Records of Natural Products

Articles In Press

Original Article

1) Inhibition of iNOS Induction and NF-κΒ Activation by Taste Compounds from the Edible Mushroom Tricholoma caligatum (Viv.) Ricken

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Ebru Erol , Zulfiqar Ali , Mehmet Ozturk , Shabana Khan and Ikhlas Khan

Abstract

Tricholoma caligatum (Viv.) Ricken is an edible mushroom that belongs to matsutake group. The first chemical investigation of the three different extracts of Tricholoma caligatum resulted in two new compounds, 8-demethoxylascivol (1) and 8-epi-lascivol (2) and six known compounds, lascivol (3), trametenolic acid (4), ergosterol (5), ergosterol peroxide (6), 5a, 6a-epoxyergosterol (7), and cerebroside B (8). Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR data. The biological activities of all the compounds were evaluated toward multiple targets related to inflammation and metabolic disorder such as NF-κΒ, iNOS and ROS. The findings of this study reveal that the edible mushroom Tricholoma caligatum could be a potential source for anti-inflammatory bioactive metabolites.

DOI
http://doi.org/10.25135/rnp.139.19.04.1263
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Tricholoma caligatum iNOS NF-κΒ anti-inflammatory lascivol
Available online: June 22, 2019
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Original Article

2) Comparative Effects of Flavonoids from Fructus Sophorae on Rat Osteoblasts in vitro

Rec. Nat. Prod. (2019) in press ; 1 - 12
by Yong Yang , Yaping Tian , Qinghe Zhang , Xiaoqing Li , Yun Fu , Haotian Pei and Dan Lu

Fructus Sophorae (FS), the dry mature fruit of Sophora japonica Leguminosae, is a valuable traditional Chinese medicine resource with flavonoids as the major active ingredients. To identify the plant-derived estrogen-like flavonoids serving as potential osteoporosis chemopreventive agents, we isolated and identified 27 flavonoids compounds, including 17 compounds obtained for the first time from FS. To screen out the flavonoids with estrogen-like biological behavior from the 11 high yield compounds, we set up an in vitro screening system in rat osteoblast MC3T3-E1 cells including MTT assay, alkaline phosphatase staining and Alizarin red S staining assay to examine the effects on cell proliferation, differentiation and mineralization of osteoblast cells respectively. Six flavonoids, including genistein, sophoricoside, sophorabioside, sophoraflavonoloside, nicotiflorin and rutin, significantly increased the cellular activity of MC3T3-E1 cells. Furthermore, blocking the estrogen receptor signaling by tamoxifen compromised the effects above significantly, suggesting the 6 compounds behave as estrogen-like reagents. Moreover, the interaction between the six flavonoids from FS and estrogen receptor was clarified by molecular docking method from Glide XP. Collectively, being used as food and medicine in China, FS is rich in flavonoids with estrogen-like effects, may be used as healthy supplementary in treating postmenopausal women osteoporosis.

DOI
http://doi.org/10.25135/rnp.138.19.04.1262
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Fructus Sophorae Flavonoid Phytoestrogens Estrogen Receptor Osteoporosis
Available online: June 22, 2019
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Original Article

3) Two Novel Sesquiterpenes and A New Pregnane Derivative from the South China Sea Gorgonian Subergorgia suberosa

Rec. Nat. Prod. (2019) in press ; 1 - 8
by Xian-Qiang Chen , Nannan Xing , Bin Yang , Xuefeng Zhou , Chenghai Gao and Yonghong Liu

Two novel sequiterpenes isosuberosenol A (1), suberosain A (2), and a new pregnane derivative 4-hydroxymethyl-5β-pregnan-3, 20-dione (3) have been isolated from the South China Sea gorgonian Subergorgia suberosa. Their structure and relative stereochemistry were established based on the detailed spectroscopic analysis, including HR-ESI-MS, 1D- and 2D NMR spectra. The skeleton of isosuberosenol A (1) have been previously undescribed. The discovery of isosuberosenol A (1) provides some strong support for the plausible biogenetic pathway of quadrone type sesquiterpenes.

DOI
http://doi.org/10.25135/rnp.137.19.04.1257
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
sesquiterpene pregnane derivative Subergorgia suberosa
Available online: June 22, 2019
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Original Article

4) Bioassay-guided Isolation and Identification of Anti-inflammatory Sesquiterpene Lactones from Chrysophthalmum montanum (DC.) Boiss.

