bluuebunny/crossref_metadata_2025 huggingface dataset:
A Fragmentation Study of Six C21 Steroidal Aglycones by Electrospray Ionization Ion-Trap Time-of-Flight Tandem Mass Spectrometry
Authors: Chen Xing-Long , Geng Chang-An , Chen Ji-Jun
Published: March 2019

The fragmentation patterns of six C21 steroidal aglycones, metaplexigenin (1), caudatin (2), qingyangshengenin (3), penupogenin (4), 20-cinnamoylsarcostin (5), and gagamine (6), were analyzed by high-resolution electrospray ionization ion-trap time-of-flight tandem mass spectrometry (HR-ESI-IT-TOF-MSn). The [M-H]+ ions of steroids 1-3 that contain a carbonyl functional group at C-20 (Type I) and [M+H]+ ions of steroids 5-6 that possess a hydroxyl group at C-20 (Type II) were readily observed in MS analyses. The fragmentation pathways and diagnostic fragment ions for these six steroidal aglycones were proposed on the basis of their MSn analyses. The common fragmentation pathways for type I steroidal aglycones include the neutral loss of the ester group at C-12 and the hydroxyl moieties on the steroid skeleton, as well as the cleavage of ring D. Their diagnostic fragment ions were identified as m/ z 361(B), 343 (C), 325 (D), 307 (F), 283 (G), 259 (E), and 243 (H). The fragmentation behavior of penupogenin (4) in type II was similar to those of type I, with m/ z 363 (B’), 345 (C’), 327 (D’), 309 (F’), 283 (G), and 243 (H) as its diagnostic fragment ions. The ester group at C-20 was difficult to cleave in the MSn analyses of 20-cinnamoylsarcostin (5) and gagamine (6) so that the loss of this ester group was slower than that at C-12 and hydroxyl groups; the key ions at m/z 329 (I), 311 (J), 293 (K), and 275 (L) were characteristic for 5 and 6. The base ion peaks were derived from the loss of the substituent group at either C-12 or C-17 for both type I and type II steroidal aglycones.
Chemical Constituents of Euonymus glabra
Authors: Ren Jie , Xie Yang-Guo , Wang Xing , Yan Shi-Kai , Jin Hui-Zi , Zhang Wei-Dong
Published: March 2019

One new phenolic compound (1) and one new flavan (2), together with eight known compounds (3–10) were isolated from the stems and twigs of Euonymus glabra Roxb. Their structures were elucidated mainly on the basis of 1D and 2D spectroscopic methods and circular dichroism analysis. In addition, compounds 1–10 were tested for their inhibitory effects against LPS-induced NO production in RAW264.7 macrophages. Compounds 1–5 and 7 exhibited moderate inhibitory activities with IC50 values ranged from 5.1 to 11.9 μM.
Chemical Constituents of Cordyceps cicadae
Authors: Chu Zhi-Bo , Chang Jun , Zhu Ying , Sun Xun
Published: March 2019

One new bifuran derivative (1), together with fourteen known compounds, were isolated from Cordyceps cicadae X. Q. Shing. The known compounds included nine nucleosides, uracil (2), uridine (3), 2′-deoxyuridine (4), 2′-deoxyinosine (5), guanosine (6), 2′-deoxyguanosine (7), thymidine (8), adenosine (9), and 2′-deoxyadenosine (10); three amino acids tryptophan (11), phenylalanine (12), and tyrosine (13); and two dopamine analogues N-acetylnoradrenaline (14) and its dimer, trans–2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-( N-acetyl-2″-amino-ethylene)-1,4-benzodioxane (15). Their structures were decisively elucidated by spectroscopic analysis, including 1D and 2D NMR techniques.
A Rapid Study of Botanical Drug–Drug Interaction with Protein by Re-ligand Fishing using Human Serum Albumin–Functionalized Magnetic Nanoparticles
Authors: Qing Lin-Sen , Xue Ying , Ding Li-Sheng , Liu Yi-Ming , Liang Jian , Liao Xun
Published: March 2019

A great many active constituents of botanical drugs bind to human serum albumin (HSA) reversibly with a dynamic balance between the free- and bound-forms in blood. The curative or side effect of a drug depends on its free-form level, which is always influenced by other drugs, combined dosed or multi-constituents of botanical drugs. This paper presented a rapid and convenient methodology to investigate the drug-drug interactions with HSA. The interaction of two steroidal saponins, dioscin and pseudo-protodioscin, from a botanical drug was studied for their equilibrium time and equilibrium amount by re-ligand fishing using HSA functionalized magnetic nanoparticles. A clear competitive situation was obtained by this method. The equilibrium was reached soon about 15 s at a ratio of 0.44: 1. Furthermore, the interaction of pseudo-protodioscin to total steroidal saponins from DAXXK was also studied. The operation procedures of this method were faster and more convenient compared with other methods reported.
A New Cytotoxic Clerodane Diterpene from Casearia Graveolens Twigs
Authors: Meesakul Pornphimol , Ritthiwigrom Thunwadee , Cheenpracha Sarot , Sripisut Tawanun , Maneerat Wisanu , Machan Theeraphan , Laphookhieo Surat
Published: March 2019

The first phytochemical investigation of Casearia graveolens twigs led to the isolation and identification of a new clerodane diterpene, caseariagraveolin (1), together with six known compounds (2–7). Their structures were elucidated by intensive analysis of their spectroscopic data. Compound 1 showed strong cytotoxicity against oral cavity and breast cancer cell lines with IC50 values of 2.48 and 6.63 μM, respectively.
Synthesis of a Novel 1,2,4-Oxadiazole Diterpene from the Oxime of the Methyl Ester of 1β,13-Epoxydihydroquinopimaric Acid
Authors: Tretyakova Elena V. , Salimova Elena V. , Odinokov Victor N. , Dzhemilev Usein M.
Published: March 2019

Oximation of the dihydroquinopimaric acid O-cyanoethylderivative (2) via the amidoxime 3, and cyclization with trifluoroacetic anhydride resulted in a new 1,2,4-oxadiazole diterpenoid (4).
Antimicrobial Metabolites from a Marine-Derived Actinomycete in Vietnam's East Sea
Authors: Thi Quyen Vu , Tran Van Hieu , Mai Huong Doan Thi , Le Cong Vinh , Hong Minh Le Thi , Murphy Brian T. , Chau Van Minh , Pham Van Cuong
Published: March 2019

