五味子科药用植物亲缘学初探

五味子科Schisandraceae隶属于双子叶植物门木兰亚纲Magnoliidae八角目Illiciales, 全球分布约60种, 包括两个属: 五味子属Schisandra和南五味子属Kadsura, 间断分布于亚洲东南部和北美东南部。本文归纳了中国五味子科植物两大类活性成分--木脂素和三萜的分布规律、传统疗效和现代药理活性, 并对中国五味子科的药用植物亲缘学进行了初探。联苯环辛烯类木脂素(I)集中分布于五味子科植物, 可以被认为是五味子科植物的特征性化学成分, 除了传统的保肝作用外, 这类化合物中很多具有潜在的抗氧化、抗肿瘤和抗HIV活性, 一些联苯环辛烯类的木脂素, 尤其是在八元环C-6、C-9位上具有羟基或者酯化取代具有更好的抗HIV和抗肿瘤活性; 而螺苯骈呋喃型联苯环辛烯类木脂素(II)绝大多数存在于南五味子属, 其特殊的螺苯骈呋喃环及其钙拮抗、抗凝血和抑制血小板聚集的活性, 不仅初步说明了民间南五味子属药用植物藤茎具有较强活血化瘀药理作用的活性物质基础, 也提示在对南五味子属的药材质量标准研究中, 可以考虑以此类成分作为定性定量指标。五味子科植物中木脂素成分的分布规律提示, 在演化程度上五味子属植物较南五味子属植物更原始。环菠萝蜜烷类三萜在五味子属和南五味子属均有分布, 尤其是A环开环的环菠萝蜜烷类三萜(II)在抗HIV和抗肿瘤活性方面具有很好的潜力, 而结构更进化的7/7/5/6型三萜内酯(IV)显示了很强的细胞毒活性, 目前只在南五味子属的长梗南五味子K. longipedunculata中发现。从五味子属的小花五味子S. micrantha和狭叶五味子S. lancifolia中分离得到的多个成环复杂且高度氧化的类三萜内酯中也发现具有抗肿瘤和抗HIV潜力。     

五味子科植物的木脂素成分

五味子科植物分为五味子属 ( Schisandra)和南五味子属 ( Kadsura) 2个属 ,其中五味子 ( S.chinensis)为著名中药 ,其应用已有 2 0 0 0多年的历史 ,一直为我国药典所收载 ,该科其它许多种也在民间广泛应用 [1 ]。 2 0世纪 70年代初 ,我国临床研究中发现五味子能明显降低肝炎患者血清谷丙转氨酶水平 ,引起广泛研究的热潮 ,并由此开发出治疗肝炎药物联苯双酯 [2 ] 。迄今 ,国内外已对二十余种五味子科植物进行了研究 ,分离鉴定出大约 2 0 0个成分 ,其中 1 50多个为木脂素。五味子科木脂素结构类型多 ,立体化学复杂 ,而且生物活性广泛。除了…     

五味子属植物木脂素类资源的研究

本文调查了15个省区71个样品的15种五味子属植物。应用高效液相色谱法,对8种木脂素有效成分在五味子属植物中的含量进行了分析,这8种木脂素提五味子醇甲(schizandrol A)、醇乙(schizandrol B)、酯甲、酯乙(gomisinC,B)、五味子酚(schizanhenol)、甲素(deoxyschizandrin)、乙素(γ-schizandrin)及丙素(schizandrin C),同时对12种五味子的醇提物进行了主要药理作用的比较。根据研究结果,对各种五味子的质量作出评价以及可供开发利用的意见。     

正交设计优选五味子果实中总木脂素提取工艺

目的:比较不同方法对北五味子总木脂素提取的影响,优选最佳提取工艺方法。研究五味子木脂素抗微波辐射损伤作用。方法:以干燥北五味子果实为原料,分别采用传统加热回流法、超声提取法、微波提取法、微波—超声提取法提取北五味子总木脂素,对这四种提取方法分别进行正交试验分析,以确定最佳提取工艺。结果:通过结果比较分析,以微波提取工艺结果最佳,在微波提取功率为200W,乙醇体积分数为80%,提取时间为40min,料液比为1:12的提取条件下,北五味子总木脂素的产量达到了16.44mg/g,使得木脂素的提取产量较传统加热回流法、超声提取法、微波—超声提取法得到了显著的提高。     

