石地钱和溪边青藓化学成分研究
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摘要
苔藓植物在分类学上介于藻类植物和蕨类植物之间,全世界约有20000余种,可分为藓纲、苔纲和角苔纲三类。苔藓植物具有重要的药用价值,在民间广泛用于治疗外伤、烧伤、感染、结核、肺炎和神经衰弱等症,近年来从苔藓植物中分离获得了大量结构新颖而且活性显著的萜类化合物和芳香族化合物,其中许多可作为新药研究的良好先导化合物,对苔藓植物活性成分的研究表明苔藓植物是生物活性天然产物的重要来源。
近年来随着HIV蔓延、肿瘤的增加、耐药菌的出现及人们对药物毒副作用的顾虑,寻求新的高效低毒药物迫在眉睫,苔藓中所含成分在以上领域具有潜在药物开发价值。此外,传统农业对环境和资源的负面影响日益受到关注,世界人民对生态农业的呼声越来越高,苔藓植物在这方面也具有重要的应用价值。
本文对采自中国湖南长沙岳麓山地区的石地钱Reboulia hemisphaerica(linn.)raddi进行系统的化学成分研究,从该植物中分离获得了24个化合物,鉴定了其中的22个,这些化合物包括10个双联苄类化合物:地钱素C(marchantin C,Ⅰ)、新地钱素A(neomarchantin A,Ⅱ)、片叶苔素B(riccardin B,Ⅲ)、片叶苔素C(riccardin C,Ⅳ)、地钱素A(marchantin A,Ⅴ)、地钱素J(marchantin J,Ⅵ)、Pakyonol(Pakyonol,Ⅶ)、核木子素E(perrottetin E,Ⅷ)、异片叶苔素C(isoriccardin C,Ⅸ)、异地钱素C(isomarchantin C,Ⅹ);1个联苄类化合物半月苔素(lunularin,Ⅺ);2个黄酮化合物:5-羟基-4′,6,7-三甲氧基黄酮(apigenin-6,7,4′-trimethyl ether,Ⅻ)和芹菜素(apigenin,ⅩⅢ);2个菲类化合物:2-羟基-3,7-二甲氧基菲(2-hydroxy-3,7-dimethoxy phenanthrene,ⅩⅣ)和2-羟基-3,5-二甲氧基菲(2-hydroxy-3,5-dimethoxy phenanthrene,ⅩⅤ);1个单苯环衍生物:烯丙氢醌(allylhydroquinone,ⅩⅥ);2个三萜:α-泽渥萜(α-zeorin,ⅩⅦ)、6α,11α,22-三羟基何伯烷(6α,11α,22-trihydroxy hopane,ⅩⅧ);1个倍半萜:rulepidol(rulepidol,ⅩⅨ);2个甾体化合物:豆甾醇二十烷酸酯(stigmosterolarachidate,ⅩⅩ)和β-谷甾醇(β-sitosterol,ⅩⅩⅠ)及糖甘露醇(mannitol,ⅩⅩⅡ)。化合物结构采用NMR,MS和IR等波谱法及同己知化合物进行TLC对照或混和测定熔点鉴定。22个化合物中,Ⅵ、Ⅶ、Ⅷ、Ⅺ、Ⅻ、ⅩⅢ、ⅩⅣ、ⅩⅤ、ⅩⅥ、ⅩⅨ、ⅩⅩ为首次从该种植物分离获得。
此外,本文还对采自浙江临安西天目山的溪边青藓Brachythecium rivulareB.S.G进行了化学成分的系统分离试验研究,采用各种色谱分离法从溪边青藓中分离获得了7个化合物:苔色酸乙酯(ethyl orsellinate,ⅰ)、对羟基苯甲醛(4-hy-droxybenzaldehyde,ⅱ)、黑麦草内酯(loliolide,ⅲ)、3′,3′′′-binaringenin(3′,3′′′-binaringenin,ⅳ)、乌索酸(ursolic acid,ⅴ)、β-谷甾醇(β-sitostero,ⅵ)、里白烯(diploptene,ⅶ)。化合物结构采用NMR,MS和IR等波谱法及同己知化合物进行TLC对照或混和测定熔点鉴定。7个化合物均为首次从该种植物分离获得。
The bryophytes are taxonomically placed between the algae and the pteridophytes and more than 20000 species are known in the world.Bryophytes have important medicinal value.For thousands of years,the bryophytes have been used in folk remedies to cure various kinds of diseases such as cuts,bums,bacteriosis, tuberculosis,pneumonia,neurasthenia etc.Many terpeniods and aromatic compounds with novel skeletons or significant bioactivities have been obtained from mosses and liverworts,some of which are nice lead compounds in new drug research.Many studies indicate that the bryophyte components constitute a rich source of structually new and biologically active compounds.
