Records of Natural Products

Articles In Press

Original Article

1) Secondary Metabolites with Tyrosinase and Acetylcholinesterase Inhibitory Activities from Leonuri Fructus

Rec. Nat. Prod. (2021) in press ; 1 - 9
by Penghua Shu , Yuehui Luo , Huiqing Zhu , Yamin Li , Yingying Fei , Mengzhu Yu , Ting Xu , Yueyue Lou , Fugang Xiao and Jihong Huang

Fourteen secondary metabolites, including one cinnamate derivative (1), three spirocyclic nortriterpenoids (24), three phenylethanoid glycosides (57), four lignans (811) and three phenolic compounds (1214) were isolated from the EtOH extract of Leonuri Fructus. Their structures were elucidated on the basis of 1D NMR, 2D NMR and HR-ESI-MS data analysis. All isolates were tested for their antioxidant, tyrosinase and acetylcholinesterase inhibitory activities. Most of them showed moderate antioxidant activities. Compounds 24 exhibited obvious inhibitory activities against mushroom tyrosinase at 25 μM, with %inhibition values of 49.36 ±2.69%, 43.43 ± 3.35%, 51.69 ± 2.81%, respectively, with arbutin used as the positive control (51.90 ± 2.57%). Compounds 3, 56 and 910 exhibited significant inhibitory activities against acetylcholinesterase, similar to the positive control, galantamine

DOI
http://doi.org/10.25135/rnp.297.2110.2223
Keywords
Leonuri Fructus Leonurus japonicus nortriterpenoid phenylethanoid glycoside tyrosinase acetylcholinesterase
Available online: November 25, 2021
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Short Report

2) Cytotoxic Drimane-type Sesquiterpenoids from the Fungus Aspergillus flavipes 297

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Liancheng Xu , Shiping Wang , Xiang Ji , Changming Huang , Pengfei Hu , Weihuan Luo , Shan Liu , Yu Chen , Guodong Liu and Guanyi Cao

Chemical investigation of the marine-derived fungus Aspergillus flavipes 297 led to the isolation and identification of three drimane-type sesquiterpenoids, asperflavinoid A (1) and (6-strobilactone-B) esters of (E,E)-6,7-dihydroxy-2,4-octadienoic acids (2 and 3). Asperflavinoid A (1) was characterized as unseparated diastereomers and its chemical structure was determined by spectroscopic analysis of NMR and MS data. In the cytotoxic assay, compound 1 showed promising inhibitory effects on HepG2 and MKN-45 cell lines.

DOI
http://doi.org/10.25135/rnp.294.2109.2194
Keywords
Aspergillus flavipes natural products drimane sesquiterpenoids cytotoxicity
Available online: November 15, 2021
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Original Article

3) A New Iridoid Glucoside from the Stems of Myoporum bontioides (Sieb.et Zucc.) A. Gray

Rec. Nat. Prod. (2021) in press ; 1 - 7
by Tran Thi Minh , Nguyen Thi Viet Thanh and Vu Dinh Hoang

A phytochemical investigation of the stems of Myoporum bontioides (Sieb. et Zucc.) A. Gray, a semi-mangrove plant distributed along coastlines of north-eastern Vietnam and some Asian countries led to the isolation of a new iridoid glucoside (1), named myobontioside E, together with fourteen known compounds (2-15). Their structures were elucidated by means of HR ESI-MS, 1D and 2D NMR spectroscopy as well as comparison with the data reported in the literature. The cytotoxic effects on 8505C, MKN7, HT29, and T24 cell lines were assessed using SRB assay. Only iridoid 2 exhibited weak cytotoxicity against all tested cell lines with IC50 values ranging from 60.19 to 69.14 µM.

DOI
http://doi.org/10.25135/rnp.296.2108.2191
Keywords
Myoporum bontioides Myoporaceae iridoid glucoside dammarane saponin cytotoxicity
Available online: November 15, 2021
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Short Report

4) Sesquiterpenoids and Diterpenoids from the Flowers of Nicotiana tabacum L. and Their Antifungal Activity

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Kuo Xu , Jiao Wang , Jing Liu , Lin Ni , Yongmei Du and Xiaoyi Wei

Two new guaiane-type sesquiterpenoids, nicotiasesquiterpenes A (1) and B (2), and seven known cembrane-type diterpenoids (39), were isolated from glandular trichome secretions of fresh flowers of Nicotiana tabacum L. These new chemical structures were established by extensive analyses of HRESIMS and 1D and 2D NMR data, while the other structures were elucidated by comparison of 1D NMR data with those reported in the literature. All of the isolated compounds were tested for their antiphytopathogenic fungal activity against Valsa mali var. mali, Alternaria porri, and Botrytis cinerea at a concentration of 10 µg/mL. Compounds 3, 4, and 5 exhibited medium antifungal effects against Valsa mali var. mali, with inhibitory rates of 45.3±16.1, 53.4± 4.6, and 40.1±4.5%, respectively, while the other compounds showed only insignificant activities.

DOI
http://doi.org/10.25135/rnp.293.2109.2211
Keywords
Nicotiana tabacum Valsa mali var. mali Alternaria porri Botrytis cinerea antifungal activity
Available online: November 15, 2021
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Short Report

5) A New Short Chain Acetamide from the Biosphere and Bioactive Glycerolipids Extracted from the Marine Bibalve Codakia orbicularis (Lucinidae).

