67. Müller EL, Faulkner DJ (1997) Absolute configuration of halisulfate 3 from the sponge Ircinia
sp. Tetrahedron 53:5373
68. Charan RD, McKee TC, Boyd MR (2001) Thorectandrols A and B, new cytotoxic
sesterterpenes from the marine sponge Thorectandra species. J Nat Prod 64:661
69. Gregson RP, Ouvrier D (1982) Wistarin, a tetracyclic furanosesterterpene from the marine
sponge Ircinia wistarii. J Nat Prod 45:412
70. Uenishi J, Kawahama R, Yonemitsu O (1997) Total synthesis of (À)-ircinianin and (+)wistarin. J Org Chem 62:1691
71. Fontana A, Fakhr I, Mollo E, Cimino G (1999) (À)-Wistarin from the marine sponge Ircinia
sp.: the first case of enantiomeric sesterterpenes. Tetrahedron Asymmetr 10:3869
72. Coll JC, Kearns PS, Rideout JA, Hooper J (1997) Ircinianin sulfate from the marine sponge
Ircinia (Psammocinia) wistarii. J Nat Prod 60:1178
73. Nozoe S, Morisaki M, Tsuda K, Iitaka Y, Takahashi N, Tamura S, Ishibashi K, Shirasaka M
(1965) The structure of ophiobolin, a C 25 terpenoid having a novel skeleton. J Am Chem Soc
87:4968
74. Canonica L, Fiecchi A, Kienle MG, Scala A (1966) The constitution of cochliobolin. Tetrahedron Lett 7:1211
75. Tsuda K, Nozoe S, Morisaki M, Hirai K, Itai A, Okuda S, Canonica L, Fiecchi A, Kienle MG,
Scala A (1967) Nomenclature of ophiobolins. Tetrahedron Lett 8:3369
76. Canonica L, Friecchi A, Kienle UG, Scala A (1966) Isolation and constitution of cochliobolin
b. Tetrahedron Lett 7:1329
77. Nozoe S, Hirai K, Tsuda K (1966) The structure of zizannin-A and -B, C 25 -terpenoids isolated
from Helminthosporium zizaniae. Tetrahedron Lett 7:2211
78. Itai A, Nozoe S, Tsuda K, Okuda S, Iitaka Y (1967) The structure of cephalonic acid, a
pentaprenyl terpenoid. Tetrahedron Lett 42:4111
79. Nozoe S, Itai A, Tsuda K, Okuda S (1967) The chemical transformation of cephalonic acid.
Tetrahedron Lett 42:4113
80. Cutler HG, Crumley FG, Cox RH, Springer JP, Arrendale RF, Cole RJ, Cole PD (1984)
Ophiobolins G and H: new fungal metabolites from a novel source, Aspergillus ustus. J Agric
Food Chem 32:778
81. Sugawara F, Strobel G, Strange RN, Siedow JN, Van Duyne GD, Clardy J (1987) Phytotoxins
from the pathogenic fungi Drechslera maydis and Drechslera sorghicola. Proc Natl Acad Sci
U S A 84:3081
82. Sugawara F, Takahashi N, Strobel G, Yun CH, George G, Fu Y, Clardy J (1988) Some new
phytotoxic ophiobolins produced by Drechslera oryzae. J Org Chem 53:2170
83. Singh SB, Smith JL, Sabnis GS, Dombrowski AW, Schaeffer JM, Goetz MA, Bills GF (1991)
Structure and conformation of ophiobolin K and 6-epiophiobolin K from Aspergillus ustus as a
nematocidal agent. Tetrahedron 47:6931
84. Li E, Clark AM, Rotella DP, Hufford CD (1995) Microbial metabolites of ophiobolin A and
antimicrobial evaluation of ophiobolins. J Nat Prod 58:74
85. Tsipouras A, Adefarati AA, Tkacz JS, Frazier EG, Rohrer SP, Birzin E, Rosegay A, Zink DL,
Goetz MA, Singh SB, Schaeffer JM (1996) Ophiobolin M and analogues, noncompetitive
inhibitors of ivermectin binding with nematocidal activity. Bioorg Med Chem 4:531
86. Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R, Motta A (2006)
Ophiobolin E and 8-epi-ophiobolin J produced by Drechslera gigantea, a potential
mycoherbicide of weedy grasses. Phytochemistry 67:2281
87. Bladt TT, Dürr C, Knudsen PB, Kildgaard S, Frisvad JC, Gotfredsen CH, Seiffert M, Larsen
TO (2013) Bio-activity and dereplication-based discovery of ophiobolins and other fungal
secondary metabolites targeting leukemia cells. Molecules 18:14629
88. Kim JM, Hyeon SB, Isogai A, Suzuki A (1984) Isolation of ophiobolin A and its analogs as
inhibitors to photosynthesis. Agric Biol Chem 48:803
89. Canales MW, Gray GR (1988) 6-Epiophiobolin A and 3-anhydro-6-epiophiobolin A — host
specific phytotoxins of Drechslera maydis (race T). Phytochemistry 27:1653
