Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori

Yern Hyerk Shin; Ji Yoon Beom; Beomkoo Chung; Yoonho Shin; Woong Sub Byun; Kyuho Moon; Munhyung Bae; Sang Kook Lee; Ki Bong Oh; Jongheon Shin; Yeo Joon Yoon; Dong Chan Oh

doi:10.1021/acs.orglett.9b00384

Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori

Yern Hyerk Shin
, Ji Yoon Beom
, Beomkoo Chung
, Yoonho Shin
, Woong Sub Byun
, Kyuho Moon
, Munhyung Bae
, Sang Kook Lee
, Ki Bong Oh
, Jongheon Shin
, Yeo Joon Yoon
, Dong Chan Oh

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

Bombyxamycins A and B (1 and 2) were discovered from a silkworm gut Streptomyces bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of 2, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.

Original language	English
Pages (from-to)	1804-1808
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.9b00384
State	Published - 15 Mar 2019

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title = "Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori",

abstract = "Bombyxamycins A and B (1 and 2) were discovered from a silkworm gut Streptomyces bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of 2, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.",

author = "Shin, \{Yern Hyerk\} and Beom, \{Ji Yoon\} and Beomkoo Chung and Yoonho Shin and Byun, \{Woong Sub\} and Kyuho Moon and Munhyung Bae and Lee, \{Sang Kook\} and Oh, \{Ki Bong\} and Jongheon Shin and Yoon, \{Yeo Joon\} and Oh, \{Dong Chan\}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

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doi = "10.1021/acs.orglett.9b00384",

language = "English",

volume = "21",

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T1 - Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori

AU - Shin, Yern Hyerk

AU - Beom, Ji Yoon

AU - Chung, Beomkoo

AU - Shin, Yoonho

AU - Byun, Woong Sub

AU - Moon, Kyuho

AU - Bae, Munhyung

AU - Lee, Sang Kook

AU - Oh, Ki Bong

AU - Shin, Jongheon

AU - Yoon, Yeo Joon

AU - Oh, Dong Chan

PY - 2019/3/15

Y1 - 2019/3/15

N2 - Bombyxamycins A and B (1 and 2) were discovered from a silkworm gut Streptomyces bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of 2, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.

AB - Bombyxamycins A and B (1 and 2) were discovered from a silkworm gut Streptomyces bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of 2, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.

UR - https://www.scopus.com/pages/publications/85062484412

U2 - 10.1021/acs.orglett.9b00384

DO - 10.1021/acs.orglett.9b00384

M3 - Article

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AN - SCOPUS:85062484412

SN - 1523-7060

VL - 21

SP - 1804

EP - 1808

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori

Abstract

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