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Francesca Goudou , Olivier Grovel , Olivier Gros , Ali Al-mourabit , Céline Moriou and Philippe Petit

The marine bivalve Codakia orbicularis, harbors endosymbiotic bacteria located in its gill filaments. Bioassay-guided fractionation of an ethyl acetate extract of the gill tissues led to antibacterial fractions (against Gram positive and negative bacteria). The fraction eluted in AcOEt/ MeOH 90:10 displayed the greatest bioactivity. This fraction was analyzed using usual chromatographic and spectrometric methods and revealed three compounds. The first one (compound 1) was an acetamide isolated for the first time from the biosphere. The other two were mono-glycerolipids (compound 2) and (compound 3) with at the position sn-2 of their glycerol monounsaturated fatty acid chains (respectively C18:1Δ9 and C16:1Δ9). Compounds 2 and 3 showed bacteriostatic activity against two pathogenic Gram-negative bacteria using a disc diffusion assay method. These molecules have been isolated for the first time from a bivalve. Further investigations are currently in progress, so as to understand the role of these bioactive compounds into the regulation of C. orbicularis’ endosymbionts and/or to free-living pathogens.

DOI
http://doi.org/10.25135/rnp.295.2108.2194
Keywords
Antibacterial activity monoacylglycol ceramide
Available online: November 15, 2021
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Short Report

6) A New Isoflavan Glucoside from the Roots of Astragalus membranaceus var. mongholicus

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Yadong Wang , Chao Wang , Yuanhao Wang , Qing Hu and Fenghuan Wang

A new isoflavan glucoside, namely astramemside A (1), together with six known compounds (2-7) were obtained from the roots of a traditional Chinese medicine, Astragalus membranaceus var. mongholicus. Their structures were elucidated by spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR), and the absolute configuration of 1 was determined by combination of chemical transformation and single-crystal X-ray diffraction. Compound 1 showed moderate inhibition on nitric oxide (NO) production induced by lipopolysaccharide in RAW264.7 cells with an IC50 value of 38.98 ± 5.28 uM.

DOI
http://doi.org/10.25135/rnp.292.2109.2203
Keywords
Astragalus membranaceus var. mongholicus Leguminosae isoflavan glucoside
Available online: November 08, 2021
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Original Article

7) Two New Bibenzyls from Dendrobium hercoglossum

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Lei Cheng , Yike Fang , Huiling He , Maosheng Zhang , Minjian Dong , Chengxin Sun and Shiji Xiao

Two new bibenzyl compounds 3-hydroxy-4, 5, 3′-trimethoxybibenzyl (1) and (R)-4-hydroxy-3, 5, 3′, α-tetramethoxybibenzyl (2), along with twelve known compounds (314), were isolated from the stems of Dendrobium hercoglossum Reichb. f. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. The cytotoxic effects of the isolated compounds on two human tumors cell lines (MDA-MB-231 and Hela) were evaluated by the MTT assay.

DOI
http://doi.org/10.25135/rnp.291.2109.2198
Keywords
Orchidaceae Dendrobium hercoglossum bibenzyl cytotoxicity
Available online: November 02, 2021
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Short Report

8) Insecticidal and Repellent Activities of Volatile Constituents from Litsea dilleniifolia P. Y. Pai et P. H. Huang Against Stored-Product Insects

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Yuan Tian , Hui Fan , Yang Wang , Yu Zheng , Dongmei Hu and Shu-shan Du

The volatile oil from leaves of Litsea dilleniifolia P. Y. Pai et P. H. Huang was obtained by hydrodistillation. The qualitative and quantitative analysis of volatile constituents were performed by GC/MS and GC/FID. The volatile oil along with two major components was evaluated for their fumigant, contact toxicity and repellency against stored-product insects, namely Tribolium castaneum and Liposcelis bostrychophila. The volatile oil mainly contained decanal (48.4%), eremanthin (10.4%), zerumbone (10.1%) and estragole (9.2%). In bioassays, L. dilleniifolia volatile oil showed toxicity and repellent activities against T. castaneum and L. bostrychophila. The volatile oil, decanal and estragole at 78.63 nL/cm2 could cause 82-92% repellency against T. castaneum at 4h post-exposure. Among them, decanal (LC50 = 3.90 mg/L air) and estragole (LC50 = 5.33 mg/L air) had significant fumigant toxicity against T. castaneum, and estragole was strongly toxic to L. bostrychophila (LC50 = 0.61 mg/L air). The two components displayed a similar level of toxicity against T. castaneum in contact assays (LD50 = 21.91 and 20.41 µg/adult, respectively). This work indicates that L. dilleniifolia is promising to be developed as botanical insecticides and repellents to control pest damage in warehouses and storage rooms.

