狼毒二萜类化学成分及其药理作用研究进展

狼毒Euphorbiae Ebracteolatae Radix为大戟科(Euphorbiaceae)植物狼毒大戟Euphorbia fischeriana或月腺大戟E.ebracteolata的干燥根,是一种广泛应用,具有广阔开发前景的中药材。狼毒含有多种生物活性成分,其中二萜类化合物是最为重要的一个部分,主要包括松香烷型、巴豆烷型、海松烷型、玫瑰烷型、西松烷型、巨大戟烷型、贝壳杉烷型、阿替斯烷型8种类型,此外还有少量二萜二聚体及其他类型的二萜类化合物。狼毒二萜类化学成分具有显著的抗肿瘤、抗炎、抗菌、抗病毒等药理作用。对狼毒二萜类化学成分及其药理作用进行综述,以期为更好地开发狼毒资源及其临床应用提供参考。     

HPLC法测定溪黄草不同部位中5个二萜的含量

目的建立反相高效液相层析(RP-HPLC)法同时测定溪黄草不同部位中5个对映-贝壳杉烷型二萜类延命素[enmein,(1)],黄花香茶菜甲素[sculponeatin A,(2)],诺多星[nodosin,(3)],毛果青茶菜素[isodocarpin,(4)]和毛栲利素[lasiokaurin,(5)]含量的方法,并进行多批次药材成分分析,为溪黄草质量评价提供依据。方法采用Kromasil C18色谱柱(4.6 mm×250 mm,5μm),流动相为甲醇-0.1%甲酸,梯度洗脱,流速0.7 m L·min-1,检测波长254 nm。结果 5个二萜的标准曲线及线性范围依次为:(1)Y=5246.4X+13.86(0.075~1.50μg,r=0.9999);(2)Y=4673.4X+78.09(0.121~2.43μg,r=0.9999);(3)Y=3459.4X+22.33(0.372~7.43μg,r=1);(4)Y=4432.8X+14.71(0.144~2.88μg,r=1);(5)Y=2434.1X+0.69(0.010~1.960μg,r=0.9999)。平均加样回收率为99.14%~100.7%,RSD为0.48%~2.53%。结论经过系统的方法学考察,该法简便,准确,重复性好,可用于溪黄草药材的质量分析及控制。     

Antiprotozoal activity of diterpenoids isolated from Zhumeria majdae- absolute configuration by circular dichroism

PurposeZhumeria majdae, a unique species of the Zhumeria genus, is an endemic Iranian plant in the Lamiaceae family. Phytochemical investigation and biological activity of this plant are rarely reported. The current study aimed to find new antiprotozoal compounds from the roots of Z. majdae and to determine the absolute configuration of isolated compounds by circular dichroism.MethodsThe extraction process from roots and aerial parts of Z. majdae was carried out by hexane, ethyl acetate and methanol followed by testing their antiprotozoal effects against Leishmania donovani, Trypanosoma brucei rhodesiense, T. cruzi, and Plasmodium falciparum, respectively. Structure elucidation was done using 1D and 2D NMR spectroscopy and HREIMS spectrometry. In addition, experimental and theoretical circular dichroism spectroscopy was used to establish absolute configuration.ResultsIn comparison with aerial parts, the hexane extract from roots showed superior activity against T. b. rhodesiense, L. donovani and P. falciparum with IC₅₀ values of 5.4, 1.6 and 2.1 μg/ml, respectively. From eight abietane-type diterpenoids identified in roots, six were reported for the first time in the genus Zhumeria. 11,14-dihydroxy-8,11,13-abietatrien-7-one (6) exhibited a promising biological activity against P. falciparum (IC₅₀ 8.65 μM), with a selectivity index (SI) of 4.6, and lanugon Q (8) showed an IC₅₀ value of 0.13 μM and SI of 15.4 against T. b. rhodesiense.ConclusionAltogether, according to the results, of 8 isolated compounds, dihydroxy-8,11,13-abietatrien-7-one (6) and lanugon Q (8) exhibited a promising activity against T. b. rhodesiense and P. falciparum. In conclusion, these compounds could be potential candidates for further analysis and may serve as lead compounds for the synthesis of antiprotozoal agents. Open in a separate windowGraphical abstractElectronic supplementary materialThe online version of this article (10.1007/s40199-020-00345-w) contains supplementary material, which is available to authorized users.     

Efficacy of phytol-derived diterpenoid immunoadjuvants over alum in shaping the murine host's immune response to Staphylococcus aureus

