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        瓦山錐化學(xué)成分研究(1)

        2020-07-04 02:33:42李思雯王亞鳳何瑞杰戴天歌李典鵬黃永林
        廣西植物 2020年5期
        關(guān)鍵詞:化學(xué)成分

        李思雯 王亞鳳 何瑞杰 戴天歌 李典鵬 黃永林

        摘 要:? 瓦山錐植物富含植物多酚類成分且資源豐富,目前尚無(wú)該植物化學(xué)成分及生物活性方面的報(bào)道。為了明確瓦山錐的物質(zhì)基礎(chǔ),為該植物資源的合理開發(fā)與可持續(xù)利用提供科學(xué)依據(jù),該研究采用Sephadex LH-20、Diaion HP20SS、Toyopearl HW-40F等多種柱層析方法對(duì)瓦山錐樹葉乙醇提取物進(jìn)行分離純化,從中得到11個(gè)單體化合物,它們的結(jié)構(gòu)經(jīng)波譜數(shù)據(jù)分析及文獻(xiàn)對(duì)照鑒定為沒食子酸(1)、咖啡酸(2)、1-(3′, 4′-二羥基肉桂酰)-環(huán)戊-2,3-二酚(3)、綠原酸(4)、綠原酸甲酯(5)、kaempferol 3-O-β-D-glucuronopyranoside(6)、kaempferol 3-O-{β-D-xylopyranosyl-(1→2)- [α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside}(7)、quercetin 3-O-β-D-glucuronopyranoside(8)、quercetin 3-O-β-glucuronide-6″-methyl ester(9)、蘆?。?0)、quercetin 5-O- [α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside(11)。所有化合物均為首次從瓦山錐中分離得到,其中化合物3,7-11為首次從錐屬植物中分離得到。

        關(guān)鍵詞: 瓦山錐, 化學(xué)成分, 結(jié)構(gòu)鑒定, 植物多酚

        中圖分類號(hào):? Q946

        文獻(xiàn)標(biāo)識(shí)碼:? A

        文章編號(hào):? 1000-3142(2020)05-0648-06

        Chemical constituents from Castanopsis ceratacantha (Ⅰ)

        LI Siwen1,2, WANG Yafeng2, HE Ruijie2, DAI Tiange1,LI Dianpeng2, HUANG Yonglin2*

        ( 1. Guilin Medical University, Guilin 541004, Guangxi, China; 2. Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, Guangxi, China )

        Abstract:? Castanopsis ceratacantha contains large amounts of polyphenols and abounds in natural resources, but its chemical constituents and biological activities have not been reported. In order to clarify the chemical basis of the plant and provide scientific basis for the rational development and sustainable utilization of the plant resources. The ethanol extracts of C. ceratacantha were isolated and purified by various chromatographic methods such as Sephadex LH-20, Diaion HP20SS, and Toyopearl HW-40F to yield 11 compounds. Their structures were elucidated by spectroscopic data and comparison with literatures as gallic acid (1), caffeic acid (2), 1-(3′,4′-dihydroxycinnamoyl)-cyclopenta-2,3-diol (3), chlorogenic acid (4), chlorogenic acid methyl ester (5), kaempferol 3-O-β-D-glucuronopyranoside (6), kaempferol 3-O-{β-D-xylopyranosyl-(1→2)- [α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside} (7), quercetin 3-O-β-D-glucuronopyranoside (8) , quercetin 3-O-β-glucuronide-6″-methyl ester (9), rutin (10), and quercetin 5-O- [α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (11). All these compounds were obtained from this plant for the first time,and compounds 3, 7-11 were isolated from the genus Castanopsis for the first time.

