bluuebunny/crossref_metadata_2025 huggingface dataset:
Anti-inflammatory and Gastroprotective Properties of Hypericum Richeri Oil Extracts
Authors: Zdunić Gordana , Gođevac Dejan , Milenković Marina , Šavikin Katarina , Menković Nebojša , Petrović Silvana
Published: March 2019

Oil extracts of flowering tops of Hypericum richeri Vill. prepared in three different ways were evaluated for chemical composition, and Anti-inflammatory and Gastroprotective activities. An HPLC method was developed for determination of two dominant flavonoids, quercetin and I3,II8-biapigenin. The carrageenan-induced rat paw edema test was used for screening the antiinflammatory activity, while indomethacin-induced rat gastric mucosa damage test was used for evaluation of gastroprotective activity. The oil extract prepared by maceration with 96% ethanol, followed by extraction with sunflower oil by heating on a water bath, exhibited the highest antiinflammatory (38.4 %) and gastroprotective activities (gastric damage score of 0.9). The same oil extract had the highest content of quercetin (49 μg/mL) and I3,II8-biapigenin (60 μg/mL). These results approve the usage of oil extracts of H. richeri as an antiinflammatory and gastroprotective agent.
Anthraquinones from the Roots of Prismatomeris Tetrandra
Authors: Zhang Cun-Li , Guan Hua , Xi Peng-Zhou , Deng Tao , Gao Jin-Ming
Published: March 2019

A new anthraquinone compound, 1,3-dihydroxy-6-methoxy-2-methoxymethyl-9,10-anthraquinone (1), along with four known analogues (2–5) were isolated from the roots of Prismatomeris tetrandra. Their structures were elucidated on the basis of spectroscopic analysis. Among these compounds, lucidin ω-methyl ether (4) and lucidin ω-ethyl ether (5) were isolated from this genus for the first time. Compound 1 showed weak cytotoxic activity against A549 and LAC cell lines.
Volatile Compounds from Tagetes Pusilla (Asteraceae) Collected from the Venezuela Andes
Authors: Buitrago Diolimar , Rojas Luis B. , Rojas Janne , Morales Antonio
Published: March 2019

The essential oil from the leaves of Tagetes pusilla Kunth (Asteraceae) collected from Mérida, Venezuela, was analyzed by GC/MS. A yield of 0.38% oil was obtained by hydrodistillation. Only two components, trans-anethole and 4-allylanisole were identified by comparison of their mass spectra with those in the Wiley GC-MS Library data base.
Essential Oil Composition and In Vivo Volatiles Emission by Different Parts of Coleostephus Myconis Capitula
Authors: Flamini Guido , Cioni Pier Luigi , Maccioni Simonetta , Baldini Rosa
Published: March 2019

The essential oil obtained by hydrodistillation of the flowering capitula of Coleostephus myconis (syn. Chrysanthemum myconis) was constituted almost exclusively of oxygenated sesquiterpenes (85.8%). The main constituent was T-cadinol (66.2%), followed by valeranone (8.2%), germacrene D (6.0%) and α-cadinol (4.6%). By mean of the SPME technique, the volatiles emitted in vivo by the whole capitula and by tubular and ligulate florets have been identified. Many differences were evidenced among the different organs and with respect to the essential oil
The Influence of Essential Oils on Human Vigilance
Authors: Heuberger Eva , Ilmberger Josef
Published: March 2019

Olfactory stimuli are used in aromatherapy to enhance mood, well-being and work efficiency. Nevertheless, the impact of fragrances on cognitive performance in humans is not well understood. The present investigation aimed to evaluate the effects of 1,8-cineol, jasmine absolute ether, linalyl acetate and peppermint essential oil on human vigilance performance. The odorants were administered by means of inhalation and, except for peppermint essential oil, were tested at 2 different dosages. Performance in a standard visual vigilance task was measured in terms of speed and accuracy and subjective ratings of the odorants were assessed in terms of pleasantness, intensity, arousal and stress. We hypothesized that 1,8-cineol, jasmine absolute ether and peppermint essential oil would improve vigilance performance, whereas linalyl acetate would impair such performance. Comparison of the performances of the seven independent experimental groups with that of a control group did not show any of the expected effects. In contrast, inhalation of linalyl acetate decreased reaction times. Within-group analyses, however, revealed significant interactions between subjective ratings of the odorants and task performance. The results of the present investigation emphasize the high impact of subjective factors on the modulation of attentional functions by olfactory stimuli in humans.
Volatiles from Thymbra and Thymus species of the Western Mediterranean Basin, Portugal and Macaronesia
Authors: Figueiredo A. Cristina , Barroso José G. , Pedro’ Luis G.
Published: March 2019

Thyme is the common name of many taxa belonging to the Thymbra and Thymus genera. Given the economic importance of thyme oils, many thyme species have been studied and their essential oils and other volatile-containing extracts chemically characterized. Thymbra and Thymus species are frequent in the west Mediterranean region, considered to be the centre of origin of the genus Thymus, and extend further westwards in the Iberian Peninsula and northwest Africa, to the Macaronesian region in the Atlantic Ocean. The present work gives an overview of the chemical composition of the volatiles from the taxa of these two genera occurring in the above geographic area.
Essential Oil Composition of Wild Growing Apiaceae from Europe and the Mediterranean
Authors: Chizzola Remigius
Published: March 2019

In this overview, the essential oil composition of more than 150 species from about 50 genera of the Apiaceae is reviewed. Essential oil components encountered in Apiaceae proved to be very diverse; they include monoterpenes, sesquiterpenes, rarely diterpenes, phenylpropanoids, phthalides, octanol and octyl esters, trimethylbenzaldehydes and aliphatic aldehydes. In assessing the data one has to keep in mind that the essential oil amount and composition is influenced by many factors, including geographic and genetic variation, physiological aspects and environmental conditions. In some species the occurrence of chemotypes could be demonstrated, but in many cases the data available do not allow the evaluation of infraspecific variability.
Terpenoids from Turraeanthus species
Authors: Vardamides Juliette Catherine , Sielinou Valerie Tedjon , Akone Sergi Herve , Nkengfack Augustin Ephrem , Abegaz Berhanu M.
Published: March 2019

