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1. A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)

Author:
Giuseppina Chianese; Carmina Sirignano; Emanuele Benetti; Vittoria Marzaroli; Juan A. Collado; Lauren de la Vega; Giovanni Appendino; Eduardo Muñoz; Orazio Taglialatela-Scafati
Source:
Journal of natural products 2022 v.85 no.4 pp. 1089-1097
ISSN:
1520-6025
Subject:
Cannabis sativa; cannabidiol; chemoprevention; chemotypes; crystallization; hemp; hydroxylation; phytochemicals
Abstract:
... A phytochemical analysis of mother liquors obtained from crystallization of CBD from hemp (Cannabis sativa), guided by LC-MS/MS and molecular networking profiling and completed by isolation and NMR-based characterization of constituents, resulted in the identification of 13 phytocannabinoids. Among them, anhydrocannabimovone (5), isolated for the first time as a natural product, and three new hydr ...
DOI:
10.1021/acs.jnatprod.1c01198

2. Biotransformation of Betulonic Acid by the Fungus Rhizopus arrhizus CGMCC 3.868 and Antineuroinflammatory Activity of the Biotransformation Products

Author:
Kai-Nan Song; You-Jia Lu; Cheng-Jiao Chu; Yan-Ni Wu; Hui-Lian Huang; Bo-Yi Fan; Guang-Tong Chen
Source:
Journal of natural products 2021 v.84 no.10 pp. 2664-2674
ISSN:
1520-6025
Subject:
Rhizopus arrhizus; acetylation; biotransformation; fungi; glycosylation; hydroxylation; spectral analysis
Abstract:
... Biotransformation of betulonic acid (1) by Rhizopus arrhizus CGMCC 3.868 resulted in the production of 16 new (3, 5, 6, and 9–21) and five known compounds. Structures of the new compounds were established by analysis of spectroscopic data. Hydroxylation, acetylation, oxygenation, glycosylation, and addition reactions involved the C-20–C-29 double bond. Antineuroinflammatory activities of the obtai ...
DOI:
10.1021/acs.jnatprod.1c00480

3. Natural Isoflavones and Semisynthetic Derivatives as Pancreatic Lipase Inhibitors

Author:
Nunzio Cardullo; Vera Muccilli; Luana Pulvirenti; Corrado Tringali
Source:
Journal of natural products 2021 v.84 no.3 pp. 654-665
ISSN:
1520-6025
Subject:
anti-obesity agents; bromination; daidzein; fluorescence; formononetin; genistein; hydroxylation; obesity; polyphenols; triacylglycerol lipase
Abstract:
... Obesity, now widespread all over the world, is frequently associated with some chronic diseases. Thus, there is a growing interest in the prevention and treatment of obesity. To date, the only antiobesity drug is orlistat, a natural product-derived pancreatic lipase (PL) inhibitor with some undesired side effects. In the last decades, many natural compounds or derivatives have been evaluated as po ...
DOI:
10.1021/acs.jnatprod.0c01387

4. Decoding the Papain Inhibitor from Streptomyces mobaraensis as Being Hydroxylated Chymostatin Derivatives: Purification, Structure Analysis, and Putative Biosynthetic Pathway

Author:
Norbert E. Juettner; Jan P. Bogen; Tobias A. Bauer; Stefan Knapp; Felicitas Pfeifer; Stefan H. Huettenhain; Reinhard Meusinger; Andreas Kraemer; Hans-Lothar Fuchsbauer
Source:
Journal of natural products 2020 v.83 no.10 pp. 2983-2995
ISSN:
1520-6025
Subject:
Streptomyces mobaraensis; biochemical pathways; biosynthesis; chymotrypsin; crystal structure; hydrophobicity; hydroxylation; ligases; models; nonribosomal peptides; papain; phenylalanine; serine; tyrosine
Abstract:
... Streptomyces mobaraensis produces the papain inhibitor SPI consisting of a 12 kDa protein and small active compounds (SPIₐc). Purification of the papain inhibitory compounds resulted in four diverse chymostatin derivatives that were characterized by NMR and MS analysis. Chymostatins are hydrophobic tetrapeptide aldehydes from streptomycetes, e.g., S. lavendulae and S. hygroscopicus, that reverse c ...
DOI:
10.1021/acs.jnatprod.0c00201

