Records of Natural Products

Articles In Press

Original Article

1) Antimicrobial Effect and Antioxidant Activity of Triterpenes Isolated from Gymnema sylvestre R. Br.

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Valeria Romanucci , Maria Giordano , Sergio Davinelli , Cinzia Di Marino , Afef Ladhari and Anna De Marco

Gymnema sylvestre is a commonly used herb in Ayurvedic medicine. The demand for its extracts in the commercial and pharmaceutical fields has been steadily increasing in recent years. Its extracts are used to treat various ailments as well as for their antimicrobial properties. This study has evaluated the antimicrobial effects of different G. sylvestre extracts and of eight triterpenes isolated from the most active extract on six bacterial poultry pathogens i.e. Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and Enterobacter aerogenes. In particular, it has been evaluated the minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) of all extracts and isolated triterpenes. Finally, the cytotoxicity activity of triterpenes was evaluated by MTT assay and their antioxidant activity in basal and oxidant conditions by DCFH-DA assay.

DOI
http://doi.org/10.25135/rnp.165.19.10.1448
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Gymnema sylvestre antimicrobial effects triterpenes gymnemic acids herbal drug DCFH-DA assay
Available online: January 13, 2020
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Original Article

2) Chemical Composition and Anticholinesterase Activity of the Essential Oil from the Ecuadorian Plant Salvia pichinchensis Benth

Rec. Nat. Prod. (2020) in press ; 1 - 10
by Melissa Salinas , Nicole Bec , James Calva , Jorge Ramirez , José Miguel Andrade , Christian Larroque , Giovanni Vidari and Chabaco Armijos

Salvia pichinchensis Benth was collected in the South of Ecuador and the essential oil (EO) was distilled from aerial parts and analyzed by GC-MS and GC-FID. The physical properties, chemical composition, and cholinesterase inhibitory activity were determined. Six major components, all sesquiterpenes, were identified: cis-cadina-1(6),4-diene (17.11%) (1),γ-curcumene (13.75%) (2), (E)-caryophyllene (12.58%) (3), (E,E)-α-farnesene (10.00%) (4), α-gurjunene (9.46%) (5) and allo-aromadendrene (6.96%) (6). The EO showed an interesting selective inhibitory activity against the enzyme butyrylcholinesterase (50.70 μg/mL) and only low inhibitory activity against acetylcholinesterase (117.60 μg/mL). The chemical composition and butyrylcholinesterase activity of the EO of S. pichinchensis Benth was reported for first time.

DOI
http://doi.org/10.25135/rnp.164.19.07.1342
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvia pichinchensis essential oil GC-MS analysis in vitro ChE inhibitory activity cis-cadina-1(6),4-diene
Available online: January 09, 2020
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Original Article

3) Novel Hopanoic Acid and Depside from the Lichen Dirinaria applanata

Rec. Nat. Prod. (2020) in press ; 1 - 8
by Nguyen Trong Tuan , Mai Van Hieu , Nguyen Quoc Chau Thanh , Huynh Van Loi , Huu Lai Nghia , Tran Thi Tuyet Hoa and Kanaori Kenji

From the extract of lichen Dirinaria applanata, two hopane derivatives including 1b-acetoxy-3b-hydroxy-21a-hopan-29-oic acid (1), hopane-3b, 6b, 21a-triol (2) and a depside namely 2-O¢-methylnordivaricatic acid (3) were isolated and identified by extensive analyzing 1D-NMR, 2D-NMR, HRESI-MS, and FT-IR. Notably, compound 1 and 3 were novel compounds while compound 2 was isolated from this lichen species for the first time.

DOI
http://doi.org/10.25135/rnp.161.19.10.1441
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Dirinaria applanata lichen hopan-29-oic acid depside
Available online: January 02, 2020
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Short Report

4) Two New Compounds from the Deep-Sea-Serived Fungus Aspergillus sp. YPGA8

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Meng-Hua Pan , Zhi-Yong Tian , Hui Yang , Wei Xu , Chen Pan , Zhongbin Cheng and Qin Li

Chemical examination of a fraction of the EtOAc extract of a marine-derived fungus Aspergillus sp. YPGA8 resulted in the isolation of two new compounds, namely aspertriols A-B (1-2). Compounds 1-2 possess an identical 2,3,4-trihydroxybutoxy moiety, which is rarely found in natural products. Their structures were determined by extensive analyses of spectroscopic data (1D and 2D NMR, HRESIMS). The bioassay study revealed that compounds 1 and 2 were inactive toward a-glucosidase.

