Oxygenated Terpenes from Indo-Pacific Nudibranchs: Scalarane Sesterterpenes from Glossodoris hikuerensis and 12-Acetoxy Dendrillolide A from Goniobranchus albonares
Free accessResearch articleFirst published online June, 2015
Oxygenated Terpenes from Indo-Pacific Nudibranchs: Scalarane Sesterterpenes from Glossodoris hikuerensis and 12-Acetoxy Dendrillolide A from Goniobranchus albonares
Two new scalarane sesterterpenes (1, 2) were characterized from an organic extract of a single specimen of the nudibranch Glossodoris hikuerensis collected from Bali. 12-Acetoxy dendrillolide A (10) was identified from specimens of Goniobranchus albonares, while dendrillolide A (11) was isolated both from G. albonares and its sponge diet. The structures and relative configuration of the new metabolites have been elucidated by analysis of their spectroscopic data.
Dilip deSilva E, ScheuerPJ. (1982) Furanoditerpenoids from the dorid nudibranch Casella atromarginata, Heterocycles, 17, 167–169.
2.
FontanaA, MolloE, RicciardiD, FahkrI, CiminoG. (1997) Chemical studies of Egyptian opistobranchs: Spongian diterpenoids from Glossodoris atromarginata. Journal of Natural Products, 60, 444–448.
3.
FontanaA, CavaliereP, UngurN, D'SouzaL, ParameswaramPS, CiminoG. (1999) New scalaranes from the nudibranch Glossodoris atromarginata and its sponge prey. Journal of Natural Products, 62, 1367–1370.
4.
GavagninM, MolloE, DocimoT, GuoYW, CiminoG. (2004) Scalarane metabolites of the nudibranch Glossodoris rufomarginata and its dietary sponge from the South China Sea. Journal of Natural Products, 67, 2104–2107.
5.
CiminoG, De RosaS, Se StefanoS, SodanoG. (1982) The chemical defense of four Mediterranean nudibranchs. Comparative and Biochemical Physiology, 73B, 471–474.
6.
SomervilleMJ, MolloE, CiminoG, RungpromW, GarsonMJ. (2006) Spongian diterpenes from Australian nudibranchs: an anatomically-guided chemical study of Glossodoris atromarginata. Journal of Natural Products, 69, 1086–1088.
7.
YongKWL, MudiantaIW, CheneyKL, MolloE, BlanchfieldJT, GarsonMJ. (2015) Isolation of norsesterterpenes and spongian diterpenes from Dorisprismatica (= Glossodoris) atromarginata. Journal of Natural Products, 78, 421–430.
8.
RogersSD, PaulVJ. (1991) Chemical defenses of three Glossodoris nudibranchs and their dietary Hyrtios sponges. Marine Ecology Progress Series, 77, 221–232.
9.
KazlauskasR, MurphyPT, QuinnRJ, WellsRJ. (1976) Heteronemin, a new scalarin type sesterterpene from the sponge Heteronema erecta, Tetrahedron Letters, 30, 2631–2634.
10.
CiminoG, De StefanoS, MinaleL, TrivelloneE. (1977) 12-Epi-scalarin and 12-epideoxoscalarin sesterterpenes from the sponge Spongia nitens. Journal of the Chemical Society, Perkin Transactions1, 1587–1593.
11.
NamSJ, KoH, ShinM, HamJ, ChinJ, KimY, KimH, ShinK, ChoiH, KangH. (2006) Farnesoid X-activated receptor antagonists from a marine sponge Spongia sp. Bioorganic and Medicinal Chemistry Letters, 16, 5398–5402.
12.
CrewsP, BescansaP. (1986) Sesterterpenes from a common marine sponge Hyrtios erecta. Journal of Natural Products, 49, 1041–1052.
13.
Bourguet-KondrackiML, MartinMT, DebitusC, GuyotM. (1994) 12-Epi-heteronemin: new sesterterpene from the marine sponge, Tetrahedron Letters, 35, 109–110.
14.
WangZH, ZhangZG, LiHC, DengWP. (2011) Concise stereoselective synthesis of marine sesterterpene 16-deacetoxy-12-epi-scalafuran acetate and its 14-epimer via intramolecular Diels-Alder addition. Tetrahedron, 67, 6939–6943.
15.
CiminoG, De StefanoS., Di LucciaA. (1979) Further sesterterpenes from the sponge Spongia nitens: 12-epi-scalaradial and 12,18-diepi-scalaradial. Experientia, 35, 1277–1278.
16.
BobzinSC, FaulknerDJ. (1989) Novel rearranged spongian diterpenes from the Palauan sponge Dendrilla sp. Journal of Organic Chemistry, 54, 5727–5731.
17.
BobzinSC, FaulknerDJ. (1989) Diterpenes from the marine sponge Aplysilla polyrhaphis. Journal of Organic Chemistry, 54, 3902–3907.
18.
MolinskiTF, FaulknerDJ, HeCH, Van DuyneGD, ClardyJ. (1986) Three new rearranged spongian diterpenes from Chromodoris macfarlandi; reappraissal of the structure of dendrillolides A and B. Journal of Organic Chemistry, 51, 4564–4567.
19.
SullivanB, FaulknerDJ. (1984) Metabolites of the marine sponge Dendrilla sp. Journal of Organic Chemistry, 49, 3204–3206.
20.
CarmelyS, CojocaruM, LoyaY, KashmanY. (1988) Ten new rearranged spongian diterpenes from two Dysidea species. Journal of Organic Chemistry, 53, 4801–4807.