5. Hydroxylated Ethacrylic and Tiglic Acid Derivatives from the Stems and Branches of Enkianthus chinensis and Their Potential Anti-inflammatory Activities

Author:
Hai-Qiang Wang; Shuang-Gang Ma; Ming-Bao Lin; Qi Hou; Min Ma; Shi-Shan Yu
Source:
Journal of natural products 2020 v.83 no.10 pp. 2867-2876
ISSN:
1520-6025
Subject:
Enkianthus; X-ray diffraction; circular dichroism spectroscopy; hydroxylation; macrophages; mice; models; secondary metabolites
Abstract:
... Two new hydroxylated ethacrylic acid derivatives (compounds 1 and 2) and 11 new hydroxylated tiglic acid derivatives (compounds 3–13), together with one known compound (compound 14), were isolated from the stems and branches of Enkianthus chinensis. Their structures were established by extensive spectroscopic analyses, while their absolute configurations were determined by X-ray crystallographic m ...
DOI:
10.1021/acs.jnatprod.0c00286

6. Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells

Author:
David A. Russell; Hannah R. Bridges; Riccardo Serreli; Sarah L. Kidd; Natalia Mateu; Thomas J. Osberger; Hannah F. Sore; Judy Hirst; David R. Spring
Source:
Journal of natural products 2020 v.83 no.6 pp. 1829-1845
ISSN:
1520-6025
Subject:
Parkinson disease; animal diseases; animals; blood-brain barrier; cell proliferation; hydrophilicity; hydrophobicity; hydroxylation; inhibitory concentration 50; mechanism of action; mitochondria; models; neoplasm cells; oxygen consumption; prostatic neoplasms; rotenone; therapeutics
Abstract:
... Prostate cancer is one of the leading causes of cancer-related death in men. The identification of new therapeutics to selectively target prostate cancer cells is therefore vital. Recently, the rotenoids rotenone (1) and deguelin (2) were reported to selectively kill prostate cancer cells, and the inhibition of mitochondrial complex I was established as essential to their mechanism of action. Howe ...
DOI:
10.1021/acs.jnatprod.9b01224

7. NMR Structure Elucidation of Naphthoquinones from Quambalaria cyanescens

Author:
Eliška Procházková; Oleksandr Kucherak; Eva Stodůlková; Zdeněk Tošner; Ivana Císařová; Miroslav Flieger; Miroslav Kolařík; Ondřej Baszczyňski
Source:
Journal of natural products 2020 v.84 no.1 pp. 46-55
ISSN:
1520-6025
Subject:
Quambalaria; cytotoxicity; density functional theory; hydrogen; hydroxylation; naphthoquinones; nuclear magnetic resonance spectroscopy; solubility; tautomers
Abstract:
... Naphthoquinones isolated from Quambalaria cyanescens (quambalarines) are natural pigments possessing significant cytotoxic and antimicrobial properties. Determining the structure of naphthoquinone compounds is important for the understanding of their biological activities and the informed synthesis of related analogues. Identifying quambalarines is challenging, because they contain a hydroxylated ...
DOI:
10.1021/acs.jnatprod.0c00930

8. Structure Elucidation of the spiro-Polyketide Svalbardine B from the Arctic Fungal Endophyte Poaceicola sp. E1PB with Support from Extensive ESI-MSⁿ Interpretation

Author:
Fatimah Bebe M. Hussain; Amjad Ayad Qatran Al-Khdhairawi; Hong Kok Sing; Anis Low Muhammad Low; El Hassane Anouar; Noel F. Thomas; Siti Aisyah Alias; Nurhuda Manshoor; Jean-Frédéric F. Weber
Source:
Journal of natural products 2020 v.83 no.12 pp. 3493-3501
ISSN:
1520-6025
Subject:
Papaver; carbon; endophytes; fungi; hydroxylation; polyketides; Norway
Abstract:
... Svalbardines A and B (1 and 2) and annularin K (3) were isolated from cultures of Poaceicola sp. E1PB, an endophyte isolated from the petals of Papaver dahlianum from Svalbard, Norway. Svalbardine A (1) is a pyrano[3,2-c]chromen-4-one, a new analogue of citromycetin. Svalbardine B (2) displays an unprecedented carbon skeleton based on a 5′-benzyl-spiro[chroman-3,7′-isochromene]-4,8′-dione core. An ...
DOI:
10.1021/acs.jnatprod.9b01105