        Key words:? Castanopsis ceratacantha, chemical constituents, structural identification, polyphenols

        殼斗科(Fagaceae)錐屬(Castanopsis)植物為常綠喬木,我國(guó)約有63種2變種,產(chǎn)長(zhǎng)江以南各地(中國(guó)科學(xué)院中國(guó)植物志編輯委員會(huì),1998)。現(xiàn)有研究表明,錐屬植物主要含有多酚類成分,具有很好的抗氧化生理活性及市場(chǎng)開發(fā)前景(王亞鳳等, 2016)。瓦山錐(Castanopsis ceratacantha)為殼斗科錐屬(Castanopsis)植物,又名瓦山栲、黃山栲等,喬木,通常高8~15 m,在我國(guó)主要分布于云南、貴州、四川等省,在老撾、泰國(guó)東北部也有分布(中國(guó)科學(xué)院中國(guó)植物志編輯委員會(huì),1998)。瓦山錐民間廣泛用于止血、止渴、止瀉(堅(jiān)果)、慢性潰瘍(葉)等疾病的治療,主要應(yīng)用在醫(yī)藥行業(yè)、食品行業(yè)、日化行業(yè)以及生化行業(yè)等領(lǐng)域。

        本實(shí)驗(yàn)選取錐屬植物瓦山錐作為研究對(duì)象,目的在于豐富錐屬植物的化學(xué)成分,掌握瓦山錐的藥效物質(zhì)基礎(chǔ),為瓦山錐的合理開發(fā)與可持續(xù)利用奠定基礎(chǔ)。此外,通過(guò)對(duì)錐屬植物瓦山錐化學(xué)成分的研究,為在經(jīng)典分類中系統(tǒng)位置有爭(zhēng)議的殼斗科植物提供依據(jù)。

        本研究以瓦山錐葉為原料,80%乙醇作為提取溶劑,通過(guò)Sephadex LH-20、Chromatorex C18、Diaion HP20SS、Toyopearl HW-40F等柱色譜層析,從瓦山錐葉乙醇提取物中分離得到11個(gè)單體化合物,經(jīng)波譜數(shù)據(jù)分析及與文獻(xiàn)比較鑒定了化合物的結(jié)構(gòu),所分離得到的成分主要為植物多酚類成分?;衔?-15結(jié)構(gòu)式見圖1所示。

        1 材料與方法

        1.1 材料和儀器

        材料于2017年8月采自云南省景洪市,經(jīng)廣西壯族自治區(qū)中國(guó)科學(xué)院廣西植物研究所丁濤副研究員鑒定為殼斗科錐屬植物瓦山錐(Castanopsis ceratacantha)的樹葉。

        Brucker Avance 500 MHz超導(dǎo)核磁共振波譜儀(瑞典Bruker);N-1100 旋轉(zhuǎn)蒸發(fā)儀(東京理化);CA-1111 冷卻水循環(huán)儀(東京理化);自動(dòng)接收儀(日本Advantec);F254硅膠薄層板(德國(guó)默克);Sephadex LH-20(GE Healthcare Bio-Science AB);Chromatorex C18(日本Fuji Silysia Chemical);Diaion HP20SS(Mistubishi Chemical);Toyopearl HW-40F(日本TOSOH公司);Sephadex LH-20(GE Healthcare Bio-Science AB);提取、分離所用試劑均為分析純。

        1.2 提取和分離

        取干燥瓦山錐葉3.5 kg,切成碎片后用80%乙醇室溫浸提2次,每次32 L,每次7 d,合并提取液并過(guò)濾,濾液經(jīng)減壓濃縮后得浸膏481.3 g。浸膏水溶解后經(jīng)Sephadex LH-20柱(8.5 cm × 40 cm)層析分離,甲醇-水(0~100%,每20%為1梯度)和60%丙酮-水溶液洗脫(每1梯度2 L),經(jīng)薄層層析分析合并,得到8個(gè)流份:Fr.1~8。Fr.1(10.0 g)經(jīng)Diaion HP20SS、Chromatorex C18、Sephadex LH-20等色譜柱反復(fù)層析分離純化得到化合物6(88 mg)、8(800 mg)、10(48 mg)。Fr.2(69.1 g)經(jīng)Diaion HP20SS、Toyopearl HW-40F等色譜柱反復(fù)層析分離純化得到化合物1(28 mg)、2(132 mg)、3(13 mg)、4(148 mg)、5(214 mg)、7(49 mg)、9(74 mg)、11(26 mg)。

        2 結(jié)構(gòu)鑒定

        化合物1 C7H6O5, 白色粉末。HR-ESI-MS

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        DU ZZ, YANG XW, HAN H, et al., 2010. A new flavone C-glycoside from Clematis rehderiana? [J]. Molecules, 5(1): 15: 672-679.

