A new benzofuran glycoside and indole alkaloids from a sponge-associated rare actinomycete, Amycolatopsis sp.
Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1-3 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116.
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. kisi2016@snu.ac.kr.
Yun
Y
Kwon
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. yanberk@snu.ac.kr.
Seong-Hwan
SH
Kim
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. dicafree5@snu.ac.kr.
Yoonho
Y
Shin
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. baemoon89@snu.ac.kr.
Munhyung
M
Bae
ChunLab, Inc., Seoul National University, Seoul, 151-742, Korea. greg6044@gmail.com.
Byung-Yong
BY
Kim
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. sklee61@snu.ac.kr.
Sang Kook
SK
Lee
Department of Agricultural Biotechnology, College of Agriculture and Life Science, Seoul National University, Seoul 151-921, Korea. ohkibong@snu.ac.kr.
Ki-Bong
KB
Oh
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. shinj@snu.ac.kr.
Jongheon
J
Shin
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea. dongchanoh@snu.ac.kr.
Dong-Chan
DC
Oh
D000192:Actinomycetales / Q000302:isolation & purification / Q000378:metabolism*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045325:HCT116 Cells; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D011161:Porifera / Q000382:microbiology*; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D064210:Secondary Metabolism
D000970:Antineoplastic Agents; D001572:Benzofurans; D006027:Glycosides; D026121:Indole Alkaloids; D007211:Indoles; D011760:Pyrrolidinones; C000593352:amycolactam