Chemical investigation of the root bark of Turraeanthus mannii and the stem of T. longipes resulted in the isolation of two new diterpenes, 13-methyl-labda-8(17)-en-15-oic acid (1) and 13-(hydroxymethyl)-14-hydroxy- ent-labda-8(17)-en-15-oic acid (2), along with two known diterpenes, 19-hydroxy- ent-labda-8(17),13-dien-15,16-olide (3) and 19-acetoxy- ent-labda-8(17),13-dien-15,16-olide (4), and the phytosterol, stigmasterol. The structure elucidation of the new compounds has been achieved using spectroscopic techniques.
Two Minor Phytoecdysteroids of the Plant Silene Viridiflora
Authors: Mamadalieva Nilufar Zokirzhonovna , Janibekov Abdulaziz Adilhanovich , Girault Jean-Pierre , Lafont René
Published: March 2019

Chemical investigations of Silene viridiflora (L.) yielded a new ecdysteroid, 20-hydroxyecdysone 20,22-monoacetonide-25-acetate (1), and a known ecdysteroid, 2-deoxypolypodine B-3-β-D-glucoside (2). The elucidation of the chemical structures was established by 1D and 2D NMR experiments.
Cytotoxicity of Constituents from Mexican Propolis against a Panel of Six Different Cancer Cell Lines
Authors: Li Feng , Awale Suresh , Tezuka Yasuhiro , Kadota Shigetoshi
Published: March 2019

The cytotoxicity of 39 compounds, including eighteen flavonoids (flavanones, 1–10; flavones, 11–17; flavanol, 18), sixteen phenolic acid derivatives (aromatic acids, 19–24; aldehyde, 25; esters, 26–34) and five glycerides (35–39), isolated from Mexican propolis, were evaluated against a panel of six different cancer cell lines; murine colon 26-L5 carcinoma, murine B16-BL6 melanoma, murine Lewis lung carcinoma, human lung A549 adenocarcinoma, human cervix HeLa adenocarcinoma and human HT-1080 fibrosarcoma. A phenylpropanoid-substituted flavanol, (2 R,3 S)-8-[4-phenylprop-2-en-1-one]-4’,7-dihydroxy-3’,5-dimethoxyflavan-3-ol (18), showed the most potent cytotoxicity against A549 cells (IC50, 6.2 μM) and HT-1080 cells (IC50, 3.9 μM), stronger than those of the clinically used anticancer drug, 5-fluorouracil (IC50, 7.5 μM and 5.4 μM, respectively). Based on the observed results, the structure–activity relationships are discussed.
Biodiversity of Volatile Organic Compounds from Five French Ferns
Authors: Fons Françoise , Froissard Didier , Bessière Jean-Marie , Buatois Bruno , Rapior Sylvie
Published: March 2019

Five French ferns belonging to different families were investigated for volatile organic compounds (VOC) by GC-MS using organic solvent extraction. Fifty-five VOC biosynthesized from the shikimic, lipidic and terpenic pathways including monoterpenes, sesquiterpenes and carotenoid-type compounds were identified. The main volatile compound of Adiantum Capillus-Veneris L. (Pteridaceae) was ( E)-2-decenal with a plastic or “stink bug” odor. The volatile profiles of Athyrium filix-femina (L.) Roth (Woodsiaceae) and Blechnum spicant (L.) Roth (Blechnaceae) showed similarities, with small amounts of isoprenoids and the same main volatile compounds, i.e., 2-phenylethanal (odor of lilac and hyacinth) and 1-octen-3-ol (mushroom-like odor). The main volatile compound of Dryopteris filix-mas (L.) Schott (Dryopteridaceae) was ( E)-nerolidol with a woody or fresh bark note. Polyketides, as acylfilicinic acids, were mainly identified in this fern. Oreopteris limbosperma (Bellardi ex. All.) J. Holub (Thelypteridaceae), well-known for its lemon smell, contained the highest biodiversity of VOC. Eighty percent of the volatiles was issued from the terpenic pathway. The main volatiles were ( E)-nerolidol, α-terpineol, β-caryophyllene and other minor monoterpenes (for example, linalool, pinenes, limonene, and γ-terpinen-7-al). It was also the fern with the highest number of carotenoid-type derivatives, which were identified in large amounts. Our results were of great interest underlying new industrial valorisation for ferns based on their broad spectrum of volatiles.
Essential Oil Polymorphism of Wild Growing Hungarian Thyme (Thymus Pannonicus) Populations in the Carpathian Basin
Authors: Pluhár Zsuzsanna , Sárosi Szilvia , Pintér Adrienn , Simkó Hella
Published: March 2019

The volatile oil compositions of Thymus pannonicus All. from nineteen different localities of Hungary were analyzed by GC/MS. The essential oil content of the Hungarian thyme samples varied between very low (0.14 mL/100 g DW) and fairly high (1.9 mL/100 g DW) values. Significant essential oil polymorphism was found: altogether twelve chemovarieties may have been determined, representing a way of adaptation to different habitat conditions. The main volatile compound of chemotype 1 was thymol (24.6-67.5%), while in the case of chemotype 2, thymol (36.5-63.7%) and p-cymene (11.5-27.3%) predominated. Thymol (28.4-63.7%), p-cymene (11.5-31.8%) and γ-terpinene (9.7-20.9%) were identified as the chief monoterpenes of chemotype 3, while chemotype 4 contained thymol (36.5%), p-cymene (27.3%) and neral (11.2%). Chemotype 5 accumulated thymol (38.5%), p-cymene (20.6%), γ-terpinene (12.0%) and β-bisabolene (10.3%) as its main volatiles. The oil of chemotype 6 can be characterized by thymol (41.9%), p-cymene (20.2%), isoborneol (10.3%) and γ-terpinene (9.9%), while that of chemotype 7 consisted of thymol (27.7%), linalyl acetate (18.8%), γ-terpinene (18.6%) and α-cubebene (13.9%). In the oil of chemotype 8, p-cymene (45.0%), geraniol (13.6%) and linalyl acetate (9.9%) were found in higher percentages, while chemotype 9 mainly produced linalyl acetate (36.2%) and geranyl acetate (20.2%). Chemotype 10 accumulated germacrene-D (43.4) and β-caryophyllene (15.0%), while the oil of chemotype 11 contained caryophyllene oxide (45.2%), α-cubebene (15.7%) and linalool (13.8%) in high proportions. Germacrene-D (29.7%), β-caryophyllene (22.0%) and farnesol (10.4%) were identified as main essential oil compounds of chemotype 12. The last nine chemotypes were new for the literature, while the first seven contained thymol as their chief compound. The role of certain sesquiterpenes was found to be considerable.
Straightforward Approach to the Discrimination of (4R)-and (4S)-β-Isocryptoxanthin from a Conformationally Insensitive CD Band
Authors: Hosoi Shinzo , Tanaka Takeyuki , Katsumoto Yukiteru , Maoka Takashi , Fujiwara Toshio , Yamashita Masayuki , Node Manabu
Published: March 2019

