Records of Natural Products

Articles In Press

Short Report

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

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

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

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

2) Chemical composition of essential oils from leaves of six Piper species that grow in the Amazonia Biome, Brazil.

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

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

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

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

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

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

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

4) Chemical Composition and Anti-Candida and Anti- Trypanosoma cruzi Activities of Essential Oils from the Rhizomes and Leaves of Brazilian Species of Renealmia L. fil.

Rec. Nat. Prod. (2018) in press ; 1 - 13
by Kathlyn V. Gevú, Helena R.P. Lima, Ilzenayde A. Neves, Érica O. Mello, Gabriel B. Taveira, Laís P. Carvalho, Mário G. Carvalho, Valdirene M. Gomes, Edésio J.T. Melo and Maura Da Cunha
Abstract

This work aimed to determine the chemical composition of essential oils from rhizomes and leaves of Renealmia chrysotricha Petersen, R. breviscapa Poepp. & Endl. and R. nicolaioides Loes., and to evaluate the biological activities of these oils on three Candida species and the parasite Trypanosoma cruzi. The rhizomes and leaves were collected in the Atlantic and Amazon rainforests. Essential oils were isolated and characterized by gas chromatography. Βeta-Caryophyllene was found to be the most predominant compound in the essential oils of rhizomes and leaves of R. breviscapa, and the rhizomes of R. nicolaioides, whereas (E)-nerolidol was the most abundant compound in the oils of leaves of R. nicolaioides. In R. chrysotricha, α-terpineol, coronarin-E and 1,8-cineole were found to be the most predominant compounds in the essential oils of rhizomes, whereas cis-3-hexenol was predominant in the leaves. The tested oils did not inhibit C. albicans growth at 1000 µg/mL, whereas leaf oils from R. chrysotricha and R. nicolaioides inhibited the growth of C. buinensis and C. tropicalis by about 50%. Essential oils from the rhizomes and leaves of R. chrysotricha exhibited efficient antiparasitic activity against Trypanosoma cruzi. Damage to T. cruzi epimastigotes was confirmed by LM and TEM.

DOI
http://doi.org/10.25135/rnp.105.18.08.125
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Zingiberaceae rhizomes leaves terpenoids anticandidal activity antiparasitic activity.
Available online: November 01, 2018
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Original Article

5) Curcuma kwangsiensis Extracts Produced Antioxidant Effects Against Injury Induced by H2O2 on PC12 Cells

Rec. Nat. Prod. (2018) in press ; 1 - 14
by Juxiang Liu, Lianli Zhang, Jinyang Zhang, Baocai Li and Mi Zhang
Abstract

The radix of Curcuma kwangsiensis S. G. Lee & C. F. Liang (Zingiberaceae) is a traditional medicine in China, and used for treating qi stagnation and blood stasis. Previous chemical study showed it is rich in sesquiterpenoids and diarylheptanoids, similar to those in Curcuma longa L., which showed obviously protective effects against oxidative damage. However, the antioxidant and underlying mechanism of C. kwangsiensis has not been studied yet. In current study, the antioxidant activities of C. kwangsiensis extracts (ECWs), including 95 % EtOH extract (HCECW), 75 % EtOH extract (MCECW), methanol extract (MECW), dichloromethane extract (DECW) and petroleum ether extract (PECW), and their possible mechanisms, were studied on the model of H2O2-induced PC12 cell damage in vitro. The results showed different concentrations (1, 10, 50 µg/mL) of HCECW, MCECW and DECW could increase damaged PC12 cell viability significantly. In the extract-treated groups, the release rate of LDH significantly decreased, while SOD, CAT, and GSH markedly increased. In the meantime, the intracellular Ca2+ and cell apoptosis decreased significantly, while MMP increased and apoptosis morphology was clearly improved. Compared with the model group, they produced effects on up-regulating of Bcl-2, down-regulating of Bax and Caspase-3. Further, the chemical analysis of those five extracts by UPLC-DAD-Q-TOF-MS showed their major constituents were sesquiterpenoids and diarylheptanoids, indicating both of them presented in ECWs are antioxidant substances in this plant. This study provided an experimental basis for the future development of antioxidants from the genus Curcuma.