DOI
http://doi.org/10.25135/rnp.162.19.11.1487
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
marine-derived fungus Aspergillus sp. YPGA8 aspertriols A-B isolation structure identification
Available online: December 20, 2019
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Original Article

5) Ent-kaurene Diterpenoids from Sideritis lycia with Antiviral and Cytotoxic Activities

Rec. Nat. Prod. (2019) in press ; 1 - 13
by Turgut Kılıç , Gülaçtı Topçu , Ahmet Ceyhan Gören , Zeynep Aydogmus , Ali Karagoz , Yasar Kemal Yildiz and Irfan Aslan

The genus Sideritis (Lamiaceae) is represented by 45 species (54 taxa) in Anatolia with high endemism ratio (74%), and Turkey is one of the gene centers of the genus along with Spain. Acetone extract of the aerial parts of Sideritis lycia afforded eight known ent-kaurene diterpenoids, structures of which have been identified as linearol, isolinearol, isosidol, sidol, siderol, sideridiol, 7-epi-candicandiol and foliol through 1H NMR, 13C NMR and mass spectroscopic analyses. Cytotoxic and antiviral activities of the acetone extract, linearol, sidol and isosidol were investigated together with insecticidal activity of species. antiviral index of linearol, isosidol and acetone extract of S. lycia were determined as 2.31, 2.01 and 2.58, respectively, except sidol. 7-Epi-candicandiol was found to be the most active diterpene against a series of cancer cell lines with ED50 values; KB (13.3 µg/mL), COL-2 (11.8 mg/mL), LU1 (17.9 mg/mL), LNCaP (14.9 mg/mL) and A2780 (9.0 mg/mL). Activity results of this study indicated that ent-kaurane diterpenes have potential to be considered as antiviral and cytotoxic lead compounds.

DOI
http://doi.org/10.25135/rnp.163.19.08.1373
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Sideritis lycia diterpenoid NMR and mass spectroscopy antiviral cytotoxic activity insecticidal activity
Available online: December 20, 2019
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Original Article

6) Bioactive Constituents from the Rhizomes of Sansevieria cylindrica

Rec. Nat. Prod. (2019) in press ; 1 - 8
by Hnin Thanda Aung , Mya Mu Aye , Zaw Min Thu , Yumiko Komori , Myint Myint Sein , Giovanni Vidari and Yoshiaki Takaya

Analysis of the MeOH extract of rhizomes of Sansevieria cylindrica using repeated silica gel and reversed-phase chromatographic separations led to the isolation of ten phenolic compounds (1-10) belonging to five different classes. Their structures, including the absolute configuration, were identified by NMR and CD spectra analysis. The antiradical activity of isolated compounds was tested using the DPPH scavenging method. The cytotoxic effects were assayed against a Hela cell line. Compounds 2-10 have been isolated from a Sansevieria species from the first time and compounds 4-10 have been isolated from species of the Asparagaceae family for the first time. The structure of a homoisoflavanone isolated from S. roxburghiana has been corrected.

DOI
http://doi.org/10.25135/rnp.160.19.10.1440
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Sansevieria cylindrica Asparagaceae homoisoflavanone cynnamoyl octopamine tyramine derivatives antiradical activity
Available online: December 19, 2019
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Original Article

7) 1H NMR-Based Metabolomics of Clinacanthus nutans Leaves Extracts in Correlation with Their Anti-neuroinflammation Towards LPS-Induced BV2 Cells

Rec. Nat. Prod. (2019) in press ; 1 - 17
by Amalina Ahmad Azam , Intan Safinar Ismail , Sharmili Vidyadaran , Faridah Abas and Khozirah Shaari

The metabolomics approach successfully explained the possible neuroprotective effect of Clinacanthus nutans (Burm. f.) Lindau (CN) leaf extracts. Forty-four metabolites were putatively identified via proton Nuclear Magnetic Resonance (1H NMR and J-resolved NMR) metabolic profiling of CN leaf extracts in three types of solvents, namely water, 50% ethanol, and ethanol. Metabolite fingerprinting has efficaciously differentiated aqueous between the other two extracts. The variable importance of projection (VIP) showed that 30 metabolites were responsible for the discrimination of the extracts by component 1 in the Partial Least Square (PLS) score plot. The lipopolysaccharides (LPS)-induced murine microglial of the BV2 cell line successfully exhibited aqueous CN as the closest extract related to the nitrite oxide (NO) inhibitory activity via PLS biplot, with an IC50 value of 336.2 ± 4.7 µg/mL through Griess assay. The cytotoxicity assay also indicated that all CN extracts were non-toxic. Schaftoside, acetate, propionate, alanine, and clinacoside C were identified as the most potential biomarkers in the anti-inflammatory assay. Hence, the aqueous CN extract could be further investigated, particularly relating to the anti-neuroinflammation study.