In recent years,with the spread of HIV,an increase in tumor,the emergence of drug-resistant and people's concerns about drug toxic or side effects,low toxicity and efficient development of new drugs is imminent.Chemical constituents from bryophytes possess the potential value of drug development in the above fields.In addition,traditional agriculture on the environment and resources has become an increasing concern about the negative impact.People's increasing demands for ecological agriculture are more strongly.The bryophytes have the important application value in this aspect.
In this paper,a systematically phytochemical investigation of the chemical constituents of Reboulia hemisphaerica(linn.) raddi collected from Mount Yue-lu, Hunan Province,PR China was carried out,and led to yield 24 compounds,22 of which were identified,including ten bis(bibenzyl)s:marchantin C(Ⅰ),neomarchantin A(Ⅱ),riccardin B(Ⅲ),riccardin C(Ⅳ),marchantin A(Ⅴ),marchantin J(Ⅵ), pakyonol(Ⅶ),perrottetin E(Ⅷ),isoriccardin C(Ⅸ) and isomarchantin C(Ⅹ);one bibenzyl:lunulafin(Ⅺ);two flavones:apigenin-6,7,4'-trimethylether(Ⅻ) and apigenin (ⅩⅢ);two phenanthrenes:2-hydroxy-3,7-dimethoxyphenanthrene(ⅩⅣ) and 2-hydroxyl-3,5-dimethoxy phenanthrene(ⅩⅤ);one benzene derivative:allylhydroquinone (ⅩⅥ);two triterpenoids:α-zeorin(ⅩⅦ),6α,11α,22-trihydroxyhopane(ⅩⅧ); one sesquiterpenoid:rulepidol(ⅩⅨ);two steroids:stigmosterol arachidate(ⅩⅩ),β-sitosterol(ⅩⅪ) and mannitol(ⅩⅫ).The structures were elucidated on the basis of 1D and 2D-NMR,MS and IR spectroscopy.Among these compounds, compoundsⅥ,Ⅶ,Ⅷ,Ⅺ,Ⅻ,ⅩⅢ,ⅩⅣ,ⅩⅤ,ⅩⅥ,ⅩⅨ,andⅩⅩare first reported in R.hemisphaerica.
Furthermore,we also investigated chemical constituents of Brachythecium rivulare B.S.G collected from West Tianmushan,Zhejiang Province,PR China.Six compounds were obtained by repeated chromatography and their structures were established by NMR together with IR and MS spectroscopy as ethyl orsellinate(ⅰ), 4-hydroxybenzaldehyde(ⅱ),loliolide(ⅲ),3′,3′″-binaringenin(ⅳ),ursolic acid(ⅴ),β-sitosterol(ⅵ),diploptene(ⅶ).Seven compounds were all isolated from this species for the first time.