DOI
http://doi.org/10.25135/rnp.104.18.08.342
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Curcuma kwangsiensis antioxidant effect PC12 cell oxidative injury chemical analysi
Available online: October 28, 2018
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Original Article

6) New Diterpenes Isolated from the Colombian Caribbean Soft Coral Pseudoplexaura flagellosa and Their Cytotoxic Properties

Rec. Nat. Prod. (2018) in press ; 1 - 11
by Katherine Bauer, Mónica Puyana, Leonardo Castellanos and Edisson Tello
Abstract

Studies about secondary metabolites isolated from soft corals around the world have proven the potential of these organism as producers of compounds with a potent cytotoxic activity. In this work, we obtained the extract of Pseudoplexaura flagellosa collected in Santa Marta, Colombia, the cytotoxic activity of this extract, fractions and compounds was established against SiHa (ATCC® HTB-35™), MDA-MB-231 (ATCC® HTB26™), A549 (ATCC® CRM-CCL-185™), PC3 (ATCC® CRL1435), and L929 (ATCC® CCL1™) cell lines. The results showed that the extract of soft coral P. flagellosa has cytotoxic activity with an IC50 of 35.4, 72.3, 49.8 and 40.5 μg/mL against SiHa, A549, PC3 and MDA-MB-231 cell lines, respectively. Thus, this extract was repeatedly subjected to different chromatographic columns and final purification of these fractions afforded pure compounds 14, which were elucidated by 1D and 2D NMR experiments including 1H, 13C, COSY, HSQC, HMBC and NOESY, and HRESIMS. In addition, Mosher method was used to establish the stereochemistry of compound 2 and chemical interconversion allow establishing the stereochemistry of compound 1. These results let to conclude that compound 2 is a new stereoisomers of acetylated asperdiol previously reported on literature. Additionally, three analogues 5, 6, and 7 were synthesized from compound 1 and the cytotoxic activity of all compounds was evaluated using doxorubicin as positive control. The results showed that 6 (IC50 of 19.3, 23.7, 13.4 and 18.7 μg/mL against SiHa, A549, PC3 and MDA-MB-231, respectively) was the most active compound against all the cancer cell lines.

DOI
http://doi.org/10.25135/rnp.100.18.07.325.1
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pseudoplexaura flagellosa cytotoxic activity absolute stereochemistry stereoisomers soft corals
Available online: October 28, 2018
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Original Article

7) Bioactivity-Guided Isolation of Anti-Inflammatory Principles from Cistus parviflorus Lam.

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Perihan Gürbüz , Şengül Dilem Doğan , Gizem Nur Çelik , Hatice Bekci , Ahmet Cumaoğlu , Miyase Gözde Gündüz and Mehmet Yavuz Paksoy
Abstract

Bioactivity-guided fractionation and purification of Cistus parviflorus led to the isolation of two flavan-3-ol derivatives; gallocatechin (1) and epigallocatechin (2) and two flavonoid glycosides; avicularin (3) trans-tiliroside (4). The structures of the compounds were elucidated on the basis of NMR and ESIMS data. All compounds were isolated from C. parviflorus for the first time. Compounds 2 and 3 exhibited anti-inflammatory activity through decreasing the NOS2 and COX2 levels on LPS+IFN-γ treated RAW 264.7 cells. Molecular docking studies of avicularin, the most potent compound, were carried out in the active sites of NOS2 and COX2 to predict the most plausible binding modes and support the experimental data.

DOI
http://doi.org/10.25135/rnp.106.18.09.883
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cistaceae; inflammation; flavonoids; structure elucidation; avicularin; molecular modelling
Available online: October 24, 2018
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Original Article

8) Chemical Investigation and Bioactivity Screening of Salvia cassia Extracts

Rec. Nat. Prod. (2018) in press ; 1 - 11
by Belkıs Halfon, Özlem Çetin, Gamze Kökdil and Gülaçtı Topçu
Abstract

In this study the antioxidant and anticholinesterase activities of the crude ethanol extract, as well as the dichloromethane and water extracts obtained from partitioning of the crude ethanol extract, of the plant Salvia cassia Samuelss ex. Rech. Fil, were determined. The extracts were screened for their total phenolic and flavonoid contents. The dichloromethane extract, which showed higher inhibition of lipid peroxidation, higher metal chelating capacity and also a higher flavonoid content than the other extracts was analyzed for its constituents. GC-MS analysis resulted in the identification of a total of 30 long chain hydrocarbons. A series of b-amyrin fatty acid esters, a triterpene acid oleanolic acid, a diterpenoid manoyloxide, and two flavonoids apigenin 7, 4′-dimethyl ether and salvigenin were isolated by open column chromatography. Their structures were identified based on NMR and mass spectrometric techniques. The isolated compounds were also tested for their anticholinesterase activities. The triterpenoids as well as the water extract exhibited promising anticholinesterase activity.