DOI
http://doi.org/10.25135/rnp.159.19.08.1384
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
1H NMR Clinacanthus nutans anti-neuroinflammation BV2 cells
Available online: December 15, 2019
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Short Report

8) Steroidal Components from the Roots and Rhizomes of Smilacina henryi and Their Cytotoxic Activities

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Zhenlin Chen , Xuanji Xue , Shuo Zhang , Rongxin Zhang , Xiulei Zhang , Zengjun Guo and Xin Zhang

Nine steroidal components, including a new pregnane glycoside (1), were obtained from the roots and rhizomes of Smilacina henryi. Their structures were determined via extensive spectroscopic data including, IR, HRESIMS and 1D, 2D NMR data analysis. Furthermore, their cytotoxic activities against human HepG2 and SW620 tumor cells were evaluated by the MTT method and compounds 2, 3, 5, 8 and 9 showed moderate activity with IC50 values raging from 18.4 to 86.3 μM.

DOI
http://doi.org/10.25135/rnp.156.1908.1390
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Smilacina henryi steroidal components structure identifition cytotoxicity
Available online: December 15, 2019
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Short Report

9) A New Oleanane Type Saponin from the Aerial Parts of Elaeocarpus hainanensis

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Huu Tung Nguyen , Quang Duong Pham , Dang Quang Le , Dinh Hoang Vu , Thuy My Nguyen Thi and Phuong Anh Dinh Thi

Elaeocarpus hainanensis has been used in the Oriental medicine but there are very few studies on its phytochemical profile. Our ongoing research on chemical constituents from Elaeocarpus plants in Vietnam led to the isolation of a new oleanane-type saponin from the aerial part of E. hainanensis. Its structure was identified as 1α-hydroxy-olean-11-oxo-12-en-3-O-β-L-arabinopyranoside (1) on the basis of extensive chemical and spectroscopic analyses including NMR and MS spectra. The occurence of the unique oleanane-type saponins in E. hainanensis contributed to impact phytochemical profile associated with chemotaxanomy meaning of the title plant.

DOI
http://doi.org/10.25135/rnp.160.19.09.1414
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Elaeocarpus hainanensis Elaeocarpaceae oleanane-type saponin 1α-hydroxy-olean-11-oxo-12-en-3-O-β-L-arabinopyranoside
Available online: November 25, 2019
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Short Report

10) Chemical Composition, Antibacterial and Cytotoxic Activities of the Essential Oil from Ficus tikoua Bur.

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Minyi Tian , Xiaoge Zhao , Xianghuan Wu , Yi Hong , Qi Chen , Xiongli Liu and Ying Zhou

The chemical composition and biological activities of the essential oil from Ficus tikoua Bur. were reported for the first time. Fifty-three compounds, accounting for 99.60% of the total essential oil composition, were identified and the main components were palmitic acid (51.13%) and linoleic acid (47.54%). The essential oil revealed significant antibacterial activity with the inhibition zones (7.89–10.59 mm), MIC (0.20–6.25 mg/mL) and MBC (0.20–12.50 mg/mL) against Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa and Proteus vulgaris. The essential oil exhibited significant cytotoxicity against A549, NCI-H1299, PC-3 and K562 tumor cells with the IC50 values of 131.08, 50.32, 120.58 and 31.68 μg/mL, respectively. The essential oil exhibited selective cytotoxic activity to human tumor cell lines, with a significantly lower cytotoxicity to human normal cell line (MRC-5, IC50 = 161.75 μg/mL) than to tumor cells. Additionally, palmitic acid, as the major compound, aslo revealed significant antibacterial and cytotoxic activities.

