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. 2021 Jun 28;26(13):3959. doi: 10.3390/molecules26133959

Table 2.

List of secondary metabolites produced by Cladosporium species. The Latin suffix “bis” is added when the same name has been previously introduced for another compound. The names of novel compounds are underlined.

Code Name Formula Nominal Mass (U) Refs.
Alkaloids
1 Aspernigrin A C13H12N2O2 228 [47]
2 Aspidospermidin-20-ol, 1-acetyl-17-methoxy C22H30N2O3 370 [24]
3 Cladosin E C13H17NO4 251 [55]
4 Cladosporine A C28H39NO2 421 [84]
5 Cytochalasin D C30H37NO6 507 [85]
6 2-Methylacetate-3,5,6-trimethylpyrazine C10H14N2O2 194 [85]
7 Nonanal oxime C9H19NO 157 [17]
8 2-Piperidinone methyl C6H11NO 113 [17]
Azaphilones
9 Bicyclic diol C11H14O4 210 [52]
10 Lunatoic acid A C21H24O7 388 [49]
11 Perangustol A C11H14O4 210 [52]
12 Perangustol B C11H14O4 210 [52]
Benzofluoranthenones
13 (6bS,7R,8S)-4,9-Dihydroxy-7,8-
dimethoxy-1,6b,7,8-tetra-hydro-2H-
benzo[J]fluoranthen-3-one 		C23H22O4 362 [27]
14 (6bS,7R)-4,9-Dihydroxy-7-
methoxy-1,2,6b,7-tetrahydrobenzo[J]fluoranthen-3,8-dione 		C22H18O4 346 [27]
15 (6bR,7R,8S)-7-
Methoxy-4,8,9-trihydroxy-
1,6b,7,8-tetrahydro-2H-
benzo[J]fluoranthen-3-one 		C22H20O4 348 [27]
16 (6bS,7R,8S)-7-
Methoxy-4,8,9-trihydroxy-
1,6b,7,8-tetrahydro-2H-
benzo[J]fluoranthen-3-one 		C22H20O4 348 [27,28]
Benzopyranones
17 Coniochaetone A C13H10O4 230 [43]
18 Coniochaetone B C13H12O4 232 [43]
19 Coniochaetone K C13H10O6 262 [43]
Binaphthopyrones
20 Cladosporinone C33H30O14 650 [22]
21 Viriditoxin C34H30O14 662 [22]
22 Viriditoxin SC-28763 C34H30O13 646 [22]
23 Viriditoxin SC-30532 C34H30O12 630 [22]
Butenolides and butanolides
24 Cladospolide F C12H22O4 230 [94]
25 Cladospolide G C14H24O5 272 [32]
26 Cladospolide H C12H18O3 210 [32]
27 ent-Cladospolide F C12H22O4 230 [32]
28 11-Hydroxy-γ-dodecalactone C12H20O3 212 [94]
29 iso-Cladospolide B C12H20O4 228 [32,44,50,67,71,94]
Cinnamic acid derivatives
30 Chlorogenic acid C16H18O9 354 [70]
31 Caffeic acid C9H8O4 180 [70]
32 Coumaric acid C9H8O3 164 [70]
Citrinin derivatives
33 Citrinin H1 C25H30O7 442 [85]
34 Cladosporin A C13H15NO3 233 [92]
35 Cladosporin B C13H15NO3 233 [92]
36 Cladosporin C C14H16O4 248 [92]
37 Cladosporin D C12H16O4 224 [92]
Coumarins and Isocoumarins
38 Asperentin-8-methyl ether (= cladosporin-8-methyl ether) C17H22O6 322 [25]
39 Cladosporin (= asperentin) C16H20O5 292 [12,24,25,36,37]
40 5′-Hydroxyasperentin C16H20O6 308 [24,25]
41 7-Hydroxy-4-methoxy-5-methylcoumarin C11H10O4 206 [47]
42 Isocladosporin C16H20O5 292 [24,25,37]
43 Kotanin C24H22O8 438 [47]
44 Orlandin C22H18O8 410 [47]
45 Phomasatin C10H8O5 208 [35]
46 Umbelliferone C9H6O3 162 [70]
Cyclohexene derivatives
47 Cladoscyclitol A C12H20O5 244 [82]
48 Cladoscyclitol B C13H22O7 290 [82]
49 Cladoscyclitol C C12H22O4 230 [82]
50 Cladoscyclitol D C12H22O5 246 [82]
Despsides
51 3-Hydroxy-2,4,5-trimethylphenyl 2,4-dihydroxy-3,6-dimethylbenzoate C18H20O5 316 [69,98]
52 3-Hydroxy-2,4,5-trimethylphenyl 4-[(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,6-dimethylbenzoate C27H28O8 480 [69,98]
