Research progress on the role of cytochrome P450 in plant sesquiterpene biosynthesis / 药学学报

Sesquiterpenes are natural terpenoids with 15 carbon atoms in the basic skeleton, which mainly exist in plant volatile oil and have important physiological and medicinal value. Cytochrome P450 (CYP450) is a kind of monooxygenase encoded by supergene family, which is one of the largest gene families in plants. It is involved in the synthesis and metabolism of terpenoids, alkaloids and other secondary metabolites. In the process of terpene biosynthesis, CYP450 participates in the post-modification stage of terpenes by introducing functional groups such as hydroxyl, carboxyl and carbonyl, which plays an important role in enriching the diversity of terpenes. The CYP450 enzymes involved in sesquiterpene synthesis and their substrate catalytic specificity mechanisms have been partially investigated. In this paper, the biosynthetic pathway of plant sesquiterpenes, the structure and classification of CYP450 enzymes were briefly introduced, and the CYP450 enzymes involved in sesquiterpene biosynthesis were summarized, in order to provide a reference for intensive study of the role of CYP450 enzymes in the synthesis of sesquiterpenoids.

Chemical composition and pharmacological activity of seco-prezizaane-type sesquiterpenes / 中草药·英文版

The seco-prezizaane-type sesquiterpenes (SPS), as a special class of sesquiterpenes with a highly oxidative five-ring cage structure and seven consecutive chiral centers, are isolated from the genus Illicium, which have a variety of biological activities, including neurotoxicity and neurotrophic effects, etc. This review summarizes the chemical constituents and pharmacological effects of SPS, and discusses the potential trend and scope of future research.

Chemical constituents in Dolomiaea plants and their pharmacological activities: a review / 中国中药杂志

Dolomiaea plants are perennial herbs in the Asteraceae family with a long medicinal history. They are rich in chemical constituents, mainly including sesquiterpenes, phenylpropanoids, triterpenes, and steroids. The extracts and chemical constituents of Dolomiaea plants have various pharmacological effects, such as anti-inflammatory, antibacterial, antitumor, anti-gastric ulcer, hepatoprotective and choleretic effects. However, there are few reports on Dolomiaea plants. This study systematically reviewed the research progress on the chemical constituents and pharmacological effects of Dolomiaea plants to provide references for the further development and research of Dolomiaea plants.

Three new sesquiterpenes from roots of Curcuma longa / 中草药·英文版

OBJECTIVE@#To study the chemical constituents from the roots of Curcuma longa.@*METHODS@#The structures of the compounds were elucidated based on extensive spectral analysis, including 1D and 2D NMR, MS, UV, and CD analysis.@*RESULTS@#Two new sesquiterpene compounds (1S,2R,5R,7S,8R)-2,8-epoxy-5-hydroxybisabola-3,10-dioen-9-one ( 1), (1R,2R,5R,7S,8R)-2,8-epoxy-5-hydroxybisabola-3,10-dioen-9-one ( 2), and a new natural product 6-(4-Hydroxymethylphenyl)-2-methyl-hept-2-ene-4-one ( 3) together with three known compounds ar-turmerone ( 4), 2-methyl-6-(4-hydroxyphenyl-3-methyl)-2-hepten-4-one ( 5) and 2-methyl-6-(4-hydroxyphenyl)-2-hepten-4-one ( 6) were isolated from C. longa root extract with 95% ethanol.@*CONCLUSION@#In the study, three new compounds were isolated from C. longa, and their absolute configurations were determined.