DOI
http://doi.org/10.25135/rnp.290.2108.2157
Keywords
Botanical insecticides Liposcelis bostrychophila repellency Tribolium castaneum the volatile oil toxicity
Available online: November 02, 2021
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Original Article

9) Monoester-Type C19-Diterpenoid Alkaloids from Aconitum carmichaelii and Their Cardiotoxicity

Rec. Nat. Prod. (2021) in press ; 1 - 11
by Qiao Lin , Chunwang Meng , Jie Liu , Qinmei Zhou , Xingjie Ding , Lulin Miao , Xiaoya Wang , Ou Dai and Cheng Peng

A new (1) and six known (2-7) monoester-type C19-diterpenoid alkaloids were isolated from the lateral roots of Aconitum carmichaelii Debx. Their structures were determined by spectroscopic techniques and calculations of NMR chemical shifts. Compound 1 (1-epi-hokbusine A) was an aconitine-type diterpenoid alkaloid possessing an unusual 1β-methoxy group. According to the main toxicity of the lateral roots of A. carmichaelii, the cardiotoxic effects of the isolates were evaluated using H9c2 rat myocardial cells and zebrafish embryos. The results showed that all the monoester-type C19-diterpenoid alkaloids exhibited cardiotoxicity, and compound 6 was found to be the most toxic compound.

DOI
http://doi.org/10.25135/rnp.287.2107.2127
Keywords
Aconitum carmichaelii monoester-type C19-diterpenoid alkaloids H9c2 cells zebrafish embryos cardiotoxicity
Available online: October 25, 2021
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Original Article

10) Two New Seco-Abietanoids with Xanthine Oxidase Inhibitory Activity from Cryptomeria japonica D. Don

Rec. Nat. Prod. (2021) in press ; 1 - 8
by Chi-I Chang , Cheng-Chi Chen , Sheng-Yang Wang , Jih-Jung Chen , Chiy-Rong Chen , Che-Yi Chao and Yueh-Hsiung Kuo

Two new seco-abietanoids, 12-hydroxy-6-nor-5,6-secoabieta-8,11,13-trien-7-oic acid (1) and 7-hydroxy-7,8-secoabieta-8,12-diene-6,11,14-trione (3), together with one known seco-abietanoid, 12-hydroxy-6-nor-5-oxo-5,6-secoabieta-8,11,13-trien-7-al (2), were isolated from the methanol extract of the bark of Cryptomeria japonica. Their structures were elucidated by mean of spectroscopic analysis, as well as on  comparison of NMR data with those of known analogues. At a concentration of 50 μM, compounds 13 showed inhibitory activity toward xanthine oxidase by 38.2%, 55.9%, and 23.0%, respectively.

DOI
http://doi.org/10.25135/rnp.289.2106.2121
Keywords
Cupressaceae Cryptomeria japonica bark diterpenoid
Available online: October 25, 2021
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Short Report

11) A New Iridoid Glycoside Isolated from Valeriana officinalis L.

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Guoqing Wu , Zilong Zhang , Hao Fan , Dongdong Zhang , Wenli Huang , Huawei Zhang , Yuze Li and Xiaomei Song

A new iridoid glycoside, (5S,7S,8S,9R)-7- hydroxy-∆4,11-dihyronepeta-1,3-diol-8-O-β-D-glucopyranosyl (1), along with 5 known compounds, dioscoridin A (2), jatamanin J (3), longiflorone (4), apigenin-8-O-β-D-glucopyranoside (5), isosakuranetin-5-O-rutinoside (6), were isolated from the Valeriana officinalis L. Their structures were determined by extensive analysis using various spectroscopic techniques. Moreover, the cytotoxic activity assay toward three human tumor cell (A549, HCT116 and SW620) lines were evaluated by the MTT method in vitro for compounds 1-2, using cisplatin as positive control. Experimental results showed that these compounds displayed weak cytotoxicity in the human cancer cell lines. Notably, compounds 2, 3 and 6 were firstly isolated from this plant, compound 4 was isolated from the genus Valeriana for the first time, compound 5 was isolated for the first time from Valerianaceae family.

DOI
http://doi.org/10.25135/rnp.283.2107-2145
Keywords
Iridoids Valeriana officinalis L. Valerianaceae cytotoxicity
Available online: October 25, 2021
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Original Article

12) Honeybee Propolis Phenol, Caffeic Acid Phenethyl Ester, Attenuates Cisplatin-Induced Kidney Damage – a Multitarget Approach

Rec. Nat. Prod. (2021) in press ; 1 - 14
by Branka Mitic , Dusan Mitic , Milica Radic , Milica Stankovic , Mihailo Sokolovic , Jelena Milovanovic , Nebojsa Arsic and Dusan Sokolovic

Cisplatin utilization is known to be limited due to numerous side effects, especially to the ones related to kidney tissue injury. The application of antioxidants, as potential supportive drugs, to prevent oxidative cisplatin tissue damage appears intuitive. In this work, we explored the usage of caffeic acid phenethyl ester (CAPE) in this respect through the analysis of standard serum biochemical parameters and the ones related to oxidative tissue damage, the changes in arginine metabolism, and apoptosis occurrence that follow cisplatin application in rat kidneys. Additionally, pathohistological analysis and a specific TUNEL staining for the detection of apoptosis was studied. Cisplatin produced marked changes in serum parameters that reflect kidney tissue function, while at the same time produced extensive tissue oxidative damage, increased arginase activity, and depleted reduced glutathione. Moreover, both biochemical and micromorphological analyses indicated significant tubular cell apoptosis. The application of CAPE together with cisplatin prevented the disturbance in serum biochemical and tissue oxidative stress parameters, without affecting arginase activity. Interestingly, CAPE inhibited different enzymes involved in the glutathione metabolism and the apoptotic process. The results of the present study indicate that CAPE could be used as supportive therapy for oncological patients receiving cisplatin since it attenuates the nephrotoxicity of this chemotherapeutic.