南五味子药材UPLC指纹图谱及一测多评法研究

建立南五味子药材超高效液相色谱(UPLC)指纹图谱和6种木脂素类成分一测多评法(QAMS),为南五味子药材质量标准提高提供参考。采用UPLC法建立南五味子药材指纹图谱,运用聚类分析(HCA)和正交偏最小二乘法-判别分析(OPLS-DA)对指纹图谱进行分析;以五味子酯甲为内参物,建立五味子酯丙、五味子酯乙、安五脂素、五味子甲素和五味子酯丁的一测多评法,并与外标法(ESM)测定结果对比,判断方法的准确性。14批南五味子药材指纹图谱确定了15个共有峰,通过对照品比对指认了其中7个成分,分别为原儿茶酸、五味子酯丙、五味子酯甲、五味子酯乙、安五脂素、五味子甲素、五味子酯丁,其指纹图谱相似度均在0.95以上;通过聚类分析(HCA)和正交偏最小二乘法-判别式分析(OPLS-DA)可以将南五味子药材分为4类,峰1(原儿茶酸)、峰2、峰4、峰6、峰7(五味子酯乙)、峰8、峰9、峰12、峰15共9个成分是导致产地差异性的主要标志物。一测多评法与外标法测定的五味子酯丙、五味子酯乙、安五脂素、五味子甲素和五味子酯丁含量结果无显著差异。所建立的方法简便、可靠,为南五味子药材质量评价提供参考。     

抗癌活性物质鬼臼类木脂素的研究进展

本文概述了抗癌活性物质鬼臼类木脂素的生物合成、抗癌机理、生药分布以及利用植物细胞培养技术生产鬼臼类木脂素的研究进展;并介绍了目前应用于该研究领域的一些新的技术方法。     

五味子抗氧化及抑制α-葡萄糖苷酶活性的比较研究

筛选出五味子抗氧化活性最强及α-葡萄糖苷酶活性的抑制作用最优的部位。对各提取物及有效部位进行含量测定。以对DPPH·清除能力和铁离子还原能力代表其抗氧化活性,比较五味子各提取部位的抗氧化活性。以4-硝基苯-α-D-吡喃葡萄糖苷(PNPG)为底物,阿卡波糖(ACAR)为阳性对照,对各提取部位的α-葡萄糖苷酶活性的体外抑制作用进行比较。采用Origin 8软件中的多项拟合计算活性实验的IC50值及Abs0.7值,并采用皮尔森相关性分析测定活性成分含量与抗氧化活性和α-葡萄糖苷酶抑制活性间的相关性。五味子药材中含量最高的是总多糖类物质,含量为72.9 mg GL/g DM,其次为总酚酸类物质,含量为46.8 mg GA/g DM,木脂素类物质含量为39.6 mg SC/g DM,三萜类物质含量为32.2 mg OL/g DM,总黄酮类物质含量最低,为22.6 mg RU/g DM。五味子各有效部位抗氧化活性顺序为:总木脂素总黄酮总三萜总酚酸总多糖。对α-葡萄糖苷酶活性抑制作用最强的为总木脂素(IC50值为0.24),抑制作用最弱的为总三萜。五味子70%乙醇提取物和乙酸乙酯萃取物的抗氧化活性和α-葡萄糖苷酶活性抑制作用最优。五味子中总木脂素具有最优的抗氧活性及α-葡萄糖苷酶活性抑制活性。抗氧活性和α-葡萄糖苷酶活性抑制活性与木脂素类物质的含量呈正相关。     

锦葵科植物的苯丙素类及相关化学成分研究进展

综述了锦葵科植物的简单苯丙素、木脂素、香豆素,木脂素并香豆素等苯丙素类化学成分、药理作用等方面的研究进展。     

超高液相色谱法同时测定北五味子中7种木脂素类化合物

建立了超高效液相色谱法(UPLC)同时测定北五味子中7种主要木脂素类成分的检测方法。采用ACQUITY UPLC~BEH C_(18)色谱柱(50 mm×2.1 mm,1.7μm);以水-乙腈为流动相,梯度洗脱分离,PDA检测波长254 nm,流速0.4 m L/min,柱温30℃,进样量2μL。优化了色谱分离条件,并进行了线性方程、准确度、重复性、回收率等方法学考察,在优化条件下,7种木脂素的出峰时间在5 min内,且线性关系良好(r0.9994),方法检出限范围为0.0105~0.1600μg/m L,定量限为0.1050~0.8200μg/m L,相对标准偏差(RSD)在0.0340%~1.3800%之间,样品加样回收率在95.09%~104.50%范围内。本方法大大缩短了分析时间,灵敏度高,适用于北五味子中7种木脂素类成分的同时测定。     

