bluuebunny/crossref_metadata_2025 huggingface dataset:
New Isocoumarins and Related Metabolites from Talaromyces flavus
Authors: He Jun-Wei , Xu Huai-Shuang , Yang Li , He Wei-Wei , Wang Chuan-Xi , Lin Feng , Lian Yang-Yun , Sun Bo-Hang , Zhong Guo-Yue
Published: March 2019

Two new isocoumarin derivatives, talaisocoumarins A (1) and B (2), and three new related metabolites, talaflavuols A-C (3-5) were isolated from the wetland soil-derived fungus Talaromyces flavus BYD07-13. Their structures were elucidated by spectroscopic (NMR) and MS analyses. The absolute configurations of 1 and 2 were determined by CD and an Rh2(OCOCF3)4-induced CD method. All compounds were evaluated for cytotoxic and antimicrobial activities. However, none of them showed any activity. The plausible biosynthetic pathways for 1-5 were also proposed.
New Phenyl Propanoids from Cryptocarya bracteolata
Authors: Saidi Nurdin , Morita Hiroshi , Litaudon Marc , Naflah Mohd. Azlan , Awang Khalijah , Mustanir
Published: March 2019

Two new phenyl propanoids were extracted from the bark of Cryptocarya bracteolate Gamb., ethyl 3-(2′-hydroxy-3′,4′,5′-trimethoxyphenyl) propanoate (1) and ethyl 3-(2′-glucosyl-3′,4′,5′-trimethoxyphenyl)propanoate(2), together with seven known alkaloids, (+)-lirioferine (3), (+)-bracteoline (4), (+)-reticuline (5), (+)-reticulineN-oxide (6), (-)-norargemonine (7), (+)-bisnorargemonine (8) and atherolin (9). The structures of compounds were established through several spectroscopic methods; ID and 2D-NMR, UV, IR and MS.
Anti-inflammatory Constituents from the Aerial Parts of Iris minutiaurea
Authors: Woo Kyeong Wan , Lee Ki Ho , Jang Ji Hun , Kim Min Suk , Cho Hyun Woo , Cho Jung Hee , An Byeongkwan
Published: March 2019

Phytochemical investigation of the methanol extract of the aerial parts of Iris minutiaurea (Iridaceae) using column chromatography led to the isolation of a new xanthone glycoside, 1-hydroxy-3,5-dimethoxy-xanthone-6- O-β-D-glucoside (1), together with one known flavonoid glycoside (2). The structure of this new compound was elucidated by analysis of spectroscopic, including ID (1H, 13C), 2D NMR (COSY, HMQC, HMBC), and high resolution fast atom bombardment mass spectrometric (HR-FAB-MS) data and enzyme hydrolysis. We found that compounds 1 and 2 significantly suppressed production of NO, and pro-inflammatory cytokine in LPS-induced RAW264.7 cells. These results suggest that compound 1 and 2 have anti-inflammatory activity related with production of TNF-α, IL-6, IL-β, and NO in macrophages, and then compound 1 were more efficient than compound 2 in lowering the level of proinflammatory cytokine.
A Pair of New Polyketide Enantiomers from Three Endolichenic Fungal Strains Nigrospora sphaerica, Alternaria alternata, and Phialophora sp
Authors: He Jun-Wei , Wang Chuan-Xi , Yang Li , Chen Guo-Dong , Hu Dan , Guo Liang-Dong , Yao Xin-Sheng , Gao Hao
Published: March 2019

A pair of new enantiomeric polyketides, (-)- and (+)-nigrosporaol A (1a and 1b), along with one related known compound, (±)-alternarienoic acid (2), were isolated from three endolichenic fungal strains, Nigrospora sphaerica (No.83-1-1-2), Alternaria alternata (No.58-8-4-1), and Phialophora sp.(No.96-1-8-1). Their structures, including the absolute configurations, were elucidated on the basis of spectroscopic methods, X-ray diffraction analysis, and the modified Mosher's method.
Two New Isomers of Palmityl-4-hydroxycinnamate from Flowers of Taraxacum Species
Authors: Dudáš Matej , Vilková Mária , Béres Tibor , Repčák Miroslav , Mártonfi Pavol
Published: March 2019

Two isomers, (Z)- and (E)-palmityl 4-hydroxycinnamate [hexadecyl(2Z)-3-(4-hydroxyphenyl)prop-2-enoate and hexadecyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate] were isolated for the first time from ligulate flowers of Taraxacum linearisquameum Soest (sect. Taraxacum). The highest amount of these compounds was detected in pollen grains; 0.26 mg/100 mg DW of the (E)-isomer and 0.096 mg/100 mg DW of the (Z)-isomer. The structures of these compounds were elucidated by a combination of HPLC-ESI-Qtof-MS and ID and 2D NMR spectroscopy. Their presence was confirmed in other species of Taraxacum, but they were not found in the male-sterile triploid agamospermous taxon T. parnassicum.
Effects of Plant Density on the Number of Glandular Trichomes and on Yield and Quality of Essential Oils from Oregano
Authors: Tuttolomondo Teresa , La Bella Salvatore , Leto Claudio , Bonsangue Giuseppe , Leone Raffaele , Gennaro Maria Cristina , Virga Giuseppe , Inguanta Rosalinda , Licata Mario
Published: March 2019

Plants yields are influenced by agronomic techniques. Plant density is a complex issue and extremely important when maximizing both crop quality, and biomass and essential oil yields. Plants belonging to the Origanum vulgare subspecies hirtum (Link) Ietswaart were grown adopting four types of plant density and were characterized in biometric and chemical terms. The samples were analyzed using the ANOVA (Principal Component Analysis) statistical method regarding biometric aspects, EO yield and peltate hair density. Essential oil (EO) was extracted by hydrodistillation and analyzed using GC-FID and GC-MS. GC-FID and GC-MS analysis led to the identification of 45 compounds from the EO. Plant density affected production both in terms of biomass and EO. However, it was not found to have affected peltate glandular trichome density or EO quality.
In Vitro Trials of Dittrichia graveolens Essential Oil Combined with Antibiotics
Authors: Miladinović Dragoljub L. , Ilić Budimir S. , Kocić Branislava D. , Marković Marija S. , Miladinović Ljiljana C.
Published: March 2019