9. Asperunguisins A–F, Cytotoxic Asperane Sesterterpenoids from the Endolichenic Fungus Aspergillus unguis

Author:
Yue-Lan Li; Yun Gao; Chun-Yu Liu; Chun-Jing Sun; Zun-Tian Zhao; Hong-Xiang Lou
Source:
Journal of natural products 2019 v.82 no.6 pp. 1527-1534
ISSN:
1520-6025
Subject:
Aspergillus; DNA damage; X-ray diffraction; apoptosis; cell cycle checkpoints; cytotoxicity; fungi; human cell lines; humans; hydroxylation; inhibitory concentration 50; neoplasm cells; nuclear magnetic resonance spectroscopy
Abstract:
... Six new asperane-type sesterterpenoids, asperunguisins A–F (1–6), were isolated from the endolichenic fungus Aspergillus unguis, together with a known analogue, aspergilloxide (7); these are rare asperane-type sesterterpenoids, characterized by a unique hydroxylated 7/6/6/5 tetracyclic system. The structures of asperunguisins A–F (1–6) were elucidated on the basis of spectroscopic methods (NMR and ...
DOI:
10.1021/acs.jnatprod.8b01066

10. Structure Elucidation and Relative Toxicity of (24R)-24-Hydroxyyessotoxin from a Namibian Isolate of Gonyaulax spinifera

Author:
Isabelle Rajotte; Cheryl Rafuse; Elliott J. Wright; John C. Achenbach; Lee D. Ellis; Pearse McCarron
Source:
Journal of natural products 2019 v.82 no.7 pp. 1945-1952
ISSN:
1520-6025
Subject:
Danio rerio; Gonyaulax; biomass; hydroxylation; liquid chromatography; mass spectrometry; nuclear magnetic resonance spectroscopy; solvents; toxicity; yessotoxin
Abstract:
... Liquid chromatography–high-resolution mass spectrometry (LC-HRMS) analysis of a Namibian strain of Gonyaulax spinifera showed the presence of a number of yessotoxins (YTXs). Principal among these were YTX (1), homoYTX (2), and a tentative hydroxylated analogue that did not correspond to any previously confirmed YTX structures. Culturing the G. spinifera strain afforded sufficient biomass for purif ...
DOI:
10.1021/acs.jnatprod.9b00318

11. Concise Total Synthesis of (±)-Deguelin and (±)-Tephrosin Using a Vinyl Iodide as a Key Building Block

Author:
Shengtao Xu; Guangyu Wang; Feijie Xu; Wenlong Li; Aijun Lin; Hequan Yao; Jinyi Xu
Source:
Journal of natural products 2018 v.81 no.4 pp. 1055-1059
ISSN:
1520-6025
Subject:
antineoplastic agents; hydroxylation; organoiodine compounds
Abstract:
... A concise and protecting-group-free total synthesis of the antiproliferative natural product (±)-deguelin (2) was accomplished in four steps and 62% overall yield from commercially available precursors. The key transformation employed a vinyl iodide as the pivotal building block to construct the 4-acylchromene substructure present in deguelin. Subsequent Cu₂O-mediated α-hydroxylation of deguelin ( ...
DOI:
10.1021/acs.jnatprod.7b00794

