Cytotoxic and Anti‐inflammatory Sesquiterpenes from Ainsliaea henryi

Three new sesquiterpenoids, 4α‐hydroxyeudesm‐11(13)‐en‐12‐yl 3‐methylbutanoate ( 1 ), diaspanolide E ( 2 ), and (13α)‐germacra‐1(10),4‐dien‐12,8α‐olid‐15‐oic acid ( 3 ), along with eight known sesquiterpenoids ( 4 – 11 ), were isolated from the aerial parts of Ainsliaea henryi. The chemical structures of compounds 1 – 3 were elucidated by spectroscopic analysis (1D‐, 2D‐NMR, MS and HR/MS). All isolates were evaluated for their inhibitory activities against nitric oxide (NO) production in lipopolysaccharide‐induced RAW264.7 macrophage cells. Compound 10 exhibited significantly inhibition against NO release with an IC₅₀ value of 6.54 ± 0.16 μm . Also, all isolated compounds were tested for cytotoxicity against three human tumor cell lines A549, MGC803, and HCT116, among which compound 5 significantly inhibited the proliferation of MGC803 cell lines with an IC₅₀ value of 2.2 ± 0.2 μm .     

Microbial ωoxylation of trans-Nerolidol and Structurally Related Sesquiterpenoids

Trans-nerolidol and other related terpenoid compounds varying in configuration and chain length, cis-nerolidol, farnesol, and nerylacetone, were used as substrates in biotransformation reactions. These transformations afforded, among the various metabolites obtained, at least one ω-hydroxylated compound of each respective terpenoid. Aspergillus niger ATCC 9142 and Rhodococcus rubropertinctus DSM 43197, incubated with trans-nerolidol, both gave the 12-hydroxy-trans-nerolidol and the latter, in addition, was further oxidized to the 12-carboxylic acid of trans-nerolidol in fairly good yield.     

Sesquiterpenoids from the liverwort Lophozia ventricosa

Two sesquiterpenoids, previously reported as ventricosins A and B, from Lophozia ventricosa have been identified as ent-4(15),7(11)-eudesmadien-8-one and ent-maalioxide, respectively.     

Two New Cytotoxic Sesquiterpenoids from Eupatorium lindleyanum DC.

Two new sesqulterpenold lactones, namely eupallnllides K and L, were isolated from Eupatorlum Ilndleyanum DC. Their structures were determined by spectral methods, Including 1 D-and 2D-NMR spectra. Cytotoxlc evaluatlon showed that eupallnlllde L exhibited potent cytotoxlclty against P-388 and A-549 tumor cell lines with IC50 values of 0.17 and 2.60 p, mol/L, respectively.     

Two New Eremophilane-Type Sesquiterpenoids from Japanese Liverwort Bazzania japonica

Two new eremophilane-type sesquiterpenoids, fusumaols A ( 1 ) and B ( 2 ), were isolated from the stem-leafy liverwort, Bazzania japonica collected in Mori-Machi, Shizuoka, Japan. Their structures were established using extensive spectroscopic (IR, MS, and 2D NMR) data, and the absolute configuration of 1 was determined by the modified Mosher's method. This is the first time eremophilanes have been discovered in the liverwort genus Bazzania. Compounds 1 and 2 were evaluated for their repellent activity against the adult population of the rice weevil Sitophilus zeamais using the modified filter paper impregnation method. Both sesquiterpenoids showed moderate repellent activities.     

Chemistry and Bioactivities of Secondary Metabolites from the Genus Talaromyces

Fungi have especially captured the interest and fascination of natural product chemists in that they produce a dizzying array of natural organic molecules with many unique functional groups and atom arrangements. In this review, we focus on the genus Talaromyces (Trichocomaceae) which has been a hot spot of natural product studies over the last three decades. This review summarized the discovery, structures, and bioactivities of various classes of 151 compounds isolated from both terrestrial and marine derived fungal strains of the genus Talaromyces reported from 1994 to 2019.     