The chemical composition and antibacterial activity of Dittrichia graveolens (L.) Greuter essential oil were examined. Gas chromatography and gas chromatography/mass spectrometry were used to analyze the chemical composition of the essential oil. The antibacterial activity was investigated by the broth microdilution method against thirteen bacterial strains. The interactions of the essential oil and three standard antibiotics: chloramphenicol, tetracycline and streptomycin toward five selected strains were evaluated using the microdilution checkerboard assay in combination with chemometric methods: principal components analysis and hierarchical cluster analysis. Oxygenated monoterpenes were the most abundant compound class in the essential oil (40.6%), with bornyl acetate (21.7%) as the major compound. The essential oil exhibited slight antibacterial activity against the tested bacterial strains in vitro, but the combinations D. graveolens essential oil-chloramphenicol and D. graveo/ens-tetracycline exhibited mostly synergistic or additive interactions. These combinations reduced the minimum effective dose of the antibiotics and, consequently, minimized their adverse side effects. In contrast, the association of D. graveolens essential oil and streptomycin was characterized by strong antagonistic interactions against E. coli ATCC 25922, S. aureus ATCC 29213 and P. aeruginosa ATCC 27853. In the principal components analysis (PCA) and hierarchical cluster analysis (HCA), streptomycin against these bacterial strains stood out and formed a separate group.
Phytochemistry, Bioactivity and Potential Impact on Health of Juglans: the Original Plant of Walnut
Authors: Bi Dongdong , Zhao Yicheng , Jiang Rui , Wang Yan , Tian Yuxin , Chen Xiaoyi , Bai Shaojuan , She Gaimei
Published: March 2019

Walnuts are seeds with a hard shell from the genus Juglans (J. mandshurica, J. regia, J. sinensis, J. cathayensis, J. nigra and J. sigillata). Walnuts can nourish brain cells to improve human memory. Other parts of the plant are also employed as traditional Chinese medicines. Modern research on Juglans species has been mostly focused on the above-mentioned species, the seeds of which are all called walnuts. Juglans species have diverse chemical constituents, including diarylheptanoids, quinones, polyphenols, flavones and terpenes. The diarylheptanoids and quinones have notable antitumor activity, supplying new lead compounds for preparing antitumor drugs. The potent pain-relieving, antioxidant, antibacterial and antitumor activities of these plants are significant. In the review, comprehensive information on the nutritional characteristics, traditional functions, chemical constituents, and biological activities of the Juglans species, together with the seeds used as walnuts is provided to explore their potential and to advance research.
Dipasperoside B, a New Trisiridoid Glucoside from Dipsacus asper
Authors: Li Feng , Tanaka Ken , Watanabe Shiro , Tezuka Yasuhiro
Published: March 2019

Dipasperoside B (1), isolated from the root of Dipsacus asper, was determined to be a first example of naturally occurring iridoid glucoside trimer with an unusual skeleton featuring oxaloacetic acid derived moiety coupled with a secoiridoid nucleus in the central part, on the basis of spectroscopic data. Dipasperoside B (1) revealed the inhibitory activity against nitric oxide (NO) production in a lipopolysaccharide (LPS)-activated murine macrophage RAW264.7 cell line, with an IC50 value of 21.3 μM, identical to a positive control, NG-monomethyl-L-arginine (L-NMMA, IC50 22.6 μM), without any significant cytotoxicity.
Two New Lobane Diterpenes from a Bornean Soft Coral Sinularia sp
Authors: Phan Chin-Soon , Ng Shean-Yeaw , Kamada Takashi , Vairappan Charles Santhanaraju
Published: March 2019

Two new lobane diterpenoids, prenyl-α-elemenone (1) and ent-prenyl-β-elemene (2), along with a known compound, α-murrolene (3) were isolated from a population of Bornean soft coral Sinularia sp. The structures of these compounds were elucidated on the basis of spectroscopic, including 2D NMR, and HR-MS data. These compounds were tested for their cytotoxicity and antibacterial activities against antibiotic resistant clinical strains.
Three New Eremophilanes from a Ligularia Hybrid Collected in China
Authors: Saito Yoshinori , Takashima Yuriko , Okamoto Yasuko , Gong Xun , Hanai Ryo , Kuroda Chiaki , Tori Motoo
Published: March 2019

Three new eremophilanes were isolated from a sample of Ligularia collected in Yunnan province of China and their structures were determined. The chemical constituents including eleven eremophilanes (major constituents: 6-acyloxyfuranoeremophilan-10β-ols) were similar to those of a hybrid of L. cyathiceps and L. subspicata, however, the base sequence of the ITS1-5.8S-ITS2 region was typical of L. cyathiceps, indicating backcrossing.
Eudesmane Sesquiterpenoids from the Wood of Platycarya strobilacea
Authors: Morikawa Hitomi , Saito Yoshinori , Matsuo Yosuke , Maeda Hajime , Tanaka Takashi
Published: March 2019

The wood of Platycarya strobilacea Sieb. et Zucc. (Juglandaceae) was used as incense. In this study, three new sesquiterpenes (2, 4, 5) and one nor-sesquiterpene (3) were isolated and their structures determined as 7-hydroperoxy-11-hydroxy-2,4-cycloeudesman-8-one (2), 8-hydroxy-13-nor-2,4-cycloeudesman-7-en-11-one (3), 2,4-cycloeudesma-7(11), 8-dien-(12,8)-olide (4), and 8-hydroxy-8,12-peroxy-2,4-cycloeudesm-7(11)-ene (5). In addition, the absolute configuration of a previously reported sesquiterpene was revised based on the calculation of its ECD spectrum.
Triterpenoids from Schisandra propinqua var. propinqua
Authors: Liu Miao , Wan Jun , Luo Yuan-Qing , Li Xiao-Nian , Du Xue , Pu Jian-Xin , Sun Han-Dong
Published: March 2019