Two new compounds, a quinoline alkaloid (1) and a 1,4-dioxane derivative (2), were isolated from culture broth of the marine-derived actinomycete Micromonospora sp. (strain G019) by bioassay-guided fractionation. This actinomycete strain was isolated from sediment, collected at Cát Bà Peninsula, Vietnam. The taxonomic identification was achieved by analysis of 16S rRNA gene sequences. On the basis of morphological and phylogenetic evidence, strain G019 was assigned to the genus Micromonospora. The structures of 1 and 2 were established by spectroscopic data analysis, including one- and two-dimensional NMR, and MS. Compound 1 was found to have antibacterial activity against Escherichia coli (MIC: 48 μg/mL), Salmonella enterica (MIC: 96 μg/mL) and Enterococcus faecalis (MIC: 128 μg/mL), while compound 2 showed inhibitory activity against Enterococcus faecalis (MIC: 32 μg/mL) and Candida albicans (MIC: 64 μg/mL).
Molecular Docking and Binding Mode Analysis of Plant Alkaloids as in Vitro and in silico Inhibitors of Trypanothione Reductase from Trypanosoma cruzi
Authors: Argüelles Alonso J. , Cordell Geoffrey A. , Maruenda Helena
Published: March 2019

Trypanothione reductase (TryR) is a key enzyme in the metabolism of Trypanosoma cruzi, the parasite responsible for Chagas disease. The available repertoire of TryR inhibitors relies heavily on synthetic substrates of limited structural diversity, and less on plant-derived natural products. In this study, a molecular docking procedure using a Lamarckian Genetic Algorithm was implemented to examine the protein-ligand binding interactions of strong in vitro inhibitors for which no X-ray data is available. In addition, a small, skeletally diverse, set of natural alkaloids was assessed computationally against T. cruzi TryR in search of new scaffolds for lead development. The preferential binding mode (low number of clusters, high cluster population), together with the deduced binding interactions were used to discriminate among the virtual inhibitors. This study confirms the prior in vitro data and proposes quebrachamine, cephalotaxine, cryptolepine, (22 S,25 S)-tomatidine, (22 R,25 S)-solanidine, and (22 R,25 R)-solasodine as new alkaloid scaffold leads in the search for more potent and selective TryR inhibitors.
Further Insight into Polycyclization Cascades of Acyclic Geranylfarnesol and its Acetate by Squalene-hopene Cyclase from Alicyclobacillus Acidocaldarius
Authors: Cheng Jun , Nakano Chiaki , Shi Guang Lu , Hoshino Tsutomu
Published: March 2019

The enzymatic reactions of geranylfarnesol (8) and its acetate 9, classified as sesterterpenes (C25), using squalene-hopene cyclase (SHC) were investigated. The enzymatic reaction of 8 afforded 6/6-fused bicyclic 20, 6/6/6-fused tricyclic 21, and 6/6/6/6-fused tetracyclic compounds 22 and 23 as the main products (35% yield), whereas that of 9 afforded two 6/6/6-fused tricyclic compounds 24 and 25 in a high yield (76.3%) and a small amount (5.0%) of 26 (the acetate of 22). A significantly higher conversion of 9 indicates that the arrangement of the substrate in the reaction cavity changed. The lipophilic nature and/or the bulkiness of the acetyl group may have changed its binding with SHC, thus placing the terminal double bond of 9 in the vicinity of the DXDD motif of SHC, which is responsible for the proton attack on the double bond to initiate the polycyclization reaction. The results obtained for 8 are different to some extent than those reported by Shinozaki et al. The products obtained in this study were deprotonated compounds; however, the products reported by Shinozaki et al. were hydroxylated compounds.
Six New Lanostane Triterpenoids from the Fruiting Body of Tyromyces Sambuceus and Antiproliferative Activity
Authors: Kokudo Naoki , Okazoe Mina , Takahashi Joji , Iseki Kanako , Yoshikawa Kazuko , Imagawa Hirosi , Hashimoto Toshihiro , Noji Masaaki , Umeyama Akemi
Published: March 2019

During the search for secondary metabolites with antiproliferative activity, six new lanostane triterpenoids, tyrosamic acids A-F (1–6) together with ten known compounds (7–16), were isolated from the fruiting body of Tyromyces sambuceus. Their structures were elucidated using MS analyses, extensive 2D-heteronuclear NMR data interpretation and the structure of 3 was further confirmed by single-crystal X-ray data analyses. All lanostane triterpenoids (1–16) possesses a carboxy group at C-20 position and their strength of antiproliferative activity was affected by the presence or absence of a hydroxy group at C-15 position and at the side chain. Four of the compounds (1, 6, 10, 14) showed antiproliferative activities against human cancer cell lines with IC50 values of 16.8–48.3 μM (HL-60).
Stereochemistry of a Rhododaurichromanic Acid Derivative
Authors: Swamy Mahadeva M. M. , Mándi Attila , Anetai Masaki , Monde Kenji
Published: March 2019

A rhododaurichromanic acid A derivative was synthesized from the naturally occurring daurichromenic acid in enantiomeric pure form. Its absolute configuration was elucidated by applying VCD, ECD and DFT calculations.
Hydroxylation and Glycosylation of Phenylpropanoids by Cultured Cells of Phytolacca Americana
Authors: Shimoda Kei , Kubota Naoji , Uesugi Daisuke , Tanigawa Masato , Hamada Hiroki
Published: March 2019

Hydroxylation and glycosylation of cinnamic acid, p-coumaric acid, caffeic acid, and ferulic acid were investigated using cultured plant cells of Phytolacca americana as biocatalysts. Regioselective hydroxylation at the 4-position of cinnamic acid and 3-position of p-coumaric acid was observed. Although cinnamic acid was transformed to mono-glucoside products, di-glycosylation occurred in the case of the biotransformation of p-coumaric acid, caffeic acid, and ferulic acid.
Acidiscalide, A New Glycosylated Macrolide from the Marine Actinomycete Streptomyces Acidiscabies
Authors: Agena Akihisa , Hermawan Idam , Fujiwara Takeshi , Kanamoto Akihiko , Tanaka Junichi
Published: March 2019

