Bioactive Piperazic Acid-Bearing Cyclodepsipeptides, Lydiamycins E-H, from an Endophytic Streptomyces sp. Associated with Cinnamomum cassia

Weihong Wang; Seungjin Kim; Thi Hanh Nguyen Vu; Ngoc Tung Quach; Eunseok Oh; Kyu-Hyung Park; Chanyoon Park; Youbin Cho; Hyeseon Jang; Eun Roh; JunI Lee; Eunmo Kang; SongJoo Han; Quyet-Tien Phi; Heonjoong Kang

doi:10.1021/acs.jnatprod.2c00902

Bioactive Piperazic Acid-Bearing Cyclodepsipeptides, Lydiamycins E-H, from an Endophytic Streptomyces sp. Associated with Cinnamomum cassia

J Nat Prod. 2023 Apr 28;86(4):751-758. doi: 10.1021/acs.jnatprod.2c00902. Epub 2023 Feb 22.

Authors

Weihong Wang^{1

2}, Seungjin Kim³, Thi Hanh Nguyen Vu^{4

5}, Ngoc Tung Quach^{4

5}, Eunseok Oh¹, Kyu-Hyung Park¹, Chanyoon Park³, Youbin Cho¹, Hyeseon Jang¹, Eun Roh³, JunI Lee¹, Eunmo Kang¹, SongJoo Han¹, Quyet-Tien Phi^{4

5}, Heonjoong Kang^{1

2

3}

Affiliations

¹ Laboratory of Marine Drugs, School of Earth and Environmental Sciences, Seoul National University, NS-80, Seoul 08826, Korea.
² Research Institute of Oceanography, Seoul National University, NS-80, Seoul 08826, Korea.
³ Interdisciplinary Graduate Program in Genetic Engineering, Seoul National University, NS-80, Seoul 08826, Korea.
⁴ Institute of Biotechnology, Vietnam Academy of Science and Technology, Hanoi 100000, Vietnam.
⁵ Graduate University of Science and Technology, Vietnam Academy of Science and Technology, Hanoi 100000, Vietnam.

PMID: 36812487
DOI: 10.1021/acs.jnatprod.2c00902

Abstract

A chemical investigation of the endophytic Streptomyces sp. HBQ95, associated with the medicinal plant Cinnamomum cassia Presl, enabled the discovery of four new piperazic acid-bearing cyclodepsipeptides, lydiamycins E-H (1-4), and one known compound (lydiamycin A). Their chemical structures, including absolute configurations, were defined by a combination of spectroscopic analyses and multiple chemical manipulations. Lydiamycins F-H (2-4) and A (5) exhibited antimetastatic activity against PANC-1 human pancreatic cancer cells without significant cytotoxicity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cinnamomum aromaticum* / chemistry
Humans
Plants, Medicinal*
Pyridazines* / chemistry
Streptomyces* / chemistry

Substances

piperazic acid
Pyridazines