六种苔类植物的化学成分及其生物活性
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摘要
苔藓植物形态学上可分为藓纲(Musci)、苔纲(Hepaticae)和角苔纲(Anthocerota)三类植物,在系统发育学上位于藻类和蕨类植物之间,是植物界由水生向陆生过渡的高等植物类群。尽管在植物进化谱上处于较低的位置,近年来从苔藓植物中分离获得了大量结构新颖且活性显著的刺激代谢产物,其中许多可作为新药研究的良好先导化合物。在民间,苔藓被广泛用于治疗外伤、烧伤、感染、肺结核、神经衰弱、惊厥、烫伤和肺炎等症。苔纲植物在全球约6000余种,我国约880余种。近年来,对苔类植物的化学成分研究较多,因为这类植物细胞中含有油体,其中富含脂溶性萜类和芳香类化合物,很多次级代谢产物表现出良好的生物活性。
本文对采自中国的六种苔类植物,包括采自四川的粗裂地钱,采自贵州的小蛇苔、白叶鞭苔、广口平叶苔和刺边合叶苔,以及采自云南的卷叶类钱袋苔的化学成分进行了系统的研究,分离得到了72个次级代谢产物,其中24个为新化合物。通过核磁共振、质谱、X射线单晶衍射以及含时密度泛函理论CD计算等方法鉴定了这些化合物的结构。初步研究了分得的化合物的生物活性,发现双联苄类化合物具有中等抗肿瘤活性,海松烷型二萜具有化感活性,可以抑制拟南芥根部的生长。对白叶鞭苔、广口平叶苔和卷叶类钱袋苔的成分研究尚属首次。
通过柱层析以及半制备HPLC等分离手段,从粗裂地钱乙醚提取物中分离并鉴定了23个化合物,包括10个双联苄,1个单联苄,2个菲类化合物,2个单苯环衍生物,6个三萜和2个甾体。研究了分离得到的双联苄对8种肿瘤细胞的细胞毒活性。研究发现,部分双联苄化合物显示较好的细胞毒活性,其中Neomarchantin A (3)和Riccardin C (8)对人肺腺癌细胞株A-549作用突出,对其它细胞株作用不明显。
从小蛇苔乙醚相中分得16个化合物,采用一维和二维NMR以及高分辨MS等波谱法对其结构进行了鉴定,其中3个为新化合物,包括2个ArC2二聚体cis-和trans-1,2-bis(3,4-dimethoxyphenyl)cyclobutane (24和25),以及一个单萜酯,2α,5β-dihydroxybornane-2-cis-cinnamate(26)。其他化合物均为首次从该植物中分离得到。24是从苔类植物中分得的第二个ArC2二聚体类化合物,结合以往的研究对ArC2二聚体类化合物的生源合成途径进行了探讨。采用MTT法筛选分离得到的化合物单萜酯以及双联苄对人类肿瘤细胞KB的体外细胞毒活性。
从白叶鞭苔乙醚相中分得14个化合物,包括1个新的6,7-开环壳梭孢烷型二萜：albifolione (36),和1个新的香橙烷型倍半萜methyl-2-oxo-1(10),3-dien-aromadendren-12-oate (37)。36是首次从天然产物中分离得到具有6,7-开环骨架的壳梭孢烷型二萜。抗真菌实验结果显示其主要成分45对白色念珠菌具有一定的抑制作用,MIC值为16μg/mL。抗肿瘤实验结果显示46对MCF-7细胞作用较为显著,IC50值为5.6μM。
从广口平叶苔中分离得到10个新的海松烷型二萜,包括pedinophyllols A-J(52-62)。其中,61是从苔类植物中分得的第一个含有14α,16-坏氧结构的海松烷型二萜。通过NMR、CD、X射线单晶分析,以及含时密度泛函理论CD计算确定新化合物的绝对构型。化感活性显示大部分二萜可以抑制拟南芥根部的生长,其中,化合物52在7.8μg/mL时可以显著抑制拟南芥根部的生长。提示他们在苔藓植物抵抗外界环境胁迫方面有一定的作用。
从卷叶类钱袋苔中分离得到5个新的桉烷型倍半萜(63-68),其中67和68为比较少见的三降倍半萜。化合物66对白色念珠菌具有较弱的抗真菌作用,MIC值为128μg/mL,但它与氟康唑联用具有相加的效果。另外,本研究为该种植物的化学分类学研究提供依据。
从刺边合叶苔中分离得到4个新的克罗烷型二萜化合物(69-72),其中包括一个四降克罗烷型二萜骨架(69),通过参考文献分析,NMR数据,以及X-单晶衍射确定了化合物的结构。
The bryophytes [Musci (mosses), Marchantiophyta (liverworts) and Anthocerotae (homworts)], are morphologically placed between the algae and the pteridophytes (fern). Bryophytes, considered being the first plant type to successfully make the transition from water to land, have yielded various secondary metabolites with interesting chemical structures and significant biological activity. Now the bryophytes have been well known as a source of biologically active, naturally occurring compounds. As a Chinese folk medicine, the bryophytes have been used as medicinal plants to cure cuts, burns, bacteriosis, pulmonary tuberculosis, neurasthenia, convulsions, scalds, pneumonia, and so on. There are more than6000liverworts worldwide, among about880species of which have been found in china. Among the bryophyte species, liverworts have been phytochemically investigated in most detail because they possess cellular oil bodies, which are rich sources of lipophilic terpenoids and aromatic compounds, while the other two classes do not contain such oil bodies. Many of the isolated compounds from liverworts exhibit attractive biological activities.
