111. Renner MK, Jensen PR, Fenical W (2000) Mangicols: structures and biosynthesis of a new
class of sesterterpene polyols from a marine fungus of the genus Fusarium. J Org Chem
65:4843
112. Renner MK, Jensen PR, Fenical W (1998) Neomangicols: structures and absolute stereochemistries of unprecedented halogenated sesterterpenes from a marine fungus of the genus
Fusarium. J Org Chem 63:8346
113. Fattorusso E, Magno S, Santacroce C, Sica D (1972) Scalarin, a new pentacyclic C-25
terpenoid from the sponge Cacospongia scalaris. Tetrahedron 28:5993
114. Cimino G, De Stefano S, Minale L, Trivellone E (1977) 12-epi-Scalarin and 12-epideoxoscalarin, sesterterpenes from the sponge Spongia nitens. J Chem Soc Perkin Trans 1:1587
115. Youssef DT, Yamaki RK, Kelly M, Scheuer PJ (2002) Salmahyrtisol A, a novel cytotoxic
sesterterpene from the Red Sea sponge Hyrtios erecta. J Nat Prod 65:2
116. Chang YC, Tseng SW, Liu LL, Chou Y, Ho YS, Lu MC, Su JH (2012) Cytotoxic
sesterterpenoids from a sponge Hippospongia sp. Mar Drugs 10:987
117. Wang JP, Yu J, Shu Y, Shi YX, Luo P, Cai L, Ding ZT (2018) Peniroquesines A–C:
sesterterpenoids possessing a 5/6/5/6/5-fused pentacyclic ring system from Penicillium
roqueforti YJ-14. Org Lett 20:5853
118. Huang X, Huang H, Li H, Sun X, Huang H, Lu Y, Lin Y, Long Y, She Z (2013)
Asperterpenoid A, a new sesterterpenoid as an inhibitor of Mycobacterium tuberculosis
protein tyrosine phosphatase B from the culture of Aspergillus sp. 16-5c. Org Lett 15:721
119. Liu Z, Chen Y, Chen S, Liu Y, Lu Y, Chen D, Lin Y, Huang X, She Z (2016) Aspterpenacids
A and B, two sesterterpenoids from a mangrove endophytic fungus Aspergillus terreus H010.
Org Lett 18:1406
120. Sadler IH, Simpson TJ (1989) The determination by n.m.r. methods of the structure and
stereochemistry of astellatol, a new and unusual sesterterpene. J Chem Soc Chem Commun
21:1602
121. Kaneda M, Takahashi R, Iitaka Y, Shibata S (1972) Retigeranic acid, a novel sesterterpene
isolated from the lichens of Lobaria retigera group. Tetrahedron Lett 13:4609
122. Rao PS, Sarma KG, Seshadri TR (1965) Chemical components of the Lobaria lichens from the
western Himalayas. Curr Sci 34:9
123. Millot M, Martin-de-Lassalle M, Chollet-Krugler M, Champavier Y, Mambu L, Chulia JA,
Lacaille-Dubois MA (2016) Two new retigerane-type sesterterpenoids from the lichen
Leprocaulon microscopicum. Helv Chim Acta 99:169
124. Sugawara H, Kasuya A, Iitaka Y, Shibata S (1991) Further studies on the structure of
retigeranic acid. Chem Pharm Bull 39:3051
125. Li Q, Chen C, Wei M, Dai C, Cheng L, Tao J, Li XN, Wang J, Sun W, Zhu H, Zhang Y (2019)
Niduterpenoids A and B: two sesterterpenoids with a highly congested hexacyclic 5/5/5/5/3/5
ring system from the fungus Aspergillus nidulans. Org Lett 21:2290
126. Mitsuhashi T, Abe I (2018) Chimeric terpene synthases possessing both terpene cyclization
and prenyltransfer activities. Chembiochem 19:1106
127. Minami A, Ozaki T, Liu C, Oikawa H (2018) Cyclopentane-forming di/sesterterpene
synthases: widely distributed enzymes in bacteria, fungi, and plants. Nat Prod Rep 35:1330
128. Okada M, Matsuda Y, Mitsuhashi T, Hoshino S, Mori T, Nakagawa K, Quan Z, Qin B,
Zhang H, Hayashi F, Kawaide H, Abe I (2016) Genome-based discovery of an unprecedented
cyclization mode in fungal sesterterpenoid biosynthesis. J Am Chem Soc 138:10011
129. Sato H, Mitsuhashi T, Yamazaki M, Abe I, Uchiyama M (2018) Computational studies on
biosynthetic carbocation rearrangements leading to quiannulatene: initial conformation regulates biosynthetic route, stereochemistry, and skeleton type. Angew Chem Int Ed 57:14752
130. Sato H, Mitsuhashi T, Yamazaki M, Abe I, Uchiyama M (2019) Inherent atomic mobility
changes in carbocation intermediates during the sesterterpene cyclization cascade. Beilstein J
Org Chem 15:1890
131. Huang AC, Kautsar SA, Hong YJ, Medema MH, Bond AD, Tantillo DJ, Osbourn A (2017)
Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining
reveals convergent evolution. Proc Natl Acad Sci U S A 114:E6005