DOI
http://doi.org/10.25135/rnp.284.2107.2146
Keywords
Caffeic acid phenethyl ester kidney cisplatin oxidative damage arginase apoptosis
Available online: October 14, 2021
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Review Article

13) Current Techniques For The Search For Natural Products In Actinobacteria

Rec. Nat. Prod. (2021) in press ; 1 - 19
by Janette Berenice Gonzalez-Nava , Scarlett Alonso-Carmona , Gauddy Lizeth Manzanares-Leal , Horacio Sandoval-Trujillo and Ninfa Ramírez-Durán

The actinobacteria, also referred to as actinomycetes, have been the most widely used bacteria to produce industrial interest compounds due to their great biosynthetic capacity to generate structural diversity molecules. The actinobacteria with the most significant biosynthetic potential are the genus Streptomyces, Saccharopolyspora, and Micromonospora containing groups of biosynthetic genes such as polyketide synthase systems, non-ribosomal peptide synthase systems, terpenoid systems, ribosomally synthesized and post-translationally modified peptide systems, among others. This review focuses on genomic mining techniques and current helpful software to search for new natural products in actinobacteria. Currently, molecular techniques have been developed to improve the isolation of natural products, and bioinformatics programs, many are free to access, have been designed to analyze genes and microbial genomes that predict new molecule production. Thanks to these techniques, new natural products of industrial interest have been found in rare actinobacteria such as Nocardia and Rhodococcus.

DOI
http://doi.org/10.25135/rnp.286.2107-2132
Keywords
Actinobacteria Bioinformatics Genomic mining Natural products
Available online: October 14, 2021
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Original Article

14) Essential Oil Composition and Antioxidant Activity of Endemic Achillea lingulata Waldst. & Kit. Compared to Common A. millefolium L.

Rec. Nat. Prod. (2021) in press ; 1 - 11
by Dušan Čulum , Amira Čopra-Janićijević , Edina Muratović , Sonja Siljak-Yakovlev , Milka Maksimović and Danijela Vidic

In this study, the chemical composition and antioxidant activity of the hydrodistilled essential oil of Achillea lingulata, an endemic species of the Euro-Mediterranean region, originating from Bosnia and Herzegovina, was investigated for the first time. For comparison, an analysis of the essential oil of the widely distributed Achillea millefolium, which grows together in the same habitat, was made. Ninety-six components were identified in A. lingulata and A. millefolium oils comprising 97.8% and 85.8%, of the total oil, respectively. The oil of A. lingulata was characterized by a high content of oxygenated monoterpenes (76.8%). The main compounds were borneol (30.1%), trans-verbenol (15.5%), 2-tridecanone (12.2%), fragranol (8.3%), and myrtenol (7.9%). In contrast, essential oil of A. millefolium had oxygenated sesquiterpenes (60.8%) as the most abundant compounds, with elemol (32.9%) as the main constituent. In addition, γ-eudesmol (12.9%), caryophyllene oxide (7.7%), trans-caryophyllene (5.7%) and γ-muurolene (4.7%) were present in a significant percentage in A. millefolium oil. Antioxidant activity was tested by three methods, ABTS, DPPH and FRAP, and the obtained results showed low activity of both investigated oils.

 

DOI
http://doi.org/10.25135/rnp.285.2107.2143
Keywords
Achillea lingulata Achillea millefolium GC-MS essential oil terpenes antioxidant activity
Available online: October 09, 2021
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Short Report

15) Annonaceae Essential Oils: Antimicrobial and Compositions of the Leaves of Uvaria hamiltonii Hook. f. & Thoms. and Fissistigma kwangsiensis Tsiang & P. T. Li

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Le Thi Huong , Nguyen Thanh Chung , Dao Thi Minh Chau , Do Ngoc Dai and Isiaka Ajani Ogunwande

In this study, essential oils hydrodistilled from the leaves of Uvaria  hamiltonii Hook. f. & Thoms. and Fissistigma kwangsiensis  Tsiang & P. T. Li (Annonaceae) collected in Vietnam were analyzed by gas chromatographic techniques, and screened for the antimicrobial activities. The composition of both essential oils was dominated by sesquiterpenoids (70.0% and 78.7%, respectively). The main constituents of U. hamiltonii were germacrene D (22.9%), β-caryophyllene (21.1%), bicyclogermacrene (11.2%) and caryophyllene oxide (8.6%). The essential oil of F. kwangsiensis  also showed abundant sesquiterpenes β-caryophyllene (24.5%), d-cadinene (13.4%) and α-copaene (5.6%), but also included (Z)-β-ocimene (6.7%). The leaf oil of U. hamiltonii demonstrated notable antimicrobial activity against Enterococcus faecalis ATCC299212 with minimum inhibitory concentration (MIC) value of 7.99 µg/mL and Bacillus cereus ATCC14579 (MIC 5.67 µg/mL) while F. kwangsiensis  showed the most potent activity towards Pseudomonas aeruginosa ATCC27853 and Candida albicans ATCC10231, with MIC values of 3.45 µg/mL and 16.45 µg/mL, respectively. Both essential oils should be considered for further investigation as renewable “green” antimicrobial agents.

