Records of Natural Products

Articles In Press

Original Article

1) Secondary Metabolites of Ethanol Extracts of Pinus sylvestris Cones from Eastern Anatolia and Their Antioxidant, Cholinesterase and α-Glucosidase Activities

Rec. Nat. Prod. (2019) in press ; 1 - 10
by Meryem Topal

Scots pine (Pinus sylvestris) is the most widely distributed tree species among pine species.  Antiradical, antioxidant properties and inhibition properties on butyrylcholinesterase (BChE), acetylcholinesterase (AChE) and α-glycosidase activities of ethanol extracts of P. sylvestris were reported from  Sarikamis (Kars),  Gumushane and Erzurum provinces of  Turkey.  The cones of  P. Sylvestris from Gumushane showed the highest IC50 values in both DPPH. (14.75 µg/mL) and ABTS.+ (12.56 µg/mL) radical scavenging activities. An LC-HRMS method  developed and the secondary metabolite composition of extracts were identified.  The major  compounds are  determined as (+)-trans taxifolin, quercitrin, fumaric acid, (-) epicatechin, and nepetin-7-O-glucoside, apigenin-7-O-glucoside in P. sylvestris cones.

DOI
http://doi.org/10.25135/rnp.155.19.06.1326
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pinus sylvestris acetylcholinesterase butyrylcholinesterase antioxidant activity α-glucosidase LC-HRMS
Available online: November 12, 2019
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Short Report

2) 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 Zhao 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

3) 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

4) 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

5) 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

6) 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

7) 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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Short Report

8) Chemical Composition, Antibacterial, Antioxidant and Cytotoxic Activities of the Essential Oil of Dianella ensifolia

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Zi-qian He , Xue-yuan Shen , Ze-yu Cheng , Ruo-lan Wang , Peng-xiang Lai and Xiang Xing

TThe essential oil (EO) was isolated from aerial parts of Dianella ensifolia (L.) DC by hydro-distillation and its chemical constituents was determined by GC-FID and GC-MS. In total, sixty-three compounds comprising 97.2% of the EO were identified. The major compounds in D. ensifolia EO were found to be allo-aromadendrene (7.3%), geranylacetone (6.2%), hexahydrofarnesyl acetone (4.4%), longifolene (4.2%) and β-caryophyllene (4.0%). Besides, the essential oil was evaluated for its antibacterial activity by disc diffusion and broth microdilution method. The D. ensifolia EO exhibited a potential broad-spectrum in vitro antibacterial activity against both Gram-positive and Gram-negative bacteria. Also, antioxidant activities of the EO were examined by employing DPPH, ABTS as well as FRAP assays. A weak to moderate antioxidant activity of the EO was observed. Furthermore, in vitro cytotoxic activity evaluation against the cell lines HepG2 and MCF-7 by MTT method showed a potent cytotoxicity with IC50 values of 61.35 μg /mL and 56.53 μg /mL, respectively.  

DOI
http://doi.org/10.25135/rnp.150.19.07.1321
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Dianella ensifolia (L.) DC essential oil antibacterial activity antioxidant activity cytotoxic activity
Available online: October 14, 2019
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Short Report

9) Alkaloid Profiling of Hippeastrum cultivars by GC-MS, Isolation of Amaryllidaceae Alkaloids, and Evaluation of Their Cytotoxicity

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Latifah Al Shammari , Abdullah Al Mamun , Darja Koutova , Martina Majorosova , Daniela Hulcova , Marcela Safratova , Katerina Breiterova , Jana Marikova , Radim Havelek and Lucie Cahlíková

Different species, hybrids and varieties of the genus Hippeastrum (Amaryllidaceae) are planted for ornamental purposes and at the same time they represent a rich source of interesting secondary metabolites called Amaryllidaceae alkaloids. These compounds display a wide spectrum of biological activities. In the current study, six Hippeastrum taxa were evaluated for their alkaloid profile by GC-MS. Using preparative TLC, five alkaloids were isolated in pure form, and three of them evaluated for cytotoxic and antiproliferative potencies on a panel of human cancer cells of different histotype (Jurkat, MOLT-4, A549, HT-29, PANC-1, A2780, HeLa, MCF-7 and SAOS-2). In parallel, normal MRC-5 human fibroblasts were employed to determine the compounds´ overall toxicity against non-cancer cells. The most intriguing cytotoxic profile was demonstrated by montanine (1) with IC50 values between 1.04 – 1.99 µM.