近年来随着HIV蔓延、肿瘤的增加、耐药菌的出现及人们对药物毒副作用的顾虑,寻求新的高效低毒药物迫在眉睫,苔藓中所含成分在以上领域具有潜在药物开发价值。此外,传统农业对环境和资源的负面影响日益受到关注,世界人民对生态农业的呼声越来越高,苔藓植物在这方面也具有重要的应用价值。
本文对采自中国湖南长沙岳麓山地区的石地钱Reboulia hemisphaerica(linn.)raddi进行系统的化学成分研究,从该植物中分离获得了24个化合物,鉴定了其中的22个,这些化合物包括10个双联苄类化合物:地钱素C(marchantin C,Ⅰ)、新地钱素A(neomarchantin A,Ⅱ)、片叶苔素B(riccardin B,Ⅲ)、片叶苔素C(riccardin C,Ⅳ)、地钱素A(marchantin A,Ⅴ)、地钱素J(marchantin J,Ⅵ)、Pakyonol(Pakyonol,Ⅶ)、核木子素E(perrottetin E,Ⅷ)、异片叶苔素C(isoriccardin C,Ⅸ)、异地钱素C(isomarchantin C,Ⅹ);1个联苄类化合物半月苔素(lunularin,Ⅺ);2个黄酮化合物:5-羟基-4′,6,7-三甲氧基黄酮(apigenin-6,7,4′-trimethyl ether,Ⅻ)和芹菜素(apigenin,ⅩⅢ);2个菲类化合物:2-羟基-3,7-二甲氧基菲(2-hydroxy-3,7-dimethoxy phenanthrene,ⅩⅣ)和2-羟基-3,5-二甲氧基菲(2-hydroxy-3,5-dimethoxy phenanthrene,ⅩⅤ);1个单苯环衍生物:烯丙氢醌(allylhydroquinone,ⅩⅥ);2个三萜:α-泽渥萜(α-zeorin,ⅩⅦ)、6α,11α,22-三羟基何伯烷(6α,11α,22-trihydroxy hopane,ⅩⅧ);1个倍半萜:rulepidol(rulepidol,ⅩⅨ);2个甾体化合物:豆甾醇二十烷酸酯(stigmosterolarachidate,ⅩⅩ)和β-谷甾醇(β-sitosterol,ⅩⅩⅠ)及糖甘露醇(mannitol,ⅩⅩⅡ)。化合物结构采用NMR,MS和IR等波谱法及同己知化合物进行TLC对照或混和测定熔点鉴定。22个化合物中,Ⅵ、Ⅶ、Ⅷ、Ⅺ、Ⅻ、ⅩⅢ、ⅩⅣ、ⅩⅤ、ⅩⅥ、ⅩⅨ、ⅩⅩ为首次从该种植物分离获得。
此外,本文还对采自浙江临安西天目山的溪边青藓Brachythecium rivulareB.S.G进行了化学成分的系统分离试验研究,采用各种色谱分离法从溪边青藓中分离获得了7个化合物:苔色酸乙酯(ethyl orsellinate,ⅰ)、对羟基苯甲醛(4-hy-droxybenzaldehyde,ⅱ)、黑麦草内酯(loliolide,ⅲ)、3′,3′′′-binaringenin(3′,3′′′-binaringenin,ⅳ)、乌索酸(ursolic acid,ⅴ)、β-谷甾醇(β-sitostero,ⅵ)、里白烯(diploptene,ⅶ)。化合物结构采用NMR,MS和IR等波谱法及同己知化合物进行TLC对照或混和测定熔点鉴定。7个化合物均为首次从该种植物分离获得。
The bryophytes are taxonomically placed between the algae and the pteridophytes and more than 20000 species are known in the world.Bryophytes have important medicinal value.For thousands of years,the bryophytes have been used in folk remedies to cure various kinds of diseases such as cuts,bums,bacteriosis, tuberculosis,pneumonia,neurasthenia etc.Many terpeniods and aromatic compounds with novel skeletons or significant bioactivities have been obtained from mosses and liverworts,some of which are nice lead compounds in new drug research.Many studies indicate that the bryophyte components constitute a rich source of structually new and biologically active compounds.
In recent years,with the spread of HIV,an increase in tumor,the emergence of drug-resistant and people's concerns about drug toxic or side effects,low toxicity and efficient development of new drugs is imminent.Chemical constituents from bryophytes possess the potential value of drug development in the above fields.In addition,traditional agriculture on the environment and resources has become an increasing concern about the negative impact.People's increasing demands for ecological agriculture are more strongly.The bryophytes have the important application value in this aspect.
In this paper,a systematically phytochemical investigation of the chemical constituents of Reboulia hemisphaerica(linn.) raddi collected from Mount Yue-lu, Hunan Province,PR China was carried out,and led to yield 24 compounds,22 of which were identified,including ten bis(bibenzyl)s:marchantin C(Ⅰ),neomarchantin A(Ⅱ),riccardin B(Ⅲ),riccardin C(Ⅳ),marchantin A(Ⅴ),marchantin J(Ⅵ), pakyonol(Ⅶ),perrottetin E(Ⅷ),isoriccardin C(Ⅸ) and isomarchantin C(Ⅹ);one bibenzyl:lunulafin(Ⅺ);two flavones:apigenin-6,7,4'-trimethylether(Ⅻ) and apigenin (ⅩⅢ);two phenanthrenes:2-hydroxy-3,7-dimethoxyphenanthrene(ⅩⅣ) and 2-hydroxyl-3,5-dimethoxy phenanthrene(ⅩⅤ);one benzene derivative:allylhydroquinone (ⅩⅥ);two triterpenoids:α-zeorin(ⅩⅦ),6α,11α,22-trihydroxyhopane(ⅩⅧ); one sesquiterpenoid:rulepidol(ⅩⅨ);two steroids:stigmosterol arachidate(ⅩⅩ),β-sitosterol(ⅩⅪ) and mannitol(ⅩⅫ).The structures were elucidated on the basis of 1D and 2D-NMR,MS and IR spectroscopy.Among these compounds, compoundsⅥ,Ⅶ,Ⅷ,Ⅺ,Ⅻ,ⅩⅢ,ⅩⅣ,ⅩⅤ,ⅩⅥ,ⅩⅨ,andⅩⅩare first reported in R.hemisphaerica.
