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Table 2 Secondary metabolites isolated from C. ambrosioides

From: Ethnomedical uses, chemical constituents, and evidence-based pharmacological properties of Chenopodium ambrosioides L.: extensive overview

Compound

Part used/extract (fraction)

References

Alkaloids

 1-Piperoylpiperidine

Whole plant/methanol (n-butanol)

[174]

Coumarins

 1,2-Benzopyrone

Leaves/ethanol 70% (n-butanol)

[175]

 Scopoletin

Whole plant/methanol (dichloromethane)

[174]

Cyclohexanones

 4-Hydroxy-4-methyl-2-cyclohexen-1-one

Whole plant/–

[176]

Fatty acids

 Octadecanoic acid

Whole plant/methanol (ethyl acetate)

[174]

Flavonoids

 Kaempferol

Fruits/methanol (ethyl acetate)

[177]

Leaves/ethanol 70% (n-butanol)

[175]

 Isorhamnetin

Fruits/methanol (ethyl acetate)

[177]

 Patuletin

Whole plant/–

[176]

 Quercetin

Fruits/methanol (ethyl acetate)

[177]

Glycosides

 Benzyl beta-d-glucopyranoside

Whole plant/–

[176]

 Chenopodioside A

Roots/methanol (−)

[178]

 Chenopodioside B

Roots/methanol (−)

[178]

 Dendranthemoside B

Whole plant/–

[176]

 Kaempferol 3-O-α-l-1C4–rhamnopyranoside (afzelin)

Leaves/ethanol 70% (n-butanol)

[175]

 Kaempferol 3-O-α-l-1C4-rhamnosyl-(1‴→2″)-β-d-4C1-xylopyranoside

Leaves/ethanol 70% (n-butanol)

[175]

 Kaempferol 3-rhamnoside-4′-xyloside

Fruits/methanol (ethyl acetate)

[177]

 Kaempferol 3-rhamnoside-7-xyloside

Fruits/methanol (ethyl acetate)

[177]

 Kaempferol 7-O-α-l-1C4–rhamnopyranoside

Leaves/ethanol 70% (n-butanol)

[175]

 Kaempferol 7-rhamnoside

Leaves/ethyl acetate (−)

[179]

 Kaempferol-3,7-di-O-alpha-l-rhamnopyranoside

Whole plant/–

[176]

 Kaempferol-7-O-alpha-l-rhamnopyranoside

Whole plant/–

[176]

 Kaempfrol 7-rhamnoside (ambroside)

Leaves/ethyl acetate (−)

[179]

 Quercetin-7-O-alpha-l-rhamnopyranoside

Whole plant/–

[176]

 Scutellarein-7-O-α-rhamnopyranosyl-(1→2)-α-rhamnopyranoside

Aerial parts/ethanol (ethyl acetate)

[180]

 Scutellarein-7-O-α-rhamnopyranosyl-(1→2)-α-rhamnopyranosyl-(1→2)-α-rhamnopyranoside

Aerial parts/ethanol (ethyl acetate)

[180]

Lignanes

 Syringaresinol

Whole plant/–

[176]

Monoterpenes

 (−) (1R*,2S*,3S*,4S*)-1,2,3,4-Tetrahydroxy-p-menthane

Aerial parts/n-hexane-ethyl acetate-methanol (n-hexane-ethyl acetate, 1:1)

[181]

 (−) (1R*,4S*)-1,4-Dihydroxy-p-menth-2-ene

Aerial parts/ n-hexane-ethyl acetate-methanol (n-hexane-ethyl acetate, 1:1)

[181]

 (−)-(1R,4S)-p-Mentha-2,8-dien-1-hydroperoxide

Aerial parts/ethyl acetate (diethyl ether-soluble)

[182]

 (−)-(1S,4S)-p-Mentha-2,8-dien-1-hydroperoxide

Aerial parts/ethyl acetate (diethyl ether-soluble)

[182]

 (−)-(2R,4S)-p-Mentha-1(7),8-dien-2-hydroperoxide

Aerial parts/ethyl acetate (diethyl ether-soluble)

[182]

 (−)-(2S,4S)-p-Mentha-1(7),8-dien-2-hydroperoxide

Aerial parts/ethyl acetate (diethyl ether-soluble)

[182]

 (1R,2S)-3-p-Menthen-1,2-diol

Stems/ethanol (ethyl acetate)

[183]

 (1R,2S,3S,4S)- 1,2,3,4-Tetrahydroxy-p-menthane

Stems/ethanol (ethyl acetate)

[183]

 (1R,4S)-p-Menth-2-en-1-ol

Stems/ethanol (ethyl acetate)

[183]

 (1S,2S,3R,4S)-1-Methyl-4-(propan-2-yl)cyclohexane-1,2,3,4-tetrol

Stems/ethanol (ethyl acetate)

[183]

 1,2,3,4-Tetrahydroxy-p-menthane

Leaves and stems/ethanol (hexane-ethyl acetate)

[184]

 1,2:3,4-Diepoxy-p-menthane

Leaves/essential oil (ethyl acetate)

[185]

 1,4-Dihydroxyp-menth-2-ene

Stems/ethanol (ethyl acetate)

[183]

 1,4-Epoxy-p-menth-2-ene

Leaves/essential oil (ethyl acetate)

[185]

 1-Methyl-4β- isopropyl-1-cyclohexene4α,5α,6α-triol

Stems/ethanol (ethyl acetate)

[183]

 4-Hydroxy-4(α or β)-isopropyl-2-methyl-2-cyclohexen-1-one

Stems/ethanol (ethyl acetate)

[183]

 Ascaridole

Whole plant/ethanol (hexane-ethyl acetate)

[186]

Aerial part/methanol (hexane)

[187]

Aerial parts/ethyl acetate (diethyl ether-soluble)

[182]

Aerial parts/–

[188]

Leaves and stems/ethanol (hexane-ethyl acetate)

[184]

 Chenopanone

Aerial parts/ n-hexane-ethyl acetate-methanol (n-hexane-ethyl acetate, 1:1)

[181]

 Cis-p-Menthadiene-l(7),8ol-2

Whole plant/ethanol (hexane-ethyl acetate)

[186]

 Isoascaridole

Aerial parts/–

[188]

 α-Terpinene

Aerial parts/–

[188]

 δ-4-Carene

Aerial parts/–

[188]

ρ-Cymene

Aerial parts/–

[188]

Phenolic amides

 N-Trans-feruloyl tyramine

Whole plant/–

[176]

Polyphenolic acids

 Caffeic acid

Leaves/ethanol 70% (n-butanol)

[175]

Sterols

 2,2-Dihydro-spinasterol

Whole plant/acetone (methanol-acetonitrile)

[189]

 Avenasterol

Whole plant/acetone (methanol-acetonitrile)

[189]

 Spinasterol

Whole plant/acetone (methanol-acetonitrile)

[189]

 Stigmasterol

Whole plant/methanol (ethyl acetate)

[174]

 β-sitosterol

Whole plant/methanol (ethyl acetate)

[174]

Other compounds

 Chenopodiumamine A

Whole plant/ethanol (chloroform)

[190]

 Chenopodiumamine B

Whole plant/ethanol (chloroform)

[190]

 Chenopodiumamine C

Whole plant/ethanol (chloroform)

[190]

 Chenopodiumamine D

Whole plant/ethanol (chloroform)

[190]

 Chenopodiumoside A

Whole plant/ethanol (chloroform)

[190]

 Grasshopper ketone

Whole plant/–

[176]