牛筋果的生理活性成分研究
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摘要
本文分为两部分,第一部分概述了苦木科(Simaroubaceae)牛筋果属(Harrisonia)植物化学成分及药理活性研究进展。20世纪80年代初至今,前人已对牛筋果属(Harrisonia)植物中色原酮类、苦木素类、聚酮类、三萜类等有效化学成分及其抗肿瘤、抗疟、抗氧化和昆虫拒食活性等多种药理活性进行了研究。
第二部分对苦木科(Simaroubaceae)牛筋果属Harrisonia)植物牛筋果[(Harrisonia perforata (Blanco) Merr.)]果实的乙醇提取物中的化学成分及其抗氧化活性和抗肿瘤活性进行了研究。
1、在活性筛选指导下,从该植物果实的乙醇提取物中分离得到18个化合物,运用现代波谱分析技术鉴定了12个化合物：Ethyl 3,4,5-Trihdroxybenzoate(1)、4-ethylgallic acid(2)、Hydroxyhydroquinone(3)、Gallic acid(4)、β-Sitosterol(5)、β-Daucosterol(6)、Stigmasterol(7)、Protocatechuic acid(8)、Palmitic acid(9)、Linoleic acid(10)、Cis-Oleic acid(11)、5-hydroxymethyl-2-Furancarboxaldehyde(12);化合物1-12均为首次在该植物果实中分离得到。
2、用DPPH法进行抗氧化活性测试,结果表明其醇提物部分、石油醚部分、乙酸乙酯部分具有较强的抗氧化活性；在活性追踪指导下,对单体化合物进行抗氧化活性测试,结果表明化合物1、2、3、4、8具有较强抗氧化活性。
3、用MTT法对牛筋果果实乙醇提取物进行体外活性筛选,结果表明醇提物部分、石油醚部分、乙酸乙酯部分对人慢性髓原白血病细胞(K562)及人胃癌细胞(SGC-7901)均未表现出明显的生长抑制活性。
4、采用气相色谱-质谱联用技术(GC-MS)对牛筋果果实脂溶性进行分析,确认了其果实石油醚部分29种成分(占总量的69.67%),其含量较高的成分依次为顺-9,12-十八碳二烯醇(12.35%)、棕榈酸(9.67%)、Z-9,17-十八碳烯醛(8.97%)、油酸乙酯(5.81%)、β谷甾醇(4.88%)、亚油酸乙酯(4.10%)；其乙醇粗提物的脂溶性成分共确认了其中的12种成分(占总量的71.00%),其中含量较高的成分依次为奎尼酸(40.44%)、焦桔酸(14.64%)、5-羟甲基-2-呋喃甲醛(5.89%)。
The thesis consists of two parts. The first part is a review of the research progress of chemical constituents and their bioactives from the plants of the genus of Harrisonia R. Br.. There have been many researches about the fruits of [Harrisonia perforata (Blanco) Merr.] since 1980s. In recent several decades, chromones, triterpenoids, limonoids and prenylated polyketides with various bioactivities have been reported from H. Perforata.
The second part is about the antioxidant and anti-tumor activity constituents from the ethanol extract of the fruits of H. Perforata.
1、Bioassay-guided fractionation led to the isolation of 18 compounds from the ethanol extract of H. Perforata,12 compounds structures were unambiguously elucidated as Ethyl 3,4,5-Trihdroxybenzoate (1)、4-ethylgallic acid (2)、Hydroxyhydroquinone (3)、Gallic acid (4)、β-Sitosterol (5)、β-Daucosterol (6)、Stigmasterol (7)、Protocatechuic acid (8)、Palmitic acid (9)、Linoleic acid (10)、Cis-Oleic acid (11)、5-hydroxymethyl-2-Furancarboxaldehyde (12), and all of them were isolated from the fruits of the H. Perforata for the first time.
2、With bioassay-guiding, the parts of Petroleum Ether extract, Ethyl Acetate extract and Ethanol extract possessed high antioxidant activity by DPPH free radical scavenging method; and compounds 1、2、3、4、8 showed high antioxidant activity respectively.
3、In our screening for bioactive agents from tropical medicinal plants, the parts of Petroleum Ether extract, Ethyl Acetate extract and Ethanol extract of the fruits from H. Perforata did not show cytotoxic activity towards human chronic myelogenous leukemia (K562) and human gastric cancer (SGC-7901) cell lines in vitro by MTT method.
4、This is the first report of gas chromatography-mass spectrometry of chemical constituents from the petroleum ether fraction and alcohol extraction of the fruits of H. Perforata, and the constituents were identified by their mass spectra. In the petroleum ether extraction,29 compounds were identified, amounting to 69.67% of the total detected constituents. The major constituents were identified as Z-9,12-Octadecadien-1-ol (12.35%), Palmitic acid (9.67%), Z-9,17-octadecadienal (8.97%), Ethyl Oleate (5.81%),β-Stitosterol (4.88%), Ethyl Linoleate (4.10%). From the alcohol extraction,12 compounds were identified, amounting to 71.00% of the total detected constituents. The major constituents were identified as Quinic acid (40.44%), pyrogallol (14.64%),5-(hydroxymethyl)-2-Furancarboxaldehyde (5.89%).