12. Cytochalasans Produced by the Coculture of Aspergillus flavipes and Chaetomium globosum

Author:
Wenjing Wang; Jiaojiao Gong; Xiaorui Liu; Chong Dai; Yanyan Wang; Xiao-Nian Li; Jianping Wang; Zengwei Luo; Yuan Zhou; Yongbo Xue; Hucheng Zhu; Chunmei Chen; Yonghui Zhang
Source:
Journal of natural products 2018 v.81 no.7 pp. 1578-1587
ISSN:
1520-6025
Subject:
Aspergillus flavipes; Chaetomium globosum; X-ray diffraction; biosynthesis; coculture; cytotoxicity; human cell lines; hydroxylation; immunomodulators; neoplasm cells; nuclear magnetic resonance spectroscopy; rice
Abstract:
... The cocultivation of Aspergillus flavipes and Chaetomium globosum, rich sources of cytochalasans, on solid rice medium, resulted in the production of 13 new, highly oxygenated cytochalasans, aspochalasinols A–D (1–4) and oxichaetoglobosins A–I (5–13), as well as seven known compounds (14–20). Of these compounds, 13 is a novel cytochalasan with an unexpected 2-norindole group. The isolated compound ...
DOI:
10.1021/acs.jnatprod.8b00110

13. Stereocontrolled Semisyntheses of Elliptone and 12aβ-Hydroxyelliptone

Author:
Russell David A.; Fong Winston J. S.; Twigg David G.; Sore Hannah F.; Spring David R.
Source:
Journal of natural products 2017 v.80 no.10 pp. 2751-2755
ISSN:
1520-6025
Subject:
Derris elliptica; Derris trifoliata; chemoselectivity; diastereoselectivity; hydroxylation; oxidation; rotenone
Abstract:
... Operationally simple, stereocontrolled semisyntheses of the anticancer rotenoids elliptone and 12aβ-hydroxyelliptone, isolated from Derris elliptica and Derris trifoliata, respectively, are described. Inspired by the work of Singhal, elliptone was prepared from rotenone via a dihydroxylation-oxidative cleavage, chemoselective Baeyer–Villiger oxidation, and acid-catalyzed elimination sequence. Elab ...
DOI:
10.1021/acs.jnatprod.7b00527

14. Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi

Author:
Basso Ana V.; Nicotra Viviana E.; Parra Andrés; Martínez Antonio; Fernández-Vivas Antonia
Source:
Journal of natural products 2016 v.79 no.6 pp. 1658-1667
ISSN:
1520-6025
Subject:
Cunninghamella elegans; Curvularia lunata; Rhizomucor miehei; biotransformation; fungi; hydroxylation; stereochemistry
Abstract:
... Incubation of salpichrolide A (1) with Rhizomucor miehei produced hydroxylation in rings B and C (C-7 and C-12) and led to C-5–C-6 epoxide opening, while incubation of salpichrolides C (2) and G (3) with R. miehei led to epoxide opening at the C-24–C-25 and C-5–C-6 positions, respectively. Biotransformation of salpichrolide A (1) with Cunninghamella elegans produced stereoselective hydroxylated, o ...
DOI:
10.1021/acs.jnatprod.6b00310

15. Depsidones from Lichens as Natural Product Inhibitors of M-Phase Phosphoprotein 1, a Human Kinesin Required for Cytokinesis

Author:
Talapatra Sandeep K.; Rath Oliver; Clayton Eddie; Tomasi Sophie; Kozielski Frank
Source:
Journal of natural products 2016 v.79 no.6 pp. 1576-1585
ISSN:
1520-6025
Subject:
adenosine triphosphate; cytokinesis; humans; hydrophobicity; hydroxylation; kinesin; lichens; median effective concentration; metabolites; microtubules; neoplasm cells; phosphoproteins; screening; urinary bladder neoplasms
Abstract:
... M-Phase Phosphoprotein 1 (MPP1), a microtubule plus end directed kinesin, is required for the completion of cytokinesis. Previous studies have shown that MPP1 is upregulated in various types of bladder cancer. This article describes inhibitor screening leading to the identification of a new class of natural product inhibitors of MPP1. Two compounds with structural similarity, norlobaridone (1) and ...
DOI:
10.1021/acs.jnatprod.5b00962

16. Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum

Author:
Bahadoor Adilah; Schneiderman Danielle; Gemmill Larissa; Bosnich Whynn; Blackwell Barbara; Melanson Jeremy E.; McRae Garnet; Harris Linda J.
Source:
Journal of natural products 2016 v.79 no.1 pp. 81-88
ISSN:
1520-6025
Subject:
Fusarium graminearum; X-ray diffraction; biosynthesis; cytochrome P-450; hydroxylation; light scattering; mutants; nuclear magnetic resonance spectroscopy; plant pathogens; secondary metabolites; stereochemistry; structural genes
Abstract:
... A second structural gene required for culmorin biosynthesis in the plant pathogen Fusarium graminearum is described. Clm2 encodes a regio- and stereoselective cytochrome P450 monooxygenase for C-11 of longiborneol (1). Clm2 gene disruptants were grown in liquid culture and assessed for culmorin production via HPLC-evaporative light scattering detection. The analysis indicated a complete loss of cu ...
DOI:
10.1021/acs.jnatprod.5b00676

