NCBI Taxonomy: 128741

Marshallia obovata (ncbi_taxid: 128741)

found 44 associated metabolites at species taxonomy rank level.

Ancestor: Marshallia

Child Taxonomies: none taxonomy data.

(-)-dehydrocostus lactone

Azuleno(4,5-b)furan-2(3H)-one, decahydro-3,6,9-tris(methylene)-, (3aS-(3a.alpha.,6a.alpha.,9a.alpha.,9b.beta.))-

C15H18O2 (230.1307)


Dehydrocostus lactone is an organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone. It has a role as a metabolite, a trypanocidal drug, an antineoplastic agent, a cyclooxygenase 2 inhibitor, an antimycobacterial drug and an apoptosis inducer. It is a sesquiterpene lactone, a guaiane sesquiterpenoid, an organic heterotricyclic compound and a gamma-lactone. Dehydrocostus lactone is a natural product found in Marshallia obovata, Cirsium carolinianum, and other organisms with data available. See also: Arctium lappa Root (part of). An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone. CONFIDENCE standard compound; ML_ID 36 Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea costus. IC50 value: Target: In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. In vivo: Dehydrocostus Lactone decreased the TNF-alpha level in LPS-activated systems in vivo [3]. Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea costus. IC50 value: Target: In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. In vivo: Dehydrocostus Lactone decreased the TNF-alpha level in LPS-activated systems in vivo [3].

   

Methyl caffeate

Methyl 3,4-dihydroxycinnamate

C10H10O4 (194.0579)


Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities. Methyl caffeate also exhibits α-glucosidase inhibition activity, oxidative stress inhibiting activity, anti-platelet activity, antiproliferative activity in cervix adenocarcinoma and anticancer activity in lung and leukmia cell lines[1]. Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities. Methyl caffeate also exhibits α-glucosidase inhibition activity, oxidative stress inhibiting activity, anti-platelet activity, antiproliferative activity in cervix adenocarcinoma and anticancer activity in lung and leukmia cell lines[1].

   

methyl 3-(4-hydroxyphenyl)prop-2-enoate

methyl 3-(4-hydroxyphenyl)prop-2-enoate

C10H10O3 (178.063)


   

Methyl 3,4-dihydroxycinnamate

Methyl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C10H10O4 (194.0579)


   

Dehydrocostus lactone

3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

C15H18O2 (230.1307)


Dehydrocostus lactone, also known as dehydro-alpha-curcumene, belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Dehydrocostus lactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydrocostus lactone can be found in burdock and sweet bay, which makes dehydrocostus lactone a potential biomarker for the consumption of these food products.

   

Methyl p-coumarate

4-coumaric acid methyl ester, (E)-isomer

C10H10O3 (178.063)


Methyl p-coumarate, also known as 4-coumaric acid methyl ester, is a member of the class of compounds known as coumaric acid esters. Coumaric acid esters are aromatic compounds containing an ester derivative of coumaric acid. Methyl p-coumarate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Methyl p-coumarate can be found in bamboo shoots and garden onion, which makes methyl p-coumarate a potential biomarker for the consumption of these food products. Methyl p-coumarate (Methyl 4-hydroxycinnamate), an esterified derivative of p-Coumaric acid (pCA), is isolated from the flower of Trixis michuacana var longifolia. Methyl p-coumarate could inhibit the melanin formation in B16 mouse melanoma cells. Methyl p-coumarate also has strong in vitro inhibitory effect on A. alternata and other pathogens[1][2]. Methyl p-coumarate (Methyl 4-hydroxycinnamate), an esterified derivative of p-Coumaric acid (pCA), is isolated from the flower of Trixis michuacana var longifolia. Methyl p-coumarate could inhibit the melanin formation in B16 mouse melanoma cells. Methyl p-coumarate also has strong in vitro inhibitory effect on A. alternata and other pathogens[1][2].