DOI
http://doi.org/10.25135/rnp.281.2108-2161
Keywords
Antimicrobial activity essential oil composition sesquiterpenes
Available online: October 09, 2021
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Original Article

16) Chemical Constituents and Biological Activity of the Stems of Adinandra hainanensis Hayata

Rec. Nat. Prod. (2021) in press ; 1 - 7
by Vu Thi Kim Oanh , Huu Giap Tran , Thu Ha Bui , Thi Lan Phuong Diep , Thi Van Anh Nguyen and Le Nguyen Thanh

Phytochemical study of Adinandra hainanensis stems led to the isolation of a new triterpene lupan-3β,20-dihydroxy-28-carbaldehyde (1) and eleven known compounds 2-12. The stems of A. hainanensis was rich in lupane-type triterpenes, especially betulinic acid (9) was abundant (around 0.45% w/w). The isolated triterpenes, including new compound 1 showed strong α-glucosidase inhibitory activity with IC50 values ranging of 2.27 ± 0.05 μg/mL to 12.25 ± 0.36 μg/mL. In the cytotoxic evaluation, betulinic acid, the major component, showed good cytotoxic activity against all tested cancer cell lines while new compound 1 was weakly active.

DOI
http://doi.org/10.25135/rnp.282.2108.2158
Keywords
Adinandra hainanensis lupane triterpene betulinic acid α-glucosidase cytotoxicity
Available online: October 09, 2021
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Original Article

17) Quantitative Analysis and In Silico Molecular Docking Screening for Acetylcholinesterase Inhibitor and ADME Prediction of Coumarins and Carbazole Alkaloids from Clausena harmandiana

Rec. Nat. Prod. (2021) in press ; 1 - 12
by Bunleu Sungthong , Kingkaeo Sithon , Panyada Panyatip , Sarin Tadtong , Nadtanet Nunthaboot and Ploenthip Puthongking

Coumarins and carbazole alkaloids are natural compounds, often with neurological properties, especially as acetylcholinesterase inhibitors. In order to screen the candidate anti-acetylcholinesterase agents, in-silico molecular docking was performed aiming to predict the binding mechanism and the results were used to identify pharmacophores of coumarins and carbazole alkaloids from Clausena harmandiana as AChE inhibitory activity. All isolated compounds are xanthoxyletin (1), dentatin (2), nordentatin (3), clausarin (4), 7-methoxymukonal (5), 7-methoxyheptaphylline (6) and heptaphylline (7) displayed the stable binding interactions with Torpedo californica acetylcholinesterase (TcAChE) enzyme via π-π interactions, hydrogen bonds and hydrophobic interactions.  All compounds exhibited the interaction with the peripheral anionic site of TcAChE same manner of standard anti-alzheimer drugs. ADME prediction revealed that all compounds met the requirement of drug likeness of Lipinski’s rule of five and had high CNS absorption, excepted 4 should be structure modification to improve CNS penetration. Besides 4, 6 and 7 displayed the highest acetylcholinesterase inhibitor activity among the other compounds. Interestingly, 6 had a high yield (58.01 mg/g extract) from C. harmandiana. It should be a candidate as an anti-acetylcholinesterase inhibitor agent.

DOI
http://doi.org/10.25135/rnp.288.2106-2112
Keywords
Clausena harmandiana molecular docking coumarins carbazole alkaloids Alzheimer’s disease ADME
Available online: October 05, 2021
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Short Report

18) Fissistigmol A: A New Polyacetylene alcohol from Fissistigma Minuticalyx

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Ping Yang , Ji Song , Mi Zhang , Shiyun Jiao and Weifeng Dai

Abstract:  A new polyacetylene alcohol, Fissistigmol A (1), along with four known polyacetylene alcohol compounds (2-5) were isolated from the aerial part of Fissistigma minuticalyx (McGr. et W. W. Sm.). Their structures were elucidated based on the spectroscopic evidence, mainly including NMR and induced ECD, and HRESIMS data. In addition, bioactivity assay showed that 1-5 showed notable nitric oxide (NO) inhibitory effects (IC50 < 10 μM) on the model of the lipopolysaccharide (LPS)-activated RAW 264.7 macrophages.

