A new cyclonerol derivative from a marine-derived fungusAscotrichasp. ZJ-M-5

Abstract

A new sesquiterpene, ascotrichic acid (1), was isolated from a marine-derived fungus Ascotricha sp., together with the other two known analogues, cyclonerodiol (2) and 10(Z)-cyclonerotriol (3). Its structure was established by spectroscopic methods (1D and 2D NMR, HR-ESI-MS).

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

“…Compared to the rice culture control at the same culture condition, the HPLC finger-print of the EtOAc extract of the culture with sodium butyrate (10 µM) in rice medium showed new peaks at about 15, 31, and 38 min ( Figure 1A), and the main peaks of the harziane diterpenoids at 33-42 min ( Figure 1B) disappeared. Chemical investigation of the EtOAc extract led to the isolation of three new terpenoids, including one novel chlorinated cleistanthane diterpenoid, harzianolic acid A (1), one harziane diterpenoid, harzianone E (2), and one cyclonerane sesquiterpenoid, 3,7,11-trihydroxy-cycloneran (3), together with 11 known sesquiterpenoids, including eight cyclonerane sesquiterpenoids, methyl 3,7-dihydroxy-15cycloneranate (4) (Song et al, 2018), catenioblin C (5) (Wu et al, 2012), ascotrichic acid (6) (Xie et al, 2013), cyclonerotriol (7) (Kasitu et al, 1992), (10E)-12-acetoxy-10-cycloneren-3,7-diol (8) (Fang et al, 2018), cyclonerodiol (9) (Nozoe et al, 1970), cyclonerodiol oxide (10) (Fujita et al, 1984) and epicyclonerodiol oxide (11) (Fujita et al, 1984), one african sesquiterpenoid, ophioceric acid (12) (Reátegui et al, 2005), and two acoranetype sesqiuterpenoids, ent-trichoacorenol (13) (Brock and Dickschat, 2011) and trichoacorenol (14) (Huang et al, 1995) (Figure 2). These results revealed that the original main products harziane diterpenoids were replaced by cyclonerane sesquiterpenoids.…”

“…Mosher's method (Cao et al, 2014) was tried to determine the absolute configuration of C-7 but failed. Fortunately, a literature survey revealed that the coisolated cyclonerane-type compounds (4-9) and many other similar natural compounds have been reported the same absolute configurations as 2S,3R,6R,7R (Hanson et al, 1975;Kasitu et al, 1992;Li et al, 2007;Wu et al, 2012;Xie et al, 2013;Zhang et al, 2017;Fang et al, 2018;Song et al, 2018). Therefore, based on the biogenetic considerations, compound 3 was proposed to have the same absolute configuration (2S,3R,6R,7R) as the co-isolated compound 9, which was also supported by their similar OR between 3 ([α] 22 D -29.9 (c 1.00, CHCl 3 )) and 9 ([α] 22 D -26.6 (c 1.00, CHCl 3 ); lit.…”

“…Compounds 4-14 were identified to be methyl 3,7-dihydroxy-15-cycloneranate (Song et al, 2018), catenioblin C (Wu et al, 2012), ascotrichic acid (Xie et al, 2013), cyclonerotriol (Kasitu et al, 1992), (10E)-12-acetoxy-10-cycloneren-3,7-diol (Fang et al, 2018), cyclonerodiol (Nozoe et al, 1970), cyclonerodiol oxide (Fujita et al, 1984), epicyclonerodiol oxide (Fujita et al, 1984), ophioceric acid (Reátegui et al, 2005), ent-trichoacorenol (Brock and Dickschat, 2011), and trichoacorenol (Huang et al, 1995), respectively, by comparing their NMR data with those in the literature. The absolute configuration of 12 (1R,2S,4S) was confirmed for the first time using the method of single X-ray diffraction with the Flack's parameter of −0.05(5) (Figure 5).…”

A New Pimarane Diterpenoid from the Botryotinia fuckeliana Fungus Isolated from Deep‐Sea Water

“…On the basis of comparison of the NMR and specific rotation data with the literature, ten known compounds were identified to be (+)‐(7 S ,11 S )‐12‐hydroxysydonic acid ( 2 ), sydonic acid ( 3 ), hydroxysydonic acid ( 4 ), ascotrichic acid ( 5 ), trinorcyclonerodiol‐7,10‐lactone ( 6 ), 5 α ,8 α ‐epidioxyergosta‐6,22‐dien‐3 β ‐ol ( 7 ), cyclo‐( l ‐Leu‐ l ‐Trp) ( 8 ), cyclo‐( l ‐Trp‐Gly) ( 9 ), cyclo‐( l ‐Phe‐ l ‐Leu) ( 10 ), and cyclo‐( l ‐Leu‐ l ‐Tyr) ( 11 ) …”

Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus Trichothecium roseum and Their Biological Functions

“…Besides the above-mentioned three novel compounds (compounds 1, 8, and 9), three known trichomide cyclodepsipeptides were isolated from the PDB medium: destruxin A5 (compound 2) [11], trichomide A (compound 3) [11], and homodestruxin B (compound 4) [11]. Three typical destruxin cyclodepsipeptides, destruxin chlorohydrin (compound 5) [28], roseotoxin B (compound 6) [29], and C (compound 7) [30], and one cyclonerodiol sesquiterpene, ascotrichic acid (compound 10) [31] were isolated from the rice medium. The structures of these compounds were determined by detailed analyses of their spectroscopic data and comparisons with previously published reports.…”