NCBI Taxonomy: 167918
Schnabelia (ncbi_taxid: 167918)
found 48 associated metabolites at genus taxonomy rank level.
Ancestor: Teucrieae
Child Taxonomies: Schnabelia terniflora, Schnabelia tetrodonta, Schnabelia nepetifolia, Schnabelia oligophylla, Schnabelia aureoglandulosa
Azelaic acid
Nonanedioic acid is an alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups. It has a role as an antibacterial agent, an antineoplastic agent, a dermatologic drug and a plant metabolite. It is a dicarboxylic fatty acid and an alpha,omega-dicarboxylic acid. It is a conjugate acid of an azelaate(2-) and an azelaate. Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is also produced by Malassezia furfur, also known as Pityrosporum ovale, which is a species of fungus that is normally found on human skin. Azelaic acid is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20\\\\\%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acids antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis. Azelaic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). The physiologic effect of azelaic acid is by means of Decreased Protein Synthesis, and Decreased Sebaceous Gland Activity. Azelaic Acid is a naturally occurring dicarboxylic acid produced by Malassezia furfur and found in whole grain cereals, rye, barley and animal products. Azelaic acid possesses antibacterial, keratolytic, comedolytic, and anti-oxidant activity. Azelaic acid is bactericidal against Proprionibacterium acnes and Staphylococcus epidermidis due to its inhibitory effect on the synthesis of microbial cellular proteins. Azelaic acid exerts its keratolytic and comedolytic effects by reducing the thickness of the stratum corneum and decreasing the number of keratohyalin granules by reducing the amount and distribution of filaggrin in epidermal layers. Azelaic acid also possesses a direct anti-inflammatory effect due to its scavenger activity of free oxygen radical. This drug is used topically to reduce inflammation associated with acne and rosacea. Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20\\\\\%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acids antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis. See also: Azelaic acid; niacinamide (component of) ... View More ... Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845). An alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups. Plants biology In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection.[7] It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.[8] Human biology The mechanism of action in humans is thought to be through the inhibition of hyperactive protease activity that converts cathelicidin into the antimicrobial skin peptide LL-37.[9] Polymers and related materials Esters of this dicarboxylic acid find applications in lubrication and plasticizers. In lubricant industries it is used as a thickening agent in lithium complex grease. With hexamethylenediamine, azelaic acid forms Nylon-6,9, which finds specialized uses as a plastic.[4] Medical Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.[10][11] It belongs to a class of medication called dicarboxylic acids. It works by killing acne bacteria that infect skin pores. It also decreases the production of keratin, which is a natural substance that promotes the growth[clarification needed] of acne bacteria.[12] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.[11] It clears the bumps and swelling caused by rosacea. In topical pharmaceutical preparations and scientific research AzA is typically used in concentrations between 15\\\% and 20\\\% but some research demonstrates that in certain vehicle formulations the pharmaceutical effects of 10\\\% Azelaic acid has the potential to be fully comparable to that of some 20\\\% creams.[13] Acne treatment Azelaic acid is effective for mild to moderate acne when applied topically at a 15\\\%-20\\\% concentration.[14][15][16][17] In patients with moderate acne, twice daily application over 3 months of 20\\\% AzA significantly reduced the number of comedones, papules, and pustules;[18][19] at this strength, it’s considered to be as effective as benzoyl peroxide 5\\\%, tretinoin 0.05\\\%, erythromycin 2\\\%, and oral tetracycline at 500 mg-1000 mg.[20][21] In a comparative review of effects of topical AzA, Salicylic acid, Nicotinamide, Sulfur, Zinc, and alpha-hydroxy acid, AzA had more high-quality evidence of effectiveness than the rest.[22] Results can be expected after 4 weeks of twice-daily treatment. The effectiveness of long term use is unclear, but it’s been recommended that AzA be used for at least 6 months continuously for maintenance.[20] Whitening agent Azelaic acid is used for treatment of skin pigmentation, including melasma and postinflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone.[23] As a tyrosinase inhibitor,[5] azelaic acid reduces synthesis of melanin.[24] According to one report in 1988, azelaic acid in combination with zinc sulfate in vitro was found to be a potent (90\\\% inhibition) 5α-reductase inhibitor, similar to the hair loss drugs finasteride and dutasteride.[25] In vitro research during mid-1980s evaluating azelaic acid's depigmenting (whitening) capability concluded it is effective (cytotoxic to melanocytes) at only high concentrations.[26] A 1996 review claimed 20\\\% AzA is as potent as 4\\\% hydroquinone after a period of application of three months without the latter's adverse effects and even more effective if applied along with tretinoin for the same period of time.[27][19] Azelaic acid is a nine-carbon dicarboxylic acid. Azelaic acid has antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis through inhibition of microbial cellular prorein synthesis. Azelaic acid has hypopigmentation action resulting from its ability to scavenge free radicals[1][2]. Azelaic acid is a nine-carbon dicarboxylic acid. Azelaic acid has antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis through inhibition of microbial cellular prorein synthesis. Azelaic acid has hypopigmentation action resulting from its ability to scavenge free radicals[1][2].
Maslinic acid
Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.; Maslinic 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. Maslinic 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. (PMID: 17292619) Maslinic 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. Maslinic 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. (PMID: 17292619). Maslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane. Maslinic acid is a natural product found in Chaenomeles speciosa, Salvia tomentosa, and other organisms with data available. See also: Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation. Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation.
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.
Amentoflavone
Amentoflavone is a biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum. It has a role as a cathepsin B inhibitor, an antiviral agent, an angiogenesis inhibitor, a P450 inhibitor and a plant metabolite. It is a biflavonoid, a hydroxyflavone and a ring assembly. Amentoflavone is a natural product found in Podocarpus elongatus, Austrocedrus chilensis, and other organisms with data available. A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum. D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors Amentoflavone is found in fruits. Amentoflavone is obtained from Viburnum prunifolium (black haw Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4].
Maslinic Acid
A pentacyclic triterpenoid that is 3alpha-hydroxy epimer of maslinic acid. Isolated from Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity. Annotation level-1 Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation. Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation.
sitosterol
A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].
Amentoflavone
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 4341; CONFIDENCE confident structure Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4].
Azelaic Acid
D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000970 - Antineoplastic Agents D003879 - Dermatologic Agents Annotation level-2 Azelaic acid is a nine-carbon dicarboxylic acid. Azelaic acid has antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis through inhibition of microbial cellular prorein synthesis. Azelaic acid has hypopigmentation action resulting from its ability to scavenge free radicals[1][2]. Azelaic acid is a nine-carbon dicarboxylic acid. Azelaic acid has antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis through inhibition of microbial cellular prorein synthesis. Azelaic acid has hypopigmentation action resulting from its ability to scavenge free radicals[1][2].