17. Monoterpene Indole Alkaloids from the Fruit of Tabernaemontana litoralis and Differential Alkaloid Composition in Various Fruit Components

Author:
Qu Yang; Simonescu Razvan; De Luca Vincenzo
Source:
Journal of natural products 2016 v.79 no.12 pp. 3143-3147
ISSN:
1520-6025
Subject:
Aspidosperma; Tabernaemontana; fruits; hydroxylation; indole alkaloids; monoterpenoids; nuclear magnetic resonance spectroscopy
Abstract:
... Two new monoterpene indole alkaloids, isoakuammiline (1) and 18-hydroxypseudovincadifformine (2), and five known alkaloids, coronaridine (3), heyneanine (4), 3,19-oxidocoronaridine (5), tabersonine, and strictosidine, were identified from the fruit of Tabernaemontana litoralis. The structures of the alkaloids were determined using NMR and MS data analyses. While 18-hydroxypseudovincadifformine (2) ...
DOI:
10.1021/acs.jnatprod.6b00405

18. Synthesis of Coumestrol and Aureol

Author:
Sheng Jianfei; Xu Tianlong; Zhang Ensheng; Zhang Xuejing; Wei Wentao; Zou Yong
Source:
Journal of natural products 2016 v.79 no.10 pp. 2749-2753
ISSN:
1520-6025
Subject:
coumestrol; hydroxylation; spectral analysis
Abstract:
... A total synthesis of coumestrol (1) and aureol (2) is described. The Perkin condensation of 2-bromo-4-hydroxylphenylacetic acid (6) and o-hydroxybenzaldehydes (7) gave the corresponding 2′-bromo-3-arylcoumarins (9). A copper-catalyzed consecutive hydroxylation and aerobic oxidative coupling of 9 under microwave conditions facilitated the total synthesis of 1 and 2, respectively, with spectroscopic ...
DOI:
10.1021/acs.jnatprod.6b00510

19. Withanolide Structural Revisions by 13C NMR Spectroscopic Analysis Inclusive of the γ-Gauche Effect

Author:
Zhang Huaping; Timmermann Barbara N.
Source:
Journal of natural products 2016 v.79 no.4 pp. 732-742
ISSN:
1520-6025
Subject:
hydroxylation; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... A classic withanolide is defined as a highly oxygenated C₂₈ ergostane-type steroid that is characterized by a C₂₂-hydroxy-C₂₆-oic acid δ-lactone in the nine-carbon side chain. Analysis of the reported ¹³C NMR data of classic withanolides with hydroxy groups (C-14, C-17, and C-20) revealed that (1) a hydroxy (C-14 or C-17) substituent significantly alters the chemical shifts (C-7, C-9, C-12, and C- ...
DOI:
10.1021/acs.jnatprod.5b00648

20. Brominated Variant of the Lantibiotic NAI-107 with Enhanced Antibacterial Potency

Author:
Cruz João C. S.; Iorio Marianna; Monciardini Paolo; Simone Matteo; Brunati Cristina; Gaspari Eleonora; Maffioli Sonia I.; Wellington Elizabeth; Sosio Margherita; Donadio Stefano
Source:
Journal of natural products 2015 v.78 no.11 pp. 2642-2647
ISSN:
1520-6025
Subject:
Microbispora; antibacterial properties; bacteriocins; decarboxylation; hydrophobicity; hydroxylation; multiple drug resistance; pathogens; post-translational modification; potassium bromide; tryptophan
Abstract:
... We identified an Actinoallomurus strain producing NAI-107, a chlorinated lantibiotic effective against multidrug-resistant Gram-positive pathogens and previously reported from the distantly related genus Microbispora. Inclusion of KBr in the production medium of either the Actinoallomurus or the Microbispora producer readily afforded brominated variants of NAI-107, which were designated as NAI-108 ...
DOI:
10.1021/acs.jnatprod.5b00576

