Talarolactone A, an Isocoumarin Derivative Fused with Dihydrothiophene with Selective Antimigratory Activity from the Endolichenic Fungus Talaromyces sp.

Abstract

A 3,4-dihydroisocoumarin derivative fused with dihydrothiophene, talarolactone A (1), and two known compounds, terreusinone (2) and 4,6-dihydroxy-5-methylphthalide (3), were isolated from Talaromyces sp. associated with Xanthoparmelia angustiphylla. The structure of 1 was deduced from extensive spectroscopic data, electronic circular dichroism calculations, and X-ray diffraction analyses. A plausible biosynthetic pathway of 1 was further proposed. Compound 1 showed selective antimigratory activity in a wound-healing assay without appreciable cytotoxic activity.

Talaromarins A–F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35

“…By comparing physical and spectroscopic data with the literature, the 17 known homologues were identified as (R)-3-(3-hydroxypropyl)-8-hydroxy-3,4-dihydroisocoumarin (7) [35], peniciisocoumarin C (8) [28], 7-hydroxy-3-(3-hydroxypropyl)-8-methoxyisochroman-1-one (9) [34], 5,6-dihydroxy-3-(4-hydroxypentyl)-isochroman-1-one (10) [23], peniciisocoumarin F (11) [28], penicimarin G (12) [16], penicimarin C (13) [36], peniciisocoumarin A (14) [28], peniciisocoumarin B (15) [28], aspergillumarin A (16) [37], penicimarin H (17) [16], peniciisocoumarin D (18) [28], peniciisocoumarin G (19) [28], peniciisocoumarin E (20) [28], penicimarin N (21) [15], 6,8-dihydroxy-3-(2-hydroxypropyl)-7-methyl-1H-isochromen-1one (22) [38] and pestalotiorin (23) [39].…”

“…In summary, 23 secondary metabolites, including six new isocoumarin derivative talaromarins A-F (1-6) and 17 known analogues (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23) were obtained from the mangrovederived fungus Talaromyces flavus TGGP35. Compounds 6-11, 17-19 and 22 exerted similar or better antioxidant activity than the positive control trolox (IC 50 = 0.29 mM), with IC 50 values ranging from 0.009 to 0.27 mM.…”

“…The genus of Talaromyces has been studied and applied as a biocontrol agent, as a rich source of chitinolytic enzymes and producer of secondary metabolites [19][20][21]. Different classes of bioactive secondary metabolites have been found from the genus of Talaromyces [19][20][21], including some bioactive isocoumarins, such as selective antimigratory talarolactone A [22], α-glucosidase inhibitory sescandelin B and 3,4-dimethyl-6,8dihydroxyisocoumarin [23], antibacterial tratenopyrone [24], antibacteria and antifungi (-)-8-hydroxy-3-(4-hydroxypentyl)-3,4-dihydroisocoumarin [25]. These results indicated that the genus of Talaromyces can be used for the control of pathogenic bacteria, phytopathogenic microorganisms, diabetes control agents and so on [19,26].…”

New phenol and chromone derivatives from the endolichenic fungusDaldiniaspecies and their antiviral activities

“…[1][2][3][4][5] In recent years, a variety of secondary metabolites with impressive biological activities have been reported in endolichenic fungi. [6][7][8][9][10][11][12] The fungus Daldinia species was widely distributed around the world, and a total of 47 taxa in Daldinia were recognized by 2014, 13 however, only a limited number of secondary metabolites were reported from endolichenic fungus Daldinia species found in lichen. [14][15][16] The fungus Daldinia sp.…”

Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides

“…反应展示了优异的立体控制能力. 值得一提的是, 某些 天然产物 6～8 [12][13][14][15] 中也存在亚磺酰基(图 1b), 如鹅膏蕈 碱 8 [16][17][18] , 它是一种二环八肽, 具有高致死毒性(LD 50 ＝ 50 ～100 μg/kg), 是 RNA 聚合酶 II 的高选择性变构抑制 剂. 此外, 亚磺酰基是羰基的生物等排体 [19] , 在药物结 构设计和改造中也有着广泛的应用, 例如可用于提高药 物分子的水溶性, 影响药物代谢动力学性质, 增强药物 与靶标蛋白的相互结合能力等.…”