Phytochemical Constituents and Biological Activities of Plants from the Genus Cissampelos

Cissampelos is a significant genus comprising of approximately 21 species of the medicinal plants (Menispermaceae). The plants of this genus are used in traditional medicine for the treatment of various ailments such as asthma, arthritis, dysentery, hyperglycemia, cardiopathy, hypertension and other related problems. These plants are rich in bioactive dibenzylisoquinoline and aborphine as well as small amounts of other ingredients. In recent years, the chemical constituents and pharmacological activities of Cissampelos genus have been paid more and more attention due to their diversity. Herein, we compile the chemical constituents and biological activities on this genus, and summarize the ¹³C-NMR data of the main bioactive ingredients. All information comes from scientific databases such as Google Scholar, PubMed, Sci-Finder, ScienceDirect, Web of Science and CNKI. It provides valuable data for the future research and development of Cissampelos genus.     

Sesquiterpenoids in two different kinds of agarwood

Sesquiterpenoids of an agarwood originating from Aquilaria agallocha and of the other kind of agarwood (Aquilaria sp.; probably Aquilaria malaccensis) were investigated by a combination of GLC and GC/MS. The differences in sesquiterpene composition between the two kinds of agarwood are discussed.     

Sesquiterpenoids of Laurencia majuscula (Ceramiales, Rhodophyta) from the Ryukyu Islands, Japan

Two populations of the red alga Laurencia majuscula (Harvey) Lucas (Rhodomelaceae, Ceramiales) from Taketomi Island and Hateruma Island, the Ryukyu Islands, Japan, have been characterized on the basis of both morphological features and halogenated secondary metabolite content. These populations have smaller and more slender thalli than those of other regions. Furthermore, the populations contain two chamigrane-type Sesquiterpenoids, (2R, 3R, 5S)-5-acetoxy-2-bromo-3-chlorochamigra-7(14),9-dien-8-one and (2R, 3R)-2-bromo-3-chlorochamigra-7(14), 9-dien-8-one, and a laurane-type sesquiterpenoid, debromoisolaurinterol, as secondary metabolites which are different from those previously reported from other populations. These results are consistent with the concept of ‘chemical races’ within a single species of Laurencia.     

黄鞘蕊花中的艾里莫芬烷型倍半萜(英文)

从黄鞘蕊花 (ColeusxanthanthusC .Y .WuetY .C .Huang)的乙酸乙酯部分首次分离得到 3个艾里莫芬烷型倍半萜类化合物 ( 1～ 3) ,其结构由NMR波谱技术及单晶X衍射分析确定。其中 ,化合物 1为新化合物 ,命名为 8,9_断裂_艾里莫芬_1 ( 1 0 ) ,7( 1 1 )_二烯_8,1 2_内酯_9_酸。首次对化合物 2 ( 2 ,9_二氧代优瑞坡森 )和 3( 9_氧代宽眼菊素 )的1H NMR和13C NMR谱进行了全归属。     

Drimane Sesquiterpenoids from the Aspergillus oryzae QXPC‐4

Three new drimane sesquiterpenoids, astellolides C–E ( 1 – 3 , resp.), four new drimane sesquiterpenoid p‐hydroxybenzoates, astellolides F–I ( 4 – 7 , resp.), together with two known compounds astellolides A and B ( 8 and 9 , resp.), have been isolated from the liquid culture of Aspergillus oryzae (strain No. QXPC‐4). Their structures were established by comprehensive analysis of spectroscopic data. The relative and absolute configurations were determined on the basis of NOESY and CD data, together with single‐crystal X‐ray diffraction analyses of compounds 1 – 3 . The metabolites were evaluated for their cytotoxic activities, however, no compounds showed a significant cytotoxicity against the tested cell lines at a concentration of 20 μM .     