野生中泰南五味子果实的形态及营养成分分析

中泰南五味子( Kadsura ananosma Kerr )为五味子科( Schisandraceae)南五味子属( Kadsura Kaempf. ex Juss.)攀缘植物[1]14,其根、藤茎、果实是珍贵的傣药,具有收敛固涩、益气生津、补肾宁心的作用。对中泰南五味子化学成分的研究结果表明：中泰南五味子体内含有较多的木脂素类和三萜类成分,其中20多个成分为其特有成分,这些成分具有抗氧化、抗HIV病毒等药理活性[2-5]。中泰南五味子果实具有果大、肉多、酸甜可口等特点,还可作为野生水果食用,但目前对中泰南五味子果实的相关研究尚未见报道;相关志书[1]15,[6]234对其果实的基本描述也不完整,甚至空缺。为此,作者对野生中泰南五味子果实的形态特征进行观察,并对其营养成分进行分析,以期完善中泰南五味子果实的基础研究数据,为其深入开发和利用提供依据。     

国产五味子科五种植物叶片脉序研究

首次报道了国产五味子科５种植物的叶脉特征,对科、属、种的特征作了描述,编排有分种检索表．通过与八角科叶脉的比较,支持建立五味子科与八角科的观点,认为五味子属的系统位置在南五味子属之后,并讨论了八角目的演化趋势     

五味子科比较木材解剖及其系统学意义

在光学显微镜和扫描电镜下观察了南五味子属Kadsura 7种21个样品和五昧子属Schisandra 8种14个样品的木材解剖特征,结果表明次生木质部的导管分子类型、导管一射线间纹孔的排列方式、射线类型、射线细胞形状等性状在科的水平上很稳定,这些共同特征都支持五味子科Schisandraceae是比较自然的类群。在五昧子科中发现木材导管单生、具梯状穿孔板、导管壁具梯形排列的纹孔以及木射线异型等原始性状,支持五味子科在被子植物中的原始地位。此外,该科木材还具有单穿孔板导管、导管次生壁具螺纹加厚、具分隔纤维等较为特化的性状状态,这种性状进化水平的异等级现象,使五味子科表现出不同进化水平性状的镶嵌组合。根据木材解剖性状对五味子科进行UPGMA聚类分析,所得结果显示南五昧子属和五味子属在木材解剖特征方面有一定的交叉和重叠,这与分子系统学的结论一致,表明这两个属关系密切,可能起源于共同的祖先。通过比较五昧子科与八角科Illiciaceae的木材解剖特征,进一步证明两个科的亲缘关系很近,不支持将五味子科从八角目Illiciales中独立出来成立五味子目Schisandrales的观点。     

Phylogeny of Schisandraceae based on morphological data: evidence from modern plants and the fossil record

Schisandraceae are traditionally subdivided in two genera, Schisandra and Kadsura, based on differences in the organisation of the floral receptacle, the carpels, and the presence or absence of a ``pseudostigma'. Recently, phylogenetic analyses utilizing ITS sequence data and morphological data resulted in incongruent tree topologies, with the morphological trees suggesting monophyly of the two genera, whereas ITS trees did not resolve Schisandra and Kadsura as monophyletic clades. In the present paper we study seed morphology and leaf epidermal features of 22 species of Schisandraceae in order to provide additional data for a morphological data matrix. Seed morphological characters are highly homoplastic and do not yield further evidence for monophyly of the two genera. Instead, a number of characters appear to support sister group relationships between taxa within the genera, such as, for instance, for K. coccinea and K. scandens, both of which have large seeds along with a multi-layered mesotesta. Considering leaf epidermal characteristics, species of Kadsura were found to be consistently amphistomatic, whereas species of Schisandra are always hypostomatic. Phylogenetic analysis using the extended data matrix resulted in weakly supported Kadsura and Schisandra clades with five and four synapomorphies indicating monophyly of Kadsura and Schisandra, respectively. Fossils ascribed to Schisandraceae date back to the Late Cretaceous. These are tri-and hexacolpate pollen types displaying a combination of features found in modern Schisandraceae and partly also in Illiciaceae. Leaf remains from this period are poorly preserved and difficult to ascribe to Schisandraceae because of the lack of synapomorphies for the family. In the Early Cainozoic, leaf and seed remains from North America and Europe unambiguously belong to the family. Seeds from the Eocene of North America show some similarities to the modern Schisandra glabra from North America, while fossils from Europe show more similarities to modern Asian species.     