DOI
http://doi.org/10.25135/rnp.161.19.10.1450
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Ficus tikoua Bur. essential oil GC-MS palmitic acid antibacterial activity cytotoxic activity
Available online: November 25, 2019
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Short Report

11) A New Sesquiterpene and Known Alkaloids from Toddalia asiatica and Their Inhibitions Against Phosphodiesterase-4

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Ting-ting Lin and Gang Chen

A new sesquiterpene (1) and nine known alkaloids (2-10) were isolated from the roots of Toddalia asiatica. The structure of compound 1 were resolved by NMR and HRESI data, as well as ECD calculation for determining the absolute configuration. The known compounds were identified to be 8-acetonyldihydronitidine (2), 8-acetonyldihydroavicine (3), dihydronitidine (4), oxynitidine (5), decarine (6), skimmianine (7), g-fagarine (8), N-methylflindersine (9), and 4-methoxy-N-methyl-2-quinolone (10) by comparing the NMR data with those in the literature. Compound 1 is the first eremophilane-type sesquiterpenoid isolated from this species. The known compounds 2, 3, and 6 were discovered for the first time from the genus Toddalia. All the isolated compounds were evaluated for their inhibitory effects against phosphodiesterase-4, as result, compound 2 showed strong inhibitory effect against phosphodiesterase-4 with an IC50 value of 5.14 mM.

DOI
http://doi.org/10.25135/rnp.157.1907.1356
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Toddalia asiatica sesquiterpene alkaloids phosphodiesterase-4
Available online: November 23, 2019
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Short Report

12) Diterpenoids and Sesquiterpenoids from Syzygium fluviatile

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Dingli Zhang , Yikao Hu , Li Wang , Sheng-Xiong Huang , Yan Zhao , Mengjia Li , Feng Li and Yong Zhao

Abstract:  A new monocyclic diterpenoid, cassipouryl formate, (1) together with three known diterpenoids (24) and five known sesquiterpenoids (59) were isolated from the twigs and leaves of Syzygium fluviatile. The new isolate was elucidated by various spectroscopic technologies. This was the first example of the chemical constituents from this species and the first report on the diterpenoids from genus Syzygium.

DOI
http://doi.org/10.25135/rnp.158.19.08.1393
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Syzygium fluviatile Myrtaceae diterpenoids sesquiterpenoids.
Available online: November 11, 2019
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Short Report

13) Two New 2(1H)-Pyrazinone Derivatives from the Plant Endophyte Streptomyces sp. KIB-H1992

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Xiao-yan Ma , Zhouxin Zhang , Li Wang , Xinjun Hu , Xingyong Liu and Sheng-Xiong Huang

Two new 2(1H)-pyrazinone derivatives, 3,6-diisopropyl-5-methylpyrazin-2(1H)-one (1) and 5-(hydroxymethyl)-3,6-diisopropylpyrazin-2(1H)-one (2), were isolated from the fermentation broth of endophytic actinomycete Streptomyces sp. KIB-H1992. Their structures were established based on the detailed spectroscopic analyses, including ESI-MS, HR-ESI-MS, 1D- and 2D NMR spectra.

DOI
http://doi.org/10.25135/rnp.154.1907.1355
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
2(1H)-pyrazinone derivatives endophytic actinomycete Streptomyces sp. spectroscopic analyses
Available online: November 05, 2019
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Original Article

14) α-Pinene, Caryophyllene and β-Myrcene from Peucedanum terebinthaceum Essential oil: Insecticidal and Repellent Effects on Three Stored-Product Insects

Rec. Nat. Prod. (2019) in press ; 1 - 13
by Jiansheng Sun Sun , Yixi Feng , Yang Wang , Jigang Li , Kexing Zou , Hong Liu , Yichao Hu , Yun Xue , Longyan Yang , Shu-shan Du and Yan Wu

The aim of this work was to evaluate the bioactivities of Peucedanum terebinthaceum (Fisch.) Fisch. ex Turcz. essential oil and its three second rich constituents against Tribolium castaneum Herbst, Lasioderma serricorne Fabricius and Liposcelis bostrychophila Badonnel. The essential oil from aerial part of P. terebinthaceum was obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. Thirty-three constituents were confirmed by GC-MS, which accounting for 91.5% of the total oil. The principal constituents included β-thujene (21.4%), β-terpinene (11.8%), germacrene D (9.4%) and dihydro-cis-α-copaene-8-ol (8.0%). Besides, β-myrcene (6.2%), Linalyl isovalerate (4.3%), α-pinene (4.0%), caryophyllene (3.6%), (Z)-α-farnesene (3.6%) and β-elemene (3.0%) were also detected in relatively lower content. The essential oil possessed promising potential in pest control, as it showed strong contact toxicity and repellent effects on T. castaneum and L. serricorne. Three major constituents α-pinene, caryophyllene and β-myrcene were toxic to three insect species in contact assays and showed repellent effects on T. castaneum and L. bostrychophila. This work revealed the insecticidal capacity of P. terebinthaceum and would provide some information for the development of new strategies in the control of insect pests.