Furthermore,we also investigated chemical constituents of Brachythecium rivulare B.S.G collected from West Tianmushan,Zhejiang Province,PR China.Six compounds were obtained by repeated chromatography and their structures were established by NMR together with IR and MS spectroscopy as ethyl orsellinate(ⅰ), 4-hydroxybenzaldehyde(ⅱ),loliolide(ⅲ),3′,3′″-binaringenin(ⅳ),ursolic acid(ⅴ),β-sitosterol(ⅵ),diploptene(ⅶ).Seven compounds were all isolated from this species for the first time.
引文
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56 Morais R.In Vitro-Kultur und Sekund(a|¨)rstoffproduktion des Lebermooses Reboulia hemisphaerica(L.)Raddi.Ph.D.Thesis,Universit(a|¨)t des Saarlandes,1990
57 Hashimoto T,Asakawa Y,Nakashima K,et al.Chemical Constituents of 25Liverworts.J Hattori Bot Lab.1993,74:121
58 Beyer J.Terpene aus freilebenden Lebermoosen und deren Sterilkulturen.Ph.D Thesis,Universit(a|¨)t Heidelberg.1988
59 AsakawaY,Matsuda R.Riccardin C,a novel cyclic bibenzyl derivative from Reboulia hemisphaerica.Phytochemistry.1982,21(8):2143-2144
60 Morais RM,Harrison LJ,Becker H.A.gymnomitrane-type sesquiterpenoid from in vitro cultures of Reboulia hemisphaerica.Phytochemistry.1991,30(3):1013-1014
61 Wei HC;Ma SJ;Wu CL.Sesquiterpenoids and cyclic bisbibenzyls from the liverwort Reboulia hemisphaerica.Phytochemistry.1995,39(1):91-97
62 Toyota M,Konoshima M;Asakawa Y.Terpenoid constituents of the liverwort Reboulia hemisphaerica.Phytochemistry.1999,52(1):105-112
63 Warmers U,K(o|¨)nig WA..Gymnomitrane-type sesquiterpenes of the liverworts Gymnomitrion obtusum and Reboulia hemisphaerica.Phytochemistry.1999,52(8):1501-1505
64 Furusawa M,Hashimoto T,Noma Y,et al.Isolation and structures of new cyclomyltaylane and ent-chamigrane-type sesquiterpenoids from the liverwort Reboulia hemishaerica and their biotransformation by the fungus Aspergillus niger.Chem Pharm Bull.2006,54(7):996-1003
65 AsakawaY,Toyota M,Tori M,et al.Chemical structures of macrocyclic bis(bi benzyls) isolated from liverworts(Hepaticae).Spectroscopy.2000,14:149-175
66 Tori M,Toyota M,Harrison LJ,et al.Total assignment of ~1H and ~(13)C NMR spectra of Marchantins isolated from liverworts and its application to structure determination of two new macrocyclic bis(bibenzyls) from Plagiochasma intermedium and Riccardia multifida.Tetrahedron Lett.1985,26:4735-4738
67 Asakawa Y,Tori M,Masuya T.Ent-sesquiterpenoids and cyclic bis(bibenzyls) from the German liverwort Marchantia polymorpha.Phytochemistry.1990,29(5):1577-1584
68 王凤强,娄红祥.无纹紫背苔化学成分的研究.药学学报.2000,35(8):587-591
69 Toyota M,Tori M,Takikawa K,et al.Perrottetins E,F and G from Radula perrottetii(Liverwort)-isolation,structure determination and synthesis of perrottetin E.Tetrahedron Lett.1985,26:6097-6100
70 Asakawa Y,Tod M,Krishnamurty H.G.Cyclc bis(bibenzyls) and related compounds from the liverworts Marchantia polymorpha and Marchantia Palmata.Phytochemistry.1987,26(6):1811-1816