第二部分对苦木科(Simaroubaceae)牛筋果属Harrisonia)植物牛筋果[(Harrisonia perforata (Blanco) Merr.)]果实的乙醇提取物中的化学成分及其抗氧化活性和抗肿瘤活性进行了研究。
1、在活性筛选指导下,从该植物果实的乙醇提取物中分离得到18个化合物,运用现代波谱分析技术鉴定了12个化合物：Ethyl 3,4,5-Trihdroxybenzoate(1)、4-ethylgallic acid(2)、Hydroxyhydroquinone(3)、Gallic acid(4)、β-Sitosterol(5)、β-Daucosterol(6)、Stigmasterol(7)、Protocatechuic acid(8)、Palmitic acid(9)、Linoleic acid(10)、Cis-Oleic acid(11)、5-hydroxymethyl-2-Furancarboxaldehyde(12);化合物1-12均为首次在该植物果实中分离得到。
2、用DPPH法进行抗氧化活性测试,结果表明其醇提物部分、石油醚部分、乙酸乙酯部分具有较强的抗氧化活性；在活性追踪指导下,对单体化合物进行抗氧化活性测试,结果表明化合物1、2、3、4、8具有较强抗氧化活性。
3、用MTT法对牛筋果果实乙醇提取物进行体外活性筛选,结果表明醇提物部分、石油醚部分、乙酸乙酯部分对人慢性髓原白血病细胞(K562)及人胃癌细胞(SGC-7901)均未表现出明显的生长抑制活性。
4、采用气相色谱-质谱联用技术(GC-MS)对牛筋果果实脂溶性进行分析,确认了其果实石油醚部分29种成分(占总量的69.67%),其含量较高的成分依次为顺-9,12-十八碳二烯醇(12.35%)、棕榈酸(9.67%)、Z-9,17-十八碳烯醛(8.97%)、油酸乙酯(5.81%)、β谷甾醇(4.88%)、亚油酸乙酯(4.10%)；其乙醇粗提物的脂溶性成分共确认了其中的12种成分(占总量的71.00%),其中含量较高的成分依次为奎尼酸(40.44%)、焦桔酸(14.64%)、5-羟甲基-2-呋喃甲醛(5.89%)。
The thesis consists of two parts. The first part is a review of the research progress of chemical constituents and their bioactives from the plants of the genus of Harrisonia R. Br.. There have been many researches about the fruits of [Harrisonia perforata (Blanco) Merr.] since 1980s. In recent several decades, chromones, triterpenoids, limonoids and prenylated polyketides with various bioactivities have been reported from H. Perforata.
The second part is about the antioxidant and anti-tumor activity constituents from the ethanol extract of the fruits of H. Perforata.
1、Bioassay-guided fractionation led to the isolation of 18 compounds from the ethanol extract of H. Perforata,12 compounds structures were unambiguously elucidated as Ethyl 3,4,5-Trihdroxybenzoate (1)、4-ethylgallic acid (2)、Hydroxyhydroquinone (3)、Gallic acid (4)、β-Sitosterol (5)、β-Daucosterol (6)、Stigmasterol (7)、Protocatechuic acid (8)、Palmitic acid (9)、Linoleic acid (10)、Cis-Oleic acid (11)、5-hydroxymethyl-2-Furancarboxaldehyde (12), and all of them were isolated from the fruits of the H. Perforata for the first time.
2、With bioassay-guiding, the parts of Petroleum Ether extract, Ethyl Acetate extract and Ethanol extract possessed high antioxidant activity by DPPH free radical scavenging method; and compounds 1、2、3、4、8 showed high antioxidant activity respectively.
3、In our screening for bioactive agents from tropical medicinal plants, the parts of Petroleum Ether extract, Ethyl Acetate extract and Ethanol extract of the fruits from H. Perforata did not show cytotoxic activity towards human chronic myelogenous leukemia (K562) and human gastric cancer (SGC-7901) cell lines in vitro by MTT method.
4、This is the first report of gas chromatography-mass spectrometry of chemical constituents from the petroleum ether fraction and alcohol extraction of the fruits of H. Perforata, and the constituents were identified by their mass spectra. In the petroleum ether extraction,29 compounds were identified, amounting to 69.67% of the total detected constituents. The major constituents were identified as Z-9,12-Octadecadien-1-ol (12.35%), Palmitic acid (9.67%), Z-9,17-octadecadienal (8.97%), Ethyl Oleate (5.81%),β-Stitosterol (4.88%), Ethyl Linoleate (4.10%). From the alcohol extraction,12 compounds were identified, amounting to 71.00% of the total detected constituents. The major constituents were identified as Quinic acid (40.44%), pyrogallol (14.64%),5-(hydroxymethyl)-2-Furancarboxaldehyde (5.89%).
引文
[1]吴征镒,周太炎,肖培根主编.新华本草纲要.上海：科学技术出版社,1988.75.
[2]谭庆伟,吴祖建,欧阳明安.臭椿化学成分及生物活性研究进展[J].天然产物研究与开发,2008,20：748-755.
[3]林隆泽,张金生,陈仲良等.鸦胆子化学成分的研究(Ⅰ.鸦胆子酮酸等五个苦木素的分离和鉴定)[J].化学学报,1982,40(1),73-78.
[4]顶晨旭,索有瑞.中药鸦胆子化学成分及药理学研究进展,2006,28(1)：117-120.
[5]王玫馨,张敏生,朱元龙等.草药牛筋果化学成分的研究.药学学报,1984,19(10)：760-763.
[6]王玫馨,张敏生,朱元龙.草药牛筋果化学成分的研究.药学学报,1983,18(2)：113-118.