DOI
http://doi.org/10.25135/rnp.99.18.05.291
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvia cassia antioxidant activity anticholinesterase activity fatty acid composition -amyrin fatty acid esters flavonoids.
Available online: October 16, 2018
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Short Report

9) Essential Oil Constituents from the Leaves of Anoectochilus setaceus, Codonopsis javanica and Aristolochia kwangsiensis from Vietnam

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Tran M. Hoi, Do N. Dai, Chu T. T. Ha, Ha V. Anh and Isiaka A. Ogunwande
Abstract

There are very few reports on the phytochemistry of Anoectochilus setaceus Blume, Codonopsis javanica (Blume) Hook. f. and Aristolochia kwangsiensis Chun & F.C.How ex S.Yun Liang species in the literature. Here we present essential oil compositions of the three endemic plants from Vietnam. The analysis of the chemical constituents of the hydrodistilled essential oils was achieved by using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The essential oils of A. setaceus, C. javanica and A. kwangsiensis afforded very low oil yields: 0.12%, 0.31% and 0.10% (v/w), respectively, calculated on a dry weight basis. The result indicated that the major components of the leaf oil of A. setaceus consist mainly of α-cadinol (17.1%), (E,E)-farnesol (14.0%) and terpinen-4-ol (11.0%) while β-pinene (20.8%) and α-pinene (15.4%) were the main compounds identified in C. javanica. However, the significant compounds of A. kwangsiensis were sabinene (34.8%), β-caryophyllene (8.8%) and terpinen-4-ol (8.6%). To the best of our knowledge this is the first report on the essential oil compositions of these species.

DOI
http://doi.org/10.25135/rnp.103.18.08.124
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Anoectochilus setaceus Codonopsis javanica Aristolochia kwangsiensis essential oil terpenoids.
Available online: October 16, 2018
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Original Article

10) Inhibitory Effects of Metabolites Isolated from Artemisia dracunculus L. Against the Human Carbonic Anhydrase I (hCA I) and II (hCA II)

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Tuba Aydın, Bayram Yurtvermez, Murat Şentürk, Cavit Kazaz and Ahmet Çakır
Abstract

Tarragon or Dragon's-wort (Artemisia dracunculus L.) is widely used as spice and in traditional medicine in various regions of the world. Inhibitory effects of the n-hexane, dichloromethane, ethanol and methanol extracts of the leaves of tarragon on the human carbonic anhydrase (hCA) I and II enzymes were investigated. Dichloromethane extract exhibited the strongest activity with lowest IC50 value (0.020 and 0.031 μg/mL, respectively). The chromatographic studies on the dichloromethane extract of tarragon allowed the isolation of six known strong inhibitors of hCA isozymes as trans-anethole, stigmasterol, herniarin, (2E,4E)-N-isobutylundeca-2,4-dien-8,10-diynamide, (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one and 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane. The compound, 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane was isolated from tarragon for the first time in this study. Among the tested compounds, 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane showed the highest inhibitiory impact on both hCA isozymes. Also its IC50 values were found lower than positive control, acetazolamide.

