Aporphinoid alkaloids and other constituents from Lettowianthus stellatus

Two new aporphinoid alkaloids, f1ttowianthine and 11-methoxylettowianthine were isolated from the root bark of Lettowianthus stellatus, together with the new sesquiterpene 11-hydroxyguaia-4,6-diene and the known compounds liriodenine, (Z)-7-octadecen-9-ynoic acid, methyl (2E,6E,10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate, methyl (2E,6E,10R)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate , and 3,4,5-trimethoxyphenol. The structure elucidation was achieved by spectroscopic methods.     

Development of superfluous soldiers induced by juvenile hormone analogues in the termite,Reticulitermes lucifugus santonensis

Summary The synthetic juvenile hormone (JH): 17% alltrans+83%trans, trans, cis-methyl 10-epoxy-3,7,11-trimethyl-2,6 tridecadienoate and juvenile hormone analogues (JHA): methyl 10-chloro-3,7,11-trimethyl-2 dodecenoate and ethyl 10-epoxy-3,7,11-trimethyl-2,6-dodecadienoate administered on filter paper to small groups of the European subterranean termiteReticulitermes lucifugus santonensis Feyt. caused differentiation of larvae and pseudergates into pre-soldiers and/or pseudergate-soldier intercastes. In contrast to the proportion of one soldier to 100–300 other individuals in normal colonies, the effect of the compounds tested that showed JH activity was to induce the development of a large number of superfluous soldiers in quantities that even exceeded the number of other kinds of individuals. Such a disturbance in the caste ratio leads to increased mortality.

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Zusammenfassung Das synthetische Juvenilhormon (JH): 17% alltrans+83%trans, trans, cis-Methyl 10-epoxy-3,7,11-trimethyl-2,6 tridecadienoate und die Juvenilhormonanaloge (JHA): Methyl 10-chloro-3,7,11-trimethyl-2 dodecenoate und Ethyl 10-epoxy-3,7,11-trimethyl-2,6-dodecadienoate, die auf Filterpapier kleinen Termitengruppen der europäischen ErdtermitenartReticulitermes lucifugus santonensis Feyt. zugeführt wurden, verursachten eine Differenzierung von Larven und Pseudergaten in Vorsoldaten und/oder Interkasten Pseudergate-Soldat. Zum Unterschied vom Verhältnis ein Soldat zu 100 bis 300 anderen Individuen in normalen Kolonien erscheint unter der Einwirkung der getesteten juvenilhormonwirksamen Stoffe eine grosse Menge überzähliger Soldaten, deren Anzahl jene der übrigen Individuen sogar übersteigen kann. Die Gleichgewichtstörung zwischen den Kasten hat eine höhere Absterberate der Termiten zur Folge.

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Résumé L'hormone juvénile synthétique: 17% alltrans+83%trans, trans, cis-méthyle 10-epoxy-3,7,11-triméthyle-2,6 tridecadienoate et l'analogue de l'hormone juvénile: méthyle 10-chloro-3,7,11-triméthyle-2 dodecenoate et éthyle 10-epoxy-3,7,11-triméthyle-2,6-dodecadienoate, qui ont été administrés amenés sur papier filtre à de petits groupes de termitesReticulitermes lucifugus santonensis Feyt., ont causé une différenciation de larves et de pseudergates en présoldats et/ou intermédiaires pseudergate-soldat. A la différence du rapport de 1 soldat à 100–300 autres individus dans des colonies normales, on assiste sous l'effet de la substance testée avec effet d'hormone juvénile à l'apparition d'un grand nombre de soldats en surplus, dont le nombre peut même dépasser celui des autres individus. Le trouble de l'équilibre entre les castes conduit à un taux de mortalité supérieur des termites.

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Dedicated to Prof.K. Gösswald at the occasion of his 65th birthday.     