Phylogeny of the Schisandraceae based on cpDNA mat-K and rpL16 intron data

The chloroplast mat-K region and rpL16 intron region were sequenced for 14 species of Schisandraceae, representing both genera Kadsura Kaempf. ex Juss. and Schisandra Michx, to discuss the phylogeny of this family. Analyses were performed both in separate and combined sequence data sets (including the rbc-L sequence), with Illicium angustispealum A. C. Smith as the out-group. The results showed that the Schisandraceae are monophyletic. In all the analyses, Schisandra propinqua var. chinensis Oliva and Schisandra plena A. C. Smith were nested within Kadsura, which implies that the genera Kadsura and Schisandra are closely related. They might have originated from a common ancestor, but then evolved via different routes. The result inferred from the combined data showed a greater resolution within Schisandra than those from the two separate data sets. High bootstrap values supported the monophyly of most subgenera according to Law's system (1996). A combination of morphological, anatomical, and chemical analyses indicates that S. chinensis and S. rubriflora may be the primitive taxa in Schisandra.     

Morphological characters of leaf epidermis in schisandraceae and their systematic significance

The leaf epidermis of 23 species belonging to 2 genera within Schisandraceae was investigated using light and scanning electron microscopy. Many characters of the leaf epidermis in Schisandraceae, such as shape of epidermal cells, type of stomata, and cuticular ornamentation, are usually constant within species and thus helpful for elucidating the relationship between and within genera. Leaf epidermal cells are usually irregular or polygonal in shape. The patterns of anticlinal walls are straight, sinuolate, sinuous or sinuate. The stomatal apparatus belong to paracytic or laterocytic type and the latter is subdivided into various subtypes based on the number and arrangement of subsidiary cells. Under scanning electron microscopy observation, the cuticular membrane is often striated, sometimes squamulate or granular; the inner margin of the outer stomatal rim is nearly smooth or denticulate. Evidences from shape of epidermal cells, patterns of cuticular intrusions between the ends of each guard cell of a pair and distribution of stomatal apparatuses support the viewpoint thatKadsura is more primitive thanSchisandra. Study on leaf epidermis also shows thatKadsura interior deserves the rank of a distinct species and the treatment of the evergreen groups, includingS. propinqua andS. plena, as distinct from the deciduous species of the genus is quite natural.     

五味子科植物花形态及其系统学意义

用光镜和扫描电镜观察了五味子科Ｓｃｈｉｓａｎｄｒａｃｅａｅ２３种、６变种和１变型的９１份花粉的形态。其中５ 、４变种和１变型的花粉形态为首次报道。该科花粉为单花粉,异极,辐射对称,扁球形至超扁球形,其萌发沟的排列格局在被子植物中是独一无二的。若按萌发沟的数目划分,该科花粉可分为３沟型和６沟型两个类型。外壁为网状纹饰,网眼的大小和网脊的宽度与花的形态有一定相关性。研究结果不支持Ｐｒａｇｌｏｗｓｋｉ对     