DOI
http://doi.org/10.25135/rnp.102.18.07.329
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Artemisia dracunculus L. 1-(4'-methoxyphenyl)-1 2 3-trihydroxypropane enzyme inhibition hCA I hCA II.
Available online: October 14, 2018
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Original Article

11) Phytochemical Profiles and Antioxidant Activity of Salvia species from Southern Italy

Rec. Nat. Prod. (2018) in press ; 1 - 11
by Marzia Vergine, Francesca Nicolì, Carmine Negro, Andrea Luvisi, Eliana Nutricati, Rita Annunziata Accogli, Erika Sabella and Antonio Miceli
Abstract

The purpose of this research was to investigate phytochemical profiles and antioxidant activity in four Salvia species growing in Salento (Southern Italy). The hydrodistillation products obtained from the aerial parts of Salvia clandestina, Salvia fruticosa, Salvia officinalis and Salvia sclarea were characterized by GC–MS and 50 compounds were detected. With the exception of S. clandestina, that did not produce essential oils, the other species shared different amounts of monoterpenes oxygenated (camphor 2.13%-9.16%) and sesquiterpenes hydrocarbons (caryophyllene 4.65%-18.33%; humulene 1.87%-12.39%). The phenolic profiling, analyzed by HPLC ESI/MS-TOF, highlights that S. clandestina is a rich source of danshensu (4.76 mg/g DW) while S. sclarea of rosmarinic acid (15.57 mg/g DW). Mutivariate statistical analysis (PCA) of hitherto studied Salvia phenols have shown similarities in profiles between S. fruticosa and S. officinalis, while S. clandestina and S. sclarea showed distinctive profiles. Otherwise, essential oil profiles analysed by PCA are clearly different among the three productive species. The extracts from collected plants were found to be effective antioxidant in three different in vitro assays (DPPH, ABTS, FRAP and Superoxide anion scavenging activity). Thus, they can be proposed as natural ingredients in functional foods, herbal medicines or as sources of bioactive molecules.

DOI
http://doi.org/10.25135/rnp.96.18.07.119
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvia clandestina L. Salvia fruticosa Mill. Salvia officinalis L. Salvia sclarea L. essential oils phenolic compounds.
Available online: October 10, 2018
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Original Article

12) Two New Lipodepsipeptides from the Endophytic Fungus Colletotrichum aotearoa Y41

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Yang Wu, Juanli Zhang, Wenxing Xiang, Mingzi Wang and Chunhua Lu
Abstract

Two closely related lipodepsipeptides, with the same 12-membered oxodepsipeptide ring system, aotearolides A (1) and B (2), together with 1H-indole-3-carbaldehyde (3) and 2-(1H-indol-3-yl)acetic acid (4) were isolated from the endophytic fungal isolate Colletotrichum aotearoa Y41 of Huperzia serrata. The structures were elucidated on the basis of their high-resolution ESI/MS, 1D and 2D NMR spectroscopic data.

DOI
http://doi.org/10.25135/rnp.90.18.05.298
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Lipodepsipeptide aotearolides A and B Colletotrichum aotearoa Huperzia serrata
Available online: October 08, 2018
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Short Report

13) Insecticidal Activity of Artemisia frigida Willd. Essential Oil and Its Constituents against Three Stored Product Insects

Rec. Nat. Prod. (2018) in press ; 1 - 3
by Zhe Zhang, Xue Pang, Shanshan Guo, Juqin Cao1, Yang Wang, Zhenyang Chen, Yixi Feng, Ning Lei and Shushan Du
Abstract

In this work, we investigated the chemical constituents of hydrodistillation essential oil from the aerial parts of Artemisia frigida Willd. All together 14 components were identified by GC-MS. Moreover, we tested the fumigant and contact activities of the essential oil and its five major individual compounds (terpinen-4-ol, verbenone, camphene, α-terpineol and α-terpinyl acetate) against Liposcelis bostrychophila, Lasioderma serricorne and Tribolium castaneum. In fumigant toxicity tests, α-terpineol possessed the strongest activity (LC50 = 3.27 mg/L air) against L. serricorne. Terpinen-4-ol exhibited the strongest activity (LC50 = 0.08 and 3.74 mg/L air respectively) against L. bostrychophila and T. castaneum. As for contact toxicity, terpinen-4-ol and α-terpinyl acetate exhibited fair toxicity against L. bostrychophila (LD50 = 33.10 and 31.80 µg/cm2 respectively) and L. serricorne (LD50 = 8.62 and 8.87 µg/adult respectively), and camphene possessed the strongest activity (LD50 = 5.13 µg/adult) against T. castaneum. The results indicated that A. frigida essential oil and its individual compounds had the potential to be developed as natural fumigants and insecticides for control of these three stored-product insects.