Action of juvenoids on the metamorphosis of cyclorrhaphous Diptera

Administrations of high doses of juvenoids to the last instar larvae of cyclorrhaphous flies cause occasionally lethal defects in puparium formation but mostly affect only the pupal-adult transformation. In pupae, juvenoids impede proliferation and differentiation of the imaginal disks and of abdominal histoblasts: at low doses they cause incomplete rotation of male genitalia and deformations of the ovipositor, at higher doses their effects gradually spread from the tip of abdomen towards the middle of the body. The highest amounts influence the entire abdomen, size and pigmentation of the eyes, and development of hairs and sclerotization of the integument on the head and thorax. Various species slightly differ in the pattern of morphological effects produced, in the ability of affected insects to leave the puparium, and in the sensitivity to juvenoids of different types. A uniform scale for classification of morphological effects in the species examined is described in this paper. The most potent juvenoids are effective at doses around one nanogramme per specimen. Out of 29 selected compounds tested, isopropyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate is the most active juvenoid for Drosophila, Musca, and Sarcophaga; methyl 10,11-epoxy-3,7,11-trimethyl-2,6-tridecadienoate is the most active juvenoid for Ceratilis; and isopropyl 11-chloro-3,7,11-trimethyl-2-dodecenoate possesses the highest activity for Calliphora.     

海洋真菌帚状弯孢聚壳FS26代谢产物的分离鉴定与抗肿瘤活性研究

采用硅胶柱、反相硅胶柱和凝胶柱等色谱技术和重结晶进行分离纯化,从一株分离自南海沉积物的海洋真菌帚状弯孢聚壳Eutypella scoparia的液体发酵提取物中分离得到6个化合物。通过分析波谱数据和与文献比对,化合物1－6分别被鉴定为：(3S,3aR,7aS)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (1),rel-(3S,6S,7R,10R)-7,10-epoxy-3,7,11- trimethyldodec-1-ene-3,6,11-triol (2),euphorbol (3),tuberoside (4),phenochalasin B (5),尿嘧啶(6)。生物活性测试结果显示细胞松弛素类化合物5对MCF-7、NCI-H460和SF-268三种肿瘤细胞株均具有显著的抗肿瘤活性,其IC50分别为0.022μmol/L、0.073μmol/L和0.059μmol/L。     

降香黄檀不同混交林土壤细菌多样性差异分析

为探讨降香黄檀不同混交林土壤细菌的多样性及其与土壤性质的关系,应用高通量测序技术,比较降香黄檀(Dalbergia odorifera T.Chen)分别与奥氏黄檀(Dalbergia oliveri)、大果紫檀(Pterocarpus macarocarpus)、檀香(Santalum album L.)和母生(Homalium hainanense Gagnep.)混交的4种模式土壤细菌多样性,并结合土壤的理化、酶活进行了相关性分析。结果表明,14种混交林土壤的理化、酶活均存在差异。其中降香黄檀与檀香混交林土壤的含水量、有机质、全氮、有效钾和脲酶含量最高,分别为:5.24%、27.5 g/kg、0.85 mg/g、37.46 mg/kg和0.32 mg/kg,降香黄檀与大果紫檀混交林土壤的p H、有效磷和多酚氧化酶含量最高,分别为:4.48、6.04 mg/kg、4.19 mg/kg。2通过高通量测序表明四种混交模式土壤细菌的丰富度为:降香黄檀×檀香降香黄檀×大果紫檀降香黄檀×奥氏黄檀降香黄檀×母生,土壤细菌多样性为:降香黄檀×大果紫檀降香黄檀×奥氏黄檀降香黄檀×檀香降香黄檀×母生。其中,变形菌门、酸杆菌门、放线菌门、绿弯菌门和厚壁菌门为4种混交模式中的主要菌群。3经冗余分析和相关性分析表明,影响降香黄檀混交林土壤细菌群落结构和细菌多样性的主要土壤理化因子为:p H值、脲酶、多酚氧化酶和有机质。     

Acetophenones and terpenoids from Senecio Gallicus

Six new compounds isolated from the aerial part of Senecio gallicus were: 7,11,15-trimethyl-3-methylene hexadecan-1,2-diol diacetate; 7,11,15-trimethyl-3-methylenehexadecan-1,2-diol; 3,5-bis(3-methyl-2-butenyl)-4-acetoxyacetophenone; 3-(2-hydroxy-3-methyl-3-butenyl)-5-(3-methyl-2-butenyl)4-hydroxacetophenone; 3-(2,3-dihydroxy-3-methyl-butyl)-5-(3-methyl-2-butenyl)-4-hydroxyacetophenone and 1,10-epoxy-8α-hydroxy eremophilenolide.     

Monoterpene and lignan glycosides in the leaves of Crataegus pinnatifida

In the present phytochemical study on the leaves of Crataegus pinnatifida, a new monoterpene glycoside, (3S,5R,6R,7E,9R)-3,6-epoxy-7-megastigmen-5,9-diol-9-O-β-Dglucopyranoside(6) and a new sesquilignan glycoside, acernikol-4’’-O-β-D-glucopyranoside (15), together with thirteen known compounds were isolated.     