Comparative study of the oil repellent activity of Copaifera officinalis Linnaeus and Copaifera reticulata Ducke front nymphs of Periplaneta americana Linnaeus

Abstract To control urban pests, especially cockroaches of the Periplaneta americana species, various pesticides have been developed that are increasingly potent and effective. However, the unrestrained application of pesticides has had negative consequences, such as the disappearance of some useful insect species and, consequently, the appearance of new pests, both in the countryside and cities. Due to the current scenario, it was necessary to search for new alternatives for the control of these insects. Among the species studied, Copaíba stood out. The oils were analyzed using GC-MS, b-caryophyllene and a-bergamotene being the predominant compounds. Repellency tests were performed with three different concentrations of C. officinalis and C. reticulata, 500 μg/mL, 250 μg/mL and 125 μg/mL, in triplicate. It can be observed that the oil of C. officinalis was more repellent to the nymphs at concentrations of 500 μg/mL and 250 μg/mL, however, when the behavior in nymphs exposed to the concentration of 125 μg/mL was compared, it was noted that C. reticulata oil was more repellent at this concentration. Copaifera has shown promising activity as a repellent against arthropods owing to the complex chemical composition of its oils.

A new allo-aromadendrane sesquiterpene from Dendrobium nobile / 中国中药杂志

To study the chemical constituents in the non-alkaloid part of stems of Dendrobium nobile. The macroporous adsorption resin, MCI, silica gel, RP-C_(18), and Sephadex LH-20 gel, preparative thin layer chromatography, and preparative high-performance liquid chromatography(HPLC) were used to isolate and purify the compounds. The structures of the compound were determined according to the spectra data, physicochemical properties, and relevant references. A total of 8 compounds were isolated from D. nobile, which were soltorvum F(1), p-hydroxyphenylpropionic acid(2), vanillic acid(3), p-hydroxybenzoic acid(4), N-trans-cinnamic acid acyl-p-hydroxybenzene ethylamine(5),(+)-(1R,2S,3R,4S,5R,6S,9R)-2,11,12-trihydroxypicrotoxane-3(15)-lactone(6), dendronobilin H(7), soltorvum E(8). Compound 1 was a novel compound, named as soltorvum F. Compound 8 was isolated from Dendrobium species for the first time.

Research progress on chemical constituents and pharmacological activities of halogenated sesquiterpenes from natural sources / 中国中药杂志

Halogenated sesquiterpenes are important derivatives of sesquiterpenes, referring to chemical components of sesquiterpenes that contain halogens such as chlorine, bromine, and iodine. Halogenated sesquiterpenes have attracted attention from researchers in China and abroad because of their diverse structures, unique halogen elements, and extensive pharmacological activities. Studies have shown that halogenated sesquiterpenes exhibit significant antimicrobial, anti-inflammatory, anticancer, insecticidal, hypoglycemic, and enzyme inhibitory activities. In order to better explore the potential pharmaceutical value of halogenated sesquiterpenes, this paper reviewed the structural characteristics and pharmacological activities of halogenated sesquiterpenes in the past two decades, aiming to provide references for further research and development of this class of compounds.

Avaliação da composição química de um óleo de copaíba (Copaifera spp) e seu efeito em células-tronco mesenquimais / Evaluation of the chemical composition of a copaiba oil (Copaifera spp) and its effect on mesenchymal stem cells

A oleorresina obtida de copaíferas é amplamente utilizada na medicina tradicional brasileira. Este estudo avaliou a composição química por Cromatografia Gasosa (CG) e o efeito da oleorresina de Copaifera officinalis em células-tronco. Para isso as células foram tratadas com a oleorresina nas concentrações de 0,5, 20, 110, 140, 170 ou 200 µg/ml por 24h. A avaliação por CG identificou os sesquiterpenos ß-cariofileno, trans-α-bergamoteno e óxido de cariofileno II como os compostos majoritários da oleorresina. As menores concentrações de oleorresina utilizadas apresentaram resultados semelhantes ao grupo controle e as maiores concentrações diminuíram significativamente a viabilidade celular e apresentaram maior citotoxicidade. Como conclusão, os principais componentes encontrados na oleorresina de copaíba foram os sesquiterpenos e as baixas concentrações testadas não foram citotóxicas. O aumento das concentrações de oleorresina de copaíba promoveu diminuição da viabilidade celular e aumento dos efeitos citotóxicos nas células-tronco. Embora a oleorresina de copaíba tenha uso etnofarmacológico na cicatrização, este estudo demonstrou efeito citotóxico em células-tronco, as quais estão relacionadas ao processo de regeneração corpóreo. Portanto, deve-se ter cuidado com a dosagem de oleorresina a ser utilizada, uma vez que este estudo in vitro mostrou citotoxicidade e um impacto negativo na viabilidade das células-tronco nas mais altas concentrações testadas. [au]

