Evidence-Based Complementary and Alternative Medicine

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In Vivo and In Vitro Metabolites from the Main Diester and Monoester Diterpenoid Alkaloids in a Traditional Chinese Herb, the Aconitum Species

Table 3

Metabolites of AC, MA, and HA converted in intestine.


DDAs	(ESI⁺)	Formula	Identification	Neutral loss (Da), identification of fatty acid	Metabolic procedure	MS detection	References

AC	662	C₃₄H₄₇NO₁₂	10-Hydroxy AC	NA^a	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)
	632	C₃₃H₄₅NO₁₁	16-O-Demethyl AC^*	NA	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)
			Indaconitine (15-deoxy AC)^b		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]
	688	C₃₇H₅₃NO₁₁	8-O-Valeryl BAC	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]
	700	C₃₈H₅₃NO₁₁	8-O-Hexenoyl BAC	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]
	722	C₄₀H₅₁NO₁₁	8-O-Phenylacetyl BAC	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]
	866	C₅₀H₇₅NO₁₁	8-O-Linoleyl BAC	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]
	574	C₃₁H₄₃NO₉	BHA	NA	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]

Not 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.