. 2017 Oct 31;9(11):353. doi: 10.3390/toxins9110353

Table 1.

Principal secondary metabolites produced by Aspergillus korhogoensis.

Metabolite	Elemental Composition	m/z	Ion	Retention Time (min)	MS/MS	Error (ppm)	ID Level *	References
AFLATOXIN BIOSYNTHESIS PATHWAY
Aflatoxin B₁	C₁₇H₁₂O₆	313.07	[M + H]⁺	17.37	285 (100), 298, 284, 270, 257, 243, 229	−0.398	1, 2	[25]
Aflatoxin B₂	C₁₇H₁₄O₆	315.07	[M + H]⁺	14.95	297, 287 (100), 259, 269, 273	−5.920	1, 2	[25]
Aflatoxin G₁	C₁₇H₁₂O₇	329.08	[M + H]⁺	15.25	311 (100), 301, 300, 283, 243	−0.119	1, 2	[25]
Aflatoxin G₂	C₁₇H₁₄O₇	331.08	[M + H]⁺	12.84	313 (100), 303, 285, 275, 257, 245	−0.511	1, 2	[25]
O-methyl-sterigmatocystin	C₁₉H₁₄O₆	339.08	[M + H]⁺	24.21	324 (100), 311, 306, 295	2.817	1
Sterigmatocystin	C₁₈H₁₂O₆	325.07	[M + H]⁺	33.59	310 (100), 297, 282	0.570	1, 2	[26]
Versicolorin A	C₁₈H₁₀O₇	337.03	[M − H]⁻	35.95	309 (100), 319, 308, 293, 265, 253	−2.094	1, 2	[27]
Versicolorin B	C₁₈H₁₂O₇	339.05	[M − H]⁻	34.40	311 (100) 310, 309, 295, 297, 283	−0.578	1, 2	[27]
Norsolorinic acid	C₂₀H₁₈O₇	369.10	[M − H]⁻	42.07	351 (100), 341, 325, 308, 297, 270	1.528	1
CYCLOPIAZONIC ACID BIOSYNTHETIC PATHWAY
α-cyclopiazonic acid	C₂₀H₂₀N₂O₃	337.15	[M + H]⁺	36.77	182 (100), 196, 154, 140	0.561	1, 2	[28]
β-cyclopiazonic acid	C₂₀H₂₂N₂O₃	339.17	[M + H]⁺	37.58	198 (100), 324, 283, 183, 144, 130	−1.289	2	[28]
2′-oxo-cyclopiazonic acid	C₂₀H₂₀N₂O₄	353.15	[M + H]⁺	36.20	335 (100), 311, 293, 252, 224, 212	−1.174	2	[28]
3′-hydroxy-speradine A	C₂₁H₂₂ N₂O₅	383.16	[M + H]⁺	21.19	355 (100), 365, 182, 184, 226, 254, 323, 347, 337	−1.144	2	[28]
Speradine C	C₂₀H₂₂ N₂O₅	371.16	[M + H]⁺	18.19	353 (100), 287, 269, 259, 226, 184	2.780	2	[28]
Speradine D	C₂₀H₂₂ N₂O₆	387.16	[M + H]⁺	20.80	369 (100), 269, 226, 184	2.679	2	[28]
Speradine F	C₂₁H₂₂ N₂O₇	415.15	[M + H]⁺	18.99	397 (100), 379, 369, 355, 353, 337, 311, 297, 281, 269, 253, 226, 184	−0.644	2	[28]
Cyclopiamide J	C₂₂H₂₄N₂O₇	429.17	[M + H]⁺	23.96	287 (100), 411, 497, 379, 369, 337, 269, 259, 226, 184	−0.693	2	[28]
KOJIC ACID BIOSYNTHETIC PATHWAY
Kojic acid	C₆H₆O₄	143.03	[M + H]⁺	1.87	143 (100) 125, 113, 97	1.432	1, 2	[29]
AFLATREM BIOSYNTHETIC PATHWAY
α-aflatrem	C₃₂H₃₉NO₄	502.29	[M + H]⁺	41.45	444 (100), 484, 426, 412, 376, 198	1.144
