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1. Acylphloroglucinol Derivatives from Hypericum andinum: Antidepressant-like Activity of Andinin A

Author:
Ccana-Ccapatinta, Gari V.; Stolz, Eveline D.; da Costa, Paola F.; Rates, Stela M. K.; von Poser, Gilsane L.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2321-2325
ISSN:
1520-6025
Subject:
Hypericum; mice; nuclear magnetic resonance spectroscopy; plant anatomy
Abstract:
... A new dimeric acylphloroglucinol derivative, andinin A (1), was isolated from the underground plant parts of Hypericum andinum, along with three known dimeric acylphloroglucinols, uliginosin A (2), uliginosin B (3), and isouliginosin B (4). The structure of 1 was elucidated using 1D and 2D NMR and MS experiments and by comparison with previously reported data for Hypericum dimeric acylphloroglucin ...
DOI:
10.1021/np500426m

2. Anti-inflammatory Ursane- and Oleanane-Type Triterpenoids from Vitex negundo var. cannabifolia

Author:
Li, Man-Man; Su, Xiao-Qin; Sun, Jing; Gu, Yu-Fan; Huang, Zheng; Zeng, Ke-Wu; Zhang, Qian; Zhao, Yun-Fang; Ferreira, Daneel; Zjawiony, Jordan K.; Li, Jun; Tu, Peng-Fei
Source:
Journal of natural products 2014 v.77 no.10 pp. 2248-2254
ISSN:
1520-6025
Subject:
Vitex negundo; X-ray diffraction; anti-inflammatory activity; inhibitory concentration 50; leaves; macrophages; nitric oxide; triterpenoids
Abstract:
... Six new polyoxygenated triterpenoids, cannabifolins A–F (1–6), and eight known triterpenoids, 7–14, were isolated from the leaves of Vitex negundo var. cannabifolia. The absolute configuration of cannabifolin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 represent a class of rare natural pentacyclic triterpenoids bearing cis-fused C/D rings and are the f ...
DOI:
10.1021/np500509q

3. Antitrypanosomal Quinoline Alkaloids from the Roots of Waltheria indica

Author:
Cretton, Sylvian; Breant, Lise; Pourrez, Lucie; Ambuehl, Chiara; Marcourt, Laurence; Ebrahimi, Samad Nejad; Hamburger, Matthias; Perozzo, Remo; Karimou, Soumana; Kaiser, Marcel; Cuendet, Muriel; Christen, Philippe
Source:
Journal of natural products 2014 v.77 no.10 pp. 2304-2311
ISSN:
1520-6025
Subject:
Trypanosoma cruzi; antiparasitic properties; chemical structure; cytotoxicity; growth retardation; inhibitory concentration 50; methylene chloride; mice; nuclear magnetic resonance spectroscopy; quinoline alkaloids; roots; spectral analysis
Abstract:
... Chemical investigation of the dichloromethane root extract of Waltheria indica led to the isolation and characterization of 10 quinoline alkaloids, namely, 8-deoxoantidesmone (1), waltheriones E–L (2–9), and antidesmone (10). Among these, compounds 2–9 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including ¹ ...
DOI:
10.1021/np5006554

4. Autumnalamide, a Prenylated Cyclic Peptide from the Cyanobacterium Phormidium autumnale, Acts on SH-SY5Y Cells at the Mitochondrial Level

Author:
Audoin, Coralie; Sánchez, Jon Andoni; Genta-Jouve, Grégory; Alfonso, Amparo; Rios, Laurent; Vale, Carmen; Thomas, Olivier P.; Botana, Luis M.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2196-2205
ISSN:
1520-6025
Subject:
Cyanobacterium (genus); Phormidium autumnale; arginine; calcium; enantiomers; gas chromatography-mass spectrometry; guanidines; mitochondria; models; nuclear magnetic resonance spectroscopy; permeability; sodium; spectral analysis
Abstract:
... Filamentous cyanobacteria of the genus Phormidium have been rarely studied for their chemical diversity. For the first time, the cultivable Phormidium autumnale was shown to produce a prenylated cyclic peptide named autumnalamide (1). The structure of this peptide was fully determined after a deep exploration of the spectroscopic data, including NMR and HRMS. Interestingly, a prenyl moiety was loc ...
DOI:
10.1021/np500374a

