NCBI Taxonomy: 49703

Bulbine (ncbi_taxid: 49703)

found 156 associated metabolites at genus taxonomy rank level.

Ancestor: Asphodeloideae

Child Taxonomies: Bulbine succulenta, Bulbine crassa, Bulbine vagans, Bulbine wiesei, Bulbine glauca, Bulbine bulbosa, Bulbine alooides, Bulbine latifolia, Bulbine fistulosa, Bulbine frutescens, Bulbine abyssinica, Bulbine macrocarpa, Bulbine semibarbata, unclassified Bulbine

Vanillic acid

4-hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity (PMID: 16899266). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072, 10543794, 11728709, 9579070). Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity. (PMID: 16899266). Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a monohydroxybenzoic acid and a methoxybenzoic acid. It is a conjugate acid of a vanillate. Vanillic acid is a natural product found in Ficus septica, Haplophyllum cappadocicum, and other organisms with data available. Vanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. Vanillic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=121-34-6 (retrieved 2024-06-29) (CAS RN: 121-34-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

   

4-Hydroxycinnamic acid

(E)-3-(4-hydroxyphenyl)prop-2-enoic acid

C9H8O3 (164.0473418)


4-Hydroxycinnamic acid, also known as p-Coumaric acid, is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate. p-coumaric acid is an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid. It is a crystalline solid that is slightly soluble in water, but very soluble in ethanol and diethyl ether. 4-Hydroxycinnamic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 4-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as pepper (Capsicum frutescens), pineapples, and sunflowers and in a lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as wild rices, soursops, garden onions, hyssops, and avocado. 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate. 4-Hydroxycinnamic acid is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. trans-4-Coumaric acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Galium aparine whole (part of); Lycium barbarum fruit (part of) ... View More ... Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid is found in many foods, some of which are garden onion, turmeric, green bell pepper, and common thyme. D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants The trans-isomer of 4-coumaric acid. D000890 - Anti-Infective Agents Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 168 KEIO_ID C024 p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities. p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities. p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively. p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively. p-Coumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=7400-08-0 (retrieved 2024-09-04) (CAS RN: 7400-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Luteolin

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

C15H10O6 (286.047736)


Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

   

Desaminotyrosine

3-(4-hydroxyphenyl)propanoic acid

C9H10O3 (166.062991)


Desaminotyrosine, also known as 4-hydroxyphenylpropionic acid, is a normal constituent of human urine. It is a product of tyrosine metabolism; its concentration in urine increases in patients with gastrointestinal diseases. Desaminotyrosine is a major phenolic acid breakdown product of proanthocyanidin metabolism (PMID:15315398). Urinary desaminotyrosine is produced by Clostridium sporogenes and C. botulinum (PMID:29168502). Desaminotyrosine is also found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas, and Staphylococcus (PMID:29168502, 28393285, 19961416). Desaminotyrosine is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain. A normal constituent of human urine. A product of tyrosine metabolism; concentration in urine increases in patients with gastrointestinal diseases. (Dictionary of Organic Compounds) May also result from phenolic acid metabolism by colonic bacteria. (PMID 15315398) [HMDB]. Phloretic acid is found in many foods, some of which are arrowroot, olive, avocado, and peanut. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling.

   

Acetosyringone

4 inverted exclamation mark -Hydroxy-3 inverted exclamation mark ,5 inverted exclamation mark -dimethoxyacetophenone

C10H12O4 (196.0735552)


Acetosyringone is a member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. It has a role as a non-steroidal anti-inflammatory drug, an anti-asthmatic drug, a non-narcotic analgesic, a peripheral nervous system drug and a plant metabolite. It is a member of acetophenones, a dimethoxybenzene and a member of phenols. Acetosyringone is a natural product found in Justicia adhatoda, Polyporus umbellatus, and other organisms with data available. Acetosyringone is a metabolite found in or produced by Saccharomyces cerevisiae. A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Annotation level-1 Acetosyringone is a phenolic compound from wounded plant cells, enables virA gene which encodes a membrane-bound kinase to phosphorylate itself and activate the virG gene product, which stimulates the transcription of other vir genes and itself[1]. Acetosyringone enhances efficient Dunaliella transformation of Agrobacterium strains[2]. Acetosyringone is a phenolic compound from wounded plant cells, enables virA gene which encodes a membrane-bound kinase to phosphorylate itself and activate the virG gene product, which stimulates the transcription of other vir genes and itself[1]. Acetosyringone enhances efficient Dunaliella transformation of Agrobacterium strains[2].

