Sphaerococcus coronopifolius

Bromosphaerol (161) is a dibromo-diterpenoid from the red alga Sphaerococcus coronopifolius. Its structure was determined through a combination of n.m.r. spectroscopy and X-ray analysis of a degradation product. 

Bavoso A, Cafieri F, De Napoli L, Di Blasio B, Fattomsso E, Pavone V, Santacroce C (1987) Isolation and Structure Determination of Norsphaerol, a Bis-nor-Diterpene from the Red Alga Sphaerococcus coronopifolius. Gazz Chim Ital 117 87... 

Etahiri S, Bultel-Ponce V, Caux C, Guyot M (2001) New Bromoditerpenes from the Red Alga Sphaerococcus coronopifolius. J Nat Prod 64 1024... 

In contrast to the abundance of the sesquiterpenoids, the halogenated diterpenoids are rare compounds found only in some Laurencia species and in the Mediterranean alga Sphaerococcus coronopifolius (Fenical et al., 1976 Fattorusso et al., 1976). The diterpenoids concinndiol (33) (Sims et al., 1973) and iriediol (34) (Fenical et al., 1975) represent most diterpenoid skeletons in Laurencia, while the uncommon primary halide functionality of sphaerococcenol A (35) is unique to S. coronopifolius. The sole example of a halogenated triterpenoid is the squalene-derived compound 36 from the... 

Fattorusso, E., Magno, S., Santacroce, C., Sica, D., DiBlasio, B. and Pedone, C., 1976. Bromosphaerol, a new bromine-containing diterpenoid from the red a ga Sphaerococcus coronopifolius. Gazz. Chim. Ital., 106 779—780. 

Fenical, W., Finer, J. and Clardy, J., 1976. Sphaerococcenol A a new rearranged bromo-diterpene from the red alga Sphaerococcus coronopifolius. Tetrahedron Lett., 1976 731—734. 

Two bromoditerpenes sphaerolabdadiene-3,14-diol and bromosphaer-one isolated from the marine red algae Sphaerococcus coronopifolius from the Atlantic ocean, sea coast of Morocco, exhibited antibacterial... 

Etahiri, S., Bultel-ponce, V., Caux, C., and Guyot, M. (2001). New bromoditerpenes from red alga Sphaerococcus coronopifolius. /. Nat. Prod. 64,1024-1027. 

Special isopiene rule, 2669 Specific doses, 2423 Specific symptrans, 2423 Spectral generalizatiSpectrophotometric methods, 2073 Sperm count, 2420, 2421 Spermidine, 1732 Spermine, 1732 Sperm production, 2418 Sphacelariaceae, 2900-2901 Sphacelariales, 2900-2901 Sphaerococcaceae, 2890 Sphaerococcus coronopifolius, 2890 Sphaerotrichia japonica (Sphaerotrichia divaricata), 2896 Spherisorb ODS2, 3393 Spheroidene, 3270, 3271 Spheromastigote, 845 Spinacea oleracea, 864 Spinacia oleracea, 3584 Spindle cell sarcoma 45, 992 Spinosin, 2163 Spiranoid 5-lactone, 3472 Spiranthera, 735 Spirilloxanthin, 3268, 3270, 3271 Spirilloxanthin pathways, 3268, 3270, 3271 Spirostanols, ilXl-ZXiO, il il, 3239,... 

These carbon skeletons are very unequally represented, the last four deriving from the first (sphaerane) by successions of classical transpositions in terpenic series. Of the approximately 30 known compounds, about 18 have this skeleton of sphaerane. Among the few examples below, the first eight diterpenes are presented in chronological order of their discovery, and the last eight molecules each represent one of the six carbon skeletons related to sphaerane. For these 16 compotmds the spedes is not mentioned because it is always Sphaerococcus coronopifolius. 

Sphaerollanes I and II are nonbrominated diterpenes with the neodolabellane carbon, closely related to the new sphaeroane skeleton. They have recently been found in Sphaerococcus coronopifolius collected around Corfu Island, Greece. This carbon skeleton is usually found in Cnidaria (see Chapter 20, and this is probably the first mention of such compoimds in a red alga (Smyrniotopoulos, Vagias, and Roussis, 2009). 

The final nonbrominated diterpene with an original skeleton, sphaeropyrane, was isolated in 1988 from Sphaerococcus coronopifolius of the Bay of Naples, and includes a regular diterpenic skeleton. Its formation from ( ,2)-ger-anylhnalool was proposed (Figure 13.7 Cafieri et al, 1988). 

For general biogenetic pathways to all series of brominated diterpenes from Sphaerococcus coronopifolius, see Smyrniotopoulos, Vagias, and Roussis, 2009 Smyrniotopoulos et al, 2010a, 2010b. 

Cafieri, F., Fattorusso, E., Di Blasio, B., and Pedone, C. (1981) Diterpenes from the red alga Sphaerococcus coronopifolius. Structure of sphaerodiene and reassignment of structure for presphaerol. Tetrahedron Lett., 22, 4123-4126. 

Coronoprfoliol, a diterpene based on an unprecedented tetracyclic skeleton from the red algae Sphaerococcus coronopifolius. J. Org. Chem., 50, 3982-3984. 

De Rosa, S., De Stefano, S., Scarpelli, P., and Zavodnik, N. (1988) Terpenes from the red alga Sphaerococcus coronopifolius of the North Adriatic Sea. Phytochemistry, 27,1875-1878. 

Smyrniotopoulos, V, Quesada, A., Vagias, C., Moreau, D., Roussakis, C., and Roussis, V. (2008a) Cytotoxic bromoditerpenes from tile red alga Sphaerococcus coronopifolius. Tetrahedron, 64, 5184—5190. 

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