NCBI Taxonomy: 1382013
Helicteres isora (ncbi_taxid: 1382013)
found 103 associated metabolites at species taxonomy rank level.
Ancestor: Helicteres
Child Taxonomies: none taxonomy data.
Rosmarinic acid
Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects (PMID: 12482446, 15120569). BioTransformer predicts that rosmarinic acid is a product of methylrosmarinic acid metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in humans and human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). (R)-rosmarinic acid is a stereoisomer of rosmarinic acid having (R)-configuration. It has a role as a plant metabolite and a geroprotector. It is a conjugate acid of a (R)-rosmarinate. It is an enantiomer of a (S)-rosmarinic acid. Rosmarinic acid is a natural product found in Dimetia scandens, Scrophularia scorodonia, and other organisms with data available. See also: Rosemary Oil (part of); Comfrey Root (part of); Holy basil leaf (part of) ... View More ... D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors Isolated from rosemary, mint, sage, thyme, lemon balm and other plants D002491 - Central Nervous System Agents > D000700 - Analgesics A stereoisomer of rosmarinic acid having (R)-configuration. D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively.
Betulinic acid
Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].
Oleanolic acid
Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.
beta-Sitosterol 3-O-beta-D-galactopyranoside
Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. beta-Sitosterol 3-O-beta-D-galactopyranoside is found in herbs and spices. beta-Sitosterol 3-O-beta-D-galactopyranoside is a constituent of Hibiscus sabdariffa (roselle) leaves. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.
Trifolin
Kaempferol 3-o-beta-d-galactopyranoside, also known as trifolin or trifolioside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-o-beta-d-galactopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-o-beta-d-galactopyranoside can be found in horseradish, which makes kaempferol 3-o-beta-d-galactopyranoside a potential biomarker for the consumption of this food product. Kaempferol 3-O-beta-D-galactoside is a beta-D-galactoside compound with a 4,5,7-trihydroxychromen-3-yl group at the anomeric position. It has a role as a plant metabolite and an antifungal agent. It is a beta-D-galactoside, a monosaccharide derivative, a glycosyloxyflavone and a trihydroxyflavone. It is functionally related to a kaempferol. It is a conjugate acid of a kaempferol 3-O-beta-D-galactoside(1-). Trifolin is a natural product found in Lotus ucrainicus, Saxifraga tricuspidata, and other organisms with data available. Isoastragalin is found in fats and oils. Isoastragalin is isolated from Gossypium hirsutum (cotton) and other plant species. A beta-D-galactoside compound with a 4,5,7-trihydroxychromen-3-yl group at the anomeric position.
Rosmarinic acid
The (S)-stereoisomer of rosmarinic acid. The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.731 Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively.
Hibifolin
Isoscutellarein 4-methyl ether 8-glucuronide
C22H20O12 (476.09547200000003)
Hibifolin
Hibifolin is a natural product found in Helicteres isora, Abelmoschus manihot, and Sedum album with data available. Hibifolin, a flavonol glycoside, is a potential inhibitor of adenosine deaminase (ADA), with a Ki of 49.92 μM. Hibifolin protects neurons against beta-amyloid-induced neurotoxicity[1][2]. Hibifolin, a flavonol glycoside, is a potential inhibitor of adenosine deaminase (ADA), with a Ki of 49.92 μM. Hibifolin protects neurons against beta-amyloid-induced neurotoxicity[1][2].
Trifolin
Isolated from Gossypium hirsutum (cotton) and other plant subspecies Isoastragalin is found in fats and oils. Isolated from liquorice (Glycyrrhiza glabra). Acetylastragalin is found in herbs and spices. Widespread occurrence in plant world, e.g. Pinus sylvestris (Scotch pine) and fruits of Scolymus hispanicus (Spanish salsify). Kaempferol 3-galactoside is found in many foods, some of which are horseradish, almond, peach, and tea.
betulinic acid
Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].
Daucosterol
Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.
Mairin
C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].
Caryophyllin
Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.
(2s)-2-{[(2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}-3-(4-hydroxyphenyl)propanoic acid
C24H26O12 (506.14241960000004)
6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid
C22H20O18S2 (636.0091060000001)
(2s)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-{[(2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}propanoic acid
methyl 6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate
5,8-dihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl (2e)-3-[9-({[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}carbonyl)-1,4,5-trihydroxy-14-oxotetracyclo[8.3.1.0²,⁷.0⁸,¹³]tetradeca-2,4,6,11-tetraen-11-yl]prop-2-enoate
3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-{[3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}propanoic acid
methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate
(2s)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}propanoic acid
butyl 6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
2-{[3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}-3-(4-hydroxyphenyl)propanoic acid
C24H26O12 (506.14241960000004)
methyl 3-(3,4-dihydroxyphenyl)-6-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-8-oxobicyclo[2.2.2]oct-5-ene-2-carboxylate
methyl (1s,2r,3s,4s,7s)-3-(3,4-dihydroxyphenyl)-6-[(1e)-3-{[(2s)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl]-7-hydroxy-8-oxobicyclo[2.2.2]oct-5-ene-2-carboxylate
(2s)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl (2e)-3-[(1s,4s,5s,6r,7r,8s)-5-(3,4-dihydroxyphenyl)-6-({[(2s)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}carbonyl)-7,8-dihydroxybicyclo[2.2.2]oct-2-en-2-yl]prop-2-enoate
(2s,3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
C22H20O12 (476.09547200000003)
butyl (2s,3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
C22H20O12 (476.09547200000003)
(2s,3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid
C21H18O18S2 (621.9934568000001)
6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4-dihydroxy-5-(sulfooxy)oxane-2-carboxylic acid
C22H20O15S (556.0522890000001)
6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid
C21H18O18S2 (621.9934568000001)
(2s,3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-4-hydroxy-3,5-bis(sulfooxy)oxane-2-carboxylic acid
C22H20O18S2 (636.0091060000001)
methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate
butyl (2r,3r,4r,5s,6r)-6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
3-(3,4-dihydroxyphenyl)-2-{[3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}propanoic acid
butyl (3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
methyl 6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate
3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl 3-[5-(3,4-dihydroxyphenyl)-6-({[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}carbonyl)-7,8-dihydroxybicyclo[2.2.2]oct-2-en-2-yl]prop-2-enoate
(2s,3s,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-3,4-dihydroxy-5-(sulfooxy)oxane-2-carboxylic acid
C22H20O15S (556.0522890000001)