Rec. Nat. Prod. (2019) in press ; 1 - 9
by Fatma Ayaz , Esra Küpeli Akkol , Nezhun Gören , İhsan Çalış , F. Tuğçe Gürağaç Dereli , Hayri Duman , Muhammad Iqbal Choudhary and Nurgün Küçükboyacı

The aerial parts of Chrysophthalmum montanum (DC.) Boiss. (Asteraceae) is traditionally used for wound healing, as well as for the treatment of common cold, sinusitis, and other inflammatory diseases. The objectives of this study were to identify potential anti-inflammatory effects of the methanol extract, and its different polarity subextracts (n-hexane, chloroform, n-butanol, and remaining aqueous), and guaianolide-type sesquiterpene lactones [6α-acetoxy-4α-hydroxy-1βH-guaia-9.11(13)-dien-12.8α-olide (1), 6α-acetoxy-4α-hydroxy-9β.10β-epoxy-1βH-guaia-11(13)-en-12.8α-olide (2), 4α,6α-dihydroxy-1β,5α,7αH-guaia-9(10),11(13)-dien-12,8α-olide (3), and (4α,5α,8β,10β)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide (4)] from the aerial parts of C. montanum. In order to evaluate the anti-inflammatory activity of C. montanum, carrageenan- and PGE2-induced hind paw edema, and acetic acid-induced increase in capillary permeability mice models were used. The methanol extract, the chloroform subextract, and compounds 3, and 4 were shown to possess anti-inflammatory activity in in vivo models at 100 mg/kg dose. The results provide a biological, and phytochemical basis for the traditional use of C. montanum aerial parts for inflammatory conditions in Turkish folk medicine.

DOI
http://doi.org/10.25135/rnp.135.18.11.1074
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Asteraceae Chrysophthalmum montanum sesquiterpene lactones anti-inflammatory carrageenan prostaglandins
Available online: June 16, 2019
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Original Article

5) Histone Deacetylase Inhibitor Induced Lipase Inhibitors from Endophytic Phomopsis sp. 0391

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Shan-ling Sheng , Yan-ping Li , Hai-ying Xiang , Yun Liu , Yu-dan Wang , Ling-peng Kong , Gang Du , Qiu-fen Hu , Yi-jian Chen and Wei-guang Wang

Abstract: Seven compounds including a new one named as 13-angeloyloxy-diplosporin (1) were isolated from the endophytic Phomopsis sp. 0391 cultivated in the presence of a histone deacetylase inhibitor. All of these isolates were evaluated for lipase suppressive activities and we firstly found that compounds cytosporone B (5) and dothiorelone A (6) displayed significant lipase inhibited activities compared to the positive control (Orlistat, IC50 = 43 μg/mL) with the IC50 values at 115 and 275 μg/mL, respectively.

DOI
http://doi.org/10.25135/rnp.134.19.01.1243
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Natural products Endophytic fungi Chemical epigenetics approach Lipase inhibitor
Available online: June 16, 2019
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Original Article

6) Chemical Constituents of Croton thurifer Kunth as α-Glucosidase Inhibitors

Rec. Nat. Prod. (2019) in press ; 1 - 11
by Vladimir Morocho , Danya Sarango , Claudia Cruz-Erazo , Nixon Cumbicus , Luis Cartuche and Alirica I. Suárez

Phytochemical investigation of Croton thurifer, collected in Loja-Ecuador, led to the isolation of seven known compounds identified as: (3R, 20S) -3-palmitate-20-hydroxydammar-24-ene (1); (3R, 20S)-3-acetoxy-20-hydroxydammar-24-ene (2); trans-phytol (3); vomifoliol (4); β-sitosterol (5); trans-tiliroside (6) and sparsifol (7). The structures of the isolated compounds were determined by NMR, MS, as well as by comparison with literature data. The hypoglycemic activity of the crude extracts and isolated compounds was assessed by their ability to inhibit α-glucosidase activity. The hexane and methanol extracts did not show any inhibitory activity on α-glucosidase, while the ethyl acetate extract (EtOAc) showed very low inhibitory activity with IC50= 1.77 mg/mL. Two of the seven isolated compounds exhibited good inhibitory activity with IC50 values much higher than acarbose (377 μg/mL). trans-tiliroside was the compound with the highest inhibitory activity (IC50 = 114.85 μg / mL), while (3R, 20S)-3-Acetoxy-20-hydroxydammar-24-ene had moderate inhibitory activity (IC50=292.87). Trans-tiliroside exherted a non-competitive inhibition with Km values between 368 and 358 μM and Vmax value from 695 and 325 nM/min for unhibited and inhibited reaction, respectively and a Ki of  163,6 μM.

