Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• Massarilactones constitute a rare class of polyketides produced mainly by endophytic fungi. Given that semisynthetic derivatives often exhibit biological activities greater than those of the substrates, seven previously unreported derivatives of massarilactone D, compounds 2–8, were synthetized by acylation with

• ; nematicidal activity; Introduction Cancer continues to be responsible for morbidity and mortality all over the world. Endophytic fungi have been shown to be an important source of secondary metabolites endowed with interesting cytotoxic activities. However, resistance to cancer therapies is a persistent

• products can serve as effective scaffold for the design and synthesis of derivatives with improved biological activities [5][6][7]. Massarilactones are produced by marine and endophytic fungi and bear close biogenetic similarity to several other fungal PKS1-derived metabolites including rosigenin, the

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• almost always show Asn4 methylation. Further investigation into the substrate scope of PbtM1 would be interesting to determine its potential in peptide engineering [64]. An example for lysine N-methylation can be found in epichloëcyclins. This family of RiPPs is found in endophytic fungi of the genus

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• Abstract From a fresh root of Trema guineensis (Ulmaceae), endophytic fungi were isolated, among which a taxon belonging to the new species Diaporthe cameroonensis. This strain was fermented in shake flask batch cultures and the broth was extracted with ethyl acetate. From the crude extract, a hemiketal

• ; endophytic fungi; hemiketal polyketide; Introduction Endophytic fungi are organisms that reside almost ubiquitously inside the fresh healthy tissue of plants, and they may increase the resistance of the host tropical trees to survive in extreme conditions [1]. As the global diversity of endophytic fungi is

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• , Institute of Forest Sciences, University of Freiburg, Fohrenbühl 27, 79252 Stegen-Wittental, Germany 10.3762/bjoc.17.118 Abstract Plant volatiles play a major role in plant–insect interactions as defense compounds or attractants for insect herbivores. Recent studies have shown that endophytic fungi are

• ]. Endophytic fungi themselves can produce VOCs. Currently, around 300 fungal VOCs have been characterized, including aliphatic alcohols, ketones, aldehydes, acids and esters, terpenoids, benzenoids, naphthalene derivatives, and cycloalkanes [25][26][27]. Endophytic fungal VOCs are frequently described to

• exhibit antimicrobial activity; however, they are also known to induce the growth and vigor of the host plant and to shape plant community structure [27][28][29][30][31]. Furthermore, volatiles released from endophytic fungi can also affect insect behavior. Daisy et al. isolated the endophytic fungus

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

• Ken-ichi Nakashima,
• Junko Tomida,
• Takao Hirai,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

• ) lack the evidence that supports their assignments, i.e., the absolute configurations of α-diversonolic ester (3), aspergillusone B (4), and their related compounds are still unknown. As part of our research into compounds produced by endophytic fungi in Japan [7][8][9], we isolated two new diversonolic

• leaves of Selaginella tamariscana (Selaginellaceae) were cultivated in Tajimi City, Gifu, Japan. The methods of isolation and identification of endophytic fungi were performed in a similar manner as described previously [8]. Based on the DNA sequencing of ITS of rDNA and the D1/D2 domain of 26S rDNA

Synthesis of acremines A, B and F and studies on the bisacremines

• Nils Winter and
• Dirk Trauner

Beilstein J. Org. Chem. 2019, 15, 2271–2276, doi:10.3762/bjoc.15.219

• acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature. Keywords: meroterpenoid; natural product; selective oxidation; total synthesis; Introduction Endophytic fungi grow in a symbiotic

Volatiles from the xylarialean fungus Hypoxylon invadens

• Jeroen S. Dickschat,
• Tao Wang and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 734–746, doi:10.3762/bjoc.14.62

• (18), one of the major constituents in the H. invadens headspace extracts, has been reported before from various ascomycetes, especially from the genus Daldinia and other endophytic fungi [16][17][18][19][20][21][22][23][24][25]. It did, however, not constitute a major metabolite during the screening

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

• Tao Wang,
• Kathrin I. Mohr,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

• -4-chromanone (12) and 5-hydroxy-2-methyl-4-chromanone (13) were tentatively identified from their mass spectra. Compound 13, which exhibits antimicrobial activity, was previously isolated from various species of Daldinia [16][19][20][21][22] and several endophytic fungi, the latter of which have

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• a natural source: Coriandrone A isolated from the aerial parts of Coriandrum sativum [6] and other furo[3,2-h]isocoumarins have been reported as synthetic products [7][8][9]. In the last decade, our research group has been devoted to finding novel bioactive compounds from mangrove endophytic fungi

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• that they are mainly distributed in the Alternaria species and mycobionts. Especially endophytic fungi can be regarded as source organisms. Alternariol (17), altenuene (18), and alternariol 9-methyl ether (19) have been described from Alternaria sp. [17], botrallin (20) from Hyalodendriella sp. [18

• ]. Several dibenzo-α-pyrones have been isolated from plant parts. Purified from roots, bulbi, heartwood, or whole plant material, the origin of some plant-derived pyrones is not finally clarified, since the production by endophytic fungi cannot be excluded. Djalonensone was isolated from Anthocleista

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• of bioactivities including antibacterial [10], antifungal [6], antiviral [12], antioxidant [5], and cytotoxic [9]. In the last decade, our research group has been focused on isolating novel compounds from endophytic fungi growing on mangroves in the South China Sea and investigating their bioactivity