Oleoresinobtained from Copaifera trees is extensively used in Brazilian traditional medicine. This study hasevaluated the chemical composition and effect of Copaifera officinalisoleoresin on stem cells. The oleoresin was analyzed by Gas Chromatography (GC) and the cells were treated with the oleoresin at concentrations of 0.5, 20, 110, 140, 170 or 200 µg/ml for 24h for cellular tests. GC identified the sesquiterpenes beta-caryophyllene, trans-alpha-bergamotene, and caryophyllene oxide II as the main compounds in oleoresin. The cell viability and cytotoxicity assays showed the lowest concentrations of oleoresin used presented similar results to the control group and the higher concentrations tested significantly decreased cell viability and increased cytotoxicity. In a conclusion, the main components found in copaiba oleoresin were sesquiterpenes and the low tested concentrations were not cytotoxic. The increased concentrations of copaiba oleoresin promoted a decrease in cell viability and an increase of cytotoxicity in the stem cells. Although copaiba oleoresin has ethnopharmacology use in healing, this study showed toxicity in stem cells, which are related to the corporeal regeneration process. Therefore, caution must be taken with the dosage of the oleoresin to be used since this in vitro study showed cytotoxicity and a negative impact on stem cell viability at the higher tested concentrations. [au]

Research on Biosynthesis of Anticancer Drug Elemene and Key Enzyme Germacrane A Synthase / 中国生物化学与分子生物学报

Elemene is one of the anti-tumor drugs with independent intellectual property rights in China. It has the advantages of strong anti-tumor activity, wide range of action, mild side effects, and resistance to drug resistance, so it is widely used in the clinical treatment of various malignant tumors. The production of elemene mainly relies on the separation and extraction of the medicinal plant Curcuma wenyujin Y. H. Chen & C. Ling. However, the low content of elemene in the natural materials, complex extracting-process, low product-yield, and high cost, that seriously hinder the large-scale production and the application of elemene. With the development of synthetic biology, constructing cell factories to biosynthesize natural medicines has become a research hotspot, which also provides a new approach for the production of elemene. In recent years, the research on the biosynthesis of elemene has continued to deepen. Researchers have tried to clarify the biosynthesis pathway and key enzymes of elemene by means of metabolic engineering, combinatorial biology, genetic engineering. Some key enzyme genes in the biosynthetic pathway of elemene have been successfully cloned, and the heterologous biosynthesis of elemene has been preliminarily realized. This paper summarizes the elemene biosynthesis pathway and the optimization of engineered bacteria with a review of synthetic biology research thinking, and focuses on the key enzyme gemacrane A synthase (GAS). The optimization strategy of elemene biosynthesis is described, including the overexpression of key rate-limiting enzyme genes, the knockout of shunt genes, the enzymes engineering strategy of fusion expression, and in vitro evolution of key enzyme germacrane A synthetase. The problems and challenges faced in improving the yield of elemene in heterologous biosynthesis were also analyzed. The review will provide a reference for the efficient biosynthesis of elemene.

Tetradenia riparia leaves, flower buds, and stem essential oils to control of Aedes aegypti larvae

Abstract Tetradenia riparia (Hochst.) Codd (Lamiaceae) is a species native to the African continent and used as an insect repellent. The objective of the study was to evaluate the larvicidal potential of essential oils (EOs) from the leaves, flower buds, and stem of T. riparia, collected in winter against Aedes aegypti larvae. The EOs were extracted by hydrodistillation (3 h) and identified by GC/MS. The EOs were tested against larvae of A. aegypti at concentrations ranging from 12500 to 1.5 µg/mL for 24 h. The insecticide activity was evaluated by probit analysis, and the anticholinesterase activity was determined by bioautographic method. The results of the class projection indicated sesquiterpenes as the majority class, corresponding to 60.66% (leaves), 64.70% (flower buds) and 83.99% (stem), and the bioassays on A. aegypti larvae indicated LC50 of 1590, 675 and 665 µg/mL, respectively. The anticholinesterase activity indicated that the EO of the leaves inhibited the enzyme at a concentration of 780 µg/mL, and those from the flower buds and stem inhibited up to 1560 µg/mL. The results indicated weak activity of essential oils against A. aegypti larvae.

