Records of Natural Products

Articles In Press

Original Article

1) Cephalounei A, a New Cephalotaxus Alkaloid from the Powdered Stems of Cephalotaxus fortune Hook. f

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Kangkang Mei , Guokai Wang , Heping Cai and Zhihong Luo

A new Cephalotaxus alkaloid, namely Cephalounei A (1), was isolated from the stems of Cephalotaxus fortune Hook. f. Their structures were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR and HRESIMS. The relative and absolute stereochemistry of 1 was determined by a combination of NOESY correlations and electronic circular dichroism (ECD) spectra, respectively. The cytotoxicity of all compounds were evaluated against five cancer cell lines.

DOI
http://doi.org/10.25135/rnp.19.02.1197
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cephalotaxus alkaloid Cephalounei A ECD
Available online: May 23, 2019
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Original Article

2) Two New Cholestanol Glycosides from the Roots and Rhizomes of Smilacina henryi

Rec. Nat. Prod. (2019) in press ; 1 - 7
by Xin Zhang , Jing Sun , Shuo Zhang , Yafeng Yan , Rongxin Zhang , Xuanji Xue and Zengjun Guo

Abstract: Two new cholestanol glycosides (1 and 2) were obtained from the roots and rhizomes of Smilacina henryi. Their structures were determined as 5α-cholest-9(11)-ene-3β, 26-dihydroxy-16, 22-dione 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside (1), 5α-cholest-9(11)-ene-3β, 26-dihydroxy-16, 22-dione 3-O-β-D-glucopyranosyl-(1→2)- [β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside (2), by physicochemical properties and spectroscopic methods. In addition, the isolated glycosides were tested for their cytotoxic activity against human HepG2 tumor cells and compound 2 showed moderate activity with IC50 value of 59.32 μM.

DOI
http://doi.org/10.25135/rnp.19.03.1248
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Smilacina henryi cholestanol glycosides structure determination cytotoxicity
Available online: May 23, 2019
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Original Article

3) Cytotoxicity of Some Plants of the Asteraceae Family: Antiproliferative Activity of Psiadia punctulata Root Sesquiterpenes

Rec. Nat. Prod. (2019) in press ; 1 - 9
by Ammar Bader , Qasem Abdallah , Mohamed Abdelhady , Nunziatina De Tommasi , Nicola Malafronte , Usama Shaheen , Majdi Bkhaitan and Roberta Cotugno

According to the World Health Organization Cancer is the second leading cause of death globally. The methanol extracts of fourteen Middle-Eastern plants of the family Asteraceae were screened for antiproliferative activity on five cancer cell lines (A2780, MCF7, HeLa, RKO and Jurkat) by using MTT assay. Psiadia punctulata (DC.) Vatke was selected for isolation and elucidation of the bioactive constituents by 1D- and 2D-NMR, and MS analyses. Flow cytometry was used to evaluate cell cycle analysis, apoptotic hallmarks and reactive oxygen species. P. punctulata yielded a new sesquiterpene characterized as 7-hydroxy eudesman-3,5-dien-2-one (punctulin) (3) and three  known sesquiterpenes: 1, 2 and 4. The antiproliferative activity of all sesquiterpenes was evaluated in Jurkat (T-cell leukemia) and HeLa cancer cell lines. Compound 1 (1β-hydroxy-8-oxo-cyperone) has induced a significant growth inhibition in Jurkat and HeLa cells (IC50 =12 and 18µM respectively). Flow cytometry of compound 1 has elucidated the mechanism of action by showing its ability to induce cell cycle arrest in Jurkat cells mainly in G0/G1 and, less markedly, in G2/M. Compound 1 also expressed strong antioxidant activity by reducing the basal level of peroxides DHFDA-load in Jurkat cells. Compound 1 antioxidant activity may have contributed to the observed cell cycle arrest.

DOI
http://doi.org/10.25135/rnp.113.18.10.969
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cytotoxic Activity Asteraceae Leukemia Cell cycle Sesquiterpenes
Available online: May 21, 2019
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Original Article

4) New Oxoprotoberberine and Aporphine Alkaloids from the Roots of Amoora cucullata with Their Antiproliferative Activites

Rec. Nat. Prod. (2019) in press ; 1 - 8
by Parinuch Chumkaew , Passakorn Teerapongpisan , Jaraslak Pechwang and Theera Srisawat

Two new oxoprotoberberine alkaloids, amocurine A and B (1 and 2), a new aporphine alkaloid, amocurine C (3), along with three known compounds (4-6) were isolated from the roots of Amoora cucullata. Their structures were determined by analysis of spectroscopic data. The isolated compounds were evaluated for their antiproliferative activity against three human cancer cell lines (KB, oral cavity; MCF-7, breast cancer; and NCI-H187, small cell lung cancer). Compounds 3 showed the most potent activities against KB and MCF-7 cell lines with IC50 values 3.5 and 4.2 mM, respectively.