[7]卫新成,金祥林,顾孝诚等.牛筋果有效成分牛晶Ⅰ的分子和晶体结构.北京大学学报(自然科学版)1986,4,15-20.
[8]卫新成,潘佐华,顾孝诚.草药牛筋果化学成分的研究Ⅳ牛晶Ⅴ的分子晶体结构.结构化学.1985,4(4)：281-287.
[9]中国科学院中国植物志编辑委员会.中国植物志.第四十三卷.第三分册.北京：科学出版社,1997.15
[10]马汉铭,杜平华.数理医药学杂志.2002,15(2)：158.
[11]谷华,王梅,王志阳.中医研究,2001,14(5)：55-56.
[12]吴元德等：苯并芘自由基中间产物酶代谢研究.第四届全国生物物理学学术会议论之摘要汇编(上),P72,1983.
[13]Ju J H(鞠建华),Yang J S(杨峻山),Liu D(刘东).Study on thechemical components of Beesia calthaifolia Ⅱ[J]. Chin Pharm J(中国药学杂志),2000,35 (3):157-160. (in Chinese).
[14]Zhang W J(张雯洁),Liu Y Q(刘玉清),Li X C(李兴从),et al. Chemical constituents of "Ecological Tea" from Yunnan [J]. Acta Bot Yunnan(云南植物研 究),1995,17(5)：204-208.(in Chinese).
[15]闫利华,徐丽珍,邹忠梅.小木通茎的化学成分研究(Ⅰ).中草药,2007,38(3)：340-342.
[16]Dai H F(戴好富),Zhou J(周俊),Peng Z G(彭再刚),et al.Studieson the chemical constituents of Scisandra chinensis [J]. Nat ProdRes Devlop(天然产物研究与开发),2001,13(1)：24-26.(in Chinese)
[17]杨虹,王峥涛,胡之璧,等.半夏的化学成分研究[J].中国药学杂志,2007,42(2)：101.
[18]戴好富,梅文莉,曾艳波,等.红树林植物木果楝细胞毒活性和化学成分研究.天然产物研究与开发,2007,19(1)：74-76.
[19]TRAN VAN SUNG, NGUYEN MiNH PHUONG, CHRISTINE KANMPERDICK, et al. (1995). PERFORATINOLONE, A LIMONOID FROM HARRISONIA PERFORATA. Phytochemistey.38(1), pp.213-215.
[20]TOMOKO TANAKA, KAZUO KOIKE, KATSUYOSHI MITSUNAGA, et al. (1995). CHROMONES FROM HARRISONIA PERFORATA. Phytochemistry, 40(6), pp.1787-1790.
[21]Tripetch K, Ryoji K, Phannipha C, et al. Phytochemistry,2001,56 (2): 383～386.
[22]Simon G, Lyn C, Clyde D, et al. Phytochemistry,1997,44 (6):1109～1114.
[23]Sheng Yin, Xin Chen, Zu-Shang Su, et al. Harrisotones A-E, five novel prenylated polyketides with a rare spirocyclic skeleton from Harrisonia perforate. Tetrahedron 65 (2009) 117-1152.
[24]Qui Khuong-Huu, Angele Chiaroni, Claude Riche, et al. New Rearranged Limonoids from Harrisonia perforate. J. Nat. Prod.2000,63,1015-1018.
[25]Petelot, A. Les plantes medicinales du Cambodge, Du Laos et du Viet-Nam, Archives des Recherches Agronomiques au Cambodge, au Laos et an Viet-Nam 1952; Vol.Ⅰ. p 169.
[26]Penso, G. Inventaire des Plants medicinales employees dans les differents pays, O. M. S. DPM/80.3.
[27]Tuntiwachwuttiku Pittaya, Phansa Photchana, Pootaeng-On Yupa, et al. Chromones from the braches of Harrisonia perforata. Chemical & Pharmaceutical Bulletin,2006,54 (1):44～47.
[28]Byrne, L.T., Tri, M.V., Phuong, N. M., Sargent, M.V., Skelton, B.W. and White, A.H. (1991) Aust.J.Chem.44,165.
[29]Chanpagne, D. E., Koul,O., Isman, M.B., Scudder, G. G. E. and TOWERS, G. H. N.(1992) Phytochemistry 31,377.
[30]Mitsunaga, K., Koike, K., Ishii, K. and Ohmoto, T. (1994) Phytochemistey 35,451.
[31]Qui Khuong-Huu, Angele Chiaroni, Claude Riche, et al. New Rearranged Limonoids from Harrisonia perforate.Ⅲ. J. Nat. Prod.2001,64,634-637.
[32]Chiaroni, A.; Riche, C.; Khuong-Huu, Q.; Nguyen-Ngoc, H.; Nguyen-Viet, K.; Khuong-Huu, F. Acta Crystallogr.2000, C56,711-713.
[33]Wei, X.; Pan, Z.; Gu, X.; Wang, M.; Zhu, Y. Jiegou Huaxue 1985, 4,281-287.(5), Byrne, L. T.; Van Tri, M.; Nguyen-Minh, P.; Sargent, M. V.; Skelton, B. W.; White, A. H. Austr. J. Chem.1991,44,165-169.
[34]TranVan, S.; Nguyen-Minh, P.; Kamperdick, C.; Adam, G. Phytochemistry 1995,38,213-215.
