74299-48-2

Usage

Uses

Used in Pharmaceutical Industry:
Dehydrocostuslactone is used as a therapeutic agent for its anti-inflammatory, choleretic, anti-malarial, and antitumor effects, making it a potential candidate for the development of new drugs to treat various diseases.
Used in Cancer Treatment:
Dehydrocostuslactone is used as an antitumor agent, targeting various types of cancer. Its ability to modulate signaling pathways and exert antioxidant and anti-inflammatory effects contributes to its potential as a promising candidate in cancer therapy.
Used in Inflammatory Disorders:
Dehydrocostuslactone is used as an anti-inflammatory agent, helping in the treatment of various inflammatory disorders due to its capacity to modulate inflammatory pathways and reduce inflammation.
Used in Liver Diseases:
Dehydrocostuslactone is used as a choleretic agent, promoting bile flow and aiding in the treatment of liver diseases by improving bile secretion and reducing liver damage.
Used in Drug Discovery and Development:
Dehydrocostuslactone is used as a potential target in drug discovery and development, owing to its multifaceted biological activities and its ability to modulate various signaling pathways, making it a valuable compound for creating new therapeutic agents.

InChI:InChI=1/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1

Upstream product

• 90807-55-9 (3R,3aR,6aR,9aR,9bR)-3-Methyl-6,9-dimethylene-3-phenylselanyl-decahydro-azuleno[4,5-b]furan-2-one 
• 90548-06-4 watsonol A 
• 126209-82-3 saussureamine B 
• 308789-79-9 [((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-acetic acid 
• 308789-82-4 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-3-hydroxy-propionic acid 
• 301301-14-4 (R)-2-Amino-3-((3S,3aS,6aR,9aR,9bS)-6,9-dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethylsulfanyl)-propionic acid 
• 308789-80-2 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-4-methyl-pentanoic acid 
• 308789-83-5 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-4-methylsulfanyl-butyric acid 
• 308789-81-3 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-3-phenyl-propionic acid 
• 308789-77-7 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-5-guanidino-pentanoic acid 
• 60134-10-3 1-oxo-eudesm-2,4(15)-dien-5α,6β,7α,11βH-12,6-olide 
• 32223-12-4 11β,13-dihydroreynosin 
• 58698-14-9 1-oxo-Δ²-santenolide 
• 4955-03-7 11β,13-dehydrocostuslactone 

Downstream Products

• 142506-58-9 5α-hydroxy-isozaluzanin C 
• 16838-87-2 3α-hydroxyguaia-4(15),10(14),11(13)-trien-6,12-olide 
• 130518-92-2 (3aS,9bS)-6,9-Dimethylene-3-(2-oxo-propyl)-decahydro-azuleno[4,5-b]furan-2-one 
• 22419-86-9 (3R)-6,9-bis-methylene-(3rN,3at,6at,9at,9bc)-Δ^1'-dodecahydro-spiro[azuleno[4,5-b]furan-3,3'-pyrazol]-2-one 
• 68151-26-8 isodehydrocostus lactone 
• 143246-39-3 4α-Methoxydehydrocostus lactone 
• 143246-38-2 4β-Methoxydehydrocostus lactone 
• 142138-73-6 13-Benzoylcostuslactone 
• 67667-64-5 3α-hydroxyguaia-4(15),10(14),11(13)-trien-12,6-olide 
• 106533-13-5 13-hydroxycostuslactone 
• 142138-71-4 (3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-3-(2-oxo-propyl)-decahydro-azuleno[4,5-b]furan-2-one 
• 142138-72-5 (3R,3aS,6aR,9aR,9bS)-3-(2-Hydroxy-propyl)-6,9-dimethylene-decahydro-azuleno[4,5-b]furan-2-one 
• 126209-82-3 saussureamine B 
• 213821-55-7 C₁₅H₁₈O₃ 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of (?)-Dehydrocostus Lactone by Domino Metathesis

An efficient total synthesis of the sesquiterpenoid (?)-dehydrocostus lactone is reported. Our earlier approach by a domino enediyne metathesis was extended by a domino dienyne metathesis strategy to give access to suitably functionalized hydroazulene cores. Highly stereoselective asymmetric anti aldol reactions provided the enantiopure substrates for this key step of our synthesis. Multiple hydroboration/oxidation of the resulting hydroazulenes set up three out of four stereogenic centers in a single step. First, oxidation to give a diketo-γ-lactone enabled an enantioselective formal synthesis of the target guaianolide. Subsequently, the final steps of this approach were improved by using a double carbonyl olefination at the stage of a masked γ-butyrolactone, which completed the synthesis in a much more efficient way.

Enantioselective Total Synthesis of the Guaianolide (-)-Dehydrocostus Lactone by Enediyne Metathesis

The hydroazulene core of the bioactive sesquiterpenoid (-)-dehydrocostus lactone was generated by domino enediyne metathesis. A triple hydroboration/oxidation of the resultant conjugated triene installed three out of four stereogenic centers of the target in a single step. The enantiopure acyclic metathesis substrate was readily available by an asymmetric anti aldol reaction. Masking of the O-lactone as an acetal allowed for an efficient completion of the synthesis through late-stage double carbonyl olefination.

Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa

From the methanolic extract of the dried roots of Saussurea lappa Clarke, Saussureae Radix, five amino acid-sesquiterpene conjugates, saussureamines A, B, C, D and E, were isolated together with a lignan glycoside, (-)-massoniresinol 4-O-β-D-glucopyranoside. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, saussureamines and the related amino acid-sesquiterpene conjugates were synthesized using a Michael type addition reaction of amino acid to the α-methylene-γ-lactone moiety of sesquiterpenes. Saussureamines A, B and C, costunolide and dehydrocostus lactone showed a gastroprotective effect on acidified ethanol-induced gastric mucosal lesions in rats. Saussureamines A also exhibited an inhibitory effect on gastric mucosal lesions induced by water-immersion stress in mice. (C) 2000 Elsevier Science Ltd.

Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives

The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from l-α- santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an α-methylene γ- lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.

GUAIANE SESQUITERPENES FROM MAGNOLIA WATSONII

The leaves and the trunk barks of Magnolia watsonii afforded two biosynthetic intermediates of dehydrocostuslactone (watsonol A and watsonol B) along with the neolignans, magnolol, honokiol and obovatol, and the aporphine alkaloids, liriodenine and asimilobine.Key Word Index - Magnolia watsonii; Magnoliaceae; sesquiterpenes; dehydrocostuslactone; watsonol A; watsonol B; 15-acetoxycostunolide; neolignans; obovatol; aporphine alkaloids.

TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN

A series of guaianolides such as mokko lactone, dehydrocostus lactone, and eremanthin which posses a common structural unit in A ring have been synthesized from 1-oxoeudesm-2-eno-13,6α-lactone in 7 steps.The key step involves solvolytic rearrangement of 1β-mesyloxyeudesm-4(14)-eno-13,6α-lactone.