A straightforward strategy is reported for chiral discrimination in a specified carotenoid using a CD band, which is insensitive to conformational changes, computed by quantum chemical calculation.
New Steroidal Alkaloids from Solanum Hypomalacophyllum
Authors: Colmenares Alida Pérez , Alarcón Libia , Rojas Luis B. , Mitaine-Offer Anne-Claire , Pouységu Laurent , Quideau Stéphane , Paululat Thomas , Usubillaga Alfredo , Lacaille-Dubois Marie-Aleth
Published: March 2019

Two new steroidal alkaloids (1-2) have been isolated from the leaves and roots of Solanum hypomalacophyllum Bitter, respectively. Their structures have been elucidated as deacetoxysolaphyllidine-3- O-β-D-glucopyranoside (1) and 4-keto-5,6-dihydro-(20 S)-verazine (2). Furthermore, two known steroidal alkaloids, 20 R-verazine and 20 S-verazine, and the common secondary metabolites oleanolic acid and β-sitosterol were isolated from the roots, whereas deacetoxysolaphyllidine was obtained from the leaves.
Two new Diarylheptanoids from Alnus Nitida
Authors: Siddiqui Imran N. , Ahmad Viqar U. , Zahoor Aqib , Ahmed Amir , Khan Saleha S. , Khan Afsar , Hassan Zahid
Published: March 2019

Two new diarylheptanoids, trivially named nitidone A and nitidone B, have been isolated from Alnus nitida. The structure elucidation of the compounds was based primarily on 2D-NMR spectroscopic techniques and by comparison with literature data.
Pycnangloside: A New Cerebroside from Bark of Pycnanthus Angolensis
Authors: Tsaassi Valérie Béatrice , Hussain Hidayat , Tamboue Hélène , Dongo Etienne , Kouam Simeon F. , Krohn Karsten
Published: March 2019

Pycnanthus anglonensis is known for its medicinal value. This paper deals with a phytochemical investigation of this species, from which pycnangloside (1), a new cerebroside has been isolated. Its structure was determined by comprehensive analyses of its 1D and 2D NMR spectroscopic, and ESI mass spectrometric data. Four known compounds were also isolated and identified as biochanin A, formonentin, β-sitosterol, and β-sitosterol glucopyranoside.
Essential Oil of Turnera Ulmifolia Leaves from Cuba
Authors: Pino Jorge A.
Published: March 2019

The chemical composition of the volatile compounds from the leaves of Turnera ulmifolia L. (Turneraceae) from Cuba was studied by GC and GC/MS. Sixty-four volatile compounds were identified, of which the major ones were β-caryophyllene (21.5%) and ( Z)-3-hexen-1-ol (18.4%).
Antiplasmodial and Cytotoxic Activities of Drimane Sesquiterpenes from Canella winterana
Authors: Grace Mary H. , Lategan Carmen , Mbeunkui Flaubert , Graziose Rocky , Smith Peter J. , Raskin Ilya , Lila Mary Ann
Published: March 2019

The hexane extract from the leaves of Canella winterana exhibited strong activity against the chloroquine sensitive (CQS) strain of Plasmodium falciparum (D10) in vitro (IC50 2.53 μg/mL). Bioassay guided fractionation of this extract has led to the isolation of 5 drimane-type sesquiterpenoids: 9-epideoxymuzigadial, 9-deoxymuzigadial, muzigadial, 3-β-acetoxypolygodial and the newly isolated hemiacetal, named muzigodiol, with IC50-values of 1.01, 2.19, 0.31, 2.77 and 7.43 μg/mL, respectively. The first four compounds were tested for their cytotoxicity using Chinese Hamster Ovarian (CHO) cells, where they showed IC50-values of 1.82, 33.69, 1.18, and 58.31 μg/mL, respectively. A structure-activity relationship is discussed.
Fujianmycin C, A Bioactive Angucyclinone from a Marine Derived Streptomyces sp. B6219 [1]
Authors: Abdalla Muna Ali , Helmke Elisabeth , Laatsch Hartmut
Published: March 2019

From a marine-derived streptomycete, a new bioactive angucyclinone, fujianmycin C (1), has been isolated along with five known, metabolites fujianmycins A (2) and B (3), ochromycinone (4), ochromycinone methyl ether (5), and tetrangulol methyl ether (6). The structure elucidation of fujianmycin C (1) was performed by detailed analysis of data such as 1H, 13C, 1H,1H COSY, HSQC, HMBC and NOESY spectra. Fujianmycin C (1) exhibited antibacterial activity against Streptomyces viridochromogenes (Tü57).
Inhibition of Protein Tyrosine Phosphatase 1β by Hispidin Derivatives Isolated from the Fruiting Body of Phellinus linteus
Authors: Lee Yeon Sil , Kang Il-Jun , Won Moo Ho , Lee Jae-Yong , Kim Jin Kyu , Lim Soon Sung
Published: March 2019

Protein tyrosine phosphatase 1β (PTP1β) acts as a negative regulator of insulin signaling. Selective inhibition of PTP1β has served as a potential drug target for the treatment of type 2 diabetes mellitus. We evaluated the inhibitory effect of Phellinus linteus against PTP1β as part of our ongoing search for natural therapeutic and preventive agents for diabetes mellitus. Fractions of the P. linteus extract were found to exhibit significant inhibitory activities against PTP1β. In an attempt to identify bioactive components, we isolated, from the most active ethyl acetate fraction, five hispidin derivatives (phelligridimer A, davallialactone, hypholomine B, interfungins A, and inoscavin A) and four phenolic compounds (protocatechuic acid, protocatechualdehyde, caffeic acid, and ellagic acid). The chemical structures of these compounds were elucidated from spectroscopic evidence and by comparison with published data. All the compounds strongly inhibited PTP1β activity in an in vitro assay; their IC50 values ranged from 9.0 ± 0.01 to 58.2 ± 0.3 μM. Our results indicated that the hispidin skeleton may be an important moiety for inhibitory activity of the above compounds against PTP1β. Thus, hispidin derivatives could be a potent new class of natural PTP1β inhibitors.
A New Azafluorenone from the Roots of Polyalthia cerasoides and its Biological Activity
Authors: Pumsalid Kanchana , Thaisuchat Haruthai , Loetchutinat Chatchanok , Nuntasaen Narong , Meepowpan Puttinan , Pompimon Wilart
Published: March 2019