        HARI PD, SENA M, SHOJI Y, 2017. Amentoflavone and kaempferol glycosides from the aerial parts of Cissampelos pareira? [J]. Biotechnology, 5(1): 1-4.

        HE ZN, LIAN WW, LIU JW, et al., 2017. Isolation, structural characterization and neuraminidase inhibitory activities of polyphenolic constituents from Flos caryophylli? [J]. Phytochem Lett, 19: 160-167.

        Jiangsu New Medical School, 1977. Traditional Chinese Medicine Dictionary: The first and the second? [M]. Shanghai: Shanghai Peoples Publishing House.? [江蘇新醫(yī)學(xué)院, 1977, 中藥大辭典(上、下兩冊(cè))? [M]. 上海:上海人民出版社.]

        LI CD, BEI LW, JIAN MC, 2008. Flavonoid triglycosides from the seeds of Camellia oleifera Abel? [J]. Chin Chem Lett, 19: 1315-1318.

        LI S, LIU YH, 2015. Chemical constituents with antioxidative activity from the flower buds of Lonicera serreana? [J]. Guihaia, 35(4): 586-589.? [李樹, 劉玉衡, 2015. 毛藥忍冬花蕾抗氧化活性部位化學(xué)成分研究 [J]. 廣西植物, 35(4): 586-589.]

        PU SC, GUO YQ, GAO WY, et al., 2010. Chemical constituents from Hydrocotyle sibthorpioides? [J]. Chin Trad Herb Drugs, 41(9): 1440-1442.? [蒲首丞, 郭遠(yuǎn)強(qiáng), 高文遠(yuǎn), 2010. 天胡荽化學(xué)成分的研究? [J]. 中草藥, 41(9): 1440-1442.]

        WANG YF, HUANG YL, LIU JL, et al., 2016. Content and antioxidant capacity of polyhenols from the Fagaceae plants? [J]. Guangxi Sci, 23(2):180-183.? [王亞鳳, 黃永林, 劉金磊, 等, 2016. 殼斗科植物種子的多酚類含量及抗氧化能力? [J]. 廣西科學(xué), 23(2):180-183.]

        WEI H, YANG JW, YAN XJ, et al., 2018. Chemical constituents from walnut green husk: Phenols? [J]. Guihaia, 38(4): 463-468.? [魏歡, 楊建文, 顏小捷, 等, 2018. 核桃青皮的化學(xué)成分研究——酚類化合物? [J]. 廣西植物, 38(4): 463-468.]

        XU J, ZHANG TJ, GONG SX, et al., 2010. Chemical constituents from the effective hemostatic of Cirsium setosum? [J].Chin Trad Herb Drugs, 41(4): 542-544.? [許浚, 張鐵軍, 龔蘇曉, 等, 2010. 小薊止血活性部位的化學(xué)成分研究? [J]. 中草藥, 41(4): 542-544.]

        ZHU TF, LI P, SUN QW, et al., 2019. Chemical constituents from leaves of Sabia parviflora? [J]. Guihaia, 39(4): 511-515.? [朱仝飛, 李萍, 孫慶文, 等, 2019. 小花清風(fēng)藤葉的化學(xué)成分研究? [J]. 廣西植物, 39(4): 511-515.]

        (責(zé)任編輯 何永艷)

        m/z: 171.0245 [M+H]+。1H NMR (500 MHz, CD3OD) δ: 7.03 (2H, s, H-2, 6)。上述所有數(shù)據(jù)與參考文獻(xiàn)(魏歡等, 2018)比對(duì)相同,經(jīng)HPLC分析,與沒食子酸標(biāo)準(zhǔn)品保留時(shí)間一致,故鑒定化合物1為沒食子酸。

