ABSTRACT
Two new steroids (1 and 2) and the known pregna-1,4,20-trien-3-one (3) have been isolated from the Pacific octocoral Carijoa multiflora. Compound 1 possesses a novel spiropregnane-based steroidal skeleton. The photochemical transformation of 3 into 1 allowed the assignment of the absolute configuration at C-10 of 1. The antibacterial activities of compounds 1 and 3 were evaluated against a panel of bacterial strains.
Subject(s)
Anthozoa/chemistry , Anti-Bacterial Agents/isolation & purification , Steroids/isolation & purification , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus cereus/drug effects , Enterococcus faecalis/drug effects , Escherichia coli/drug effects , Klebsiella pneumoniae/drug effects , Microbial Sensitivity Tests , Molecular Structure , Proteus mirabilis/drug effects , Salmonella/drug effects , Staphylococcus aureus/drug effects , Steroids/chemistry , Steroids/pharmacologyABSTRACT
Candida antarctica lipase (CAL) catalyses the regioselective cinnamoylation and benzoylation of the aglycone moiety of 10-hydroxyoleoside dimethyl ester a secoiridoid glucoside. This enzyme catalyses as well regioselective deacetylation of the aglycone moiety of 10,2',3',4',6'-pentaacetoxyoleoside dimethyl ester. Further action of the enzyme results in deacetylation at C-6' and C-4' of the glucoside moiety.
Subject(s)
Candida/enzymology , Iridoids/chemistry , Lipase/metabolism , Acetylation , Acylation , Catalysis , Magnetic Resonance Spectroscopy/standards , Molecular Conformation , Reference Standards , StereoisomerismABSTRACT
The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one (9), and the aglycone of elenoside (5) showed cytotoxic activity towards the HL-60 cell line (IC50 = 7.25 miroM, 5.41 microM and 2.06 miroM, respectively).
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Lignans/chemical synthesis , Quinones/chemical synthesis , Acanthaceae/chemistry , Cell Line, Tumor , Humans , Lignans/chemistry , Molecular StructureABSTRACT
Los lignanos ingeridos con los alimentos de origen vegetal pueden ser biotransformados por las bacterias del tracto intestinal de los mamíferos y posteriormente absorbidos, dando compuestos detectables en suero, saliva, orina, bilis y fluidos seminales. Estos compuestos son conocidos como enterolignanos o lignanos de mamíferos y, al igual que otros fitoestrógenos, imitan algunos de los efectos de los estrógenos. En la actualidad se cree que pueden ejercer un efecto quimioprotector contra cánceres hormonodependientes como son el cáncer de mama y de próstata
Lignans ingested with food of plant origin are biotransformated by intestinal bacteria of the mammals and then absorbed, giving compounds detectable in serum, saliva, urine, bile and seminal fluids. These compounds are known as enterolignans or mammalian lignans and, like other phytoestrogens, can have some estrogen-like effects. Nowadays it is believed that they could exert a chemoprotective effect against hormone-dependent cancer, such as breast and prostate cancer
Subject(s)
Humans , Lignans/administration & dosage , Lignans/metabolism , Diet , Prostatic Neoplasms/prevention & control , Breast Neoplasms/prevention & control , Biological AvailabilityABSTRACT
En lo que a actividad farmacológica se refiere, los lignanos son principalmente conocidos por su actividad citotóxica, que es particularmente importante en el grupo de los ciclolignanos. No obstante, estos productos naturales también son inhibidores de la fosfodiesterasa del AMPc, confieren protección frente a hepatotoxinas, actúan sobre el tracto gastrointestinal, sistema cardiovascular y sistema nervioso central. También han demostrado tener actividad antiinflamatoria, antivírica y sobre el factor activador de plaquetas (PAF). Finalmente, tienen propiedades fitoestrogénicas, que serán tratadas en la tercera parte de esta serie de artículos sobre lignanos
Regarding the pharmacological activities, lignans are mainly known by their cytotoxic activity that is very important in cyclolignans. Nevertheless, these natural products are also inhibitors of AMPc phosphodiesterase, protectors against hepatotoxins and they act on the gastrointestinal tract, cardiovascular system and central nervous system. They have al so shown antiinflammatory and antiviral activities, as well as on the platelet activating factor (PAF). Finally, they also have phytoestrogenic properties, that will be described in the third part of these series of papers on lignans
Subject(s)
Humans , Plant Preparations/pharmacology , Plants, Medicinal/chemistry , Plants, Medicinal/classification , Lignans/pharmacology , Plant Preparations/chemistry , Plant Preparations/toxicity , Lignans/isolation & purification , Lignans/toxicityABSTRACT
Los lignanos constituyen un grupo de productos naturales ampliamente distribuido en el reino vegetal, cuyas unidades estructurales son biosintetizadas a través de la ruta del ácido sikímico. Pese a la elevada diversidad de estructuras que presentan, poseen la característica común de estar formados por dos unidades de fenilpropano enlazadas por el átomo central de sus cadenas laterales. Estos compuestos están presentes en desde briófitos y helechos hasta plantas superiores, donde desempeñan importantes funciones fisiológicas, principalmente de tipo defensivo
Lignans are a group of natural products widely distributed within the plant kingdom. The structural units of these compounds are biosynthesized via shikimic acid pathway. Although their structures can be very different, they have in common two units of phenylpropane bound by the central atom of their side chains. These compounds can be found in Bryophytes, ferns as well as in superior plants, in which they are responsible for important physiological functions, mostly of defensive kind