21. Triterpenoids with Promoting Effects on the Differentiation of PC12 Cells from the Steamed Roots of Panax notoginseng

Author:
Gu Cheng-Zhen; Lv Jun-Jiang; Zhang Xiao-Xia; Qiao Yi-Jun; Yan Hui; Li Yan; Wang Dong; Zhu Hong-Tao; Luo Huai-Rong; Yang Chong-Ren; Xu Min; Zhang Ying-Jun
Source:
Journal of natural products 2015 v.78 no.8 pp. 1829-1840
ISSN:
1520-6025
Subject:
Panax notoginseng; acid hydrolysis; bioactive properties; chemical composition; chemical structure; circular dichroism spectroscopy; dehydrogenation; hydroxylation; medicinal plants; roots; spectral analysis; sugars; triterpenoid saponins
Abstract:
... The roots of Panax notoginseng, an important Chinese medicinal plant, have been used traditionally in both the raw and processed forms, due to the different chemical constituents and bioactivities found. Thirty-eight dammarane-type triterpenoid saponins were isolated from the steam-processed roots of P. notoginseng, including 18 new substances, namely, notoginsenosides SP1–SP18 (1–18). The structu ...
DOI:
10.1021/acs.jnatprod.5b00027

22. “Mirror-Image” Manipulation of Curdione Stereoisomer Scaffolds by Chemical and Biological Approaches: Development of a Sesquiterpenoid Library

Author:
Qin Bin; Li Yuxin; Meng Lingxin; Ouyang Jingping; Jin Danni; Wu Lei; Zhang Xin; Jia Xian; You Song
Source:
Journal of natural products 2015 v.78 no.2 pp. 272-278
ISSN:
1520-6025
Subject:
Aspergillus niger; Curcuma kwangsiensis; bioactive compounds; drugs; enantiomers; essential oils; hydroxylation; neoplasms; sesquiterpenoids; China
Abstract:
... The sesquiterpenoid curdione is one of the main bioactive components in the essential oil of Rhizoma Curcumae (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis), which has been clinically used for the treatment of cancer in mainland China. Recently it was reported that natural curdione could be hydroxylated by Aspergillus niger and transferred to its corresponding curcumalactones un ...
DOI:
10.1021/np500864e

23. Biologically Active Dichapetalins from Dichapetalum gelonioides

Author:
Jing Shu-Xi; Luo Shi-Hong; Li Chun-Huan; Hua Juan; Wang Yan-Li; Niu Xue-Mei; Li Xiao-Nian; Liu Yan; Huang Chun-Shuai; Wang Ying; Li Sheng-Hong
Source:
Journal of natural products 2014 v.77 no.4 pp. 882-893
ISSN:
1520-6025
Subject:
Dichapetalum; X-ray diffraction; antifeedants; antifungal properties; chemical structure; circular dichroism spectroscopy; cytotoxicity; esterification; hydroxylation; nitric oxide; nuclear magnetic resonance spectroscopy; pathogens; triterpenoids
Abstract:
... A phytochemical investigation of the toxic tropical plant Dichapetalum gelonioides led to the isolation and identification of 14 new dichapetalins (1–14) and the known dichapetalins A (15) and K (16). The structures of the new compounds were determined by analyses of their NMR, MS, electronic circular dichroism, and X-ray diffraction data. The esterification at C-25 by 4-hydroxyphenylpropanoic aci ...
DOI:
10.1021/np400971r

24. X-ray Crystal Structure of a Xanthine Oxidase Complex with the Flavonoid Inhibitor Quercetin

Author:
Cao Hongnan; Pauff James M.; Hille Russ
Source:
Journal of natural products 2014 v.77 no.7 pp. 1693-1699
ISSN:
1520-6025
Subject:
X-radiation; active sites; antioxidants; crystal structure; crystals; gout; humans; hydrogen bonding; hydroxylation; hyperuricemia; hypoxanthine; inflammation; molybdenum; quercetin; solvents; structure-activity relationships; uric acid; xanthine; xanthine oxidase
Abstract:
... Xanthine oxidase catalyzes the sequential hydroxylation of hypoxanthine to uric acid via xanthine as intermediate. Deposition of crystals of the catalytic product uric acid or its monosodium salt in human joints with accompanying joint inflammation is the major cause of gout. Natural flavonoids are attractive leads for rational design of preventive and therapeutic xanthine oxidase inhibitors due t ...
DOI:
10.1021/np500320g

