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        毛韌革菌中的韌革菌素類似物(英文)

        2017-05-30 02:51:29周稚凡段媛昌李靖趙沛基
        廣西植物 2017年5期
        關(guān)鍵詞:化學(xué)成分

        周稚凡 段媛昌 李靖 趙沛基

        Abstract: In order to study the secondary metabolites of Stereum hirsutum FP91666, four vibralactone derivatives were isolated from YMG fermentation broth products of this strain —— one new vibralactone derivative, vibralactone R(1), together with three known vibralactones (2-4) —— by the methods of silica gel chromatography, gel chromatography, and semipreparative HPLC and so on. The new structure was elucidated by spectroscopic data including HRESIMS experiments, 1D and 2D NMR.

        Key words: phytochemistry, vibralactone, structure identification, chemical constituents, NMR

        CLC number: Q946

        Document code: A

        Article ID: 10003142(2017)05061704

        摘要: 從毛韌革菌(Stereum hirsutum FP91666)的YMG發(fā)酵液中分離得到1個新的韌革菌素類似物——韌革菌素R(1)以及3個已知的類似物——韌革菌素(2-4)。利用硅膠色譜、凝膠色譜等方法,結(jié)合半制備型HPLC對該菌次生代謝產(chǎn)物進(jìn)行研究得到這些化合物,并通過核磁共振(包括1DNMR、2DNMR)、高分辨質(zhì)譜實(shí)驗(HRESIMS)、紫外光譜等波譜學(xué)方法鑒定其結(jié)構(gòu)。

        關(guān)鍵詞: 植物化學(xué), 韌革菌素, 結(jié)構(gòu)鑒定, 化學(xué)成分, 核磁共振

        Stereum is basidiomycete fungus and belongs to Stereaceae family and can produce a variety of secondary metabolites (Nair et al, 1977; Dubin et al, 2000; Abraham 2001; Omolo et al, 2002). In the previous work (Duan et al, 2015), we used PDA medium to culture S. hirsutum FP91666 and obtained some compounds from the strain. On the basis of the genome data, S. hirsutum could yield further more secondary metabolites (Lackner et al, 2012). In process of studying the biosynthesis of vibralactone (Zhao et al, 2013), which generated from S. vibran and inhibited the pancreatic lipase with an IC50 value of 0.4 μg·mL1 (Liu et al, 2006), we had explored homologous genes of biosynthetic vibralactone, and learned that S. hirsutum can synthesize vibralactonetype compounds (Kim et al, 2009; Kim et al, 2010). In order to further explore its potential in production of new and active compounds, the OSMAC (one strain, many compounds) strategy was employed to mining the chemical diversity of this strain (Bode et al, 2002). And now one new vibralactone derivative, vibralactone R(1), together with three known vibralactones (2-4) were obtained from YMG fermentation broth products of S. hirsutum FP91666. The present work describes the isolation and structure of four vibralactones (Fig. 1).

        1Materials and Methods

        1.1 General

        UV spectra were measured using a Shimadzu UV2401 PC spectrophotometer (Shimadzu, Tokyo, Japan). NMR experiments were carried out on Bruker AM400 and Avance 600 NMR spectrometers with tetramethylsilane (TMS) as an internal standard. ESIMS and HRESIMS were recorded on a VG AutoSpec3000 mass spectrometer (VG, Manchester, England) and a Finnigan LCQAdvantage mass spectrometer (Thermo, San Jose, USA), respectively. Optical rotations were measured using a Jasco DIP370 digital polarimeter (JASCO, Tokyo, Japan). Column chromatography was carried out on silica gel (G, 200-300 mesh and GF254) (Qingdao Marine Chemical Factory, Qingdao, China) and Sephadex LH20 (Pharmacia). Precoated silica gel GF254 plates (Qingdao Marine Chemical Factory, Qingdao, China) were used for thin layer chromatography (TLC). Some fractions were purified by LC3000 Semipreparation Gradient HPLC (Beijing Chuangxintongheng Science & Technology Co., Ltd, Beijing, China).

        1.2 Fungal material

        S. hirsutum FP91666 was preserved in 20% glycerol at -80 ℃ in State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany. The strain was inoculated into 500 mL Erlenmeyer flasks, which contained 200 mL YMG broth (yeast extract 4.0 g·L1, malt extract 10.0 g·L1, glucose 4.0 g·L1, pH 7.3 before sterilization). After incubation at 26 ℃ for 7 d on a rotary shaker (180 r·min1), each primary culture was transferred into a 500 mL Erlenmeyer flask containing 250 mL the same broth and incubated at 26 ℃ for 21 d on a rotary shaker (180 r·min1).

