Abstract
Caribbean sponges of the genus Smenospongia are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of S. aurea two new members of the smenamide family, namely smenamide F (1) and G (2). The structure of smenamide F (1) and G (2) was determined by spectroscopic analysis (NMR, MS, ECD). The relative and the absolute configuration at C-13, C-15, and C-16 was determined on the basis of the conformational rigidity of a 1,3-disubstituted alkyl chain system (i.e., the C-12/C-18 segment of compound (1). Smenamide F (1) and G (2) were shown to exert a selective moderate antiproliferative activity against cancer cell lines MCF-7 and MDA-MB-231, while being inactive against MG-63.
| Original language | English |
|---|---|
| Article number | 618 |
| Journal | Marine Drugs |
| Volume | 17 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Oct 30 2019 |
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Keywords
- Anti-tumor lead molecules
- Conformational analysis
- Marine natural products
- Smenamides
- Smenospongia aurea
- Solid tumor cell lines
- Structure elucidation
ASJC Scopus subject areas
- Drug Discovery
Cite this
Fast detection of two smenamide family members using molecular networking. / Caso, Alessia; Esposito, Germana; Sala, Gerardo Della; Pawlik, Joseph R.; Teta, Roberta; Mangoni, Alfonso; Costantino, Valeria.
In: Marine Drugs, Vol. 17, No. 11, 618, 30.10.2019.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Fast detection of two smenamide family members using molecular networking
AU - Caso, Alessia
AU - Esposito, Germana
AU - Sala, Gerardo Della
AU - Pawlik, Joseph R.
AU - Teta, Roberta
AU - Mangoni, Alfonso
AU - Costantino, Valeria
PY - 2019/10/30
Y1 - 2019/10/30
N2 - Caribbean sponges of the genus Smenospongia are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of S. aurea two new members of the smenamide family, namely smenamide F (1) and G (2). The structure of smenamide F (1) and G (2) was determined by spectroscopic analysis (NMR, MS, ECD). The relative and the absolute configuration at C-13, C-15, and C-16 was determined on the basis of the conformational rigidity of a 1,3-disubstituted alkyl chain system (i.e., the C-12/C-18 segment of compound (1). Smenamide F (1) and G (2) were shown to exert a selective moderate antiproliferative activity against cancer cell lines MCF-7 and MDA-MB-231, while being inactive against MG-63.
AB - Caribbean sponges of the genus Smenospongia are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of S. aurea two new members of the smenamide family, namely smenamide F (1) and G (2). The structure of smenamide F (1) and G (2) was determined by spectroscopic analysis (NMR, MS, ECD). The relative and the absolute configuration at C-13, C-15, and C-16 was determined on the basis of the conformational rigidity of a 1,3-disubstituted alkyl chain system (i.e., the C-12/C-18 segment of compound (1). Smenamide F (1) and G (2) were shown to exert a selective moderate antiproliferative activity against cancer cell lines MCF-7 and MDA-MB-231, while being inactive against MG-63.
KW - Anti-tumor lead molecules
KW - Conformational analysis
KW - Marine natural products
KW - Smenamides
KW - Smenospongia aurea
KW - Solid tumor cell lines
KW - Structure elucidation
UR - http://www.scopus.com/inward/record.url?scp=85074426040&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85074426040&partnerID=8YFLogxK
U2 - 10.3390/md17110618
DO - 10.3390/md17110618
M3 - Article
C2 - 31671549
AN - SCOPUS:85074426040
VL - 17
JO - Marine Drugs
JF - Marine Drugs
SN - 1660-3397
IS - 11
M1 - 618
ER -