71.Asakawa Y,Cannolly EO.Terpenoids and bibenzyls from some NewZlealand liverworts.Phytochemistry.1982,21:2663-2668
72 Kraut L,Klein R,Mues R.Z.Naturforsch.C.1992,47:794
73 李晓强,武静莲,曹斐华,等.白花泡桐叶化学成分的研究.2008,31(6):850-852
74 夏萍芳,李仲辉.香港地钱抗菌化学成分研究.天然产物研究与开发.2001,13(5):15-17
75 Anton H,Kraut L,Mues R.Phenanthrenes and bibenzyls from a Plagiochila species.Phytochemistry.1997,46(6):1067-1075
76 Hegedus LS,Evans BR,Korte DE,E.L.et al.Reactions of.pi.-allylnickel bromide complexes with quinones.Synthesis of isoprenoid quinines.J Am Chem Soc.1976,98(13),3901-3909
77 Gabriele MK,Anthony DW,~1H and ~(13)C-NMR and biological activity investigations of four lichen-derived compounds.Phytochem Anal.1999,10(5):279-284
78 Hashimoto T,Asakawa Y,Nakashima K.Chemical Constituents of 25Liverworts.J Hattori Bot Lab.1993,74,121
79 谭建文,董泽军,刘吉开.鳞盖红菇中一个新的倍半萜类化合物.植物学报.2001,43(3):329-330
80 李光耀,娄红祥,王浩.盔瓣耳叶苔化学成分研究.中草药.2001,32(8):678-681
81.Catalano S,Marsili A,Morelli I,et al.Tfiterpenoids and fatty acids from some mosses obtusifoliol from Racomitrium lanuginosum.Phytochemistry.1976,15(7):1178-1179
82 刘岱琳,庞发根,张家欣,等.密花石豆兰的化学成分研究.中国药物化学杂志.2005,15(2):103-108
83 张海娟.五种植物的化学成分及其生物活性研究.山东大学博士学位论文,2007
84 Kimura J,Maki N.New Loliolide Derivatives from the Brown Alga Undaria pinnatifida.J Nat Prod.2002,65,57-58
85 Seeger T,Geiger H,Zinsmeister HD,et al.Biflavonoids from the moss Homalothecium lutescens.Phytochemistry.1993,34(1):295-296
86 Fan WQ,Xiong MX,Ma Z,et al.Chemical Constituents of Alte rnanthera philoxeroides.Chin J Nat Med.2008,6(2):112-115
87 王小宁,娄红祥.扁枝藓化学成分研究.中国药学杂志.2005,40(15):1131-1133
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54 Chavan SP,Kharul RK,Kale RR.,et al.An efficient synthesis of(±)-β-herebertenol by a 1,3-cyclopentadione annelation strategy.Tetrahedron.2003,59:2737-2741
55 Srikrishna A,Satyanarayana G.Total synthesis of(±)-1,13-herbertenediol,(±)-α-herbertenol and(±)-β-herbertenol.Tetrahedron Lett.2003,44:1027-1030
56 Morais R.In Vitro-Kultur und Sekund(a|¨)rstoffproduktion des Lebermooses Reboulia hemisphaerica(L.)Raddi.Ph.D.Thesis,Universit(a|¨)t des Saarlandes,1990
57 Hashimoto T,Asakawa Y,Nakashima K,et al.Chemical Constituents of 25Liverworts.J Hattori Bot Lab.1993,74:121
58 Beyer J.Terpene aus freilebenden Lebermoosen und deren Sterilkulturen.Ph.D Thesis,Universit(a|¨)t Heidelberg.1988
59 AsakawaY,Matsuda R.Riccardin C,a novel cyclic bibenzyl derivative from Reboulia hemisphaerica.Phytochemistry.1982,21(8):2143-2144
60 Morais RM,Harrison LJ,Becker H.A.gymnomitrane-type sesquiterpenoid from in vitro cultures of Reboulia hemisphaerica.Phytochemistry.1991,30(3):1013-1014
61 Wei HC;Ma SJ;Wu CL.Sesquiterpenoids and cyclic bisbibenzyls from the liverwort Reboulia hemisphaerica.Phytochemistry.1995,39(1):91-97
62 Toyota M,Konoshima M;Asakawa Y.Terpenoid constituents of the liverwort Reboulia hemisphaerica.Phytochemistry.1999,52(1):105-112
63 Warmers U,K(o|¨)nig WA..Gymnomitrane-type sesquiterpenes of the liverworts Gymnomitrion obtusum and Reboulia hemisphaerica.Phytochemistry.1999,52(8):1501-1505