A new macrolide named acidiscalide (2), and a known protein synthesis inhibitor, cycloheximide (1), were isolated from the culture broth of a strain of actinomycete, Streptomyces acidiscabies, coded SCTA0002 collected from the coast of Okinawa. The structure of acidiscalide (2) was elucidated to be a glycosylated macrolide having a 24-membered ring on the basis of spectroscopic analysis. Although the stereochemistry could not be determined due to decomposition in the course of the study, it was confirmed that acidiscalide (2) possessed a new molecular scaffold.
Antimicrobial Constituents from Allium Hookeri Root
Authors: Kim Jung-Eun , Seo Ji-Hye , Bae Min-Suk , Bae Chun-Sik , Yoo Jin-Cheol , Bang Mi-Ae , Cho Seung-Sik , Park Dae-Hun
Published: March 2019

In this study, we partially purified the ethyl acetate soluble fraction of the ethanol extract of the root of Allum hookeri. We identified seven compounds, benzoic acid, tetradecanoic acid, hexadecanoic acid, ferulic acid, cinnamic acid, octadecanoic acid and hexanedioic acid, that have antimicrobial activity using GC-MS, and evaluated the antimicrobial susceptibility and MIC (minimum inhibitory concentration) against multidrug-resistant bacteria.
Coconut Laurels: The Leaf Essential Oils from Four Endemic Australian Cryptocarya Species: C. Bellendenkerana, C. Cocosoides, C. Cunninghamii and C. Lividula (Lauraceae)
Authors: Brophy Joseph J. , Forster Paul I. , Goldsack Robert J.
Published: March 2019

The leaf oils of four species of Cryptocarya, endemic to Australia, were examined. These species are known colloquially as ‘coconut laurels’ due to the purported distinctive aroma from the crushed foliage. C cocosoides produced an oil in which bicyclogermacrene (3–26%), spathulenol (16–47%), massoia lactone (6-pentyl-5,6-dihydro-2 H-pyran-2-one) (11–15%), (6-heptyl-5,6-dihydro-2 H-pyran-2-one (0.3–3%) and benzyl benzoate (0.2–5%) were the principal components. C cunninghamii showed a second chemotype to that previously published, with benzyl benzoate (80.2%) being the principal component. C bellendenkerana gave a leaf oil in which the major components were the terpenes limonene (8.3%), β-phellandrene (11.8%) and viridiflorene (9.1%). The principal components of the leaf oil of C lividula were bicyclogermacrene (26.1%), spathulenol (21.1%) and β-eudesmol (6.1%). Benzaldehyde and acetophenone were both present in amounts of less than 0.7%. Only C. cocosoides and C cunninghamii have been found to have a ‘coconut’ aroma mainly due to the presence of massoia lactone and homologues.
Chemical Composition of the Fruit Oils of Five Fortunella Species Grown in the Same Pedoclimatic Conditions in Corsica (France)
Authors: Sutour Sylvain , Luro François , Bradesi Pascale , Casanova Joseph , Tomi Félix
Published: March 2019

Fruit oil from five species of kumquat ( Fortunella japonica, F. margarita, F. crassifolia, F. obovata, and F. hindsii) grown in the same pedoclimatic conditions have been analyzed by a combination of chromatographic and spectroscopic techniques. The compositions of the five fruit oils were strongly dominated by limonene (84.2–96.3%). Other components present with appreciable contents were myrcene (1.3–12.9%) and germacrene D (0.3–2.4%).
Compositional Analysis of Lavandula pinnata Essential Oils
Authors: Argentieri Maria Pia , De Lucia Barbara , Cristiano Giuseppe , Avato Pinarosa
Published: March 2019

The genus Lavandula includes about thirty species plus a number of intraspecific taxa and hybrids, which are distributed in the Mediterranean area. The traditional use of lavender both as perfume or medicinal plant is known since antiquity. Nowadays several species are extensively cultivated for the extraction of their essential oils (EOs) which are used in manufactured products like cosmetics and perfumes or in phytotherapy. Lavandula pinnata L. f. (syn L. pinnata Lundmark) is a rare species native to the Canary Islands used in folk medicine as relaxant and also a valuable remedy against bites. To the best of our knowledge, EOs from L. pinnata have been very little studied. The present paper reports on the quali- and quantitative compositional profile of the EOs distilled (by a Spring type apparatus) from the aerial parts (flowers and leaves) of this species cultivated in soilless conditions. Chemical analyses by means of GC and GC-MS techniques have indicated that oxygenated monoterpenes are the main constituents of both the flowers (68.30%) and the leaves (83.65%). Carvacrol is the main compound which characterizes the EOs of this species. In addition, discrete amounts of spathulenol (12.22%) and caryophyllene oxide (14.62%) have been detected in flowers EOs, while leaves EOs contained small amounts of carvacrol methyl ether (2.52%).
Changes in Volatile Compounds during Aging of Sweet Fennel Fruits-Comparison of Hydrodistillation and Static Headspace Sampling Methods
Authors: Najdoska-Bogdanov Menče , Bogdanov Jane B. , Stefova Marina
Published: March 2019

