杉科的细胞分类学和系统演化研究

根据杉科的核型资料,本文(1)提出“1B”可能是一个新的高等植物核型类型;(2)讨论了各属的有关分类学问题及相互亲缘关系,它们的进化顺序可能是柳杉属、水松属、落羽杉属、水杉属、巨杉属、红杉属、杉木属(密叶杉属与之近缘)、台湾杉属;(3)支持金松属分立成金松科,它可能比杉科各属原始; (4)红杉(AAAABB)的亲本可能是二个古代种“水杉”和“巨杉”,它们的直接后裔或留下的近缘是水杉和巨杉;(5)杉科存在A和L两条进化路线,前者包括柳杉属、水松属、落羽杉属、台湾杉属;后者包括水杉属、巨杉属、红杉属、杉木属(密叶杉属);(6)提出一个杉科新系统(包括一个新亚科):Ⅰ.柳杉亚科(柳杉属),Ⅱ.落羽杉亚科(水松属、落羽杉属),Ⅲ.红杉亚科(水杉属、巨杉属、红杉属),Ⅳ.杉木亚科(杉木属、密叶杉属),Ⅴ.台湾杉亚科,新亚科(台湾杉属)。本文还对前人的杉科系统作了讨论。     

杉科植物的系统发育分析

本文以形态学为依据,参考其他学科的研究成果,用分支分类方法并结合表征分类方法探讨了杉科植物的系统演化关系,提出了新的分类系统。在分支分类中,金松科被选作外类群。主要根据外类群比较原则、化石原则和一般的演化规律,确定了性状的祖征和衍征,采用最大同步法、综合分析法、演化极端结合法及最小平行进化法共四种方法进行分支分析,选择最简约的分支图作为本文讨论基础。在表征分类中,选取59个性状,利用距离系数和类平均法,对金松属和杉科各属进行了聚类运算,得出表征图。综合两种分析结果,主要结论如下:(1)属间关系:柳杉属是现存杉科植物中最原始的类群。水松属和落羽杉属关系密切,二者与柳杉属近缘。巨杉属和北美红杉属关系密切,是中级进化水平的类群。水杉属与巨杉属和北美红杉属的亲缘关系相对较近。杉木属、密叶杉属和台湾杉属关系密切,是杉科植物中的高级进化类群,其中又以台湾杉属演化水平最高。(2)系统排列:支持金松科的成立,将杉科分成5族,即柳杉族(仅含柳杉属)、落羽杉族(含水松属、落羽杉属)、北美红杉族(含巨杉属、北美红杉属)、水杉族(仅含水杉属)和杉木族(含杉木属、密叶杉属及台湾杉属)。     

密叶杉属的核型分析及其系统位置的探讨

本文首次对特产澳大利亚塔斯马尼亚岛的Athrotaxis cupressoides和Athrotaxis selaginoides进行了核型分析,核型公式分别为2n=22=22m(2SAT)和2n=22=20(2SAT)+2sm,均属Stebbins的1B类型,它们的染色体相对长度组成为22=2L+10M₂+8M_l+2S和22=2L十10M₂+6M_l+4S,后者比前者较为进化。根据密叶杉属和杉科其他各属核型资料的比较分析,它们由原始到进步的顺序可能为：柳杉属、水松属、落羽杉属、水杉属、巨杉属、红杉属,密叶杉属、杉木属和台湾杉属。 密叶属与红杉属、巨杉属和杉木属较为近缘。 这些在以染色体长度比和平均臂比为纵、横坐标的图上得到清楚反映。 根据核型资料,密叶杉属以隶于单型的亚科Arthrotaxoideae较为合适,这也得到形态学、胚胎学、孢粉学和地理学资料的支持。 本文还对前人系统中的密叶杉属位置进行了讨论。     

杉科的两条演化路线

本文根据核型资料提出杉科可能存在A、L两条演化路线,前者包括由原始到进化的柳杉属、水 松属、落羽杉属、台湾杉属,以平均臂比快速增加、染色体长度比缓慢增加为特征;后者包括依序进化的水杉属、巨杉属、红杉属、杉木属(可能还有密叶杉属),以平均臂比缓慢增加、染色体长度比迅速增加为特点。该结论也得到形态学、解剖学、胚胎学等资料的支持。     