DOI
http://doi.org/10.25135/rnp.128.19.02.1181
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Oxoprotoberberine Aporphine Antiproliferative activity Amoora cucullata
Available online: May 05, 2019
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Original Article

5) A New Dimeric Sesquiterpenoid from Chloranthus japonicus

Rec. Nat. Prod. (2019) in press ; 1 - 8
by Qiyan Li , Yan Wang , Songsong Wen , Ying Wu , Lihua Xu and Zhenliang Sun

Phytochemical investigation into the whole plants of Chloranthus japonicus Sieb. led to isolation and identification of a new dimeric lindenane sesquiterpenoid, named chlojapolactone B (1), and two new phenolic derivatives (2 and 3). Their chemical structures were elucidated on the basis of HRESIMS and NMR spectroscopic data, and the absolute configuration of 1 was determined using the electronic circular dichroism (ECD) analysis.

DOI
http://doi.org/10.25135/rnp.127.19.02.1193
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Chloranthus japoni Dimeric sesquiterpenoid Phenolic derivative
Available online: May 05, 2019
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Original Article

6) Protein Tyrosine Phosphatase 1B Inhibitors from the Root Bark Pseudolarix amabilis (Nelson) Rehd. (Pinaceae)

Rec. Nat. Prod. (2019) in press ; 1 - 8
by Zhenggang Yue , Rui Zhou , Yihan He , Hongbo Xu , Yalei Pan , Liyan Lei , Pei Xie , Zhishu Tang and Jinao Duan

Pseudolarix amabilis (Nelson) Rehd, is a monotypic genus plant belonging to the family Pinaceae. The root bark , known as “Tu-Jin-Pi” has been used for the treatment of skin diseases. During our activity screening, the water-soluble part of the 70% EtOH extract of P. amabilis bark showed excellent inhibitory bioactivities on PTP1B enzyme, leading to the phytochemical isolation of the root bark of P. amabilis. Three oleanane-type compounds (1-3) and seven phenolic compounds (4-10) were isolated, in which oleanolic acid 3-O-β-D-glucuronyl-6′-ethyl ester (1) was identified as a new saponin. The chemical structures of these compounds were elucidated by 1D/2D nuclear magnetic resonance and high resolution mass spectra. In addition, their pharmacological inhibitory bioactivities on PTP1B enzyme were evaluated, and the three oleanane-type compounds 1-3 exhibited inhibitory bioactivities with IC50 values of 1.90 ± 0.37, 19.15 ± 0.10 and 10.44 ± 0.59 μM, respectively.

DOI
http://doi.org/10.25135/rnp.125.18.12.1132
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pseudolarix amabilis PTP1B inhibitors Isolation and identification Oleanane-type compounds Phenolic compounds Oleanolic acid 3-O-β-D-glucuronyl-6′-ethyl ester
Available online: April 30, 2019
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Original Article

7) Two New Lignans from Lycopodium japonicum Thunb.

Rec. Nat. Prod. (2019) in press ; 1 - 7
by Qin Ren , Zhenxing Zou , Yang Liu , Xi Chen , Kangping Xu and Guishan Tan

Two new lignans, named lycojaponicumoside A (1) and B (2), together with four known compounds (3˗6) were isolated from the n-BuOH extract of Lycopodium japonicum. Their structures were elucidated on the basis of extensive spectroscopic methods, especially various NMR techniques, HRESIMS and circular dichroism (CD). The absolute configuration of compound 1 was established by the calculation of electronic circular dichroism (ECD) curves. All of the compounds were evaluated for their cytotoxic activities against A549 and HepG2 human cancer cell lines, but those compounds did not exhibit cytotoxicity.

DOI
http://doi.org/10.25135/rnp.126.19.03.1205
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Lycopodium japonicum lignans ECD calculation
Available online: April 29, 2019
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Original Article

8) Chemical Compounds from the Twigs and Leaves of Caesalpinia cucullata Roxb

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Xuesong Liang , Dewen Bi , Fengqiu Li and Liqin Wang

Abstract: A new stilbene dimer, caesalstilbene A (1), along with twelve known compounds were isolated from the twigs and leaves of Caesalpinia cucullata Roxb by means of various chromatographic techniques. Their structures were identified on the basis of NMR spectral analysis and comparing their spectral data with those reported in the literatures. The absolute configuration of 1 was assigned by the comparison of the experimental and calculated electronic circular dichroism spectra. Compound 1 was evaluated for their cytotoxicity on HL-60, SMMC-7721, A-549, MCF-7 and SW-480 human cancer cell lines, but it was inactive. This is the first report of chemical investigation on Caesalpinia cucullata..