[35]Kamiuchi, K.; Mitsunaga, K.; Koike, K.; Ouyang, Y.; Ohmoto, T.; Nikaido, T. Heterocycles 1996,43,653-664.
[36]Angele Chiaroni, Claude Riche, Qui Khuong-Huu, et al. New Limonoids from Harrisonia Perforata (Blanco) Merr. Acta Cryst. (2000). C56,711-713.
[37]Khuong-Huu Q.; Chiaroni, A.; Riche, C.; Nguyen-Ngoc, H.; Nguyen-Viet, K.; Khuong-Huu, F. J. Nat. Prod.2000,63,1015-1018.
[38]Perry Lily May. Medicinal Plants of East and Southeast Asia:Attributed Properties and Uses. America, Massachusetts, Cambridge:Massachusetts Institute of Technology Press,1980.389.
[39]Bremner J B. New alkaloids with potential biological activity. In: Proceedings of the 7th Asian Symposium on Medicinal Plants, Spices and Other Natural Products. Philippines, Manila:ASOMPS,1992.75.
[40]Grieco P A, Haddad J, Pineiro-Nunez M M, et al. Phytochemistry,1999, (4): 575-578.
[41]Carmen G, Azucena GC, et al. Industrial Crops and Products,1999,10 (1): 35-40.
[42]F.B. Magassouba, A. Diallo, M. Kouyate, et al. Ethnobotanical survey and antibacterial activity of some plants used in Guinean traditional medicine. Journal of Ethnopharmacology 114 (2007) 44-53.
[43]Aun Chea, Marie-Caroline Jonville, Sok-Siya Bun et al.2007. In vitro Antimicrobial Activity of Plants used in Cambodian Teaditional Medicine. The American Journal of Chinese Medicine, Vol.35, No.5,867-873.
[44]Werner Fabry, Paul O. Okemo, Rainer Ansorg. Antibacterial activity of East African medicinal plants. Journal of Ethnopharmacology 60 (1998) 79-84.
[45]Jittra Limsong, E. Benjavongkulchai, Jintakorn Kuvatanasuchati. Inhibitory effect of some herbal extracts on adherence of Streptococcus mutans. Journal of Ethnopharmacology 92 (2004) 281-289.
[46]Julie Nguyen-Pouplin, Hop Tran, Hung Tran, et al.Antimalarial and cytotoxic activities of ethnopharmacologically selected medicinal plants from South Vietnam. Journal of Ethnopharmacology 109 (2007) 417-427.
[47]Tanaka, T., Koike, K., Mitsunaga, K., Narita, K., Takano, S., Kamioka, A., Sase, E., Ouyang, Y., Ohmoto, T.,1995. Chromones from Harrisonia perforata. Phytochemistry 40,1787-1790.
[48]Kamiuchi, K., Mitsunaga, K., Koike, K., Ouyang, Y., Ohmoto, T., Nikaido, T.,1996. Quassinoids and limonoids from Harrisonia perforata. Heterocycles 43, 653-664.
[49]Murakami, N., Sugimoto, M., Kawanishi, M., Tamura, S., Kim, H.S., Begum, K., Wataya, Y., Kobayashi, M.,2003. New semisynthetic quassinoids with in vivo antimalarial activity. Journal of Medicinal Chemistry 46,638-641.
[50]Krief, S., Martin, M.T., Grellier, P., Kasenene, J., Sevenet, T.,2004. Novel antimalarial compounds isolated in a survey of self-medicative behavior of wild chimpanzees in Uganda.Antimicrobial Agents and Chemotherapy 48,3196-3199.
[51]Ahmed El Tahir, Gwiria M.H. Satti, Sami A. Khalid. Antiplasmodial activity of selected Sudanese medicinal plants with emphasis on Maytenus senegalensis (Lam.) Exell. Journal of Ethnopharmacology 64 (1999) 227-233.
[52]AHMED HASSANALI, MICHAEL D. BENTLEY, ALEXANDRA M. Z. SLA WIN et al. PEDONIN, A SPIRO TETRANORTRITERPENOID INSECT ANTIFEEDANT FROM HARRISONIA ABYSSINICA. Phyrochemimy, Vol.26. No.2, pp.573-575.1987.
[53]B.K. MEHTA, KM. SAVITA SHARMA and AVINASFH DUBEY. 4-ETHYLGALLIC ACID FROM TWO MIMOSA SPECIES. Phgtochemistry. Vol.27, No.9, pp.3004-3005.1988.
[54]Jiwajinda S, Santisopasri V, Murakami A, et al. Jethnopharmacology,2002, 82(1):55-58.
[55]Morre D J, Grieco P A, Morre D M, et al. Life Sci,1998,63 (7):595-604.
[56]Tamura S, Fukamiya N, Okano M, et al. Three new quassinoids, ailantinol E, F, and G, from Ailanthus altissim a. ChemPharm Bull,2003,51:385-389.
[57]Seida A A, Kinghorn A D, Cordell G A, et al. Potential anticancer agents. Isolation of a new simaroubolide,6α-tigloy-loxychaparrinone, from Ailanthus integrifolia ssp. Calycina (Simaroubaceae). Lloydia,1978,41:584-587.
[58]O'NeillM, Bray DH, Boardman P, et al. Plants as sources of antimalarial drugs:In vitro antimalarial activities of some quassinoids. Antim icrob Agents Chem other,1986,30:101-104.