生境的破坏或改变对杉科种属分布的影响

杉科共有10个属16种,其中5个是单种属(水杉属、水松属、巨杉属、北美红杉属、金松属),5个是寡种属(杉木属、台湾杉属、柳杉属、落羽杉属、密叶杉属),两者各占50%。分布于北温带地区,多在东亚和北美洲,仅密叶杉属分布于南半球澳大利亚的塔斯马尼亚。植物与生境是一个互相依存的统一体,而生境的破坏或改变对杉科植物种属分布有严重的影响。在美国加利福尼亚洲现今仅有巨杉和北美红杉两个单种属,这是由于火山爆发留下来,现在仅分布于美国加州部分地区。     

中国和邻近地区杉科特有植物的核型及其进化水平的初步研究

中国和邻近地区杉科特有植物的核型类型,柳杉属、水松属、水杉属均为“1A”,杉木属、台湾杉属分别为“1B”和“2B”,它们的进化水平似依序递增并组成A-柳杉属——水松属——台湾杉属和L-水杉属——杉木属二条演化路线。该结果得到某些形态学性状和古植物学的支持,基本上适用于整个杉科。     

杉科的染色体资料及在系统演化研究中的作用

杉科共由10属(包括金松属)、20种(变种)组成。本文整理了19种(占95％,隶10属)植物的染色体数目和16种(占80％,隶9属)的核型资料,核型的模式图如图1所示。通过对这些细胞学资料的分析,笔者支持2n=20、x=10的金松属从杉科(2n=22、x=11)分立成金松科。根据其他各属间的亲缘关系,本作者认为可以把它们分隶于5个亚科:Ⅰ.柳杉亚科:Cryptomerioideae(Cryptomeria);Ⅱ.落羽杉亚科Taxodioideae(Glyptostroous,Taxodium);Ⅲ.红杉亚科Sequoideae(Metasequoia,Sequoiadendron,Sequoia);Ⅳ.杉木亚科Cunninghamioideae(Cunninghamia,还可能有:Athrotaxis);Ⅴ.台湾杉亚科Taiwainoideae(Taiwania)。这些亚科和属的进化水平依序渐增,它们分别位于进化路线A(亚科Ⅰ、Ⅱ、Ⅴ)和进化路线L(亚科Ⅲ、Ⅳ)上。这些结果是前人的演化系统所没有涉及的,表明了染色体资料在杉科的系统演化研究中起着重要的作用。     

秃杉的细胞学研究

本文首次报道秃杉的核型为K(2n)=22=16m+6sm, 3号染色体具“长着丝点区 域”。似具比同属的台湾杉(18m+4sm)进化的趋势。它们均为"2B"。从国产杉科植物的 核型类型看,似见"2B"的台湾杉属与"1B"的杉木属和"1A"的水杉属、水松属、柳杉属的亲缘关系依序由近到远并比它们进化。本作者还观察了秃杉的核仁数目和多微核现象。     

从核型看北美红杉的起源

本文分析了同源异源自然六倍体北美红杉的AA和B染色体组的组型,它们属Stebbins的“1A”和“1B”,经与杉科各属植物的核型比较后发现分别与相同类型的水杉和巨杉最为接近,因而认为水杉属和巨杉属的某个古代种可能是北美红杉的二个杂交亲本,水杉和巨杉则或许是它们的后裔或近缘。本研究支持Stebbins认为水杉属的某个古代种是红杉的一个祖先而水杉是它的直接后裔的假设,但与他认为另一个祖先已经灭绝并没有留下近缘的推测存在分歧。     