DOI
http://doi.org/10.25135/rnp.91.18.06.114
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Artemisia frigida Willd. essential oil fumigant activity contact activity stored-product insects GC
Available online: October 04, 2018
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Short Report

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

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Le Quoc Hung, Phuong Thien Thuong and Nguyen Huu Tung
Abstract

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: October 01, 2018
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Original Article

15) Cytotoxic Activity-Guided Isolation Studies on Fumana procumbens (Dunal) Gren. & Godr.

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Esra Emerce, Perihan Gürbüz, Şengül Dilem Doğan, Ela Kadioglu and Ipek Süntar
Abstract

Among the plant secondary metabolites much attention has been given to naturally occurring phenolic compounds as attractive candidates for cancer treatment and prevention. Fumana procumbens (Dunal) Gren. & Godr (Cistaceae) is a perennial herb, distributed in inner and southwest Anatolia, Turkey. F. procumbens was shown to be rich in phenolic constituents especially flavonoids and biflavonoids which are known for their antioxidant and anticarcinogenic effects. Thus, this study aims to investigate the anticancer activity of F. procumbens extracts, fractions and pure compounds by MTT test against HeLa, MCF-7, and A549 as well as BEAS-2B cell lines for determining selectivity. Bioactivity-guided phytochemical investigation on Fumana procumbens (Dunal) Gren. & Godr. led to the isolation and identification of three biflavonoids: genkwanol A, dihydrodaphnodorin B and stelleranol. The structures were elucidated by extensive 1D- and 2D-NMR spectroscopic analysis in combination with MS experiments. This is the first report on the isolation of genkwanol A and stelleranol from the genus Fumana and from the family Cistaceae. As a result, no individual cytotoxic activity was obtained for biflavonoid compounds. However, the former fractions FrC and FrD as well as MeOH and n-BuOH extracts exerted moderate and significant cytotoxic activity which suggested a possible synergistic effect.

DOI
http://doi.org/10.25135/rnp.98.18.07.331
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Anticancer activity Cistaceae Fumana procumbens cell viability cytotoxicity MTT test.
Available online: October 01, 2018
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Short Report

16) Chemical Constituents of Essential Oils Extracted from the Leaves and Flowers of Spiranthera odoratissima A. St. Hil. (Rutaceae)

Rec. Nat. Prod. (2018) in press ; 1 - 4
by Fernando Duarte Cabral 1, Cassia Cristina Fernandes Alves, Rodrigo Sebastião Cruvinel Cabral, Guilherme Brinker Willrich, Antônio Eduardo Miller Crotti and Mayker Lazaro Dantas Miranda
Abstract

Spiranthera odoratissima A. St. Hil. (Rutaceae), a plant grown in midwestern Brazil, has been used for treating rheumatism, infection and abdominal pain. This research aims to investigate chemical constituents of essential oils from S. odoratissima A. St. Hil. leaves and flowers. Essential oils were obtained by hydrodistillation and fully characterized by gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Results of the essential oil from S. odoratissima A. St. Hil. leaves showed that it has 28 volatile compounds which represent 93.8% of the oil. Its major compounds were b-caryophyllene (23.8%), bicyclogermacrene (10.8%), δ-cadinene (7.1%), germacrene D (5.9%), a-copaene (5.5%) and b-elemene (5.3%). Results of the essential oil from S. odoratissima A. St. Hil. flowers showed that it has 29 volatile compounds which represent 94.4% of the oil. Its main constituents were b-caryophyllene (14.1%), spathulenol (8.1%), g-cadinene (7.2%), α-cadinol (6.6%), a-copaene (6.4%), τ-muurolol (6.3%), δ-cadinene (5.8%), b-elemene (5.4%) and alloaromadendrene (5.2%). In this research, chemical constituents of the essential oil from S. odoratissima A. St. Hil. flowers were investigated for the first time.

