Distribution of Norditerpene Alkaloids in Tall Larkspur Plant Parts Through the Growing Season

Previous research showed that toxic and total alkaloid pools in tall larkspur (Delphinium barbeyi) increased during early growth, then declined precipitously during the late flower and pod stage of growth. The objective of this study was to measure the concentration and pools of toxic and total alkaloids in tall larkspur plant parts, including roots, and to evaluate the changes in these pools over the growing season as an estimate of diterpenoid alkaloid kinetics in tall larkspur. Twenty entire plants were harvested at each phenological stage: beginning of growth in the spring, early flower, early pod, late pod, and senescence. The plants were separated into their respective parts, freeze-dried, extracted, and analyzed for toxic and total alkaloid concentration, and alkaloid pools were calculated. Concentration of toxic and total alkaloids in leaves and stems declined as the plants matured, while concentration in flowers and pods increased (P < 0.004). Concentration of alkaloids in the root declined in the early growth, then increased at the end of the season (P = 0.002). Alkaloid pools in the root decreased during early growth, with a corresponding increase of pools in foliar parts. In the late flower and pod stage, alkaloid pools in the leaves and stems declined rapidly, while the pool in the crown and roots tended to increase.     

拟康定乌头中二萜生物碱成分及拒食活性

[目的]为了研究拟康定乌头中化学成分及其拒食活性.[方法]利用正反相硅胶柱层析进行分离纯化,结合HR-ESIMS、IR、1D和2D NMR等波谱技术对分离得到的化合物结构进行鉴定,采用叶碟法测试了其中10个化合物对甜菜夜蛾3龄幼虫的拒食活性.[结果]共分离得到15个二萜生物碱.其中10个化合物均存在一定的拒食活性.[结...     

高乌头中活性物质的杀虫活性

为了获得高乌头中对3龄粘虫具有较强毒杀作用的活性物质,通过系统分离和活性追踪,分离出活性物质,并通过波谱数据和单晶X-衍射对其进行表征。分离获得了3种具有生物活性的二萜类生物碱,它们分别是去亚甲光飞燕草碱、硬飞燕草碱和来本宁。这3种二萜类生物碱均首次从该植物中分离。     

两个具有新骨架结构的二萜生物碱的质谱研究

利用电子轰击质谱（ＥＩＭＳ）、高分辨质谱（ＨＲＭＳ）和碰撞活化谱（ＣＡＭＳ）等方法研究了两个具有新骨架结构的二萜生物碱的质谱，为其质谱裂解规律性研究提供了依据。     

Krempfielins Q and R,Two New Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi

Two new eunicellin-based diterpenoids, krempfielins Q and R (1 and 2), and one known compound cladieunicellin K (3) have been isolated from a Formosan soft coral Cladiella krempfi. The structures of these two new metabolites were elucidated by extensive spectroscopic analysis. Anti-inflammatory activity of new metabolites to inhibit the superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (FMLP/CB)-induced human neutrophil cells and cytotoxicity of both new compounds toward five cancer cell lines were reported.     

Survival of pine sawflies in cocoon stage in relation to resin acid content of larval food

Several experiments were conducted to determine whether the ingestion of diterpenoids (resin acids) by pine sawfly larvae influences the survival of postlarval stages. Larvae of two diprionid sawfly species were reared on shoots of two Scots pine clones, one with a low (1.5% dry wt) concentration of resin acids and the other with a high (5.2% dry wt) concentration. No significant treatment-related differences were found in any of the experiments with respect to (1) resistance against parasitoids, (2) preference of predatory shrews and carabids, and (3) apparency of cocoons in the field to predators. A preference of sawfly prepupae to spin cocoon in feces from larvae reared on high resin acid needles was found. Possible explanations for these results are discussed. Detection of an unknown compound, possibly a breakdown product of the major resin acid in pine needles (pinifolic acid), in prepupae indicate that resin acids may be metabolized by the sawflies.     

Abietane diterpenoids of Rosmarinus officinalis and their diacylglycerol acyltransferase-inhibitory activity

Inhibition of acyl CoA:diacylglycerol acyltransferase (DGAT) has been proposed as one of the drug targets for treating obesity and type 2 diabetes. Bioassay-guided fractionation of the MeOH-soluble extract of Rosmarinus officinalis yielded two new diacylglycerol acyltransferase (DGAT) inhibitory-abietane diterpenoids, 7β-hydroxy-20-deoxo-rosmaquinone (1) and 7β-methoxy-20-deoxo-rosmanol (2), along with six known components, carnosol (3), 7α-methoxyrosmanol (4), 7β-methoxyrosmanol (5), 12-methoxy-canosic acid (6), rosmanol (7), and rosmadial (8). Compounds 1–8 inhibited DGAT1 activity, with the IC₅₀ values ranging from 39.5 ± 0.6 to 144.2 ± 3.1 μM. In particular, carnosol (3), which is one of the major compounds of MeOH-soluble extract of R. officinalis exhibits inhibition of de novo intracellular triacylglycerol synthesis in human hepatocyte HepG2 cells.     

Two Diterpenoids and a Cyclopenta[c]pyridine Derivative from Roots of Salvia digitaloids

Two new glucosides, salviadigitoside A (1) and salviatalin A-19-O-β-glucoside (2), belonging to the salviatalin type diterpenoids, and a new cyclopenta[c]pyridine, salviadiginine A (3), were isolated from the roots of Salvia digitaloids. Structures of these compounds were determined on the basis of spectroscopic analysis. In addition, compounds 1–3 were evaluated for their anti-inflammatory activity, but the results showed a weak anti-inflammatory activity.     

Diterpene Synthase-Catalyzed Biosynthesis of Distinct Clerodane Stereoisomers

The diterpene synthase clerodienyl diphosphate synthase 1 (PvCPS1) from the crop plant switchgrass (Panicum virgatum) stereoselectively converts (E,E,E)-geranylgeranyl diphosphate (GGPP) into the clerodane natural product, cis-trans-clerodienyl diphosphate (CLPP, 1 ). Structure-guided point mutations of PvCPS1 redirected product stereoselectivity toward the formation of a rare cis-clerodane diastereomer, cis-cis-CLPP ( 2 ). Additionally, an alternative cis-clerodane diastereomer, (5S,8S,9R,10R)-13Z-CLPP ( 3 ), was produced when treating PvCPS1 and select variants thereof with the cis-prenyl substrate (Z,Z,Z)-nerylneryl diphosphate (NNPP). These results support the hypothesis that substrate configuration and minor active-site alterations impact precatalysis substrate folding in the stereoselective biosynthesis of clerodane diterpenoid scaffolds, and can be employed to provide enzymatic access to a broader range of bioactive clerodane natural products.     

Oxygenated Cembranoids from the Soft Coral Sinularia flexibilis

Chemical examination of the Taiwanese soft coral Sinularia flexibilis led to the isolation of five cembrane-based diterpenoids 1–5, including two new metabolites, 11-acetylsinuflexolide (1) and 11-acetyldihydrosinuflexolide (2). The structures of the new metabolites were determined based on extensive spectroscopic analysis, particularly mass spectrometry and 2D NMR (¹H–¹H COSY, HMQC, HMBC, and NOESY) spectroscopy. Metabolites 1, 3 and 4 exhibited moderate to weak cytotoxicity to human tumor cell lines, HeLa, HEp-2, MCF-7 and MDA-MB-231.