Metabolitos bioactivos y actividad antioxidante in vitro del aceite esencial extraído de dos especies del género Tagetes

Objetivo: este estudio investigó los metabolitos bioactivos y actividad antioxidante de aceites esenciales de dos especies del género Tagetes. Método: el aceite esencial se obtuvo por arrastre a vapor de agua, posteriormente se determinó su rendimiento de extracción, densidad relativa, índice de refracción y su solubilidad en etanol (70 % v/v). La composición química fue evaluada mediante cromatografía de gases acoplada a espectrometría de masas (GC-MS). La actividad antioxidante fue determinada mediante el método del radical libre 2,2-difenil-1-picrilhidracilo (DPPH) y la capacidad de atrapamiento del catión radical ABTS*+. Resultados: en los aceites esenciales de las especies Tagetes se logró identificar 26 componentes químicos para la especie Tagetes elliptica Sm. y 16 para Tagetes minuta L., ambas especies presentaron como componentes principales a los monoterpenos (61 %) y sesquiterpenos (44 %). Los metabolitos bioactivos de aceites esenciales entre ambas especies de Tagetes fueron, (3-trans-ocimeno (25,03 %), transtagetona (51,37 %), ß-mirceno (2,78) y ß-cariofileno (1,17 %). Los rendimientos de extracción oscilaron entre 0,05 y 0,048 %, la densidad entre 0,90 y 0,88 (g/ml) con un índice de refracción de 1,493 y 1,482 y una solubilidad (v/v) positiva entre ambas especies. La actividad antioxidante del aceite esencial en ambas especies mostró una variación entre 1,77 y 2,56 mg/mL para el DPPH y 21,02 a 41,06 mg/mL para BTS*+. Conclusión: los aceites esenciales de las especies Tagetes elliptica Sm. y Tagetes minuta L. son una fuente de metabolitos bioactivos fomentan potencialidades antimicrobianas y antioxidantes con fines de su uso como conservantes alimentarios.

SUMMARY Aim: This study investigated the bioactive metabolites and antioxidant activity of essential oils of two species of the genus Tagetes. Method: The essential oil was obtained by steam stripping, its extraction performance, relative density, refractive index and its solubility in ethanol (70 % v/v) were subsequently determined. The chemical composition was tested using gas chromatography coupled to mass spectrometry (GC-MS). The antioxidant activity was determined using the 2,2-diphenyl-1-picrylhydracil (DPPH) free radical method and the ABTS*+ radical cation trapping capacity. Results: In the essential oils of the Tagetes species, it was found to identify 26 chemical components for the species Tagetes elliptica Sm. And 16 for Tagetes minuta L., both species presented monoterpenes (61 %) and sesquiterpenes (44 %) as main components. The bioactive metabolites of essential oils between both species of Tagetes were, (-trans-ocimeno (25.03 %), trans-tagetone (51.37 %), ß-myrcene (2.78) and ß-caryophyllene (1.17 %). The extraction yields ranged between 0.05 and 0.048 %, the density between 0.90 and 0.88 (g/ml) with a refractive index of 1.493 and 1.482 and a positive solubility (v/v) between both species. The antioxidant activity of the essential oil in both species showed a variation between 1.77 and 2.56 mg/mL for DPPH and 21.02 to 41.06 mg/mL for BTS*+. Conclusion: The essential oils of the species Tagetes elliptica Sm. and Tagetes minuta L. are a source of bioactive metabolites that promote antimicrobial and anti-oxidant potentialities for use as food preservatives.

