germacranolide
Identification
| Name | germacranolide |
| IUPAC | (3S,3aR,4S,5Z,7S,10Z,11aR)-4,7-dihydroxy-3,6,10-trimethyl-3a,4,7,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one |
| Molecular Formula | C15 H22 O4 |
| Molecular Weight | 266.33714000 |
| Nikkaji Number | J445.275E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1144 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for germacranolide usage levels up to | not for fragrance use. |
| Recommendation for germacranolide flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(3S,3aR,4S,5Z,7S,10Z,11aR)-4,7-
dihydroxy-3,6,10-trimethyl-3a,4,7,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
PubMed:
Layer chromatography-bioassays directed screening and identification of antibacterial compounds from Scotch thistle.
PubMed:
Anti-inflammatory and immunomodulatory activities of Inula cappa roots (Compositae).
PubMed:
Three new elemanolides from the seeds of Vernonia anthelmintica.
PubMed:
Antiplasmodial Sesquiterpenoid Lactones from Trichospira verticillata: Structure Elucidation by Spectroscopic Methods and Comparison of Experimental and Calculated ECD Data.
PubMed:
Investigation of the Anti-Leishmania (Leishmania) infantum Activity of Some Natural Sesquiterpene Lactones.
PubMed:
Heme-binding activity of methoxyflavones from Pentzia monodiana Maire (Asteraceae).
PubMed:
Antiprotozoal Activity-Based Profiling of a Dichloromethane Extract from Anthemis nobilis Flowers.
PubMed:
Isolation, Structure Elucidation, and Absolute Configuration of Highly Oxygenated Germacranolides from Carpesium cernuum.
PubMed:
A sesquiterpene lactone from Siegesbeckia glabrescens suppresses Hedgehog/Gli-mediated transcription in pancreatic cancer cells.
PubMed:
Bioherbicidal activity of a germacranolide sesquiterpene dilactone from Ambrosia artemisiifolia L.
PubMed:
The germacranolide sesquiterpene lactone neurolenin B of the medicinal plant Neurolaena lobata (L.) R.Br. ex Cass inhibits NPM/ALK-driven cell expansion and NF-κB-driven tumour intravasation.
PubMed:
Melampodium leucanthum, a source of cytotoxic sesquiterpenes with antimitotic activities.
PubMed:
Centrifugal partition chromatography elution gradient for isolation of sesquiterpene lactones and flavonoids from Anvillea radiata.
PubMed:
Vibrational circular dichroism (VCD), VCD exciton coupling, and X-ray determination of the absolute configuration of an α,β-unsaturated germacranolide.
PubMed:
Antiproliferative activity of Artemisia asiatica extract and its constituents on human tumor cell lines.
PubMed:
Germacranolides and their diversity of Eupatorium heterophyllum collected in P. R. China.
PubMed:
New sesquiterpenic acids from Inula wissmanniana.
PubMed:
Effect of different types of sesquiterpene lactones on the maturation of Rhinella arenarum oocytes.
PubMed:
Isolation, characterization, and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae.
PubMed:
Sesquiterpenes from Neurolaena lobata and their antiproliferative and anti-inflammatory activities.
PubMed:
Antiprotozoal screening of 60 South African plants, and the identification of the antitrypanosomal germacranolides schkuhrin I and II.
PubMed:
Secondary metabolites from the aerial parts of Centaurea pannonica (Heuff.) Simonk. from Serbia and their chemotaxonomic importance.
PubMed:
In-silico Leishmania target selectivity of antiparasitic terpenoids.
PubMed:
New eudesmenoic acid methyl esters from the seed oil of Jatropha curcas.
PubMed:
Trilobolide and related sesquiterpene lactones from Laser trilobum possessing immunobiological properties.
PubMed:
Cytotoxic and NF-κB inhibitory sesquiterpene lactones from Piptocoma rufescens.
PubMed:
Sesquiterpene lactones from Inula hupehensis inhibit nitric oxide production in RAW264.7 macrophages.
