Citrinadin A derivatives from Penicillium citrinum, an endophyte from the marine red alga Dichotomaria marginata

T de JASAndrade, A Somensi, M N Lopes, A R Araujo, M Jaspars, D H S Silva

Research output: Contribution to journalAbstract

Abstract

Fungi isolated from marine organisms have been shown to produce interesting secondary metabolites which may represent an important source for bioprospection. Quinolizidine alkaloids isolated from Penicillium citrinum present a unique spiroindolinone moiety fused to a quinolizidine bicyclic unit forming a pentacyclic structure. The fungal strain was isolated from Dichotomaria marginata, collected from Brazil SE coast, and was grown in sterile rice solid media, which was then extracted with MeOH. CC of the MeCN fr. over Sephadex LH-20 afforded four quinolizidine alkaloids (1 – 4) after purification by HPLC-DAD. Their identification was based on spectral analyses, in addition to comparison with literature data and Antimarin® databank. UV data indicated the presence of similar chromophores with λmax 335nm, associated to the indolinone moiety. HRMS analyses of the isolated compounds indicated their molecular formula and 1D and 2D NMR data led to the identification of 1 – 4 as citrinadin A, citrinadin B, 18-dehydroxy-citrinadin B and chrysogenamide. Such compounds exhibited cytotoxicity against murine leukemia and human epidermoid carcinoma KB cells in previous studies, and thus our results may represent an important contribution for the exploration of marine biodiversity.
Original languageEnglish
Article numberPC37
Pages (from-to)776
Number of pages1
JournalPlanta Medica
Volume80
Issue number10
DOIs
Publication statusPublished - Jul 2014
Event55th Annual Meeting of the American-Society-of-Pharmacognosy (ASP) - Oxford, Montserrat
Duration: 2 Aug 20146 Aug 2014

Cite this

Citrinadin A derivatives from Penicillium citrinum, an endophyte from the marine red alga Dichotomaria marginata. / de JASAndrade, T; Somensi, A; Lopes, M N; Araujo, A R; Jaspars, M; Silva, D H S.

In: Planta Medica, Vol. 80, No. 10, PC37, 07.2014, p. 776.

Research output: Contribution to journalAbstract

de JASAndrade, T ; Somensi, A ; Lopes, M N ; Araujo, A R ; Jaspars, M ; Silva, D H S. / Citrinadin A derivatives from Penicillium citrinum, an endophyte from the marine red alga Dichotomaria marginata. In: Planta Medica. 2014 ; Vol. 80, No. 10. pp. 776.
@article{4dc141b6a8964a69836c944d3f5d5138,
title = "Citrinadin A derivatives from Penicillium citrinum, an endophyte from the marine red alga Dichotomaria marginata",
abstract = "Fungi isolated from marine organisms have been shown to produce interesting secondary metabolites which may represent an important source for bioprospection. Quinolizidine alkaloids isolated from Penicillium citrinum present a unique spiroindolinone moiety fused to a quinolizidine bicyclic unit forming a pentacyclic structure. The fungal strain was isolated from Dichotomaria marginata, collected from Brazil SE coast, and was grown in sterile rice solid media, which was then extracted with MeOH. CC of the MeCN fr. over Sephadex LH-20 afforded four quinolizidine alkaloids (1 – 4) after purification by HPLC-DAD. Their identification was based on spectral analyses, in addition to comparison with literature data and Antimarin{\circledR} databank. UV data indicated the presence of similar chromophores with λmax 335nm, associated to the indolinone moiety. HRMS analyses of the isolated compounds indicated their molecular formula and 1D and 2D NMR data led to the identification of 1 – 4 as citrinadin A, citrinadin B, 18-dehydroxy-citrinadin B and chrysogenamide. Such compounds exhibited cytotoxicity against murine leukemia and human epidermoid carcinoma KB cells in previous studies, and thus our results may represent an important contribution for the exploration of marine biodiversity.",
author = "{de JASAndrade}, T and A Somensi and Lopes, {M N} and Araujo, {A R} and M Jaspars and Silva, {D H S}",
note = "Fungi isolated from marine organisms have been shown to produce interesting secondary metabolites which may represent an important source for bioprospection. Quinolizidine alkaloids isolated from Penicillium citrinum present a unique spiroindolinone moiety fused to a quinolizidine bicyclic unit forming a pentacyclic structure. The fungal strain was isolated from Dichotomaria marginata, collected from Brazil SE coast, and was grown in sterile rice solid media, which was then extracted with MeOH. CC of the MeCN fr. over Sephadex LH-20 afforded four quinolizidine alkaloids (1 – 4) after purification by HPLC-DAD. Their identification was based on spectral analyses, in addition to comparison with literature data and Antimarin{\circledR} databank. UV data indicated the presence of similar chromophores with λmax 335nm, associated to the indolinone moiety. HRMS analyses of the isolated compounds indicated their molecular formula and 1D and 2D NMR data led to the identification of 1 – 4 as citrinadin A, citrinadin B, 18-dehydroxy-citrinadin B and chrysogenamide. Such compounds exhibited cytotoxicity against murine leukemia and human epidermoid carcinoma KB cells in previous studies, and thus our results may represent an important contribution for the exploration of marine biodiversity.",
year = "2014",
month = "7",
doi = "10.1055/s-0034-1382419",
language = "English",
volume = "80",
pages = "776",
journal = "Planta Medica",
issn = "0032-0943",
publisher = "Georg Thieme Verlag",
number = "10",