Two extraction methods for subsequent gas chromatographic (GC) determination of volatiles from freshly harvested and aged fennel fruit samples ( Foeniculum vulgare Mill.,ssp. vulgare var. dulce) have been compared. Hydrodistillation followed by GC-FID and GC-MS analysis was used as a standard method for essential oil characterization, while static headspace followed by GC (SHS-GC-FID) was used as a comparative method for determination of volatile components. As the fennel fruit ages, there is a gradual loss of the volatile components as indicated by the lower yield of essential oil and lower content of volatiles, as indicated by the alternative SHS-GC-FID analysis. Slight differences observed for the main components ( trans-anethole, estragole, fenchone, and limonene) using the two methods are negligible, indicating that these volatiles did not undergo chemical transformation during the sample preparation procedures. A difference in anisaldehyde content was observed when the composition of the hydrodistilled essential oil was compared with the SHS-GC-FIDanalysis of volatiles and explanation for the variation of anisaldehyde content and the origin of other compounds was suggested. Comparison of the obtained results showed that limonene oxides, carvone and carveolare detectable in SHS-GC-FID analysis of the aged fennel fruits, while in hydrodistilled samples analyzed by GC-FID they were not present. Another observed difference was the appearance of products in significant amounts with higher retention times than trans-anethole, namely threo- and erythro-anethole β-hydroxymethylether and anethole glycol that are not detectable in the essential oil obtained by hydrodistillation. So, the relative abundance of the major components is comparable between these two methods for fennel seed up to 3 years from harvest and they can be used interchangeably depending on the purpose and amount of material. Furthermore, SHS-GC-FID can be used for assessment of maximum storage time and quality of fennel fruit suitable for human consumption.
The Terpenoid Biosynthesis Toolkit of Trichoderma
Authors: Bansal Ravindra , Mukherjee Prasun Kumar
Published: March 2019

The widely used biotechnologically important fungi belonging to the genus Trichoderma are rich sources of secondary metabolites. Even though the genomes of several Trichoderma spp. have been published, and data are available on the genes involved in biosynthesis of non-ribosomal peptide synthetases and polyketide synthases, no genome-wide data are available for the terpenoid biosynthesis machinery in these organisms. In the present study, we have identified the genes involved in terpene biosynthesis in the genomes of three Trichoderma spp., viz., T. virens, T. atroviride and T. reesei. While the genes involved in the condensation steps are highly conserved across the three species, these fungi differed in the number and organization of terpene cyclases. T. virens genome harbours eleven terpene cyclases, while T. atroviride harbours seven, and T. reeseisix in their genomes; seven, three and two being part of putative secondary metabolism related gene clusters.
Anti-angiogenic Activity and Mechanism of Sesquiterpene Lactones from Centipeda minima
Authors: Huang Weihuan , Yu Xiaobin , Liang Ning , Ge Wei , Kwok Hin Fai , Lau Clara Bik-San , Li Yaolan , Chung Hau Yin
Published: March 2019

Centipeda minima is a Chinese herbal medicine used in the treatment of various diseases including cancer. An ethanol extract of the herb, its four fractions with different polarities, and two volatile oils prepared by steam distillation (SD) and supercritical fluid extraction (SFE) were investigated for their anti-angiogenic activity in a wild-type zebrafish model using a quantitative endogenous alkaline phosphatase (EAP) assay. The SFE oil displayed potent anti-angiogenic activity. Fifteen sesquiterpene lactones (SLs; compounds 1–15) isolated from the SFE oil were evaluated for their anti-angiogenic effect. Results revealed that pseudoguaianolide type SLs (1–8) inhibited vessel formation in the zebrafish embryos while guaianolide type SLs (9–15) showed little effect. Among the active ones, 6- O-angeloylenolin (1), a major component of SFE oil, possessed the strongest effect by reducing vessel formation in zebrafish embryos to 40% of the control value at 29.7 μM. Further study using the Tg ( fli1a:EGFP) y1-type zebrafish model revealed that it blocked both intersegmental blood vessels (ISVs) and subintestinal vessels plexus (SIVs) formation in zebrafish embryos. Real-time polymerase chain reaction assay on the wild-type zebrafish embryos suggested that 6- O-angeloylenolin affected multiple molecular targets related to angiogenesis including VEGF receptor, angiopoietin, and its receptors. Taken together, our findings demonstrate that C. minima possesses anti-angiogenic activity, and 6- O-angeloylenolin is a promising candidate for the development of an anti-angiogenic agent.
Two New Compounds from the Leaves of Glochidion obliquum
Authors: Thu Vu Kim , Van Thang Nguyen , Nhiem Nguyen Xuan , Anh Hoang Le Tuan , Yen Pham Hai , Hang Dan Thi Thuy , Van Minh Chau , Van Kiem Phan
Published: March 2019

Using combined chromatographic methods, two new compounds, 6β,9β:9,13-diepoxymegastig-4-en-3β-ol (1), 5α,6α-epoxy D:C-friedoolean-8-en-3β-ol (2) were isolated from the methanol extract of the leaves of Glochidion obliquum Decne. Their structures were elucidated by 1D- and 2D-NMR spectra and in comparison with those reported in the literature.
Two New Compounds from Artemisia sacrorum
Authors: Wang Qinghu , Wu Rongjun , Han Narenchaoketu , Dai Nayintai , Wu Jiesi
Published: March 2019

Two new compounds, named as sacric acid A (1) and sacric acid B (2), were isolated from the EtOAc extract of Artemisia sacrorum Ledeb. This is the first report on the structure elucidation of these compounds based on UV, IR, and extensive 1D and 2D NMR spectroscopic, and ESI-MS techniques.
Comparative Chemical Analysis of Mentha piperita and M. spicata and a Fast Assessment of Commercial Peppermint Teas
Authors: Buleandra Mihaela , Oprea Eliza , Popa Dana Elena , David Iulia Gabriela , Moldovan Zenovia , Mihai Iuliana , Badea Irinel Adriana
Published: March 2019

The hydrodistilled essential oils and volatile compounds (by static headspaces technique) of Mentha piperita L. and M. spicata L. were characterized by GC-MS. Headspace analysis of Mentha piperita revealed the existence of menthone (25.4%), 1,8-cineole (17.7%) and menthol (12.1%) as the main components, while the essential oil contained high amounts of menthol (46.8%) and menthone (25.6%). By contrast, headspace analysis of M spicata showed a high content of limonene (37.0%) together with carvone (13.0%), β-pinene (10.4%) and α-pinene (9.8%), while the essential oil was reach in carvone (51.7%), dihydrocarveol (11.5%) and cis-dihydrocarvone (9.1%). Eleven samples of peppermint tea available on the Romanian market were analysed by headspace GC-MS. The volatile profile of the tea samples was compared with that of Mentha piperita L. and certain differences were emphasized and discussed.
Antiherpetic Plants: A Review of Active Extracts, Isolated Compounds, and Bioassays
Authors: Silva-Mares David , Torres-López Ernesto , Rivas-Galindo Verónica M.
Published: March 2019