DOI
http://doi.org/10.25135/rnp.147.19.06.1302
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Amaryllidaceae Hippeastrum alkaloids montanine cytotoxicity
Available online: September 11, 2019
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Original Article

10) A new 2,2′-dipyridine and Its Analogues from Endophytic Streptomyces sp. KIB H017c with Potent Cytotoxicity

Rec. Nat. Prod. (2019) in press ; 1 - 7
by Xiao-yan Ma , Feng-xian Yang , Can Su , Yijun Yan and Sheng-Xiong Huang

A new 2,2′-dipyridyl compound 1, along with three known analogues (24), was isolated from the culture broth of endophytic Streptomyces sp. KIB H017c derived from Fragaria ananassa. Their structures were elucidated by analysis of 1D and 2D NMR as well as HRESIMS data, and comparison with literature data. The biological properties of all isolates were explored for antibacterial, antifungal and cytotoxic activity. All four compounds exhibited weak antifungal activity against Saccharomyces cerevisiae, and compound 4 exhibited weak antifungal activity against Penicillium decumbens ATCC 10436. Compound 3 displayed moderate cytotoxic activity against HL-60 (human myeloid leukemia), SMMC-7721 (hepatocellular carcinoma), A-549 (lung carcinoma), MCF-7 (breast adenocarcinoma), and SW480 (colon carcinoma) with IC50 values of 12.10, 11.15, 23.64, 31.13 and 14.62 μM, respectively. Compound 4 exhibited potent activity against A-549 (lung carcinoma), MCF-7 (breast adenocarcinoma), and SW480 (colon carcinoma) with IC50 values 0.88, 0.34 and 0.55 μM, respectively.

DOI
http://doi.org/10.25135/rnp.147.19.05.1268
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Endophytic Streptomyces 2,2′-dipyridine antimicrobial activity cytotoxicity
Available online: September 11, 2019
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Original Article

11) The Efficacy of Gynostemma pentaphyllum Extract in Anti-obesity Therapy

Rec. Nat. Prod. (2019) in press ; 1 - 13
by Yoon Hee Kim , So Mi Kim , Jae Kyoung Lee , Sung Kwan Jo , Hyung Joong Kim , Kyu Min Cha , Cho Young Lim , Joo Myung Moon , Tae Young Kim and Eun Ji Kim

In the present study, we investigated a saponin-enriched fraction from Gynostemma pentaphyllum extract (GPE) and isolated gypenoside L (GL), gypenoside LI (GLI), and ginsenoside Rg3 (Rg3). To explore the anti-obesity activities of these compounds, we investigated the effects of GL, GLI, and Rg3 on glucose uptake and activation of AMPK in L6 skeletal muscle cells. GPE, GL, GLI, and Rg3 markedly increased glucose uptake activity and GLUT4 gene expression in L6 myotubes. The enhanced glucose uptake was mediated by the activation of the AMPK-ACC signaling pathway. In addition, we observed that GPE, GL, GLI, and Rg3 increased the expression of SIRT1 and PPARγ coacvtivator-1α (PGC-1α). Our results suggest the potential use of Gynostemma pentaphyllum in developing a therapeutic agent to reduce body weight and prevent diet-related diseases via glucose uptake and AMPK activation.

