Total synthesis of Palmarumycin BGs, C₁and Guignardin E

Abstract

The first total syntheses of Palmarumycin BG1–3, BG5–6, C1 and Guignardin E were achieved. These compounds displayed significant inhibition activities against HCT116, U87-MG, HepG2, BGC823 and PC9 cell lines.

Spirobisnaphthalenes from Fungi, Biological activities and Total Synthesis: A Research Review

“…On the other hand, the reduction products of carbonyl group at C‐4 exhibited a weaker cytotoxic activity than those retaining carbonyl compounds. These results indicated that chlorine atom at C‐3 and the carbonyl group at C‐4 play a critical role in cytotoxicity [39] …”

“…Based on our previous research, palmarumycin C 2 was synthesized first starting from 5-methoxy-1-tetralone as the raw material through ketalization and N-benzyl cinchoninium chloride (BCNC)-catalyzed asymmetric epoxidation as the key steps as described in Scheme 5. [39] Then, palmarumycin C 2 was converted to palmarumycin C 1 (41) using cerium (III) chloride hydrate-promoted regioselective ring-opening and elimination reaction. The organoselenium mediated reduction of palmarumycin C 2 afforded palmarumycin BG1 as the sole product and the configuration of the β-position remained unchanged.…”

“…These results indicated that chlorine atom at C-3 and the carbonyl group at C-4 play a critical role in cytotoxicity. [39] Recently, the total synthesis of another chlorine-containing spirobisnaphthalene natural product Sch53825, which was Scheme 2. Synthesis of the putative palmarumycin B 6 .…”

Total synthesis, structure revision and cytotoxic activity of Sch 53825 and its derivatives

“…The cytotoxicity of Sch 53825 and its derivatives was evaluated against five human carcinoma cell lines (HCT116, U251, BGC823, Huh-7 and PC9) by MTT assay described in the literature. 11,12 Taxol was selected as the positive control. All of these cell lines (colon cancer cell HCT116, human glioma cell U251, gastric cancer cell BGC823, human hepatoma cells Huh-7 and lung carcinoma cell PC9), obtained from the American Type Culture Collection (ATCC) and purchased from the Cell Culture Center of Institute of Basic Medical Sciences, Peking Union Medical College, Chinese Academy of Medical Sciences, were cultured with 10% fetal bovine serum (FBS) and penicillin (100 U mL −1 )-streptomycin (100 μg mL −1 ) in Dulbecco's minimum essential medium (DMEM).…”

“…1b ) have been finished, and also revised the structure of palmarumycin B 6 . 12 a , b The bioassay results showed that palmarumycin B 6 had the larvicidal activity with an LC 50 value of 32.7 μM, 12 b and also palmarumycin C 1 and guignardin E exhibited significant cytotoxicity against several tumor cell lines with an IC 50 in the range of 2.45–15.39 μM towards HCT116, U87-MG, HepG2, BGC823 and PC9. 12 c…”