DOI
http://doi.org/10.25135/rnp.280.2108.2156
Keywords
Polyacetylene alcohol Annonaceae Fissistigma minuticalyx nitric oxide (NO) inhibitory activity
Available online: October 05, 2021
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Short Report

19) Essential Oil from Hedyotis chrysotricha: Chemical Composition, Cytotoxic, Antibacterial Properties and Synergistic Effects with Streptomycin

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Xinyu Li , Weijia Zhang , Yu Qin and Xiang Xing

 Hedyotis chrysotricha (Palib.) Merr. is a traditional Chinese herb that has been used to treat multiple ailments. In this study, we extracted and characterized the essential oil of H. chrysotricha for the first time and assessed its in vitro cytotoxic, antibacterial activities and the synergistic interaction with Streptomycin. Chemical constituents were determined using GC-FID/MS, which showed 37 components constituted 94.7% of the total oil; borneol (32.7%), linalool (7.5%), isobornyl formate (5.4%) and α-terpineol (4.8%) were the dominant components. The essential oil of H. chrysotricha inhibited strongly the growth of Gram-positive bacteria and possessed a significant cytotoxic activity towards LO2, HepG2 and MCF-7 cells. Besides, the checkerboard assay revealed that the H. chrysotricha essential oil exhibited synergistic potential with Streptomycin. Based on these findings, it can be concluded that the H. chrysotricha essential oil exhibits interesting bioactivities, and could be used as a source of natural antibacterial and anti-tumor compounds.

DOI
http://doi.org/10.25135/rnp.279.2108.2168
Keywords
Hedyotis chrysotricha (Palib.) Merr essential oil antibacterial activity cytotoxic activity synergistic effects
Available online: October 05, 2021
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Short Report

20) A New Diterpenoid with Antitumor Cytotoxicity from Millipede

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Zhimei Shang , Yike Fang , Zongyu Yang , Wanli Luo , Xiaofei Li and Shiji Xiao

 A new diterpenoid, namely millipedine A (10), along with nine known compounds (19), were isolated from the methanol extract of Millipede. Their structures were established on the basis of spectroscopic analysis including one and two-dimensional NMR spectroscopy and comparison with previously reported data. New compound showed moderate cytotoxicity against A549, HCT-116, and SW1990 cell lines in MTT assay.

DOI
http://doi.org/10.25135/rnp.278.21.07.2135
Keywords
Millipede diterpenoid antitumor activities
Available online: September 05, 2021
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Original Article

21) The Limonoids and Other Constituents from the Fruits of Melia azedarach and Their Biological Activity

Rec. Nat. Prod. (2021) in press ; 1 - 9
by Nguyen Ngoc Tuan , Ping-chung Kuo , Vu Dinh Hoang , Vu Thi Hien , Le Dang Quang , Tran Trung Hieu , Yue-chiun Li , Nguyen Tan Thanh , Tian-shung Wu and Tran Dinh Thang

Eleven chemical constituents, including one new limonoid trichilinin G (1), were identified from the fruit extracts of M. azedarach. The structure of 1 was established by various spectroscopic and mass spectrometric analyses. Among the eleven isolated compounds, trichilinin G (1) and meliatoxin B1 (2) were examined for their antifungal activity against Fusarium oxysporum, Magnaporthe grisea, Phytophthora spp. (PS), and P. capsici (PC). Limonoid 2 showed the best antifungal activity against PS (IC50 = 103.8 µg/mL) and PC (IC50 < 62.5 µg/mL) in a dose-dependent manner. While limonoid 1 exhibited a weak to moderate activity against these Phytophthora species, F. oxysporum and M. grisea were less sensitive to the two compounds tested. The inhibitory effects of trichilinin G on superoxide anion generation and elastase release by human neutrophils were also assessed in cellular model and did not show significant activity.

DOI
http://doi.org/10.25135/rnp.277.21.06.2097
Keywords
Triterpenoid limonoid trichilinin antifungal anti-inflammatory
Available online: September 05, 2021
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Original Article

22) A New Organic Acid Derivative from the Fruits of Rosa roxburghii

Rec. Nat. Prod. (2021) in press ; 1 - 4
by Xin Yin , Yongqiang Zhou , Shuang Zhang and Ying Zhou

Phytochemical investigation of the fruits of Rosa roxburghii resulted in the isolation of four organic acid derivatives and three phenylpropanoids, including a new organic acid derivative, Roxbuacidester A (1) and six known compounds (2-7). The structures of all isolates were established by 1D and 2D NMR spectra referring to the literatures, together with HR-MS spectrometric analysis. In addition, compounds 1 and 2 were evaluated for their inhibitory activities on nitric oxide (NO) production stimulated by lipopolysaccharide (LPS) in a RAW 264.7 cell line. Compounds 1 and 2 showed moderate inhibition of NO production with IC50 values of 46.8 ± 2.3 and 62.5 ± 3.7 μM, respectively.

DOI
http://doi.org/10.25135/rnp.276.21.07.2138
Keywords
Rosaceae Rosa roxburghii organic acid derivative
Available online: August 24, 2021
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Original Article

23) Anti-Obesity and Antihyperlipidemic Effects of Musa cavendishii

Rec. Nat. Prod. (2021) in press ; 1 - 13
by Mohammed S. Abdel-raziq , Fatma M. Abdel Bar , Sylvia A. Ashamallah , Nashwa Barakat and Ahmed Gohar