 

DOI
http://doi.org/10.25135/rnp.124.18.12.1088
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Caesalpinia cucullata Leguminaceae stilbene dimer caesalstilbene A
Available online: April 29, 2019
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Original Article

9) A New Heliquinomycin Analogue with Immunosuppressive Activity from Streptomyces sp. jys28

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Can Su , Chongxi Liu , Yongjiang Wang , Wen-sheng Xiang , Chenggang Zou and Sheng-Xiong Huang

Heliquinomycin (1) and a new analogue 9′-methoxy-heliquinomycin (2) were isolated from the culture broth of Streptomyces sp. jys28. The structure of new analogue was elucidated by comprehensive analyses of HR-ESI-MS and NMR spectroscopic data. Among them, Heliquinomycin (1) showed immunosuppressive and antibacterial activities.

DOI
http://doi.org/10.25135/rnp.123.18.12.1085
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Heliquinomycin Immunosuppressive activity Antibacterial activity
Available online: April 11, 2019
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Original Article

10) First Report on Volatile Composition of Tricholoma anatolicum in Comparison with Tricholoma caligatum

Rec. Nat. Prod. (2019) in press ; 1 - 10
by Hatıra Taşkın , Zeynep Dilan Çelik , Fuat Bozok , Turgut Cabaroğlu and Saadet Büyükalaca

Tricholoma anatolicum collected from Turkey is consumed by public and exported to Japan every year. It was previously identified as Tricholoma caligatum until it was recognized as a new species. In the existing literature, there is no information on the aromatic composition of T. anatolicum. Therefore, in this study it was aimed to identify the volatile composition of T. anatolicum together with T. caligatum. Species identification was confirmed using molecular analyses based on ITS rDNA sequencing. Volatile compounds of both mushroom species were extracted using liquid-liquid extraction method and determined by Gas Chromatography-Mass Spectrometry-Flame Ionization Detector (GC-MS-FID). In the two Tricholoma species, 31 volatiles were obtained and grouped in seven chemical classes. The amounts of alcohols, volatile acids and esters were found to be higher in T. anatolicum, whereas the amounts of terpenes were detected as higher in T. caligatum. 1-Octen-3-ol responsible for the mushroom-like odour was only found in T. anatolicum.

DOI
http://doi.org/10.25135/rnp.122.18.12.1095
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Tricholoma anatolicum Tricholoma caligatum Tricholomataceae volatile aroma composition Turkey
Available online: April 11, 2019
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Original Article

11) A New Aporphine Alkaloid from Illigera aromatic

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Kui-Wu Wang , Xiaoxin Wang , Haijiang Zhang and Yichao Ge

Chemical investigation of the aerial part of Illigera aromatic S.Z. Huang & S.L. Mo has resulted in the isolation and characterization of one new aporphine alkaloid, illigerine B (1), along with three known analogues laurodionine B (2), N-formyl-laurolitsine (3) and illigerine A (4). Their structures were established by spectrometric means and physico-chemical properties. The in vitro cytotoxic activities of compound 1 against Hela, SMMC7721, and Bcap37 cell lines were evaluated. Compound 1 exhibited moderate cytotoxic activity against the three tumor cell types, with IC50 values of 12.40 ± 0.78, 32.61 ± 2.05, and 28.69 ± 1.80 μg/mL. This work shown that aporphine alkaloids might be useful as characteristic markers in chemotaxonomic research of the genus Illigera.

DOI
http://doi.org/10.25135/rnp.121.18.11.1033
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Hernandiaceae Illigera aromatic Aporphine alkaloid lligerine B Cytotoxicity
Available online: April 02, 2019
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Original Article

12) A New Isoflavonolignan Glycoside from Abrus cantoniensis

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Fuxuan Wu , Miaomiao Yu , Wanling Chen , Lu Zhou , Dan Zhang , Yujie Peng , Xifeng Sheng , Hui Zou and Junjiang Fu

A new isoflavonolignan glycoside, namely cantoniensin A (1), along with three known compounds were isolated from Abrus cantoniensis. The structure of the new compound was elucidated on the basis of spectroscopic analyses, including 1D-, 2D-NMR and HRESIMS. Compound 1 is the second example of isoflavonolignan glycoside from nature and is also the first isoflavonolignan isolated from the genus of Abrus.