Four new triterpenoids, propindilactone T (1), propindilactone U (2), changnanic acid 3-methyl ester (3) and schipropinic acid (4), together with five known ones (5-9), were isolated and identified from the stems and leaves of Schisandra propinqua var. propinqua; their structures were determined based on spectroscopic and mass spectrometric analyses. The absolute configuration of 1 was confirmed by X-ray analysis. Compounds 1, 2, and 4-9 were tested for their cytotoxic activities against five human tumor cell lines; all were inactive except for 8, which showed weak activity against some of the cell lines.
Tirucallane Glycoside from the Leaves of Antidesma bunius and Inhibitory NO Production in BV2 Cells and RAW264.7 Macrophages
Authors: Trang Do Thi , Huyen Le Thi , Nhiem Nguyen Xuan , Quang Tran Hong , Hang Dan Thi Thuy , Yen Pham Hai , Tai Bui Huu , Anh Hoang Le Tuan , Binh Nguyen Quoc , Van Minh Chau , Van Kiem Phan
Published: March 2019

One new tirucallane- type triterpene glycoside, antidesoside (1), along with two biflavones, podocarpusflavone A (2) and amentoflavone (3) and two megastigmane glycosides, byzantionoside B (4), and (6 S,9 R)-roseoside (5) were isolated from the methanol extract of Antidesma bunius leaves. Their structures were determined by spectroscopic methods and in comparison with the published data. Compounds 1 - 3 were found to show strong inhibitory effect of NO production in BV2 cells and RAW264.7 macrophages LPS-stimulated, with IC50 values ranging from 8.5 to 26.9 μM.
Alkaloids from the Tuber of Stephania cf. rotunda
Authors: Le Duy Hoang , Nishimura Katsumi , Tanahashi Takao
Published: March 2019

Chemical investigation of the tuber of Stephania cf. rotunda collected in Vietnam led to the isolation of a new stephaoxocane-type alkaloid, stepharotudine (1), twenty-eight known alkaloids, and two known amides. The chemical structures of the isolated compounds were determined by spectroscopic and chemical methods. The absolute configuration of the new compound was determined from its CD spectrum and by 1H NMR analyses of its MPA esters. For the known alkaloids (-)-crebanine-β- N-oxide (2), uthongine (3), and palmatrubine (4), fully assigned NMR data are also reported for the first time.
Quantitative Determination of Principal Alkaloid and Flavonoid Constituents in Wintersweet, the Flower Buds of Chimonanthus praecox
Authors: Kitagawa Niichiro , Ninomiya Kiyofumi , Okugawa Shuhei , Motai Chiaki , Nakanishi Yusuke , Yoshikawa Masayuki , Muraoka Osamu , Morikawa Toshio
Published: March 2019

A quantitative analytical method has been developed for four alkaloids (1–4), identified as constituents responsible for the melanogenesis inhibitory activity of the extracts of wintersweet, the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae). Concurrently, a quantitative analytical protocol has been developed for five flavonoids (5–9), which also exhibited inhibitory activity. To approve the validity of the developed protocols, five extracts of the flower buds collected in Chinese market were evaluated. The optimum conditions of separation and detection of these alkaloids (1–4) and flavonoids (5–9) were achieved on a common ODS column using a MeOH-H2O mobile phase with different additives [Et2NH for alkaloids (1–4); acetic acid for flavonoids (5–9)]. The results indicated that these assays were reproducible and precise, and could be readily utilized for evaluation of the melanogenesis inhibitory activity of wintersweet on the basis of the content of the functional species. The principal flavonoid constituents (5–9) also exhibited lipid accumulation inhibitory activity.
A New Flavonol Triglycoside from Eustoma grandiflorum
Authors: Abe Naohito , Nakano Yuta , Shimogomi Aiko , Tanaka Toshiyuki , Oyama Masayoshi
Published: March 2019

A new flavonol triglycoside, kaempferol 3- O-α-L-rhamnopyranosyl (1→6)-(3- O- E- p-coumaroyl)-β-D-galactopyranoside-7- O-α-L-rhamnopyranoside (1: Eustograndifloside A) was isolated from the flower of Eustoma grandiflorum in addition to eight known flavonols (2: kaempferol 3- O-α-L-rhamnopyranosyl (1→6)-(4- O- E- p-coumaroyl)-β-D-galactopyranoside-7- O-α-L-rhamnopyranoside, 3: kaempferol 3- O-β-robinobioside-7- O-α-L-rhamnopyranoside, 4: isorhamne-tin 3- O-α-L-rhamnopyranosyl (1→2) [α-L-rhamnopyranosyl (1→6)]-(4- O- E- p-coumaroyl)-β-D-galactopyranoside-7- O-α-L-rhamnopyranoside, 5: kaempferol 3- O-α-L-rhamnopyranosyl (1→2) [α-L-rhamnopyranosyl (1→6)]-(4- O- E- p-coumaroyl)-β-D-galactopyranoside-7- O-α-L-rhamnopyranoside, 6: kaempferol 3- O-β-robinobioside, 7: quercetin 3- O-β-robinobioside, 8: isorhamnetin 3- O-β-robinobioside, and 9: kaempferol 7- O-α-L-rhamnopyranoside) and two known secoiridoid glycosides (10: swertiamarin and 11: sweroside). The structure elucidation of these compounds was accomplished through analyses of spectroscopic, including 1D and 2D NMR, and ESIMS data.
Ancistrotectoquinones A and B, the First Quinoid Naphthylisoquinoline Alkaloids, from the Chinese Liana Ancistrocladus tectorius
Authors: Bringmann Gerhard , Xu Minjuan , Seupel Raina , Feineis Doris , Wu Jun
Published: March 2019

From the leaves and stems of Ancistrocladus tectorius (Ancistrocladaceae) from the Chinese island Hainan, two novel-type 7,3′-coupled naphthylisoquinolines, named ancistrotectoquinones A (4) and B (5), were isolated. They are the first alkaloids with a 1,4-naphthoquinone portion coupled to an isoquinoline moiety. Due to the lowered degree of steric hindrance next to the biaryl axis and for electronic reasons, 4 and 5 occur as pairs of configurationally semi-stable, and, thus slowly interconverting atropo-diastereomers. The Gibbs free energies of activation between the two atropisomers of ancistrotectoquinone A (4a/b) were determined by measuring the time-dependent decrease of diastereomeric purity of freshly separated samples enriched with the M- or P-atropisomer and, computationally, by DFT calculations. The absolute configurations at the biaryl axes of the atropo-diastereomers of 4a/b and 5a/b were assigned by online LC-CD analysis. The stereostructure of 4a/b was further confirmed by its semi-synthesis from the likewise 7,3′-coupled ‘normal' naphthylisoquinoline alkaloid ancistrotectorine (6), by biomimetic oxidation with Fremy's salt.
Phellinus igniarius: A Pharmacologically Active Polypore Mushroom
Authors: Zapora Ewa , Wolkowycki Marek , Bakier Slawomir , Zjawiony Jordan K.
Published: March 2019