   

beta-Cedrene

(1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane

C15H24 (204.1878)


≈í¬±-Cedrene also known as Cedrene, belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. ≈í¬±-Cedrene is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. ≈í¬±-Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known cedrene isomers, namely ≈í¬±- and ≈í‚â§-cedrene, which differ in the position of a double bond. Beta-cedrene, also known as β-cedrene or cedrone, is a member of the class of compounds known as cedrane and isocedrane sesquiterpenoids. Cedrane and isocedrane sesquiterpenoids are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Beta-cedrene can be found in sweet basil, which makes beta-cedrene a potential biomarker for the consumption of this food product.

   

dehydrocostus lactone

NCGC00385838-01_C15H18O2_Azuleno[4,5-b]furan-2(3H)-one, decahydro-3,6,9-tris(methylene)-, (3aS,6aR,9aR,9bS)-

C15H18O2 (230.1307)


Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea costus. IC50 value: Target: In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. In vivo: Dehydrocostus Lactone decreased the TNF-alpha level in LPS-activated systems in vivo [3]. Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea costus. IC50 value: Target: In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. In vivo: Dehydrocostus Lactone decreased the TNF-alpha level in LPS-activated systems in vivo [3].

   

2-Isopropyl-5-methylphenyl 2-methylbutanoate

2-Isopropyl-5-methylphenyl 2-methylbutanoate

C15H22O2 (234.162)


   

Neophellamuretin

(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

C20H20O6 (356.126)


Neophellamuretin is a natural product found in Marshallia obovata, Phellodendron chinense var. glabriusculum, and other organisms with data available.

   

Costic acid

2-(4a-methyl-8-methylidene-decahydronaphthalen-2-yl)prop-2-enoic acid

C15H22O2 (234.162)


   

3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C32H52O2 (468.3967)


   

(2r,3s,4s)-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,4,7-triol

(2r,3s,4s)-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,4,7-triol

C21H24O6 (372.1573)


   

{4-[(2r)-2-methyloxiran-2-yl]-3-[(2-methylpropanoyl)oxy]phenyl}methyl 3-methylbutanoate

{4-[(2r)-2-methyloxiran-2-yl]-3-[(2-methylpropanoyl)oxy]phenyl}methyl 3-methylbutanoate

C19H26O5 (334.178)


   

2-(4-hydroxyphenyl)-3,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,7-diol

2-(4-hydroxyphenyl)-3,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,7-diol

C22H26O6 (386.1729)


   

(2r,3s,4s)-2-(4-hydroxyphenyl)-3,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,7-diol

(2r,3s,4s)-2-(4-hydroxyphenyl)-3,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,7-diol

C22H26O6 (386.1729)


   

2-(4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl)prop-2-enoic acid

2-(4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl)prop-2-enoic acid

C15H22O2 (234.162)


   

{5-hydroxy-8,8-dimethyl-4-oxopyrano[3,2-g]chromen-2-yl}methyl 2-methylpropanoate

{5-hydroxy-8,8-dimethyl-4-oxopyrano[3,2-g]chromen-2-yl}methyl 2-methylpropanoate

C19H20O6 (344.126)


   

2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,4,7-triol

2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,4,7-triol

C21H24O6 (372.1573)


   

5-hydroxy-2-(hydroxymethyl)-8,8-dimethylpyrano[3,2-g]chromen-4-one

5-hydroxy-2-(hydroxymethyl)-8,8-dimethylpyrano[3,2-g]chromen-4-one

C15H14O5 (274.0841)


   

5-hydroxy-7-methoxy-2-methyl-6-(3-methylbut-2-en-1-yl)chromen-4-one

5-hydroxy-7-methoxy-2-methyl-6-(3-methylbut-2-en-1-yl)chromen-4-one

C16H18O4 (274.1205)


   

(+)-β-cedrene

(+)-β-cedrene

C15H24 (204.1878)


   

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

C20H20O6 (356.126)


   

(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

C20H20O6 (356.126)


   

5-hydroxy-2,8,8-trimethylpyrano[3,2-g]chromen-4-one

5-hydroxy-2,8,8-trimethylpyrano[3,2-g]chromen-4-one

C15H14O4 (258.0892)


   

(2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-2h,3h-pyrano[2,3-f]chromen-4-one

(2r,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-2h,3h-pyrano[2,3-f]chromen-4-one