5. Bioactive Clerodane Diterpenoids from the Twigs of Casearia balansae

Author:
Xu, Jing; Zhang, Qiang; Wang, Meicheng; Ren, Quanhui; Sun, Yihang; Jin, Da-Qing; Xie, Chunfeng; Chen, Hongqiang; Ohizumi, Yasushi; Guo, Yuanqiang
Source:
Journal of natural products 2014 v.77 no.10 pp. 2182-2189
ISSN:
1520-6025
Subject:
Casearia; branches; diterpenoids; neurites; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... Eight new clerodane diterpenes, balanspenes A–H (1–8), along with two known analogues (9 and 10), were isolated from the twigs of Casearia balansae. The structures of 1–8 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of compounds 1, 4, and 7 were confirmed by comparing their experimental CD spectra with those calculated by the ...
DOI:
10.1021/np5003516

6. Bioactive Spirobisnaphthalenes from the Endophytic Fungus Berkleasmium sp.

Author:
Shan, Tijiang; Tian, Jin; Wang, Xiaohan; Mou, Yan; Mao, Ziling; Lai, Daowan; Dai, Jungui; Peng, Youliang; Zhou, Ligang; Wang, Mingan
Source:
Journal of natural products 2014 v.77 no.10 pp. 2151-2160
ISSN:
1520-6025
Subject:
Agrobacterium radiobacter; Bacillus subtilis; Dioscorea zingiberensis; Magnaporthe oryzae; Pseudomonas; Ralstonia solanacearum; Staphylococcus; Xanthomonas vesicatoria; antibacterial properties; antifungal properties; cytotoxicity; endophytes; fungi; humans; inhibitory concentration 50; medicinal plants; neoplasms; nuclear magnetic resonance spectroscopy; spore germination
Abstract:
... Nine new spirobisnaphthalenes, palmarumycins B₁–B₉ (1–9), along with 13 known compounds (10–22), were isolated from cultures of the fungus Berkleasmium sp., an endophyte isolated from the medicinal plant Dioscorea zingiberensis C. H. Wright. The structures of the new compounds were elucidated by analysis of the 1D and 2D NMR and HRESIMS spectra and by comparison with known compounds. Compounds 7–9 ...
DOI:
10.1021/np400988a

7. Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample

Author:
Cai, Shengxin; King, Jarrod B.; Du, Lin; Powell, Douglas R.; Cichewicz, Robert H.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2280-2287
ISSN:
1520-6025
Subject:
Alternaria; X-radiation; bioassays; cytotoxicity; mass spectrometry; metabolites; nuclear magnetic resonance spectroscopy
Abstract:
... Polluxochrin (1) and dioschrin (2), two new dimers of sulochrin linked by thioether bonds, were purified from an Alternaria sp. isolate obtained from a Hawaiian soil sample. The structures of the two metabolites were established by NMR, mass spectrometry data, and X-ray analysis. Metabolite 1 was determined to be susceptible to intramolecular cyclization under aqueous conditions, resulting in the ...
DOI:
10.1021/np5005449
PubMed:
25265160
PubMed Central:
PMC4208674

8. Chemopreventive Effects of (−)-Hinokinin against 1,2-Dimethylhydrazine-Induced Genotoxicity and Preneoplastic Lesions in Rat Colon

Author:
Barbosa, Lilian C.; Furtado, Ricardo A.; Bertanha, Humberto C. C.; Tomazella, Iara M.; Costa, Eveline S.; Bastos, Jairo K.; Silva, Márcio L. Andrade e; Tavares, Denise C.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2312-2315
ISSN:
1520-6025
Subject:
1,2-dimethylhydrazine; anticarcinogenic activity; blood; chemoprevention; colon; comet assay; genotoxicity; lignans; mutagens; rats
Abstract:
... (−)-Hinokinin (1) is a dibenzylbutyrolactone lignan obtained by the partial synthesis of (−)-cubebin. This study reports the antigenotoxic and anticarcinogenic potential of 1 by the comet and aberrant crypt focus assays in the peripheral blood and colon of 4–5-week-old Wistar rats, respectively. The rats were exposed to 1,2-dimethylhydrazine (40 mg/kg) and were treated by gavage with doses of 10, ...
DOI:
10.1021/np500093u

