Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

• Dimas J. P. Lima,
• Antonio E. G. Santana,
• Michael A. Birkett and
• Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

• nature, but not less important. They possess biological properties, such as nicotinic acetylcholine receptor (nAChR) ligand [10][11], CNS (central nervous system) activity [12][13], and chemical defense [14][15][16]. Structurally, homotropane alkaloids have different skeletons including [3.3.1], [4.2.1

• (−)-adaline concentration and reflex-fluid amount can be found within beetles. It suggests that internal aspects such as genetic factors may determine how much energy is invested in chemical defense [30]. Paul et al. [37] demonstrated that parental effects could play a crucial role in determining the color

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

• Xinlu Chen,
• Tobias G. Köllner,
• Wangdan Xiong,
• Guo Wei and
• Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

• terpenoids have many biological/ecological functions. They may serve as chemical defense [27][28] or as signals for attracting beneficial organisms. For social amoeba, multiple functions have been proposed, including chemical defense, attracting spore dispersers, and regulating development. In D. discoideum

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds

• Melissa M. Cadelis and
• Brent R. Copp

Beilstein J. Org. Chem. 2018, 14, 2229–2235, doi:10.3762/bjoc.14.197

• trimers. Taken together, these results support the hypothesis that onchidal (6) could be used in chemical defense in a similar manner to related sesquiterpenoid dialdehydes and enol esters. Masked and unmasked 1,4-dialdehyde natural products 1–6. Target onchidal model compounds 11–18. Pyrrole product 29

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

• Alexander Bogdanov,
• Cora Hertzer,
• Stefan Kehraus,
• Samuel Nietzer,
• Sven Rohde,
• Peter J. Schupp,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2017, 13, 502–519, doi:10.3762/bjoc.13.50

• -oxochatancin (16). Determining the metabolome of P. longicirrum and its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal. Keywords: chemical defense; chemoecology; natural compounds; Nudibranchia; Phyllodesmium longicirrum

• in the chemical defense. Later investigations provided toxicity ranking among the Alcyonarian soft corals. Sarcophyton species together with Sinularia, Lemnalia, Lobophytum and Nephthea soft corals showed the highest ichthyotoxicity levels [57][58]. The study on the defensive strategies of soft

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

• microbes, indicating a ”first chemical defense line” and ”long term prophylaxis” of P. triangulum ensuring protection and enhanced survival rates of the offspring. In a similar study, a detailed chemical analysis of rove beetles (Paederus spp.) led to the isolation of the complex polyketide pederin (3), a

A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

• Stefanie Wolfram,
• Hendryk Würfel,
• Stefanie H. Habenicht,
• Christine Lembke,
• Phillipp Richter,
• Eckhard Birckner,
• Rainer Beckert and
• Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

• ,4E)-deca-2,4-dien-9-ynal (DDY, 10) served as reactive group. DDY (10) mimics the natural product 2,4-decadienal that is produced by some diatoms as potential chemical defense metabolite against their grazers [34]. Structure-activity tests have revealed that 2,4-decadienal can be modified in the alkyl

Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

• Jie Zhang,
• Hong-Kui Zhang and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2013, 9, 2358–2366, doi:10.3762/bjoc.9.271

• -containing arthropods serving as a chemical defense against predators. It is not surprising that the alkaloids found in poison frogs can also be detected from ants, and most of them show remarkable bioactivities [2][3]. For example, formicine ants have been shown to be an arthropod source of the pumiliotoxin

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

• , D-24105 Kiel, Germany 10.3762/bjoc.8.30 Abstract Chemical defense of the invasive red alga Gracilaria vermiculophylla has been studied and compared to that of the noninvasive but related Gracilaria chilensis. Both species rely on a wound-activated chemical defense that makes them less attractive to

• potential of Gracilaria spp. is discussed. Keywords: activated chemical defense; invasive species; oxylipins; prostaglandins; red algae; regulation; Introduction The red alga Gracilaria chilensis is native along the Chilean coast and is commercially farmed for the production of agar hydrocolloids [1

• chemical defense against epiphytism has been demonstrated. This alga has two major lines of defense, including a rapid wound-activated production of oxylipins and a slower induced defense involving the up regulation of phospholipases and lipoxygenases and subsequent fatty-acid transformation [3][5]. Among