DOI
http://doi.org/10.25135/rnp.125.19.01.1165
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Leguminosae Abrus cantoniensis cantoniensin A isoflavonolignan isoflavonolignan glycoside
Available online: March 02, 2019
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Short Report

13) Thymol derivatives from Eupatorium fortunei

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Minh Giang Phan , Vu Minh Trang , Do Thi Viet Huong , Susumu Kawakami and Hideaki Otsuka

The presence of thymol derivatives in the leaves and twigs of E. fortunei collected in Northern Vietnam was investigated. Five thymol derivatives, including new 9-O-angeloxy-10-hydroxy-8-methoxythymol, 10-acetoxy-9-chloro-8,9-dehydrothymol, 9-acetoxy-8,10-epoxythymol-3-O-isobutyrate, 8,10-epoxy-9-hydroxy-thymol-3-O-tiglate, and 9-acetoxy-8,10-epoxythymol-3-O-angelate together with six other compounds, including taraxasteryl acetate, o-coumaric acid, trans-melilotoside, (–)-loliolide, coumarin, and b-sitosterol were isolated. The structures of the isolated compounds were determined on the basis of MS and NMR spectroscopic data.

DOI
http://doi.org/10.25135/rnp.122.18.11.1032
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Eupatorium fortunei Asteraceae thymol
Available online: February 24, 2019
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Original Article

14) Structural Elucidation of a Coumarin with New Skeleton from Artemisia ordosica

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Wugedunqiqige Bao , Qinghu Wang and Junsheng Hao

A new coumarin, named as arteordocoumarin A (1), together with three known compounds (2-9) were isolated from the CHCl3 extract of Artemisia ordosica (A. ordosica). The structures of 1 was elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.

DOI
http://doi.org/10.25135/rnp.120.18.10.1026
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Arteordocoumarin A Artemisia ordosica NMR
Available online: February 24, 2019
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Original Article

15) Volatile oil constituents of Crataegus azarolus L. and Crataegus pallasii Grisb.*

Rec. Nat. Prod. (2019) in press ; 1 - 7
by Najat Agiel , Duygu Yigit Hanoğlu , Azmi Hanoğlu , K.H. Can Baser and Filiz Mericli

In this study the volatile oils constituents of the inflorescence and unripe fruits of Crataegus azarolus L. and Crataegus pallasii  Grisb. were investigated. Fifty-four compounds were identified by GC and GC-MS analysis. The major outstanding constituents of the essential oil in all samples (dried and fresh C. azarolus and dried C. pallasii) were; tricosane (33.8%, 29.3%, 34.0 %), pentacosane (24.6%, 21.1%, 30.8%), heptacosane (12.5%, 10.2%, 11.7%), and tetracosane (6.0%, 5.6%, 5.7%), respectively. Besides these alkanes, ten compounds (nonanal, β-elemene, undecanal, β-caryophyllene, (E, E)-α-farnesene, eicosane, hexyl benzoate, (Z)-3-hexenyl benzoate, (E)-2-hexenyl benzoate, docasane) were determined in all samples. Carvacrol, carvacryl acetate, carvone, and thymol were determined for the first time from C. pallasii essential oil. (E)-β-damascenone was determined only in dried C. azarolus oil; sesquiterpene compounds valencene, α-selinene and β-selinene, d-cadinene, germacrene D, selina-3,7(11)-diene, spathulenol, and d-cadinol were determined only in fresh C. azarolus sample. On the other hand (2E,6E)-farnesol was determined in dried C. azarolus and C. pallasii samples.

 

DOI
http://doi.org/10.25135/rnp.123.18.11.1060
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Crataegus azarolus Crataegus pallasii volatile constituents GC-MS analysis
Available online: February 23, 2019
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Original Article

16) Polyacetylenes from the roots of Aralia dumetorum

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Meng-Yuan Jiang , Chun-Tao Yang , Xiao-Yun Pu , Guangmiao Fu , Wei Wang , Yu-Xiao Li , Lei Feng , Zhi-Rui Niu , Jian-Lin Tan and Xiang-Zhong Huang

A new polyacetylene, heptadeca-8,16-dien-4,6-diyn-3,l0-diol (1) along with four known polyacetylenes, 1,2-dihydrodendroarboreol B (2), heptadeca-1,8-dien-4,6-diyn-3,l0-diol (3), 3R, 8S-falcarindiol (4) and 3R,8R-dehydrofalcarindiol (5) were isolated from the ethanol extract of Aralia dumetorum. The structures of the isolates were elucidated on the basis of 1D and 2D NMR spectrums and by comparison of the spectroscopic data with those reported for structurally related compounds. The α-glucosidase inhibitory activity of compounds 1-5 was evaluated using α-glucosidase inhibitory assay, in which all compounds displayed good inhibitory activity with IC50 values ranging from 4.2 ~ 36.2 μM..