秃杉的胚胎发育及其与杉科各属的比较

本文报道秃杉(Taiwania flousiana Gaussen)的雌雄配子体和胚胎发育的研究结果及其与 杉科各属的比较。秃杉的大孢子经10次游离核同时分裂,产生1019—1021个游离核。 6月 初游离核开始向心地形成细胞壁。雄配子体具两个大小、形状相同的精子。受精作用在湖北 发生于6月底至7月初(1960)。受精卵经3次游离核分裂,形成8核原胚,排列成两群,紧接 着形成壁。上下2群细胞的数目分配为5：3或4:4,少数为6:2。 从胚胎学的资料来看,秃杉与台湾杉一样,它们最接近杉木属和水松属,与柳杉属、落羽松 属和水杉属也有类似之处。它们的共同特征是：精子形状、大小相同,复合颈卵器顶生,原胚 具8个游离核,兼具裂生多胚。而红杉属、巨杉属、密叶杉属和金松属的胚胎发育各有特点,应分别属于杉科不同的类群。     

Studies on the Structures of Two New Triterpene Saponins C and D from Polygala japoni-ca Houtt

Two new triterpene saponins C and D have been isolated from the aerial parts of Polygala japonica Houtt. Their molecular formulas: C42H68O15 were structural isomers of each other. Acid hydrolysis of the two saponins all produced a sapogenin (2a, 3a, 24-trihydroxyo-lean-12-ene-28-oic acid) and D-glucoses. But only the saponin D could be hydrolyzed in the alkaline solution, the products were identical with those from acid hydrolysis. Their structures have been established by means of 1HNMR,13CNMR and MS as 3-O-[β-D-glucopyranosyl(l→2)β-D-glucopyranosyl] 2α, 3α, 24-trihydroxyolean-12-ene-28-oic acid, 28-O-[β-D-glucopy-ranosyl (1→2)-β-D-glucopyranosyl] 2α, 3α, 24-trihydroxyolean-12-ene-28-oic acid.     

锐尖山香圆叶中三萜类成分的研究

从锐尖山香圆(Turpinia arguta (Lindl.) Seem.)叶中分离得到了11个三萜类化合物。通过光谱分析,分别鉴定其结构为熊果酸(1), 3β,6β,23-trihydroxy-12-oleanen-28-oic acid (2), 3β,6β,23-trihydroxyurs-12-en-28-oic acid (3), 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid (4), 1 α, 3β,23-trihydroxy-12-oleanen-28-oic acid (5), arjunglucoside II (6), rosamultin (7), 3β-O-β-D-glucopyranoylcincholic acid (8), cinchonaglycoside C (9), mussaendoside S (10) 和3β-O-β-D-glucopyranosyl quinovic acid 28-O-β-D-glucopyranosyl ester (11)。除化合物1和6,其它化合物均为首次从山香圆叶中分离得到。     

Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells

Two new compounds, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid (1) and 3α-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] ester (2), and eight known lupane-type triterpenoids (3-10), were isolated from steamed leaves of Acanthopanax koreanum. Chemical structures were determined using a combination of spectroscopic analyses and chemical reactivity. Compounds 1-10 were evaluated for their inhibitory activities on lipopolysaccharide (LPS)-stimulated interleukin (IL)-12 production in bone marrow-derived dendritic cells (BMDCs). Compound 1 exhibited inhibitory activity with IC(50) value of 26.5 μM on IL-12 production, compared with IC(50) value of 29.6 μM for the positive control. Compound 1 also showed significant suppression of LPS-stimulated IL-6 and tumor necrosis factor-alpha (TNF-α) production.     

Study on the Structure of a New Triterpene Saponin B from Polygala japoniea Houtt

A new triterpene saponin B has been isolated from the earial parts of Polygala japonica Houtt in folk-lore medicine. Its molecular: C48H78O20, m.p. 199–202℃, [α]D23+30.0 (C, 0.5, CH3OH). Acidic hydrolysis of this saponin gave a sapogenin (2α, 3α, 24-tri-hydroxyolean-12-ene-28-oic acid) and D-glucose. The structure of saponin B was elucidated as 28-O- [β-D-glucopyranosyl (1→2) -β-D-glucopyranosyl (1→2) -β-D-glucopy- ranosyl] 2α, 3α, 24-trihydroxyolean-12-ene-28-oic acid mainly by 13C-NMR, MS and some chemical transfomations.     