Obesity is a major risk factor in many health problems. This study explored the anti-obesity and antihyperlipidemic effects of Musa cavendishii Lamb. leaves. Doses of 1200 mg/kg of M. cavendishii methanol extract, or 300 mg/kg of fractions, were given to C57BL/6J mice fed with a high-fat diet (HFD) for 7 weeks. The reduction in fat volume was determined using CT scan and histopathological examination of mice livers. The results showed that the n-hexane and the EtOAc fractions reduced the body fat volume to 2.0% and 2.2% respectively, compared to 20.1% in the HFD group. Also, treated groups showed almost normal liver architecture with no fat vacuoles compared to the HFD group. Moreover, the treated groups showed a reduction in the levels of some obesity-related biochemical parameters, including plasma glucose, cholesterol, and triglycerides levels. Chromatographic fractionation of the bioactive n-hexane extract afforded four known compounds viz., palmitic acid (1), 5-methyl-5-(4,8,12-trimethyl-tridecyl)-dihydro-furan-2-one (2), cycloeucalenol (3), and stigmasterol (4). These compounds were in vitro and in silico studied for their pancreatic lipase (PL) inhibition. Compound 2 showed remarkable PL inhibition (89.8%) compared to orlistat (85.0%) at 200 µM, which was in full agreement with the docking scores (-7.19 and -4.05, respectively).

DOI
http://doi.org/10.25135/rnp.275.2103.2001
Keywords
musa cavendishii anti-obesity antihyperlipidemic banana leaf anti-adipogenesis pancreatic lipase
Available online: August 18, 2021
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Short Report

24) Constituents of the Flower of Maxillaria tenuifolia and Their Anti-Diabetic Activity

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Chia-ying Li

The EtOAc extract of the flower of Maxillaria tenuifolia, which had shown potent α-glucosidase inhibitory, was subjected to activity-guided isolation to yield four compounds, 3,4-dihydroxy benzoic acid methyl ester (1), flavanthridin (2), vanillic acid (3) and mangiferin (4).  Their structures were ascertained by comparison of their physical and spectroscopic properties with those reported in the literature.  Among them, flavanthridin (2), vanillic acid (3) and mangiferin (4) showed significant α-glucosidase inhibitory activity compared to acarbose at the concentration 1.0 mg/mL.  Besides, 3,4-dihydroxy benzoic acid methyl ester (1) and mangiferin (4) also showed more effective in against the peroxidation of linoleic acid in an aqueous system than trolox.  These results indicated that the EtOAc extract of M. tenuifolia and the related constituents might have anti-diabetic effect by suppressing carbohydrate disintegration and could prevent damage to organisms by oxidative stress.

DOI
http://doi.org/10.25135/rnp.274.2106.2093
Keywords
α-glucosidase diabetes maxillaria tenuifolia antioxidative
Available online: August 18, 2021
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Short Report

25) Phenolic Acid Analogues from Balanophora laxiflora Inhibit Proliferation of In Vitro Acute Myeloid Leukemia Cells

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Trinh Thi Thuy , Ba Thi Cham , Nguyen Thi Thuy Linh , Phan Thi Ngoc Bich , Sabrina Adorisio and Domenico Delfino

Four phenolic analogues isolated from Balanophora laxiflora; methylgallate (1, MG), 4-hydroxy-3-methoxycinnamaldehyde (2), 3-methoxycinnamic acid (3), and methyl caffeate (4, MC) were shown to have antiproliferative activity on acute myeloid leukemia (OCI-AML3) cells due to impaired cell cycle progression. Three of these compounds (1, 3, and 4) caused increased apoptosis and decreased proliferationin cells. Interestingly, MC (compound 4) significantly decreased the percentage of cells in S phase and G2/M phase, and significantly increased apoptosis in cells at low concentrations. Treatment with these compounds increased Fas ligand production and caspase-8/3, but not caspase-9-dependent, apoptosis. These results suggest that dosing with these compounds decreases proliferation and increases apoptosis in cell lines derived from hematological cancers.

DOI
http://doi.org/10.25135/rnp.273.2106.2117
Keywords
Balanophora laxiflora hemsl. ex forbes & hemsl phenolic acid analogues antiproliferative activity caspase-8 acute myeloid leukemia cell (OCI-AML) human cancer cell lines
Available online: August 18, 2021
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Short Report

26) Scopariaine A: A New Alkaloid from Scoparia dulcis with Protective effect on Cardiomyocytes Injury in Vitro

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Peng Wang , Chenpeng Liu , Sun Wanying and Lei Yang

A new alkaloid, named scopariaine A (1), was obtained from the whole plant of Scoparia dulcis L. The new structure was established by various spectroscopic tmethods including 1D (1H-, 13C-NMR), 2D-NMR (HMBC, HSQC) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). Scopariaine A (1) was tested for its protective effect on attenuating palmitate-induced viability at 5, 10 and 25 μM. The results showed that the cell viability was increased in palmitic acid combined with scopariaine A (1) treated H9C2 cells.

