Records of Natural Products

Year: 2020 Volume: 14 Issue:3 May-June

Original Article

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

Rec. Nat. Prod. (2020) 14:3 ; 166 - 170
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
Keywords
Marine fungus Pseudallescheria boydii aromadendrane sesquiterpenoid pseudboydone F
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© 2020 ACG Publications. All rights reserved.
Original Article

2) A New Sesquiterpene from Schisandra sphenanthera

Rec. Nat. Prod. (2020) 14:3 ; 171 - 176
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
Keywords
Schisandra sphenanthera schisandrathera E sesquiterpene dibenzocyclooctadiene
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© 2020 ACG Publications. All rights reserved.
Original Article

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

Rec. Nat. Prod. (2020) 14:3 ; 177 - 189
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
Keywords
Fumigant toxicity Contact toxicity Tribolium castaneum Herbst Lasioderma serricorne Fabricius Liposcelis bostrychophila Badonnel
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© 2020 ACG Publications. All rights reserved.
Original Article

4) Diterpenoids and Sesquiterpenoids from Syzygium fluviatile

Rec. Nat. Prod. (2020) 14:3 ; 190 - 195
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
Keywords
Syzygium fluviatile Myrtaceae diterpenoids sesquiterpenoids.
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Short Report

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

Rec. Nat. Prod. (2020) 14:3 ; 196 - 200
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
Keywords
2(1H)-pyrazinone derivatives endophytic actinomycete Streptomyces sp. spectroscopic analyses
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Short Report

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

Rec. Nat. Prod. (2020) 14:3 ; 201 - 206
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
Keywords
Manglietia dandyi essential oil sesquiterpenes larvicidal activity Aedes albopictus
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Short Report

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

Rec. Nat. Prod. (2020) 14:3 ; 207 - 212
by Tingting 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
Keywords
Toddalia asiatica sesquiterpene alkaloids phosphodiesterase-4
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Short Report

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

Rec. Nat. Prod. (2020) 14:3 ; 213 - 218
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
Keywords
Gymnema sylvestre antimicrobial effects triterpenes gymnemic acids herbal drug DCFH-DA assay
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Short Report

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

Rec. Nat. Prod. (2020) 14:3 ; 219 - 224
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
Keywords
Ficus tikoua Bur. essential oil GC-MS palmitic acid antibacterial activity cytotoxic activity
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Short Report

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

Rec. Nat. Prod. (2020) 14:3 ; 225 - 230
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
Keywords
Smilacina henryi steroidal components structure identifition cytotoxicity
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