Metabolites of the higher fungi. Part 24. Cytochalasin N, O, P, Q, and R. New cytochalasins from the fungus Hypoxylon terricola Mill

Abstract

~~Punctaporonin B, cytochalasin C and D, and five n e w cytochalasins have been isolated from the culture medium and mycelium of the fungus Hypoxylon terricola. Cytochalasin C is the major metabolite. Cytochalasin N is the 5,6-epoxide of cytochalasin C, and cytochalasins 0 and P are t w o epimeric 6-hydroxy analogues. Cytochalasin Q is a 6,7-epoxide and R is a 6,7,13,14-diepoxide. The epoxides formed by cytochalasin C and D are described and the acid-and BF,-induced rearrangement products of cytochalasin N are identified.

New Cytochalasins from the Marine‐Derived Fungus Xylaria sp. SCSIO 156

“…The 1 H-and 13 C-NMR data of 1 were similar to those of the known cytochalasin Q (3) [6], except for the 13 C-NMR signal of 3 at d(C) 77.8 (C(18)) which was shifted to d(C) 50.7 in 1, suggesting the presence of a CH group in 1 instead of an O-bearing quaternary Catom in 3. This assumption was consistent with the result of the HMQC experiment, which assigned the H-atom at d(H) 3.17 -3.23 (m) to HÀC(18).…”

“…(SCSIO 156) was purified by silica gel (SiO 2 ) and ODS column chromatography (CC), as well as by Sephadex LH-20 CC guided by a brine shrimp (Artemia salina) assay and HPLC/UV to yield the two new cytochalasins 1 and 2, and the four known analogues 3 -6. Compounds 3 -6 were identified on the basis of their spectroscopic data and comparison with those reported [6] [7].…”

Three New Cytochalasins from the Marine‐Derived Fungus Spicaria elegans KLA03 by Supplementing the Cultures with L‐ and D‐Tryptophan

“…-Cytochalasins are a large group of fungal alkaloids with a wide range of biological activities targeting cytoskeletal processes [1]. Some of them exhibited a broad spectrum of activity, including inhibition of HIV-1 protease [2] as well as antibiotic and antitumor activities [3] [4]. During the studies on the production of bioactive metabolites by fungi, it was found that the marine fungus Spicaria elegans produced a number of cytochalasins.…”

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

“…isolated from Taxus brevifolia; 1,2 pestalotiopsolide A, teadolidol, and 6-epiteadolidol, highly oxidized caryophyllenes from a Pestalotiopsis sp. endophytic to the bark of Pinus taeda; 3 the 6-hydroxpunctaporonins, antibacterial metabolites from a fungicolous Pestalotiopsis disseminata; 4 fuscoatrol A, a cytotoxic agent from a marine-derived Humicola fuscoatra KMM 4629; 5 the punctaporonins (also named as punctatins), antifungal agents from a coprophilous Poronia punctata; [6][7][8][9][10][11] walleminol and walleminone, two cis-fused iso-caryophyllenes from the toxigenic fungus Wallemia sebi; 12 and Sch 725432, 601253, 601254, and 725434, antifungal agents from Chrysosporium pilosum. 13 During an ongoing search for new bioactive natural products from fungi of unique habitats, we initiated chemical studies of the fungi either inhabiting the fruiting body and larvae of Cordyceps sinensis 14 or its surface soil.…”