9. Cytotoxic Resin Glycosides from Ipomoea aquatica and Their Effects on Intracellular Ca2+ Concentrations

Author:
Fan, Bo-Yi; Gu, Yu-Cheng; He, Ye; Li, Zhong-Rui; Luo, Jian-Guang; Kong, Ling-Yi
Source:
Journal of natural products 2014 v.77 no.10 pp. 2264-2272
ISSN:
1520-6025
Subject:
Ipomoea aquatica; acids; apoptosis; calcium; cell cycle; cytotoxicity; glycosides; human cell lines; humans; inhibitory concentration 50; neoplasms; rhamnose; spectroscopy
Abstract:
... Eleven new resin glycosides, aquaterins I–XI (1–11), were isolated from the whole plants of Ipomoea aquatica. The structures of 1–11 were elucidated by a combination of spectroscopic and chemical methods. They were found to be partially acylated tetra- or pentasaccharides derived from simonic acid B and operculinic acids A and C. The site of the aglycone macrolactonization was placed at C-2 or C-3 ...
DOI:
10.1021/np5005246

10. Eurifoloids A–R, Structurally Diverse Diterpenoids from Euphorbia neriifolia

Author:
Zhao, Jin-Xin; Liu, Cui-Ping; Qi, Wei-Yan; Han, Mei-Ling; Han, Ying-Shan; Wainberg, Mark A; Yue, Jian-Min
Source:
Journal of natural products 2014 v.77 no.10 pp. 2224-2233
ISSN:
1520-6025
Subject:
Euphorbia neriifolia; antiretroviral properties; diterpenoids; median effective concentration
Abstract:
... Eighteen new diterpenoids, named eurifoloids A–R (1–18), including ingenane (1 and 2), abietane (3–7), isopimarane (8–12), and ent-atisane (13–18) types, along with four known analogues were isolated from Euphorbia neriifolia. Eurifoloid M (13) represents a rare class of ent-atisane-type norditerpenoid. Eurifoloids E (5) and F (6) exhibited significant anti-HIV activities, with EC₅₀ values of 3.58 ...
DOI:
10.1021/np5004752

11. Identification of Key Structural Characteristics of Schisandra chinensis Lignans Involved in P-Glycoprotein Inhibition

Author:
Slanina, Jiří; Páchniková, Gabriela; Čarnecká, Martina; Porubová Koubíková, Ludmila; Adámková, Lenka; Humpa, Otakar; Šmejkal, Karel; Slaninová, Iva
Source:
Journal of natural products 2014 v.77 no.10 pp. 2255-2263
ISSN:
1520-6025
Subject:
P-glycoproteins; Schisandra chinensis; cytotoxicity; doxorubicin; enantiomers; humans; leukemia; lignans; quantitative structure-activity relationships
Abstract:
... The aim of the present study was to determine the structural requirements for dibenzocyclooctadiene lignans essential for P-glycoprotein inhibition. Altogether 15 structurally related lignans isolated from Schisandra chinensis or prepared by modification of their backbone were investigated, including three pairs of enantiomers. P-Glycoprotein inhibition was quantified using a doxorubicin accumulat ...
DOI:
10.1021/np500521v

12. Indazole-Type Alkaloids from Nigella sativa Seeds Exhibit Antihyperglycemic Effects via AMPK Activation in Vitro

Author:
Yuan, Tao; Nahar, Pragati; Sharma, Meenakshi; Liu, Ke; Slitt, Angela; Aisa, H. A.; Seeram, Navindra P.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2316-2320
ISSN:
1520-6025
Subject:
AMP-activated protein kinase; Nigella sativa; alkaloids; glucose; glycemic effect; hepatocytes; human cell lines; liver; seeds
Abstract:
... Six rare naturally occurring indazole-type alkaloids including two new compounds, 17-O-(β-d-glucopyranosyl)-4-O-methylnigellidine (1) and nigelanoid (2), and four known compounds (3–6) were isolated from a defatted extract of Nigella sativa (black cumin) seeds. 17-O-(β-d-Glucopyranosyl)-4-O-methylnigellidine (1) increased glucose consumption by liver hepatocytes (HepG2 cells) through activation of ...
DOI:
10.1021/np500398m
PubMed:
25299458
PubMed Central:
PMC4208670

