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R -Pyrisulfoxin C ( 1 ),  S -pyrisulfoxin D [(+)- 2 ],  R -pyrisulfoxin D [(–)- 2 ], pyrisulfoxin E ( 13 ),  S -pyrisulfoxin F [(+)- 14 ], and  R -pyrisulfoxin F [(–)- 14 ], six new caerulomycin derivatives with a 2,2′-bipyridine skeleton, were obtained from the cultures of the endophytic  Streptomyces albolongus  EA12432 with  Aconitum carmichaeli  (Ranunculaceae). Additionally, the racemic pyrisulfoxins A [(±)- 3 ] and B [(±)- 4 ] were further purified as optically pure compounds and identified the configurations for the first time. The racemic pyrisulfoxin D [(±)- 2 ] displayed significant cytotoxicity against a series of cancer cell lines with IC 50  values ranging from 0.92 to 9.71 μM. Compounds  7 ,  8 , and (±)- 3  showed cytotoxicity against the HCT-116, HT-29, BXPC-3, P6C, and MCF-7 cell lines. Notably, compounds  7  and  8  have a strong inhibition both on the proliferation of human colon cancer cells HCT-116 and HT-29 with IC 50  values ranging from 0.048 to 0.2 μM (doxorubicin, 0.21 and 0.16 μM), and compound  1  showed a selective inhibition on the proliferation of the gastric carcinoma cell lines, N87, with an IC 50  value of 8.09 μM. Optically pure compounds  R (–)- 14  and  S (+)- 14  showed weak cytotoxicity against HCT-116 and MCF-7 cell lines with the IC 50  values of 14.7 μM and 10.4 μM, respectively. Interestingly, compounds  1  and (±)- 2  didn't show cytotoxic activity against two human normal cell lines, HEK-293F and L02, with IC 50  values >100 μM.

Cytotoxic and Optically Active Pyrisulfoxins From the Endophytic Streptomyces albolongus EA12432