64 Furusawa M,Hashimoto T,Noma Y,et al.Isolation and structures of new cyclomyltaylane and ent-chamigrane-type sesquiterpenoids from the liverwort Reboulia hemishaerica and their biotransformation by the fungus Aspergillus niger.Chem Pharm Bull.2006,54(7):996-1003
65 AsakawaY,Toyota M,Tori M,et al.Chemical structures of macrocyclic bis(bi benzyls) isolated from liverworts(Hepaticae).Spectroscopy.2000,14:149-175
66 Tori M,Toyota M,Harrison LJ,et al.Total assignment of ~1H and ~(13)C NMR spectra of Marchantins isolated from liverworts and its application to structure determination of two new macrocyclic bis(bibenzyls) from Plagiochasma intermedium and Riccardia multifida.Tetrahedron Lett.1985,26:4735-4738
67 Asakawa Y,Tori M,Masuya T.Ent-sesquiterpenoids and cyclic bis(bibenzyls) from the German liverwort Marchantia polymorpha.Phytochemistry.1990,29(5):1577-1584
68 王凤强,娄红祥.无纹紫背苔化学成分的研究.药学学报.2000,35(8):587-591
69 Toyota M,Tori M,Takikawa K,et al.Perrottetins E,F and G from Radula perrottetii(Liverwort)-isolation,structure determination and synthesis of perrottetin E.Tetrahedron Lett.1985,26:6097-6100
70 Asakawa Y,Tod M,Krishnamurty H.G.Cyclc bis(bibenzyls) and related compounds from the liverworts Marchantia polymorpha and Marchantia Palmata.Phytochemistry.1987,26(6):1811-1816
71.Asakawa Y,Cannolly EO.Terpenoids and bibenzyls from some NewZlealand liverworts.Phytochemistry.1982,21:2663-2668
72 Kraut L,Klein R,Mues R.Z.Naturforsch.C.1992,47:794
73 李晓强,武静莲,曹斐华,等.白花泡桐叶化学成分的研究.2008,31(6):850-852
74 夏萍芳,李仲辉.香港地钱抗菌化学成分研究.天然产物研究与开发.2001,13(5):15-17
75 Anton H,Kraut L,Mues R.Phenanthrenes and bibenzyls from a Plagiochila species.Phytochemistry.1997,46(6):1067-1075
76 Hegedus LS,Evans BR,Korte DE,E.L.et al.Reactions of.pi.-allylnickel bromide complexes with quinones.Synthesis of isoprenoid quinines.J Am Chem Soc.1976,98(13),3901-3909
77 Gabriele MK,Anthony DW,~1H and ~(13)C-NMR and biological activity investigations of four lichen-derived compounds.Phytochem Anal.1999,10(5):279-284
78 Hashimoto T,Asakawa Y,Nakashima K.Chemical Constituents of 25Liverworts.J Hattori Bot Lab.1993,74,121
79 谭建文,董泽军,刘吉开.鳞盖红菇中一个新的倍半萜类化合物.植物学报.2001,43(3):329-330
80 李光耀,娄红祥,王浩.盔瓣耳叶苔化学成分研究.中草药.2001,32(8):678-681
81.Catalano S,Marsili A,Morelli I,et al.Tfiterpenoids and fatty acids from some mosses obtusifoliol from Racomitrium lanuginosum.Phytochemistry.1976,15(7):1178-1179
82 刘岱琳,庞发根,张家欣,等.密花石豆兰的化学成分研究.中国药物化学杂志.2005,15(2):103-108
83 张海娟.五种植物的化学成分及其生物活性研究.山东大学博士学位论文,2007
84 Kimura J,Maki N.New Loliolide Derivatives from the Brown Alga Undaria pinnatifida.J Nat Prod.2002,65,57-58
85 Seeger T,Geiger H,Zinsmeister HD,et al.Biflavonoids from the moss Homalothecium lutescens.Phytochemistry.1993,34(1):295-296
86 Fan WQ,Xiong MX,Ma Z,et al.Chemical Constituents of Alte rnanthera philoxeroides.Chin J Nat Med.2008,6(2):112-115
87 王小宁,娄红祥.扁枝藓化学成分研究.中国药学杂志.2005,40(15):1131-1133