53 3-Hydroxy-2,5-dimethylphenyl 2,4-dihydroxy- 3,6-dimethylbenzoate C17H18O5 302 [69,98]
54 3-Hydroxy-2,5-dimethylphenyl 4-[(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,6-dimethylbenzoate C26H26O8 466 [69,98]
Diketopiperazines
55 (3R,8aR)-Cyclo(leucylprolyl) C11H18N2O2 210 [17]
56 (3S,8aS)-Cyclo(leucylprolyl) C11H18N2O2 210 [17]
57 (3R,8aR)-Cyclo(phenylalanylprolyl) C14H16N2O2 244 [17]
58 (3S,8aS)-Cyclo(phenylalanylprolyl) C14H16N2O2 244 [17]
Flavonoids
59 (2S)-7,4′-Dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone C21H22O5 354 [93]
60 Catechin C15H14O6 290 [70]
61 Epicatechin C15H14O6 290 [70]
Gibberelines
62 GA3 C19H22O6 346 [57]
63 GA4 C19H24O5 332 [57]
64 GA5 C19H22O5 330 [57]
65 GA7 C19H22O5 330 [57]
66 GA15 C20H26O4 330 [57]
67 GA19 C20H26O6 362 [57]
68 GA24 C20H26O5 346 [57]
Fusicoccane diterpene glycosides
69 Cotylenin A C33H50O11 622 [72,73,74]
70 Cotylenin B C33H51ClO11 659 [73,74]
71 Cotylenin C C33H52O11 624 [73]
72 Cotylenin D C33H52O12 640 [73]
73 Cotylenin E C28H46O9 526 [73]
Lactones
74 Cladosporactone A C10H12O4 196 [35]
75 Cladosporamide A C14H11NO5 273 [93]
76 5-Decanolide C10H18O2 170 [17]
77 Herbaric acid C10H8O6 224 [45]
78 Isochracinic acid C10H8O5 208 [35]
Macrolides
79 Brefeldin A C16H24O4 280 [77]
80 Cladocladosin A C13H18O3 222 [34]
81 Cladospamide A C13H20N2O4 268 [91]
82 Cladospolide A C12H20O4 228 [41,64,67,78,91]
83 Cladospolide B C12H20O4 228 [44,64,67,78]
84 Cladospolide C C12H20O4 228 [64]
85 4,5-Dihydroxy-12-methyloxacyclododecan-2-one C12H22O4 230 [67]
86 (6R,12S)-6-Hydroxy-12-methyl-
oxacyclodoecane-2,5-dione 		C12H20O4 228 [67]
87 (10S,12S)-10-Hydroxy-12-methyloxacyclododecane-2,5-dione C12H20O4 228 [67]
88 4-Hydroxy-12-methyloxacyclododecane-2,5,6-trione C12H18O5 242 [41]
89 (E)-(3R,6S)-6-Hydroxy-12-methyl-2,5-dioxooxacyclododecan-3-yl 4,11-dihydroxydodec-2-enoate C24H40O8 456 [78]
90 5R-Hydroxyrecifeiolide C12H20O3 212 [32]
91 5S-Hydroxyrecifeiolide C12H20O3 212 [32]
92 12-Methyloxacyclododecane-2,5,6-trione C12H18O4 226 [41]
93 Methyl 2-(((4R,6S,12R)-6-hydroxy-12-methyl-2,5-dioxooxacyclododecan-4-yl)thio)acetate C15H24O6S 332 [78]
94 5Z-7-Oxozeaenol C19H22O7 362 [49]
95 Pandangolide 1 C12H20O5 244 [32,41,48,71,78]
96 Pandangolide 1a C12H20O5 244 [71,78]
97 Pandangolide 2 C14H22O6S 318 [44,78]
98 Pandangolide 3 C16H26O7S 362 [33,44,50,78]
99 Pandangolide 4 C24H38O8S 486 [44]
100 Patulolide B C13H20O3 224 [41]
101 Sporiolide A C19H24O6 348 [88]
102 Sporiolide B C14H24O4 256 [88]
103 Thiocladospolide A C16H26O6S 346 [33,50]
104 Thiocladospolide B C16H24O7S 360 [33]
105 Thiocladospolide C C15H22O6S 330 [33]
106 Thiocladospolide D C16H28O7S 364 [33]
107 Thiocladospolide E C14H26O5S 306 [91]
108 Thiocladospolide F C16H28O5S 332 [34]
109 Thiocladospolide F bis C24H38O8S 486 [50]
110 Thiocladospolide G C16H28O6S 348 [34]
111 Thiocladospolide G bis C15H24O7S 348 [50]
112 Thiocladospolide H C15H24O6S 332 [50]
113 Thiocladospolide I C27H44O10S 560 [50]
114 Thiocladospolide J C27H42O10S 558 [50]