74
T. Mitsuhashi and I. Abe
sp. Tetrahedron 53:5373
68. Charan RD, McKee TC, Boyd MR (2001) Thorectandrols A and B, new cytotoxic
sesterterpenes from the marine sponge Thorectandra species. J Nat Prod 64:661
69. Gregson RP, Ouvrier D (1982) Wistarin, a tetracyclic furanosesterterpene from the marine
sponge Ircinia wistarii. J Nat Prod 45:412
70. Uenishi J, Kawahama R, Yonemitsu O (1997) Total synthesis of (À)-ircinianin and (+)wistarin. J Org Chem 62:1691
71. Fontana A, Fakhr I, Mollo E, Cimino G (1999) (À)-Wistarin from the marine sponge Ircinia
sp.: the first case of enantiomeric sesterterpenes. Tetrahedron Asymmetr 10:3869
72. Coll JC, Kearns PS, Rideout JA, Hooper J (1997) Ircinianin sulfate from the marine sponge
Ircinia (Psammocinia) wistarii. J Nat Prod 60:1178
73. Nozoe S, Morisaki M, Tsuda K, Iitaka Y, Takahashi N, Tamura S, Ishibashi K, Shirasaka M
(1965) The structure of ophiobolin, a C 25 terpenoid having a novel skeleton. J Am Chem Soc
87:4968
74. Canonica L, Fiecchi A, Kienle MG, Scala A (1966) The constitution of cochliobolin. Tetrahedron Lett 7:1211
75. Tsuda K, Nozoe S, Morisaki M, Hirai K, Itai A, Okuda S, Canonica L, Fiecchi A, Kienle MG,
Scala A (1967) Nomenclature of ophiobolins. Tetrahedron Lett 8:3369
76. Canonica L, Friecchi A, Kienle UG, Scala A (1966) Isolation and constitution of cochliobolin
b. Tetrahedron Lett 7:1329
77. Nozoe S, Hirai K, Tsuda K (1966) The structure of zizannin-A and -B, C 25 -terpenoids isolated
from Helminthosporium zizaniae. Tetrahedron Lett 7:2211
78. Itai A, Nozoe S, Tsuda K, Okuda S, Iitaka Y (1967) The structure of cephalonic acid, a
pentaprenyl terpenoid. Tetrahedron Lett 42:4111
79. Nozoe S, Itai A, Tsuda K, Okuda S (1967) The chemical transformation of cephalonic acid.
Tetrahedron Lett 42:4113
80. Cutler HG, Crumley FG, Cox RH, Springer JP, Arrendale RF, Cole RJ, Cole PD (1984)
Ophiobolins G and H: new fungal metabolites from a novel source, Aspergillus ustus. J Agric
Food Chem 32:778
81. Sugawara F, Strobel G, Strange RN, Siedow JN, Van Duyne GD, Clardy J (1987) Phytotoxins
from the pathogenic fungi Drechslera maydis and Drechslera sorghicola. Proc Natl Acad Sci
U S A 84:3081
82. Sugawara F, Takahashi N, Strobel G, Yun CH, George G, Fu Y, Clardy J (1988) Some new
phytotoxic ophiobolins produced by Drechslera oryzae. J Org Chem 53:2170
83. Singh SB, Smith JL, Sabnis GS, Dombrowski AW, Schaeffer JM, Goetz MA, Bills GF (1991)
Structure and conformation of ophiobolin K and 6-epiophiobolin K from Aspergillus ustus as a
nematocidal agent. Tetrahedron 47:6931
84. Li E, Clark AM, Rotella DP, Hufford CD (1995) Microbial metabolites of ophiobolin A and
antimicrobial evaluation of ophiobolins. J Nat Prod 58:74
85. Tsipouras A, Adefarati AA, Tkacz JS, Frazier EG, Rohrer SP, Birzin E, Rosegay A, Zink DL,
Goetz MA, Singh SB, Schaeffer JM (1996) Ophiobolin M and analogues, noncompetitive
inhibitors of ivermectin binding with nematocidal activity. Bioorg Med Chem 4:531
86. Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R, Motta A (2006)
Ophiobolin E and 8-epi-ophiobolin J produced by Drechslera gigantea, a potential
mycoherbicide of weedy grasses. Phytochemistry 67:2281
87. Bladt TT, Dürr C, Knudsen PB, Kildgaard S, Frisvad JC, Gotfredsen CH, Seiffert M, Larsen
TO (2013) Bio-activity and dereplication-based discovery of ophiobolins and other fungal
secondary metabolites targeting leukemia cells. Molecules 18:14629
88. Kim JM, Hyeon SB, Isogai A, Suzuki A (1984) Isolation of ophiobolin A and its analogs as
inhibitors to photosynthesis. Agric Biol Chem 48:803
89. Canales MW, Gray GR (1988) 6-Epiophiobolin A and 3-anhydro-6-epiophiobolin A — host
specific phytotoxins of Drechslera maydis (race T). Phytochemistry 27:1653
74
T. Mitsuhashi and I. Abe