Paspalinine	C₂₇H₃₁NO₄	434.23	[M + H]⁺	39.22	376 (100), 416, 419, 362, 358, 344, 130	0.726	2	[30]
Paspaline	C₂₈H₃₉NO₂	422.31	[M + H]⁺	43.96	130 (100), 404, 407	−0.583	2	[30]
Hydroxyaflatrem	C₃₂H₃₉NO₅	518.29	[M + H]⁺	38.22	460 (100), 500, 482, 442, 446, 428	−0.347
Paxilline	C₂₇H₃₃NO₄	436.25	[M + H]⁺	38.64	418 (100), 421, 400, 378, 360, 346, 130	−2.762	1, 2	[30]
13′-desoxypaxilline	C₂₇H₃₃NO₃	420.25	[M + H]⁺	40.31	402 (100), 405, 362, 130	−0.320	2	[30]
ASPARASONE BIOSYNTHESIS PATHWAY
Asparasone A	C₁₈H₁₄O₈	357.06	[M − H]⁻	22.13	339 (100) 299	1.315	2	[31]
1,3,4,6,8 pentahydroxy-2-(1′-hydroxy-3′-oxobuty)anthraquinone	C₁₈H₁₄O₉	373.04	[M − H]⁻	9.36	355 (100) 315	0.629	2	[31]
1,3,6,8 tetrahydroxy-2-(1′-hydroxyethyl) anthraquinone	C₁₆H₁₂0₇	315.05	[M − H]⁻	27.98	297 (100)	0.775	2	[31]
1,3,6,8 tetrahydroxy-2-(3′ oxobut 1′-en-1′-yl) anthraquinone	C₁₈H₁₂0₇	339.05	[M − H]⁻	29.77	297 (100) 321, 296, 295, 311, 306	1.428	2	[31]
LEPORINS BIOSYNTHESIS PATHWAY
Leporin B	C₂₂H₂₅NO₃	352.19	[M + H]⁺	40.78	216 (100), 230, 244, 258, 270, 282, 296, 306	−1.505	2	[25]
Leporin B precursor	C₂₂H₂₅NO₂	336.20	[M + H]⁺	37.97	200 (100), 214, 228, 242, 254, 266, 280	0.102	2	[25]
AFLAVARIN BIOSYNTHESIS PATHWAY
Aflavarin	C₂₄H₂₂O₉	455.13	[M + H]⁺	18.22	413 (100), 425, 437, 395, 379, 364, 348, 303	−3.732	1, 2	[32]
7′-demethyl-siderin	C₁₁H₁₀O₄	207.07	[M + H]⁺	13.58	163 (100), 177, 175, 148, 147, 135, 133, 131, 115, 107	0.312	2	[32]
Aflavarin precursor 6	C₂₂H₁₈O₈	411.11	[M + H]⁺	20.69	369 (100), 381, 379, 352, 343, 337, 279, 207, 177, 147	−0.569	2	[32]
Aflavarin precursor 5	C₂₃H₂₀O₈	425.12	[M + H]⁺	26.75	383 (100), 393, 369, 363, 357, 349	0.484	2	[32]
Aflavarin precursor 4	C₂₄H₂₂O₈	439.14	[M + H]⁺	30.52	397 (100), 383, 371, 367, 365, 351, 341, 321	−0.624	2	[32]
AFLAVININE BIOSYNTHESIS PATHWAY
20′-hydroxyaflavinine	C₂₈H₃₉O₂N	404.29	[M − H₂O + H]⁺	37.53	386 (100), 287, 269, 243, 144, 130	0.071	1
Unknown aflavanine	C₂₈H₃₉O₂N	404.29	[M − H₂O + H]⁺	38.14	386 (100), 287, 269, 224	0.170

* ID Level 1: Metabolites that displayed the same retention time, UV and MS/MS spectra than the authentic standard. Level 2: Metabolites that displayed the same UV spectrum and/or the same MS/MS fragmentation pattern in accordance with the literature.