115 Zeaenol C19H24O7 364 [49]
Naphthalene derivatives
116 Cladonaphchrom A C22H22O4 350 [83]
117 Cladonaphchrom B C22H22O4 350 [83]
118 1,8-Dimethoxynaphthalene C12H12O2 188 [81,83]
119 8-Methoxynaphthalen-1-ol C11H10O2 174 [83]
Naphtalenones
120 Altertoxin XII C20H18O4 322 [87]
121 Cladosporol A C20H16O6 352 [26,66,86]
122 Cladosporol B C20H14O6 350 [66]
123 Cladosporol C C20H18O5 338 [35,39,40,66,85,86]
124 Cladosporol D C20H18O6 354 [66,86]
125 Cladosporol E C20H18O7 370 [40,66,85]
126 Cladosporol F C21H20O5 352 [39,40]
127 Cladosporol G C20H17ClO6 388 [40]
128 Cladosporol G bis C21H20O5 352 [39]
129 Cladosporol H C20H16O5 336 [39]
130 Cladosporol I C20H18O5 338 [39,92]
131 Cladosporol J C20H18O5 338 [39]
132 Cladosporone A C20H16O6 352 [86]
133 Clindanone A C22H18O7 394 [40]
134 Clindanone B C22H18O7 394 [40]
135 (3R,4R)-3,4-Dihydro-3,4,8-trihydroxy-1(2H)-napthalenone C10H10O4 194 [81]
136 4,8-Dihydroxy-1-tetralone C10H10O3 178 [52]
137 (3S)-3,8-Dihydroxy-6,7-dimethyl-α-tetralone C12H14O3 206 [81]
138 Isosclerone C10H10O3 178 [40]
139 Scytalone C10H10O4 194 [68]
140 (−)-(4R)-Regiolone C10H10O3 178 [81]
141 (−)-trans-(3R,4R)-3,4,8-Trihydroxy-6,7-dimethyl-3,4- dihydronaphtha- len-1(2H)-one C12H14O4 222 [81]
Naphthoquinones and anthraquinones
142 Anhydrofusarubin C15H12O6 288 [90]
143 Methyl ether of fusarubin C16H16O7 320 [90]
144 Plumbagin C11H8O3 188 [42]
Perylenequinones
145 Altertoxin VIII C20H16O3 304 [87]
146 Altertoxin IX C20H18O2 290 [87]
147 Aterotoxin X C20H18O2 290 [87]
148 Altertoxin XI C21H20O2 304 [87]
149 Calphostin A (= UCN-1028A) C44H38O12 758 [29,30]
150 Calphostin B C37H34O11 654 [30]
151 Calphostin C (= Cladochrome E) C44H38O14 790 [30,31]
152 Calphostin D (= ent-isophleinchrome) C30H30O10 550 [30,46]
153 Calphostin I (= Cladochrome D) C44H38O15 806 [30,31]
154 Phleichrome C30H30O10 550 [53,54,99]
Pyrones
155 Citreoviridin A C23H30O6 402 [45]
156 Herbarin A C12H12O5 236 [45]
157 Herbarin B C10H10O5 210 [45]
158 5-Hydroxy-2-oxo-2H-piran-4-yl) methyl acetate C8H8O5 184 [65]
Seco acids
159 Cladospolide E C12H20O4 228 [94]
160 11-Hydroxy-4,5-dioxododecanoic acid C12H20O5 244 [78]
161 seco-Patulolide A C12H20O4 228 [94]
162 seco-Patulolide C C12H22O4 230 [33,41,50,94]
163 (3S,5S, 11S)-Trihydroxydodecanoic acid C12H24O5 248 [68]
Sterols
164 Cladosporide A C25H40O3 388 [79]
165 Cladosporide B C25H38O3 386 [80]
166 Cladosporide C C25H40O3 388 [80]
167 Cladosporide D C25H38O3 386 [80]
168 Cladosporisteroid B C21H30O3 330 [35]
169 (22E,24R)-3β,5α-Dihydroxyergosta-7,22-dien-6-one C28H44O3 428 [35]
170 Ergosterol C28H44O 396 [79]
171 3α-Hydroxy-pregn-7-ene-6,20-dione C21H30O3 330 [62]
172 23,24,25,26,27-Pentanorlanost-8-ene-3β,22-diol C28H42O5 458 [79]
173 Peroxyergosterol (= (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol) C28H44O3 428 [23,35,79]
174 3β,5α,6β-Trihydroxyergosta-7,22-diene C29H48O3 444 [47]
175 3β,5α,9α-Trihydroxy-
(22E,24R)-ergosta-6-one		 C28H44O4 444 [35]
Tetramic acids
176 Cladodionen C13H15NO3 233 [58,63,89,96]
177 Cladosin A C13H20N2O4 268 [55]