DOI
http://doi.org/10.25135/rnp.146.19.05.1270
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Gynostemma pentaphyllum gypenosides L6 skeletal muscle cells glucose uptake AMPK SIRT1
Available online: August 23, 2019
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Original Article

12) Bioassay Guided Isolation of Topoisomerase Ι Poison from Paphiopedilum callosum (Rchb.f.) Stein

Rec. Nat. Prod. (2019) in press ; 1 - 9
by San Yoon Nwe , Chayapol Tungphatthong , Areerat Laorpaksa , Boonchoo Sritularak , Witchuda Thanakijcharoenpath , Somboon Tanasupawat and Suchada Sukrong

Paphiopedilum callosum (Rchb.f.) Stein belongs to the Orchidaceae family. The phytochemistry and bioactivities of this plant have not been reported. In this study, a bioassay-guided isolation with a yeast cell-based assay was performed to isolate topoisomerase I poison compounds from the roots of P. callosum. One new and five known compounds were isolated. According to their spectroscopic data (ESI-MS, NMR, IR and UV), the new compound (1) is 3′-hydroxy-2,6,5′-trimethoxystilbene. The known compounds (2-6) were identified by comparing their spectroscopic data with those in the literature. According to the yeast cell-based assay, all the compounds were topoisomerase Ι poisons based on their ability to inhibit the growth of yeast cells. As further confirmation, the cytotoxic activities of the isolated compounds were evaluated using human cancer cell lines (MCF-7 and NCI-H187). The compounds exhibited varying degrees of cytotoxicity on the representative cell lines. These isolated compounds could serve as new lead compounds in the development of cancer chemotherapeutics.

DOI
http://doi.org/10.25135/rnp.144.19.06.1298
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Paphiopedilum callosum Orchidaceae yeast cell-based assay topoisomerase Ι poison stilbene
Available online: August 23, 2019
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Short Report

13) A New Record of the Marine Red Alga Laurencia snackeyi from Japan and its Chemotaxonomic Significance

Rec. Nat. Prod. (2019) in press ; 1 - 4
by Takahiro Ishii , Wakana Hisada , Tsuyoshi Abe , Norio Kikuchi and Minoru Suzuki

The constitution of Laurencia snackeyi (Weber-van Bosse) Masuda (Ryukyu-sozo in Japanese) from three locations, Minna Island, Sesoko Island and Kayo Coast in Okinawa Prefecture, Japan, is reported. This species produced snyderane-type sesquiterpenes, palisadin A (1), palisadin B (2) and aplysistatin (3) as characteristic metabolites. The species name of "Laurencia luzonensis Masuda", which has previously been reported in several papers, should be revised to L. snackeyi.

DOI
http://doi.org/10.25135/rnp.145.19.06.1310
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Laurencia snackeyi Laurencia luzonensis Rhodomelaceae chemotaxonomy snyderane-type sesquiterpene
Available online: August 23, 2019
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Original Article

14) Phytochemical Investigation of Endemic Sideritis cypria Post

Rec. Nat. Prod. (2019) in press ; 1 - 11
by Duygu Yiğit Hanoğlu , Azmi Hanoğlu , Hasan Yusufoğlu , Betül Demirci , Kemal Hüsnü Can Başer , İhsan Çalış and Dudu Özkum Yavuz

Non-polar and polar compounds were isolated from the leaves and chemical composition of the essential oil from aerial parts of Sideritis cypria endemic in Northern Cyprus was also determined. The structures of all the isolated compounds were elucidated by means of spectroscopic (UV, NMR: 1D and 2D-NMR: 1H, 13C, COSY, HSQC, HMBC) methods and comparison with literature data. The essential oil composition of the plant material was analysed by GC-FID and GC-MS, simultaneously. To the best of our knowledge, secondary metabolites of this endemic species were determined for the first time. As a result, two mixtures of four ent-kaurane diterpenes; sidol (1) and isosidol (2), linearol (3) and isolinearol (4); four phenylethanoid glycosides; verbascoside (5), lavandulifolioside (6), leonoside A (7), leucoseptoside A (8); four flavone glycosides, apigenin-7-O-glucopyranoside (9), isoscutellarein-7-O-[6'''-O-acetyl-allopyranosyl-(1->2)-glucopyranoside] (10) and a mixture of apigenin-7-O-(4''-O-p-coumaroyl)-glucopyranoside (11) and apigenin-7-O-(3''-O-p-coumaroyl)-glucopyranoside (12) were elucidated. 7-O-acetyl-8-epi-loganic acid (13), an iridoid glycoside, was reported herein for the first time for genus Sideritis. In addition, major compounds of the essential oil were determined as a-pinene (14.73±0.15%), b-pinene (16.60±0.20%), b-phellandrene (17.83±0.23%) and epi-cubebol (7.70±0.20%), respectively.

