(-)-Falcarinol

244.37200

244.37

DTXSID50415266

2905290000

20.23000

3.84690

0.931g/cm3

115 °C @ Press: 0.02 Torr

163.4ºC

1.507

5.3E-07mmHg at 25°C

Even in low concentrations (0.03%), ... falcarinol elicited strong reactions...|In a human maximization test of 5% falcarinol ... 10 of 20 subjects were sensitized. No subjects gave irritant reactions to 5%, 10 became sensitive to 1%, and 7 to 0.05%, with 3 of these giving 3+ to 4+ bullous reactions.|Falcarinol, but not falcarindiol, falcarinone and dehydrofalcarinone, elicited allergic contact dermatitis in a 38-year-old female plant-nursery worker.

/OTHER TERRESTRIAL SPECIES/ ...Falcarinol and some alcohols, terpenes, furan derivatives, and paraffins have been isolated from the essential oil /of the Calycotome villosa (Poiret) Link leaf/. Thirteen alkaloids and falcarinol have been identified in the chloroform fraction of the basic methanol extract. Six flavonoids and four anthraquinones have been isolated in the chloroform fraction after acidification of the basic methanol extract. The cytotoxic and antimicrobial activities have also been evaluated. The essential oil, the methanol extract in toto, and the fraction of the basic extract showed strong cytotoxicity, whereas the fraction of the acid extract showed lower cytotoxicity. Furthermore, this fraction showed good antibacterial activity against Staphylococcus aureus, Bacillus lentus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Providencia rettgeri, and Morganella morganii. It can therefore be stated that this plant's cytotoxicity is prevalently due to falcarinol.

Besides Panax ginseng and Schefflera arboricola, ... / common ivy (Hedera helix susp. helix)/ is the third species of the Araliaceae in which these polyacetylenic sensitizers have been found.|From the plant Schefflera arboricola, which has been reported to cause allergic contact dermatitis, we have isolated and determined the elicitor of allergic contact dermatitis as falcarinol, heptadeca-1,9(Z)-diene-4,6-diyne-3-ol.|Experimental and chemical investigations revealed that common ivy (Hedera helix susp. helix) contains 3 compounds which are powerful irritants and moderate sensitizers. Only 2 of these constituents, falcarinol and didehydrofalcarinol, are present in the plant during the whole year. Besides Panax ginseng and Schefflera arboricola, this is the third species of the Araliaceae in which these polyacetylenic sensitizers have been found. Falcarinol and didehydrofalcarinol also occur in Hedera helix subsp. canariensis.

Ethanolic extracts from 10 Chinese herbs /were tested/ for their effects on K562, Raji, Wish, HeLa, Calu-1, and Vero tumor cells proliferation. On a percentage basis, panaxynol purified from Saposhnikovae divaricata had the highest inhibitory activity on various tumor cells proliferation. Cell-cycle analysis indicated that panaxynol arrested the cell cycle progression of tumor cells from the G1 transition to the S phase. In an attempt to further localize the point in the cell cycle where arrest occurred, gene expression of cyclin E, a key regulatory event leading to the G1/S boundary was examined. Results indicated that the levels of cyclin E mRNA in various tumor cells were decreased by panaxynol. Thus, the suppressant effects of panaxynol on proliferation of various tumor cells appeared to be mediated, at least in part, through impairments of cyclin E mRNA levels and arresting cell cycle progression in the cells.

Basic Treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation at the first sign of upper airway obstruction may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/

/HUMAN EXPOSURE STUDIES/ Skin: From the plant Schefflera arboricola, which has been reported to cause allergic contact dermatitis, ... the elicitor of allergic contact dermatitis /was isolated and determined to be/ falcarinol, heptadeca-1,9(Z)-diene-4,6-diyne-3-ol. Three polyacetylenes closely related to falcarinol, namely falcarindiol, falcarinone and dehydrofalcarinone were tested simultaneously. Falcarinol, but not falcarindiol, falcarinone and dehydrofalcarinone, elicited allergic contact dermatitis in a 38-year-old female plant-nursery worker.|/HUMAN EXPOSURE STUDIES/ Experimental and chemical investigations revealed that common ivy (Hedera helix susp. helix) contains 3 compounds which are powerful irritants and moderate sensitizers. Only 2 of these constituents, falcarinol and didehydrofalcarinol, are present in the plant during the whole year. Besides Panax ginseng and Schefflera arboricola, this is the third species of the Araliaceae in which these polyacetylenic sensitizers have been found. Falcarinol and didehydrofalcarinol also occur in Hedera helix subsp. canariensis. 4 patients have been patch tested. Even in low concentrations (0.03%), the main allergen falcarinol elicited strong reactions in all of them. One of the authors became sensitized during the investigations.|/HUMAN EXPOSURE STUDIES/ In a human maximization test of 5% falcarinol isolated from Hedera helix, 10 of 20 subjects were sensitized. No subjects gave irritant reactions to 5%, 10 became sensitive to 1%, and 7 to 0.05%, with 3 of these giving 3+ to 4+ bullous reactions.|/SPECIAL STUDIES/ The anti-proliferative effects of lipid soluble Panax ginseng components on human renal cancer cell lines /were investigated/. Petroleum ether extract of Panax ginseng roots (GX-PE) or its partially purified preparation (7:3 GX) was added to cultures of three human renal cell carcinoma (RCC) cell lines, A498, Caki-1, and CURC II. Proliferation of RCC cells was estimated by a [3H]thymidine incorporation assay and cell cycle distribution was analyzed by flow cytometry. GX-PE, 7:3 GX, panaxydol and panaxynol inhibited proliferation of all three RCC cell lines in a dose dependent manner in vitro with an order of potency, 7:3 GX >panaxydol >panaxynol =GX-PE. Additive effect of interleukin 4 was also demonstrated, most prominently in Caki-1 which responded poorly to GX-PE alone. Analysis of cell cycle in CURC II and Caki-1 treated with GX-PE demonstrated increase in G1 phase population and corresponding decrease in S phase population. The present study demonstrated that proliferation of human RCC cell lines were inhibited by lipid soluble components of Panax ginseng roots by blocking cell cycle progression at G1 to S phase transition.

falcarinol

Falcarinol is an allergen.|Falcarinol is found in english ivy which causes contact dermatitis.