Objetivo: este estudo investigou os metabólitos bioativos e a atividade antioxidante de óleos essenciais de duas espécies do gênero Tagetes. Método: o óleo essencial foi obtido por decapagem a vapor, posteriormente foram determinados seu desempenho de extração, densidade relativa, índice de refração e sua solubilidade em etanol (70% v/v). A composição química foi trabalhada por cromatografía gasosa acoplada a espectrometría de massas (GC-MS). A atividade antioxidante foi determinada pelo método do radical livre 2,2-difenil-1-picrilidracila (DPPH) e pela capacidade de captura do cátion radical ABTS* +. Resultados: nos óleos essenciais das espécies Tagetes, identificou-se 26 componentes químicos para a espécie Tagetes elliptica Sm. E 16 para Tagetes minuta L., ambas as espécies apresentaram monoterpenos (61%) e sesquiterpenos (44%) como principais componentes. Os metabólitos bioativos dos óleos essenciais entre as duas espécies de Tagetes foram, (3-trans-ocimeno (25,03%), transtagetona (51,37%), ß-mirceno (2,78) e ß-cariofileno (1,17%). Os rendimentos de extração variaram entre 0,05 e 0,048%, a densidade entre 0,90 e 0,88 (g/ml) com índice de refração de 1,493 e 1,482 e solubilidade positiva (v/v) entre as duas espécies. A atividade antioxidante do óleo essencial em ambas as espécies apresentou variação entre 1,77 e 2,56 mg/mL para DPPH e 21,02 a 41,06 mg/mL para BTS* +. Conclusão: os óleos essenciais das espécies Tagetes elliptica Sm. e Tagetes minuta L. são uma fonte de metabólitos bioativos, atualmente com potencial antimicrobiano e antioxidante com a finalidade de serem conservantes de alimentos.

Phytochemistry and biological properties of Drimys winteri JR et G. Forster var chilensis (DC) A / Fitoquímica y propiedades biológicas de Drimys winteri JR et G. Forster var chilensis (DC) A

Drimys winteri JR et G. Forster var chilensis (DC) A. is a tree native to central and southern Chile. Also it found in part of Argentina. It is abundant in wet swampy localities from sea level to an altitude of 1700 m. This tree is sacred for the Mapuche culture; it is used in folk medicine in such as inflammatory and painful processes. Phytochemical studies have demonstrated that this plant contains mainly sesquiterpenes of the drimane type, flavonoids, essential oils, phytosterols and some lignans. These drimanes have attracted interest because of their antifeedant, plant growth regulation, cytotoxic, antimicrobial and insecticidal properties. The objective of this review is to establish clearly the phytochemistry and biological activity of Drimys winteri JR et G. Forster var chilensis (DC) A. Articles based on other varieties are not considered.

Drimys winteri JR et G. Forster var chilensis (DC) A. es un árbol nativo del centro y sur de Chile. También se encuentra en parte de Argentina. Es abundante en localidades pantanosas y húmedas desde el nivel del mar hasta una altitud de 1700 m. Este árbol es sagrado para la cultura mapuche. Se utiliza en la medicina popular para tratar enfermedades como procesos inflamatorios y dolorosos. Los estudios fitoquímicos han demostrado que esta planta contiene principalmente sesquiterpenos del tipo drimano, flavonoides, aceites esenciales, fitoesteroles y algunos lignanos. Estos drimanos han despertado interés debido a sus propiedades antialimentarias, regulación del crecimiento de las plantas, propiedades citotóxicas, antimicrobianas e insecticidas. El objetivo de este examen es establecer claramente la fitoquímica y la actividad biológica de Drimys winteri JR et G. Forster var chilensis (DC) A. No se consideran los artículos basados en otras variedades D. winteri var winteri.