25. Identification of the Post-Polyketide Synthase Modification Enzymes for Fostriecin Biosynthesis in Streptomyces pulveraceus

Author:
Liu Xue-jiao; Kong Ri-xiang; Niu Ming-shan; Qiu Rong-guo; Tang Li
Source:
Journal of natural products 2013 v.76 no.4 pp. 524-529
ISSN:
1520-6025
Subject:
Streptomyces pulveraceus; antineoplastic activity; biochemical pathways; biosynthesis; cytochrome P-450; enzymes; hydroxylation; molecular cloning; multigene family; mutants; polyketides; sequence analysis
Abstract:
... Fostriecin (FST, 1) is a natural product with promising antitumor activity produced by Streptomyces pulveraceus. Its antitumor activity is associated with the selective inhibition of protein phosphatase activities. The biosynthetic gene cluster for FST has recently been cloned and sequenced. To better understand the post-polyketide synthase (PKS) modification steps in the biosynthetic pathway of F ...
DOI:
10.1021/np300667r

26. Comparative Analysis of β-Carotene Hydroxylase Genes for Astaxanthin Biosynthesis

Author:
Scaife Mark A.; Ma Cynthia A.; Ninlayarn Thanyanun; Wright Phillip C.; Armenta Roberto E.
Source:
Journal of natural products 2012 v.75 no.6 pp. 1117-1124
ISSN:
1520-6025
Subject:
Archaea; Cyanobacteria; Escherichia coli; antioxidant activity; astaxanthin; bacteria; beta-carotene; biochemical pathways; biosynthesis; catalytic activity; feeds; genes; humans; hydroxylation; stereoisomers; synthesis; zeaxanthin
Abstract:
... Astaxanthin (3,3′-dihydroxy-4,4′-diketo-β-carotene) (1) is a carotenoid of significant commercial value due to its superior antioxidant potential, application as a component of animal feeds, and ongoing research that links its application to the treatment and prevention of human pathologies. The high commercial cost of 1 is also based upon its complex synthesis. Chemical synthesis has been demonst ...
DOI:
10.1021/np300136t

27. 26-Hydroxylated Ecdysteroids from Silene viridiflora

Author:
Tóth, Noémi; Simon, András; Tóth, Gábor; Kele, Zoltán; Hunyadi, Attila; Báthori, Mária
Source:
Journal of natural products 2008 v.71 no.8 pp. 1461-1463
ISSN:
0163-3864
Subject:
Silene; ecdysteroids; hydroxylation; chemical structure; spectral analysis; stereochemistry; Hungary
DOI:
10.1021/np800139q
PubMed:
18661952

28. Microbial Transformation of (-)-Guaiol and Antibacterial Activity of Its Transformed Products

Author:
Choudhary, M.I.; Batool, I.; Atif, M.; Hussain, S.; Atta-ur-Rahman
Source:
Journal of natural products 2007 v.70 no.5 pp. 849-852
ISSN:
0163-3864
Subject:
Zygophyllaceae; sesquiterpenoids; hydroxylation; oxidation; chemical structure; chemical analysis; spectral analysis; Rhizopus stolonifer; Cunninghamella elegans; Macrophomina phaseolina; biotransformation
DOI:
10.1021/np068052a
PubMed:
17385913

29. Spirocaracolitone Triterpenoids from the Bark of Ruptiliocarpon caracolito

Author:
Asim, M.; Hussien, H.; Arnason, J.T.; Poveda, L.; Durst, T.
Source:
Journal of natural products 2007 v.70 no.8 pp. 1228-1232
ISSN:
0163-3864
Subject:
X-ray diffraction; Celastrales; triterpenoids; chemical structure; spectral analysis; stereochemistry; hydroxylation; esterification; insecticidal properties; Crambidae; Costa Rica
DOI:
10.1021/np060490u
PubMed:
17665950