178 Cladosin B C12H18N2O4 254 [55,60,63]
179 Cladosin C C12H16N2O3 236 [55,60,63]
180 Cladosin D C13H18N2O3 250 [55]
181 Cladosin F C12H18N2O4 254 [56,60,63]
182 Cladosin G C13H20N2O4 268 [56]
183 Cladosin H C20H26N2O4 358 [89]
184 Cladosin I C20H26N2O4 358 [89]
185 Cladosin J C25H29N3O3 419 [89]
186 Cladosin K C25H29N3O3 419 [89]
187 Cladosin L C13H22N2O4 270 [60]
188 Cladosin L bis C14H13NO3 243 [63]
189 Cladosin M C13H17NO4 251 [63]
190 Cladosin N C13H17NO4 251 [63]
191 Cladosin O C9H12N2O 164 [63]
192 Cladosporicin A C21H27N3O5 401 [61]
193 Cladosporiumin A C19H27NO5 349 [59]
194 Cladosporiumin B C19H27NO5 349 [59]
195 Cladosporiumin C C19H27NO5 349 [59]
196 Cladosporiumin D C14H21NO3 251 [59]
197 Cladosporiumin E C13H17NO4 251 [58,59]
198 Cladosporiumin F C13H19NO5 269 [59]
199 Cladosporiumin G C13H19NO4 253 [58,59]
200 Cladosporiumin H C14H23NO5 285 [59]
201 Cladosporiumin I C13H19NO3 237 [58]
202 Cladosporiumin I bis C19H27NO5 349 [61]
203 Cladosporiumin J C13H17NO4 251 [58]
204 Cladosporiumin J bis C19H27NO5 349 [61]
205 Cladosporiumin K C13H17NO4 251 [58]
206 Cladosporiumin L (C13H20NO5)3Mg2 889 [58]
207 Cladosporiumin M C13H15NO3 233 [58]
208 Cladosporiumin N C13H19NO4 253 [58]
209 Cladosporiumin O C13H17NO4 251 [58]
Tropolones
210 Malettinin A C16H16O5 288 [95]
211 Malettinin B C16H20O5 292 [95]
212 Malettinin C C16H20O5 292 [95]
213 Malettinin E C16H20O5 292 [95]
Volatile terpenes
214 (−)-trans-Caryophyllene C15H24 204 [38]
215 Dehydro aromdendrene C15H22 202 [38]
216 α-Pinene C10H16 136 [38]
217 (+)-Sativene C15H24 204 [38]
Xanthones
218 Conioxanthone A C16H12O7 316 [43]
219 3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate C16H12O6 300 [43]
220 α-Diversonolic ester C16H16O7 320 [43]
221 β-Diversonolic ester C16H16O7 320 [43]
222 8-Hydroxy-6-methylxanthone-1-carboxylic acid C15H12O5 272 [43]
223 Methyl 8-hydroxy-6-(hydroxymethyl)- 9-oxo-9H-xanthene-1-carboxylate C16H12O6 300 [43]
224 Methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1- carboxylate C16H12O5 284 [43]
225 8-(Methoxycarbonyl)-1-hydroxy-9-oxo-9H-xanthene-3-carboxylic acid C16H10O7 314 [43]
226 Secalonic acid D C32H30O14 638 [85]
227 Vertixanthone C15H10O5 270 [43]
Miscellaneous
228 α-Acetylorcinol C9H10O3 166 [52]
229 Acetyl Sumiki’s acid C9H10O4 182 [44]
230 Cladosacid C15H22O3 250 [96]
231 (2R*,4R*)-3,4-dihydro-5-methoxy-2-methyl-1(2H)-benzopyran-4-ol C10H12O2 164 [81]
232 1-(3,5-Dihydroxy-4-methylphenyl)propan-2-one C10H12O3 180 [52]
233 1,1′-Dioxine-2,2′-dipropionic acid C10H12O6 228 [85]
234 Ellagic acid C14H6O8 302 [70]
235 Fonsecinone A C32H26O10 570 [47]
236 5-Hydroxy-2-methyl-4H-chromen-4-one C10H8O3 176 [83]
237 (2S)-5-Hydroxy-2-methyl-chroman-4-one C10H10O2 162 [81,83]
238 4-O-α -d-Ribofuranose-2-pentyl-3-phemethylol C17H26O6 326 [82]
239 4-O-α-d-Ribofuranose-3-hydroxymethyl-2-pentylphenol C17H26O7 342 [81]
240 Rubrofusarin B C16H14O5 286 [47]
241 Sumiki’s acid C6H6O4 142 [44]
242 Taxol C47H51NO14 853 [51]
243 tert-Butylhydroquinone C10H14O2 166 [70]
244 Vermistatin C18H16O6 328 [85]