DOI
http://doi.org/10.25135/rnp.119.18.09.940
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Araliaceae Aralia dumetorum polyacetylenic compound α-glucosidase inhibitor
Available online: February 11, 2019
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Original Article

17) NF-κB Inhibition Activity of Curcumin-Loaded Sterically Stabilized Micelles and Its Up-Regulator Effect on Enhancement of Cytotoxicity of a New Nano-Pirarubicin Formulation in the Treatment of Breast Cancer

Rec. Nat. Prod. (2019) in press ; 1 - 15
by Zahra Eskandari , Fatemeh Bahadori , Melda Altikatoglu , Vildan Betul Yenigun , Abdurrahim Kocyigit and Hayat Onyuksel

This study aims to investigate the effects of co-administration of nano-Curcumin on anticancer effect of nano-Pirarubicin considering the fact that the clinical use of Pirarubicin and other anthracyclines has been limited by development of multidrug resistance (MDR) and based on previous data which have shown that Curcumin can down-regulate MDR proteins and suppress the activity of Nuclear factor-kappa B (NF-κB) a protein involved in chemoresistance. Nano micellar formulations of both Curcumin and Pirarubicin were separately synthesized using 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine-N-methoxy-[poly(ethylene glycol); PEG MW 2,000] (DSPE-PEG2000). The produced sterically stabilized micelles (SSM) are very well known drug delivery systems in terms of their enhanced efficacy and good toxicity profile. We measured the differences of NF-κB levels in two different situations: when Pirarubicin is used alone and when it is co-administered with Curcumin. This study showed that co-administration of SSM-Curcumin (CSSM) and SSM-Pirarubicin (PSSM) with size of 12.81 nm enhances the efficacy of Pirarubicin by suppressing P65, an NF-κB subunit. Furthermore, we showed that SSM is able to successfully enhance water solubility and therapeutic stability of curcumin for using as a complementary agent.

DOI
http://doi.org/10.25135/rnp.108.18.10.984
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Curcumin pirarubicin nanoparticles NF-κB breast cancer
Available online: January 19, 2019
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Short Report

18) A New Ursane-Type Triterpene from the Roots of Salvia miltiorrhiza Bunge

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Le Quoc Hung, Phuong Thien Thuong and Nguyen Huu Tung

Danshen (Salvia miltiorrhiza) is a one of the most well-known medicinal herbs in the Oriental medicine for treatment of certain cardiovascular disoders. Our current research on triterpenoid component in danshen roots led to the isolation of a new highly hydroxylated ursane-type triterpene, urs-12,20(30)-dien-3β,7β,24-triol-28-oic acid (2) and one known triterpene, epiasiatic acid (1). Their structures were elucidated on the basis of extensive spectroscopic analyses including NMR and MS spectra and comparison with literature data. The new compound 2 showed medium activity against HL-60 cells with the IC50 value of 16.3 μM. The obtained results of unique bioactive triterpenes from danshen contributed not only to its phytochemical profile associated with chemotaxanomy but also to biological evidence of the title plant.

DOI
http://doi.org/10.25135/rnp.97.18.07.330
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Danshen Salvia miltiorrhiza Lamiaceae triterpene
Available online: January 19, 2019
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Review Article

19) Biodiversity and Secondary Metabolites of Marine Sponges from Turkey

Rec. Nat. Prod. (2019) in press ; 1 - 12
by Hajar Heydari , Bulent Gozcelioglu and Belma Konulugil

Turkey is surrounded by the Black Sea, the Aegean Sea and the Mediterranean sea, comprising a rich source of marine biodiversity. Among all marine species, sponges with a wide range of secondary metabolites are an important potential for drug discovery. There are many studies on sponges and their secondary metabolites, but not enough study about Turkish sponges. The present review gives an overview of the current research trends on secondary metabolites from Turkish marine sponges and some of their biological activities. Until today alkaloids, steroids and phenolic compounds have been isolated and determined from Turkish sponges. To our knowledge, this is the first review about Turkish sponges.  Furthermore, we have tried to introduce our Marine Herbarium of Ankara University Pharmacy Faculty (MAP).

