryophyllene oxide (13) Pakyonol (5) ~-Barbatene (=Gymnomitrene) (14) Riccardin C (6) ~-Bazzanene (15) Marchantin A (7) (+)-Gymnomitr-8(12)-en-9a-ol (16) Marchantin B (8) Gymnomitr-8(12)-en-9~-ol (17) Marchantin C (9) Gymnomitr-8(12)-en-9-one (17) acetate gradient. CH2Cl 2 and MeOH (I: I) was used for Sephedex LH-20 column chromatography. Thin layer chromatography was carried out on precoated plates (Kiesel gel 60 F 254, 0.25 mm thick, Merk) using n-hexane-ethyl acetate (4: 1); spots were detected by illumination with UV lamp (254nm) or by spraying Godin reagent, follwed by heating at 120°C. GC-MS analysis of the ether and ethyl acetate extracts, each fraction of the combined extracts was carried out using Hewlett-Packard coupled 242 J. Hattori Bot. Lab. No. 85 I 9 9 8 Table I. Distribution of terpenoids and phenolic compounds in Plagiochasma, Mannia and Reboulia. Compounds P. pterospermum P. rupestre> P. appendiculatab> M . fragrans'> R. hemisphaericad > Sesquiterpenoids Barbatanes + + Bazzananes + + Cadinanes + Caryophyllanes + + Cuparanes + + Elemanes + Triterpenoids a-Zeorin + + + Bis(bibenzyls) Marchantin A + Marchantin B + Marchantin C + Marchantin H +<) Pakyonol + + Riccardin C + + a) Harrison et al. (1992); b) Konoshima (1998); c) Huneck et al. (1988); d) Morais et al. (1988); e) Tori et al. (1985). with a mass selective detector (MSD5971) at 70eV; the GC column was a fused silica column coated with DB-17 (30m x 0.25mm i.d., film thickness 0.25µm), and He gas used as carrier (I mljmin). The oven temp. was programmed from 80-250°C at 5°C/min; the injection temp was 250°C. Plant material Plagiochasma pterospermum was collected in Kyotani, Nishikuma, Monobe-gun, Koc hi Prefecture in August, 1997 by HI and TH and identified by Dr. M. Mizutani. Extraction and isolation P. pterospermum was dried for 10 days and ground mechanically. The powder (344 g) was extracted with diethyl ether for 4 days. Filtration and evaporation of the solvent gave the crude extract (2.61 g) . The residue was extracted with ethyl acetate for 26 days. The same treatment of the extract as mentioned above afforded the crude extract (520 mg). Both extracts were combined and a small amount of the crude extract was dissolved in ether and analyzed by TLC and GC-MS to detect /j-elemene (1) (8 .2%), b-elemene (2) (8.0%), /j-caryophyllene (3) (0.7%), /j-barbatene (5) (6.7 %), unidentified sesquiterpene hydrocarbon (1.2%) (119, [M] + 204), /j-bazzanene (6) (1.2%), gymnomitr-8(12)-en-9-one (9) (3 .2%), unidentified sesquiterpene alcohol (3 .0%) (m/z 137, [M] + 220), gymnomitr-8( l 2)-en-91X-ol (7), gymnomitran-9-one (10), gymnomitr-8(12)-en-9/j-ol (8). The remaining extract was chromatographed on silica T. HASHIMOTO et al. : Chemical constituents of Plagiochasma pterospermum 243 gel using n-hexane and ethyl acetate gradient to give 29 fractions. Frs. 1-5 were analyzed by GC-MS. Fr. 1 (4.7mg) contained three unidentified sesquiterpene hydrocarbons (m/z 41 base, [M] + 204; m/z 41, [M] + 204 and m/z 67, [M] + 204 ). Fr. 2 (2.0 mg) showed the presence of two unidentified sesquiterpene hydrocarbons' (m/z 41 base, [M] + 204; m/z 41 base, [Mr 204). Fr. 3 (2.0mg) contained /J-elemene (1), along with four unidentified sesquiterpene hydrocarbons (m/z 67 base, [M] + 204; m/z 89, [M] + 204, m/z 41 , [M] + 204, m/z 41 , [M] + 204). Fr. 4 (2.5 mg) contained' 7 unidentified sesquiterpene hydrocarbons (m/z 41 base, [M] + 204; m/z 67, [M] + 204, m/z 41, [M] + 204, m/z 41 , [M] + 204, m/z 179, [Mr 204 and m/z 189, [M] + 204). Fr. 5 (2.3mg) contained a sesquiterpene hydrocarbon (m/z 41 , [M] + 204). Fr. 6 (360. 7 mg) showed the presence of gymnomitr-8( 12)-en-9-one (9), gymnomitran-9-one (10), gymnomitr-8(12)-en-91lC-ol (7) , linoleic and linolenic acid methyl esters. From fractions 12 and 13 , the sesquiterpene alcohol, (-)-gymnomitr-8(12)-en-91lC-ol (7) (185mg) ([llC] 0 +25.3°; lit.
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