In this research of six Chinese liverworts, Marchantia polymorpha collected from Sichuan Province, Conocephalum japonicum, Bazzania albifolia, Pedinophyllum interruptum, and Scapania ciliata collected from Guizhou Province, and Apomarsupella revolute collected from Yunnan Province were phytochemically investigated. A total of72secondary metabolites were isolated and identified on the basis of NMR, MS, X-ray, and time-dependent density functional theory (TDDFT) CD calculations, containing24new compounds. The bisbibenzyls exhibited moderate cytotoxicity and antifungal activities. Activity test showed that the bisbibenzyls exhibited moderate cytotoxicity and the highly oxygenated ent-pimarane-type diterpenoids inhibited germination of the Arabidopsis thaliana seeds. This work represents the first phytochemical study on the plants of Bazzania albifulia, Pedinophyllum interruptum, and Apomarsupella revolute.
From an Et2O extract of M. polymorpha,23compounds were isolated by repeated column chromatography on Si gel and Sephadex LH-20, followed by semipreparative high-performance liquid chromatography (HPLC), which were characterized as10bisbibenzyls,1bisbibenzyl,2naphthalenes,2single benzene derivatives,6triterpenoids and2steroids. The cytotoxicity of10bisbibenzyls was evaluated against eight human tumor cells lines. Neomarchantin A (3) and Riccardin C (8) exhibited significant cytotoxicity against Human lung tumor A-549cell.
From the ether extract of the liverwort C. japonicum,16compounds, including two undescribed dimeric ArC2derivatives, cis-and trara-1,2-bis(3,4-dimethoxyphenyl)cyclobutane (24and25), one new monoteipenes esters,2α,5β-dihydroxybomane-2-cis-cinnamate (26), along with eight known compounds were isolated. All the structures were established by extensive spectroscopic analysis. Up to date, this is the second report on naturally occurring cyclobutane derivatives isolated from the liverworts. Suggested biosynthetic pathway for24and25was proposed. Cytotoxicity of monoterpenes esters and bisbibenzyls to human tumor KB cell was tested by MTT.
18compounds were isolated from the ether extract of the liverwort B. albifolia (36-51), including one undescribed6,7-secofusicoccane-type diterpene, albifolione (36), and one new aromadendrane-type sesquiterpenoid ketone, methyl-2-oxo-1(10),3-dien-aromadendren-12-oate (37). Compound36was the first naturally occurring diterpenoid with a cleaved fusicoccane framework. Preliminary bioassay found that main compound45exhibited moderate antifungal effects with the MIC values of16μg/ml. Compound46showed quite strong cytotoxicity against the human tumor cell line MCF-7, with IC50value of5.63μM.
Ten highly oxygenated ent-pimarane-type diterpenoids pedinophyllols A-J (52-62) have been isolated from the Chinese liverwort Pedinophyllum interruptum. Their structures were determined by comprehensive analysis of spectroscopic data together with single-crystal X-ray diffraction analysis. The absolute configuration was achieved by analysis of the CD spectra and by quantum chemical CD calculations. Allelopathic test showed that some of these diteipenoids inhibit germination of the Arabidopsis lhaliana seeds. Among them, compound52significantly retarded the Arabidopsis seeds germination at7.8μg/mL, which indicated that they could also play a role as allelochemicals for liverwort to defense against other plants.
Phytochemical investigation of the Et2O extract of liverwort Apomarsupella revolute led to isolation and identification of five new eudesmane-type and a deacetylation product (63-68), two of which were trinorsesquiterpenoids. Compound63exhibited weak antifungal effects with the MIC value of128μg/mL. The combination treatment of63and FLC showed additive effect against C. albicans. This work shed lights on chemotaxonomy and chemical ecology of this liverwort species.