Chromatographic separation of the ethyl acetate extract of roots of Polyalthia cerasoides has led to the isolation of the new compound, 6,8-dihydroxy-7-methoxy-1-methyl-azafluorenone. This compound exhibited potent cytotoxic activities with IC50 values in the range of 2.64-3.58 μg.mL−1 for A549, GLC4 and GLC4/Adr cells, but was not recognized by ABCC1/MRP1 protein. The compound also showed very strong inhibition of M. tuberculosis using a broth microdilution method, with an MIC value of 0.78 μg.mL−1, which was equal to that of ofloxacin, one of the four antibiotic drugs used as a positive control.
Evaluation of Antiviral Activities of Curcumin Derivatives against HSV-1 in Vero Cell Line
Authors: Zandi Keivan , Ramedani Elissa , Mohammadi Khosro , Tajbakhsh Saeed , Deilami Iman , Rastian Zahra , Fouladvand Moradali , Yousefi Forough , Farshadpour Fatemeh
Published: March 2019

Antiviral drug resistance is one of the most common problems in medicine, and, therefore, finding new antiviral agents, especially from natural resources, seems to be necessary. This study was designed to assay the antiviral activity of curcumin and its new derivatives like gallium-curcumin and Cu-curcumin on replication of HSV-1 in cell culture. The research was performed as an in vitro study in which the antiviral activity of different concentrations of three substances including curcumin, Gallium-curcumin and Cu-curcumin were tested on HSV-1. The cytotoxicity of the tested compounds was also evaluated on the Vero cell line.

The CC50 values for curcumin, gallium-curcumin and Cu-curcumin were 484.2 μg/mL, 255.8 μg/mL and 326.6 μg/mL, respectively, and the respective IC50 values 33.0 μg/mL, 13.9 μg/mL and 23.1 μg/mL. The calculated SI values were 14.6, 18.4 and 14.1, respectively. The results showed that curcumin and its new derivatives have remarkable antiviral effects on HSV-1 in cell culture.
Hyloglyceride and Hylodiglyceride: Two New Glyceride Derivatives from Hylodendron gabunensis
Authors: Nyongha Awazi Tengu , Hussain Hidayat , Dongo Etienne , Ahmed Ishtiaq , Krohn Karsten
Published: March 2019

Phytochemical investigation of Hylodendron gabunensis resulted in the isolation of two new glyceride derivatives, hyloglyceride (1) and hylodiglyceride (2). The structures of the two new compounds were determined by comprehensive analysis of their 1D and 2D NMR spectroscopic, and HREIMS data. One known compound was also isolated and identified as β-sitosterol.
Essential Oil Yield and Chemical Composition Changes during Leaf Ontogeny of Palmarosa (Cymbopogon martinii var. motia)
Authors: Rao Bhaskaruni R. Rajeswara , Rajput Dharmendra K. , Patel Rajendra P. , Purnanand Somasi
Published: March 2019

Changes in leaf biomass yield, essential oil yield, and chemical composition were investigated during leaf ontogeny of palmarosa { Cymbopogon martinii (Roxb.) Wats. var. motia Burk., family Poaceae}. Eleven leaves representing different developmental stages, serially numbered from the apex to the base of the plant were utilized for the study. Leaf biomass yield increased up to the eighth leaf. Essential oil recovery increased up to the third leaf; thereafter it decreased. Minimum essential oil recovery was observed in the eleventh leaf. Essential oil yield/leaf increased up to the sixth leaf. Essential oil yield and concentrations of linalool, α-terpineol, geranyl isobutyrate and geraniol were relatively higher in the essential oils of mature, older leaves. Essential oil recovery, and percentages of myrcene, β-caryophyllene, geranyl acetate, ( E, Z) farnesol and geranyl hexanoate were higher in the essential oils of young, expanding leaves.
A New Megastigmane Glycoside, Phoenixoside A, from Phoenix Dactylifera
Authors: Azmat Sumbul , Zahoor Aqib , Ifzal Rehana , Ahmad Viqar Uddin , Mohammed Faryal Vali
Published: March 2019

A new megastigmane glycoside, phoenixoside A (1), has been isolated from the n-butanol - soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as (6S,7Z,9R)-hydroxy-3-oxo-ionol-9- O-β-D-glucopyranosyl-(1″→6′)-β-D–glucopyranoside on the basis of 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and CD spectroscopy.
Constituents of Kenyan Gardenia Volkensii
Authors: Kinuthia Esther W. , Langat Moses K. , Mwangi Elizabeth M. , Cheplogoi Peter K
Published: March 2019

A new triterpenoid, 3-oxo-22α-hydroxy-olean-12-en-28-oic acid (1), oleanolic acid (2) and a known iridoid, 10-hydroxy-1-oxo-7-iriden-11-oic acid methyl ester (3) have been isolated from the dichloromethane extract of the dried seeds of Gardenia volkensii. Their structures were established by 1D and 2D NMR spectroscopic and MS methods.
Oral Administration of Cimicifuga racemosa Extract Attenuates Immobilization Stress-Induced Reactions
Authors: Nadaoka Isao , Watanabe Kazuki , Yasue Masaaki , Sami Manabu , Kitagawa Yasushi , Mimaki Yoshihiro
Published: March 2019

Dried rhizomes of Cimicifuga racemosa (CR), known as black cohosh, have been widely used as a herbal dietary supplement in the treatment of menopausal symptoms. Here we used experimental mouse stress models to investigate the role of anti-stress food factors, and found that a CR extract had stress-relieving effects. A single oral administration of CR extract (1,000 mg/kg) significantly attenuated plasma corticosterone and aspartate aminotransferase (AST) levels that had increased as a result of enforced immobilization. Bioassay-guided fractionation of the CR extract resulted in the isolation of 10 triterpenes, among which actein, 23- epi-26-deoxyactein, and cimiracemoside F (100 mg/kg, per os) were shown to contribute to the anti-stress effects. Furthermore, the CR extract significantly prevented the development of water immersion stress-induced gastric mucosal ulcers in rats. We propose that the CR extract might be suitable for the prevention and treatment of stress-related disorders.
Diuretic Activity of Lophophytum leandri
Authors: Bracci Antonio , Amat Anibal G. , Maione Francesco , Cicala Carla , Mascolo Nicola , De Feo Vincenzo
Published: March 2019

