New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition

Ahmed N. Al-Rawahi; Raeid M.M. Abed; Najeeb Ur Rehman; Kashif Rafiq; Ajmal Khan; Abdul L. Khan; Majid Khan; Sobia Ahsan Halim; Fahad Al-Senafi; Huda Mahmoud; Ahmed Al-Harrasi

doi:10.1007/s10600-023-03990-0

New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition

Ahmed N. Al-Rawahi, Raeid M.M. Abed, Najeeb Ur Rehman^*, Kashif Rafiq, Ajmal Khan, Abdul L. Khan, Majid Khan, Sobia Ahsan Halim, Fahad Al-Senafi, Huda Mahmoud, Ahmed Al-Harrasi^*

^*Corresponding author for this work

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

Abstract

The ethyl acetate extract of the marine bacterial strain Streptomyces rochei sp. 81 was purified by silica gel column chromatography to obtain three diketopiperazines (1–3) and one straight chain fatty acid (4). The compounds were identified as cyclo(L-leu-N-ethenethiol-L-pro) (1), cyclo(L-Leu-L-Pro) (2), cyclo(L-Pro-D-Tyr) (3), and 2,4-dimethyldocasonoic acid (4) by HR-ESI-MS and NMR techniques. One new (1) and three known compounds (2–4) were screened for carbonic anhydrase-II (CA-II) inhibition and as a result 1 and 3 were found to be the most active compounds with IC₅₀ of 9.8 ± 0.56 and 10.9 ± 0.88 μM, respectively. The results indicated that these two compounds (1 and 3) can be promising candidates for anticancer drugs.

Original language	English
Pages (from-to)	346-350
Number of pages	5
Journal	Chemistry of Natural Compounds
Volume	59
Issue number	2
DOIs	https://doi.org/10.1007/s10600-023-03990-0
Publication status	Published - Mar 1 2023
Externally published	Yes

Keywords

Streptomyces rochei sp.81
carbonic anhydrase II
diketopiperazines
fatty acid

ASJC Scopus subject areas

General Chemistry
General Biochemistry,Genetics and Molecular Biology
Plant Science

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1007/s10600-023-03990-0

Cite this

Al-Rawahi, A. N., Abed, R. M. M., Rehman, N. U., Rafiq, K., Khan, A., Khan, A. L., Khan, M., Halim, S. A., Al-Senafi, F., Mahmoud, H., & Al-Harrasi, A. (2023). New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition. Chemistry of Natural Compounds, 59(2), 346-350. https://doi.org/10.1007/s10600-023-03990-0

Al-Rawahi, AN, Abed, RMM, Rehman, NU, Rafiq, K, Khan, A, Khan, AL, Khan, M, Halim, SA, Al-Senafi, F, Mahmoud, H & Al-Harrasi, A 2023, 'New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition', Chemistry of Natural Compounds, vol. 59, no. 2, pp. 346-350. https://doi.org/10.1007/s10600-023-03990-0

@article{e6d3db882b7149b6a8a7418472b3626b,

title = "New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition",

abstract = "The ethyl acetate extract of the marine bacterial strain Streptomyces rochei sp. 81 was purified by silica gel column chromatography to obtain three diketopiperazines (1–3) and one straight chain fatty acid (4). The compounds were identified as cyclo(L-leu-N-ethenethiol-L-pro) (1), cyclo(L-Leu-L-Pro) (2), cyclo(L-Pro-D-Tyr) (3), and 2,4-dimethyldocasonoic acid (4) by HR-ESI-MS and NMR techniques. One new (1) and three known compounds (2–4) were screened for carbonic anhydrase-II (CA-II) inhibition and as a result 1 and 3 were found to be the most active compounds with IC50 of 9.8 ± 0.56 and 10.9 ± 0.88 μM, respectively. The results indicated that these two compounds (1 and 3) can be promising candidates for anticancer drugs.",

keywords = "Streptomyces rochei sp.81, carbonic anhydrase II, diketopiperazines, fatty acid",

author = "Al-Rawahi, {Ahmed N.} and Abed, {Raeid M.M.} and Rehman, {Najeeb Ur} and Kashif Rafiq and Ajmal Khan and Khan, {Abdul L.} and Majid Khan and Halim, {Sobia Ahsan} and Fahad Al-Senafi and Huda Mahmoud and Ahmed Al-Harrasi",

note = "Publisher Copyright: {\textcopyright} 2023, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2023",

month = mar,

day = "1",

doi = "10.1007/s10600-023-03990-0",

language = "English",

volume = "59",

pages = "346--350",

journal = "Chemistry of Natural Compounds",

issn = "0009-3130",

publisher = "Springer New York",

number = "2",

}

TY - JOUR

T1 - New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition

AU - Al-Rawahi, Ahmed N.

AU - Abed, Raeid M.M.

AU - Rehman, Najeeb Ur

AU - Rafiq, Kashif

AU - Khan, Ajmal

AU - Khan, Abdul L.

AU - Khan, Majid

AU - Halim, Sobia Ahsan

AU - Al-Senafi, Fahad

AU - Mahmoud, Huda

AU - Al-Harrasi, Ahmed

PY - 2023/3/1

Y1 - 2023/3/1

N2 - The ethyl acetate extract of the marine bacterial strain Streptomyces rochei sp. 81 was purified by silica gel column chromatography to obtain three diketopiperazines (1–3) and one straight chain fatty acid (4). The compounds were identified as cyclo(L-leu-N-ethenethiol-L-pro) (1), cyclo(L-Leu-L-Pro) (2), cyclo(L-Pro-D-Tyr) (3), and 2,4-dimethyldocasonoic acid (4) by HR-ESI-MS and NMR techniques. One new (1) and three known compounds (2–4) were screened for carbonic anhydrase-II (CA-II) inhibition and as a result 1 and 3 were found to be the most active compounds with IC50 of 9.8 ± 0.56 and 10.9 ± 0.88 μM, respectively. The results indicated that these two compounds (1 and 3) can be promising candidates for anticancer drugs.

AB - The ethyl acetate extract of the marine bacterial strain Streptomyces rochei sp. 81 was purified by silica gel column chromatography to obtain three diketopiperazines (1–3) and one straight chain fatty acid (4). The compounds were identified as cyclo(L-leu-N-ethenethiol-L-pro) (1), cyclo(L-Leu-L-Pro) (2), cyclo(L-Pro-D-Tyr) (3), and 2,4-dimethyldocasonoic acid (4) by HR-ESI-MS and NMR techniques. One new (1) and three known compounds (2–4) were screened for carbonic anhydrase-II (CA-II) inhibition and as a result 1 and 3 were found to be the most active compounds with IC50 of 9.8 ± 0.56 and 10.9 ± 0.88 μM, respectively. The results indicated that these two compounds (1 and 3) can be promising candidates for anticancer drugs.

KW - Streptomyces rochei sp.81

KW - carbonic anhydrase II

KW - diketopiperazines

KW - fatty acid

UR - http://www.scopus.com/inward/record.url?scp=85151741801&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85151741801&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/53eb14e2-1001-3b04-8e42-a1d6984ddf57/

U2 - 10.1007/s10600-023-03990-0

DO - 10.1007/s10600-023-03990-0

M3 - Article

AN - SCOPUS:85151741801

SN - 0009-3130

VL - 59

SP - 346

EP - 350

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

IS - 2

ER -

New Sulfur-Containing Diketopiperazine from Marine-Derived Bacteria Streptomyces rochei sp. 81 with Potent Carbonic Anhydrase II Inhibition

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Cite this