肋果茶中的萜类化学成分研究

从肋果茶(Sladenia celastrifolia)95％乙醇提取物的乙酸乙酯部位中分离得到15个萜类化合物,经波谱学方法分别鉴定为sladeniafolin A(1),grasshopper ketone (2),(3S,5R,6S,7E,9R) -7-megastigmene-3,6,9-triol (3),hedytriol (4),(3S,5R,6R,7E,9R) -3,5,6,9-tetrahydroxy-7-megastigmene(5),1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′-trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien -2-one (6),2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid (7),2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid(8),pomolic acid(9),3-O-acetyl pomolic acid(10),ursaldehyde (11),camarolide (12),3β-hydroxyurs-11-en-13β(28) -olide (13),3β-hydroxy -11α,12α-epoxy-urs-13β,28-olide (14)和28-0-β-D-glucopyranosyl euscaphic acid (15).以上化合物均首次从该植物中分离得到,其中1为新的C9裂环烯醚萜.     

Triterpene saponins from Cyclamen hederifolium

Five triterpene saponins never reported before, hederifoliosides A-E, and four known triterpene saponins were isolated from the tubers of Cyclamen hederifolium. The structures of hederifoliosides A-E were determined as 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-[β-D-glucopyranosyl-(1 → 6)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,30-trihydroxyolean-12-en-28-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,28,30-tetrahydroxyolean-12-en 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including Hela, H-446, HT-29, and U937. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.     

圆果雪胆中的皂甙成分

从圆果雪胆（Ｈｅｍｓｌｅｙａ ａｍａｂｉｌｉｓ）的块茎中分离到１０个化合物,其中３个雪胆皂甙是首次从该种植物中得到,它们的结构通过光谱和化学的方法鉴定为齐墩果酸－３－Ｏ－α－吡喃阿拉伯糖（１→３）－β－葡萄糖醛酸甙,２８－Ｏ－β－Ｄ－吡喃葡萄糖齐墩果酸３－Ｏ－α－吡喃阿拉伯糖（１→３）－β－Ｄ－葡萄糖醛酸,２８－Ｏ－β－Ｄ－吡喃葡萄糖齐墩果酸３－Ｏ－「β－Ｄ－吡喃葡萄糖（１→２）」－「α－吡喃阿     

Triterpenoid saponins from the flower buds of Fatsia japonica

Six triterpenoid saponins isolated from the flower buds of Fatsia japonica were identified as 3-O-[β-D-glucopyranosyl(1 → 4)-α-L-arabinopyranosyl]-oleanolic acid, 3-O-[α-L-arabinopyranosyl]-hederagenin, 3-O-[β-D-glucopyranosyl(1 → 4)-α-L-arabinopyranosyl]-hederagenin, 3-O-[α-L-arabinopyranosyl]-echinocystic acid, 3-O-[α-L-arabinopyranosyl]-16-epiechinocystic acid and 3-O-[α-L-arabinopyranosyl]-oleanolic acid. Of these saponins, three are new.     

Triterpenoidal saponins of Pulsatilla koreana roots

Sixteen (1-16) triterpenoidal saponins were isolated from the roots of Pulsatilla koreana, of which four were determined as the previously unknown 23-hydroxy-3β-[(O-α-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid 28-O-β-D-glucopyranosyl ester (1), 23-hydroxy-3β-[(O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3β-[(O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (3), and 3β-[(O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 4)]-α-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (4), respectively, based on spectroscopic analysis. The inhibition of the lipopolysaccharide-induced nitric oxide production of sixteen isolated compounds was evaluated in RAW 264.7 cells at concentrations ranging from 1 μM to 100 μM.     

Noroleanane saponins from Celmisia petriei

Two biologically active noroleanane saponins from Celmisia petriei are identified as 3-O-(α-l-arabinopyranosyl (1 → 6)-β-d-glucopyranosyl (1 → 2)-α-l-arabinopyranosyl), 2β,17,23-trihydroxy-28-norolean-12-en-16-one and its 2″-O-acetyl derivative. ¹³C NMR and T₁ measurements allowed the determination of the sugar sequence and the majority of the linkage positions, but gave ambiguous results for the inner arabinose sugar. The structure of camellenodiol is revised to 3β,17-dihydroxy-28-norolean-12-en-16-one.