A bioassay-oriented study was carried-out in order to validate the traditional uses of Lophophytum leandri, a parasitic plant used as a diuretic in traditional medical practices of Argentina. Four known flavonoids have been isolated from the active fraction. Quercetin-3- O-β-D-glucopyranoside was identified as the active principle of the fraction. However, the diuretic activity of the extract and of the most active fraction had greater activity than that of the pure isolated compounds.
Phytochemical Analysis and Antioxidant Capacity of BM-21, a Bioactive Extract Rich in Polyphenolic Metabolites from the Sea Grass Thalassia testudinum
Authors: Regalado Erik L. , Menendez Roberto , Valdés Olga , Morales Ruth A. , Laguna Abilio , Thomas Olivier P. , Hernandez Yasnay , Nogueiras Clara , Kijjoa Anake
Published: March 2019

The aqueous ethanol extract of Thalassia testudinum leaves (BM-21) is now being developed in Cuba as an herbal medicine due to its promising pharmacological properties. Although some interesting biological activities of BM-21 have already been reported, its chemical composition remains mostly unknown. Thus, we now describe the qualitative and quantitative analyzes of BM-21 using standard phytochemical screening techniques, including colorimetric quantification, TLC and HPLC analyses. Phytochemical investigation of BM-21 resulted in the isolation and identification of a new phenolic sulfate ester (1), along with ten previously described phenolic derivatives (2-11), seven of which have never been previously reported from the genus Thalassia. The structures of these compounds were established by analysis of their spectroscopic (1D and 2D NMR) and spectrometric (HRMS) data, as well as by comparison of these with those reported in the literature. Furthermore, BM-21 was found to exhibit strong antioxidant activity in four different free radical scavenging assays (HO•, RO2•, O2-• and DPPH•). Consequently, this is the first study which highlights the phytochemical composition of BM-21 and demonstrates that this product is a rich source of natural antioxidants with potential applications in pharmaceutical, cosmetic and food industries.
Xanthones with Antiproliferative Effects on Prostate Cancer Cells from the Stem Bark of Garcinia xanthochymus
Authors: Ji Feng , Li Zhanlin , Liu Gaofeng , Niu Shengli , Zhao Nan , Liu Xiaoqiu , Hua Huiming
Published: March 2019

Investigations of the constituents of the stem barks of Garcinia xanthochymus have yielded two new compounds, garcinenones X (1) and Y (2), along with five known xanthones, 1,4,5,6-tetrahydroxy-7-(3-methylbut-2-enyl)xanthone (3), 1,4,6-trihydroxy-5-methoxy-7-(3-methylbut-2-enyl)xanthone (4), 1,4,5,6-tetrahydroxy-7,8-di(3-methylbut-2-enyl)xanthone (5), 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methylbut-2-enyl)xanthone (6), and 1,5,6-trihydroxy-7,8-di(3-methylbut-2-enyl)-6′,6'dimethylpyrano(2′,3′:3,4)xanthone (7). The structures of the compounds were determined by spectroscopic methods. The cell growth inhibitory activity of the isolated compounds against the PC-3 cell line was measured. Among them, compounds 2, 3, 5, and 6 exhibited significant inhibitory effects with IG50 values of 14.3, 15.5, 11.1, and 6.8 μM, respectively.
Antibacterial Activities of Essential Oils Extracted from Leaves of Murraya koenigii by Solvent-Free Microwave Extraction and Hydro-Distillation
Authors: Erkan Naciye , Tao Zhou , Rupasinghe H. P. Vasantha , Uysal Burcu , Oksal Birsen S.
Published: March 2019

Solvent-free microwave extraction (SFME) for the isolation of essential oil from leaves of Murraya koenigii L. (Rutaceae) has been compared with the conventional hydro-distilled oil (HD) in terms of yield, composition, antioxidant activity, and antibacterial activity against Listeria innocua. The yield of essential oil obtained from 30 min of SFME was similar to that of HD for 180 min. By GC-MS analysis, the major compounds of the essential oil extracted by SFME, which were obtained in somewhat lower amounts than in the essential oil obtained by HD, were α-copaene (44.3%), β-gurjunene (25.5%), isocaryophyllene (12.1%), β-caryophyllene (8.7%) and germacrene D (2.9%). The content of oxygenated terpenes, slightly higher for the SFME-essential oil (2.3%) than the HD-essential oil (1.4%), were much lower than that of nonoxygenated terpenes in both oils. DPPH radical scavenging activities of both essential oils were relatively low (10%-24%). Complete inhibition of growth of L. innocua was observed with both SFME and HD essential oils, at 400 and 600 μg/mL (minimum inhibitory concentration), respectively. The SFME-essential oil at 300 μg/mL provided 92% inhibition, indicating its potential as a natural antimicrobial agent.
Antihepatitis B Virus Constituents of Solanum Erianthum
Authors: Chou Shen-Chieh , Huang Tsurng-Juhn , Lin En-Hung , Huang Chun-Huei , Chou Chang-Hung
Published: March 2019

Eleven compounds were isolated from the methanol extract of the leaves of Solanum erianthum D. Don, including five α-linolenic acid analogs, α-linolenic acid (1), 13 S-hydroxy-9( Z),11( E)-octadecadienoic acid (2), 9S-hydroxy-10( E),12( Z), 15( Z)-octadectrienoic acid (3), 9( Z),11( E)-octadecadienoic acid (4), and octadecanoic acid (5); two benzofuran-type lactones, loliolide (6) and dihydroactinidiolide (7); two steroidal alkaloids, solasonine (8) and solamargine (9); a flavonol glycoside, camelliaside C (10); and a flavone, 5-methoxy-(3″,4″-dihydro-3″,4″-diacetoxy)-2″,2″-dimethylpyrano-(7,8:5″,6″)-flavone (11). Among these isolated compounds, 9 showed the most potent activity against HBsAg, with an IC50 of 1.57 μM, followed by 8(IC50 is 5.89 μM). In the testing against HBeAg, 11 was the only active compound with an IC50 of 36.11 μM. Compound 9 also revealed strong inhibition of DNA replication towards HBV and its IC50 was 2.17 μM. However, α-linolenic acid (1) showed a prominent selected index (SI), both in anti-HBsAg and inhibition of DNA replication with SI values of 7.75 and 7.18, respectively. This is the first report that unsaturated fatty acid 1, steroidal alkaloid glycoside 9 and flavone 11, all showed excellent activity against HBV. These results provide lead candidates in the development of anti-HBV drugs from natural sources.
Chemical and Bioactivity Evaluation of the Bark of Neonauclea purpurea
Authors: Karaket Netiya , Supaibulwatana Kanyaratt , Ounsuk Supatsara , Bultel-Poncé Valérie , Pham Van Cuong , Bodo Bernard
Published: March 2019