30. Hydroxylated Gedunin Derivatives from Cedrela sinensis

Author:
Mitsui, K.; Saito, H.; Yamamura, R.; Fukaya, H.; Hitotsuyanagi, Y.; Takeya, K.
Source:
Journal of natural products 2006 v.69 no.9 pp. 1310-1314
ISSN:
0163-3864
Subject:
cytotoxicity; medicinal plants; chemical structure; mice; cultured cells; Cedrela; spectral analysis; hydroxylation; stereochemistry; limonoids; Oriental traditional medicine; anticarcinogenic activity; China
DOI:
10.1021/np068021f
PubMed:
16989525

31. Microbial O-Demethylation, Hydroxylation, Sulfation, and Ribosylation of a Xanthone Derivative from Halenia elliptica

Author:
Yuan, W.; Zhang, L.P.; Cheng, K.D.; Zhu, P.; Wang, Q.; He, H.X.; Zhu, H.X.
Source:
Journal of natural products 2006 v.69 no.5 pp. 811-814
ISSN:
0163-3864
Subject:
Gentianales; medicinal plants; Oriental traditional medicine; xanthones; biotransformation; hydroxylation; chemical structure; spectral analysis; Trichothecium roseum; plant pathogenic fungi; Paecilomyces; microbial physiology
DOI:
10.1021/np050472x
PubMed:
16724847

32. Polyhydroxylated Phragmalins from the Fruit of a Chinese Mangrove, Xylocarpus granatum

Author:
Zhou, Y.; Cheng, F.; Wu, J.; Zou, K.
Source:
Journal of natural products 2006 v.69 no.7 pp. 1083-1085
ISSN:
0163-3864
Subject:
chemical structure; spectral analysis; hydroxylation; limonin; Xylocarpus; stereochemistry; China
DOI:
10.1021/np050545c
PubMed:
16872150

33. N-(jasmonoyl)tyrosine-derived compounds from flowers of broad beans (Vicia faba)

Author:
Kramell, R.; Schmidt, J.; Herrmann, G.; Schliemann, W.
Source:
Journal of natural products 2005 v.68 no.9 pp. 1345-1349
ISSN:
0163-3864
Subject:
Vicia faba; faba beans; flowers; plant extracts; phytochemicals; tyrosine; jasmonic acid; dihydroxyphenylalanine; dopamine; chemical structure; spectral analysis; hydroxylation
DOI:
10.1021/np0501482
PubMed:
16180811

34. Biotransformation of the diterpenes epicandicandiol and candicandiol by Mucor plumbeus

Author:
Fraga, B.M.; Alvarez, L.; Suarez, S.
Source:
Journal of natural products 2003 v.66 no.3 pp. 327-331
ISSN:
0163-3864
Subject:
Mucor; Sideritis; phytochemicals; diterpenoids; metabolites; hydroxylation; acetylation; biotransformation; spectral analysis; chemical structure
DOI:
10.1021/np020420x
PubMed:
12662087

35. Microbial transformation of 18-hydroxy-9,13-epi-ent-pimara-7,15-diene by Gibberella fujikuroi

Author:
Fraga, B.M.; Gonzalez, P.; Hernandez, M.G.; Chamy, M.C.; Garbarino, J.A.
Source:
Journal of natural products 2003 v.66 no.3 pp. 392-397
ISSN:
0163-3864
Subject:
biotransformation; Fusarium fujikuroi; isomers; epoxides; diterpenoids; oxidation; spectral analysis; hydroxylation; stereochemistry; metabolites
DOI:
10.1021/np020457h
PubMed:
12662098

36. Biotransformation of caryophyllene oxide by Botrytis cinerea

Author:
Duran, R.; Corrales, E.; Hernandez-Galan, R.; Collado, I.G.
Source:
Journal of natural products 1999 v.62 no.1 pp. 41-44
ISSN:
0163-3864
Subject:
sesquiterpenoids; Botrytis cinerea; plant pathogenic fungi; biodegradation; spectral analysis; pathogenesis; stereochemistry; chemical structure; metabolites; hydroxylation
DOI:
10.1021/np980104b