DOI
http://doi.org/10.25135/rnp.118.18.07.340
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Bioactivity biodiversity secondary metabolite sponge
Available online: January 14, 2019
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Original Article

20) New Xanthone from Millettia pachyloba Drake

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Zhi Na , Qishi Song and Qingfei Fan

A new xanthone, 1,7-dihydroxy-2,3,5,6-tetramethoxyxanthone (1), together with eight known compounds including one xanthone (2) and seven isoflavones (3-9) has been isolated from the leaves of Millettia pachyloba. This is the first report on the isolation of xanthone from the genus Millettia. The structure of the compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS. Compound 1 exhibited weak cytotoxicity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7 and SW480.

DOI
http://doi.org/10.25135/rnp.116.18.10.1020
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Millettia pachyloba Drake Leguminosae xanthone
Available online: January 10, 2019
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Original Article

21) Anti-inflammation C19-diterpenoid Alkaloids from Delphinium giraldii Diels

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Yan Liu , Zhiyang Liu , xinyi wang , Jing Zhang , Fangfang Liu and Yunlong Cong

Two new C19-diterpenoid alkaloids named Delphinium alkaloid A (1) and Delphinium alkaloid B (2) were isolated from the Delphinium (Ranunculaceae). Their structures were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR and HR-Q-TOF-MS. Compound 1 showed anti-inflammatory activity by regulating the inflammatory reaction induced by LPS in Caco2 cell.

DOI
http://doi.org/10.25135/rnp.117.18.09.954
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Delphinium giraldii Diels chemical constituents diterpenoid alkaloids anti-inflammatory
Available online: January 07, 2019
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Original Article

22) Phenolic Derivatives from Dioscorea bulbifera

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Guokai Wang , Juan Zheng , Jaising Yang , Yunpeng Sun , Nan Zhang , Huiwen Liu and Guo-Kai Wang

Two new phenolic derivatives, diosbulbiol A (1), diosbulbiol B (2), and  six known compounds were isolated from Dioscorea bulbifera. Their structures was determined by MS, IR, UV, 1D- and 2D-NMR. The cytotoxicity of new compounds were evaluated against four cancer cell lines.

DOI
http://doi.org/10.25135/rnp.114.18.10.1003
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Dioscorea bulbifera dioscorea cytotoxicity phenolic derivatives diosbulbiol A diosbulbiol B
Available online: December 25, 2018
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Original Article

23) A new pericarbonyl lignan from Amauroderma rude

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Miao Dong , Zuhong Ma , Qiaofen Yang , Qiuyue Hu , Yanqing Ye and Min Zhou

A new pericarbonyl lignan (1), named amaurolignan A was isolated from an ethanol extract of the fruiting bodies in Amauroderma rude of family Ganodermataceae, together with two known lignans, 4-methoxymatairesinol 4′-β-D-glucoside (2) and lappaol F (3). The structures of compounds (1-3) were elucidated using NMR and MS spectroscopic methods.

DOI
http://doi.org/10.25135/rnp.115.18.10.1007
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
lignans Amauroderma rude
Available online: December 25, 2018
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Original Article

24) Chemical Composition, Enantiomeric Distribution and AChE-BChE Activities of the Essential Oil of Myrteola phylicoides (Benth) Landrum, from Ecuador

Rec. Nat. Prod. (2018) in press ; 1 - 8
by James Calva , Jessica M Castillo , Nicole Bec , Jorge Ramirez , José Miguel Andrade , Christian Larroque and Chabaco Armijos

The volatile constituents of the essential oil (EO) of Myrteola phylicoides (Benth) Landrum, from Ecuador, extracted by steam distillation have been analyzed. A total of 37 compounds, representing 90.30% the total essential oil sample were identified. Monoterpenes hydrocarbons (53.06%) and sesquiterpene hydrocarbons (35.24%) were the principal groups of compounds. The major components were identified as α-pinene (30.94%), (E)-caryophyllene (21.93%), β-pinene (14.45%) and α-humulene (9.56%). The essential oil of M. phylicoides showed weak in vitro activity against AChE inhibition with IC50 value 60.8 μg/mL and a low BChE activity with IC50 value >250 μg/mL. This is the first report on the chemical composition of the essential oil of this species.