   

Chrysophanol

1,8-DIHYDROXY-3-METHYL-9,10-DIHYDROANTHRACENE-9,10-DIONE

C15H10O4 (254.057906)


Chrysophanic acid appears as golden yellow plates or brown powder. Melting point 196 °C. Slightly soluble in water. Pale yellow aqueous solutions turn red on addition of alkali. Solutions in concentrated sulfuric acid are red. (NTP, 1992) Chrysophanol is a trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity. It has a role as an antiviral agent, an anti-inflammatory agent and a plant metabolite. It is functionally related to a chrysazin. Chrysophanol is a natural product found in Rumex dentatus, Ageratina altissima, and other organisms with data available. See also: Frangula purshiana Bark (part of). A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity. Constituent of Rumex, Rheum subspecies Chrysophanol is found in dock, garden rhubarb, and sorrel. Chrysophanol is found in dock. Chrysophanol is a constituent of Rumex, Rheum species D009676 - Noxae > D009153 - Mutagens Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.

   

Knipholone

Knipholone

C24H18O8 (434.10016279999996)


An anthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 4 and 6, a methyl group at position 2 and a 3-acetyl-2,6-dihydroxy-4-methoxyphenyl group at position 1. It exhibits antioxidant, cytotoxic and antiplasmodial activities.

   
   

3-Methoxy-5-(prop-2-en-1-yl)benzene-1,2-diol

3-Methoxy-5-(prop-2-en-1-yl)benzene-1,2-diol

C10H12O3 (180.0786402)


   
   

Luteolin

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI)

C15H10O6 (286.047736)


Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

   

Knipholone anthrone

Knipholone anthrone

C24H20O7 (420.120897)


   
   
   

Chrysophanic acid

Chrysophanic acid

C15H10O4 (254.057906)


relative retention time with respect to 9-anthracene Carboxylic Acid is 1.321 D009676 - Noxae > D009153 - Mutagens relative retention time with respect to 9-anthracene Carboxylic Acid is 1.322 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.318 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.324 Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.

   

Vanillic Acid

Vanillic acid hexoside

C8H8O4 (168.0422568)


Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

   

Desaminotyrosine

3-(4-Hydroxyphenyl)propionic acid

C9H10O3 (166.062991)


Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling.

   

Hydroxycinnamic acid

Hydroxycinnamic acid

C9H8O3 (164.0473418)


The cis-stereoisomer of 3-coumaric acid.

   

Vanillate

4-Hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

   

Coumarate

InChI=1\C9H8O3\c10-8-4-1-7(2-5-8)3-6-9(11)12\h1-6,10H,(H,11,12)\b6-3

C9H8O3 (164.0473418)


D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants D000890 - Anti-Infective Agents p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities. p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities. p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively. p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively.

   

Crysophanol

Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)

C15H10O4 (254.057906)


D009676 - Noxae > D009153 - Mutagens Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.

   

Gaboroquinone A

Gaboroquinone A

C24H18O9 (450.0950778)


An anthraquinone that is anthracene-9,10-dione substituted by a 3-acetyl-4,6-dihydroxy-2-methoxyphenyl moiety at position 1, hydroxy groups at positions 4 and 5 and a hydroxymethyl group at position 2. Isolated from the roots of Bulbine frutescens, it exhibits antiplasmodial and antitrypanosomal activities.

   

4-O-demethylknipholone-4-O-beta-D-glucopyranoside

4-O-demethylknipholone-4-O-beta-D-glucopyranoside

C29H26O13 (582.1373346)


An anthraquinone that is knipholone in which the O-methyl group is replaced by a beta-D-glucopyranosyl group. It is isolated from the roots of Bulbine frutescens and exhibits trypanocidal and antiplasmodial activities.