        化合物2 C9H8O4,白色粉末。1H NMR (500 MHz, CD3OD) δ: 7.64 (1H, d, J=15.9 Hz, H-7), 7.08 (1H, d, J=1.8 Hz, H-2), 6.99 (1H, dd, J=8.2, 1.8 Hz, H-6), 6.75 (1H, d, J=8.2 Hz, H-5), 6.37 (1H, d, J=15.9 Hz, H-8); 13C NMR (125 MHz, CD3OD) δ: 115.2 (C-2), 115.5 (C-5), 116.5 (C-8), 123.3 (C-6), 127.9 (C-1), 146.5 (C-7), 147.4 (C-3), 149.6 (C-4), 168.7 (C-9)。上述所有數(shù)據(jù)與參考文獻(xiàn)(朱仝飛等, 2019)比對(duì)相同,故鑒定化合物2為咖啡酸。

        化合物3 C14H16O6,淡黃色粉末。1H NMR (500 MHz, CD3OD) δ: 7.64 (1H, d, J=15.9 Hz, H-7′), 7.05 (1H, d, J=1.9 Hz, H-2′), 6.98 (1H, dd, J=8.2, 1.9 Hz, H-6′), 6.76 (1H, d, J=8.2 Hz, H-5′), 6.38 (1H, d, J=15.9 Hz, H-8′), 4.81 (1H, dd, J=9.3, 2.9 Hz, H-1), 4.31-4.26 (2H, m, H-2, 3), 2.22-1.99 (4H, m, H-4a, 4b, 5a, 5b); 13C NMR (125 MHz, CD3OD) δ: 38.5 (C-4), 42.7 (C-5), 65.6 (C-3), 69.3 (C-1), 79.5 (C-2), 115.2 (C-2′), 115.6 (C-8′), 116.1 (C-5′), 123.0 (C-6′), 127.9 (C-1′), 146.8 (C-7′), 147.1 (C-4′), 149.5 (C-3′), 169.0 (C-9′)。上述所有數(shù)據(jù)與參考文獻(xiàn)(許浚等, 2010)比對(duì)相同,故鑒定化合物3為1-(3′,4′-二羥基肉桂酰)-環(huán)戊-2,3-二酚。

        化合物4 C16H18O9,白色粉末。1H NMR (500 MHz, CD3OD) δ: 7.53 (1H, d, J=15.9 Hz, H-7), 7.04 (1H, d, J=2.0 Hz, H-2′), 6.97 (1H, dd, J=8.2, 2.0 Hz, H-6′), 6.75 (1H, d, J=8.2 Hz, H-5′), 6.23 (1H, d, J=15.9 Hz, H-8), 5.27 (1H, m, H-5), 4.11 (1H, m, H-3), 3.75 (1H, dd, J=7.6, 3.1 Hz, H-4), 2.22-2.17 (2H, m, H-2a, 6a), 2.13 (1H, dd, J=13.3, 8.3 Hz, H-2b), 2.02 (1H, dd, J=13.3, 6.6 Hz, H-6b); 13C NMR (125 MHz, CD3OD) δ: 38.0 (2C, C-2, 6), 70.4 (C-3), 72.0 (C-5), 72.6 (C-4), 75.9 (C-1), 115.1 (C-2′), 115.3 (C-8′), 116.5 (C-5′), 123.1 (C-6′), 127.2 (C-1′), 146.7 (C-3′), 147.3 (C-7′), 149.7 (C-4′), 168.6 (C-9′), 175.3 (C-7)。上述所有數(shù)據(jù)與參考文獻(xiàn)(李樹和劉玉衡,2015)比對(duì)相同,故鑒定化合物4為綠原酸。

        化合物5 C17H20O9,灰白色粉末。HR-ESI-MS m/z: 369.0948 [M+H]+。1H NMR (500 MHz, CD3OD) δ: 7.52 (1H, d, J=15.9 Hz, H-7), 7.05 (1H, d, J=1.9 Hz, H-2), 6.97 (1H, dd, J=8.2, 1.9 Hz, H-6), 6.75 (1H, d, J=8.2 Hz, H-5), 6.22 (1H, d, J=15.9 Hz, H-8), 5.33 (1H, m, H-3), 4.14 (1H, dd, J=6.6, 3.3 Hz, H-5), 3.74 (1H, dd, J=7.5, 3.1 Hz, H-4), 3.69 (3H, s, -OCH3), 2.24-2.01 (4H, m, H-2a, 2b, 6a, 6b); 13C NMR (125 MHz, CD3OD) δ: 37.8 (C-2), 38.0 (C-6), 53.0 (-OCH3), 70.4 (C-5), 72.0 (C-3), 72.6 (C-4), 75.9 (C-1), 115.0 (C-8′), 115.4 (C-2′), 116.3 (C-5′), 123.0 (C-6′), 127.2 (C-1′), 146.9 (C-3′), 147.2 (C-7′), 149.3 (C-4′), 168.6 (C-9′), 175.4 (C-7)。上述所有數(shù)據(jù)與參考文獻(xiàn)(蒲首丞等,2010)比對(duì)相同,故鑒定化合物5為綠原酸甲酯。