Bioassay-guided fractionation of the MeOH extract from the stem bark of Neonauclea purpurea used in traditional medicine, resulted in the isolation of 2 indole alkaloids, cadambine (1) and α-dihydrocadambine (2), as well as a quinolic compound, 2,6-dimethoxy-1,4-benzoquinone (3). Antimalarial activity evaluation showed that compounds 2 and 3 exhibited mild in vitro antimalarial activity against Plasmodium falciparum, the chloroquine-resistant strain K1 with IC50 values of 6.6 and 11.3 μM, respectively. Compounds 1 and 2 showed no cytotoxicity to monkey (Vero) cells, but compound 3 showed weak cytotoxicity with an IC50 value of 1.19 μM.
Phenolic Constituents from the Heartwood of Artocapus Altilis and their Tyrosinase Inhibitory Activity
Authors: Nguyen Mai Ha Khoa , Nguyen Hai Xuan , Nguyen Mai Thanh Thi , Nguyen Nhan Trung
Published: March 2019

From the MeOH extract of the heartwood of Artocapus altilis, thirteen phenolic compounds have been isolated, namely curcumin (1), desmethoxycurcumin (2), retrodihydrochalcone (3), apigenin (4), tangeretin (5), nobiletin (6), O-methyldehydrodieugenol (7), dehydrodieugenol (8), β-hydroxypropiovanillone (9), p-coumaric acid (10), p-hydroxybenzaldehyde (11), vanillin (12), and vanillic acid (13). This is the first report on the presence of these compounds in the heartwood of A. altilis. Compounds 1, 2, and 10 showed more potent tyrosinase inhibitory activities, with IC50 values ranging from 2.3 to 42.0 μM, than the positive control kojic acid (IC50, 44.6 μM). The most active compound, p-coumaric acid (10) (IC50, 2.3 μM), was 22 times more active in tyrosinase inhibitory activity than kojic acid.
Total Phenolic Content and Antioxidant Activity of Salvia spp. Exudates
Authors: Giamperi Laura , Bucchini Anahi , Bisio Angela , Giacomelli Emanuela , Romussi Giovanni , Ricci Donata
Published: March 2019

The total phenolic content and antioxidant activity of 6 Salvia spp. exudates were measured to find new potential sources of natural antioxidants. Total phenolic content was assessed by a modified Prussian blue method, and the antioxidant activity by two methods: 1,1- diphenyl-2-picryl- hydrazyl (DPPH) radical scavenging capacity assay and lipoxygenase inhibitory assay. The total phenolic content ranged between 1.3 μg/mg DW ( S. fallax) and 74.0 μg/mg DW ( S. cacaliaefolia). In the DPPH test, S. cacaliaefolia was more effective than BHT, while in the inhibition of lipid peroxidation all the extracts presented good antioxidant capacity.
Hypoglycemic Constituents of Gynura divaricata Subsp. Formosana
Authors: Chou Shen-Chieh , Chuang Lee-Ming , Lee Shoei-Sheng
Published: March 2019

Gynura divaricata Kitam. subsp. formosana is a folk medicine used as a hypoglycemic agent for diabetes patients in Taiwan. Guided by the hexose transport assay, the hypoglycemic constituents of the aerial part of this plant were disclosed through chromatographic methods. They are fructooligosaccharides, including β-D-fructofuranose, sucrose, 1-kestose, nystose, and 1F-β-fructofuranosylnystose. The hexose transport assay indicated that nystose was the most potent among these compounds, showing a 46.7% difference from pinitol in the stimulation index at a concentration of 0.5 mg/mL.
The Chemical Composition of the Essential Oils of Cirsium palustre and C. rivulare and their Antiproliferative Effect
Authors: Nazaruk Jolanta , Karna Ewa , Kalemba Danuta
Published: March 2019

The composition of the essential oils of Cirsium palustre and C. rivulare and their antiproliferative activity against breast adenocarcinoma cells (MCF-7 and MDA-MBA-231) were investigated. The essential oils obtained by hydro-distillation from the roots (yield 0.2 and 0.1% v/w, respectively), leaves and inflorescences (yield below 0.01%), were analyzed by gas chromatography coupled with mass spectrometry (GC-MS). The composition of the essential oils in the respective organs of each plant differed considerably. On the other hand, similarities were observed in the composition of root and leaf oils. In C. palustre and C. rivulare root oil, 50 and 39 constituents were identified, accounting for 95.3% and 92.4% of the total content. The main components were aplotaxene and its derivatives, representing 78.6% and 46.6% of the total content. In leaf oils of both species, 59 and 49 compounds, respectively, were identified, representing 67.4% and 78.3% of the total content. The major constituents were β-damascenone (4.1% and 13.4%, respectively) and β-ionone (6.7% and 5.3%, respectively). Short-chain saturated and unsaturated aliphatic alcohols and aldehydes constituted another important group of compounds (17.7% and 9.0%, respectively). The essential oils of the roots have moderate anti-proliferative activity, with IC50 values ranging from 110 to 140 μg/mL. These concentrations were below the level able to inhibit the proliferation of healthy cells.
Monitoring Stepwise Proteolytic Degradation of Peptides by Supramolecular Domino Tandem Assays and Mass Spectrometry for Trypsin and Leucine Aminopeptidase
Authors: Ghale Garima , Kuhnert Nikolai , Nau Werner M.
Published: March 2019

