SmI₂-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B

• Nils Marsch,
• Peter G. Jones and
• Thomas Lindel

Beilstein J. Org. Chem. 2015, 11, 1700–1706, doi:10.3762/bjoc.11.184

• plants [1][2][3] and also in fungi [4] and myxobacteria [5][6]. One example is raputindole A (1), isolated in 2010 from the Rutaceous tree Raputia simulans Kallunki [1], which exhibits a unique tetrahydrocyclopenta[f]indole partial structure (Figure 1) probably formed by dimerization of (E)-6-(3

• not effect any reaction, as we learned when trying to dimerize the natural product verticillatine B (20) from the Brazilian plants Borreria verticillata and Raputia simulans [2][3]. We had speculated on the participation of the benzenoid double bond in dimerization reactions which would have

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• diporphyrin analogues [20][28][29][30]. Xanthene-9H-ones are an important class of oxygen-containing heterocycles and are mainly found as secondary metabolites in higher plants and microorganisms. The naturally occurring and synthetic xanthones possess diverse pharmacological activities [31][32][33][34

Antioxidant potential of curcumin-related compounds studied by chemiluminescence kinetics, chain-breaking efficiencies, scavenging activity (ORAC) and DFT calculations

• Adriana K. Slavova-Kazakova,
• Silvia E. Angelova,
• Timur L. Veprintsev,
• Petko Denev,
• Davide Fabbri,
• Maria Antonietta Dettori,
• Maria Kratchanova,
• Vladimir V. Naumov,
• Aleksei V. Trofimov,
• Rostislav F. Vasil’ev,
• Giovanna Delogu and
• Vessela D. Kancheva

Beilstein J. Org. Chem. 2015, 11, 1398–1411, doi:10.3762/bjoc.11.151

• Utilization: From Plants to Pharmacy Shelf, 3–6 November 2013, Bansko, Bulgaria, is gratefully acknowledged. The calculations were performed on the computer system installed at IOCCP–BAS with the financial support of the Bulgarian Scientific Fund under Project “MADARA” (RNF01/0110, contract no. DO02-52/2008).

Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

• Qinggang Mei,
• Chun Wang,
• Zhigang Zhao,
• Weicheng Yuan and
• Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 1220–1225, doi:10.3762/bjoc.11.135

• ; Introduction The plants of the Genus Epimedium, also known as “Yin-Yang-Huo”, were used in traditional Chinese medicine and are believed to invigorate the kidney and enhance the “Yang”. For more than one thousand years, some plants of Epimedium have been widely used in China to treat cardiovascular diseases

• , amnesia, arthritis, asthenia, impotence, infertility, lumbago and other chronic illnesses [1][2]. Icariin (1), a 3,7-diglycosylflavone (Figure 1), is recognized as the major pharmacologically active ingredient of these plants [3][4], and has been used as the index for quality control of the herbs and

Adsorption mechanism and valency of catechol-functionalized hyperbranched polyglycerols

• Stefanie Krysiak,
• Qiang Wei,
• Klaus Rischka,
• Andreas Hartwig,
• Rainer Haag and
• Thorsten Hugel

Beilstein J. Org. Chem. 2015, 11, 828–836, doi:10.3762/bjoc.11.92

• development, mussels, barnacles and numerous other animals and plants have found a way for strong, long-term adhesion to wet surfaces [1]. Wet hydrophilic surfaces are difficult to be wetted by glues since the adhesive competes with the surface water layer [2]. Mussels can easily adhere to hydrophilic metal

Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates

• Qinggang Mei,
• Chun Wang,
• Weicheng Yuan and
• Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 288–293, doi:10.3762/bjoc.11.33

• . Keywords: benzylation; deacetylation; kaempferol; methylation; regioselectivity; Introduction Kaempferol [2-(4-hydroxyphenyl)-3,5,7-trihydroxychromen-4-one] (Figure 1) and its derivatives are widely distributed in plants such as beans, broccoli, strawberries, teas, and propolis [1][2]. They are well known

• -methylkaempferol exhibits modest cytotoxicity [17]. These methylated derivatives of flavonols are found as natural products in relative low quantity, whereas kaempferol is relatively rich in plants. Therefore, it is quite worthwhile to develop procedures for the preparation of methylated derivatives of kaempferol

Synthesis of the furo[2,3-b]chromene ring system of hyperaspindols A and B

• Danielle L. Paterson and
• David Barker

Beilstein J. Org. Chem. 2015, 11, 265–270, doi:10.3762/bjoc.11.29

• Two novel racemic acylphoroglucinols, hyperaspidinols A (1) and B (2) (Figure 1) were recently isolated from the leaves of Hypericum chinense, a member of the St John’s Wort plants, which contains 490 flowering plants [1]. These plants have been used medicinally for treating illnesses such as