        化合物6 C21H18O12,淡黃色粉末。HR-ESI-MS m/z: 463.1262 [M+H]+。1H NMR (500 MHz, acetone-d6) δ: 8.16 (2H, d, J=8.9 Hz, H-2′, 6′), 6.93 (2H, d, J=8.9 Hz, H-3′, 5′), 6.56 (1H, d, J=1.9 Hz, H-8), 6.29 (1H, d, J=1.9 Hz, H-6), 5.46 (1H, d, J=7.6 Hz, H-1″), 3.87 (1H, d, J=9.7 Hz, H-5″), 3.67-3.50 (3H, m, H-2″, H-3″, 4″); 13C NMR (125 MHz, acetone-d6) δ: 72.4 (C-4″), 75.2 (C-2″), 76.4 (C-3″), 77.4 (C-5″), 94.3 (C-8), 99.9 (C-6), 104.1 (C-1″), 105.4 (C-10), 116.0 (2C, C-3′, 5′), 122.3 (C-1′), 132.2 (2C, C-2′, 6′), 135.3 (C-3), 158.0 (C-2), 158.4 (C-9), 161.0 (C-4′), 162.7 (C-5), 165.2 (C-7), 169.9 (C-6″), 178.9 (C-4)。上述所有數(shù)據(jù)與參考文獻(xiàn)(Hari et al., 2017)比對(duì)相同,故鑒定化合物6為kaempferol 3-O-β-D-glucuronopyranoside。

        化合物7 C32H38O19,黃色粉末。HR-ESI-MS m/z: 727.1855 [M+H]+。1H NMR (500 MHz, CD3OD) δ: 8.06 (2H, d, J=8.8 Hz, H-2′, 6′), 6.92 (2H, d, J=8.8 Hz, H-3′, 5′), 6.43 (1H, d, J=2.1 Hz, H-8), 6.21 (1H, d, J=2.1 Hz, H-6), 5.41 (1H, d, J=7.5 Hz, H-1″), 4.78 (1H, d, J=7.0 Hz, H-1), 4.50 (1H, s, H-1″″), 1.09 (3H, d, J=6.2 Hz, H-6″″); 13C NMR (125 MHz, CD3OD) δ: 17.8 (C-6″″), 66.6 (C-5), 68.1 (C-6″), 69.7 (C-5″″), 71.0 (C-4″), 71.4 (C-4), 72.1 (C-3″″), 72.3 (C-2″″), 73.9 (C-4″″), 74.7 (C-2), 76.9 C-3), 77.1 (C-5″), 78.2 (C-3″), 82.0 (C-2″), 94.2 (C-8), 99.5 (C-6), 100.7 (C-1″), 102.4 (C-1″″), 105.2 (C-1), 105.7 (C-10), 116.2 (2C, C-3′, 5′), 122.9 (C-1′), 132.4 (2C, C-2′, 6′), 134.8 (C-3), 158.5 (C-2), 158.7 (C-9), 161.2 (C-4′), 163.4 (C-5), 165.7 (C-7), 179.5 (C-4)。上述所有數(shù)據(jù)與參考文獻(xiàn)(Li et al., 2008)比對(duì)相同,故鑒定化合物7為kaempferol 3-O-{β-D-xylopyranosyl-(1→2)- [α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside}。

