48. Ikeda Y, Aoki M, Uyehara T, Kato T, Yokoyama T (1983) Synthesis of dl-(2E,6Z,10E)cericerene for elucidation of the proposed structure of cericerol-I. Chem Lett 12:1073
49. Fujiwara S, Aoki M, Uyehara T, Kato T (1984) Confirmation of the structure of ceriperol and
its related sesterterpenes by the total synthesis. Tetrahedron Lett 25:3003
50. Forestieri R, Merchant CE, de Voogd NJ, Matainaho T, Kieffer TJ, Andersen RJ (2009)
Alotaketals A and B, sesterterpenoids from the marine sponge Hamigera species that activate
the cAMP cell signaling pathway. Org Lett 11:5166
51. Kirsch G, König GM, Wright AD, Kaminsky R (2000) A new bioactive sesterterpene and
antiplasmodial alkaloids from the marine sponge Hyrtios cf. erecta. J Nat Prod 63:825
52. Tsuda M, Endo T, Mikami Y, Fromont J, Kobayashi J (2002) Luffariolides H and J, new
sesterterpenes from a marine sponge Luffariella species. J Nat Prod 65:1507
53. Elkhayat E, Edrada R, Ebel R, Wray V, Soest RV, Wiryowidagdo S, Mohamed MH, Müller
WEG, Proksch P (2004) New luffariellolide derivatives from the Indonesian sponge
Acanthodendrilla sp. J Nat Prod 67:1809
54. D’Acquisto F, Lanzotti V, Carnuccio R (2000) Cyclolinteinone, a sesterterpene from sponge
Cacospongia linteiformis, prevents inducible nitric oxide synthase and inducible cyclooxygenase protein expression by blocking nuclear factor-κB activation in J774 macrophages.
Biochem J 346:793
55. Carotenuto A, Fattorusso E, Lanzotti V, Magno S, Carnuccio R, Acquisto FD (1997) Structure
and absolute stereochemistry of the new cyclolinteinol and cyclolinteinol acetate, macrophage
activation modulators. Tetrahedron 53:7305
56. Ettinger-Epstein P, Motti CA, de Nys R, Wright AD, Battershill CN, Tapiolas DM (2007)
Acetylated sesterterpenes from the great barrier reef sponge Luffariella variabilis. J Nat Prod
70:648
57. Oka M, Iimura S, Narita Y, Furumai T, Konishi M, Oki T, Gao Q, Kakisawa H (1993)
Stereochemistry and biosynthesis of terpestacin, a new syncytium formation inhibitor. J Org
Chem 58:1875
58. Lin T, Lin X, Lu C, Hu Z, Huang W, Huang Y, Shen Y (2009) Secondary metabolites of
Phomopsis sp. XZ-26, an endophytic fungus from Camptotheca acuminata. Eur J Org Chem
2009:2975
59. Jung HJ, Shim JS, Lee J, Song YM, Park KC, Choi SH, Kim ND, Yoon JH, Mungai PT,
Schumacker PT, Kwon HJ (2010) Terpestacin inhibits tumor angiogenesis by targeting
UQCRB of mitochondrial complex III and suppressing hypoxia-induced reactive oxygen
species production and cellular oxygen sensing. J Biol Chem 285:11584
60. Nihashi Y, Lim CH, Tanaka C, Miyagawa H, Ueno T (2002) Phytotoxic sesterterpene,
11-epiterpestacin, from Bipolaris sorokiniana NSDR-011. Biosci Biotechnol Biochem 66:685
61. Chan J, Jamison TF (2004) Enantioselective synthesis of (-)-terpestacin and structural revision
of siccanol using catalytic stereoselective fragment couplings and macrocyclizations. J Am
Chem Soc 126:10682
62. Santini A, Ritieni A, Fogliano V, Randazzo G, Mannina L, Logrieco A, Benedetti E (1996)
Structure and absolute stereochemistry of fusaproliferin, a toxic metabolite from Fusarium
proliferatum. J Nat Prod 59:109
63. Myers AG, Siu M, Ren F (2002) Enantioselective synthesis of (–)-terpestacin and (–)fusaproliferin: clarification of optical rotational measurements and absolute configurational
assignments establishes a homochiral structural series. J Am Chem Soc 124:4230
64. Xu YM, Espinosa-Artiles P, Liu MX, Arnold AE, Gunatilaka AA (2013) Secoemestrin D, a
cytotoxic epitetrathiodioxopiperizine, and emericellenes A–E, five sesterterpenoids from
Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus. J Nat Prod 76:2330
65. Moghaddam FM, Amiri R, Alam M, Hossain MB, van der Helm D (1998) Structure and
absolute stereochemistry of salvimirzacolide, a new sesterterpene from Salvia mirzayanii. J
Nat Prod 61:279
66. Linden A, Juch M, Moghaddam FM, Zaynizadeh B, Rüedi P (1996) The absolute configuration of salvileucolide methyl ester, a sesterterpene from Iranian Salvia species. Phytochemistry