• hepatitis and depression, and as topical antimicrobials for wounds and snake bites [2][3][4][5]. There is great interest in secondary metabolites produced by plants from the Hypericum genus due to the bioactivity of many compounds that have been isolated from this source. A wide variety of compounds have

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• natural metabolites available from plants, phenolic compounds play a particularly important role in human health as they occur in significant amounts in many fruits, vegetables and medicinal plants. In this review natural phenolic compounds of plant origin with significant anti-angiogenic properties are

• compound found in plants and has been isolated from, for example, the flowers of carrot (Daucus carrota L., Apiaceae). In 2007, Park and co-workers [15] found no change in the vascular density in the chick chorioallantoic membrane (CAM) assay in the presence of HBA, indicating that HBA had no influence on

• . Resveratrol Resveratrol (8) is a natural polyphenol that belongs to the stilbene-type compounds and exists in a large number of plants. It has been primarily extracted from grape (Vitis vinifera L., Vitaceae) and mulberry (Morus L., Moraceae) fruits (Figure 4) [34]. It has antioxidant effects, anti-estrogenic

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

• Taiki Kojima,
• Rika Obata,
• Tsuyoshi Saito,
• Yasuaki Einaga and
• Shigeru Nishiyama

Beilstein J. Org. Chem. 2015, 11, 200–203, doi:10.3762/bjoc.11.21

• interesting biological activities [1]. Due to their plausible roles as defense substances of plants, lignans, neolignans, and their congeners are promising candidates for agricultural chemicals, and some of their antioxidant and/or anti-inflammatory properties may be utilized for biological research and as

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• , C22:6), which can be found in plants (flaxseed, walnut) and fish oil, respectively. ALA and linoleic acid (LA, C18:3 n−6 having the first double bond at the 6th carbon atom from the chain end, therefore classified as n−6 PUFA) are essential fatty acids, because they cannot be synthesized by the human

Trogopterins A–C: Three new neolignans from feces of Trogopterus xanthipes

• Soyoon Baek,
• Xuikui Xia,
• Byung Sun Min,
• Chanil Park and
• Sang Hee Shim

Beilstein J. Org. Chem. 2014, 10, 2955–2962, doi:10.3762/bjoc.10.313

• with IC50 values of 34.77–45.68 μM. Keywords: cytotoxic activity; neolignans; Trogopterus xanthipes; Introduction Chemical studies of natural products including ones derived from plants and microorganisms have led to the isolation of numerous novel metabolites with biological activities [1][2]. As a

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• oxidative stability; Introduction Aromatic and pharmaceutical plants have been used in both food and medicinal fields since ancient time. These valuable plants have been used directly as raw materials (such as teas/infusions, ground spices, dressings, sauces, etc.) [1][2][3], or indirectly by isolation of

• flavonolignan silybin from Silybum marianum L. or its disuccinate derivative, with hepatoprotective properties [4][5]. Ocimum genus (Lamiaceae family) is comprised of more than fifty species of herbs and shrubs growing in tropical and warm temperate regions [6][7][8][9]. All of these plants contain various

Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes

• Bodee Nutho,
• Wasinee Khuntawee,
• Chompoonut Rungnim,
• Piamsook Pongsawasdi,
• Peter Wolschann,
• Alfred Karpfen,
• Nawee Kungwan and
• Thanyada Rungrotmongkol

Beilstein J. Org. Chem. 2014, 10, 2789–2799, doi:10.3762/bjoc.10.296

• ; Introduction Flavonoids are polyphenolic compounds which are found in many plants as well as in several microorganisms [1][2]. They are herbal secondary metabolites with a wide range of biological and pharmacological activities and are used as therapeutic drugs having many benefits for protection and medical

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

• solubility. Carbendazim is a widely used systemic fungicide against different fungi affecting plants [38][39]. Its mechanism is linked to its antimitotic properties that inhibit the bacterial growth [40]. Due to its poor water-solubility, its application becomes a major constraining factor. In 1996, Schmidt

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

• Michail Syrpas,
• Ewout Ruysbergh,
• Christian V. Stevens,
• Norbert De Kimpe and
• Sven Mangelinckx

Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265

• components of microorganisms, algae, marine invertebrates, and some plants and animals [20][21]. Interest in these naturally occurring products is high as they often exhibit fascinating biological activities [22][23][24]. Furthermore, due to the reactivity of halogen substituents, this novel class of

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

• Yiyang Liu,
• Marc Liniger,
• Ryan M. McFadden,
• Jenny L. Roizen,
• Jacquie Malette,
• Corey M. Reeves,
• Douglas C. Behenna,
• Masaki Seto,
• Jimin Kim,
• Justin T. Mohr,
• Scott C. Virgil and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2014, 10, 2501–2512, doi:10.3762/bjoc.10.261

