Organic constituents of the deep-sea precious corals Gerardia and Corallium spp.

Date
1980
Authors
Schwartz, Robert Eugene
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Abstract
In Hawaii deep-sea (-350 m) corals are collected commercially for the production of jewelry. Maui Divers, Inc. operates the manned minisubmersible Star II in the Makapuu beds found in the Molokai Channel off the island of Oahu. Although a large number of deep-sea corals are found in Hawaii, gold coral (Gerardia sp.) and pink coral (Corallium sp.) are commercially two of the most important in the production of gems. Gerardia sp. (Family Parazoanthidae, Order Zoanthidea, Subclass Zoantharia, Class Anthozoa, Phylum Cnidaria) is a yellow-colored animal with a hard, golden endoskeleton, and is bioluminescent in its deep-sea environment. [l] Two new fluorescent nitrogenous pigments, derivatives of tetrazacyclopentazulene, have been isolated from this organism. The major constituent, 2-amino-3-methyl-5-dimethylamino-3H-pseudozoanthoxanthin (1), is a yellow solid whose structure was established by spectral and chemical means, as well as by X-ray diffraction. [2,3] The minor constituent of Gerardia sp., 2-amino-3- methyl-5-methylamino-3H-pseudozoanthoxanthin (2),differs from 1 by the absence of a methyl group according to the 1H NMR spectrum and mass spectrum. The structure of 2 was proven by transformation of 2 to 1 via methylation.[3] Norpseudozoanthoxanthin (3), isolated from Parazoanthus axinellae by Prota and coworkers, [4,5] is typical of previously isolated pseudozoanthoxanthins which differ from 1 and 2 in the relationship between the nuclear N-methyl and the ring C-methyl. Pink coral (Corallium sp., Family Coralliidae, Order Gorgonacea, Subclass Alcyonaria, Class Anthozoa, Phylum Cnidaria) has yellow and orange polyps, and a hard pink endoskeleton. Four new diterpenoids containing a nine-membered carbocyclic ring fused to a δ-lactone were isolated from this organism. The structure of the major metabolite, coraxeniolide-A (4), was established by chemical and spectral means and confirmed by X-ray diffraction. The structures of the remaining lactones were obtained by correlation with 4. Corbohcin (5), a minor constituent of Corallium sp., contains a nine-membered ring and a single acetate; its structure was elucidated by spectral means. Paragorgia sp., another deep-sea gorgonian, appears to contain the identical five diterpenoids found in Corallium sp. Schmitz and co-workers [6] suggested the name xeniane for the carbon skeleton found in the coraxeniolides and corbohcin, upon isolation of xenicin (6) from the soft coral Xenia elongata. Related diterpenoids have been isolated from other species of soft corals belonging to the genus Xenia, as well as from the brown algal family Dictyotaceae.
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Thesis (Ph. D.)--University of Hawaii at Manoa, 1980.
Bibliography: leaves 162-166.
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xxi, 166 leaves, bound ill. 29 cm
Keywords
Corals -- Composition, Chemistry, Organic
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Theses for the degree of Doctor of Philosophy (University of Hawaii at Manoa). Chemistry; no. 1346
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