        1.3 Extraction and isolation

        The extract of nButanol (10.51 g) of the culture broth (15 L) was separated on a column (silica gel G, 200-300 mesh, 150 g) and eluted with a petroleum ether (PE)EtOAc (10∶1 to 6∶4) and CHCl3MeOH (10∶1 to 0∶100) gradient solvent system to yield nine fractions (Fr. 1-Fr. 9). Fr. 2 (0.86 g) was subjected on a column (silica gel G, 200-300 mesh, 60 g) using a PEacetone (100∶4→0∶100) solvent system to produce six subfractions (Fr. 2.1-Fr. 2.6). Fr. 2.2 was subjected on Sephadex LH20 (MeOH) column and then purified by LC3000 Semipreparation Gradient HPLC (RPC18, 250 mm×10 mm, 5 μm, 210 nm, MeOHH2O from 50∶50 to 95∶5, a flow rate of 3.0 mL·min1) to yield 1 (5.6 mg) and 3 (4.2 mg). Fr. 2.3 was chromatographed on GF254 column using PEacetone (100∶4→0∶100) and then purified by Sephadex LH20 (MeOH) to produce 4 (2.1 mg). Fr. 3 (0.65 g) was subjected to a column (silica gel G, 200-300 mesh, 50 g) using a PEEtOAc (100∶4→0∶100) solvent system to produce seven subfractions (Fr. 3.1-Fr. 3.7). Fr. 3.1 was separated on a column (silica gel G, 200-300 mesh, 10 g) using CHCl3MeOH (100∶0→10∶1) and then purified by Sephadex LH20 (MeOH) column to yield 2 (5.2 mg).

        2Results

        2.1 Vibralactone R (1)

        Colorless oil; [α]= -6.8 (c = 1.3, MeOH); UV (MeOH) λmax (log ε): 202 (3.44); ESIMS: m/z 207 [M + Na]+; HRESIMS m/z: 207.099 4 [M + Na]+(calc. 207.099 7).

        Compound 1 was achieved as colorless oil. The HRESIMS data revealed a molecular formula of C10H16O3

        based on the [M + Na]+ ion signal at m/z 207.099 4 (calc. 207.099 7). The MS and NMR spectroscopic data of Compound 1 were substantially the same with those of vibralactone G (3) except that the chemical shifts of CH2-10 (δH 4.02, δC 68.3) and CH3-11 (δH 1.68, δC 13.9) were changed in Compound 1 (Wang et al, 2012). The 2DNMR data revealed that the H8 (δH 5.42) of methine correlated with the carbons at δC 68.3 (C10), 39.5 (C3), 28.4 (C7) and 13.9 (C11); H10 (δH 4.02) of methylene correlated with the carbons at δC 138.0 (C9), 120.9 (C8) and 13.9 (C11); H11 (δH 1.68) of methylene correlated with the carbons at δC 138.0 (C9), 120.9 (C8) 68.3 (C10) and 39.5 (C2). The NOESY experiment (Fig. 2) showed NOE correlations between H8 and H10; H5 and H4b; H4a and H3a, supporting the relative configurations. Based on the above data, Compound 1 was determinated to be as shown in Fig. 1, and named as vibralactone R.

        In addition, the three vibralactones D (2), G (3) and O (4) (Fig. 1) were identified by comparison of

        the MS and NMR data obtained with those reported in the literature (Wang et al, 2012; Chen et al, 2014).

        2.2 Vibralactone D (2)

        Colorless crystal; [α]= +17.4 (c = 0.8, MeOH); UV (MeOH) λmax (log ε): 202.5 (3.64); 1HNMR (CD3OD, 600 MHz) δ: 1.67 (1H, ddd, J1= 2.0, J2 = 5.2, J3 = 12.4 Hz, H2β), 1.80 (1H, dd, J1= 2.5, J2 = 12.4 Hz, H2α), 2.26 (1H, m, H3), 1.47 (1H, ddd, J1= 2.7, J2 = 4.6, J3 = 14.0 Hz, H4α), 2.40 (1H, m, H4β), 3.95 (1H, dd, J1= 4.6, J2 = 10.3 Hz, H5), 2.08 (1H, dd, J1= 8.2, J2 = 14.3 Hz, H8β), 2.60 (1H, dd, J1 = 6.7, J2 = 14.3 Hz, H8α), 5.06 (1H, m, H9), 1.56 (1H, s, H11), 1.61 (1H, s, H12), 4.08 (1H, brd, J = 9.1 Hz, H13a), 4.25 (1H, ddd, J1 = 1.0, J2 = 2.6, J3 = 10.2 Hz, H13b); 13CNMR (CD3OD, 150 MHz) δ: 58.3 (C1), 34.8 (C2), 34.3 (C3), 38.8 (C4), 79.3 (C5), 175.6 (C7), 31.9 (C8), 121.4 (C9), 135.5 (C10), 18.2 (C11), 26.3 (C12), 78.7 (C13); ESIMS: m/z 233 [M + Na]+; HRESIMS m/z: 233.1151 [M + Na]+(calc. 233.1154).