Herpes simplex is a disease that is widely distributed throughout the world. It is caused by herpes simplex virus type 1 (HSV-1) and simplex virus type 2 (HSV-2). The drugs of choice for treatment are acyclovir (ACV), Penciclovir (PCV) and other guanine analogues, which have the same mechanism of action. However, due to the constant increase of ACV-resistant strains in immunocompromised patients, it is necessary to find new treatment alternatives. It has been shown that natural products are a good alternative for the treatment of these diseases as well as being an excellent source of compounds with anti-herpetic activity, which may be useful for the development of new drugs and act through a mechanism of action different from ACV and PCV. This paper compiles reports on extracts and compounds isolated from plants that have anti-herpetic activity. We present an analysis of the solvents most widely used for extraction from plants as well as cells and commonly used methods for evaluating cytotoxic and anti-herpetic activity. Families that have a higher number of plants with anti-herpetic activity are evaluated, and we also highlight the importance of studies of mechanisms of action of extracts and compounds with anti-herpetic activity.
The Co-identity of Lipiarmycin A3 and Tiacumicin B
Authors: Bedeschi Angelo , Fonte Piera , Fronza Giovanni , Fuganti Claudio , Serra Stefano
Published: March 2019

The co-identity of the antibiotics lipiarmycin A3 obtained from Actinoplanes deccanensis and tiacumicin B obtained from Dactylosporangium aurantiacum was unambiguously demonstrated through a number of experimental means. Spectroscopic analyses performed on both the antibiotics themselves and on their derivatives showed no difference between the two series of compounds. Moreover, unambiguous confirmation of the postulated identity of the two compounds was achieved by chemical degradation of lipiarmycin A3 and isolation of (3 S,4 R)-pentane-1,3,4-triol triacetate whose relative configuration was assigned by comparison with the authentic erythro and threo pentane-1,3,4-triol triacetates, obtained by chemical synthesis.
A New Monoterpenoid and a New Flavonoid Glycoside from the Peels of Clausena lansium
Authors: Deng Hui-Dong , Cai Cai-Hong , Liu Shuai , Zeng Yan-Bo , Mei Wen-Li , He Fan , Hua Min , Dai Hao-Fu , Li Shao-Peng
Published: March 2019

One new monoterpenoid, nerol oxide-8-carboxylic acid (1), and one new flavonoid glycoside, claulansoside A (2), together with six known compounds, clausenamide (3), quercetin (4), isorhamnetin (5), dihydromyric (6), 2′',3′'-dihydroxyanisolactone (7) and ( E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen (8), have been isolated from the peels of Clausena lansium (Lour.) Skeels. Their structures were determined using a combination of 1D, and 2D NMR (HMQC, HMBC, COSY and NOESY) techniques, and HR-ESI-MS analyses. Compounds 1 and 7 exhibited antibacterial activity against Staphylococcus aureus with the diameter of inhibition zones of 11.5 mm and 14.2 mm. Compounds 3 and 6 showed α-glucosidase inhibitory activity in vitro.
Sesquiterpenoid Lactones in Tanacetum huronense Inhibit Human Glioblastoma Cell Proliferation
Authors: Dissanayake Amila A. , Bejcek Bruce E. , Zhang Chuan-Rui , Nair Muraleedharan G.
Published: March 2019

Tanacetum huronense (Lake Huron tansy), which is native to the upper Midwest region of USA and Canada, was examined for the presence of anticancer compounds using an in vitro human tumor cell proliferation inhibition assay, with glioblastoma derived cell line U-87 MG. Bioassay-directed purification of the ethyl acetate extract of the aerial portion of this plant identified six active sesquiterpenoid lactones (1–6). Among these, compounds 5 and 6 are new structural analogs. One of the most abundant isolates, tanacin (4), exhibited the greatest inhibition with an IC50 value of 4.5 μg/mL.
Immunological Adjuvant Activity of Pectinioside A, the Steroidal Saponin from the Starfish Patiria pectinifera
Authors: Kawase Osamu , Ohno Osamu , Suenaga Kiyotake , Xuan Xuenan
Published: March 2019

The steroidal saponin, pectinioside A, was isolated from the starfish, Patiria pectinifera. When it was subcutaneously injected into mice with ovalbumin (OVA), it facilitated the production of OVA-specific total IgG and IgG1 but not IgG2a. To our knowledge, this is the first report suggesting that starfish saponin has the potential to be an immunological adjuvant, stimulating Th2 type immune response.
Optimization and Scale-up of Inulin Extraction from Taraxacum kok-saghyz roots
Authors: Hahn Thomas , Klemm Andrea , Zieße Patrick , Harms Karsten , Wach Wolfgang , Rupp Steffen , Hirth Thomas , Zibek Susanne
Published: March 2019

The optimization and scale-up of inulin extraction from Taraxacum kok-saghyz Rodin was successfully performed. Evaluating solubility investigations, the extraction temperature was fixed at 85°C. The inulin stability regarding degradation or hydrolysis could be confirmed by extraction in the presence of model inulin. Confirming stability at the given conditions the isolation procedure was transferred from a 1 L- to a 1 m3-reactor. The Reynolds number was selected as the relevant dimensionless number that has to remain constant in both scales. The stirrer speed in the large scale was adjusted to 3.25 rpm regarding a 300 rpm stirrer speed in the 1 L-scale and relevant physical and process engineering parameters. Assumptions were confirmed by approximately homologous extraction kinetics in both scales. Since T. kok-saghyz is in the focus of research due to its rubber content side-product isolation from residual biomass it is of great economic interest. Inulin is one of these additional side-products that can be isolated in high quantity (~ 35% of dry mass) and with a high average degree of polymerization (15.5) in large scale with a purity of 77%.
Essential Oils and Non-volatile Compounds Derived from Chamaecyparis obtusa: Broad Spectrum Antimicrobial Activity against Infectious Bacteria and MDR(multidrug resistant) Strains
Authors: Bae Min-Suk , Park Dae-Hun , Choi Chul-Yung , Kim Gye-Yeop , Yoo Jin-Cheol , Cho Seung-Sik
Published: March 2019