Mushrooms have been widely used in traditional medicine for the treatment of various diseases. Today, their therapeutic value is scientifically studied and appreciated. Research indicates that polypores - a large group of fungi of the phylum Basdiomycota - exhibit antiviral, antimicrobial, anticancer, anti-allergic, anti-atherogenic, hypoglycemic, hepatoprotective and anti-inflammatory activities. Phellinus igniarius, a polypore mushroom, is one of the most used in traditional Asian medicine. Its potent anticancer activity has been repeatedly reported. In the past two decades, numerous pharmacologically active metabolites have been isolated and identified from P. igniarius. Among the large number of compounds, the most active group are polysaccharides. They modulate immune responses and inhibit tumor growth.
Chemical and Genetic Study of two Ligularia Hybrids in Shangrila County, Yunnan Province, China
Authors: Hanai Ryo , Tanabe Sayako , Aoyama Nao , Okamoto Yasuko , Tori Motoo , Zhang Ningning , Gong Xun , Kuroda Chiaki
Published: March 2019

The composition of root chemicals was examined for samples of L. cyathiceps × L. duciformis, L. duciformis × L. yunnanensis, and L. yunnanensis. Various furanoeremophilanes were isolated from a sample of L. cyathiceps × L. duciformis and found to be very similar to those isolated from L. cyathiceps. Lupeol and docosyl ferulate were isolated from L. yunnanensis, L. duciformis, and L. duciformis × L. yunnanensis.
A Puna Collection of Senecio punae, Main Source of a Versatile Eremophilane-type Ketone
Authors: Rodríguez Ana María , Montanaro Susana , Bardón Alicia , Cartagena Elena , Borkosky Susana
Published: March 2019

Senecio punae Cabrera (Asteraceae-Senecioneae) is an endemic species from Puna semi-desert region of Argentina. The major compound, 4β,5β-eremophil-7(11)9-dien-8-one, also known as dehydrofukinone (D), was isolated from the diethyl ether extract (E) of the plant. The phytochemical constituents from S punae are presented here for the first time, as well as bioassays employing D, a molecule with versatility to carry out many different biological activities. E and D showed acute molluscicidal activity against the bilharzia vector snail Biomphalaria peregrina with LD50 values of 68.6 and 16.7 μg/mL, respectively. D exerted moderate and strong effects against promastigotes of Leishmania amazonensis and L. braziliensis, with IC50 values of 34.3±1.2 and 9.93±0.17 μg/mL, respectively. Antibacterial effects were also found. Diethyl ether extract (E) and dehydrofukinone (D) were slightly active against Pseudomonas aeruginosa and Staphylococcus aureus at 50 and 25 μg/mL, respectively. However, D and E improved the effectiveness of oxacillin at 6 μg/mL against S aureus growth and its biofilm, but did not affect beneficial lactobacilli strains. Synergistic effects were also measured between D (23 μg/mL) and ciprofloxacin (0.25 μg/mL) against two P. aeruginosa strains (FIC index = 0.38), as well as against two S aureus strains (FIC indexes = 0.38 and 0.25). Finally, when 250 μg of either dehydrofukinone (D) or diethyl ether extract (E) were incorporated into the diet of the pest Oryzaephillus surinamensis, an alteration in the feeding behavior of the insect (Repellency indexes = +60 and +10, respectively) was observed.
Cyclization into Hydrindanes Using Samarium Diiodide: Stereochemical Features Depending on the Protecting Group
Authors: Sono Masakazu , Nishibuchi Yukiko , Yamaguchi Norihito , Tori Motoo
Published: March 2019

Monocyclic compounds bearing ketone and enone moieties in the same molecule can be cyclized to bicyclic compounds initiated by samarium diiodide. The stereochemistry of the products depended on the reaction conditions and also the protecting group of the hydroxy group existed in the molecule. A cyclization mechanism is discussed.
Six New Triterpenoids from the Aerial Parts of Maytenus diversifolia
Authors: Anoda Narumi , Matsunaga Mayumi , Kubo Miwa , Harada Kenichi , Fukuyama Yoshiyasu
Published: March 2019

Five new ursane-type triterpenoids 1-5, and one new oleanane-type triterpenoids 7 were isolated from the MeOH extract of the aerial parts of Maytenus diversifolia. Their structures were elucidated by analyzing spectroscopic data and chemical transformation. Compounds 3 and 5 exhibited significant lethal activity in the brine shrimp lethality test (BST).
De novo Biosynthesis of Trigonelline in Fenugreek (Trigonella foenum-graecum) seedlings
Authors: Ashihara Hiroshi
Published: March 2019

The concentration of trigonelline in dry seeds of fenugreek ( Trigonella foenum-graecum) was 29±3 μmol/g fresh weight. Trigonelline occurred in cotyledons and embryonic axes of the seedlings, but it was found mainly in the above-ground parts of the young fenugreek plants. 15NH4+-feeding experiments suggest that the de novo biosynthesis of trigonelline from NH4+ occurs mainly in roots. Trigonelline, which is formed in roots using inorganic nitrogen, is transported to the stems and accumulates in leaves.
Estrogenic and Anti-estrogenic Constituents of Erythrina caffra
Authors: Hsu Yu-Ming , Lai Wan-Chun , Li Chi-Ying , Lan Yu-Hsuan , Tsai Yu-Chi , Hunyadi Attila , Hou Ming-Feng , Yuan Shyng-Shiou , Wu Yang-Chang , Chang Fang-Rong
Published: March 2019

