Five new diterpene glycosides, virescenosides Z4-Z8 (1-5) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined by HRESIMS and 1D and 2D NMR. Virescenosides Z4-Z8 contain rare altruronic acid 4C1 and 1C4 conformations as their carbohydrate components. Virescenosides Z5 and Z7 exhibit an unusual 16-chloro, 15-hydroxyethylgroup as their side chains.
BugniT.S., IrelandC.M. (2004) Marine-derived fungi and biologically diverse group of microorganisms. Natural Product Reports, 21, 143–162.
2.
BhaduryP., MohammadB.T., WrightP.C. (2006) The current status of natural products from marine fungi and their potential as anti-infective agents. Journal of Industrial Microbiology & Biotechnology, 33, 325–337.
DebbabA., AlyA.H., LinW.H., ProkschP. (2010) Bioactive compounds from marine bacteria and fungi. Microbial Biotechnology, 3, 544–563.
5.
AfiyatullovS.S., KuznetsovaT.A., IsakovV.V., PivkinM.V., Prokof'evaN.G., ElyakovG.B. (2000) New diterpene altrosides of the fungus Acremonium striatisporum isolated from a sea cucumber. Journal of Natural Products, 63, 848–850.
6.
AfiyatullovS.S., KalinovskyA.I., KuznetsovaT.A., IsakovV.V., PivkinM.V., DmitrenokP.S., ElyakovG.B. (2002) New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber. Journal of Natural Products, 65, 641–644.
7.
AfiyatullovS.S., KalinovskyA.I., KuznetsovaT.A., PivkinM.V., Prokof'evaN.G., DmitrenokP.S., ElyakovG.B. (2004) New glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber. Journal of Natural Products, 67, 1047–1051.
8.
AfiyatullovS.S., KalinovskyA.I., PivkinM.V., DmitrenokP.S., KuznetsovaT.A. (2006) New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber. Natural Product Research, 20, 902–908.
9.
ArtemchukN.Y. (1981) Microflora of USSR seas.Science, Moscow, 1–192.
10.
PodlasekC.A., WuJ., StripeW.A., BondoP.B., SerianniA.S. (1995) 13C-Enriched methyl aldopyranosides: structural interpretations of 13C – 1H spin-coupling constants and 1H chemical shifts. Journal of the American Chemical Society, 117, 8635–8644.
11.
LeonteinK., LindbergB., LonngrenJ. (1978) Assignment of absolute configuration of sugars by g.l.c. of their acetylated glycosides formed from chiral alcohols. Carbohydrate Research, 62, 359–362.
12.
WenkertE., BuckwalterB.L. (1972) Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes. Journal of the American Chemical Society, 94, 4367–4369.
13.
PolonskyJ., BaskevitchZ., Cagnolli-BellavitaN., CeccherelliP., BuckwalterB.L., WenkertE. (1972) Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XI. Biosynthesis of the virescenosides. Journal of the American Chemical Society, 94, 4369–4370.
14.
San FelicianoA., MedardeM., LopezJ.L., del CorralJ.M.M., PueblaP., BarreroA.F. (1988) Terpenoids from leaves of Juniperus thurifera. Phytochemistry, 27, 2241–2248.
15.
De KimpeN., SchampN., van PuyveldeL., DubeS., Chagnon-DubeM., BorremansF., van MeersscheM. (1982) Isolation and structural identification of 8(14),15-sandaracopimaradiene-7α,18-diol from Iboza riparia. Journal of Organic Chemistry, 47, 3628–3630.
16.
Cagnolli-BellavitaN., CeccherelliP., RibaldiM., PolonskyJ., BaskevitchZ. (1969) Virescenoside A e Virescenoside B: nuovi altrosidi metabolite dell'Oospora Virescens (Link) Wallr. Gazzetta Chimica Italiana, 99, 1354–1363.
17.
Cagnolli-BellavitaN., CeccherelliP., MarianiR., PolonskyJ., BaskevitchZ. (1970) Structure du virescenoside C, nouveau metabolite de Oospora virescens (Link) Wallr. European Journal of Biochemistry, 15, 356–359.
18.
CeccherelliP., Cagnolli-BellavitaN., PolonskyJ., BaskevitchZ. (1973) Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Lnk) Wallr. Tetrahedron, 29, 449–454.