The ubiquitous gram-positive bacterium Staphylococcus aureus occupies a unique niche in humans for its ability to survive both as a commensal and a life-threatening pathogen. Its complex relationship with the host and its ability to engender a throng of virulence factors, have hindered the development of a successful vaccine against it. The use of immunoadjuvants to enhance host immunity and prevent the shift from commensalism to pathogenicity is a rational approach for containing infection. The objective of this study was to understand the mechanisms by which alum and two phytol-derived immunoadjuvants, phytanol (PHIS-01) ¹ and phytanyl chloride (PCl) ² shape the interaction between S. aureus and its murine host. We studied the effects of the phytol derivatives, relative to alum, on the induction of inflammatory cytokines and chemokines, recruitment of CD11b⁺ cells, generation of specific anti-S. aureus antibodies and in vitro clearance of S. aureus. Our results showed that both PHIS-01 and PCl were stronger inducers of protective cytokines IL-17 and IL-1β than alum, and far exceeded alum in enhancing anti-S. aureus antibody response. However, both alum and the phytol derivatives (particularly PCl) promoted efficient recruitment of CD11b⁺ cells. Furthermore, PHIS-01, alum and to a lesser extent, PCl were able to up-regulate the expression of key inflammation-related genes that were highly down-regulated by S. aureus alone. In vitro killing assays showed that both PHIS-01 and PCl were far more potent than alum in promoting S. aureus clearance; this indicated their efficiency in shaping an effective anti-S. aureus immune microenvironment. In summary, our study provides evidence for the better effectiveness of phytol-derived immunoadjuvants over alum in enhancing anti-S. aureus immunity.     

南方红豆杉枝叶二萜类化学成分的研究

采用硅胶柱色谱以及制备HPLC等柱色谱方法,从南方红豆杉（Taxus wallichiana var. mairei）枝叶氯仿萃取部位分离鉴定了12个紫杉烷类二萜化合物,分别为： 2-deacetoxytaxinine E （1）,2-deacetoxytaxinine J （2）,7-deacetoxytaxinine J （3）,taxinine J （4）,7,2′-didesacetoxyaustrospicatine （5）,N-methyltaxol C （6）,2-deacetoxydecinnamoyl taxinine J （7）,taxol （8）, 7-epi-taxol （9）,7-epi-10-deacetoxytaxol （10）,cephalomannine（11）,7-epi-cephalomannine（12）。其中,化合物1,3为首次从该植物枝叶中分离得到。     

A new labdane-type diterpenoid from Leonurus japonicus

Five fractions prepared from the crude extract of Leonurus japonicus were examined in order to determine their cytotoxic potential. Under the bioassay guidance, a new labdane-type diterpenoid (1), and nine known ones (2–10) along with a seco-labdane (11) were isolated from the aerial parts of Leonurus japonicus. The structure elucidation was primarily based on comprehensive spectroscopic analyses, including HRESIMS, IR, and 1D and 2D NMR methods. Compound 4 (6β-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one) exhibited potential cytotoxicity against HeLa cell line (IC₅₀ = 23.75 μM).     

固相萃取-高效液相色谱法测定拟缺香茶菜中3个二萜类成分的含量

目的建立测定拟缺香茶菜药材中二萜类成分Kamebacetal-A、Kamebacetal-B、肾形香茶菜丙素的方法。方法采用固相萃取-高效液相色谱法(SPE-HPLC)测定3个二萜类成分的含量。使用Venusil C18(4.6 mm×250 mm,5μm)反相色谱柱;流动相:乙腈(A)-水(B)梯度洗脱;流速:1 m L/min;柱温:30℃;检测波长230 nm。结果拟缺香茶菜中Kamebacetal-A、Kamebacetal-B、肾形香茶菜丙素分别在0.056~0.448 g/L(r=0.999 2),0.002 6~0.020 8 g/L(r=0.999 4),0.016~0.128 g/L(r=0.999 7)内与峰面积成良好的线性关系;平均回收率分别为97.53%(RSD=2.16%),96.02%(RSD=2.01%),98.23%(RSD=2.10%)。结论所建立的方法灵敏、准确、稳定,可用于拟缺香茶菜中Kamebacetal-A、Kamebacetal-B、肾形香茶菜丙素的含量测定,为拟缺香茶菜抗肿瘤谱效关系的研究奠定基础。     

香茶菜属植物的研究概况及药用前景展望

本文综述截止到1986年上半年国内外发表的有关香茶菜属植物研究的资料。对本属植物研究的大概趋势进行了概括;进而又在此基础上,对大家所关心的本属植物的药用前景作了一些探讨,并就这个问题提出笔者的几点看法。     

丹参的化学成分

综述了中药丹参化学成分的研究概况,已分离到的化合物表明丹参的主要成分为酚酸类和二萜类。     

巨柏茎叶的萜类成分（英文）

目的：对巨柏（Cupressus gigantea）茎叶的化学成分进行研究。方法：采用硅胶和 Sephadex LH-20 柱色谱的方法分离和纯化化合物, 通过 NMR, MS 及理化性质鉴定化合物结构。结果：从巨柏茎叶分离得到 15 个 labdane-type二萜, 其中一个为新化合物, 分别为：15-methoxy-18-hydroxylabda-8（17）,13-diene （1）, 13-epitoruolsol （2）, labd-8（17）,14-dien-13-ol （3）, 13-epi-cupressic acid （4）, cis-communic acid （5）, trans-communic acid （6）, labd-15-aceoxy-8（17）,13E-dien （7）, labd-8（17）,13E-dien-15-ol （8）, isocupressic acid （9）, acetylisocupressic acid （10）, isoabienol （11）, 13-oxo-14,15-dinor-labd-8（17）-en-19-oic acid （12）, pimarenic acid （13）, sandaracopimaric acid （14）, and pimarol （15） 此外还有两个已知倍半萜 ent-oplopanone （16） 和 （＋）-T-Cadinol （17）。结论：化合物（1）为新的倍半萜, 所有化合物均为首次从该植物中分得。