        化合物8 C21H18O13,黃色粉末。HR-ESI-MS m/z: 479.0548 [M+H]+。1H NMR (500 MHz, CD3OD) δ: 7.66 (1H, d, J=2.2 H-2′), 7.64 (1H, dd, J=8.6, 2.2 Hz, H-6′), 6.87 (1H, d, J=8.6 Hz, H-5′), 6.38 (1H, d, J=2.0 Hz, H-8), 6.19 (1H, d, J=2.0 Hz, H-6), 5.34 (1H, d, J=7.7 Hz, H-1″), 3.76 (1H, d, J=9.7 Hz, H-5″), 3.61-3.46 (3H, m, H-2″, 3″, 4″); 13C NMR (125 MHz, CD3OD) δ: 72.8 (C-4″), 75.4 (C-2″), 77.0 (C-3″), 77.6 (C-5″), 94.8 (C-8), 100.0 (C-6), 104.2 (C-1″), 105.6 (C-10), 116.0 (C-2′), 117.3 (C-5′), 122.8 (C-6′), 123.5 (C-1′), 135.4 (C-3), 145.9 (C-3′), 150.2 (C-4′), 158.1 (C-2), 159.1 (C-9), 162.6 (C-5), 165.9 (C-7), 172.3 (C-6″), 179.2 (C-4)。上述所有數(shù)據(jù)與參考文獻(xiàn)(Du et al., 2010)比對(duì)相同,故鑒定化合物8為quercetin 3-O-β-D-glucuronopyranoside。

        化合物9 C22H20O13,黃色無(wú)晶形粉末。HR-ESI-MS m/z: 493.0742 [M+H]+。1H NMR (500 MHz, CD3OD) δ: 7.60 (1H, d, J=2.2 H-2′), 7.56 (1H, dd, J=8.5, 2.2 H-6′), 6.83 (1H, d, J=8.5 Hz, H-5′), 6.40 (1H, br s, H-8), 6.20 (1H, br s, H-6), 5.25 (1H, d, J=7.8 Hz, H-1″), 3.80 (1H, d, J=9.7 Hz, H-5″), 3.68 (3H, s, 6″-OCH3), 3.61-3.47 (3H, m, H-2″, 3″, 4″); 13C NMR (125 MHz, CD3OD) δ: 52.9 (6″-OCH3), 72.7 (C-4″), 75.3 (C-2″), 77.0 (C-5″), 77.3 (C-3″), 94.5 (C-8), 99.9 (C-6), 104.6 (C-1″), 105.5 (C-10), 115.9 (C-5′), 117.3 (C-2′), 122.8 (C-1′), 123.5 (C-6′), 135.4 (C-3), 145.9 (C-3′), 149.8 (C-4′), 158.1 (C-9), 159.3 (C-2), 162.9 (C-5), 166.4 (C-7), 170.9 (C-6″), 179.2 (C-4)。上述所有數(shù)據(jù)與參考文獻(xiàn)(He et al., 2017)比對(duì)相同,故鑒定化合物9為quercetin 3-O-β-glucuronide-6″-methyl ester。

        化合物10 C27H30O16,淡黃色粉末。HR-ESI-MS m/z: 611.1935 [M+H]+。1H NMR (500 MHz, acetone-d6) δ: 7.72 (1H, d, J=2.2 Hz, H-2′), 7.67 (1H, dd, J=8.5, 2.2 Hz, H-6′), 6.93 (1H, d, J=8.5 Hz, H-5′), 6.49 (1H, d, J=2.1 Hz, H-8), 6.31 (1H, d, J=2.1 Hz, H-6), 5.12 (1H, d, J=7.3 Hz, H-1″), 4.53 (1H, d, J=1.8 Hz, H-1), 1.06 (3H, d, J=6.5 Hz, H-6), 3.74-3.30 (10H, m, H-2″, 3″, 4″, 5″, 6a″, 6b″, 2, 3, 4, 5); 13C NMR (125 MHz, acetone-d6) δ: 17.7 (C-6), 67.5 (C-6″), 69.0 (C-5), 70.3 (C-4″), 71.2 (C-3), 71.6 (C-2), 73.0 (C-4), 74.9 (C-3″), 76.3 (C-2″), 77.4 (C-5″), 94.5 (C-8), 99.9 (C-6), 101.7 (C-10), 104.4 (C-1), 104.8 (C-1″), 115.8 (C-5′), 117.4 (C-2′), 122.3 (C-1′), 123.1 (C-6′), 135.0 (C-3), 145.2 (C-3′), 149.2 (C-4′), 157.7 (C-2), 158.6 (C-5), 161.9 (C-9), 165.3 (C-7), 178.6 (C-4)。上述所有數(shù)據(jù)與參考文獻(xiàn)(陳秋虹等,2017)比對(duì)相同,故鑒定化合物10為蘆丁。