Chemical composition and insecticidal activity of Garcinia gardneriana (Planchon & Triana) Zappi (Clusiaceae) essential oil / Composición química y actividad insecticida del aceite esencial de Garcinia gardneriana (Planchon & Triana) Zappi (Clusiaceae)

The present study aimed to analyze the chemical composition of the essential oil from Garcinia gardneriana (Planchon & Triana) Zappi leaves and fruits, and to determine its acaricidal activity on Rhipicephalus microplusy larval packet test and larvicidal action on Aedes aegyptiby larval immersion test. The chemical analysis of the essential oil by gas chromatography-mass spectrometry identified sesquiterpene hydrocarbons and oxygenated sesquiterpenes in bacupari leaves and fruits, and α-cedrene, α-chamigrene, α-trans-bergamotene, and ß-curcumene as major compounds. Essential oil from leaves of G. gardneriana presented acaricidal activity on R. microplus (LC50= 4.8 mg/mL; LC99= 10.8 mg/mL) and larvicidal effect on A. aegypti (LC50= 5.4 mg/mL; LC99 = 11.6 mg/mL), where as essential oil from the fruits of G. gardneriana showed LC50= 4.6 mg/mL and LC99= 8.9 mg/mL against R. microplus and LC50= 6.4 mg/mL and LC99= 13.9 mg/mL against A. aegypti. These results thus demonstrate the potential acaricidal and larvicidal activity of essential oil of G. gardneriana, offering new perspectives for the realization of bioassays from this essential oil.

El presente estudio tuvo como objetivo analizar la composición química del aceite esencial de las hojas y frutos de Garcinia gardneriana (Planchon & Triana) Zappi, y determinar su actividad acaricida en Rhipicephalus microplus y larvicida en Aedes aegypti empleando la prueba de inmersión de larvas. El análisis químico del aceite esencial por cromatografía de gases-espectrometría de masas identificó hidrocarburos sesquiterpénicos y sesquiterpenos oxigenados en hojas y frutos de bacupari, y α-cedreno, α-chamigreno, α-trans-bergamoteno y ß-curcumeno como compuestos principales. El aceite esencial obtenido de las hojas de G. gardneriana presentó actividad acaricida en la garrapata del ganado (LC50= 4,8 mg/mL; LC99= 10,8 mg/mL) y actividad larvicida en A. aegypti (LC50= 5,4 mg/mL; LC99= 11,6 mg/mL), así como, el aceite esencial obtenido de los frutos de G. gardneriana mostró LC50= 4,6 mg/mL y LC99= 8,9 mg/mL contra las larvas de garrapatas de ganado y LC50= 6,4 mg/mL y LC99= 13,9 mg/mL en las larvas de A. aegypti. Por lo tanto, estos resultados demuestran la actividad acaricida y larvicida del aceite essencial de G. gardneriana, ofreciendo nuevas perspectivas para la realización de bioensayos a partir de este aceite esencial.

Chemical constituents of sesquiterpenes from Chloranthus multistachys / 中国中药杂志

With repeated silica gel, octadecyl silica(ODS), and Sephadex LH-20 column chromatography, normal-phase and reverse-phase high performance liquid chromatography(HPLC), etc., a pair of new enantiomers and 5 known compounds were separated from the 95% ethanol extract of Chloranthus multistachys. These compounds were identified by the nuclear magnetic resonance spectroscopy(including 1 D-NMR and 2 D-NMR), single-crystal X-ray diffraction, circular dichroism(CD) spectroscopy, mass spectrometry(MS), and some other methods as(1R,4R,5R,8S,10R)-chloraeudolide H(1 a),(1S,4S,5S,8R,10S)-chloraeudolide H(1 b), hydroxyisogermafurenolide(2), 4α-hydroxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide(3), chloraniolide A(4), chlorantene D(5), 4α,8β-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide(6). Compounds 1 a and 1 b are a pair of new eudesmane-type sesquiterpene enantiomers, and compounds 2-4 were isolated from C. multistachys for the first time.