Preparative isolation and purification of dicaffeoylquinic acids from the Ainsliaea fragrans champ by high-speed counter-current chromatography

Two dicaffeoylquinic acids, namely 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid, have been successfully separated by high-speed counter-current chromatography (HSCCC) from an extract of Ainsliaea fragrans Champ, followed by an initial clean-up step using AB-8 resin. A two-phase solvent system composed of chloroform:methanol:water (8:8:4) was selected for the isolation with the aqueous-rich phase as the stationary phase and the organic-rich phase as the mobile phase. The developed HSCCC method yielded 34 mg of 3,5-dicaffeoylquinic acid and 17 mg of 4,5-dicaffeoylquinic acid from 150 mg of the crude sample in a one-step separation with purities of 98 and 95%, respectively, as determined by HPLC. The structures of the two compounds were identified from ESI/MS, (1)H- and (13)C-NMR spectroscopic data.     

Nitric Oxide Production Inhibitory Eudesmane‐Type Sesquiterpenoids from Artemisia argyi

Six new eudesmane‐type sesquiterpene derivatives, artemargyinins A–F were isolated from the leaves of Artemisia argyi. Their structures were elucidated based on the extensive analysis of spectroscopic data. Artemargyinins A–F feature a lactone ring‐opening eudesmane‐type sesquiterpene with an isoprenoid group at C(8). All compounds were tested for their inhibitory effects on lipopolysaccharide‐induced nitric oxide (NO) production in RAW264.7 macrophages. Artemargyinins A–F showed more potent NO production inhibitory activity with IC₅₀ values ranging from 7.66±0.53 to 61.19±2.54 μM than the positive control quercetin (IC₅₀=74.34±1.39 μM). Among them, artemargyinins C and D exhibited strong inhibitory activity with IC₅₀ values of 8.08±0.21 and 7.66±0.53 μM, respectively.     

菊三七属植物化学成分及药理作用的研究进展

菊科菊三七属植物中含有生物碱类、黄酮类、香豆素类、三萜类、甾体类及其皂苷、倍半萜类、酚酸类、脑苷脂类等化学成分,具有良好的止血、降血糖、降血压、抗肿瘤、抗炎、抗凝血等药理活性。可见,该属植物化学成分丰富,药理活性多样,极具药用及食用保健价值。本文就近年来菊三七属植物的化学成分和药理作用研究进展作一综述。     

A Systematic Review on Phytochemistry,Ethnobotany and Biological Activities of the Genus Bunium L.

The aim of this review article is to present, for the first time, an appraisal of the phytochemical, ethnobotanical and pharmacological data on Bunium species. The literature search was conducted using the Scopus, Google Scholar and PubMed databases. The genus Bunium has been found to produce both essential oil (EO), mainly comprising monoterpenes and sesquiterpenes, and non-volatile components mainly coumarins and flavonoids. There are several pharmacological activities associated with the Bunium species, especially antioxidant, antibacterial and antifungal properties. The chemotaxonomic appraisal of the phytochemical pattern of the genus is in sink with the current classification of the family. Moreover, this review confirms the significant ethnobotanical and pharmacological potential of different Bunium species.     

Eremophilane Sesquiterpenoids from Coleus xanthanthus (in English)

A new eremophilane sesquiterpenoid, along with two known ones, was isolated from the ethyl acetate soluble fraction of the aerial part of Coleus xanthanthus C. Y. Wu et Y. C. Huang. Their structures were elucidated as 4,5,11-trimethyl-8,9-seco-1(10),7(11)-eremophiladien-8,12-olid-9-oic acid (1), 2,9-dioxoeuryopsin (2) and 9-oxoeuryopsin (3) by spectral methods. The H-NMR and 13C-NMR data of compounds 1, 2 and 3 were unambiguously assigned on the basis of two-dimensional NMR spectroscopy.     

Chemical Constituents of Plants from the Genus Psychotria

Psychotria is a genus of ca. 1500 species in the family Rubiaceae. Up to now, 41 species of the Psychotria genus have been chemically investigated, and 159 compounds, including alkaloids of indole, quinoline and benzoquinolizidine type, terpenoids, steroids, phenolics and aliphatic compounds have been isolated. These compounds show potent bioactivities, such as antimicrobial, antiviral, and antiparasitic activities.