        化合物11 C27H30O16,淡黃色粉末。HR-ESI-MS m/z: 611.1472 [M+H]+。1H NMR (500 MHz, CD3OD) δ: 7.67 (1H, d, J=1.9 Hz, H-2′), 7.61 (1H, dd, J=8.5, 1.9 Hz, H-6′), 6.85 (1H, d, J=8.5 Hz, H-5′), 6.40 (1H, d, J=1.9 Hz, H-8), 6.21 (1H, d, J=1.9 Hz, H-6), 5.11 (1H, d, J=7.7 Hz, H-1″), 4.52 (1H, br s, H-1), 3.80 (1H, d, J=10.9 Hz, H-6a″), 3.63 (1H, m, H-3), 3.52-3.26 (8H, m, H-2″, 3″, 4″, 5″, 6b″, 2, 4, 5); 13C NMR (125 MHz, CD3OD) δ: 17.9 (C-6), 68.6 (C-6″), 69.7 (C-5), 71.4 (C-4″), 72.1 (C-3), 72.3 (C-2), 73.9 (C-4), 75.7 (C-2″), 77.2 (C-5″), 78.2 (C-3″), 94.9 (C-8), 100.0 (C-6), 102.4 (C-1), 104.6 (C-1″), 105.8 (C-10), 116.1 (C-5′), 117.9 (C-2′), 123.1 (C-1′), 123.6 (C-6′), 135.6 (C-3), 145.9 (C-4′), 149.8 (C-3′), 158.7 (C-9), 159.1 (C-2), 163.0 (C-7), 166.4 (C-5), 179.1 (C-4)。上述所有數(shù)據(jù)與參考文獻(xiàn)(Bina et al., 2012)比對(duì)相同,故鑒定化合物11為quercetin 5-O- [α-L-rhamnopyranosyl- (1→6)]-β-D-glucopyranoside。

        3 討論

        本研究從瓦山錐干燥的樹葉醇提取物中分離鑒定了11個(gè)植物多酚類成分,包括1個(gè)沒食子酸類化合物、2個(gè)奎寧酸類化合物、2個(gè)咖啡酸類化合物、6個(gè)黃酮類化合物,所有化合物均為首次從瓦山錐植物中分離得到。本課題組系統(tǒng)地進(jìn)行了廣西常見的殼斗科植物南嶺栲、紅栲、甜櫧、飯甑青岡、鉤錐、瓦山錐等植物的化學(xué)成分研究,從南嶺栲、紅栲、甜櫧、鉤錐中得到錐屬植物中特有的特征性三萜鞣花單寧成分,為在經(jīng)典分類中系統(tǒng)位置有爭(zhēng)議的殼斗科植物錐屬的系統(tǒng)位置提供了直接的化學(xué)證據(jù)。瓦山錐中暫未分離得到特征性三萜鞣花單寧成分,但含有大量原花青素類多聚體化合物。此類多聚體多為結(jié)構(gòu)相近、極性相似的化合物,較難分離,本實(shí)驗(yàn)通過(guò)Sephadex LH-20、Chromatorex C18等柱色譜反復(fù)分離提取得到三個(gè)此類化合物,目前化合物的結(jié)構(gòu)正在鑒定當(dāng)中。本實(shí)驗(yàn)為植物多酚類成分的分離純化積累經(jīng)驗(yàn),為瓦山錐植物的合理開發(fā)與可持續(xù)利用提供了科學(xué)依據(jù)。

        參考文獻(xiàn):

        BINA SS, NASIMA K, SABIRA B, et al., 2012. Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity? [J]. Phytochemistry, 77: 238-244.

