A new trinor-guaiane sesquiterpene has been isolated from an Indonesian soft coral Anthelia sp. The planar structure, possessing an octahydroazulene skeleton, and relative stereochemistry were established by analyzing 1D and 2D NMR data, including NOE experiments. Its absolute stereochemistry was elucidated to be 1S, 4S, 7R, and 10R by comparing observed and calculated optical rotation values. The new compound showed weak cytotoxicity against NBT-T2 cells.
KelmanD., BenayahuY., KashmanY. (1999) Chemical defence of the soft coral Parerythropodium fulvum fulvum (Forskal) in the Red Sea against generalist reef fish. Journal of Experimental Marine Biology and Ecology, 238, 127–137.
2.
YamadaK., OgataN., RyuK., MiyamotoT., KomoriT., HiguchiR. (1997) Bioactive terpenoids from octocorallia. 3. A new eunicellin-based diterpenoid from the soft coral Cladiella sphaeroides.Journal of Natural Products, 60, 393–396.
3.
MurniA., HanifN., TanakaJ. (2013) A new cytotoxic dollabellane from the Indonesian soft coral Anthelia sp. Indonesian Journal of Chemistry, 13, 216–220.
LiY., CarboneM., VitaleR.M., AmodeoP., CastelluccioF., SiciliaG., MolloE., NappoM., CiminoG., GuoY.W., GavagninM. (2010) Rare casbane diterpenoids from the Hainan soft coral Sinularia depressa.Journal of Natural Products, 73, 133–138.
6.
LinY.C., El-RazekM.H.A., HwangT.L., ChiangM.Y., DaiC.F., ShenY.C. (2009) Asterolaurins A-F, xenicane diterpenoids from the Taiwanese soft coral Asterospicularia laurae.Journal of Natural Products, 72, 1911–1916.
7.
El-GamalA.A.H., WangS.K., DaiC.F., ChenI.G., DuhC.Y. (2005) Prenylbicyclogermacrane diterpenoids from the Formosan soft coral Nepthea pacifica.Journal of Natural Products, 68, 74–77.
8.
ChenD., ChenW., LiuD., van OfwegenL., ProkschP. (2013) Asteriscane-type sesquiterpenenoids from the soft coral Sinularia capillosa.Journal of Natural Products, 76, 1753–1763.
9.
PozaJ.J., FernandezR., ReyesF., RodriguezJ., JimenezC. (2008) Isolation, biological significance, synthesis, and cytotoxic evaluation of new natural parathiosteroid A-C and analogues from the soft coral Paragorgia sp. The Journal of Organic Chemistry, 73, 7978–7984.
10.
SjsstrandU., BohlinL., FisherL., ColinM., DjerassiC. (1981) Minor and trace sterols from marine invertebrates 28. A novel polyhydroxylated sterol from the soft coral Anthelia glauca.Steroids, 38, 347–354.
11.
CovalS.J., ScheuerP.J., MatsumotoG.K., ClardyJ. (1984) Two new xenicin from the octocoral Anthelia edmondsoni.Tetrahedron, 40, 3823–3828.
12.
GreenD., CarmelyS., BenayahuY., KashmanY. (1988) Antheliolide A & B: two new C24-acetoacetylated diterpenoids of the soft coral Anthelia glauca.Tetrahedron Letters, 29, 1605–1608.
13.
MushtiC.S., KimJ.H., CoreyE.J. (2006) Total synthesis of antheliolide A. Journal of the American Chemical Society, 128, 14050–14052.
14.
KashmanY., RudiA. (2004) On the biogenesis of marine isoprenoids. Phytochemistry Review, 3, 309–323.
15.
LinY.S., FazaryA.E., ChenaC.H., KuoY.H., ShenY.C. (2011) Asterolaurins G-J, new xenicane diterpenoids from the Taiwanese soft coral Asterospicularia laurae.Helvetica Chimica Acta, 94, 273–281.
16.
KimB.J., NamJ.H., KwonY.K., SoI., KimS.J. (2013) The role of waixenicin A as transient receptor potential metastatin 7 blocker. Basic & Clinical Pharmacology & Toxicology, 112, 83–89.
17.
MoriK., IguchiK., YamadaN., YamadaY. (1987) Stolonidiol, a new marine diterpenoid with a strong cytotoxic activity from the Japanese soft coral. Tetrahedron Letters, 28, 5673–5676.
18.
ShenY.C., PanY.L., KoC.L., KuoY.H., ChenC.Y. (2003) New dolabellanes from the Taiwanese soft coral Clavularia inflata.Journal of the Chinese Chemical Society, 50, 471–476.
19.
StephensP.J., DevlinF.J., CheesemanJ.R., FrischM.J. (2001) Calculation of optical rotation using density functional theory. Journal of Physical Chemistry A, 105, 5356–5371.
20.
StephensP.J., DevlinF.J., GasparriniF., CiogliA., SpinelliD., CosimelliB. (2007) Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation. Journal of Organic Chemistry, 72, 4707–4715.
21.
StephensP.J., PanJ.J., DevlinF.J., CheesemanJ.R. (2008) Determination of the absolute configurations of natural products using TDDFT optical rotation calculations: the iridoid oruwacin. Journal of Natural Products, 71, 285–288.