DOI
http://doi.org/10.25135/rnp.95.18.07.117
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Spiranthera odoratissima A. St. Hil. Rutaceae essential oils -caryophyllene medicinal plant.
Available online: September 30, 2018
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Original Article

17) Triterpenoids from Acokanthera schimperi in Ethiopia

Rec. Nat. Prod. (2018) in press ; 1 - 7
by Wondwonsen A. Matebie, Wanchang Zhang, Shuo Zhang and Guangbo Xie
Abstract

The studies on the leaves of Acokanthera schimperi, a traditional herb of Ethiopia, afforded eight triterpenoids, including a new triterpenoid ester, lupan-20-ol-3(b)-yl 3-hydroxyoctadecanoate (1), along with seven known triterpenoids, lupeol (2), 28-nor-urs-12-ene-3b,17b-diol (3), ursolic aldehyde (4), 3b-hydroxy-oleana-11,13(18)-dien-28-oic acid (5), alagidiol (6), oleanolic acid (7) and ursolic acid lactone (8). ir structures were determined by spectroscopic methods including 2D NMR techniques and X-ray diffraction analysis.

DOI
http://doi.org/10.25135/rnp.94.18.07.324
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Acokanthera schimperi triterpenoids Ethiopian medicinal plants spectroscopic analyses X-ray diffraction.
Available online: September 30, 2018
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Original Article

18) Evaluation of the Antioxidative and Anti-inflammatory Effects of the Extract of Ribes mandshuricum (Maxim.) Kom. Leaves

Rec. Nat. Prod. (2018) in press ; 1 - 15
by Evaluation of the Antioxidative and Anti-inflammatory Effects of the Extract of Ribes mandshuricum (Maxim.) Kom. Leaves
Abstract

This study was designed to investigate the antioxidative and anti-inflammatory effects of the extract of Ribes mandshuricum (Maxim.) Kom. leaves. Seven major flavonoids (rutin, hyperoside, isoquercetin, trifolin, astragalin, quercetin and kaempferol ) were successfully prepared from the Ribes mandshuricum leaves by MAE-DES methods followed by X-5 macroporous resin. Then, the antioxidant activities of Ribes mandshuricum leaves flavonoids were evaluated by DPPH, ABTS and FRAP assays. We revealed that the Ribes mandshuricum leaves flavonoids had the antioxidant abilities. Finally, it was discovered that Ribes mandshuricum leaves flavonoids could effectively inhibit the NO production and increase the IL-10 cytokines production in LPS-induced RAW 264.7 cells. It suggested that the Ribes mandshuricum leaves flavonoids had the potential anti-inflammatory effects. Therefore, the major flavonoids of Ribes mandshuricum leaves have potential use as functional food or cosmetics to delay senescence, guard health and prevent chronic disease.

DOI
http://doi.org/10.25135/rnp.84.18.03.249
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Ribes mandshuricum (Maxim.) Kom. flavonoids antioxidant activity RAW264.7 macrophage anti-inflammatory activity.
Available online: September 30, 2018
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Original Article

19) A New Acylated Benzyl Alcohol Glucoside from Syzygium austroyunnanense

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Feng Li, Shaohua Xu, Yan Zhao, Mengjia Li, Wen Xu, Yikao Hu, Dingli Zhang and Yong Zhao
Abstract

A new acylated benzyl alcohol glucoside, benzyl alcohol 3',6'-di-O-galloyl-b-glucopyranoside (1), together with a known analogue, 6'-O-galloyl-b-glucopyranoside (2)  and a cyanogenic glucoside, 6‵-O-galloylprunasin (3) were isolated from the leaves of Syzygium austroyunnanense. Their structures were characterized based on the spectroscopic methods and comparison with literature. This is the first phytochemical study on Syzygium austroyunnanense.

DOI
http://doi.org/10.25135/rnp.85.18.04.277
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Syzygium austroyunnanense Myrtaceae acylated glycoside.
Available online: September 25, 2018
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Original Article

20) Composition of the Essential Oils of Two Endemic Helichrysum Species in Turkey

Rec. Nat. Prod. (2018) in press ; 1 - 7
by Mine Kürkçüoğlu, Hale Gamze Ağalar, Ahmet Aksoy, and Kemal Hüsnü Can Başer
Abstract

The aerial parts of Helichrysum noeanum Boiss. and H. chionophilum Boiss. et Balansa were hydrodistilled for 3 h using a Clevenger-type apparatus. The essential oils were analyzed by GC-FID and GC-MS, simultaneously. The main constituents were identified as hexadecanoic acid (25.3%), dodecanoic acid (17.8%), tetradecanoic acid (13.7%), and decanoic acid (4.2%) for H. noeanum. Decanoic acid (18.7%), tetradecanoic acid (16.9%), dodecanoic acid (13.8%), hexadecanoic acid (12.2%) and hexahydrofarnesyl acetone (3.2%) were found to be the major compounds for H. chionophilum. Several reports have been encountered in the literature dealing with the oil composition of several Helichrysum species. To the best of our knowledge, the essential oil of H. chionophilum has not previously been investigated.