[59]Ohmoto T, Sung YI. Antimycotic substances in the crude drugs Ⅱ. Shoyakugaku Zasshi,1982,36:307-314
[60]Mergen F. Atoxic principle in the leaves of Ailanthus. Bot Gaz,1959,121: 32-36.
[61]Lin L J, Peiser G, YingB P, et al. Identification of plant growthinhibitory p rincip les in Ailanthus altissima and Castela tortuosa. J Agric Food Chem,1995, 43:1708-1711.
[62]De Feo V, De Martino L, Santoro A, et al. Antiproliferative effects of tree of heaven(Ailanthus altissima Swingle). Phytother Res,2005,3:226-230.
[63]Tsao R, Romanchuk F E, Peterson C J, et al. Plant growth regulatory effect and insecticidal activity of the extracts of the tree of Heaven(Ailanthus altissima L.). BMC Ecology,2002,2:1.
[64]De Feo V, De Martino L, Quaranta E, et al. Isolation of phytotoxic compounds from tree-of-heaven (Ailanthus altissim aswingle). J Agric Food Chem,2003,51:1177-1180.
[65]Casinovi C G, Ceccherelli P, Fardella G, et al. Isolation and structure of a quassinoid from Ailanthus glandulosa. Phytochemistry,1983,22:2871-2873.
[66]Xu S H(许申鸿),Hang H(杭湖).A simple method for the screening of free radical scavenger [J]. Chin Trad Herb Drugs(中草药),2000,31 (2):96-97. (in Chinese)
[67]Xu S H(许申鸿),Hang H(杭湖).Preliminarily study on DPPH assay by spectrophotometry and its application [J]. Plant Physiol Commun(植物生理学通讯),1999,35(6)：472-477.(in Chinese)
[68]Chen C J(陈丛瑾),Huang K Y(黄克瀛),Sun C L(孙崇鲁).Study on DPPH free radicals scavenging activity of Solanum lyratum Thumb fruit extractives [J]. Food Res Develop(食品研究与开发),2006,27 (10):45-48. (in Chinese)
[69]Ang H H, Hitotsuyanagi Y, Fukaya H, et al. Tetrahedron Letters,2000,41(7): 6849～6853.
[70]Ang H H, Hitotsuyanagi Y, Fukaya H, et al. Phytochemistry,2002,59 (8): 833～837.
[71]Zahid L, Lyn C, Hartley TG, et al. Biochemical systematics and Ecology, 2000,28(2):183～184.
[72]Fernando M, Luko H, Gerardo A M, et al. Crop Protection,2000,19(3): 301～305.
[73]Tamuraa S, Fukamiyaa N, Okano M, et al. Cancer chemopreventive effect of quassinoid derivatives. Introduction of side chain to shinjulactone C for enhancement of inhibitory effect on Epstein-Barr virus activation [J]. Cancer Lett, 2002,185(1):471.
[74]Mata-Greenwood E, Cuendet M, Sher D, et al. Brusatol-mediated induction of leukemic cell differentiation and G1 arrest asscciated wit h down-regulation of cmyc [J]. Leukemia,2002,16 (11):2275.
[75]Takeya K, Kobata H, Ozeki A, et al. Quassinoids f rom ailanthus vilmorintana [J]. Phytochemistry,1998,48 (3):5651.
[76]Chan KL, Choo CHY, Abdullah NR, et al. Antiplasmodialst udies of Eurycoma longifolia Jack using the lactatedehydrogenase assay of Plasmodium falciparum [J].J Ethnopharmacol,2004,92 (2～3):2231.
[77]Franqoiqa G, Diakanamwa C, Timp xman G, et al. Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and the instructure-activity relationships [J]. Int J Parasitol,1998,28 (4):6351.
[78]Okunade A L, Bikoff R E, Casper S J, et al. Antiplasmodial activity of extracts and quassinoids isolated from seedlings of Ailanthus altissima (Simaroubaceae) [J]. Phytother Res,2003,17 (6):6751.
[79]Ishibashi M, Furuno T, Tsuyuki T, et al. Structures of shinjulactones D and E, new bitter principles of Ailanthus altissima Swingle. Chem Pharm Bull,1983,31: 2179-2182.
[80]Ishibashi M, Yoshimura S, Tsuyuki T, et al. Shinjulactone F, a new bitter principle with 5βH-picrasane skeleton from Ailanthus altissima Swingle. Chem Lett,1984.555-556.
[81]Ishibashi M, Yoshimura S, Tsuyuki T, et al. Structure determination of bitter principles of Ailanthus altissima. Structures of shinjulactones F, I, J and K. Bull Chem Soc Jpn,1984,57:2885-2892.
[82]Ishibashi M, Yoshimura S, Tsuyuki T, et al. Shinjulactones G and H, new bitter principles of Ailanthus altissima Swingle. Bull Chem Soc Jpn,1984,57: 2013-2014.
[83]Ishibashi M, Tsuyuki T, Takahashi T. Structure determination of a new bitter principle, shinjulactone L, from Ailanthus altissima. Bull Chem Soc Jpn,1985,58: 2723-2724.
[2]谭庆伟,吴祖建,欧阳明安.臭椿化学成分及生物活性研究进展[J].天然产物研究与开发,2008,20：748-755.
[3]林隆泽,张金生,陈仲良等.鸦胆子化学成分的研究(Ⅰ.鸦胆子酮酸等五个苦木素的分离和鉴定)[J].化学学报,1982,40(1),73-78.