Advances in biosynthesis of cadinane sesquiterpenes / 生物工程学报

Cadinanes are a class of bicyclic sesquiterpenes with complex stereochemistry and broad pharmacological activities, such as antibacterial, anti-inflammatory, and hypoglycemic activities. To date, structurally diverse and bioactive cadinane sesquiterpenes have been isolated and identified from a variety of plants and microorganisms. Moreover, deeper understandings on cadinane sesquiterpene synthases have been made. This article categorized the 124 new cadinanes which were published in the literatures in the past four years (2017-2020) into five structural types, and presented their pharmacological activities. We also illustrated the elucidation of the biosynthetic pathways for typical cadinanes, summarized the research progress on cadinane sesquiterpene synthases. Finally, current challenges and future prospects were proposed and discussed.

Chemical constituents from Morinda citrifolia and their inhibitory activities on proliferation of synoviocytes in vitro / 中国中药杂志

The chemical constituents from the stems and leaves of Morinda citrifolia were isolated and purified by column chromatography methods with silica gel, ODS, Sephadex LH-20 and preparative high performance liquid chromatography(HPLC). The structures of the isolated compounds were identified by physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in literature. 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of M. citrifolia, and were identified as 9,10-dihydroxy-4, 7-megastigmadien-3-one(1), 5,12-epoxy-6,9-hydroxy-7-megastigmen-3-one(2), fukinone(3), β-eudesmol(4), sarmentol F(5), 4, 5-dihydroblumenol A(6), 3-hydroxy-β-ionone(7), aristol-8-en-1-one(8), ergosta-7-en-3β-ol(9), ergosta-7-ene-3β,5α,6β-triol(10),(22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol(11), olivil(12), 4-epi-larreatricin(13), chushizisin Ⅰ(14), rabdosia acid A(15), glycerol monolinoleate(16) and(9Z,12Z,15Z)-2,3-dihydroxypropyl octadeca-trienoate(17). All compounds were isolated from M. citrifolia for the first time. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their inhibitory activities on the proliferation of synoviocytes in vitro using MTS met-hod. Compounds 1-11 showed significant anti-rheumatoid arthritis activities, displaying the inhibitory effects on the proliferation of MH7 A synovial fibroblast cell with the IC_(50) values ranging from(38.69±0.86) to(203.45±1.03) μmol·L~(-1).

A new sesquiterpene from Chloranthus henryi / 中国中药杂志

Eight sesquiterpenes were isolated and purified from the ethanol extract of Chloranthus henryi by column chromatographies over silica gel, ODS and Sephadex LH-20,and preparative HPLC. Their chemical structures were established by spectral data and physiochemical properties as(1S,6S,8S,10R)-8-ethoxy-10-methoxychlomultin C(1),tianmushanol(2),multistalide A(3),myrrhterpenoid N(4),1α,9α-dihydroxy-8,12-expoxy-eudesma-4,7,11-trien-6-one(5),4β,10α-aromadendranediol(6),oplopanone(7),10α-hydroxycadinan-4-en-3-one(8). Among them, compound(1) was a new compound, and compounds 2-8 were isolated from Chloranthus henryi for the first time.

Chemical composition and acaricidal activity of essential oils and selected terpenes from two species of Psidium in the Cerrado biome of Brazil against Tetranychus urticae / Composición química y actividad acaricida del aceite esencial y terpenos seleccionados de dos especies de Psidium de Cerrado Biome de Brasil contra Tetranychus urticae

The aim of this study was to investigate the chemical composition and acaricidal effect of two Psidium species essential oils and selected compounds on Tetranychus urticae. Essential oils from the leaves of Psidium laruotteanum and Psidium myrsinites were obtained through hydrodistillation, analyzed using CG-FID and CG-MS and evaluated for toxicity to T. urticae by fumigation and residual contact. The susceptibility of T. urticae to monoterpenes and sesquiterpenes was also investigated. The major constituents of the P. laruotteanum oil were (E)-nerolidol (9.6 ± 0.4%) and γ-terpinene (9.4 ± 0.6%) and the major constituents of the P. myrsinites oil were ß-caryophyllene (21.2 ± 0.9%) and α-humulene (10.3 ± 0.5%). Based on the LC50 estimates, no significant differences were found between the two oils regarding toxicity by fumigation or residual contact. ß-Caryophyllene and (E)-nerolidol had the highest level of toxicity, independently of the method investigated. The findings indicate that both oils and selected constituents, especially ß-caryophyllene and (E)-nerolidol, are promising as natural acaricidal agents that affect T. urticae through more than one mode of action.