DOI
http://doi.org/10.25135/rnp.112.18.09.893
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Myrteola phylicoides essential oil AChE BChE
Available online: December 17, 2018
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Original Article

25) Chemical Composition and Biological Activities of the Essential Oil from Aristolochia fordiana Hemsl

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Pengxiang Lai , Xiao-Dan Su , Yang Gao , Yingxin Xiang , Pengxiang Lai and Xiang Xing

Abstract:  The present study investigated the chemical composition of the essential oil obtained from the aerial parts of Aristolochia fordiana Hemsl (AF-EO) using GC-FID and GC-MS, and evaluated the in vitro biological activities of the essential oil. Forty-nine compounds representing 99.6% of the total oil were characterized. The main constituents were identified as β-chamigrene (17.0%), β-caryophyllene (11.1%), α-bulnesene (11.0%) and β-pinene (10.2%). Furthermore, the antibacterial activity of the essential oil of A. fordiana was studied using disc diffusion and micro-broth dilution assays. AF-EO exhibited a significant antibacterial activity against Staphylococcus aureus and Bacillus subtilis with MIC values below 100 μg/mL. Besides, the results of MTT assays indicated that the essential oil exhibited a moderate cytotoxic activity on HepG2 (liver hepatocellular cells) and MCF-7 (human breast adenocarcinoma cells) cell lines. However, the AF-EO showed a weak antioxidant activity in DPPH•, ABTS•+ and FRAP assays.

DOI
http://doi.org/10.25135/rnp.111.18.09.897
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Aristolochia fordiana Hemsl essential oil antibacterial activity cytotoxic activity antioxidant activity
Available online: November 28, 2018
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Original Article

26) Assessment of Endemic Cota fulvida (Asteraceae) for Phytochemical Composition and Inhibitory Activities against Oxidation, -Amylase, Lipoxygenase, Xanthine Oxidase and Tyrosinase Enzymes

Rec. Nat. Prod. (2018) in press ; 1 - 13
by Gulmira Özek , M. Ufuk Özbek , Süleyman Yur , Fatih Göger , Munevver Arslan and Temel Özek

In the present work, chemical compositions of essential oil and methanol extract of endemic Cota fulvida (Grierson) Holub were investigated as well as their antioxidant, antidiabetic, antiinflammatory and antimelanogenesis potent. The phytochemical analyses have been performed with GC-MS/FID and LC-MS/MS techniques. The essential oil was characterized with hexadecanoic acid (25.6 %), camphor (6.1 %), caryophyllene oxide (5.3 %), 1,8-cineole (4.9 %) and humulene epoxide (3.9 %). In the extract, phenolic acids, phenylpropanoid dimer and flavonoids were detected. The major constituents of the extracts were found to be 5-feruloylquinic acid, caftaric acid, 3,5-O-dicafeoylquinic acid and quercetin rutinoside. The antioxidant activities of the oil and extract were evaluated through scavenging of free radicals, inhibition of linoleic acid peroxidation and superoxide anion radical (O2-) generated by xanthine - xanthine oxidase (XO) system. The extract showed free radical scavenging activity (IC50 0.131 mg/mL), Trolox equivalent antioxidant capacity (1.33 mM) and inhibited (Inh. 36.3 %) peroxidation of lipids. The oil and extract demonstrated significant hypoglycemic activity via inhibition of porcine pancreatic a-amylase. The antiinflammatory effects of the oil and extract via inhibition of 5-LOX enzyme were found as 53.7 % and 23.9 %, respectively. The extract demonstrated moderate inhibitory effect (23.3 %) on oxidation of L-DOPA via inhibition of tyrosinase enzyme.

DOI
http://doi.org/10.25135/rnp.109.18.09.875
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cota fulvida Essential Oil Extract GC-MS/FID LC-MS/MS Antioxidant
Available online: November 15, 2018
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Original Article

27) The Chemical Composition of Volatile Oil and Biological Activity of Rhododendron caucasicum

Rec. Nat. Prod. (2018) in press ; 1 - 8
by Seda Fandaklı , Nurettin Yaylı , Nuran Kahriman , Emel Uzunalioğlu , Nevin Ulaş Çolak , Sercan Yıldırım and Ahmet Yasar

The aim of this research was to investigate the effect of different extraction methods and chemical composition of the essential oil and solid-phase microextraction (SPME) from Rhododendrum caucasium Pall. The volatiles of R. caucasicum have been isolated by hydro distillation (HD) and SPME. The compositions of the volatiles were characterized by GC-FID/MS. A total of twenty-five and thirty-one compounds were identified constituting over 89.25%, and 90.33% of volatiles obtained with HD and SPME, respectively. The main volatile constituents of R. caucasicum were found to be calarene (46.13% (HD) and 54.91% (SPME)) and sandaracopimaradiene (25.93% (HD) and 8.16% (SPME)). Furthermore, the obtained essential oil (EO) and solvent extracts (n-hexane and methanol) of R. caucasicum were tested against the following nine bacteria: Escherichia coli, Yersinia pseudotuberculosis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Mycobacterium smegmatis, Candida albicans, and Saccharomyces cerevisiae. The EO showed moderate antimicrobial activities with the inhibition zone from 6 to18 mm against E. faecalis, S. aureus, B. cereus and M. smegmatis, respectively. Methanol extract gave better antimicrobial activity against the P. aeruginosa, E. faecalis, S. aureus, and B. cereus with the almost 15 mm inhibition zones.

