A new norkaurane-gamma-lactone from Parinari sprucei

The title tetracyclic diterpenoid, 10,13,16,17-tetrahydroxy-9-methyl-15-oxo-20-norkaurane-18,10-carbolactone hemihydrate, C(20)H(28)O(6).0.5H(2)O, is a plant metabolite from Parinari sprucei, part of the Venezuelan Amazon flora. The asymmetric unit consists of two nearly identical molecules of the diterpenoid and one molecule of water. Some of the geometric parameters reflect steric strain in the molecule. The extended structure is characterized by hydrogen bonds and weaker hydrogen-mediated interactions, which involve all of the hydroxy groups and propagate in sheets that coincide with the (002) family of planes. The water molecule acts as a double hydrogen-bond donor and single acceptor and thus plays a critical role in the pattern of intermolecular interactions.