[4]顶晨旭,索有瑞.中药鸦胆子化学成分及药理学研究进展,2006,28(1)：117-120.
[5]王玫馨,张敏生,朱元龙等.草药牛筋果化学成分的研究.药学学报,1984,19(10)：760-763.
[6]王玫馨,张敏生,朱元龙.草药牛筋果化学成分的研究.药学学报,1983,18(2)：113-118.
[7]卫新成,金祥林,顾孝诚等.牛筋果有效成分牛晶Ⅰ的分子和晶体结构.北京大学学报(自然科学版)1986,4,15-20.
[8]卫新成,潘佐华,顾孝诚.草药牛筋果化学成分的研究Ⅳ牛晶Ⅴ的分子晶体结构.结构化学.1985,4(4)：281-287.
[9]中国科学院中国植物志编辑委员会.中国植物志.第四十三卷.第三分册.北京：科学出版社,1997.15
[10]马汉铭,杜平华.数理医药学杂志.2002,15(2)：158.
[11]谷华,王梅,王志阳.中医研究,2001,14(5)：55-56.
[12]吴元德等：苯并芘自由基中间产物酶代谢研究.第四届全国生物物理学学术会议论之摘要汇编(上),P72,1983.
[13]Ju J H(鞠建华),Yang J S(杨峻山),Liu D(刘东).Study on thechemical components of Beesia calthaifolia Ⅱ[J]. Chin Pharm J(中国药学杂志),2000,35 (3):157-160. (in Chinese).
[14]Zhang W J(张雯洁),Liu Y Q(刘玉清),Li X C(李兴从),et al. Chemical constituents of "Ecological Tea" from Yunnan [J]. Acta Bot Yunnan(云南植物研 究),1995,17(5)：204-208.(in Chinese).
[15]闫利华,徐丽珍,邹忠梅.小木通茎的化学成分研究(Ⅰ).中草药,2007,38(3)：340-342.
[16]Dai H F(戴好富),Zhou J(周俊),Peng Z G(彭再刚),et al.Studieson the chemical constituents of Scisandra chinensis [J]. Nat ProdRes Devlop(天然产物研究与开发),2001,13(1)：24-26.(in Chinese)
[17]杨虹,王峥涛,胡之璧,等.半夏的化学成分研究[J].中国药学杂志,2007,42(2)：101.
[18]戴好富,梅文莉,曾艳波,等.红树林植物木果楝细胞毒活性和化学成分研究.天然产物研究与开发,2007,19(1)：74-76.
[19]TRAN VAN SUNG, NGUYEN MiNH PHUONG, CHRISTINE KANMPERDICK, et al. (1995). PERFORATINOLONE, A LIMONOID FROM HARRISONIA PERFORATA. Phytochemistey.38(1), pp.213-215.
[20]TOMOKO TANAKA, KAZUO KOIKE, KATSUYOSHI MITSUNAGA, et al. (1995). CHROMONES FROM HARRISONIA PERFORATA. Phytochemistry, 40(6), pp.1787-1790.
[21]Tripetch K, Ryoji K, Phannipha C, et al. Phytochemistry,2001,56 (2): 383～386.
[22]Simon G, Lyn C, Clyde D, et al. Phytochemistry,1997,44 (6):1109～1114.
[23]Sheng Yin, Xin Chen, Zu-Shang Su, et al. Harrisotones A-E, five novel prenylated polyketides with a rare spirocyclic skeleton from Harrisonia perforate. Tetrahedron 65 (2009) 117-1152.
[24]Qui Khuong-Huu, Angele Chiaroni, Claude Riche, et al. New Rearranged Limonoids from Harrisonia perforate. J. Nat. Prod.2000,63,1015-1018.
[25]Petelot, A. Les plantes medicinales du Cambodge, Du Laos et du Viet-Nam, Archives des Recherches Agronomiques au Cambodge, au Laos et an Viet-Nam 1952; Vol.Ⅰ. p 169.
[26]Penso, G. Inventaire des Plants medicinales employees dans les differents pays, O. M. S. DPM/80.3.
[27]Tuntiwachwuttiku Pittaya, Phansa Photchana, Pootaeng-On Yupa, et al. Chromones from the braches of Harrisonia perforata. Chemical & Pharmaceutical Bulletin,2006,54 (1):44～47.
[28]Byrne, L.T., Tri, M.V., Phuong, N. M., Sargent, M.V., Skelton, B.W. and White, A.H. (1991) Aust.J.Chem.44,165.
[29]Chanpagne, D. E., Koul,O., Isman, M.B., Scudder, G. G. E. and TOWERS, G. H. N.(1992) Phytochemistry 31,377.
[30]Mitsunaga, K., Koike, K., Ishii, K. and Ohmoto, T. (1994) Phytochemistey 35,451.
[31]Qui Khuong-Huu, Angele Chiaroni, Claude Riche, et al. New Rearranged Limonoids from Harrisonia perforate.Ⅲ. J. Nat. Prod.2001,64,634-637.
[32]Chiaroni, A.; Riche, C.; Khuong-Huu, Q.; Nguyen-Ngoc, H.; Nguyen-Viet, K.; Khuong-Huu, F. Acta Crystallogr.2000, C56,711-713.