        CHEN QH, HUANG Y, ZHOU JJ, et al., 2017. Chemical constituents from leaves of Camellia nitidissima var. longistyla (II)? [J]. Chin Trad Herb Drugs, 48(23): 4845-4850.? [陳秋虹, 黃艷, 周潔潔, 等, 2017. 長(zhǎng)柱金花茶葉的化學(xué)成分研究(II) [J]. 中草藥, 48(23):? 4845-4850.]

        Chinese Botanical Society Editorial Board of Chinese Academy of Sciences, 1998. Flora Reipublicae Popularis Sinicae? [M]. Beijing: Science Press, 22:13, 69.? [中國(guó)科學(xué)院中國(guó)植物志編輯委員會(huì), 1998. 中國(guó)植物志 [M]. 北京: 科學(xué)出版社, 22: 13, 69.]

        DU ZZ, YANG XW, HAN H, et al., 2010. A new flavone C-glycoside from Clematis rehderiana? [J]. Molecules, 5(1): 15: 672-679.

        HARI PD, SENA M, SHOJI Y, 2017. Amentoflavone and kaempferol glycosides from the aerial parts of Cissampelos pareira? [J]. Biotechnology, 5(1): 1-4.

        HE ZN, LIAN WW, LIU JW, et al., 2017. Isolation, structural characterization and neuraminidase inhibitory activities of polyphenolic constituents from Flos caryophylli? [J]. Phytochem Lett, 19: 160-167.

        Jiangsu New Medical School, 1977. Traditional Chinese Medicine Dictionary: The first and the second? [M]. Shanghai: Shanghai Peoples Publishing House.? [江蘇新醫(yī)學(xué)院, 1977, 中藥大辭典(上、下兩冊(cè))? [M]. 上海:上海人民出版社.]

        LI CD, BEI LW, JIAN MC, 2008. Flavonoid triglycosides from the seeds of Camellia oleifera Abel? [J]. Chin Chem Lett, 19: 1315-1318.

        LI S, LIU YH, 2015. Chemical constituents with antioxidative activity from the flower buds of Lonicera serreana? [J]. Guihaia, 35(4): 586-589.? [李樹, 劉玉衡, 2015. 毛藥忍冬花蕾抗氧化活性部位化學(xué)成分研究 [J]. 廣西植物, 35(4): 586-589.]

        PU SC, GUO YQ, GAO WY, et al., 2010. Chemical constituents from Hydrocotyle sibthorpioides? [J]. Chin Trad Herb Drugs, 41(9): 1440-1442.? [蒲首丞, 郭遠(yuǎn)強(qiáng), 高文遠(yuǎn), 2010. 天胡荽化學(xué)成分的研究? [J]. 中草藥, 41(9): 1440-1442.]

        WANG YF, HUANG YL, LIU JL, et al., 2016. Content and antioxidant capacity of polyhenols from the Fagaceae plants? [J]. Guangxi Sci, 23(2):180-183.? [王亞鳳, 黃永林, 劉金磊, 等, 2016. 殼斗科植物種子的多酚類含量及抗氧化能力? [J]. 廣西科學(xué), 23(2):180-183.]

        WEI H, YANG JW, YAN XJ, et al., 2018. Chemical constituents from walnut green husk: Phenols? [J]. Guihaia, 38(4): 463-468.? [魏歡, 楊建文, 顏小捷, 等, 2018. 核桃青皮的化學(xué)成分研究——酚類化合物? [J]. 廣西植物, 38(4): 463-468.]

        XU J, ZHANG TJ, GONG SX, et al., 2010. Chemical constituents from the effective hemostatic of Cirsium setosum? [J].Chin Trad Herb Drugs, 41(4): 542-544.? [許浚, 張鐵軍, 龔蘇曉, 等, 2010. 小薊止血活性部位的化學(xué)成分研究? [J]. 中草藥, 41(4): 542-544.]

        ZHU TF, LI P, SUN QW, et al., 2019. Chemical constituents from leaves of Sabia parviflora? [J]. Guihaia, 39(4): 511-515.? [朱仝飛, 李萍, 孫慶文, 等, 2019. 小花清風(fēng)藤葉的化學(xué)成分研究? [J]. 廣西植物, 39(4): 511-515.]

        (責(zé)任編輯 何永艷)

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