Palmarumycins from the mangrove fungus BCC 25093

Total synthesis of Palmarumycin BGs, C1and Guignardin E

“…The cytotoxic activities of 1-7 and 14 against the growth of tumor cell lines (HCT116, U87-MG, HepG2, BGC823 and PC9) were evaluated using a MTT assay 22 and the results were shown Scheme 2 Synthesis of Palmarumycin BG1-6, Guignardin E (1-6) and Palmarumycin C 1 (7). Reagents and conditions: (a) TsOH, toluene, reflux, 72 h, 57%; (b) PDC, Celite, t-BuOOH, benzene, rt, 24 h, 74%; (c) DDQ, benzene, reflux, 82%; (d) B-bromocatecholborane, DCM, 0 C, 75%; (e) Nbenzylcinchoninium chloride, t-BuOOH, NaOH (0.1 M), toluene/H 2 O, 0 C, 73%; (f) (PhSe) 2 , NaBH 4 , AcOH, EtOH, 0 C, 92%; (g) HCl (1 M), THF/ H 2 O, 10 C, 3 day, 96% for 6 + 13, dr ¼ 25 : 1; (h) NaBH 4 , MeOH, rt, 56% for 2 and 30% for 3, dr ¼ 2 : 1; (i) NaBH 4 , MeOH, rt, 23% for 4, 9% for 5, and 60% for 14; (j) CeCl 3 $7H 2 O, MeOH/H 2 O, reflux, 79%.…”

“…KcF8, and the mangrove unidentied fungus BCC 25903, respectively. 6,7 Among these compounds, Palmarumycin BG5 showed excellent cytotoxicities against human breast carcinoma MCF-7 with IC 50 7.6 mM and promyelocytic leukemia HL60 with IC 50 1.9 mM, Guignardins E, F and Palmarumycin C 1 exhibited signicant cytotoxicities against 10 human tumor cell lines, such as MCF-7 with LD 50 8.79, 6.48 and 3.08 mM, HL60 with LD 50 2.94, 3.06 and 2.90 mM, and HeLa with LD 50 1.32, 0.38 and 1.24 mM et al 6 Many reports related to the total synthesis, structure modication, and biological activity evaluation of the spirobisnaphthalene natural products have appeared in recent years. [8][9][10][11][12][13][14][15][16][17][18][19][20] The synthesis of Palmarumycin CP 17 and its analogues were completed in our laboratory, and the bioassay results showed that they have antifungal activity against several phytopathogens.…”

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

“…272 A Lasiodiplodia strain yielded two cytotoxic and antibacterial chlorinated preussomerins, chloropreussomerins A ( 632 ) and B ( 633 ), along with new natural product 634 , 273 whilst an unidentified mangrove fungus BCC 25093 yielded five cytotoxic preussomerins, palmarumycins P 1 –P 5 ( 635–639 ). 274 …”

“…272 A Lasiodiplodia strain yielded two cytotoxic and antibacterial chlorinated preussomerins, chloropreussomerins A (632) and B (633), along with new natural product 634, 273 whilst an unidentied mangrove fungus BCC 25093 yielded ve cytotoxic preussomerins, palmarumycins P 1 -P 5 (635-639). 274 Compared to benzoquinones, anthraquinone derivatives are abundant in various mangrove-associated fungi and possess a wide range of biological activities. This family of polyketides with 38 members is characterized.…”

Anteaglonialides A–F and Palmarumycins CE1–CE3 from Anteaglonium sp. FL0768, a Fungal Endophyte of the Spikemoss Selaginella arenicola

“…FL0768 (Anteagloniaceae, Pleosporales, Pezizomycotina, Ascomycota), an endophytic fungus isolated from the living photosynthetic tissue of sand spikemoss ( Selaginella arenicola ; Selaginellaceae). Fractionation of this extract led to the isolation of six metabolites bearing a spiro­[6-(tetrahydro-7-furanyl)­cyclohexane-1,2′-naphtho­[1,8- de ]­[1,3]-dioxin]-10-one carbon skeleton, named anteaglonialides A–F ( 1 – 6 ), three new palmarumycin analogues, palmarumycins CE 1 –CE 3 ( 7 – 9 ), and nine known spirobisnaphthalenes, palmarumycins CP 5 ( 10 ), CP 4a ( 11 ), CP 3 ( 12 ), , CP 17 ( 13 ), CP 2 ( 14 ), and CP 1 ( 15 ), CJ-12,371 ( 16 ), 4- O -methyl CJ-12,371 ( 17 ), and palmarumycin CP 4 ( 18 ), together with a possible artifact, 4a(5)-anhydropalmarumycin CE 2 ( 8a ), formed from 8 , and four other known metabolites, O -methylherbarin ( 19 ), herbarin ( 20 ), herbaridine B ( 21 ), and hyalopyrone ( 22 ) …”