   

(10r)-10-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,8,10-trihydroxy-3-methylanthracen-9-one

(10r)-10-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,8,10-trihydroxy-3-methylanthracen-9-one

C24H20O8 (436.115812)


   

1-(3-acetyl-2,6-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-2,6-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C29H26O13 (582.1373346)


   

(6s,9's)-1,1',4',5',6,9-hexahydroxy-2',6-dimethyl-5,7-dihydro-9'h-[2,9'-bianthracene]-8,10'-dione

(6s,9's)-1,1',4',5',6,9-hexahydroxy-2',6-dimethyl-5,7-dihydro-9'h-[2,9'-bianthracene]-8,10'-dione

C30H24O8 (512.1471104)


   

4,4',5,5'-tetrahydroxy-2,2'-dimethyl-[9,9'-bianthracenylidene]-10,10'-dione

4,4',5,5'-tetrahydroxy-2,2'-dimethyl-[9,9'-bianthracenylidene]-10,10'-dione

C30H20O6 (476.125982)


   

1,1',4',5',8-pentahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

1,1',4',5',8-pentahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

C30H20O8 (508.115812)


   

10-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,8,10-trihydroxy-3-methylanthracen-9-one

10-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,8,10-trihydroxy-3-methylanthracen-9-one

C24H20O8 (436.115812)


   

5,8-dihydroxy-1-(hydroxymethyl)naphtho[2,3-c]furan-4,9-dione

5,8-dihydroxy-1-(hydroxymethyl)naphtho[2,3-c]furan-4,9-dione

C13H8O6 (260.0320868)


   

(9's)-1',5-bis(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,4',5',8-tetrahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

(9's)-1',5-bis(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,4',5',8-tetrahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

C48H36O15 (852.2054105999999)


   

1,4',5',8,9'-pentahydroxy-2'-(hydroxymethyl)-6-methyl-[2,9'-bianthracene]-9,10,10'-trione

1,4',5',8,9'-pentahydroxy-2'-(hydroxymethyl)-6-methyl-[2,9'-bianthracene]-9,10,10'-trione

C30H20O9 (524.110727)


   

8-hydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione

8-hydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione

C13H8O4 (228.0422568)


   

(e)-4,4',5,5'-tetrahydroxy-2,2'-dimethyl-[9,9'-bianthracenylidene]-10,10'-dione

(e)-4,4',5,5'-tetrahydroxy-2,2'-dimethyl-[9,9'-bianthracenylidene]-10,10'-dione

C30H20O6 (476.125982)


   

1,5',8,10'-tetrahydroxy-2',6-dimethyl-[2,9'-bianthracene]-1',4',9,10-tetrone

1,5',8,10'-tetrahydroxy-2',6-dimethyl-[2,9'-bianthracene]-1',4',9,10-tetrone

C30H18O8 (506.10016279999996)


   

1-(3-acetyl-4,6-dihydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-4,6-dihydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C29H26O13 (582.1373346)


   

{8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

{8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

C15H10O6 (286.047736)


   

1-(3-acetyl-2,6-dihydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-2,6-dihydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C29H26O13 (582.1373346)


   

8-hydroxy-5-methoxy-1-methylnaphtho[2,3-c]furan-4,9-dione

8-hydroxy-5-methoxy-1-methylnaphtho[2,3-c]furan-4,9-dione

C14H10O5 (258.052821)


   

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4-hydroxy-2-methyl-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}anthracene-9,10-dione

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4-hydroxy-2-methyl-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}anthracene-9,10-dione

C36H38O18 (758.2058048)


   

4,5-dimethoxy-3-methyl-3h-naphtho[2,3-c]furan-1-one

4,5-dimethoxy-3-methyl-3h-naphtho[2,3-c]furan-1-one

C15H14O4 (258.0892044)


   

(3s)-4,5-dimethoxy-3-methyl-3h-naphtho[2,3-c]furan-1-one

(3s)-4,5-dimethoxy-3-methyl-3h-naphtho[2,3-c]furan-1-one

C15H14O4 (258.0892044)


   

(9's)-1,4',5',8-tetrahydroxy-2'-(hydroxymethyl)-6-methyl-9'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-[2,9'-bianthracene]-9,10,10'-trione

(9's)-1,4',5',8-tetrahydroxy-2'-(hydroxymethyl)-6-methyl-9'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-[2,9'-bianthracene]-9,10,10'-trione

C42H40O19 (848.216369)


   