41:589
Sesterterpenoids
73
49. Fujiwara S, Aoki M, Uyehara T, Kato T (1984) Confirmation of the structure of ceriperol and
its related sesterterpenes by the total synthesis. Tetrahedron Lett 25:3003
50. Forestieri R, Merchant CE, de Voogd NJ, Matainaho T, Kieffer TJ, Andersen RJ (2009)
Alotaketals A and B, sesterterpenoids from the marine sponge Hamigera species that activate
the cAMP cell signaling pathway. Org Lett 11:5166
51. Kirsch G, König GM, Wright AD, Kaminsky R (2000) A new bioactive sesterterpene and
antiplasmodial alkaloids from the marine sponge Hyrtios cf. erecta. J Nat Prod 63:825
52. Tsuda M, Endo T, Mikami Y, Fromont J, Kobayashi J (2002) Luffariolides H and J, new
sesterterpenes from a marine sponge Luffariella species. J Nat Prod 65:1507
53. Elkhayat E, Edrada R, Ebel R, Wray V, Soest RV, Wiryowidagdo S, Mohamed MH, Müller
WEG, Proksch P (2004) New luffariellolide derivatives from the Indonesian sponge
Acanthodendrilla sp. J Nat Prod 67:1809
54. D’Acquisto F, Lanzotti V, Carnuccio R (2000) Cyclolinteinone, a sesterterpene from sponge
Cacospongia linteiformis, prevents inducible nitric oxide synthase and inducible cyclooxygenase protein expression by blocking nuclear factor-κB activation in J774 macrophages.
Biochem J 346:793
55. Carotenuto A, Fattorusso E, Lanzotti V, Magno S, Carnuccio R, Acquisto FD (1997) Structure
and absolute stereochemistry of the new cyclolinteinol and cyclolinteinol acetate, macrophage
activation modulators. Tetrahedron 53:7305
56. Ettinger-Epstein P, Motti CA, de Nys R, Wright AD, Battershill CN, Tapiolas DM (2007)
Acetylated sesterterpenes from the great barrier reef sponge Luffariella variabilis. J Nat Prod
70:648
57. Oka M, Iimura S, Narita Y, Furumai T, Konishi M, Oki T, Gao Q, Kakisawa H (1993)
Stereochemistry and biosynthesis of terpestacin, a new syncytium formation inhibitor. J Org
Chem 58:1875
58. Lin T, Lin X, Lu C, Hu Z, Huang W, Huang Y, Shen Y (2009) Secondary metabolites of
Phomopsis sp. XZ-26, an endophytic fungus from Camptotheca acuminata. Eur J Org Chem
2009:2975
59. Jung HJ, Shim JS, Lee J, Song YM, Park KC, Choi SH, Kim ND, Yoon JH, Mungai PT,
Schumacker PT, Kwon HJ (2010) Terpestacin inhibits tumor angiogenesis by targeting
UQCRB of mitochondrial complex III and suppressing hypoxia-induced reactive oxygen
species production and cellular oxygen sensing. J Biol Chem 285:11584
60. Nihashi Y, Lim CH, Tanaka C, Miyagawa H, Ueno T (2002) Phytotoxic sesterterpene,
11-epiterpestacin, from Bipolaris sorokiniana NSDR-011. Biosci Biotechnol Biochem 66:685
61. Chan J, Jamison TF (2004) Enantioselective synthesis of (-)-terpestacin and structural revision
of siccanol using catalytic stereoselective fragment couplings and macrocyclizations. J Am
Chem Soc 126:10682
62. Santini A, Ritieni A, Fogliano V, Randazzo G, Mannina L, Logrieco A, Benedetti E (1996)
Structure and absolute stereochemistry of fusaproliferin, a toxic metabolite from Fusarium
proliferatum. J Nat Prod 59:109
63. Myers AG, Siu M, Ren F (2002) Enantioselective synthesis of (–)-terpestacin and (–)fusaproliferin: clarification of optical rotational measurements and absolute configurational
assignments establishes a homochiral structural series. J Am Chem Soc 124:4230
64. Xu YM, Espinosa-Artiles P, Liu MX, Arnold AE, Gunatilaka AA (2013) Secoemestrin D, a
cytotoxic epitetrathiodioxopiperizine, and emericellenes A–E, five sesterterpenoids from
Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus. J Nat Prod 76:2330
65. Moghaddam FM, Amiri R, Alam M, Hossain MB, van der Helm D (1998) Structure and
absolute stereochemistry of salvimirzacolide, a new sesterterpene from Salvia mirzayanii. J
Nat Prod 61:279
66. Linden A, Juch M, Moghaddam FM, Zaynizadeh B, Rüedi P (1996) The absolute configuration of salvileucolide methyl ester, a sesterterpene from Iranian Salvia species. Phytochemistry
41:589
Sesterterpenoids
73