Psammaceratin A: A Cytotoxic Psammaplysin Dimer Featuring an Unprecedented (2Z,3Z)-2,3-Bis(aminomethylene)succinamide Backbone from the Red Sea Sponge Pseudoceratina arabica

Diaa T A Youssef; Hani Z Asfour; Lamiaa A Shaala

doi:10.3390/md19080433

Psammaceratin A: A Cytotoxic Psammaplysin Dimer Featuring an Unprecedented (2Z,3Z)-2,3-Bis(aminomethylene)succinamide Backbone from the Red Sea Sponge Pseudoceratina arabica

Mar Drugs. 2021 Jul 29;19(8):433. doi: 10.3390/md19080433.

Authors

Diaa T A Youssef¹, Hani Z Asfour², Lamiaa A Shaala^{3

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Affiliations

¹ Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
² Department of Medical Parasitology, Faculty of Medicine, Princess Al-Jawhara Center of Excellence in Research of Hereditary Disorders, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
³ Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
⁴ Department of Medical Laboratory Sciences, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
⁵ Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt.

Abstract

Bioassay-guided partition of the extract of the Red Sea sponge Pseudoceratina arabica and HPLC purification of the active fraction gave a psammaplysin dimer, psammaceratin A (1), along with psammaplysin A (2). The dimer comprises two units of psammaplysin A (2) connected via the terminal amines with an unprecedented (2Z,3Z)-2,3-bis(aminomethylene)succinamide moiety, and it represents the first dimer to be identified among the psammaplysin family. Data from 1D- and 2D-NMR and HRMS supported the chemical structures of the compounds. Psammaceratin A (1) and psammaplysin A (2) exhibited significant growth inhibition of HCT 116, HeLa, and MBA-MB-231 cells down to 3.1 μM.

Keywords: Pseudoceratina arabica; Red Sea sponge; cell lines’ growth inhibition; marine alkaloids; psammaceratin A; psammaplysin A; psammaplysin dimer.

MeSH terms

Amides / chemistry*
Animals
Antineoplastic Agents / pharmacology*
Aquatic Organisms / chemistry*
HeLa Cells / drug effects
Humans
Indian Ocean
Porifera / chemistry*
Structure-Activity Relationship
Succinates / chemistry*

Substances

Amides
Antineoplastic Agents
Succinates
succinamide

Grants and funding

1014/Deputyship for Research & Innovation, Ministry of Education in Saudi Arabia