A label-free optical detection method has been designed that allows direct monitoring of enzymatic peptide digestion in vitro. The method is based on the addition of a reporter pair, composed of the macrocyclic host cucurbit[7]uril (CB7) and the fluorescent dye acridine orange (AO), to detect the proteolytic degradation of peptides. The enzymatic activity of trypsin and leucine aminopeptidase (LAP) was investigated using H-LSRFSWGA-OH as a substrate. The substrate as well as the intermediary and final products (i.e., H-FSWGA-OH and phenylalanine) formed during its enzymatic hydrolysis differ in their binding affinity to the receptor CB7, which results in varying degrees of dye displacement and, therefore, different fluorescence intensities. CB7 showed a relatively weak binding constant of K ≈ 104 M–1 with the substrate, a relatively strong binding constant of K ≥ 106 M–1 with H-FSWGA-OH (which is a final product formed by trypsin digestion and the intermediary product formed during the enzymatic activity of LAP), and a moderate binding constant of K ≤ 105 M–1 with phenylalanine. Owing to this differential binding affinity of CB7 with the substrate and the corresponding products, the digestion of a peptide by trypsin was followed as a decrease in fluorescence signal, while the complete degradation of the peptide by LAP was monitored as a decrease and a subsequent increase in fluorescence signal. The kcat/ KM value for trypsin (2.0 × 107 min–1M–1) was derived from the change in fluorescence signal with time. Additionally, the complete degradation of the peptide by LAP was also followed by mass spectrometry. The use of a supramolecular sensing ensemble (macrocyclic host and dye) as a fluorescent reporter pair gives this method the flexibility to adapt for monitoring the stepwise degradation of different biologically relevant peptides by other proteases.
Proanthocyanidins: Oligomeric Structures with Unique Biochemical Properties and Great Therapeutic Promise
Authors: Xu Zhanjie , Du Peng , Meiser Peter , Jacob Claus
Published: March 2019

Proanthocyanidins represent a unique class of oligomeric and polymeric secondary metabolites found ubiquitously and in considerable amounts in plants and some algae. These substances exhibit a range of rather surprising physical and chemical properties which, once applied to living organisms, are translated into a multitude of biological activities. The latter include antioxidant properties, cancer chemoprevention, anti-inflammatory and anti-diabetic effects as well as some exceptional, yet highly interesting activities, such as anti-nutritional and antimicrobial activity. Despite the wide range of activities and possible medical/agricultural applications of proanthocyanidins, many questions still remain, including issues related to bioavailability, metabolism and the precise biochemical, extra- and intracellular targets and mode(s) of action of these highly potent materials. Among the various physical and chemical interactions of such substances, strong binding to proteins appears to form the basis of many of their biological activities. Once easy-to-use synthetic methods to produce appropriate quantities of pure proanthocyanidins are available, it will be possible to identify the prime biological targets of these oligomers, study oligomer-protein interactions in more detail and develop possible practical applications in medicine and agriculture.
Transannular Cyclization of (4S,5S)-Germacrone-4,5-epoxide into Guaiane and Secoguaiane-type Sesquiterpenes
Authors: Kuroyanagi Masanori , Shirota Osamu , Sekita Setsuko , Nakane Takahisa
Published: March 2019

Germacrone (1) and ( 4S,5S)-germacrone-4,5-epoxide (2) were isolated, along with guaiane and secoguaiane-type sesquiterpenes, from Curcuma aromatica plants. Compound 2 was derived from 1 and cyclized through transannular (T-A) reactions into various guaiane and secoguaiane-type sesquiterpenes in C. aromatica. The cyclization reaction of 2 was initiated by protonation at an epoxide oxygen atom, followed by cleavage of the epoxide ring and the formation of a C-C bond between C-1 and C-5 to give guaiane-type derivatives. Acidic and thermal treatments of 2 produced twelve sesquiterpenes having guaiane and secoguaiane skeletons. The structures of these products were elucidated by spectral methods, including 2D-NMR spectroscopy. Most were identified as sesquiterpenes isolated from C. aromatica as natural products. The T-A cyclization of 2 occurred via two transition states, a cross conformation and a parallel conformation. The mechanism of the T-A cyclization reaction of 2 is discussed.
Glucosylated Sesquiterpene Alcohols from Fraxinus griffithii
Authors: Macahig Rene Angelo , Harinantenaina Liva , Sugimoto Sachiko , Matsunami Katsuyoshi , Otsuka Hideaki , Takeda Yoshio , Shinzato Takakazu
Published: March 2019

Phytochemical investigation of the leaves of Fraxinus griffithii has led to the isolation of two new glucosylated acyclic sesquiterpene alcohols, griffithosides D (1) and E (2), along with iridoid and secoiridoid glycosides. The molecular structures of these compounds were elucidated using NMR, MS and other spectroscopic techniques, as well as comparison with literature data. The isolated compounds were tested for radical-scavenging activity and cytotoxicity against A549 human lung adenocarcinoma cells and Leishmania major parasites.
A New Unusual Δ11(12)-Oleane Triterpene and Anti-Complementary Triterpenes from Prunella Vulgaris Spikes
Authors: Du Dongsheng , Cheng Zhihong , Chen Daofeng
Published: March 2019

Anti-complementary activity-guided fractionation of the ethanolic extract of Prunella vulgaris spikes led to the isolation of a new, unusual Δ11(12) triterpene, 3β,13β-dihydroxyolic-11-ene-28-oic acid (1), along with thirteen known triterpenes (2-14). The structure of the new compound was established by 1D and 2D NMR spectroscopic analysis. All the isolates were evaluated for their anti-complementary activity against the classical pathway (CP) and alternative pathway (AP). Eight triterpenes (1-8) showed anti-complementary activity against CP and AP, with CH50 and AP50 values of 0.15-0.37 mg/mL, and 0.29-0.53 mg/mL, respectively. Mechanism study using complement-depleted sera showed that oleanolic acid (2) acted selectively on C1q, C5, and C9 components, while 2α-hydroxy oleanolic acid (3) interacted with C1q, C3, C5 and C9, and 2α,3α-dihydroxyolic-12-ene-28-oic acid (4) blocked C1q, C2, C3, C5 and C9.
Anilides and Toluidides of 3β-Acetyloleanolic Acid
Authors: Bednarczyk –Cwynar Barbara
Published: March 2019