76
T. Mitsuhashi and I. Abe
class of sesterterpene polyols from a marine fungus of the genus Fusarium. J Org Chem
65:4843
112. Renner MK, Jensen PR, Fenical W (1998) Neomangicols: structures and absolute stereochemistries of unprecedented halogenated sesterterpenes from a marine fungus of the genus
Fusarium. J Org Chem 63:8346
113. Fattorusso E, Magno S, Santacroce C, Sica D (1972) Scalarin, a new pentacyclic C-25
terpenoid from the sponge Cacospongia scalaris. Tetrahedron 28:5993
114. Cimino G, De Stefano S, Minale L, Trivellone E (1977) 12-epi-Scalarin and 12-epideoxoscalarin, sesterterpenes from the sponge Spongia nitens. J Chem Soc Perkin Trans 1:1587
115. Youssef DT, Yamaki RK, Kelly M, Scheuer PJ (2002) Salmahyrtisol A, a novel cytotoxic
sesterterpene from the Red Sea sponge Hyrtios erecta. J Nat Prod 65:2
116. Chang YC, Tseng SW, Liu LL, Chou Y, Ho YS, Lu MC, Su JH (2012) Cytotoxic
sesterterpenoids from a sponge Hippospongia sp. Mar Drugs 10:987
117. Wang JP, Yu J, Shu Y, Shi YX, Luo P, Cai L, Ding ZT (2018) Peniroquesines A–C:
sesterterpenoids possessing a 5/6/5/6/5-fused pentacyclic ring system from Penicillium
roqueforti YJ-14. Org Lett 20:5853
118. Huang X, Huang H, Li H, Sun X, Huang H, Lu Y, Lin Y, Long Y, She Z (2013)
Asperterpenoid A, a new sesterterpenoid as an inhibitor of Mycobacterium tuberculosis
protein tyrosine phosphatase B from the culture of Aspergillus sp. 16-5c. Org Lett 15:721
119. Liu Z, Chen Y, Chen S, Liu Y, Lu Y, Chen D, Lin Y, Huang X, She Z (2016) Aspterpenacids
A and B, two sesterterpenoids from a mangrove endophytic fungus Aspergillus terreus H010.
Org Lett 18:1406
120. Sadler IH, Simpson TJ (1989) The determination by n.m.r. methods of the structure and
stereochemistry of astellatol, a new and unusual sesterterpene. J Chem Soc Chem Commun
21:1602
121. Kaneda M, Takahashi R, Iitaka Y, Shibata S (1972) Retigeranic acid, a novel sesterterpene
isolated from the lichens of Lobaria retigera group. Tetrahedron Lett 13:4609
122. Rao PS, Sarma KG, Seshadri TR (1965) Chemical components of the Lobaria lichens from the
western Himalayas. Curr Sci 34:9
123. Millot M, Martin-de-Lassalle M, Chollet-Krugler M, Champavier Y, Mambu L, Chulia JA,
Lacaille-Dubois MA (2016) Two new retigerane-type sesterterpenoids from the lichen
Leprocaulon microscopicum. Helv Chim Acta 99:169
124. Sugawara H, Kasuya A, Iitaka Y, Shibata S (1991) Further studies on the structure of
retigeranic acid. Chem Pharm Bull 39:3051
125. Li Q, Chen C, Wei M, Dai C, Cheng L, Tao J, Li XN, Wang J, Sun W, Zhu H, Zhang Y (2019)
Niduterpenoids A and B: two sesterterpenoids with a highly congested hexacyclic 5/5/5/5/3/5
ring system from the fungus Aspergillus nidulans. Org Lett 21:2290
126. Mitsuhashi T, Abe I (2018) Chimeric terpene synthases possessing both terpene cyclization
and prenyltransfer activities. Chembiochem 19:1106
127. Minami A, Ozaki T, Liu C, Oikawa H (2018) Cyclopentane-forming di/sesterterpene
synthases: widely distributed enzymes in bacteria, fungi, and plants. Nat Prod Rep 35:1330
128. Okada M, Matsuda Y, Mitsuhashi T, Hoshino S, Mori T, Nakagawa K, Quan Z, Qin B,
Zhang H, Hayashi F, Kawaide H, Abe I (2016) Genome-based discovery of an unprecedented
cyclization mode in fungal sesterterpenoid biosynthesis. J Am Chem Soc 138:10011
129. Sato H, Mitsuhashi T, Yamazaki M, Abe I, Uchiyama M (2018) Computational studies on
biosynthetic carbocation rearrangements leading to quiannulatene: initial conformation regulates biosynthetic route, stereochemistry, and skeleton type. Angew Chem Int Ed 57:14752
130. Sato H, Mitsuhashi T, Yamazaki M, Abe I, Uchiyama M (2019) Inherent atomic mobility
changes in carbocation intermediates during the sesterterpene cyclization cascade. Beilstein J
Org Chem 15:1890
131. Huang AC, Kautsar SA, Hong YJ, Medema MH, Bond AD, Tantillo DJ, Osbourn A (2017)
Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining
reveals convergent evolution. Proc Natl Acad Sci U S A 114:E6005
76
T. Mitsuhashi and I. Abe