}

TY - JOUR

T1 - Citrinadin A derivatives from Penicillium citrinum, an endophyte from the marine red alga Dichotomaria marginata

AU - de JASAndrade, T

AU - Somensi, A

AU - Lopes, M N

AU - Araujo, A R

AU - Jaspars, M

AU - Silva, D H S

N1 - Fungi isolated from marine organisms have been shown to produce interesting secondary metabolites which may represent an important source for bioprospection. Quinolizidine alkaloids isolated from Penicillium citrinum present a unique spiroindolinone moiety fused to a quinolizidine bicyclic unit forming a pentacyclic structure. The fungal strain was isolated from Dichotomaria marginata, collected from Brazil SE coast, and was grown in sterile rice solid media, which was then extracted with MeOH. CC of the MeCN fr. over Sephadex LH-20 afforded four quinolizidine alkaloids (1 – 4) after purification by HPLC-DAD. Their identification was based on spectral analyses, in addition to comparison with literature data and Antimarin® databank. UV data indicated the presence of similar chromophores with λmax 335nm, associated to the indolinone moiety. HRMS analyses of the isolated compounds indicated their molecular formula and 1D and 2D NMR data led to the identification of 1 – 4 as citrinadin A, citrinadin B, 18-dehydroxy-citrinadin B and chrysogenamide. Such compounds exhibited cytotoxicity against murine leukemia and human epidermoid carcinoma KB cells in previous studies, and thus our results may represent an important contribution for the exploration of marine biodiversity.

PY - 2014/7

Y1 - 2014/7

N2 - Fungi isolated from marine organisms have been shown to produce interesting secondary metabolites which may represent an important source for bioprospection. Quinolizidine alkaloids isolated from Penicillium citrinum present a unique spiroindolinone moiety fused to a quinolizidine bicyclic unit forming a pentacyclic structure. The fungal strain was isolated from Dichotomaria marginata, collected from Brazil SE coast, and was grown in sterile rice solid media, which was then extracted with MeOH. CC of the MeCN fr. over Sephadex LH-20 afforded four quinolizidine alkaloids (1 – 4) after purification by HPLC-DAD. Their identification was based on spectral analyses, in addition to comparison with literature data and Antimarin® databank. UV data indicated the presence of similar chromophores with λmax 335nm, associated to the indolinone moiety. HRMS analyses of the isolated compounds indicated their molecular formula and 1D and 2D NMR data led to the identification of 1 – 4 as citrinadin A, citrinadin B, 18-dehydroxy-citrinadin B and chrysogenamide. Such compounds exhibited cytotoxicity against murine leukemia and human epidermoid carcinoma KB cells in previous studies, and thus our results may represent an important contribution for the exploration of marine biodiversity.

AB - Fungi isolated from marine organisms have been shown to produce interesting secondary metabolites which may represent an important source for bioprospection. Quinolizidine alkaloids isolated from Penicillium citrinum present a unique spiroindolinone moiety fused to a quinolizidine bicyclic unit forming a pentacyclic structure. The fungal strain was isolated from Dichotomaria marginata, collected from Brazil SE coast, and was grown in sterile rice solid media, which was then extracted with MeOH. CC of the MeCN fr. over Sephadex LH-20 afforded four quinolizidine alkaloids (1 – 4) after purification by HPLC-DAD. Their identification was based on spectral analyses, in addition to comparison with literature data and Antimarin® databank. UV data indicated the presence of similar chromophores with λmax 335nm, associated to the indolinone moiety. HRMS analyses of the isolated compounds indicated their molecular formula and 1D and 2D NMR data led to the identification of 1 – 4 as citrinadin A, citrinadin B, 18-dehydroxy-citrinadin B and chrysogenamide. Such compounds exhibited cytotoxicity against murine leukemia and human epidermoid carcinoma KB cells in previous studies, and thus our results may represent an important contribution for the exploration of marine biodiversity.

U2 - 10.1055/s-0034-1382419

DO - 10.1055/s-0034-1382419

M3 - Abstract

VL - 80

SP - 776

JO - Planta Medica

JF - Planta Medica

SN - 0032-0943

IS - 10

M1 - PC37

ER -