C20H18O6 (354.1103)


   

2-isopropyl-5-methylphenyl 2-methylpropanoate

2-isopropyl-5-methylphenyl 2-methylpropanoate

C14H20O2 (220.1463)


   

(2s,4s)-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,5-diol

(2s,4s)-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,5-diol

C21H24O5 (356.1624)


   

[4-(2-methyloxiran-2-yl)-3-[(2-methylpropanoyl)oxy]phenyl]methyl 2-methylbutanoate

[4-(2-methyloxiran-2-yl)-3-[(2-methylpropanoyl)oxy]phenyl]methyl 2-methylbutanoate

C19H26O5 (334.178)


   

(1s,3as,5ar,7s,9as,11as)-3a,6,6,9a,11a-pentamethyl-1-[(2r)-6-methylhept-5-en-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

(1s,3as,5ar,7s,9as,11as)-3a,6,6,9a,11a-pentamethyl-1-[(2r)-6-methylhept-5-en-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C32H52O2 (468.3967)


   

2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,5-diol

2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,5-diol

C21H24O5 (356.1624)


   

3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-2h,3h-pyrano[2,3-f]chromen-4-one

3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-2h,3h-pyrano[2,3-f]chromen-4-one

C20H18O6 (354.1103)


   

{4-[(2r)-2-methyloxiran-2-yl]-3-[(2-methylpropanoyl)oxy]phenyl}methyl 2-methylpropanoate

{4-[(2r)-2-methyloxiran-2-yl]-3-[(2-methylpropanoyl)oxy]phenyl}methyl 2-methylpropanoate

C18H24O5 (320.1624)


   

2-(4-hydroxyphenyl)-4,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,7-diol

2-(4-hydroxyphenyl)-4,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,7-diol

C22H26O6 (386.1729)


   

[4-(2-methyloxiran-2-yl)-3-[(2-methylpropanoyl)oxy]phenyl]methyl 2-methylpropanoate

[4-(2-methyloxiran-2-yl)-3-[(2-methylpropanoyl)oxy]phenyl]methyl 2-methylpropanoate

C18H24O5 (320.1624)


   

(2r,3s,4s)-2-(4-hydroxyphenyl)-4,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,7-diol

(2r,3s,4s)-2-(4-hydroxyphenyl)-4,5-dimethoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3,7-diol

C22H26O6 (386.1729)


   

2-[(2r,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]prop-2-enoic acid

2-[(2r,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]prop-2-enoic acid

C15H22O2 (234.162)


   

2-isopropyl-5-methylphenyl (2r)-2-methylbutanoate

2-isopropyl-5-methylphenyl (2r)-2-methylbutanoate

C15H22O2 (234.162)


   

4β-hydroxyobovatachromene

4β-hydroxyobovatachromene

C21H22O6 (370.1416)


   

(2s,4r)-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,5-diol

(2s,4r)-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-4,5-diol

C21H24O5 (356.1624)


   

2-(4-hydroxyphenyl)-5-methoxy-8,8-dimethyl-2h,3h,4h-pyrano[2,3-f]chromene-3,4-diol

2-(4-hydroxyphenyl)-5-methoxy-8,8-dimethyl-2h,3h,4h-pyrano[2,3-f]chromene-3,4-diol

C21H22O6 (370.1416)


   

2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0¹,⁵]undecane

2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0¹,⁵]undecane

C15H24 (204.1878)


   

{4-[(2r)-2-methyloxiran-2-yl]-3-[(2-methylpropanoyl)oxy]phenyl}methyl (2r)-2-methylbutanoate

{4-[(2r)-2-methyloxiran-2-yl]-3-[(2-methylpropanoyl)oxy]phenyl}methyl (2r)-2-methylbutanoate

C19H26O5 (334.178)


   

[4-(2-methyloxiran-2-yl)-3-[(2-methylpropanoyl)oxy]phenyl]methyl 3-methylbutanoate

[4-(2-methyloxiran-2-yl)-3-[(2-methylpropanoyl)oxy]phenyl]methyl 3-methylbutanoate

C19H26O5 (334.178)