Utilizing the pER8:GUS transgenic plant bioassay system to monitor estrogenic activity-guided fractionation, one new constituent, erycaffrain A, together with 11 known compounds were isolated from the ethanolic extract of Erythrina caffra. The structures of the isolated compounds were identified in combination with spectroscopic analyses. This is the first study reporting the estrogenic activity of E. caffra. The new compound exhibited as a SREM, but also showed both estrogenic and anti-estrogenic activities in the MCF-7 cancer cell model. Several known phytoestrogens in this plant also revealed possible new functions for E. caffra stem.
Development of an Efficient Protocol for Cimifugin Isolation from Peucedanum schottii and Evaluation of Enzyme Inhibitory Activity
Authors: Kozioł Ewelina , Orhan Ilkay Erdogan , Senol F. Sezer , Alipieva Kalina , Georgiev Milen , Skalicka-Woźniak Krystyna
Published: March 2019

The dichloromethane (DCM) extract of the fruits of Peucedanum schottii Besser ex DC. (Apiaceae) was subjected to high-performance counter-current chromatography (HPCCC) for the efficient and fast separation (30 min) and isolation of cimifugin using an ethyl acetate: water (1:1 v/v, K = 1.01) system. The analytical scale-optimized separation was easily scaled to semi-preparative conditions. Cimifugin (11.25% yield, 96.5% purity) was isolated for the first time from P. schottii and characterized by NMR spectroscopy. Cimifugin and the crude DCM extract were evaluated using ELISA microtiter assays for their inhibitory potential against the cholinesterases (acetylcholinesterase - AChE and butyrylcholinesterase - BChE), and tyrosinase (TYR), which are key enzymes for the treatment of some neurodegenerative diseases, i.e. Alzheimer's and Parkinson's. The crude extract exhibited a weak inhibitory activity against AChE, BChE, and TYR (4.2, 35.5, and 0% at 100 μg mL−1 and 10.3, 40.0, and 12.2% at 200 μg mL−1, respectively), while cimifugin displayed low to moderate inhibition towards AChE and BChE (3.1 and 21.6%, respectively) at 200 μg mL−1.
Lignans from the Whole Plants of Hedyotis uncinella
Authors: Pan Yaping , Zhang Yan , Fan Chao , Zhang Yu , Yan Shikai , Jin Huizi , Zhang Weidong
Published: March 2019

Two new lignans, named (7R, 8 S)-balanophonin (1) and (7R, 8 S)-tomentosanan A (2), together with eight known lignans, burselignan (3), (+)-isolariciresinol (4), (+)-lyoniresinol (5), 5-methoxy-(+)-isolariciresinol (6), (-)-syringaresinol (7), (+)-epipinoresinol (8), (-)-(7′ S, 8 S, 8′ R)-4,4′-dihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9-epoxy-lignan-9′-ol-7-one (9), and (-)-(7 R, 8 S)-dihydrodehydrodiconiferyl alcohol (10) were isolated from the whole plants of Hedyotis uncinella Hook. et Arn. Structures of these compounds were elucidated through 1H NMR, 13C NMR, 2D NMR, ESI-MS and CD data.
Biological Activities of Isolated Compounds from Three Edible Malaysian Red Seaweeds, Gracilaria changii, G. manilaensis and Gracilaria sp.
Authors: Andriani Yosie , Syamsumir Desy Fitrya , Yee Tee Ching , Harisson Faizah Shaharom , Herng Gan Ming , Abdullah Siti Aishah , Orosco Christine Abellana , Ali Abdul Manaf , Latip Jalifah , Kikuzaki Hiroe , Mohamad Habsah
Published: March 2019

Gracilaria species are red marine macroalgae that are found abundantly in Malaysia. Gracilaria changii from Morib, Selangor, G. manilaensis and Gracilaria sp. from Gelang Patah, Johor were used in this study. Five compounds were successfully isolated and identified as hexadecanoic acid (1), cholest-5-en-3-ol (2), 2-hydroxymyristic acid (3), cholesteryl myristate (4) and 1-(4'-methoxyphenyl)-3-(2”,4”,6”-trihydroxyphenyl)-3-hydroxypropanone (5) based on spectral data analysis (IR, UV, GC-MS, 1H NMR, 13C NMR, HMQC and HMBC). All compounds isolated were tested for cytotoxicity (MTT assay for HL-60 and MCF-7 cell lines), and antibacterial (disc diffusion method), antioxidant (DPPH free radical scavenging assay and xanthine oxidase inhibitory assay) and acetylcholinesterase inhibitory (AChE) activity (TLC bioautographic method). Compounds 1 and 3 exhibited strong cytotoxic activity against HL-60 and MCF-7 cell lines. Compound 5 showed high antioxidant activity in both the DPPH free radical scavenging and xanthine oxidase inhibition assays. Compound 1 showed positive activity for AChE inhibitory with a minimum inhibition dose of 0.625 μg sample. All compounds demonstrated antibacterial activity producing 8 to 14 mm inhibition zones. A positive control was applied to all bioassays and experiments were performed with three replicates. Results demonstrated that three edible red seaweeds are rich sources of bioactive compounds with potential application for pharmaceutical purposes.
Optical Resolution of (RS)-Denopamine to (R)-Denopamine β-D-Glucoside by Glucosyltransferase from Phytolacca americana Expressed in Recombinant Escherichia coli
Authors: Hamada Hiroki , Okada Shouta , Shimoda Kei , Uesugi Daisuke , Hamada Hatsuyuki
Published: March 2019

The optical resolution of racemic compounds by stereoselective glucosylation was investigated using plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. The glucosyltransferase glucosylated chemoselectively the phenolic hydroxyl group of phenol compounds. The ( R)-stereoselective glucosylation of ( RS)-denopamine by glucosyltransferase occurred to give ( R)-denopamine β-D-glucoside.
Macrocyclization Using RCM Reactions. Synthesis of Simple Metacyclophanes and Synthetic Efforts toward Platycarynol, a 15-Membered Aromatic Ether
Authors: Nakashima Katsuyuki , Matsunaga Hatsuna , Ito Masako , Minami Hiroshi , Aiba Akihito , Fujisaki Norihiro , Tori Motoo
Published: March 2019

