Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• three human cell lines. None of the compounds tested showed any activity up to 100 μg mL−1 against the Gram-negative bacterium Escherichia coli (ATCC 25922), the fungus Candida albicans (ATCC 10231) or the plant Eragrostis tef (teff). Proposed biosynthesis and gene cluster The biosynthesis of drimane

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• luteus ATCC9341, Bacillus subtilis ATCC6633, Escherichia coli NIHJ JC-2, Ralstonia solanacearum SUPP1541, Rhizobium radiobacter NBRC14554, and Candida albicans NBRC0197 (MIC > 100 μg/mL) but weakly active against Saccharomyces cerevisiae S100 (MIC 100 μg/mL). Conclusion In summary, chemical investigation

• microtiter plates against six bacteria, Bacillus subtilis ATCC6633, Micrococcus luteus ATCC9341, Staphylococcus aureus FDA209P JC-1, Ralstonia solanacearum SUPP1541, Rhizobium radiobacter NBRC14554, Escherichia coli NIHJ JC-2, and two yeasts Candida albicans NBRC0197 and Saccharomyces cerevisiae S100 as

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

• Yan Xiao,
• Bing Jing,
• Xiaoxia Liu,
• Hongyu Xue and
• Yajun Liu

Beilstein J. Org. Chem. 2019, 15, 279–284, doi:10.3762/bjoc.15.24

• activity against Candida albicans and Candida tropicalis [8] and 2-mercapto-1,3-benzothiol and its derivatives exhibit inhibitory effects against thyroid peroxidase [9]. (Hetero)aryl thiols are often prepared from the corresponding halides through direct nucleophilic substitution [10][11][12] or metal

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• products of Rv1753 and Rv2082 were reported to have 27% and 25% amino acid sequence similarity to the ALS1 gene from Candida albicans, which encodes the candida adhesin [78]. This lectin is cell surface-localized and mediates adherence of the fungus to endothelial and epithelial cells [86][87]. Fucose

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

• Lucky S. Mulwa,
• Rolf Jansen,
• Dimas F. Praditya,
• Kathrin I. Mohr,
• Patrick W. Okanya,
• Joachim Wink,
• Eike Steinmann and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

• -HPLC fractionating and peak-activity correlation we further noted at tR = 18–25 min an inhibition overlap of Micrococcus luteus and Candida albicans, which correlated with some prominent peaks with unique HPLC-DAD-MS characteristics attracting our interest. Consequently, the fermentation process was

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

• Dandan Li,
• Naoya Oku,
• Atsumi Hasada,
• Masafumi Shimizu and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

• NBRC16015, Trichophyton rubrum NBRC5467, Candida albicans NBRC0197 (human opportunistic pathogen), R. oryzae NBRC4705, Glomerella cingulata NBRC5907 (pathogen of anthracnose), Ralstonia solanacearum SUPP1541 (pathogen of bacterial wilt of Solanaceous plants), Rhizobium radiobacter NBRC14554 (pathogen of

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• shown to bind A·T-rich regions preferentially. The compounds containing branched N-alkylpyrrole, hydrophobic N-terminal amide, and especially C-isopropylthiazole (thiazotropsin A as shown in the Figure 4) showed significant antimicrobial activity against MRSA and Candida albicans strains. Thiazotropsin

Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling

• Xinli Pan,
• Nicole Domin,
• Sebastian Schieferdecker,
• Hirokazu Kage,
• Martin Roth and
• Markus Nett

Beilstein J. Org. Chem. 2017, 13, 2458–2465, doi:10.3762/bjoc.13.242

• performed as previously described [27]. The test organisms included Bacillus subtilis ATCC 6633, Staphylococcus aureus SG 511, Mycobacterium vaccae IMET 10670, Escherichia coli SG 458, Pseudomonas aeruginosa K 799/61, Sporobolomyces salmonicolor SBUG 549, Candida albicans ATCC 14053 and Penicillium notatum

Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

• Henryk Myszka,
• Patrycja Sokołowska,
• Agnieszka Cieślińska,
• Andrzej Nowacki,
• Maciej Jaśkiewicz,
• Wojciech Kamysz and
• Beata Liberek

Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227

• as well as the HRMS spectrometry confirmed the structures of 11–13 (see Supporting Information File 1 for experimental and NMR data). Evaluation of antimicrobial activity The antimicrobial in vitro activities of 5–13 were tested against two fungal strains: Candida albicans and Candida tropicalis, and

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• recently, isolation of butyrolactols C and D was presented but the details are not available in public domains [10]. 1 has a broad antimicrobial activity against fungi ranging from Candida albicans to Trichophyton mentagrophytes with comparative activity to nystatin [9]. Despite the uniqueness of the

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• ), Candida albicans (DSM 1665) and Mucor hiemalis (DSM 2656, 33.3 μg mL−1 in each case). Significant cytotoxic activity was revealed for 22 towards SKOV-3 (IC50 = 2.4 μM), KB3-1 (IC50 = 5.3 μM), as well as A431 (IC50 = 8.45 μM), while 23 showed remarkable cytotoxicity against cell lines HUVEC and KB3-1 (IC50

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• (e.g., bafilomycin A1 (21) and B1 (22), Figure 7), but also a novel polyunsaturated and polyoxygenated 26-membered macrolactam named sceliphrolactam (23) (Figure 7) [101]. Sceliphrolactam showed strong antifungal activity against amphotericin B-resistant Candida albicans, but its functional role in

Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

• Qun Göthel,
• Thanchanok Sirirak and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2334–2342, doi:10.3762/bjoc.11.254

• luteus; Gram-negative: Peumonia aruginosa and Klebsiella pneumonia] and antifungal Candida albicans using microdilution technique. The MIC was defined as lowest concentration that shows 50% growth inhibition after 24 hour incubation. Cytotoxicity assay The cytotoxicity was determined using WST-1 cell

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• antifungal activities against the filamentous fungal strain Aspergillus flavus (Link) and the yeast forming fungal strain Candida albicans (ATCC 7102) were moderate compared with amphotericin B in vitro. In the cytotoxicity study, this derivative was the most cytotoxic one against the prostate cancer PC3

• that were as active as ampicillin. However, conjugate VI from the previous investigation was still more active than these conjugates [24]. The antifungal activity of selected newly synthesized chalcone conjugates was evaluated in vitro against A. flavus (Link) and Candida albicans (ATCC 7102) similarly

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

• Louis P. Sandjo,
• Victor Kuete and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

• interesting antimicrobial potency (minimal inhibitory concentration, MIC, below 10 µg/mL) has been assigned to some pyridoacridines such as meridine (56) and ascididemin (42). Compound 56 inhibited the growth of Candida albicans (MIC: 0.2–3.1 µg/mL) and Cryptococcus neoformans (MIC 0.8 µg/mL) as well as that

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• with the longer alkyl chains (13–15, 17) show very weak inhibitory activity against Candida tropicalis. The results presented for Candida albicans resemble those obtained for Candida tropicalis. The growth of this strain of fungi is inhibited at the lowest concentrations by 7·HCl and equally well by 8

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• lead to loss of vision. Candida albicans is one of the most widespread fungal pathogens involved in fungal keratitis [1][2]. The most common antifungal treatments include the use of polyenes and azoles; however, a significant treatment failure rate exists with these pharmacological agents [3

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• Candida albicans (ATCC 10231) or Fusarium oxysporum f. sp. cubense race 4 at concentrations as high as 20 mg/mL. Conclusion In summary, guided by 1H NMR detection, we isolated and characterized a novel norditerpenoid, aspergiloid I (1), from the liquid fermentation broth of the endophytic Aspergillus sp

• graminearum Schw., Fusarium coeruleum Sacc., Botrytis cinerea Pers., and Fusarium oxysporum f. sp. cubense race 4), and Candida albicans (ATCC 10231), and the antioxidant, acetylcholinesterase (AChE) , α-glucosidase, and topoisomerase IIα inhibitory activities were performed in accordance with the primary

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• activity of the biocide alone. In 1993, Lehner et al. reported a very interesting study on the antagonistic effect of the complexation between HP-β-CD and a series of p-hydroxybenzoic acid esters against Candida albicans [43]. The authors investigated the complexation in aqueous solution by solubility

Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum

• Naoya Oku,
• Miyako Matsumoto,
• Kohsuke Yonejima,
• Keijiroh Tansei and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190

• . Antimicrobial testing against four Gram-positive bacteria (Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, and Streptomyces lividans), one Gram-negative bacterium (Escherichia coli), two yeasts (Candida albicans and Saccharomyces cerevisiae), and two fungi (Aspergillus oryzae and Penicillum

• strains were grown on agar media (Staphylococcus aureus FDA209P JC-1, Micrococcus luteus ATCC9341, Escherichia coli NIHJ JC-2, Saccharomyces cerevisiae S100, and Candida albicans A9540) or in Sabouraud broth (Penicillum chrysogenum NBRC4626, Streptomyces lividans TK23) overnight and then diluted with

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• amide resin as the amine-bearing component (Scheme 18) [84]. The synthesis of nikkomycin Z analogs 46 aimed in an examination of their ability to inhibit Candida albicans chitin synthases. The library consisting of 450 analogs 46 was obtained from: (i) reactions involving nucleoside aldehyde 41, Rink

• albicans chitin synthase 1 at the concentration of 10 µM. Among the most active analogs 46a–c, compound 46a showed a comparable activity (IC50 = 6.07 µM) as that determined for nikkomycin Z (IC50 = 9.49 µM). On the other hand, inhibitory activity of this compound toward Candida albicans chitin synthase 2

• (IC50 = 4.78 µM) was significantly lower than that of nikkomycin Z (IC50 = 0.06 µM). The remaining compounds 46 were inactive toward Candida albicans chitin synthase 2. Another approach to the solid-phase synthesis of nucleoside analogs was developed by Sun and Lee (Scheme 19) [85]. The library of 1344

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

• Jens Schmidt,
• Zeinab Khalil,
• Robert J. Capon and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

• coli ATCC 25922, and the fungus Candida albicans ATCC 90028. Conclusion In conclusion, this study illustrates the importance of biosynthetic considerations to both natural products and synthetic chemistry. Biosynthetic hypotheses provide natural product chemists with a framework to challenge the

New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum

• Qun Göthel and
• Matthias Köck

Beilstein J. Org. Chem. 2014, 10, 613–621, doi:10.3762/bjoc.10.52

• ) show cytotoxic activity against the L929 mouse fibroblasts, KB-31 epidermoid carcinoma, and the breast cancer cell line MCF7, although none of them showed activity in the antimicrobial assays against Gram-negative bacteria and the fungus Candida albicans. Many of the isolated compounds from Aka

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6