[33]Wei, X.; Pan, Z.; Gu, X.; Wang, M.; Zhu, Y. Jiegou Huaxue 1985, 4,281-287.(5), Byrne, L. T.; Van Tri, M.; Nguyen-Minh, P.; Sargent, M. V.; Skelton, B. W.; White, A. H. Austr. J. Chem.1991,44,165-169.
[34]TranVan, S.; Nguyen-Minh, P.; Kamperdick, C.; Adam, G. Phytochemistry 1995,38,213-215.
[35]Kamiuchi, K.; Mitsunaga, K.; Koike, K.; Ouyang, Y.; Ohmoto, T.; Nikaido, T. Heterocycles 1996,43,653-664.
[36]Angele Chiaroni, Claude Riche, Qui Khuong-Huu, et al. New Limonoids from Harrisonia Perforata (Blanco) Merr. Acta Cryst. (2000). C56,711-713.
[37]Khuong-Huu Q.; Chiaroni, A.; Riche, C.; Nguyen-Ngoc, H.; Nguyen-Viet, K.; Khuong-Huu, F. J. Nat. Prod.2000,63,1015-1018.
[38]Perry Lily May. Medicinal Plants of East and Southeast Asia:Attributed Properties and Uses. America, Massachusetts, Cambridge:Massachusetts Institute of Technology Press,1980.389.
[39]Bremner J B. New alkaloids with potential biological activity. In: Proceedings of the 7th Asian Symposium on Medicinal Plants, Spices and Other Natural Products. Philippines, Manila:ASOMPS,1992.75.
[40]Grieco P A, Haddad J, Pineiro-Nunez M M, et al. Phytochemistry,1999, (4): 575-578.
[41]Carmen G, Azucena GC, et al. Industrial Crops and Products,1999,10 (1): 35-40.
[42]F.B. Magassouba, A. Diallo, M. Kouyate, et al. Ethnobotanical survey and antibacterial activity of some plants used in Guinean traditional medicine. Journal of Ethnopharmacology 114 (2007) 44-53.
[43]Aun Chea, Marie-Caroline Jonville, Sok-Siya Bun et al.2007. In vitro Antimicrobial Activity of Plants used in Cambodian Teaditional Medicine. The American Journal of Chinese Medicine, Vol.35, No.5,867-873.
[44]Werner Fabry, Paul O. Okemo, Rainer Ansorg. Antibacterial activity of East African medicinal plants. Journal of Ethnopharmacology 60 (1998) 79-84.
[45]Jittra Limsong, E. Benjavongkulchai, Jintakorn Kuvatanasuchati. Inhibitory effect of some herbal extracts on adherence of Streptococcus mutans. Journal of Ethnopharmacology 92 (2004) 281-289.
[46]Julie Nguyen-Pouplin, Hop Tran, Hung Tran, et al.Antimalarial and cytotoxic activities of ethnopharmacologically selected medicinal plants from South Vietnam. Journal of Ethnopharmacology 109 (2007) 417-427.
[47]Tanaka, T., Koike, K., Mitsunaga, K., Narita, K., Takano, S., Kamioka, A., Sase, E., Ouyang, Y., Ohmoto, T.,1995. Chromones from Harrisonia perforata. Phytochemistry 40,1787-1790.
[48]Kamiuchi, K., Mitsunaga, K., Koike, K., Ouyang, Y., Ohmoto, T., Nikaido, T.,1996. Quassinoids and limonoids from Harrisonia perforata. Heterocycles 43, 653-664.
[49]Murakami, N., Sugimoto, M., Kawanishi, M., Tamura, S., Kim, H.S., Begum, K., Wataya, Y., Kobayashi, M.,2003. New semisynthetic quassinoids with in vivo antimalarial activity. Journal of Medicinal Chemistry 46,638-641.
[50]Krief, S., Martin, M.T., Grellier, P., Kasenene, J., Sevenet, T.,2004. Novel antimalarial compounds isolated in a survey of self-medicative behavior of wild chimpanzees in Uganda.Antimicrobial Agents and Chemotherapy 48,3196-3199.
[51]Ahmed El Tahir, Gwiria M.H. Satti, Sami A. Khalid. Antiplasmodial activity of selected Sudanese medicinal plants with emphasis on Maytenus senegalensis (Lam.) Exell. Journal of Ethnopharmacology 64 (1999) 227-233.
[52]AHMED HASSANALI, MICHAEL D. BENTLEY, ALEXANDRA M. Z. SLA WIN et al. PEDONIN, A SPIRO TETRANORTRITERPENOID INSECT ANTIFEEDANT FROM HARRISONIA ABYSSINICA. Phyrochemimy, Vol.26. No.2, pp.573-575.1987.
[53]B.K. MEHTA, KM. SAVITA SHARMA and AVINASFH DUBEY. 4-ETHYLGALLIC ACID FROM TWO MIMOSA SPECIES. Phgtochemistry. Vol.27, No.9, pp.3004-3005.1988.
[54]Jiwajinda S, Santisopasri V, Murakami A, et al. Jethnopharmacology,2002, 82(1):55-58.
[55]Morre D J, Grieco P A, Morre D M, et al. Life Sci,1998,63 (7):595-604.
[56]Tamura S, Fukamiya N, Okano M, et al. Three new quassinoids, ailantinol E, F, and G, from Ailanthus altissim a. ChemPharm Bull,2003,51:385-389.
[57]Seida A A, Kinghorn A D, Cordell G A, et al. Potential anticancer agents. Isolation of a new simaroubolide,6α-tigloy-loxychaparrinone, from Ailanthus integrifolia ssp. Calycina (Simaroubaceae). Lloydia,1978,41:584-587.