Preparation of 13- to 19-membered carbocycles (metacyclophanes) from 1,3-disubstituted benzene derivatives has been successfully carried out using the RCM reaction, but similar starting materials having diphenyl ether did not cyclize to 15-membered compounds, whose ground state conformations were calculated and discussed. Several attempts to cyclize to form platycarynol are described.
Two Novel Diphenolic Metabolites from the Inedible Mushroom Thelephora palmata
Authors: Nishio Ayako , Mikami Haruka , Imagawa Hiroshi , Hashimoto Toshihiro , Tanaka Masami , Ito Takuya , Iguchi Miki , Iseki Kanako , Noji Masaaki , Umeyama Akemi
Published: March 2019

During the search for bioactive secondary metabolites, thelepalmatins A and B (1 and 2) were isolated from the fresh fruiting bodies of Thelephora palmata, together with four known compounds (3-6). Their structures were elucidated using MS analyses, and extensive 2D-heteronuclear NMR data interpretation. Compounds 3, 4 and 6 showed antimicrobial activities against Staphylococcus aureus and Bacillus subtilis with MIC values of 21.7-70.4 μM.
Analysis of Carotenoids, Flavonoids and Essential Oil of Calendula officinalis Cultivars Growing in Estonia
Authors: Raal Ain , Orav Anne , Nesterovitsch Julia , Maidla Kerttu
Published: March 2019

Pot Marigold (Calendula officinalis L.) is an annual ornamental plant with yellow to orange flowers which belongs the the Asteraceae family, its flowers are used in the pharmaceutical, cosmetic and food industries. The commercial samples of seeds (n=24) of C officinalis were cultivated in home gardens in Estonia. Total carotenoid contents, determined spectrophotometrically (λ=455 nm) in the inflorescences, varied from 0.7 to 2.7%, the cultivar with the highest carotenoid content was ‘Dracon’. The total content of flavonoids, determined spectrophotometrically (λ=370 nm), varied from 0.8% to 1.7%. The best cultivar contained almost maximum amount of total carotenoids (2.5%) and flavonoids (1.7%) was ‘Radio”. The oil yields of eight cultivars of C officinalis obtained were from 0.10 to 0.43%, the highest yield (0.43%) of the oil was obtained from the cultivar ‘Double Ball’. A total 70 compounds were identified and analysed by GC-MS in the essential oil of C officinalis, representing over 95% from total oil. The major components of the oils (>5%) of C. officinalis cultivars were α-cadinole (18.4-32.0%), γ-cadinene (9.7-18.9%), viridiflorol (2.0-10.0%), τ-cadinole (4.7-7.9%), δ-cadinole (3.3-5.6%), and γ-muurolene (0.8-5.1%). There is no clear relation between the colour of the inflorescences of C. officinalis and the total content of flavonoids and carotenoids. The chemotypes of essential oils of C. officinalis were not found among the cultivars studied.
Composition and Chemical Variability of the Cone Oil from Algerian Tetraclinis articulata
Authors: Boussaïd Maghnia , Bekhechi Chahrazed , Atik-Bekkara Fewzia , Paoli Mathieu , Casanova Joseph , Tomi Félix
Published: March 2019

Very little is known about the yield and chemical composition of the essential oil isolated from cones of Tetraclinis articulata (Vahl) Masters (Cupressaceae). In continuation of our on-going work devoted to the valorisation of medicinal and aromatic plants from Tlemcen Province (North-Western Algeria), cones have been harvested in eight locations (coastal township and highlands) and 40 oil samples have been isolated by hydrodistillation. Six oil samples were analyzed by a combination of chromatographic [GC(Retention indices)] and spectroscopic techniques (GC-MS, 13C NMR). Then, the remaining 34 oil samples were analyzed by [GC(RI)] and 13C NMR and the 40 compositions were submitted to statistical analysis. Essential oil yields varied substantially from sample to sample (0.17 to 1.13%, w/w). The cone oils consisted mainly of monoterpenes, with α-pinene (47.1-73.6%) and limonene (6.5-21.9%) being the main components. (E)-β-Caryophyllene and germacrene D were the major sesquiterpenes. Diterpenes, ( Z) and ( E)-biformene were identified for the first time in T. articulata essential oil. PCA analysis of the data allowed the distinction of two groups, the second group being sub-divided into two sub-groups. Groups and sub-groups were differentiated with respect to their contents of α-pinene and limonene and, to a lesser extent, of sesquiterpenes.
Enhancement of Pentobarbital-induced Sleep by the Vaporized Essential Oil of Citrus keraji var. kabuchii and its Characteristic Component, γ-Terpinene
Authors: Kobayashi Yoshinori , Takemoto Hiroaki , Fu Ziqi , Shimizu Emiko , Kinjo Yukitaka
Published: March 2019

Kabuchii (Citrus keraji var. kabuchii hort. ex Tanaka, Rutaceae) is a peculiar Okinawan citrus fruit. Local farmers cultivating various Citrus fruits say that the fragrance of Kabuchii is the most relaxing, but, there are few reports on the biological effects of the essential oil of Kabuchii and its chemical components [1]. In this study, the sedative effects of inhalation of the vaporized Kabuchii essential oil in open field, Rotarod, and pentobarbital sleep tests are compared with diazepam, as a positive control. In the open field test, both Kabuchii essential oil and diazepam decreased the spontaneous motor activity dose-dependently. The reduction in spontaneous motor activity in the 0.3 mg/cage (ca. 0.0278 mg/L) Kabuchii essential oil group was greater than that in the 1 mg/kg diazepam group. In the Rotarod test, Kabuchii did not affect the motor performance, even at the highest dosage tested (3 mg/cage), whereas diazepam decreased it dose-dependently. The effects of the major or characteristic components of Kabuchii, d-limonene, γ-terpinene, thymol, and p-cymene, were also evaluated in the open field and Rotarod tests. γ-Terpinene and thymol significantly decreased spontaneous motor activity at a dosage of 0.3 mg/cage, without affecting motor performance. Thus, γ-terpinene was estimated to be the main active component. Reduction in spontaneous motor activity by γ-terpinene in the open field test was not observed in intranasal zinc sulfate irrigation-induced anosmic mice. In the pentobarbital sleep test, both Kabuchii essential oil and diazepam potentiated pentobarbital-induced loss of the righting reflex (LRR). The LRR duration prolonging effects of both treatments were inhibited by pretreatment with flumazenil, a benzodiazepine receptor antagonist. The LRR latency reducing effect of Kabuchii was not affected by flumazenil, while that of diazepam was suppressed by it. γ-Terpinene showed similar potentiating effects on pentobarbital-induced sleep. Thus, vaporized Kabuchii essential oil and its active component, γ-terpinene, have sedative effects comparable with diazepam without inducing motor incoordination, which is a well-known side effect of diazepam.
Research Progress on Natural Benzophenanthridine Alkaloids and their Pharmacological Functions: A Review
Authors: Han Na , Yang Zhiyou , Liu Zhihui , Liu Huijing , Yin Jun
Published: March 2019