        2.3 Vibralactone G (3)

        Colorless oil;ESIME: m/z 207 [M + Na]+; 1HNMR and 13CNMR see Table 1.

        2.4 Vibralactone O (4)

        Colorless oil; ESIMS:m/z 213 [M+H]+; 1HNMR (CDCl3, 600 MHz) δ: 2.05 (1H, overlap, H2), 2.26 (1H, m, H3), 1.23 (1H, m, H4), 2.16 (1H, overlap, H4), 2.15 (1H, overlap, H5), 3.95(1H, m, H6), 3.56 (1H, m,H6), 3.80 (1H, m, H7), 3.45 (1H, m, H7), 2.04 (1H, overlap, H8), 2.40 (1H, m), 5.00 (1H, t, J = 6.5 Hz, H9), 1.57 (3H, s, H11), 1.63 (3H, s, H12); 13CNMR (CDCl3, 150 MHz) δ: 219.1 (s, C1), 57.8 (d, C2), 43.2 (d, C3), 30.1 (t, C4), 50.0 (d, C5), 62.5 (t, C6 ), 66.6 (t, C7 ), 28.5 (t, C8), 121.0 (d, C9), 134.4 (s, C10), 18.2 (q, C11), 26.0 (q, C12).

        References:

        ABRAHAM WR, 2001. Bioactive sesquiterpenes produced by fungi are they useful for humans as well [J]. Curr Med Chem, 8(6): 583-606.

        BODE HB, BETHE B, HOFS R, et al, 2002. Big effects from small changes: possible ways to explore natures chemical diversity [J]. Chem Biol Chem, 3(7): 619-627.

        CHEN HP, ZHAO ZZ, YIN RH, et al, 2014. Six new vibralactone derivatives from cultures of the fungus Boreostereum vibrans [J]. Nat Prod Bioprospect, 4(5): 271-276.

        DUAN YC, MENG XX, YANG YL, et al, 2015. Two new phenol derivatives from Stereum hirsutum FP91666 [J]. J Asian Nat Prod Res, 17: 324-328.

        DUBIN GM, FKYERAY A, TABACCHI R, 2000. Acetylenic aromatic compounds from Stereum hirsutum [J]. Phytochemistry, 53(5): 571-574.

        KIM GS, SUNG NS, PARK CB, et al, 2010. Repub. Korean Kongkae Taeho Kongbo [J]. Pat No KR, 20100614.

        KIM JP, KANG HS, PARK SH, 2009. Repub. Korean Kongkae Taeho Kongbo [P]. KR 2009089203 A 20090821.

        LACKNER G, MISIEK M, BRAESEL J, et al, 2012. Genome mining reveals the evolutionary origin and biosynthetic potential of basidiomycete polyketide synthases [J]. Fung Genet Biol, 49(12), 996-1003.

        LIU DZ, WANG F, LIAO TG, et al, 2006. Vibralactone: a lipase inhibitor with an unusual fused βlactone produced by cultures of the basidiomycete Boreostereum vibrans [J]. Org Lett, 8(25): 5749-5752.

        NAIR MSR, ANCHEL M, 1977. Frustulosinol, an antibiotic metabolite of Stereum frustulosum: Revised structure of frustulosin [J]. Phytochemistry, 16(3): 390-392.

        OMOLO JO, ANKE H, STERNER O, 2002. Hericenols AD and a chromanone from submerged cultures of a Stereum species [J]. Phytochemistry, 60(4): 431-435.

        WANG GQ, WEI K, FENG T, et al, 2012. Vibralactones GJ from cultures of the basidiomycete Boreostereum vibrans [J]. J. Asian Nat Prod Res, 14(2): 115-120.

        ZHAO PJ, YANG YL, DU L, et al, 2013. Elucidating the biosynthetic pathway for vibralactone: A pancreatic lipase inhibitor with a fused bicyclic βlactone [J]. Angew Chem Int Ed, 125(8): 2354-2358.

        rences in the ease of astringency removal by carbon dioxide gas and ethanol vapor treatments among oriental astringent persimmons of Japanese and Chinese origin [J]. Sci HortAmsterdam, 94:63-72.

        YIN XR, SHI YN, MIN T, et al, 2012. Expression of ethylene response genes during persimmon fruit astringency removal [J]. Planta, 235:895-906.

        YANG YX, WANG GY, PAN XC, 2009. China food composition: Book 1 [M]. Beijing: Peking University Medical Press, 2:71. [楊月欣,王光亞,潘興昌,2009. 中國食物成分表:第1冊 [M].北京:北京大學(xué)醫(yī)學(xué)出版社,2:71.]

        ZUO Y, FENG LX, JIA ZH, 2015. The direction of research and development of vitamins [J]. Cereals Oils, 28(9):1-5. [左玉,馮麗霞,賈澤慧,2015. 維生素類化合物的研究進(jìn)展 [J]. 糧食與油脂,28(9):1-5.]

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