Four clerodane diterpenoids (69-72) were isolated from the liverwort Scapania ciliate.69is the first clerodane quadrinorditerpenoid from the liverworts. Their structures were determined by NMR, X-ray, and comparison of their NMR data with those reported in the literatures.
本文对采自中国的六种苔类植物,包括采自四川的粗裂地钱,采自贵州的小蛇苔、白叶鞭苔、广口平叶苔和刺边合叶苔,以及采自云南的卷叶类钱袋苔的化学成分进行了系统的研究,分离得到了72个次级代谢产物,其中24个为新化合物。通过核磁共振、质谱、X射线单晶衍射以及含时密度泛函理论CD计算等方法鉴定了这些化合物的结构。初步研究了分得的化合物的生物活性,发现双联苄类化合物具有中等抗肿瘤活性,海松烷型二萜具有化感活性,可以抑制拟南芥根部的生长。对白叶鞭苔、广口平叶苔和卷叶类钱袋苔的成分研究尚属首次。
通过柱层析以及半制备HPLC等分离手段,从粗裂地钱乙醚提取物中分离并鉴定了23个化合物,包括10个双联苄,1个单联苄,2个菲类化合物,2个单苯环衍生物,6个三萜和2个甾体。研究了分离得到的双联苄对8种肿瘤细胞的细胞毒活性。研究发现,部分双联苄化合物显示较好的细胞毒活性,其中Neomarchantin A (3)和Riccardin C (8)对人肺腺癌细胞株A-549作用突出,对其它细胞株作用不明显。
从小蛇苔乙醚相中分得16个化合物,采用一维和二维NMR以及高分辨MS等波谱法对其结构进行了鉴定,其中3个为新化合物,包括2个ArC2二聚体cis-和trans-1,2-bis(3,4-dimethoxyphenyl)cyclobutane (24和25),以及一个单萜酯,2α,5β-dihydroxybornane-2-cis-cinnamate(26)。其他化合物均为首次从该植物中分离得到。24是从苔类植物中分得的第二个ArC2二聚体类化合物,结合以往的研究对ArC2二聚体类化合物的生源合成途径进行了探讨。采用MTT法筛选分离得到的化合物单萜酯以及双联苄对人类肿瘤细胞KB的体外细胞毒活性。
从白叶鞭苔乙醚相中分得14个化合物,包括1个新的6,7-开环壳梭孢烷型二萜：albifolione (36),和1个新的香橙烷型倍半萜methyl-2-oxo-1(10),3-dien-aromadendren-12-oate (37)。36是首次从天然产物中分离得到具有6,7-开环骨架的壳梭孢烷型二萜。抗真菌实验结果显示其主要成分45对白色念珠菌具有一定的抑制作用,MIC值为16μg/mL。抗肿瘤实验结果显示46对MCF-7细胞作用较为显著,IC50值为5.6μM。
从广口平叶苔中分离得到10个新的海松烷型二萜,包括pedinophyllols A-J(52-62)。其中,61是从苔类植物中分得的第一个含有14α,16-坏氧结构的海松烷型二萜。通过NMR、CD、X射线单晶分析,以及含时密度泛函理论CD计算确定新化合物的绝对构型。化感活性显示大部分二萜可以抑制拟南芥根部的生长,其中,化合物52在7.8μg/mL时可以显著抑制拟南芥根部的生长。提示他们在苔藓植物抵抗外界环境胁迫方面有一定的作用。
从卷叶类钱袋苔中分离得到5个新的桉烷型倍半萜(63-68),其中67和68为比较少见的三降倍半萜。化合物66对白色念珠菌具有较弱的抗真菌作用,MIC值为128μg/mL,但它与氟康唑联用具有相加的效果。另外,本研究为该种植物的化学分类学研究提供依据。
从刺边合叶苔中分离得到4个新的克罗烷型二萜化合物(69-72),其中包括一个四降克罗烷型二萜骨架(69),通过参考文献分析,NMR数据,以及X-单晶衍射确定了化合物的结构。
The bryophytes [Musci (mosses), Marchantiophyta (liverworts) and Anthocerotae (homworts)], are morphologically placed between the algae and the pteridophytes (fern). Bryophytes, considered being the first plant type to successfully make the transition from water to land, have yielded various secondary metabolites with interesting chemical structures and significant biological activity. Now the bryophytes have been well known as a source of biologically active, naturally occurring compounds. As a Chinese folk medicine, the bryophytes have been used as medicinal plants to cure cuts, burns, bacteriosis, pulmonary tuberculosis, neurasthenia, convulsions, scalds, pneumonia, and so on. There are more than6000liverworts worldwide, among about880species of which have been found in china. Among the bryophyte species, liverworts have been phytochemically investigated in most detail because they possess cellular oil bodies, which are rich sources of lipophilic terpenoids and aromatic compounds, while the other two classes do not contain such oil bodies. Many of the isolated compounds from liverworts exhibit attractive biological activities.