Amide formation is one of the reactions that can be undertaken within the carboxyl group of oleanolic acid. A simple method for oleanolic acid anilide and toluidides synthesis is presented. The influence of the location of the methyl substituent on the reactivity of the amine group was tested and the “ ortho effect” of the methyl substituent within the molecule of o-toluidine on the time of reaction was observed. The structures of the newly obtained compounds were determined by spectroscopic methods.
Putralone, a Novel 10α-Hydroxy-25-nor D:A Friedo-Oleanane Triterpenoid from Putranjiva Roxburghii
Authors: Mukherjee Tulika , Sarkar Tapas , Paul Piyali , Chakraborty Ajit K. , Jaisankar Parasuraman , Mukhopadhyay Siba Brata
Published: March 2019

Chemical investigation of the leaves of Putranjiva roxburghii has resulted in the isolation of two new triterpenoids, putralone, a novel 10α-hydroxy-25-nor D:A friedo-olean-9(11)-en-3 one and 3β-acetoxy-cycloart-24-en-23-one, along with a rare hopanoid, adian-5-en-3β,29-diol. Other known triterpenoids isolated from this plant are 3β-acetoxy-adian-5-ene, putrol, putrone, putranjivadione, roxburghonic acid, friedelin, friedlan-3α-ol, oleanolic acid and erythrodiol. Interestingly, putralone is the first example of a naturally occurring nor friedo-oleanane triterpenoid having a hydroxyl functionality at the C-10 position.
Terpenoids and Related Compounds from Plants of the Family Compositae (Asteraceae)
Authors: Yaoita Yasunori , Kikuchi Masao , Machida Koichi
Published: March 2019

This review will summarize the authors’ studies on the structures of terpenoids and related compounds from plants of the family Compositae (Asteraceae). Eighty three new compounds have been obtained and characterized from seven species of the plants, namely, Erigeron annuus (L.) Pers., Erigeron philadelphicus L., Erigeron sumatrensis Retz., Ligularia dentata Hara, Ligularia stenocephala Matsum. et Koidz., Petasites japonicus Maxim. and Tussilago farfara L.
Steroidal Glycosides from Veronica chamaedrys L. Part I. The Structures of Chamaedrosides C, C1, C2, E, E1 and E2
Authors: Marchenko Alexandra , Kintya Pavel , Wyrzykiewicz Bozena , Gorincioi Elena
Published: March 2019

Two new spirostane glycosides, chamaedrosides C (1) and C1 (2), two new furostane glycosides, chamaedrosides E (4) and E1 (5), and two new furospirostane glycosides, chamaedrosides C2 (3) and E2 (6), have been isolated from Veronica chamaedrys L. plants. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR experiments, as well as MS analysis. The given compounds have been found for the first time.
Alkaloids from Some Amaryllidaceae Species and Their Cholinesterase Activity
Authors: Cahlíková Lucie , Benešová Nina , Macáková Kateřina , Kučerac Radim , Hrstka Václav , Klimeš Jiří , Jahodář Luděk , Opletal Lubomír
Published: March 2019

Alkaloid extracts of four Amaryllidaceae species were studied with respect to their acetylcholinesterase and butyrylcholinesterase inhibitory activity and alkaloid patterns. Twenty-one alkaloids were determined by GC/MS, and seventeen of them identified from their mass spectra and retention times. The GC/MS analysis of the alkaloid extract of Nerine filamentosa is the first phytochemical investigation of this species. Promising erythrocytic acetylcholinesterase inhibitory activity was demonstrated by the alkaloid extracts of Narcissus poeticus var recurvus, Nerine filifolia and N. filamentosa (IC50,HuAChE = 6.0 ± 0.1 μg/mL; IC50,HuAChE = 18.5 ± 0.8 μg/mL, IC50,HuAChE = 21.6 ± 1.1 μg/mL). The most potent inhibitory activity against serum butyrylcholinesterase was shown by extracts of Sternbergia lutea and Nerine filamentosa (IC50,HuBuChE = 3.7 ± 0.1 μg/mL; IC50,HuBuChE = 13.0 ± 0.7 μg/mL).
Three New Biflavonoids from Chinese Dragon's Blood, Dracaena cochinchinensis
Authors: Guan Jing , Guo Shun-Xing
Published: March 2019

Three new biflavonoids, named (2 Rγ S)-3′-methoxy-8-methylsocotrin-4′-ol (1), (2 Sγ R)-3′-methoxy-8-methylsocotrin-4′-ol (2), and (2 Rγ R)-8-methylsocotrin-4′-ol (3), were isolated from Chinese Dragon's blood [Dracaena cochinchinensis (Lour.) S. C. Chen], together with two known ones. The structures of these new biflavonoids were elucidated by a combination of HR-ESI-MS, 1H NMR, 13C NMR, HMQC, and HMBC spectra. The absolute configurations of compounds 1-4 were determined by quantum chemical calculation of the circular dichroism spectrum and comparison with the experimental CD spectrum.
Isolation of Antitrypanosomal Compounds from Vitis repens, a Medicinal Plant of Myanmar
Authors: Nyunt Khine Swe , Elkhateeb Ahmed , Tosa Yusuke , Nabata Kensuke , Katakura Ken , Matsuura Hideyuki
Published: March 2019

Bioactivity-guided fractionation of an ethanolic extract of Vitis repens led to the isolation of resveratrol (1), 11- O-acetyl bergenin (2), and stigmast-4-en-3-one (3). The compounds were examined for their in vitro antitrypanosomal activities against trypomastigotes of Trypanosoma evansi. Resveratrol showed antitrypanosomal activity with an IC50 value of 0.13 μM, whereas 11- O-acetyl bergenin and stigmast-4-en-3-one exhibited IC50 values of 0.17 and 0.15 μM, respectively.
Ajuganane: A New Phenolic Compound from Ajuga bracteosa
Authors: Hussain Javid , Begum Naeema , Hussain Hidayat , Khan Farman Ullah , Rehman Najeeb Ur , Al-Harrasi Ahmed , Ali Liaqat
Published: March 2019

Phytochemical investigation of Ajuga bracteosa Wall ex Benth. (Labiatae) resulted in the isolation of a new phenolic compound, ajuganane (1) and three known compounds, 3,4′-dihydroxy-3,6,7-trimethoxyflavone, 7-hydroxy-3,6,3′,4′-tetramethoxyflavone and ursolic acid. The structure of the new compound was elucidated by detailed spectroscopic (1H, 13 C NMR, COSY, HMQC, HMBC), and HR-EI-MS analysis.