DOI
http://doi.org/10.25135/rnp.149.19.05.1287
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Fumigant toxicity Contact toxicity Tribolium castaneum Herbst Lasioderma serricorne Fabricius Liposcelis bostrychophila Badonnel
Available online: October 14, 2019
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Original Article

15) New Aromadendrane Sesquiterpenoid Pseuboydone F from the Marine-derived Fungus Pseudallescheria boydii F44-1

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Mei-xiang Yuan , Qi Guo , Yan-qin Ran , Yi Qiu , Wen-jian Lan and Hou-jin Li

A new aromadendrane sesquiterpenoid pseuboydone F (1), along with a known pseuboydone A (2), were isolated from the marine-derived fungus Pseudallescheria boydii F44-1 associated with the soft coral Sarcophyton sp.. The structures were elucidated by HRMS, 1D and 2D NMR spectroscopic data.

DOI
http://doi.org/10.25135/rnp.152.19.07.1343
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Marine fungus Pseudallescheria boydii aromadendrane sesquiterpenoid pseudboydone F
Available online: October 14, 2019
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Short Report

16) Mosquito Larvicidal Activity on Aedes albopictus and Constituents of Essential oils from Manglietia dandyi (Gagnep.) Dandy

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Pham H Ban , Le T Huong , Tran M Hoi , Nguyen H Hung , Le D Linh , Do N Dai and Isiaka Ajani Ogunwande

Herein, we report the results of our investigation on essential oils obtained by hydrodistilation of the leaves and fruits of Manglietia dandyi (Gagnep.) Dandy. The constituents of the oils were analyzed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The yields of the oils were 0.25% and 0.21% (v/w, leaf and fruit respectively), calculated on a dry weight basis. The main constituents of the leaf oils were (E)-nerolidol (18.4%) and α-selinene (11.0%) while the fruit oils contained abundance of β-caryophylene (27.7%), d-cadinene (13.7%), α-humulene (13.2%) and α-copaene (11.6%). The results indicated that M. dandyi leaf oil exhibited 96% and 100% mortality towards the fourth-instant larvae of Aedes albopictus at 24 h at tested concentrations of 50 µg/mL and 100 µg/mL. The oil only displayed 100% mortality at concentrations of 50 and 100 µg/mL and under 48 h. The minimum lethal concentrations, LC50, were 29.57 mg/mL (24 h) and 29.02 mg/mL (48 h); while the LC90 values of 46.21 mg/mL and 42.29 mg/mL were obtained respectively at 24 h and 48 h mg/mL. The chemical constituents and larvicidal action of M. dandyi essential oils are being reported for the first time.

DOI
http://doi.org/10.25135/rnp.151.19.07.1325
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Manglietia dandyi essential oil sesquiterpenes larvicidal activity Aedes albopictus
Available online: October 14, 2019
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Original Article

17) A New Sesquiterpene from Schisandra sphenanthera

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Kiem Van Phan , Nguyen Thi Mai , Hoang Thi Tuyet Lan , Bui Thi Mai Anh , Vu Van Doan , Bui Huu Tai and Nguyen Xuan Nhiem

A new sesquiterpene, schisandrathera E (1) and seven dibenzocyclooctadiene lignans as schisantherin D (2), schisantherin B (3), tigloylgomisin P (4), schisphenin E (5), angeloylgomisin H (6), (+)-deoxyschizandrin (7), and (+)-gomisin K3 (8) were isolated from the leaves of Schisandra sphenanthera Rehder & E.H.Wilson. Their structures were elucidated by spectroscopic and mass spectrometric analyses, including 1D-, 2D-NMR, HR-ESI-MS and ECD spectra. Compound 1 displayed moderate cytotoxicity against both PC3 and MCF4 cell lines in MTT assay with IC50 values of 22.60 and 7.80 µM, respectively.

DOI
http://doi.org/10.25135/rnp.153.19.09.1406
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Schisandra sphenanthera schisandrathera E sesquiterpene dibenzocyclooctadiene
Available online: October 14, 2019
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