DOI
http://doi.org/10.25135/rnp.136.18.11.1069
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Croton thurifer α-glucosidase trans-tiliroside (3R, 20S)-3-Acetoxy-20-hydroxydammar-24-ene
Available online: June 07, 2019
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Original Article

7) Roselle Seed Oil and its Nano-Formulation Alleviated Oxidative Stress, Activated Nrf2 and Downregulated m-RNA Expression Genes of Pro-inflammatory Cytokines in Paracetamol-intoxicated Rat Model

Rec. Nat. Prod. (2019) in press ; 1 - 17
by Mai E. Hussein , Amira S. El Senousy , Wessam H. Abd-elsalam , Kawkab A. Ahmed , Hesham I. El-askary , Samar M. Mouneir and Ahlam M. Fishawy

Abstract:  Roselle (Hibiscus sabdariffa L.) seeds, traditionally used in liver disorders, have recently attracted more attention as a new source of healthy edible oil with anti-inflammatory and antioxidant activities. However, its hepatoprotective effect has not been explored yet. In the current study, the hepatoprotective potential of roselle seed oil (RSO; 0.6, 4 and 8 ml/kg) and its nano-formulation (RSO-NE; 4 and 8 ml/kg), and their possible underlying mechanism were investigated in a paracetamol-induced hepatotoxicity rat model, compared to silymarin.  RSO and RSO-NE protected the liver against paracetamol-intoxication and maintained the overall architecture of liver tissues in a dose dependent manner. Additionally, hepatic nuclear factor-erythroid 2-related factor2 (Nrf2) and glutathione (GSH) increased significantly in pre-treated groups, while malondialdehyde (MDA) decreased. Moreover, RSO and RSO-NE significantly inhibited paracetamol-induced mRNA expression of pro-inflammatory cytokines (TNF-α and IL-6). Chemical analysis of RSO showed fatty acids (mainly linoleic, oleic, palmitic and stearic acids), n-eicosane, β-sitosterol and tocopherols as the major constituents, which contributed synergistically to its protective effect. The efficacy of RSO-NE (8 ml/Kg) was superior to its corresponding unformulated oil (0.6 ml/kg), indicating its enhanced bioavailability. These findings encourage the use of RSO in development of health promoting products such as food supplements, functional food and nutraceuticals for the prevention of liver disease.

DOI
http://doi.org/10.25135/rnp.133.19.03.1220
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Hepatoprotective Hibiscus sabdariffa Nanoemulsion Nrf2 Pro-inflammatory cytokines Tocopherols
Available online: June 07, 2019
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Original Article

8) Docking Studies and Antiprotozoal Activity of Secondary Metabolites Isolated from Scrophularia Syriaca Benth. Growing in Saudi Arabia

Rec. Nat. Prod. (2019) in press ; 1 - 8
by Abdulsalam A.M. Alkhaldi , Arafa Musa , Ehab M. Mostafa , Elham Amin and Harry P. De Koning

Phytochemical study of the ethanolic extract of Scrophularia syriaca Benth. was attained by chromatographic and spectroscopic procedures, which resulted in isolation of eight compounds; 6-O-α-L- rhamnopyranosylcatalpol (1), scropolioside B (2), gmelinoside-L (3), 8-acetyl harpagide (4), scropolioside D (5), scropolioside D2 (6), quercetin (7) and kaempferol-3-O-rutinoside (8). The antiprotozoal activity was evaluated against Trypanosoma brucei brucei (s427-WT), Trypanosoma brucei brucei (TbAT1-B48), Leishmania major and Leishmania mexicana. Compounds 2, 5, 7 and 8 exhibited mild to moderate activities against kinetoplastid parasites compared to pentamidine positive control, the mechanism of antiprotozoal activity was predicted by the molecular docking studies on the target enzyme Trypanosoma brucei glyceraldehyde-3-phosphate dehydrogenase (TbGAPDH).

DOI
http://doi.org/10.25135/rnp.19.03.1224
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
docking iridoids Leishmania Trypanosoma Scrophularia syriaca
Available online: June 05, 2019
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Original Article

9) Aspterrics A and B, New Sesquiterpenes from Deep Sea-derived Fungus Aspergillus terreus YPGA10

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Yuanli Li , Wan Liu , Wei Xu , Qin Li , Zhongbin Cheng and Xi Zeng

Two new sesquiterpenes, namely aspterric A (1) and aspterric B (2), together with aspterric acid (3), were isolated from the deep-sea-derived fungus Aspergillus terreus YPGA10. The structures of aspterrics A and B were determined by NMR and HRESIMS data. Biogenetically, aspterrics A and B were assumed to be the intermediates to derive aspterric acid.

DOI
http://doi.org/10.25135/rnp.131.19.04.1247
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Aspergillus terreus deep-sea-derived fungus sesquiterpenoids aspterrics A and B
Available online: May 28, 2019
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Original Article

10) 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

11) 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

12) 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

13) 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

14) 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

15) 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

16) 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

17) 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

18) 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

19) 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

20) 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

21) 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

22) 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

23) 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

24) 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

25) 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

26) 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

27) 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

28) 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

29) 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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