Benzophenanthridine alkaloids belong to the benzyl isoquinoline family of alkaloids, which are mainly found in Papaveraceae and Rutaceae. To date, over 100 compounds have been isolated from natural herbal medicines which display a variety of pharmacological functions. In this paper, we have summarized the work since 1980 and our own research on benzophenanthridine alkaloids in terms of their chemical structures and distribution, biosynthesis, biotransformation and metabolism, spectral characteristics, pharmacological activities and toxicity. This review lays the foundation for further research into benzophenanthridine alkaloids and their potential applications.
Dinitrosyl Iron Complexes and other Physiological Metabolites of Nitric Oxide: Multifarious Role in Plants
Authors: Shumaev Konstantin B. , Kosmachevskaya Olga V. , Chumikina Ludmila V. , Topunov Alexey F.
Published: March 2019

This review considers dinitrosyl iron complexes (DNICs) and some other metabolites of nitric oxide (NO) in plants. Nitric oxide is vital for all living organisms, although its role in plants has been studied insufficiently compared with that in animals. We presume that the spectrum of its functions in plants is even wider than in animals. The main NO metabolites could be S-nitrosothiols, DNICs and peroxynitrite. Of particular interest are pro- and antioxidant properties of these compounds. DNICs function and their potential biosynthetic role in plants are practically unknown and brought to the limelight in this review. Since the process of NO biosynthesis in plants is still under discussion, we also specially examine this problem.
Promising Anti-Hepatitis C Virus Compounds from Natural Resources
Authors: Wahyuni Tutik Sri , Utsubo Chie Aoki , Hotta Hak
Published: March 2019

Hepatitis C virus (HCV) infection is a major worldwide problem, which involves approximately 170 million people. High morbidity of patients is caused by chronic infection, which leads to liver cirrhosis, hepatocellular carcinoma and other HCV-related diseases. The sustained virological response (SVR) has been markedly improved to be >90% by the current standard interferon (IFN)-free treatment regimens with a combination of direct-acting antiviral agents (DAAs) targeting the viral NS3 protease, NS5A multi-function protein and NS5B RNA-dependent RNA polymerase, compared with 50–70% of SVR rates achieved by the previous standard IFN-based treatment regimens with or without an NS3 protease inhibitor. However, the emergence of DAA-resistant HCV strains and the limited access to the DAAs due to their high cost could be major concerns. Also, the long-term prognosis of patients treated with DAAs, such as the possible development of hepatocellular carcinoma, still needs to be further evaluated. Natural resources are considered to be good candidates to develop anti-HCV agents. Here, we summarize anti-HCV compounds obtained from natural resources, including medicinal plant extracts, their isolated compounds and some of their derivatives that possess high antiviral potency against HCV.
Neural Transmission from Oropharyngeal Bitter Receptors to the Medulla is Partially or Completely Labelled-Line
Authors: McMullen Michael K
Published: March 2019

The ground breaking advances in taste cell receptor cell physiology over the last 20 years have established a functional basis which enables neural pathways to be mapped. There is only one, or perhaps several, types of taste receptors for salt, sour, sweet and umami (meaty) tastes and stimulation of each receptor type elicits responses in different cognitive regions. These findings support the labelled-line neural pathway model. In contrast, there are 25 types of the bitter taste receptors which all produce the same cognitive sensation, a finding which supports the across-fiber pattern model. This paper compiles the findings of several human studies investigating the impact of bitter tastants on postprandial hemodynamics, to demonstrate that diverse bitter tastants are capable of eliciting a range of characteristic reflex cephalic phase responses in the autonomic and cardiovascular systems. These findings indicate that neural pathways from the oropharyngeal bitter taste receptors to the nucleus of the solitary tract are either partially or completely labelled-line. Consequently, the hedonics of a bitter tastant are not an accurate indicator of the cephalic phase responses elicited by the tastant. The finding that secondary metabolites present in dietary condiments modulate autonomic activity and in particular postprandial hemodynamics is novel and adds a new dimension to our understanding of the ways in which humans are influenced by their diet, both in health and disease. These findings suggest that condiments play a role in food digestion, unrelated to their hedonistic qualities. Consequently, condiments may be of significance to those with digestive disorders and especially for diabetics experiencing gastroparesis and/or postprandial hypotension. Additionally, the findings suggest a noninvasive method to assess the integrity of multiple neural pathways. For investigators exploring the effect of condiments on autonomic reflexes, traditional cuisines may be a valuable source as they are full of uncharted human recordings.
A Computational Examination of the Uncatalyzed Meinwald Rearrangement of Monoterpene Epoxides
Authors: Setzer William N.
Published: March 2019

Epoxides are relatively reactive compounds and may undergo decomposition or rearrangement reactions at elevated temperatures, and gas chromatographic analysis of essential oils may cause thermal decomposition or rearrangement of epoxide components at gas chromatographic temperatures. Density functional theory (DFT) calculations were carried out using the B3LYP functional at the 6-311++G**//6-31G* level of theory on the Meinwald rearrangements of α-pinene oxide (two different mechanisms leading to trans-pinocamphone and α-campholenal), cis-limonene oxide (leading to trans-dihydrocarvone), trans-limonene oxide (leading to cis-dihydrocarvone), 6,7-epoxymyrcene (leading to 2-methyl-6-methylene-7-octen-3-one), and 1,2-epoxy-2,5-dimethyl-3-vinyl-4-hexene (two mechanisms leading to 5-methyl-3-vinyl-4-hexenal and 8-methyl-5,7-nonadien-2-one). Free energies of activation for the uncatalyzed Meinwald rearrangement of common monoterpene epoxides are relatively large, being of the order of 70 kcal/mol, and are, therefore, not predicted to be important reactions at gas chromatographic temperatures.
Harpagoside Content in Devil's Claw Extracts
Authors: Kondamudi Narasimharao , Turner Matthew W. , McDougal Owen M.
Published: March 2019