The aim of this study was to evaluate the antibacterial activity of essential oil from Chamaecyparis obtusa against general infectious microbes and drug resistant strains of clinical origin. The results indicate that both essential oil and non-volatile residue have broad inhibitory activity against test strains. Essential oil and non-volatile residues showed antimicrobial activity not only against general infectious bacteria, but also against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains.
Two New Oleanane-type Triterpenoids from Methanolyzed Saponins of Momordica cochinchinensis
Authors: Fan Rong , Cheng Rong-Rong , Zhu Hong-Tao , Wang Dong , Yang Chong-Ren , Xu Min , Zhang Ying-Jun
Published: March 2019

Two new oleanane-type triterpenoid saponins (1 and 2) were isolated from the methanolyzed total saponins of the seeds of Momordica cochinchinensis (Lour.) Spreng, together with 16 known compounds (3—18). Their structures were elucidated on the basis of detailed spectroscopic, including ID and 2D NMR, mass spectrometric, methanolysis and LC-MS analysis. All the isolates were tested for their cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7721, PANC-1, A-549, and SW-480) and the glucose uptake activity. The known compound 6 exhibited toxic effects against HL-60 with an IC50 value of 18.1 μM, while 10 showed cytotoxicity against SMMC-7721 and A-549 cell lines, with IC50 values of 34.4 and 32.8 μM, respectively. In addition, the new compound 2 showed glucose uptake activity with a glucose consumption value of 0.29 μM at 10 μM concentration.
Chemical Composition, Antioxidant and Cytotoxic Activities of Essential Oil of the Inflorescence of Anacamptis coriophora subsp. fragrans (Orchidaceae) from Tunisia
Authors: Mokni Ridha El , Hammami Saoussen , Dall'Acqua Stefano , Peron Gregorio , Faidi Khaled , Braude Jeremy Phillip , Sebei Houcine , Aouni Mohamed Hédi El
Published: March 2019

The chemical composition of the essential oil produced by steam distillation of the inflorescences of naturally growing Anacamptis coriophora (L.) R. M. Bateman, Pridgeon & M. W. Chase subsp. fragrans (Pollini) R. M. Bateman, Pridgeon & M. W. Chase (Orchidaceae) from Kroumiria, north-west Tunisia was studied by GC-MS, which led to the identification of 19 volatile components, representing 97% of the oil. The main constituents were methyl-( E)-p-methoxycinnamate (29.3%), 13-heptadecyn-l-ol (18.6%), 2,5-dimethoxybenzyl alcohol (14.1%) and 4-(1,1,3,3-tetramethylbutyl)-phenol (9.0%). DPPH radical scavenging revealed a weak antioxidant activity. In addition, the antiproliferative effects were evaluated on BxPC3 human pancreatic carcinoma cells and on 2008 human ovarian cancer cells showing significant effect. This is the first report of the chemical composition of essential oils obtained from A coriophora subsp. fragrans inflorescences for North Africa. Further studies are needed to understand fully the possible mechanism of action behind the cytotoxic activity of the essential oil.
Essential Oil from Origanum vulgare Completely Inhibits the Growth of Multidrug-Resistant Cystic Fibrosis Pathogens
Authors: Pesavento Giovanna , Maggini Valentina , Maida Isabel , Nostro Antonella Lo , Calonico Carmela , Sassoli Chiara , Perrin Elena , Fondi Marco , Mengoni Alessio , Chiellini Carolina , Vannacci Alfredo , Gallo Eugenia , Gori Luigi , Bogani Patrizia , Bilia Anna Rita , Campana Silvia , Ravenni Novella , Dolce Daniela , Firenzuoli Fabio , Fani Renato
Published: March 2019

Essential oils (EOs) are known to inhibit the growth of a wide range of microorganisms. Particularly interesting is the possible use of EOs to treat multidrug-resistant cystic fibrosis (CF) pathogens. We tested the essential oil (EO) from Origanum vulgare for in vitro antimicrobial activity, against three of the major human opportunistic pathogens responsible for respiratory infections in CF patients; these are methicillin-resistant Staphylococcus aureus, Stenotrophomonas maltophilia and Achromobacter xylosoxidans. Antibiotic susceptibility of each strain was previously tested by the standard disk diffusion method. Most strains were resistant to multiple antibiotics and could be defined as multi-drug-resistant (MDR). The antibacterial activity of O. vulgare EO (OEO) against a panel of 59 bacterial strains was evaluated, with MIC and MBC determined at 24, 48 and 72 hours by a microdilution method. The OEO was effective against all tested strains, although to a different extent. The MBC and MIC of OEO for S. aureus strains were either lower or equal to 0.50%, v/v, for A. xylosoxidans strains were lower or equal to 1% and 0.50%, v/v, respectively; and for S. maltophilia strains were lower or equal to 0.25%, v/v. The results from this study suggest that OEO might exert a role as an antimicrobial in the treatment of CF infections.
Improved Syntheses of (+)-Iridomyrmecin and (-)-Isoiridomyrmecin, Major Components of Matatabilactone
Authors: Adachi Masaatsu , Miyazawa Yu , Nishikawa Toshio
Published: March 2019

Improved syntheses of iridomyrmecin and isoiridomyrmecin, major components of matatabilactone, are described. The synthesis features a direct transformation of nepetalactol into key intermediates by DIBAL-H reduction and provides an expeditious and straightforward production of iridoid lactones for biological investigations of the Matatabi phenomenon.
A New Pimarane-type Diterpenoid from the Seeds of Bowdichia virgilioides
Authors: Kubo Miwa , Uemura Misao , Harada Kenichi , Ohsaki Ayumi , Fukuyama Yoshiyasu
Published: March 2019