Critical Sensitivity of the Ovary of <Emphasis Type="Italic">Aedes aegypti</Emphasis> Adults to Sterilization by Juvenile Hormone Mimics

STERILIZATION of adult insects with juvenile hormone mimics has been reported several times^1–5, but only once for adult mosquitoes and no details were given². I report here on the sterilizing effect of three juvenile hormone mimics on female Aedes aegypti. They were (i) mixed geometric isomers of methyl 10,11-epoxy-3,7,11-trimethyl-2,6-tridecadienoate (CJH2), one of two substances with high juvenile hormone activity isolated from Cecropia oil⁶; (ii) mixed geometric isomers of farnesyl methyl ether (FME) and (iii) 2 cis/trans, 6 trans farnesenic acid ethyl ester (FAE). All three compounds were first tested on fifth instar Rhodnius prolixus using Wiggles-worth's method⁷. The doses to give a score of ten were as follows: CJH2 1.3µg; FME 1.4 µg; FAE 31.7 µg.     

降香黄檀土壤微生物数量的时空动态特征

【目的】研究降香黄檀土壤微生物数量在时间和空间上的动态特征,可为降香黄檀栽培技术的完善提供数据支持。【方法】采用稀释平板涂布法,比较分析降香黄檀根际和非根际土壤微生物三大类群(细菌、放线菌、真菌)数量的季节及垂直分布情况。【结果】(1)降香黄檀根际和非根际土壤均表现为春季细菌、真菌数量较多,冬季细菌数量较少,秋季真菌数量较少;非根际土壤放线菌冬季数量较多,秋季数量较少。(2)细菌的根际效应最为明显,其R/S为0.12~62.96;真菌次之,其R/S为0.22~2.46;放线菌的根际效应较小,其R/S为0.32~1.01。(3)降香黄檀上层土(0~20 cm)的微生物数量普遍高于其他土层;随着土层加深,微生物数量表现为逐渐下降或先下降后升高2种变化趋势。【结论】降香黄檀土壤微生物数量的分布受季节和土层的影响。     

Effects of insect growth regulators on the tobacco cutworm, Spodoptera litura: Rectal prolapse

Prolapse of the rectum was observed when ZR-515 (isopropyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate) was applied to the 6th instar larva of the tobacco cutworm, Spodoptera litura. It was induced by an administration of ZR-515 in the middle of the 6th instar larval stage, and either by a dose higher than required for the induction of larval-pupal intermediates or by a dose lower than the dose that produces extra larvae. Larvae with a rectal prolapse appeared only on the 3rd day after treatment. These larvae did not survive for more than 1 to 2 days because the prolapsed rectum ruptured, leading to haemorrhage.Rectal prolapse was also induced by other two IGRs, ZR-512 (ethyl 3,7,11-trimethyl-2,4-dodecadienoate) and ZR-619 (ethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienethiolate).     

Structure,haemolymph titre,and regulatory effects of juvenile homone during ovarian maturation in Leucophaea maderae

Juvenile hormone (JH) synthesized and secreted in vitro by the corpora allata of mated adult Leucophaea maderae females was determined to be JH III (methyl-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate).The haemolymph titre of JH was determined during maturation of the terminal oöcytes in the first reproductive cycle of L. maderae. In virgin females, JH is not detectable in the haemolymph during the first eight days following adult emergence; however, by 10 days after emergence, trace quantities of JH are apparent. Mating stimuli induce a dramatic increase in the concentration of haemolymph JH, with a peak occurring approximately 12 days after mating; thereafter, the JH concentration declines until it has reached an undetectable level 19 days after mating, at the time of chorion deposition.During ovarian maturation, changes in the rates of synthesis of vitellogenin by the fat body and DNA by the ovary correlate closely with the haemolymph titre of JH. However, no such correlation exists between the JH titre and the extensive ovarian protein synthesis that occurs in L. maderae coincident with chorion formation.The effects of JH I and JH III on both vitellogenin synthesis and ovarain DNA synthesis are statistically similar.     

