Circumdatin H is an
alkaloid
Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids.
Alkaloids are produced by a large varie ...
. It was isolated, along with related compounds, from the fungus ''
Aspergillus ochraceus
''Aspergillus ochraceus'' is a mold species in the genus ''Aspergillus'' known to produce the toxin ochratoxin A, one of the most abundant food-contaminating mycotoxins, and citrinin. It also produces the dihydroisocoumarin mellein. It is a fil ...
''.
Circumdatin C, and circumdatin F are prototypical members, while other members such as circumdatin D, circumdatin E and circumdatin H have an additional tetrahydropyrrole ring.
The compounds of this group are considered to be useful
chemotaxonomic markers. Among these circumdatin H and circumdatin E are able to inhibit the mitochondrial respiratory chain in submitochondrial particles from beef heart, presumable by interfering with
NADH oxidase
Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an ade ...
activity (IC
50 1.5 μM and 2.5 μM, respectively).
First total synthesis of circumdatin H was reported starting from anthranilic acid.
References
{{Reflist
Alkaloids found in fungi