DOI
http://doi.org/10.25135/rnp.93.18.06.113
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Helichrysum noeanum H. chionophilum essential oil GC GC-MS.
Available online: September 20, 2018
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Original Article

21) New Cytotoxic Metabolites from Pathogenic Fungus Cylindrocarpon destructans Associated with Meconopsis grandis

Rec. Nat. Prod. (2018) in press ; 1 - 7
by Dilfaraz Khan, Shah Iram Niaz, Kamran Tahir, Hidayat Ullah Khan, Muhammad Haroon, Shahid Ullah Khan, Syed Badshah, Shafiullah Khan, Muafia Jabeen and Liu Lan
Abstract

Phytochemical investigation on pathogenic fungus Cylindrocarpon destructans isolated form Meconopsisgrandis plant led to the isolation of two new isochromene derivatives namely, 6,8-dimethoxy-3-methyl-3,4-dihydrobenzoisochromene-4,9,10-triol (1) and 3,5,6-trihydroxy-4-methylbenzoisochromene-9,11-dione (2) along with four known compounds (3-6). The structures of these compounds were elucidated by 1D and 2D NMR and mass spectroscopic data analysis. The isolated compounds were evaluated for cytotoxic activity. The compounds 1-4 showed good inhibition against the growth of cell lines MCF-7 and PC-3. Compounds 5-6 showed minimum inhibitory effect of cancerous cell lines growth.

DOI
http://doi.org/10.25135/rnp.67.18.01.207
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pathogenic fungus Cylindrocarpon destructans Meconopsis grandis cytotoxic activity
Available online: August 27, 2018
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Original Article

22) In vitro Propagation and Volatile Compound Characterization of Lavandula stoechas L. subsp. stoechas- An Economically Important Source of Essential Oil

Rec. Nat. Prod. (2018) in press ; 1 - 8
by Sam Mokhtarzadeh, Betül Demirci, Hale Gamze Ağalar,Khalid Mahmood Khawar and Nese Kırımer
Abstract

The objective in this study is to isolate and characterize volatile compounds of Lavandula stoechas L. subsp. stoechas rooted with micropropagation techniques and grown under suitable in vitro conditions. Microdistillation procedure was applied on aerial parts of this plant. The volatile compounds were characterized by GC-FID and GC-MS systems, simultaneously. Based on results, twenty-two compounds were identified. Major volatile compounds included camphor (38.5%), bornyl acetate (10.6%), α-fenchone (8.9%), 1,8-cineole (4.3%), α-pinene (4.0%), linalool (3.5%), viridiflorol (3.8%) myrtenal (2.7%), geranyl acetate (2.1%). These results were positively related with data published regarding the plant growing wild.

DOI
http://doi.org/10.25135/rnp.86.18.04.105
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Lavandula stoechas subsp. stoechas tissue culture microdistillation volatile compounds.
Available online: August 04, 2018
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Original Article

23) Diterpenoid Alkaloids from the Roots of Aconitum sinomontanum and Their Evaluation of Immunotoxicity

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Jiao Zhang, Yuze Li, Yuwen Cui, Pu Jia, Zhenggang Yue, Bei Song and Xiaomei Song
Abstract

A new C 18-diterpenoid alkaloid, along with four known diterpenoid alkaloids have been isolated from the roots of Aconitum sinomontanum. Their structures were established as sinomontanine I (1), delcosine (2), lepenine (3), napelline (4), and kirinine B (5) by extensive spectroscopic techniques and chemical methods. The immunosuppressive effects of compounds 1 –4 were evaluated in vitro through ConA-induced or LPS-induced splenocyte proliferation, with IC 50 values of 8.909 μM, 1.515 μM , 5.078 μM, and 1.167 μM ( ConA-induced ) , or 3.661 μM, 4.417 μM, 5.129 μM, and 1.830 μM (LPS-induced), and compounds 1 –4 showed a significant cytotoxic effect with CC 50 values of 447.5 μM, 702.2 μM, 310.6 μM and 794.1 μM, respectively. The CC 50/IC 50 value of 2 and 3 suggested that these compounds were potential immunosuppressive agents for the treatment of autoimmune diseases characterized by arthritis, such as rheumatoid arthritis.