Devil's claw is a common ingredient in nutraceutical products for the treatment of inflammation due to arthritis. The secondary root extract of Harpagophytum procumbens contains bioactive iridoid glycosides known as harpagosides. Recent scrutiny of the nutraceutical industry claims that products listing devil's claw on their labels should refer only to H. procumbens, while the closely related, and less expensive, H. zeyheri is not to be classified as devil's claw. This assertion is in contrast to botanists who claim that either species of Harpagophytum can be generically referred to as devil's claw. The current research aimed to determine the chemical composition of extracts from H. procumbens and H. zeyheri, with the intent to identify whether the bioactive harpagosides were similarly present between species, and how their presence resembled or deviated from commercially available H. procumbens extracts commonly used in nutraceutical products. A microwave extraction followed by high performance liquid chromatography analysis of root samples from botanical specimens of H. procumbens and H. zeyheri identified similar quantities of harpagoside, regardless of species. The chemical composition between root extracts for each species was found to contain varying quantities of non-harpagoside constituents, however their harpagoside content was comparable. These findings are intended to inform policymakers, nutraceutical manufacturers, and the general public of the distinction between myth and reality regarding devil's claw supplements.
A Study on the Lipase-catalysed Acylation of 6,7-Dihydroxy-linalool
Authors: Serra Stefano , De Simeis Davide
Published: March 2019

We here describe a study of the enzyme-mediated acylation reaction of 6,7-dihydroxy-linalool stereoisomers, which are natural triols occurring in different vegetal species. We found that only few lipases are able to catalyze the acylation of the secondary hydroxy group present in these isomers and only lipase from Candida rugosa and novozyme 435 provide either (3 R,6 R)-6-acetoxy-7-hydroxylinalool or (3 R,6 S)-6-acetoxy-7-hydroxylinalool in moderate and very good isomeric purity, respectively Even for these favorable cases the reaction proceeds very sluggishly. Our finding can give a sensible interpretation to the fact that 6-acyl-7-hydroxy-linalool derivatives do not occur in nature, whereas the corresponding glycosides, whose formation is catalyzed by glycosidase, are very common.
Germacrene Analogs are Anti-androgenic on Androgen-dependent Cells
Authors: Srivilai Jukkarin , Khorana Nantaka , Waranuch Neti , Wisuitiprot Wudtichai , Suphrom Nungruthai , Suksamrarn Apichart , Ingkaninan Kornkanok
Published: March 2019

Anti-androgenic drugs are treatments for androgen-related disorders such as benign prostatic hyperplasia, acne, hirsutism, and androgenic alopecia. Germacrone (1), a sesquiterpene isolated from hexane extracts of Curcuma aeruginosa Roxb. rhizome, is an androgen inhibitor of steroid 5-alpha reductase in-vitro. Here, we used the similarity of germacrone's α,ß-unsaturated carbonyl to testosterone's α,ß-unsaturated carbonyl to find germacrene analogs obtained from this plant and by semi-synthesis that might be more potent steroid 5-alpha reductase inhibitors. 8-Hydroxy germacrene B (4) was ~13-fold more potent than its parent, 1 and the most potent (IC50, 0.15±0.022 mM) among 9 compounds tested. The conformation of its cyclodecadiene ring and the α,ß-unsaturated ketone/hydroxy in the germacrene molecule might be crucial role for its anti-androgen activity. Moreover, 1 and 4 showed mild cytotoxic effect on prostate cancer cells. Neither compound was cytotoxic towards human dermal papilla cells at 100 μg/mL. We show that this SAR strategy created promising anti-androgenics for androgen dependent disorders and may create further analogues with further improvements in selectivity and clinical efficacy.
Terpenoids from the Fermented Broths of Coprinellus radians
Authors: Lee Ming-Shian , Hsiao Che-Jen , Ju Yu-Ming , Kuo Yueh-Hsiung , Lin Ruo-Kai , Lee Tzong-Huei
Published: March 2019

One new sesquiterpenoid, namely coprinol (1), along with guanacastanes J (2), E (3) and N (4), were isolated from the ethyl acetate extracts of the fermented broths of the fungal strain Coprinellus radians#1168. Their structures were elucidated on the basis of spectroscopic data analysis. The growth inhibitory activities against A549 of 1-4 were evaluated, and only 4 exhibited moderate growth inhibitory activity with a GI50 value of 18.2 μM compared with fluorouracil (GI50 = 3.6 μM). All the compounds were also subjected to antifungal assay against Candida albicans ATCC 18804, C. albicans SC-5314, Cryptococcus neoformans ATCC 13690 and Saccharomyces cerevisiae ATCC 2345; all showed mild antifungal activity with MIC values of 128.0 μg/mL for 1-3 and 64.0 μg/mL for 4 in comparison with amphotericin B (MIC = 0.25 μg/mL) and ketoconazole (MIC = 1.0 μg/mL).
On the Allylic Oxidation of Ent-kaurenic Acid Methyl Ester with Lead Tetra-acetate
Authors: Rojas Julio , Aparicio Rosa , Usubillaga Alfredo
Published: March 2019

In this paper, results obtained upon treatment of the methyl ester of ent-kaur-16-en-19-oic acid (1b) with lead tetra-acetate under reflux in glacial acetic acid solution and an argon atmosphere are described. After 30 minutes reflux, GC-MS analysis of the product indicated the presence of three substances, the initial compound (1b, 7 %), the methyl ester of ent-kaur-16-en-15- O-acetyl-19-oic acid (2a, C23H30O4, 45 %), and its isomer, the methyl ester of ent-kaur-15-en-17- O-acetyl-19-oic acid (3a, 47 %). Flash chromatography over silica gel containing 20% AgNO3 yielded 2b (456 mg), which was identified by direct comparison with an authentic sample, and 3a (472 mg), whose structure was established by uni- and bi-dimensional NMR analysis. Hydrolysis of 3a with dry ammonia in MeOH yielded the methyl ester of ent-kaur-15-en-17-hydroxy-19-oic acid (3b, C21H32O3); treatment of this compound with chromic acid/pyridine complex rendered the aldehyde (4).