13. iNOS Inhibitory Activity of Sesquiterpenoids and a Monoterpenoid from the Rhizomes of Curcuma wenyujin

Author:
Yin, Guo-Ping; Li, Liang-Chun; Zhang, Qing-Zhe; An, Yue-Wei; Zhu, Jing-Jing; Wang, Zhi-Min; Chou, Gui-Xin; Wang, Zheng-tao
Source:
Journal of natural products 2014 v.77 no.10 pp. 2161-2169
ISSN:
1520-6025
Subject:
Curcuma; X-ray diffraction; inducible nitric oxide synthase; inhibitory concentration 50; monoterpenoids; nitric oxide; nuclear magnetic resonance spectroscopy; rhizomes; sesquiterpenoids
Abstract:
... Eleven new sesquiterpenoids, wenyujinins A–K (1–11), and a new monoterpenoid, wenyujinin L (12), were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute configurations of 1, 2, 3, 4, 6, 8, 9, and 10 were determined by comparison of the experimental and calc ...
DOI:
10.1021/np400984c

14. Merremins A–G, Resin Glycosides from Merremia hederacea with Multidrug Resistance Reversal Activity

Author:
Wang, Wen-qiong; Song, Wei-bin; Lan, Xiao-jing; Huang, Min; Xuan, Li-jiang
Source:
Journal of natural products 2014 v.77 no.10 pp. 2234-2240
ISSN:
1520-6025
Subject:
Merremia; aerial parts; cytotoxicity; esters; glycosides; multiple drug resistance; vinblastine
Abstract:
... Five new pentasaccharide resin glycosides, named merremins A–E (1–5), two new pentasaccharide resin glycoside methyl esters, named merremins F and G (6, 7), and four known resin glycosides, murucoidin IV, murucoidin V, stoloniferin IV, and murucoidin XVII, were obtained from the aerial parts of Merremia hederacea. This is the first report of resin glycosides obtained from M. hederacea. In addition ...
DOI:
10.1021/np500483d

15. Nocatriones A and B, Photoprotective Tetracenediones from a Marine-Derived Nocardiopsis sp.

Author:
Kim, Min Cheol; Hwang, Eunson; Kim, Taejung; Ham, Jungyeob; Kim, Sun Yeou; Kwon, Hak Cheol
Source:
Journal of natural products 2014 v.77 no.10 pp. 2326-2330
ISSN:
1520-6025
Subject:
Nocardiopsis; Porifera; collagen; culture media; models; ultraviolet radiation
Abstract:
... Two new tetracenedione derivatives, nocatriones A (1) and B (2), were discovered from the culture broth of a marine actinomycete, Nocardiopsis sp. KMF-002, which was isolated from the tissue of an unidentified dark purple marine sponge. The structures of 1 and 2, which are tetracenediones containing α-pyrone substituents, were determined to be 3,8,10,11-tetrahydroxy-2-(4-hydroxy-2-oxo-2H-pyran-6-y ...
DOI:
10.1021/np5006086

16. Polyketide Glycosides from Bionectria ochroleuca Inhibit Candida albicans Biofilm Formation

Author:
Wang, Bin; You, Jianlan; King, Jarrod B.; Cai, Shengxin; Park, Elizabeth; Powell, Douglas R.; Cichewicz, Robert H.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2273-2279
ISSN:
1520-6025
Subject:
Candida albicans; Clonostachys rosea; antibiotics; antifungal properties; bags; biofilm; breakfast cereals; candidiasis; culture flasks; glycosides; metabolome; mushrooms; pathogens; polyketides; screening; secondary metabolites
Abstract:
... One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens’ susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples ...
DOI:
10.1021/np500531j
PubMed:
25302529
PubMed Central:
PMC4208675

