Table 3.
Metabolites of AC, MA, and HA converted in intestine.
| DDAs | m/z (ESI+) | Formula | Identification | Neutral loss (Da), identification of fatty acid | Metabolic procedure | MS detection | References |
|---|---|---|---|---|---|---|---|
| AC | 662 | C34H47NO12 | 10-Hydroxy AC | NAa | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P4) |
| 632 | C33H45NO11 | 16-O-Demethyl AC* | NA | Rabbits; contents from small intestine and caecum and feces; ig, in vivo. | IT | [23] (M3) | |
| Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] (M1) | |||||
| 630 | C34H47NO10 | Indaconitine (15-deoxy AC)b | Rabbits; contents from small intestine and caecum and feces; ig, in vivo. | IT | [23] (M6) | ||
| Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P5) | |||||
| Deoxy AC* | NA | Rabbits; contents from small intestine and caecum and feces; ig, in vivo. | IT | [23] (M5) | |||
| Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] (M2) | |||||
| Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P10) | |||||
| 616 | C33H45NO10 | 16-O-Demethyl-deoxy AC* | NA | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] (M3) | |
| 604 | C32H45NO10 | BAC | NA | Rabbits; contents from small intestine and caecum and feces; ig, in vivo. | IT | [23] (M2) | |
| Rats; intestinal bacteria; anaerobic incubation, in vitro.c | IT | [25] | |||||
| Rats; intestinal bacteria; anaerobic incubation, in vitro.d | IT | [26] | |||||
| Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P1) | |||||
| 590 | C31H43NO10 | 16-O-Demethyl BAC | NA | Rabbits; contents from small intestine and caecum and feces; ig, in vivo. | IT | [23] (M1) | |
| 588 | C32H45NO9 | 15-Deoxy BAC | NA | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P2) | |
| 586 | C32H43NO9 | Deacetoxy AC | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] | |
| 660 | C35H49NO11 | 8-O-Propionyl BAC | 74, propionic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] | ||||
| NA | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P8) | ||||
| 674 | C36H51NO11 | 8-O-Butyryl BAC | 88, butyric acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] | ||||
| NA | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P9) | ||||
| 688 | C37H53NO11 | 8-O-Valeryl BAC | 102, valeric acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] | ||||
| 700 | C38H53NO11 | 8-O-Hexenoyl BAC | 114, hexenoic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| NA | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P7) | ||||
| 690 | C36H51NO12 | 8-O-(3-Hydroxy)-butyryl BAC | NA | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P11) | |
| 702 | C38H55NO11 | 8-O-Hexanoyl BAC | 116, hexanoic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| 716 | C39H57NO11 | 8-O-Heptanoyl BAC | 130, heptanoic acid | Ibid. | Ibid. | Ibid. | |
| 722 | C40H51NO11 | 8-O-Phenylacetyl BAC | 136, phenylacetic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] | ||||
| 728 | C40H57NO11 | 8-O-Octenoyl BAC | NA | Rats; intestinal bacteria; anaerobic incubation at pH 7.0, in vitro. | IT | [22] (P3) | |
| 736 | C41H53NO11 | 8-O-Phenylpropionyl BAC | 150, phenylpropionic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| 800 | C45H69NO11 | 8-O-Tridecanoyl BAC | 214, tridecanoic acid | Ibid. | Ibid. | Ibid. | |
| 814 | C46H71NO11 | 8-O-Tetradecanoyl BAC | 228, tetradecanoic acid | Ibid. | Ibid. | Ibid. | |
| 828 | C47H73NO11 | 8-O-Pentadecanoyl BAC | 242, pentadecanoic acid | Ibid. | Ibid. | Ibid. | |
| 842 | C48H75NO11 | 8-O-Palmitoyl BAC | 256, palmitic acid | Ibid. | Ibid. | Ibid. | |
| 854 | C49H75NO11 | 8-O-Heptadecenoyl BAC | 268, heptadecenoic acid | Ibid. | Ibid. | Ibid. | |
| 856 | C49H77NO11 | 8-O-(Methyl)-palmitoyl BAC | 270, methyl palmitic acid | Ibid. | Ibid. | Ibid. | |
| 866 | C50H75NO11 | 8-O-Linoleyl BAC | 280, linoleic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] | ||||
| 868 | C50H77NO11 | 8-O-Oleoyl BAC | 282, oleic acid | Human; intestinal bacteria; anaerobic incubation, in vitro. | IT, FT-ICR | [24] | |
| 870 | C50H79NO11 | 8-O-Stearoyl BAC | 284, stearic acid | Ibid. | Ibid. | Ibid. | |
| 882 | C51H79NO11 | 8-O-(9)-Nonadecenoyl BAC | 296, nonadecene | Ibid. | Ibid. | Ibid. | |
| 886 | C50H79NO12 | 8-O-(3-Hydroxy)-stearoyl BAC | 300, 3-hydroxy stearic acid | Ibid. | Ibid. | Ibid. | |
| 954 | C56H91NO11 | 8-O-Tetracosanoyl BAC | 368, tetracosanoic acid | Ibid. | Ibid. | Ibid. | |
| 962 | C57H87NO11 | 8-O-Pentacosatrienoyl BAC | 376, pentacosatrienoic acid | Ibid. | Ibid. | Ibid. | |
|
| |||||||
| MA | 590 | C31H43NO10 | BMA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] |
| 572 | C31H41NO9 | Deacetoxy MA | NA | Ibid. | Ibid. | Ibid. | |
| 660 | C35H49NO11 | 8-O-Butyryl BMA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] | |
| 674 | C36H51NO11 | 8-O-Valeryl BMA | NA | Ibid. | Ibid. | Ibid. | |
| 852 | C49H73NO11 | 8-O-Linoleyl BMA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] | |
|
| |||||||
| HA | 574 | C31H43NO9 | BHA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] |
| Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] | |||||
| 556 | C31H41NO8 | Deacetoxy HA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] | |
| 630 | C34H47NO10 | 8-O-Propionyl BHA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.e | IT, MALDI source-FT-ICR | [27] | |
| 644 | C35H49NO10 | 8-O-Butyryl BHA | NA | Ibid. | Ibid. | Ibid. | |
| 658 | C36H51NO10 | 8-O-Valeryl BHA | NA | Ibid. | Ibid. | Ibid. | |
| 692 | C39H49NO10 | 8-O-Phenylacetyl BHA | NA | Ibid. | Ibid. | Ibid. | |
| 836 | C49H73NO10 | 8-O-Linoleyl BHA | NA | Rats; intestinal bacteria; anaerobic incubation, in vitro.c,d | IT | [25, 26] | |
aNot available.
bDeoxy may also be referred to as dehydroxy in the literature.
cDDA was produced through decoction of Aconiti Radix Cocta with Fritillariae Thunbergii Bulbus, Pinelliae Rhizoma Preparatum, and Ampelopsis Radix.
It is not clear whether these compounds were directly metabolized from DDAs or were originally ingested.
dDDA was produced through decoction of Aconiti Lateralis Radix Praeparata with Glycyrrhizae Radix and Rhizome as well as with Atractylodis Macrocephalae Rhizoma.
It is not clear whether these compounds were directly metabolized from DDAs or were originally ingested.
eIn addition to AC and HA monomers, DDAs were also generated from ethyl alcohol extraction ofRadix Aconiti.
It is not clear whether these compounds were directly metabolized from DDAs or were originally ingested.
*These metabolites were further biotransformed in the intestine. Metabolites of these intermediate products are listed in Table 4.