A new pimarane-type diterpenoid, sucupiol (1), and nine known furanocassane-type diterpenoids, vouacapane (2), 7β-hydroxyvouacapane (3), 7β-acetoxyvouacapane (4), 6α-hydroxyvouacapane (5), 6α-acetoxyvouacapane (6), sucutinirane F (7), sucutinirane E (8), 6α, 7β-diacetoxyvouacapane (9), and 6α, 7β-diacetoxyvouacapane-14β-al (10), were isolated from the seeds of Bowdichia virgilioides and their structures were elucidated by using 2D NMR data. The isolation of 1 provides evidence to support the presence of intermediate A in the course of biosynthesis of furanocassane-type diterpenoids.
Fallaxosides C1, C2, D1 and D2, Unusual Oligosulfated Triterpene Glycosides from the Sea Cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida, Holothurioidea) and Taxonomic Status of this Animal
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjaschenko Pelageya V. , Dmitrenok Pavel S. , Kalinin Vladimir I. , Martyyas Ekaterina A. , Minin Kirill V.
Published: March 2019

Four new triterpene glycosides, fallaxosides C1 (1), C2 (2), D1 (3) and D2 (4) along with the known cucumarioside A3-2 (5) and koreoside A (6) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All of the glycosides are rare non-holostane derivatives having shortened side chains and contain pentasaccharide carbohydrate moieties with two or three sulfate groups. Structures of these triterpene glycosides and their comparison with those earlier isolated from Cucumaria spp. and Pseudocnus dubiosus leoninus allow us to suggest that the present assignment of C. fallax to the genus Pseudocnus is not correct, and this species should be assigned to the genus Cucumaria. Cytotoxic activity of glycosides 1–5 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied. The glycosides were expectedly not active in all the tests due to the absence of an 18(20)-lactone in their aglycones and the presence of several sulfate groups. There was one exception, cucumarioside A3-2 (5), which demonstrated a weak cytotoxicity against lymphocytes and moderate hemolytic activity.
Efficient Preparation of Various O-Methylquercetins by Selective Demethylation
Authors: Kimura Yuki , Kato Ryo , Oyama Kin-ichi , Kondo Tadao , Yoshida Kumi
Published: March 2019

penta-O-Methylquercetin (2) was prepared by permethylation of quercetin (1). Selective demethylation of 2 using either BBr3 or BCl3/TBAI ( tetra-butylammonium iodide) gave five O-methylquercetins (3-6), with satisfactory yields. The reaction can be easily scaled-up. We established an efficient and large-scale preparation of O-methylquercetins.
Effective Production of Aromatic Polyketides in Streptomyces using a Combined-Culture Method
Authors: Hoshino Shotaro , Okada Masahiro , Onaka Hiroyasu , Abe Ikuro
Published: March 2019

Combined-culture is a fermentation method which efficiently induces secondary metabolite production in Streptomyces by co-culturing them with mycolic acid-containing bacteria. As a result of combined-culture screening of our terrestrial Streptomyces collection using UV-HPLC, one of the tested strains, Streptomyces sp. TAKO-2, produced two known aromatic polyketides, julichrome Q6 (1) and julichrome Q8·8 (2), when co-cultured with the mycolic acid-containing bacterium Tsukamurella pulmonis TP-B0596. The structures of 1 and 2 were confirmed by spectroscopic analysis and literature data.
Constituents from Entada scandens with TRAIL-resistance Overcoming Activity
Authors: Ahmed Firoj , Toume Kazufumi , Ishikawa Naoki , Arai Midori A. , Sadhu Samir K. , Ishibashi Masami
Published: March 2019

Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) has emerged as a promising anticancer agent because of its ability to selectively kill tumor cells. But TRAIL-resistance is a major problem of its therapy. A search for compounds for abrogating TRAIL-resistance has, thus, become an important strategy for anticancer drug discovery. In search of bioactive natural products for overcoming TRAIL-resistance, we previously reported some compounds with TRAIL-resistance overcoming activity. Bioassay guided fractionation of Entada scandens led to the isolation of four compounds (1-4). Of the isolates, compounds 1 and 3 showed moderate TRAIL-resistance overcoming activity in TRAIL-resistant human gastric adenocarcinoma (AGS) cells.
Helvafuranone Produced by the Fungus Aspergillus nidulans BF0142 Isolated from Hot Spring-derived Soil
Authors: Furukawa Takun , Fukuda Takashi , Nagai Kenichiro , Uchida Ryuji , Tomoda Hiroshi
Published: March 2019

The fungus, Aspergillus nidulans BF0142, was isolated from hot spring-derived soil collected at Hell Valley in Noboribetsu, Hokkaido, Japan. A new furanone compound designated helvafuranone (1) was isolated along with microperfuranone (2), 9-hydroxymicroperfuranone (3), diorcinol (4), emestrin (5), and sterigmatocystin (6) from a culture broth of A. nidulans BF0142. The structure of 1 was elucidated as 5-hydroxy-4-(4-hydroxybenzyl)-3-(4-hydroxybenzyl)furanone based on various NMR experiments and chemical modifications.
A New Polycyclic Polyprenylated Acylphloroglucinol Derivative from Garcinia verrucosa
Authors: Rajaonarivelo Mialy , Rakotonandrasana Olga L. , Martin Marie-Thérèse , Dumontet Vincent , Rasoanaivo Philippe
Published: March 2019

In our continuing phytochemical screening program aimed at finding major constituents of endemic Madagascar plants as potential templates for semisynthesis, we investigated the ethyl acetate extract of stem bark of Garcinia verrucosa. Fractionation of the extract led to the isolation of the major compound named garcicosin. Its structure was elucidated by spectroscopic methods including 1D and 2D homo- and heteronuclear NMR techniques (COSY, HSQC, HMBC and NOESY), and HR-mass spectrometry.
A New Seco-Clerodane-Type Diterpenoid from Bornean Liverwort Schistochila acuminata
Authors: Ng Shean-Yeaw , Kamada Takashi , Suleiman Monica , Vairappan Charles S.
Published: March 2019

A new compound, schistochilic acid D (1) and two known compounds (2 and 3) were isolated from MeOH extract of Bornean liverwort Schistochila acuminata collected from Mount Trus Madi, Sabah. The structure of the new metabolite was established based on spectroscopic (1D NMR, 2D NMR, and IR). and HRESIMS data. In addition, another population of S. acuminata collected from Mount Alab (Sabah) yielded four known compounds, 2, 3, 4 and 5. These compounds were tested for their biological potential against the B16-F10 cell line. Compounds 4 and 5 exhibited weak cytotoxic activity.
Volatile Constituents of New Caledonian Frullania Species
Authors: Métoyer Benjamin , Coulerie Paul , Lebouvier Nicolas , Hnawia Edouard , Thouvenot Louis , Asakawa Yoshinori , Raharivelomanana Phila , Nour Mohammed
Published: March 2019