DOI
http://doi.org/10.25135/rnp.89.18.05.296
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Aconitum sinomontanum Nakai diterpenoid alkaloids immunotoxicity
Available online: August 04, 2018
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Original Article

24) Wound-Healing Activity of Some Species of Euphorbia L.

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Serkan Özbilgin, Esra Küpeli Akkol, İpek Süntar, Mehmet Tekin and Gülçin Saltan İşcan
Abstract

 Some species of Euphorbia have been used as medicinal plants to treat wounds, and skin diseases, around the world. The solvents n-hexane, ethyl acetate, and methanol were used successively to prepare extracts of the aerial parts of E. characias subsp. wulfenii, E. helioscopia,E. macrocladaE. seguieriana subsp. seguieriana, and E. virgata. Linear incision, circular excision wound models and the hydroxyproline assay method were used to assess the wound-healing activity. The inhibition of the increase in capillary permeability induced by acetic acid was used to assay the anti-inflammatory activity. The methanol extract of the aerial parts of E. characias subsp. wulfenii showed statistically significant wound-healing activity with 43.03% tensile strength for the linear incision wound model and a 65.24% reduction in the area of the wound by day 10 for the circular excision model. The tissue treated with this extract was found to contain 35.47 µg/mg of hydroxyproline. The methanol extract of E. characias subsp. wulfeniiinhibited inflammation induced by acetic acid with a value of 34.74%. The results showed that the aerial parts of E. characias subsp. wulfenii possess wound-healing and anti-inflammatory activities on different models.

DOI
http://doi.org/10.25135/rnp.81.18.03.255
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Euphorbia anti-inflammatory excision incision wound-healing .
Available online: July 18, 2018
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Original Article

25) Isomeric Phenolic Glycosides from from Populus tomentosa

Rec. Nat. Prod. (2018) in press ; 1 - 7
by Liang Xu, Haiping Liu, Yucui Ma, Cui Wu, Ruiqi Li and Zhimao Chao
Abstract

A new phenolic glycoside named salicyltomenside (1), with five similar compounds, salicyltremuloidin (2), tremuloidin (3), isograndidentatin A (4), siebolside B (5), and salicin (6) were isolated from Populus tomentosa Carr. Additionally, salicyltremuloidin (2) was obtained from the plant for the first time. Structure of the new compound was determined using spectroscopic methods including ESI-MS and 1D- and 2D-NMR. Others were elucidated through 1H and 13C NMR spectra and comparison with literature data. Notably, salicyltomenside (1) and salicyltremuloidin (2) were structural isomers.

DOI
http://doi.org/10.25135/rnp.82.18.03.257
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Populus tomentosa Carr. salicyltomenside salicyltremuloidin phenolic glycosides NMR.
Available online: July 13, 2018
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Short Report

26) Litsine A : A New A porphine A lkaloid from the Root Barks of Litsea glutinosa

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Yan Jin, Younan Wu, Yiying Li, Caiyun Zhang, Wanying Sun Lin Dongand Xiaopo Zhang
Abstract

 A new aporphine alkaloid, named Litsine A, along with two known ones were isolated from the root barks of Litsea glutinosa . The new structure was determined by various spectroscopic techniques including 1D ( 1 H-, 13 C-NMR) , 2D-NMR (HMBC, HSQC, COSY and R OESY) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) , where as the structures of the known compounds were elucidated through 1D-NMR, mass spectrometric analysis and compared with the reported data in literature. The effects of these compounds on glucose uptake in C2C12 myotubes were evaluated at the concentration of 10μM. The three compounds exhibited potent activity , with 1 as the best one, in increasing glucose uptake.

DOI
http://doi.org/10.25135/rnp.87.18.04.276
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Litsea glutinosa Litsine A aporphine alkaloid s glucose uptake activities.
Available online: July 13, 2018
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