5,8-dihydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione

5,8-dihydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione

C13H8O5 (244.0371718)


   

1-(3-acetyl-4,6-dihydroxy-2-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-4,6-dihydroxy-2-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C24H18O8 (434.10016279999996)


   

1-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C25H20O8 (448.115812)


   

1',5-bis(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,4',5',8-tetrahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

1',5-bis(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,4',5',8-tetrahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

C48H36O15 (852.2054105999999)


   

5-hydroxy-8-methoxy-1-methylnaphtho[2,3-c]furan-4,9-dione

5-hydroxy-8-methoxy-1-methylnaphtho[2,3-c]furan-4,9-dione

C14H10O5 (258.052821)


   

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4-hydroxy-2-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}anthracene-9,10-dione

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4-hydroxy-2-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}anthracene-9,10-dione

C36H38O18 (758.2058048)


   

1-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C23H16O8 (420.0845136)


   

4-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,8-dihydroxy-3-methyl-10h-anthracen-9-one

4-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-1,8-dihydroxy-3-methyl-10h-anthracen-9-one

C24H20O7 (420.120897)


   

(9'r)-1,4',5',8,9'-pentahydroxy-2',6-dimethyl-[2,9'-bianthracene]-9,10,10'-trione

(9'r)-1,4',5',8,9'-pentahydroxy-2',6-dimethyl-[2,9'-bianthracene]-9,10,10'-trione

C30H20O8 (508.115812)


   

1,4',5',8,9'-pentahydroxy-2',6-dimethyl-[2,9'-bianthracene]-9,10,10'-trione

1,4',5',8,9'-pentahydroxy-2',6-dimethyl-[2,9'-bianthracene]-9,10,10'-trione

C30H20O8 (508.115812)


   

1-(3-acetyl-2,4-dihydroxy-6-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-2,4-dihydroxy-6-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C24H18O8 (434.10016279999996)


   

(9's)-1,1',4',5',8-pentahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

(9's)-1,1',4',5',8-pentahydroxy-2',6-dimethyl-9'h-[2,9'-bianthracene]-9,10,10'-trione

C30H20O8 (508.115812)


   

(9's)-1,4',5',8,9'-pentahydroxy-2'-(hydroxymethyl)-6-methyl-[2,9'-bianthracene]-9,10,10'-trione

(9's)-1,4',5',8,9'-pentahydroxy-2'-(hydroxymethyl)-6-methyl-[2,9'-bianthracene]-9,10,10'-trione

C30H20O9 (524.110727)


   

{5,8-dihydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl (2e)-2-methylbut-2-enoate

{5,8-dihydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl (2e)-2-methylbut-2-enoate

C18H14O7 (342.0739494)


   

1,4',5',8-tetrahydroxy-2'-(hydroxymethyl)-6-methyl-9'-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-[2,9'-bianthracene]-9,10,10'-trione

1,4',5',8-tetrahydroxy-2'-(hydroxymethyl)-6-methyl-9'-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-[2,9'-bianthracene]-9,10,10'-trione

C42H40O19 (848.216369)


   

(9'r)-1,4',5',8,9'-pentahydroxy-2'-(hydroxymethyl)-6-methyl-[2,9'-bianthracene]-9,10,10'-trione

(9'r)-1,4',5',8,9'-pentahydroxy-2'-(hydroxymethyl)-6-methyl-[2,9'-bianthracene]-9,10,10'-trione

C30H20O9 (524.110727)


   

1,1',4',5',6,9-hexahydroxy-2',6-dimethyl-5,7-dihydro-9'h-[2,9'-bianthracene]-8,10'-dione

1,1',4',5',6,9-hexahydroxy-2',6-dimethyl-5,7-dihydro-9'h-[2,9'-bianthracene]-8,10'-dione

C30H24O8 (512.1471104)


   

1-(3-acetyl-4,6-dihydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

1-(3-acetyl-4,6-dihydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione

C29H26O13 (582.1373346)


   

{5,8-dihydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

{5,8-dihydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

C15H10O7 (302.042651)


   

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione

1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione

C24H18O9 (450.0950778)


   

{5,8-dihydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl 2-methylbut-2-enoate

{5,8-dihydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl 2-methylbut-2-enoate

C18H14O7 (342.0739494)