17. Protective Effects of Resveratrol on Hepatotoxicity Induced by Isoniazid and Rifampicin via SIRT1 Modulation

Author:
Nicoletti, Natália F.; Rodrigues-Junior, Valnês; Santos, André A.; Leite, Carlos E.; Dias, Ana C. O.; Batista, Eraldo L.; Basso, Luiz A.; Campos, Maria M.; Santos, Diógenes S.; Souto, André A.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2190-2195
ISSN:
1520-6025
Subject:
alanine transaminase; aspartate transaminase; blood serum; catalase; drugs; gene expression; glutathione; hepatotoxicity; histopathology; interleukin-10; interleukin-12; isoniazid; liver; liver diseases; males; messenger RNA; mice; myeloperoxidase; oxidative stress; protective effect; resveratrol; rifampicin; tumor necrosis factor-alpha
Abstract:
... Acute liver injury was induced in male BALB/c mice by coadministering isoniazid and rifampicin. In this work, the effects of resveratrol (1) were investigated in the hepatotoxicity caused by isoniazid–rifampicin in mice. Compound 1 was administered 30 min prior to isoniazid–rifampicin. Serum biochemical tests, liver histopathological examination, oxidative stress, myeloperoxidase activity, cytokin ...
DOI:
10.1021/np5003143

18. Psychrophilins E–H and Versicotide C, Cyclic Peptides from the Marine-Derived Fungus Aspergillus versicolor ZLN-60

Author:
Peng, Jixing; Gao, Huquan; Zhang, Xiaomin; Wang, Shuai; Wu, Chongming; Gu, Qianqun; Guo, Peng; Zhu, Tianjiao; Li, Dehai
Source:
Journal of natural products 2014 v.77 no.10 pp. 2218-2223
ISSN:
1520-6025
Subject:
Aspergillus versicolor; X-ray diffraction; anthranilic acid; cyclic peptides; cytotoxicity; fungi; nitrogen; nuclear magnetic resonance spectroscopy
Abstract:
... Four new cyclic peptides, psychrophilins E–H (1–4), possessing a rare amide linkage between the carboxylic acid in anthranilic acid (ATA) and the nitrogen from an indole moiety, along with a new ATA-containing hexapeptide, versicotide C (5), were obtained from the culture of the marine-derived fungus Aspergillus versicolor ZLN-60. The structures, including absolute configurations, were elucidated ...
DOI:
10.1021/np500469b

19. Strain Prioritization for Natural Product Discovery by a High-Throughput Real-Time PCR Method

Author:
Hindra,; Huang, Tingting; Yang, Dong; Rudolf, Jeffrey D.; Xie, Pengfei; Xie, Guangbo; Teng, Qihui; Lohman, Jeremy R.; Zhu, Xiangcheng; Huang, Yong; Zhao, Li-Xing; Jiang, Yi; Duan, Yanwen; Shen, Ben
Source:
Journal of natural products 2014 v.77 no.10 pp. 2296-2303
ISSN:
1520-6025
Subject:
diterpenoids; genome mining; prioritization; quantitative polymerase chain reaction; sequence analysis
Abstract:
... Natural products offer unmatched chemical and structural diversity compared to other small-molecule libraries, but traditional natural product discovery programs are not sustainable, demanding too much time, effort, and resources. Here we report a strain prioritization method for natural product discovery. Central to the method is the application of real-time PCR, targeting genes characteristic to ...
DOI:
10.1021/np5006168
PubMed:
25238028
PubMed Central:
PMC4208669

20. Synthesis and Anti-inflammatory and Pro-resolving Activities of 22-OH-PD1, a Monohydroxylated Metabolite of Protectin D1

Author:
Tungen, Jørn E.; Aursnes, Marius; Vik, Anders; Ramon, Sesquile; Colas, Romain A.; Dalli, Jesmond; Serhan, Charles N.; Hansen, Trond V.
Source:
Journal of natural products 2014 v.77 no.10 pp. 2241-2247
ISSN:
1520-6025
Subject:
anti-inflammatory activity; chemotaxis; hydrolysis; macrophages; metabolism; metabolites; phagocytosis; polyunsaturated fatty acids
Abstract:
... Protectin D1 (PD1 (3)), a C22-dihydroxylated polyunsaturated fatty acid biosynthesized from all-Z-docosahexaenoic acid, belongs to the new family of endogenous mediators referred to as specialized pro-resolving lipid mediators. PD1 (3) is a natural product that displays potent anti-inflammatory properties together with pro-resolving actions including inhibition of polymorphonuclear leukocyte (PMN) ...
DOI:
10.1021/np500498j
PubMed:
25247845
PubMed Central:
PMC4208671