• –Danheiser chemistry [66][67]. E) Rhazinilam (−)-Rhazinilam (44) has been isolated from various plants including Rhazya strica decaisne [68], Melodinus australis [69], and Kopsia singapurensis [70]. Shortly after the first isolation, its structure was elucidated by single crystal X-ray diffraction analysis

Oligomerization of optically active N-(4-hydroxyphenyl)mandelamide in the presence of β-cyclodextrin and the minor role of chirality

• Helmut Ritter,
• Antonia Stöhr and
• Philippe Favresse

Beilstein J. Org. Chem. 2014, 10, 2361–2366, doi:10.3762/bjoc.10.246

• ; enzyme; oxidative coupling; phenol oligomer; Introduction Lignin consists of mechanical stabilizing polyphenols and thus plays an important role in many plants [1][2]. For the in vitro synthesis of polyphenols via oxidative coupling reactions, laccases and peroxidases are suitable enzymes to catalyze

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• efficiency; cyclodextrins; formation constant; phenylpropanoids; solubility; Introduction Phenylpropanoids (PPs), produced through the shikimic acid pathway, are one of the major groups of natural compounds. They could be found in a wide variety of plants (clove, anise, basil, tarragon, fennel, parsley

• , cinnamon, etc). PPs play a vital role in plants integrity and defense against biotic or abiotic stresses and are considered as “secondary metabolites” [1]. They are divided in several major classes such as coumarins, flavonoids, phenylpropenes and hydroxycinnamic acids [2]. PPs have an important

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• ]. Methyl jasmonates and dihydrojasmonates (2001) The jasmonates, which comprise of methyl jasmonate (11) and the corresponding jasmonic acid, are important cellular regulators in plants. They participate in various developmental processes and defence mechanisms against biotic and abiotic stresses [114

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

• of the cells, 1 is is not expected to target cell cycle-associated events, such as the synthesis of proteins, DNA, or RNA. Despite their structural diversity, many oxylipins induce a common stress response in plants and animal cells, and this activity is attributed to their ability to modify the

Efficient routes toward the synthesis of the D-rhamno-trisaccharide related to the A-band polysaccharide of Pseudomonas aeruginosa

• Aritra Chaudhury,
• Sajal K. Maity and
• Rina Ghosh

Beilstein J. Org. Chem. 2014, 10, 1488–1494, doi:10.3762/bjoc.10.153

• synthesis has seen a rapid development over the last two decades [5][6][7]. The D-rhamnoside motif is of particular interest with its presence established in the LPS/EPS systems of various bacterial strains which are pathogenic towards both plants and animals. These species include the Burkholderia cepacia

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

• Ulrike Groenhagen,
• Michael Maczka,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146

• compounds form a chemical structure space of volatiles released by bacteria and their number is limited, although this space is certainly only partially explored. Another group of volatile compounds forming a structure space is already known from the green part of plants (excluding flowery parts). The plant

Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX

• Anna M. Bogazkaya,
• Clemens J. von Bühler,
• Sebastian Kriening,
• Alexandrine Busch,
• Alexander Seifert,
• Jürgen Pleiss,
• Sabine Laschat and
• Vlada B. Urlacher

Beilstein J. Org. Chem. 2014, 10, 1347–1353, doi:10.3762/bjoc.10.137

• terpenoids in plants represents the most prominent example [14]. Heme-containing cytochrome P450 monooxygenases (P450 or CYP) are predominantly responsible for structural and functional diversity of terpenoids: allylic hydroxylation of parental monoterpenes leads to further diversification via sequential

• exclusively to two allylic alcohols with a notable preference for 12-hydroxynerylacetone (16, 72% and 75%, respectively) (Table 2). Discussion As mentioned in the introduction a large number of regioselective hydroxylation reactions occur in plants. Recently a geraniol 10-hydroxylase from the plant

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

• Hannes Mikula,
• Julia Weber,
• Dennis Svatunek,
• Philipp Skrinjar,
• Gerhard Adam,
• Rudolf Krska,
• Christian Hametner and
• Johannes Fröhlich

Beilstein J. Org. Chem. 2014, 10, 1129–1134, doi:10.3762/bjoc.10.112

• mycotoxins, especially altered derivatives formed through conjugation to sugar moieties or sulfate, emerge after metabolization by living plants. Due to changed chemical structures and properties compared to the parent mycotoxins, these conjugates can usually not be detected applying standard analytical

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

• , siphonodictyals B1–B3 (6–8) could be derived from siphonodictyals E1–E3 (1–3), respectively. Aromatic sulfates occur in a wide range of higher plants and animals, particularly those growing in marine, estuarine, or freshwater environments. This is probably due to the high content of inorganic sulfate in aquatic