Conserved and species-specific oxylipin pathways in the wound-activated chemical defense of the noninvasive red alga Gracilaria chilensis and the invasive Gracilaria vermiculophylla

• Martin Rempt,
• Florian Weinberger,
• Katharina Grosser and
• Georg Pohnert

Beilstein J. Org. Chem. 2012, 8, 283–289, doi:10.3762/bjoc.8.30

• the up-regulated metabolites, arachidonic acid derived hydroxylated and dihydroxylated fatty acids are most prominent, with 7,8-dihydroxyeicosatetraenoic acid (7,8-di-HETE (3)) being the most active metabolite in the chemical defense against epiphytism. Recent work indicates that the invasive G

• an additional signal of an arachidonic acid derived metabolite with a characteristic UV spectrum of a conjugated tetraene. Purification yielded about 2.3 mg of an unstable metabolite, which was submitted to MS, 1D and 2D-NMR analysis. The molecular formula C20H28O2 was determined by HRMS–ESI ([M + Na

• ]+ calcd for 323.1986; found, 323.1982). 1H–1H COSY allowed us to follow the entire spin system of the metabolite, including 10 olefinic protons, 7 CH2, 1 CH3 and 1 CH groups (Scheme 1, spectra are shown in Supporting Information File 1). In combination with HMBC data all hydrogen and carbon signals were

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• , and is excreted in an inactive form via liver and kidneys. Fluconazole is 94% absorbed and its oral bioavailability is not affected by food or gastric pH. It is excreted unchanged in urine with t1/2 = 25–30 h. Itraconazole is largely metabolized in liver by cytochrome P450 3A4, an active metabolite is

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

• atorvastatin which has a five times greater potency then the initial lead, the fungal metabolite compactin (5, Figure 2). Although it was possible to construct such fully substituted pyrrole rings by ZnCl2-catalysed condensation reactions between a functionalised enamine 6 and simple benzoin (7), this method

Synthesis of (3R,5R)-harzialactone A and its (3R,5S)-isomer

• Gowravaram Sabitha,
• Rangavajjula Srinivas,
• Sukant K. Das and
• Jhillu S. Yadav

Beilstein J. Org. Chem. 2010, 6, No. 8, doi:10.3762/bjoc.6.8

• and biologically active secondary metabolites [1]. (+)-Harzialactone A (1), a marine metabolite isolated from the culture broth of a strain of Trichoderma harzianum OUPS-N115 by Numata and co-workers, exhibited antitumor and cytotoxic activities against cultured P388 cells [2]. The absolute

Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

• Pitak Nasomjai,
• David O'Hagan and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2009, 5, No. 37, doi:10.3762/bjoc.5.37

• phosphonate 8a was obtained (Figure 2) which confirmed its structure and stereochemical relationship to intermediate ribose-1-phosphate metabolite 5. Clearly, phosphonate 8a formed a 1:1 salt with the amine. Additionally, 23a and 22a were treated in separate reactions with acetic anhydride in dry pyridine [13

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

• unique activity was thought to originate from their ability to transform in vivo to generate the active metabolite. This was followed by decades of investigations to understand in detail their singular mode of action. It was found that the aziridine played a crucial role, allowing an irreversible bis

A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine

• Jian-Feng Zheng,
• Wen Chen,
• Su-Yu Huang,
• Jian-Liang Ye and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2007, 3, No. 41, doi:10.1186/1860-5397-3-41

• toward DNA repair-deficient yeast mutants;[7] azaspiracids are marine phycotoxins isolated from cultivated mussels in Killary harbor, Ireland;[8] and chlorofusin A is a novel fungal metabolite showing the potential as a lead in cancer therapy.[9] In addition, aza-spiropyrans C, being able to equilibrate

Multiple hydride reduction pathways in isoflavonoids

• Auli K. Salakka,
• Tuija H. Jokela and
• Kristiina Wähälä

Beilstein J. Org. Chem. 2006, 2, No. 16, doi:10.1186/1860-5397-2-16

• of isoflavones [10][16][17][18][19][20]. Deoxybenzoins (5) and propenols (6) Isoflavanones undergo a facile retro-Michael-type ring opening [21][55] under basic conditions to give the propenone intermediate 14 (Figure 2), sometimes considered [56] to be an independent isoflavone metabolite but