Volatile components of seven Frullania species (Frullaniaceae) from New Caledonia, including five endemic species ( F. bella, F. scalaris, F. mammillosa, F. cornuta and F. falsicornuta), were analyzed by GC-MS in order to index these plants to known chemotypes. Constituents detected in these Frullania species were mainly sesquiterpenes, as well as the bibenzyl dihydrognetin, and the flavonoid naringinin-5,7,4'-trimethyl ether. These compositions allowed an indexation of Frullania species from New Caledonia to cyclocolorenone, sesquiterpene lactone and bibenzyl chemotypes. In addition, qualitative intraspecies variations of chemical composition were very important and made indexation to known chemotypes very tricky. Moreover, two of the endemic liverworts did not possess any biomarker that linked to a known chemotype.
The Iridoid Myodesert-1-ene and Elemol/Eudesmol are found in Distinct Chemotypes of the Australian Aboriginal Medicinal Plant Eremophila dalyana(Scrophulariaceae)
Authors: Sadgrove Nicholas J. , Collins Timothy L. , Legendre Sarah V.A.-M. , Klepp Julian , Jones Graham L. , Greatrex Ben W.
Published: March 2019

The strongly aromatic Australian desert species Eremophila dalyana is an Aboriginal medicinal plant that continues to be used today in Central Australia in the treatment of respiratory complaints and Sarcoptes scabiei infestation. Using hydrodistillation of aerial parts of the plant, the new natural product myodesert-1-ene was isolated in two disjunct populations at up to 98% of the volatiles present in the hydrodistilled oils. Weak antimicrobial activities were observed for whole oils and myodesert-1-ene. Activities in the hydrodistilled oil were attributed to the antimicrobial sesquiterpenes elemol and eudesmol which showed good activity when isolated and were relatively abundant in the chemotype used medicinally. The biogenesis of myodesert-1-ene from iridodial is proposed.
A New Coumarin from the Stems of Pterocarpus indicus
Authors: Sichaem Jirapast , Khumkratok Suttira , Sawasdee Pattara , Tip-pyang Santi
Published: March 2019

The chemical investigation of the crude ethyl acetate extract from Pterocarpus indicus stems led to isolation of a new coumarin, indicusane (1), together with eleven known compounds (2-12). To the best of our knowledge, all isolated coumarins (1-12) are reported for the first time from this plant. Their structures were identified on the basic of spectroscopic data (NMR, MS and ECD) as well as a chemical reaction (Mosher's method). In addition, all isolates were also evaluated for their cholinesterase (ChEs) inhibitory activities, in which only compound 4 exhibited the moderate activity toward AChE and BChE.
Cytotoxic and Antitumor Activity of some Coumarin Derivatives
Authors: Garro Hugo A. , Reta Guillermo F. , Donadel Osvaldo J. , Pungitore Carlos R.
Published: March 2019

Several natural and synthetic coumarins were assayed against different cancer cell lines. Four of them have shown cytotoxicity against a panel of three human solid tumor cell lines (HeLa, T-47D, and WiDr) and a clearly activity/hydrophobicity relationship. Compound 13 proved to be the most active product in all cell lines tested, with values of 8.0 (±0.38) μM against HeLa cells and also able to inhibit Taq DNA polymerase. This dual activity of 13 makes it a candidate to be considered as a “lead” compound in the search for novel antitumor drugs.
Acetophenones from Acronychia pedunculata and their Cancer Chemopreventive Activity
Authors: Ito Chihiro , Hosono Mari , Tokuda Harukuni , Wu Tian-Shung , Itoigawa Masataka
Published: March 2019

From the roots of Acronychia pedunculata (L.) Miq. (Rutaceae) collected in Taiwan, six known and three new acetophenones have been isolated. The new compounds were named acrophenones D (1), E (2), and F (3). Of the acetophenones isolated in this study, prenylacronylin (4) and acronyculatin D (10) exhibited significant inhibitory activity against 12- O-tetradecanoylphorbol 13-acetate-induced Epstein-Barr virus early antigen activation in Raji cells.
Bis-bibenzyls from the Cameroon Liverwort Marchantia debilis
Authors: Anchang Kenneth Yongabi , Novaković Miroslav , Bukvički Danka , Asakawa Yoshinori
Published: March 2019

Liverworts are rich sources of terpenoids and aromatic compounds among which bis-bibenzyls are well known for their wide spectrum of biological activities. This is the first report of chemical analysis of the African liverwort Marchantia debilis Goebel. From the methanol extract marchantinquinone-1′-methyl ether was newly isolated together with three known bis-bibenzyls, marchantin C, marchantinquinone and perrottetin E. The presence of bis-bibenzyls with a quinone moiety is noted for the first time in the Marchantia genus.
1-Acyl-3-O-[β-glucopyranosyl-(1″→6′)-β-glucopyranosyl]-glycerols and Cordycedipeptides B and C, New Metabolites from Bacillus pumilus
Authors: Wang Hongpeng , Drawert Frederike , Steinert Michael , Schulz Stefan , Laatsch Hartmut
Published: March 2019

Four 1-monoacyl-3- O-[β-glucopyranosyl-(1→6)-β-glucopyranosyl]-glycerols (1) and four 1,2-diacyl-3- O-[β-glucopyranosyl-(1→6)-β-glucopyranosyl]-glycerols (2a) with acyl residues consisting of 1:1 mixtures of 1- iso-pentadecanoyl- and 1- anteiso-pentadecanoyl residues and the respective heptadecanoic acid isomers s as main components, have been characterized in the extracts of Bacillus pumilus strain DKS1. Twenty-seven further metabolites, among them the diketopiperazines cordycedipeptide A (3), B (4), and C (5), were obtained. All compounds were elucidated by NMR and MS techniques and fully characterized and tested for antimicrobial activity against Legionella pneumophila.