DOI
http://doi.org/10.25135/rnp.107.18.09.952
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Rhododendron caucasicum; hydrodistillation; SPME; essential oil; antimicrobial activity; GC-FID/MS.
Available online: November 15, 2018
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Short Report

28) Glutinosine A: A New Morphinandienone Alkaloid from Litsea glutinosa

Rec. Nat. Prod. (2018) in press ; 1 - 4
by Yubin Ji, Chenxu Wang, Yuchen Zhang, Caiyun Zhang, Di Cui and Xiaopo Zhang

A new morphinandienone alkaloid, named glutinosine A was isolated from the root barks of Litsea glutinosa. The new structure was determined by various spectroscopic techniques including 1D (1H-, 13C-NMR), 2D-NMR (HMBC, HSQC, COSY and ROESY) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). The effects of the new compound on glucose consumption in HepG2 cells were evaluated. Whereas, the result showed that this compound displayed no activity in stimulating glucose consumption.

DOI
http://doi.org/10.25135/rnp.92.18.06.306
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Litsea glutinosa Glutinosine A morphinandienone glucose consumption activities
Available online: November 12, 2018
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Original Article

29) Chemical Compositions of Essential Oil of Piper Species from Atlantic Forest of Amazonia, Brazil

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Claudio Augusto Gomes da Camara , Carolina Alves de Araujo , Marcilio Martins de Moraes , Geraldo José Nascimento de Vasconcelos , Charles Eugene Zartman and Marta Regina Silva Pereira

Essential oils from the leaves of Piper japurense, P. coariense, P. auriculifolium, P. curtistilum, P. alatipetiolatum and P. brevesanum from the Amazon Forest (Brazil) were obtained through hydrodistillation. The chemical composition of the oils was determined using gas chromatography and mass spectrometry, which revealed the presence of 108 compounds representing 95.14 ± 0.35%, 95.64 ± 0.59%, 95.57 ± 0.48%, 92.05 ± 0.27%, 96.24 ± 1.04% and 91.31 ± 0.76% of the oils, respectively. The major components were α-eudesmol in the P. japurense (22.05 ± 0.15%) and P. coariense (27.33 ± 0.33%) oils, premnaspirodiene (32.26 ± 0.03%) in the P. auriculifolium oil, caryophyllene oxide (28.69 ± 0.17%) in the P. curtistilum oil, linalool (43.88 ± 0.50%) in the P. alatipetiolatum oil and β-elemene (12.75 ± 0.06%) in the P. brevesanum oil.

DOI
http://doi.org/10.25135/rnp.110.18.09.904
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Piper ssp Amazonia biome Essential oil Premnaspirodiene
Available online: November 12, 2018
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Original Article

30) A New Diterpene: Abietane Glycoside from the Roots of Isodon rugosus Wall Ex Benth.

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Arif Ullah, Ghias Uddin, Mamoon Ur Rashid, Ismail Ismail, Nasruddin, Bina Shaheen Siddiqui, Zahoor Ullah, Muhammad Alamzeb

The methanolic extract of the roots of Isodon rugosus were subjected to chromatographic separation, yielded two diterpenes: a new compound named rugosodon 1 and a known compound oridonin 2. The new compound 1 was elucidated as 1-O-α-D-glucopyranosyl-7α,13β-dihydroxyabieta-8(9)-en-11-one and the known compound 2 as 7α,20-epoxy-1α,6β,7,14-tetrahydroxy-kaur-16-en-15-one (oridonin), based on the chemical hydrolysis, physicochemical and spectroscopic data of IR, ESIMS, EIMS, 1D, and 2D NMR. The compounds 1-2 were subjected to bioassay studies of cytotoxicity and α-glucosidase inhibition potential. Rugosodon 1 showed significant potential of α-glucosidase inhibition with IC50 0.453 mg/mL, as compared to the standard acarbose (IC50 0.921 mg/mL). The compounds 1-2 failed to show any significant results for the cytotoxic screening against the three human cancer cell lines (NCI-H460, HeLa and MCF-7).

DOI
http://doi.org/10.25135/rnp.101.18.06.310
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Abietane diterpene glycoside Isodon rugosus rugosodon oridonin
Available online: November 11, 2018
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