Contributions to the Study of Marine Products. Xix. Chalinasterol

Abstract

Chalina arbuscula Verrill is one of the more common sponges of the coastal waters of New England. In its dried state it contains on the average about three per cent of acetone-soluble material, one to one and one-half per cent of unsaponifiable matter and from one-half to six-tenths of one per cent of a sterol of a degree of uniformity rarely encountered in sponges. The properties of 1450; [<x]d +25.2°(33.4 mg., a +0.28°). Both products gave no depression of melting points when mixed with the corresponding derivatives of campestanol. SUMMARY A new di-unsaturated sterol, chalinasterol, CísH^O, has been isolated from the sponges Chalina arbuscula Verrill and Tetilla laminaris Wilson.The sterol has been shown to be the C£4-isomer of brassicasterol by its hydrogenation to campesterol and campestanol, and by its ozonolysis, which yielded d-methylisopropylacetaldehyde.The significance of these observations has been discussed.New Haven, Conn.

The Chemical Constituents Of Tobacco And Tobacco Smoke

“…The physical constants were in most respects in accord with those given for chalinasterol (14,16), but the original authors later modified the structure proposed for chalinasterol (13) on the grounds that the work had originally been carried out on impure material, and the unsaturation was placed at 24(28> rather than at 22. The infrared spectrum of 24-methylenecholesterol was shown to be quite different from that of the tobacco sterol and the two are thus not identical.…”

Major Contributions towards Finding a Cure for Cancer through Chemotherapy: A Historical Review

“…The sea has been found to be a rich source of potentially useful drugs with antioxidant, immunostimulatory and anticancer activities (92). The interest in marine products developed after the identification of 2 nucleosides from the sponge Cryptotethia crypta by Werner Bergmann and Robert J. Feeney in 1951 (93). Since then, several cancer chemotherapeutic agents isolated from marine organisms have been approved.…”

Contributions to the Study of Marine Products. Xxi. Chondrillasterol

“…A sample was used which contained some cholestanyl acetate as an impurity. The ozonization was carried out as previously described (7) and the volatile aldehyde was isolated as the 2,4-dinitrophenylhydrazone. Several recrystallizations were required to raise the melting point to 115-116°, [a]" +5.7°(16.1 mg., a +0.03°).…”