Quality markers based on phytochemical analysis and anti-inflammatory screening: An integrated strategy for the quality control of Dalbergia odorifera by UHPLC-Q-Orbitrap HRMS

BackgroundQuality control, key for the clinical application of traditional Chinese medicines (TCMs), should be connected to the authentication and efficacy of TCMs. The heartwood of Dalbergia odorifera has been widely used to treat inflammation-related diseases. However, in the Chinese pharmacopeia, only the total volatile oil, which does not sufficiently reflect the clinical efficacy, is used as a quality control indicator.PurposeEstablishing a “phytochemical-specificity-effectiveness-Q-marker” analytical strategy to improve the quality control of D. odorifera.MethodsCombined with biosynthetic pathway analysis, phytochemical compositions identified by UHPLC-Q-Orbitrap HRMS were used to build substantial phytochemical groups and further discover specific Q-markers. Then, lipopolysaccharide-stimulated RAW 264.7 cells were used to screen effective anti-inflammatory ingredients. Finally, a UHPLC-HRMS method was developed and validated to quantify the selected Q-markers in D. odorifera samples.ResultsAlong the constructed biosynthetic pathways, 93 phytochemical components were identified in D. odorifera, including 7 chalcones, 13 flavanones, 21 isoflavones, 21 isoflavanones, 3 flavonols, 19 neoflavones, etc. Among them, 31 compounds representing these 6 categories were further evaluated for their anti-inflammatory activities. It revealed that the extract of D. odorifera and nine flavonoids in the noncytotoxic range could alleviated lipopolysaccharide-stimulated inflammation in RAW 264.7 cells by decreasing the production of proinflammatory mediators such as nitric oxide and interleukin-6. Notably, neoflavones, as species-specific components, exhibited superior anti-inflammatory activities among the representative compounds. Finally, 12 Q-markers (butin, liquiritigenin, eriodictyol, melanettin, naringenin, butein, genistein, 4′-hydroxy-4-methoxydalbergione, isoliquiritigenin, 2,4-dihydroxy-5-methoxybenzophenone, medicarpin, and pinocembrin), which reflect specificity and effectiveness, were successfully quantified in 10 batches of samples from different origins. The origins and consistency of D. odorifera could be efficiently discriminated by hierarchical cluster analysis (HCA).ConclusionThe analysis strategy that combines phytochemical analysis with anti-inflammatory screening clarified the therapeutic material basis and discovered Q-markers, which possibly offers a more comprehensive quality assessment of D. odorifera.     

The fatty acid and sterol composition of two marine dinoflagellates

The fatty acid, sterol and chlorophyll pigment compositions of the marine dinoflagellates Gymnodinium wilczeki and Prorocentrum cordatum are reported. The fatty acids of both algae show a typical dinoflagellate distribution pattern with a predominance of C₁₈, C₂₀ and C₂₂ unsaturated components. The acid 18:5ω3 is present at high concentration in these two dinoflagellates. G. wilczeki contains a high proportion (93.4%) of 4-methyl-5α-stanols including 4,23,24-trimethyl-5α-cholest-22E-en-3β-ol (dinosterol), dinostanol and 4,23,24-trimethyl-5α-cholest-7-en-3β-ol reported for the first time in dinoflagellates. The role of this sterol in the biosynthesis of 5α-stanols in dinoflagellates is discussed. P. cordatum contains high concentrations of a number of δ ²⁴⁽²⁸⁾-sterols with dinosterol, 24-methylcholesta-5,24(28)-dien-3β-ol, 23,24-dimethylcholesta-5,22E-dien-3β-ol, 4,24-dimethyl-5α-cholest-24(28)-en-3β-ol and a sterol identified as either 4,23,24-trimethyl- or 4-methyl-24-ethyl-5α-cholest-24(28)-en-3β-ol present as the five major components. The role of marine dinoflagellates in the input of both 4-methyl- and 4-desmethyl-5α-stanols to marine sediments is discussed.     

Acyclic diterpenes from Croton kerrii

Croton kerrii; Euphorbiaceae; acyclic diterpenes; anti-reserpine ulcer; (E,E,Z)-11- hydroxymethyl-3,7,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol; (E,E,E)-11-formyl-3,7,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol.     