PubMed:
A new sesquiterpene lactone from Elephantopus tomentosus.
PubMed:
Screening and HPLC-Based Activity Profiling for New Antiprotozoal Leads from European Plants.
PubMed:
Sesquiterpenes and other constituents from Dendranthema zawadskii var. latilobum.
PubMed:
Discovery of GABA(A) receptor modulator aristolactone in a commercial sample of the Chinese herbal drug "Chaihu" (Bupleurum chinense roots) unravels adulteration by nephrotoxic Aristolochia manshuriensis roots.
PubMed:
Biotransformation of germacranolide from Onopordon leptolepies by Aspergillus niger.
PubMed:
A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima.
PubMed:
A germacranolide sesquiterpene lactone suppressed inducible nitric oxide synthase by downregulating NF-κB activity.
PubMed:
An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatoriumperfoliatum.
PubMed:
Antileishmanial Germacranolides from Calea zacatechichi.
PubMed:
Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide.
PubMed:
Cytotoxic germacranolide sesquiterpenes from the bark of Magnolia kobus.
PubMed:
Differential proteomic profiling identifies novel molecular targets of paclitaxel and phytoagent deoxyelephantopin against mammary adenocarcinoma cells.
PubMed:
Chemical and biomolecular characterization of Artemisia umbelliformis Lam., an important ingredient of the alpine liqueur "Genepi".
PubMed:
Biogenesis of sesquiterpene lactones pseudoguaianolides from germacranolides: theoretical study on the reaction mechanism of terminal biogenesis of 8-epiconfertin.
PubMed:
Chemical constituents and pharmacological properties of Radix Inulae.
PubMed:
Sesquiterpene lactones from Staehelina fruticosa.
PubMed:
Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity.
PubMed:
Cytotoxic germacranolide sesquiterpene from Inula cappa.
PubMed:
Cytotoxic germacranolide sesquiterpene lactones from Carpesium triste var. manshuricum.
PubMed:
Cytotoxic germacranolides and acyclic diterpenoides from the seeds of Carpesium triste.
PubMed:
Quantitative estimation of parthenolide in Tanacetum parthenium (L.) Schultz-Bip. cultivated in Egypt.
PubMed:
A new germacranolide-type sesquiterpene lactone from Tanacetum santolinoides.
PubMed:
Isolation and identification of antiplasmodial sesquiterpene lactones from Oncosiphon piluliferum.
PubMed:
Sesquiterpene lactones from Dimerostemma species (Asteraceae) and in vitro potential anti-inflammatory activities.
PubMed:
Hepatoprotective sesquiterpene glycosides from Sarcandra glabra.
PubMed:
Sesquiterpene lactones from Achillea collina J. Becker ex Reichenb.
PubMed:
Highly oxygenated guaianolides and eudesman-12-oic acids from Balsamorhiza sagittata and Balsamorhiza macrophylla.
PubMed:
Inhibition of preadipocyte differentiation by germacranolides from Calea urticifolia in 3T3-L1 cells.
PubMed:
A potent apoptosis-inducing activity of a sesquiterpene lactone, arucanolide, in HL60 cells: a crucial role of apoptosis-inducing factor.
PubMed:
Germacranolides from Anvillea radiata.
PubMed:
New sesquiterpene dilactones from Mikania micrantha.
PubMed:
NMR and x-ray conformational study of artemisiifolin and three other related germacranolides.
PubMed:
Germacrane derivatives from Santolina pinnata subsp. neapolitana.
PubMed:
Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells.
PubMed:
Biosynthesis of anthecotuloide, an irregular sesquiterpene lactone from Anthemis cotula L. (Asteraceae) via a non-farnesyl diphosphate route.
PubMed:
cis,cis-Germacranolides and melampolides from Mikania thapsoides.
PubMed:
Antibacterial evaluation of cnicin and some natural and semisynthetic analogues.
PubMed:
Terpenes from Inula verbascifolia.
PubMed:
The effect of sesquiterpene lactones on the release of human neutrophil elastase.