DOI
http://doi.org/10.25135/rnp.268.2105.2073
Keywords
Scoparia dulcis L. scopariaine A alkaloid H9C2 cells
Available online: July 23, 2021
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Original Article

27) Chemical Composition of Flower Volatiles and Seeds Fatty Acids of Rosa iliensis Chrshan, an Endemic Species from Kazakhstan

Rec. Nat. Prod. (2021) in press ; 1 - 11
by Gulmira Özek , Assel Childibayeva , Abybulla Ametov , Akmaral Nurmahanova and Temel Özek

Abstract

In the present work, the flower volatiles and seed fatty acids compositions of three populations (P-I, P-II, P-III) of Rosa iliensis were investigated for the first time. R. iliensis is a rare, endangered, narrow-endemic species growing in floodplains of the Ili and Sharyn rivers of Almaty region. The flower volatiles have been investigated with the tandem of MSD-SPME and GC-MS/FID techniques. The seed lipids were extracted from the ripe fruits with the microextraction technique. The flower volatiles of R. iliensis three populations were characterized by the abundance of oxygenated monoterpenes with benzaldehyde (13.3-38.7 %) and citronellol (2.6-8.8 %) as the major constituents. There were detected significant differences in floral scents between the populations. The flowers of P-I (from Sharyn River) contain sesquiterpene g-elemene (8.8%), the flowers of P-II (upper reaches of the Ili River) were rich in a-gurjunene (12.8%), while flowers of P-III (lower reaches of the Ili River) contained any sesquiterpenes. Seven fatty acids were determined in the seeds and unsaturated acids were found to be dominant for studied populations. Linoleic (43.0-51.0%), a-linolenic (26.5-28.1%) and oleic (12.0-16.1%) acids were detected as the major constituents. The present study shows that R. iliensis species is rich source of valuable volatiles and fatty acids.

 

DOI
http://doi.org/10.25135/rnp.271.2105.2083
Keywords
Rosa iliensis population volatiles fatty acids MSD-SPME GC-MS/FID
Available online: July 23, 2021
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Original Article

28) Two New 13-oxomilbemycins from a NTG-Induced Mutation Strain of Streptomyces avermitilis AVE-H39

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Ji-Dong Wang , Bing Li , Shao-yong Zhang , Yi Wu , Wen-Sheng Xiang , Li-Qin Zhang and Huan Qi

Two new 13-oxomilbemycins, 13-oxomilbemycin β3 (1) and 25-ethyl-13-oxomilbemycin β3 (2), were isolated from the broth of a NTG-induced mutation strain of Streptomyces avermitilis AVE-H39. The structures of 1 and 2 were determined based on MS and extensive NMR analysis. Compounds 1 and 2 possessed moderate nematocidal activity.

DOI
http://doi.org/10.25135/rnp.269.2105.2075
Keywords
Streptomyces avermitilis AVE-H39 NTG-induced mutation 13-oxomilbemycins nematocidal activity
Available online: July 23, 2021
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Original Article

29) Anti-Inflammatory Components from the Fruits of Amomum aromaticum

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Nguyen Hai Dang , Le Nguyen Thanh , Do Hoang Giang and Nguyen Tien Dat

In the course of searching for bioactive components from a Vietnamese spice, the fruits of Amomum aromaticum, a new bicyclic nonane (1) and seven known compounds including 4 monoterpenes (2, 3, 5, 6), one fatty acid (4), and two steroids (7-8) were isolated. Their structures were determined on the basis of spectroscopic analysis. This is the first report of compounds tsaokoin (2), 1β,2α-dihydroxy-p-menth-5-ene (3), oleic acid (4), β-sitosterol (7), and daucosterol (8) in A. aromaticum. To evaluate the anti-inflammatory activities of the isolates, we measured their inhibitory activity against lipopolysaccharide-induced nitric oxide production in a RAW264.7 murine macrophage model. The new compound rel-(1S,5R,6S)-5-methoxybicyclo[4.3.0]non-2-ene-2-carbaldehyde (1) and tsaokoin (2) showed substantial anti-inflammatory effects, with IC50 values of 17.78 and 6.31 µM, respectively. Thus, A. aromaticum fruits could be a rich source for the discovery of anti-inflammatory agents.

DOI
http://doi.org/10.25135/rnp.270.2105.2068
Keywords
Amomum aromaticum bicyclic nonane tsaokoin anti-inflammation
Available online: July 23, 2021
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Short Report

30) Investigation of Pesticidal Activities of Essential Oils Obtained from Vitex Species

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Nguyen Huy Hung , Do Ngoc Dai , Prabodh Satyal , Le Thi Huong , Bui Thi Chinh , Thieu Anh Tai , Vu Thi Hien and William N. Setzer

Essential oils from renewable plant sources are important considerations for environmentally benign botanical pesticides. In this work, the leaf essential oils of four species of Vitex (Lamiaceae) have been collected from north-central Vietnam, analyzed by gas chromatographic techniques, and screened for mosquito larvicidal activity and molluscicidal activity. Vitex ajugifolia and V. pinnata essential oils were dominated by sesquiterpenoids (97.8% and 95.8%, respectively). In contrast, however, the essential oils of V. trifolia subsp. litoralis showed monoterpenoids to be dominant. The essential oils of V. trifolia subsp. trifolia also showed abundant monoterpenoids (38.4% and 68.0%), but also included (E)-β-caryophyllene (15.8 and 14.5%). Vitex pinnata essential oil showed excellent larvicidal activity against Aedes aegypti and Culex quinquefasciatus. Both V. trifolia litoralis and V. trifolia trifolia demonstrated notable molluscicidal activities against Gyraulus convexiusculus and Pomacea canaliculata. The research results suggest that essential oils of Vitex species might have potential to be used as natural pesticides.

DOI
http://doi.org/10.25135/rnp.266.21.06.2108
Keywords
mosquito larvicidal molluscicidal chemical composition botanical pesticide
Available online: July 23, 2021
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