Dinoflagellate sterols IV: Isolation and structure of 4α,23ξ,24ξ-trimethylcholestanol from the dinoflagellate Glenodiniumhallii

The dinoflagellate $\text{Glenodinium}$$\text{hallii}$ was investigated for its sterol composition. Five of the six sterols were isolated and identified as cholest-5-en-3β-ol, (24ξ)-24-methylcholest-5-en-3β-ol, stigmasta-5,22-dien-3β-ol, (22E,24R)-4α,23,24-trimethyl-5α-cholest-22-en-3β-ol, and 4α,23ξ,24ξ-trimethyl-5α-cholestan-3β-ol.     

Phenolic compounds from Dalbergia odorifera

Six new phenolic compounds (1–6), along with five known phenolics (7–11) were isolated from the heartwood of Dalbergia odorifera T. Chen. (Leguminosae). Their structures were determined by spectroscopic techniques including MS, UV, IR, 1D and 2D NMR. Bioassay results showed that compound 1 exhibited cytotoxicity against SGC-7901 and BEL-7402 tumor cell lines, while compounds 3, 5 and 10 showed antibacterial activities against Ralstonia solanacearum.     

Reduced perylenequinone derivatives from an endophytic Alternaria sp. isolated from Pinus ponderosa

The consecutive solvent extraction of endophytic Alternaria sp. (DC401) isolated from Pinus ponderosa followed by chromatographic techniques led to the isolation of five perylenequinone compounds and one dihydronaphthaquinone derivative, which include three new perylenequinones (1–3). The compounds were identified as 6-methoxy-3,6a,7,10-tetrahydroxy-4,9-dioxo-4,5,6,6a,6b,7,8,9-octahydroperylene (1), 3,6a,9,10-tetrahydroxy-7,8-epoxy-4-oxo-4,5,6,6a,6b,7,8,9-octahydroperylene (2), 6-methoxy-3,6a,9,10-tetrahydroxy-7,8-epoxy-4-oxo-4,5,6,6a,6b,7,8,9-octahydroperylene (3), 3,6a,7,10-tetrahydroxy-4,9-dioxo-4,5,6,6a,6b,7,8,9-octahydroperylene (altertoxin I) (4), 3,6a,7,10-tetrahydroxy-4,9-dioxo-4,6a,6b,7,8,9-hexahydroperylene (dehydroaltertoxin I) (5), and 7-chloroscytalone (6). Structure of compounds 1–6 was determined on the basis of detailed spectroscopic analysis, as well as by comparison with literature reports. The antileismanial, antimicrobial, antimalarial and in vitro cytotoxic activities of compounds 1–6 were evaluated.     

海南省降香黄檀害虫种类、分布及危害症状调查

【背景】降香黄檀被确定为海南省省树后,种植面积迅速增大,但对于其病虫害的监测与防控方面的研究较少。【方法】采用人工采集结合灯光诱集的方法,调查降香黄檀种植区的害虫种类,同时对其危害症状进行了详细描述。【结果】海南降香黄檀害虫共计19种,确定了其中18种的学名,并掌握了各害虫的分类学地位、危害部位及症状。害虫在降香黄檀植株各个组织部位均有分布,其中以叶部的分布数量较大,茎干次之。苗期以食叶性害虫居多;5年生以内的植株上蛀干害虫数量显著增多;老龄植株上的茎干害虫较少。【结论与意义】海南省降香黄檀各生育期均有害虫危害,日后仍需加强对其害虫监测与防控技术的研究。     

Triterpenes of Lithocarpus species

The triterpenes of the five Lithocarpus species examined comprised members of the friedo- and unrearranged oleanane groups, viz. friedelin, friedelan-3β-ol, taraxerol and β-amyrin. Glutinol was also present, except in L. harlandi where friedelan-2α,3β-diol was found. In addition, three new cycloartane triterpenes, lithocarpolone (21,24-epoxy-24-hydroxymethyl-cycloartan-3-one), lithocarpdiol (21,24-epoxy-24-hydroxymethyl-cycloartan-3β-ol). and 24-methylenecycloartan-3β,21-diol were found in L. polystachya, and their structures determined.     

Triterpenes from Douglas fir sapwood

The saponified ether-soluble extractives of Douglas fir sapwood contained (24R)- 4α,14α,24-trimethyl-9β,19-cyclo-5α-cholestan-3β-ol(24R-cyclocucalanol),a new natural product; 4α,14α-dimethyl-9β,19-cyclo-24-methylene-5α-cholestan-3β- ol (cycloeucalenol); and (24R)-4α,24-dimethyl-5α-cholest-7-en-3β-ol (24R- methyllophenol); this is the first time they have been reported from Douglas fir.