Psammocindoles A-C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis

Oh Seok Kwon; Sungjin Ahn; Ju Eun Jeon; In Guk Park; Tae Hyung Won; Chung J. Sim; Hyeung Geun Park; Dong Chan Oh; Ki Bong Oh; Minsoo Noh; Jongheon Shin

doi:10.1021/acs.orglett.1c01410

Psammocindoles A-C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis

Oh Seok Kwon
, Sungjin Ahn
, Ju Eun Jeon
, In Guk Park
, Tae Hyung Won
, Chung J. Sim
, Hyeung Geun Park
, Dong Chan Oh
, Ki Bong Oh
, Minsoo Noh
, Jongheon Shin

Seoul National University
Hannam University

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

10 Scopus citations

Abstract

Psammocindoles A-C (1-3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A-D (5-8) were also synthesized. These natural products and synthetic analogues were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.

Original language	English
Pages (from-to)	4667-4671
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.1c01410
State	Published - 18 Jun 2021
Externally published	Yes

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title = "Psammocindoles A-C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis",

abstract = "Psammocindoles A-C (1-3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A-D (5-8) were also synthesized. These natural products and synthetic analogues were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.",

author = "Kwon, \{Oh Seok\} and Sungjin Ahn and Jeon, \{Ju Eun\} and Park, \{In Guk\} and Won, \{Tae Hyung\} and Sim, \{Chung J.\} and Park, \{Hyeung Geun\} and Oh, \{Dong Chan\} and Oh, \{Ki Bong\} and Minsoo Noh and Jongheon Shin",

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year = "2021",

month = jun,

day = "18",

doi = "10.1021/acs.orglett.1c01410",

language = "English",

volume = "23",

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TY - JOUR

T1 - Psammocindoles A-C

T2 - Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis

AU - Kwon, Oh Seok

AU - Ahn, Sungjin

AU - Jeon, Ju Eun

AU - Park, In Guk

AU - Won, Tae Hyung

AU - Sim, Chung J.

AU - Park, Hyeung Geun

AU - Oh, Dong Chan

AU - Oh, Ki Bong

AU - Noh, Minsoo

AU - Shin, Jongheon

PY - 2021/6/18

Y1 - 2021/6/18

N2 - Psammocindoles A-C (1-3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A-D (5-8) were also synthesized. These natural products and synthetic analogues were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.

AB - Psammocindoles A-C (1-3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A-D (5-8) were also synthesized. These natural products and synthetic analogues were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.

UR - https://www.scopus.com/pages/publications/85108448911

U2 - 10.1021/acs.orglett.1c01410

DO - 10.1021/acs.orglett.1c01410

M3 - Article

C2 - 34060857

AN - SCOPUS:85108448911

SN - 1523-7060

VL - 23

SP - 4667

EP - 4671

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Psammocindoles A-C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis

Abstract

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