[58]O'NeillM, Bray DH, Boardman P, et al. Plants as sources of antimalarial drugs:In vitro antimalarial activities of some quassinoids. Antim icrob Agents Chem other,1986,30:101-104.
[59]Ohmoto T, Sung YI. Antimycotic substances in the crude drugs Ⅱ. Shoyakugaku Zasshi,1982,36:307-314
[60]Mergen F. Atoxic principle in the leaves of Ailanthus. Bot Gaz,1959,121: 32-36.
[61]Lin L J, Peiser G, YingB P, et al. Identification of plant growthinhibitory p rincip les in Ailanthus altissima and Castela tortuosa. J Agric Food Chem,1995, 43:1708-1711.
[62]De Feo V, De Martino L, Santoro A, et al. Antiproliferative effects of tree of heaven(Ailanthus altissima Swingle). Phytother Res,2005,3:226-230.
[63]Tsao R, Romanchuk F E, Peterson C J, et al. Plant growth regulatory effect and insecticidal activity of the extracts of the tree of Heaven(Ailanthus altissima L.). BMC Ecology,2002,2:1.
[64]De Feo V, De Martino L, Quaranta E, et al. Isolation of phytotoxic compounds from tree-of-heaven (Ailanthus altissim aswingle). J Agric Food Chem,2003,51:1177-1180.
[65]Casinovi C G, Ceccherelli P, Fardella G, et al. Isolation and structure of a quassinoid from Ailanthus glandulosa. Phytochemistry,1983,22:2871-2873.
[66]Xu S H(许申鸿),Hang H(杭湖).A simple method for the screening of free radical scavenger [J]. Chin Trad Herb Drugs(中草药),2000,31 (2):96-97. (in Chinese)
[67]Xu S H(许申鸿),Hang H(杭湖).Preliminarily study on DPPH assay by spectrophotometry and its application [J]. Plant Physiol Commun(植物生理学通讯),1999,35(6)：472-477.(in Chinese)
[68]Chen C J(陈丛瑾),Huang K Y(黄克瀛),Sun C L(孙崇鲁).Study on DPPH free radicals scavenging activity of Solanum lyratum Thumb fruit extractives [J]. Food Res Develop(食品研究与开发),2006,27 (10):45-48. (in Chinese)
[69]Ang H H, Hitotsuyanagi Y, Fukaya H, et al. Tetrahedron Letters,2000,41(7): 6849～6853.
[70]Ang H H, Hitotsuyanagi Y, Fukaya H, et al. Phytochemistry,2002,59 (8): 833～837.
[71]Zahid L, Lyn C, Hartley TG, et al. Biochemical systematics and Ecology, 2000,28(2):183～184.
[72]Fernando M, Luko H, Gerardo A M, et al. Crop Protection,2000,19(3): 301～305.
[73]Tamuraa S, Fukamiyaa N, Okano M, et al. Cancer chemopreventive effect of quassinoid derivatives. Introduction of side chain to shinjulactone C for enhancement of inhibitory effect on Epstein-Barr virus activation [J]. Cancer Lett, 2002,185(1):471.
[74]Mata-Greenwood E, Cuendet M, Sher D, et al. Brusatol-mediated induction of leukemic cell differentiation and G1 arrest asscciated wit h down-regulation of cmyc [J]. Leukemia,2002,16 (11):2275.
[75]Takeya K, Kobata H, Ozeki A, et al. Quassinoids f rom ailanthus vilmorintana [J]. Phytochemistry,1998,48 (3):5651.
[76]Chan KL, Choo CHY, Abdullah NR, et al. Antiplasmodialst udies of Eurycoma longifolia Jack using the lactatedehydrogenase assay of Plasmodium falciparum [J].J Ethnopharmacol,2004,92 (2～3):2231.
[77]Franqoiqa G, Diakanamwa C, Timp xman G, et al. Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and the instructure-activity relationships [J]. Int J Parasitol,1998,28 (4):6351.
[78]Okunade A L, Bikoff R E, Casper S J, et al. Antiplasmodial activity of extracts and quassinoids isolated from seedlings of Ailanthus altissima (Simaroubaceae) [J]. Phytother Res,2003,17 (6):6751.
[79]Ishibashi M, Furuno T, Tsuyuki T, et al. Structures of shinjulactones D and E, new bitter principles of Ailanthus altissima Swingle. Chem Pharm Bull,1983,31: 2179-2182.
[80]Ishibashi M, Yoshimura S, Tsuyuki T, et al. Shinjulactone F, a new bitter principle with 5βH-picrasane skeleton from Ailanthus altissima Swingle. Chem Lett,1984.555-556.
[81]Ishibashi M, Yoshimura S, Tsuyuki T, et al. Structure determination of bitter principles of Ailanthus altissima. Structures of shinjulactones F, I, J and K. Bull Chem Soc Jpn,1984,57:2885-2892.
[82]Ishibashi M, Yoshimura S, Tsuyuki T, et al. Shinjulactones G and H, new bitter principles of Ailanthus altissima Swingle. Bull Chem Soc Jpn,1984,57: 2013-2014.
[83]Ishibashi M, Tsuyuki T, Takahashi T. Structure determination of a new bitter principle, shinjulactone L, from Ailanthus altissima. Bull Chem Soc Jpn,1985,58: 2723-2724.