PubMed:
Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group.
PubMed:
Seven germacranolides, eupaglehnins A, B, C, D, E, and F, and 2alpha-acetoxyepitulipinolide from Eupatorium glehni.
PubMed:
Potentiation of 1,25-dihydroxyvitamin D(3)-induced differentiation of human promyelocytic leukemia cells into monocytes by costunolide, a germacranolide sesquiterpene lactone.
PubMed:
Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory.
PubMed:
Germacranolides from Artemisia myriantha and their conformation.
PubMed:
Chemistry of New Zealand Apiaceae: a rare phenylpropanoid and three new germacrane derivatives from Anisotome lyallii.
PubMed:
A highly substituted germacranolide from Leontodon cichoraceus.
PubMed:
Sesquiterpene lactones of Centaurea scoparia.
PubMed:
A germacranolide and three hydroxybenzyl alcohol derivatives from Hieracium murorum and Crepis bocconi.
PubMed:
Inhibition of inflammatory cytokine production and lymphocyte proliferation by structurally different sesquiterpene lactones correlates with their effect on activation of NF-kappaB.
PubMed:
Microbial transformation of pyrethrosin.
PubMed:
A new germacranolide from Artemisia pallens.
PubMed:
Germacranolides from Mikania guaco.
PubMed:
Guaiane dimers and germacranolide from Artemisia caruifolia.
PubMed:
Germacranolides and a new type of guaianolide from Acanthospermum hispidum.
PubMed:
Sesquiterpenoids and phenolics from Crepis mollis.
PubMed:
Further sesquiterpene lactones from Anthemis carpatica.
PubMed:
Fungicidal activity of natural and synthetic sesquiterpene lactone analogs.
PubMed:
Sesquiterpene lactones with potential use as natural herbicide models (I): trans,trans-germacranolides.
PubMed:
Mono- and sesquiterpenes and antifungal constituents from Artemisia species.
PubMed:
Antimycobacterial evaluation of germacranolides.
PubMed:
Four new cytotoxic germacranolides from Carpesium divaricatum.
PubMed:
Sesquiterpene lactone containing Mexican Indian medicinal plants and pure sesquiterpene lactones as potent inhibitors of transcription factor NF-kappaB.
PubMed:
Antiplasmodial activities and cytotoxic effects of aqueous extracts and sesquiterpene lactones from Neurolaena lobata.
PubMed:
Conformational analysis and biological activity of leptocarpin and leptocarpin acetate.
PubMed:
A bioassay for inhibition of serotonin release from bovine platelets.
PubMed:
Constituents of Michelia Rajaniana. Two new germacranolide amides.
PubMed:
Constituents of Paramichelia baillonii: a new antitumor germacranolide alkaloid.
PubMed:
Bisabolone derivatives and sesquiterpene lactones from centaurea species.
PubMed:
Molecular recognition patterns of sesquiterpene lactones in costus-sensitive patients.
PubMed:
Antitumor agents, 71. Nudaphantin, a new cytotoxic germacranolide, and elephantopin from Elephantopus nudatus.
PubMed:
Structure revision and cytotoxicity of the germacranolide, stizolicin, from Stizolophus balsamitus (Asteraceae).
PubMed:
Germacranolide, Hydroxyverbenon und ent-Kaur-15(16)-en-17,19-disäure aus Helianthus occidentalis var. dowellianus.
PubMed:
Sesquiterpene Lactones from Aegialophila pumila.
PubMed:
The effect of sesquiterpene lactones, eupatoriopicrin and hydroxyisonobilin, on the glycolytic metabolism of human lymphocytes.
PubMed:
Antitumor agents LII: The effects of molephantinin on nucleic acid and protein synthesis of Ehrlich ascites cells.
PubMed:
Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L.
PubMed:
Neutron diffraction structure of melampodin: its role in the reclassification of the germacranolides.
PubMed:
Antitumor agents. II. Tulipinolide, a new germacranolide sesquiterpene, and constunolide. Two cytotoxic substances from Liriodendron tulipifera L.