Los aceites esenciales de las hojas de Psidium laruotteanum y Psidium myrsinites se obtuvieron por hidrodestilación, se analizaron por CG-FID y CG-MS, y se evaluaron sus toxicidades por fumigación y contacto residual contra Tetranychus urticae. Se investigó también la susceptibilidad del T. urticae a monoterpenos y sesquiterpenos. En el aceite esencial de P. laruotteanum, (E)-nerolidol (9.6 ± 0.4%) y γ-terpinene (9.4 ± 0.6%) se identificaron como constituyentes mayoritarios, mientras que en el aceite esencial de P. myrsinites, ß-caryophyllene (21.2 ± 0.9%) y α-humulene (10.3 ± 0.5%) se encontraron como mayoritarios. Con base en las CL50 estimadas, no se observaron diferencias significativas entre las toxicidades de los aceites por fumigación, y tampoco por contacto residual. ßCaryophyllene y (E)-nerolidol presentaron las mayores toxicidades, independientemente del método investigado. Estos resultados indican, que los dos aceites, así como los constituyentes seleccionados, entre los que se destacan ß-caryophyllene y (E)-nerolidol, son promisores agentes acaricidas naturales por actuar en el T. urticae por más de un mecanismo de acción.

Chemical constituents from Syneilesis aconitifolia (II) / 中草药

Objective: To study the chemical constituents from Syneilesis aconitifolia. Methods: The chemical constituents were isolated by silica gel column chromatography and HPLC, and its structure were identified by their spectral data and physicochemical properties analysis. Results: Eighteen compounds were isolated from methanol extract ethyl acetate extracts of S.aconitifolia with the structures identified as 3β-angeloyoxy-eremophil-6-en-8-oxo-12,15β-diacid (1), quercetin-3-O-α-L-rhamnoside (2), triacontanol (3), 8β-methoxyeremophil-3,7(11)-diene-8α,12(6α,15)-dilactone (4), 3,4-dihydroxybenzoic acid (5), 8-oxo-eremophil-6,9-dien-12-oic acid (6), 8βH-eremophil-3,7(11)-dien-12,8α(14,6α)-diolide (7), 8αH-6α,10β-dihydroxyeremophilenolide (8), pinoresinol (9), 6β,8β,10β-trihydroxyeremophil-7(11)-en-12,8-olide (10), 10α,15-dihydroxy-oplopan-4-one (11), 6α,15α-epoxy-1β,4β-dihydroxyeudesmane (12), caryolane-1,9β-diol (13), (-)-clovane-2,9-diol (14), cis-3-hexenyl-β-D-glucopyranoside (15), kaempferol-3-O-α-L-rhamnoside (16), quercetin-3-O-β-D-glucopyranoside(17) and (-)-oplopan-4-one-10-α-O-β-D-glucoside (18). Conclusion: Compound 1 is a new compound, named as syneilesis acid. Compounds 4-16 and 18are isolated from this plant for the first time.

Studies of sesquiterpenes from Myrrha / 中草药

Objective: To study the chemical constituents from Myrrha. Methods: The compounds were isolated and purified by column chromatography over silica gel, Sephadex LH-20, RP-ODS and preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. Results: Ten sesquiterpenes were isolated and identified as 11-methoxyl- guaia-6,10-dien-4α-ol (1), (1R,4S,5R,10R)-isodauc-6-en-10,14-diol (2), 10α-hydroxy-isodauc-6-en-14-al (3), guaia-6,10-dien- 4α,11-diol (4), orientalol B (5), (1S,4R,5R,10S)-isodauc-6-en-10,14-diol (6), (1S,4S,5R,10S)- isodauc-6-en-10,14-diol (7), alismanoid C (8), guaiandiol (9) and canangaterpene VI (10). Conclusion: Compound 1 is a new compound, named as commiphorol A and compounds 2-10 are isolated from the genus for the first time.