八角目(Illiciales)植物花被片表皮比较形态

在光学显微镜和扫描电镜下,观察了八角科(Illiciaceae)八角属(Illicium Linn.)2组11种20个材料、五味子科(Schisandraceae)南五味子属(Kadsura Ksempf. ex Juss.)2亚属2组8种15个材料和五味子属(Schisandra Michx.)2亚属4组6种17个材料的花被片表皮形态特征。首次报道了八角目2个科（八角科和五味子科）3个属（八角属、南五味子属和五味子属）植物花被片表皮细胞的形状、分泌细胞的形状及分布、气孔器的形状及分布、花被片表面的纹饰。通过与八角目2个科3个属植物的叶表皮形态比较,发现花被片表皮气孔器外拱盖均为单层,与叶表皮气孔器外拱盖层数（常绿种类为双层和落叶种类为单层）之间没有相关性,还在五味子科中发现2个新的性状（气孔对和环列型气孔）。通过对两性花、雌花和雄花花被片表皮观察,发现花被片表皮形态与花的性别之间没有相关性。通过对八角属、南五味子属和五味子属花被片表皮比较,发现五味子属与南五味子属相比,其花被片表皮表现出更多的衍生性状;南五味子属与八角属相比,前者花被片表皮具有更多的衍生性状;而南五味子属花被片表皮形态与五味子属的相似性程度较大,支持五味子科包含南五味子属和五味子属、八角科包含八角属的观点。     

Pollen morphology of the Schisandraceae and its systematic significance

Pollen morphology of 91 samples, representing 23 species, 6 varieties and 1 form of the Schisandraceae, was examined under light microscope (LM) and scanning electron microscope (SEM). Palynological data of 5 species, 4 varieties and 1 form are reported for the first time. The pollen grains are monads, heteropolar, radiosymmetric and oblate to peroblate in shape. Arrangement of their colpi is unique in angiosperms. The pollen grains can be divided into two types according to the number of their clopi: the tricolpate pollen type and the hexacolpate pollen type. The exine sculpturing is reticulate. The size of luminae and the breadth of muri are correlated with the floral morphology of the hisandraceae to a certain extent. Our results do not support the division of the pollen grains of the Schisandraceae into 4 types according to the size of inae as proposed by Praglowski. There is also still room of discussion about his conclusion that the pole where the three longer colpi converge is the distal pole. The evolutionary trends of the pollen grains of the Schisandraceae seem to be from fewer to more in the number of colpi, and from smaller to larger in the size of luminae. The view that Kadsura is more primitive than Schisnadra is not supported by palynological data; on the contrary, Kadsura seems to be more advanced than Schisandra at the general level of evolution. The two genera may be closely related, and might have originated from a common ancestor and then evolved parallelly along two different routes.     

On the laterocytic stomatotype in angiosperms

The laterocytic type of stomatal apparatus in angiosperms is considered. Investigation of the stomatal apparatus of 18 species of Hamamelidaceae, representing 15 genera, showed that in addition to the anomocytic, paracytic, and encyclocytic stomatotypes previously known in the family, the laterocytic type is found in several genera (Dicoryphe, Exbucklandia, and others). Study of 15 species of Chloranthaceae, representing all five genera, showed that laterocytic stomates occur inChloranthus andSarcandra and sometimesHedyosmum, along with stomates of other types.Barbeya oleoides (Barbeyaceae) and the four investigated species ofBalanops (Balanopaceae) have exclusively (or inB. oliviformis mainly) laterocytic stomates. Laterocytic stomates are present also inKadsura andSchisandra of the Schisandraceae, along with the previously known paracytic type. In addition to the foregoing genera, laterocytic stomates are known in some members of the Buxaceae, Celastraceae, Crypteroniaceae, Hydrangeaceae, Icacinaceae Platanaceae, Tetracentraceae and Trochodendraceae.     

国产五味子科植物导管分子的比较解剖

对五味子科 2属 1 9种植物导管分子的结构进行了比较观察。结果表明 :2属均以具缘纹孔导管为主 ,少有梯纹和螺纹导管 ,南五味子属多数种还有梯孔纹导管 ;2属导管长度和宽度差异很小 ,长 /宽比值有差异 ;根据穿孔板的结构可分为 2种形式 :( 1 )单穿孔板 ,这类穿孔板较普遍存在 ;( 2 )梯形穿孔板 ,发现 2属中的红花五味子 (Schisandrarubriflora)、五味子 (S .chinensis)、翼梗五味子 (S .henryi)、铁箍散 (S .propinquavar.sinensis)和黑老虎 (Kadsuracoccinea) 5种植物的导管分子具有此类穿孔板。其中五味子属中的五味子导管分子只具有梯形穿孔板 ,无单穿孔板 ,但横条较少 ,多为 2～ 3条。