In this research of six Chinese liverworts, Marchantia polymorpha collected from Sichuan Province, Conocephalum japonicum, Bazzania albifolia, Pedinophyllum interruptum, and Scapania ciliata collected from Guizhou Province, and Apomarsupella revolute collected from Yunnan Province were phytochemically investigated. A total of72secondary metabolites were isolated and identified on the basis of NMR, MS, X-ray, and time-dependent density functional theory (TDDFT) CD calculations, containing24new compounds. The bisbibenzyls exhibited moderate cytotoxicity and antifungal activities. Activity test showed that the bisbibenzyls exhibited moderate cytotoxicity and the highly oxygenated ent-pimarane-type diterpenoids inhibited germination of the Arabidopsis thaliana seeds. This work represents the first phytochemical study on the plants of Bazzania albifulia, Pedinophyllum interruptum, and Apomarsupella revolute.
From an Et2O extract of M. polymorpha,23compounds were isolated by repeated column chromatography on Si gel and Sephadex LH-20, followed by semipreparative high-performance liquid chromatography (HPLC), which were characterized as10bisbibenzyls,1bisbibenzyl,2naphthalenes,2single benzene derivatives,6triterpenoids and2steroids. The cytotoxicity of10bisbibenzyls was evaluated against eight human tumor cells lines. Neomarchantin A (3) and Riccardin C (8) exhibited significant cytotoxicity against Human lung tumor A-549cell.
From the ether extract of the liverwort C. japonicum,16compounds, including two undescribed dimeric ArC2derivatives, cis-and trara-1,2-bis(3,4-dimethoxyphenyl)cyclobutane (24and25), one new monoteipenes esters,2α,5β-dihydroxybomane-2-cis-cinnamate (26), along with eight known compounds were isolated. All the structures were established by extensive spectroscopic analysis. Up to date, this is the second report on naturally occurring cyclobutane derivatives isolated from the liverworts. Suggested biosynthetic pathway for24and25was proposed. Cytotoxicity of monoterpenes esters and bisbibenzyls to human tumor KB cell was tested by MTT.
18compounds were isolated from the ether extract of the liverwort B. albifolia (36-51), including one undescribed6,7-secofusicoccane-type diterpene, albifolione (36), and one new aromadendrane-type sesquiterpenoid ketone, methyl-2-oxo-1(10),3-dien-aromadendren-12-oate (37). Compound36was the first naturally occurring diterpenoid with a cleaved fusicoccane framework. Preliminary bioassay found that main compound45exhibited moderate antifungal effects with the MIC values of16μg/ml. Compound46showed quite strong cytotoxicity against the human tumor cell line MCF-7, with IC50value of5.63μM.
Ten highly oxygenated ent-pimarane-type diterpenoids pedinophyllols A-J (52-62) have been isolated from the Chinese liverwort Pedinophyllum interruptum. Their structures were determined by comprehensive analysis of spectroscopic data together with single-crystal X-ray diffraction analysis. The absolute configuration was achieved by analysis of the CD spectra and by quantum chemical CD calculations. Allelopathic test showed that some of these diteipenoids inhibit germination of the Arabidopsis lhaliana seeds. Among them, compound52significantly retarded the Arabidopsis seeds germination at7.8μg/mL, which indicated that they could also play a role as allelochemicals for liverwort to defense against other plants.
Phytochemical investigation of the Et2O extract of liverwort Apomarsupella revolute led to isolation and identification of five new eudesmane-type and a deacetylation product (63-68), two of which were trinorsesquiterpenoids. Compound63exhibited weak antifungal effects with the MIC value of128μg/mL. The combination treatment of63and FLC showed additive effect against C. albicans. This work shed lights on chemotaxonomy and chemical ecology of this liverwort species.
Four clerodane diterpenoids (69-72) were isolated from the liverwort Scapania ciliate.69is the first clerodane quadrinorditerpenoid from the liverworts. Their structures were determined by NMR, X-ray, and comparison of their NMR data with those reported in the literatures.
引文
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