DOI
http://doi.org/10.25135/rnp.140.18.11.1079
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Sideritis Phytochemistry ent-kaurane diterpenes iridoids flavonoids essential oil
Available online: August 01, 2019
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Short Report

15) Melanin Synthesis Inhibitors from Olea europeae

Rec. Nat. Prod. (2019) in press ; 1 - 5
by Amira Elkattan , Ahmed Gohar , Mohamed Amer , Zain Naeem , Ahmed Ashour and Kuniyoshi Shimizu

The aim of this study was to discover more candidates for development of novel anti melanogenesis compounds from leaves of O. europeae. Seventeen compounds have been isolated from the leaves of O. europeae. The isolated compounds were identified as α, β-amyrin mixture (1), β-sitosterol (2), uvaol, erythrodiol mixture (3), oleanolic acid (4), maslinic acid (5), vomifoliol (6), β-sitosterol 3-O-β-D-glucoside (7), luteolin (8), oleoside dimethylester (9), oleuropein (10), hydroxypinoresinol 1-O-β-D-glucoside (11), luteolin-7-O-β-D-glucoside (12), diosmetin 7-O-β-D-glucoside (13), verbascoside (14), oleoside 11-methylester (15), secoxyloganin (16) and hydroxytyrosol 8-O-β-D-glucoside, hydroxytyrosol 4`-O-β-D-glucoside mixture (17). This is the first report on the identification of vomifoliol (6) in the oleaceae family. Results showed that several compounds other than oleuropein exhibited inhibition of melanin synthesis and at the same time with low cytotoxicity.

DOI
http://doi.org/10.25135/rnp.142.19.04.1264
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Olea europeae Melanin Vomifoliol
Available online: August 01, 2019
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Short Report

16) Chemical Constituents and Cytotoxic Activities of Essential Oils from the Flowers, Leaves and Stems of Zingiber striolatum Diels

Rec. Nat. Prod. (2019) in press ; 1 - 6
by Minyi Tian , Yi Hong , Xianghuan Wu , Min Zhang , Bing Lin and Ying Zhou

Abstract: The purpose of this study was to investigate chemical composition and cytotoxic activities of essential oils from Zingiber striolatum Diels flowers, leaves and stems. 73, 68 and 66 compounds representing 97.0%, 94.8% and 93.7% of flowers, leaves and stems essential oils were identified using GC-FID and GC-MS, respectively. The main constituents of the flowers oil were β-phellandrene (28.5%), α-humulene (14.7%), β-pinene (8.2%), β-elemene (5.5%), humulene oxide II (3.5%), cryptone (3.3%) and tricosane (3.2%). The predominant components in the leaves oil were hexahydrofarnesyl acetone (24.7%), α-humulene (12.2%), phytol (11.9%), humulene oxide II (6.3%), β-pinene (4.3%), sandaracopimaradiene (3.1%) and β-elemene (3.0%). The stems oil contained mainly α-humulene (15.6%), humulene oxide II (7.9%), hexahydrofarnesyl acetone (7.4%), phytol (7.2%), humulene oxide I (4.1%), β-elemene (3.8%) and 4-terpineol (3.2%). The cytotoxic activity against human leukemic (K562), prostatic carcinoma (PC-3) and lung cancer (A549) cell lines of essential oils was assessed using MTT assay. The essential oils of flowers, leaves and stems exhibited significant cytotoxicity against K562 (IC50: 12.94–37.89 μg/mL), PC-3 (IC50: 69.06–82.56 μg/mL) and A549 (IC50: 45.73–66.12 μg/mL) cell lines. This is the first report on the chemical constituents and cytotoxic activities of Z. striolatum flowers, leaves and stems essential oils.

DOI
http://doi.org/10.25135/rnp.143.19.05.1291
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Zingiber striolatum Diels essential oils GC-FID/MS cytotoxic activity
Available online: July 24, 2019
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