Chemical Formula: C23H22O6
Chemical Formula C23H22O6
Found 88 metabolite its formula value is C23H22O6
Rotenone
Rotenone appears as colorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste. (NTP, 1992) Rotenone is a member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). It has a role as a phytogenic insecticide, a mitochondrial NADH:ubiquinone reductase inhibitor, a metabolite, an antineoplastic agent, a toxin and a piscicide. It is an organic heteropentacyclic compound and a member of rotenones. Rotenone is an isoflavone compound that naturally occurs in the jicama vine plant as well as many Fabaceae plants. It has broad spectrum insecticide and pesticide activity and is also toxic to fish. Rotenone is a natural product found in Pachyrhizus erosus, Millettia ferruginea, and other organisms with data available. Rotenone is a naturally occurring organic heteropentacyclic compound and member of rotenones that is found in the roots of several plant species. It is a mitochondrial NADH:ubiquinone reductase inhibitor, toxin, and metabolite, and is used as an antineoplastic agent and insecticide. It is characterized as a colorless to brownish or a white to brownish-white crystalline solid that is odorless. Exposure occurs by inhalation, ingestion, or contact. Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinsons disease. (Wikipedia) Rotenone has been shown to exhibit apoptotic, neuroprotectant and neuroprotective functions (A7776, A7777, A7777).Rotenone belongs to the family of Rotenoids. These are phenolic compounds containing aA cis-fused tetrahydrochromeno[3,4-b]chromenenucleus. Many rotenoids contain an additional ring, e.g rotenone[1]. (Reference: [1] IUPAC. Compendium of Chemical Terminology, 2nd ed. (the Gold Book). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. (PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1364)). A botanical insecticide that is an inhibitor of mitochondrial electron transport. Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinsons disease. A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). Widely distrib. in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean) D004791 - Enzyme Inhibitors > D014475 - Uncoupling Agents D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production.
Legumelin
Legumelin, also known as (-)-cis-deguelin, is a member of the class of compounds known as rotenones. Rotenones are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, legumelin is considered to be a flavonoid lipid molecule. Legumelin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Legumelin can be found in soy bean, which makes legumelin a potential biomarker for the consumption of this food product. Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB. Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB. Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB.
Garcinone B
Constituent of Garcinia mangostana (mangosteen). Garcinone B is found in fruits and purple mangosteen. Garcinone B is found in fruits. Garcinone B is a constituent of Garcinia mangostana (mangosteen)
Deguelin
Morusignin J
Deguelin
Deguelin is a rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. It has a role as an apoptosis inducer, an antineoplastic agent, a plant metabolite, an angiogenesis inhibitor, an antiviral agent, a mitochondrial NADH:ubiquinone reductase inhibitor, an anti-inflammatory agent and an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor. It is a member of rotenones, an aromatic ether, an organic heteropentacyclic compound and a diether. Deguelin is a natural product found in Tephrosia vogelii, Derris montana, and other organisms with data available. A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB. Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB. Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB.
1,2,12,12a-Tetrahydro-2-isopropenyl-8,9-dimethoxy-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Dehydrodihydrorotenone
2,4,5-Trimethoxy-2,2-dimethylpyrano[5,6:6,7]isoflavone
3,4-Dihydroxy-7-methoxy-8-prenyl-5-(2-hydroxyisopropyl)-[2,3:5,6]furanoflavanone
(E)-3,4-Methylenedioxy-2-methoxy-6,6-dimethylchromeno-[2,3:4,3]-9-methoxychalcone
8-C-Methylvellokaempferol 3,5-dimethyl ether
5,7,10-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Muxiangrin I
(Z)-3,4-Methylenedioxy-2-methoxy-6,6-dimethylchromeno-[2,3:4,3]-9-methoxychalcone
Purpurin
Purpurin is a naturally occurring organic compound that belongs to the anthraquinone family. It is known for its distinctive red color and is found in various plants, particularly in the bark and roots of certain trees, as well as in some soil bacteria. The compound has a long history of use as a natural dye, especially in ancient times for coloring fabrics and as a component in inks. Chemically, Purpurin is characterized by a structure consisting of three fused benzene rings forming an anthraquinone skeleton, with two carboxylic acid groups attached to two of the benzene rings. This structure is responsible for its color and chemical properties. The presence of the carboxylic acid groups makes Purpurin soluble in alkaline solutions, which is why it was historically used in dyeing processes. In addition to its historical use as a dye, Purpurin has also found applications in modern science. It has been used as a fluorescent marker in biological and medical research due to its ability to absorb light at specific wavelengths and emit fluorescence. This property makes it useful in techniques such as fluorescence microscopy and imaging. Moreover, Purpurin and its derivatives have been studied in the fields of pharmacology and materials science. The compound's unique chemical structure and properties have made it a subject of interest for developing new pharmaceuticals and advanced materials. Its natural occurrence and the potential for sustainable synthesis from plant sources also contribute to its relevance in modern chemistry and related disciplines.
Rotenone
Origin: Plant, Pyrans relative retention time with respect to 9-anthracene Carboxylic Acid is 1.283 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.281 Acquisition and generation of the data is financially supported by the Max-Planck-Society D004791 - Enzyme Inhibitors > D014475 - Uncoupling Agents D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals IPB_RECORD: 2241; CONFIDENCE confident structure Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production.
1,6,7-trihydroxy-6,6-dimethyl-2H-pyrano(2,3:3,2)-4-(3-methylbut-2-enyl)xanthone
A member of the class of pyranoxanthones that is 2H,6H-pyrano[3,2-b]xanthen-6-one substituted by hydroxy groups at positions 5, 8 and 9, geminal methyl groups at position 2 and a prenyl group at position 12. Isolated from Garcinia lancilimba, it exhibits inhibitory effects on human cancer cell line.
(+)-purpurin|(+)-Purpurin 2|7a,10,10a-Triepimer -Purpurin+
4,5-dihydro-1,5-dihydroxy-6,6-dimethylpyrano(2,3:6,7)-4,4,5-trimethylfurano(2,3:3,4)xanthone
5,10-dihydroxy-12-((Z)-3-hydroxymethylbut-2-enyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one|garcinexanthone E
1,4,6-trihydroxy-5-(1,1-dimethyl-2-propenyl)-6,6-dimethylpyrano[2,3:3,2]xanthone|soulattrin
4,2?,4?trihydroxy-6?-methoxy-3?(2??-hydroxybenzyl)dihydrochalcone
2-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-7-hydroxy-4,4-dimethylchromane|4-[3-(3,5-dihydroxyphenyl)-3,4-dihydro-7-hydroxy-4,4-dimethyl-2H-1-benzopyran-2-yl]benzene-1,3-diol|artoxanthochromane
10-(1,1-Dimethyl-2-propenyl)-7,9,12-trihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one|macluraxanthone
5,9,10-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
(E)-3-{2,3-dihydro-2-[2-[(E)-p-coumaroyloxy]-1-methylethyl]-5-benzofuranyl}-2-propenoic acid
5-hydroxy-7-methoxy-8-methyl-3,4-methylenedioxy-5-(3-methyl-but-2-enyl)-3,4-methylenedioxyflavone
1,5,6-trihydroxy-6,6-dimethyl-2H-pyrano(2,3:3,4)-2-(3-methylbut-2-enyl)xanthone
A member of the class of pyranoxanthones that is 3H,7H-pyrano[2,3-c]xanthen-7-one substituted by hydroxy groups at positions 6, 10 and 11, geminal methyl groups at position 3 and a prenyl group at position 5. Isolated from Garcinia lancilimba, it exhibits inhibitory effects on human cancer cell line.