Diterpene

About: Diterpene is a research topic. Over the lifetime, 2586 publications have been published within this topic receiving 48162 citations. The topic is also known as: C20 isoprenoids & diterpenes.

Phytol, a Diterpene Alcohol from Chlorophyll, as a Drug against Neglected Tropical Disease Schistosomiasis Mansoni

Abstract: Background Schistosomiasis is a major endemic disease that affects hundreds of millions worldwide. Since the treatment and control of this parasitic disease rely on a single drug, praziquantel, it is imperative that new effective drugs are developed. Here, we report that phytol, a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties in vitro and in a mouse model of schistosomiasis mansoni. Methods and findings In vitro, phytol reduced the motor activity of worms, caused their death and confocal laser scanning microscopy analysis showed extensive tegumental alterations in a concentration-dependent manner (50 to 100 µg/mL). Additionally, phytol at sublethal doses (25 µg/mL) reduced the number of Schistosoma mansoni eggs. In vivo, a single dose of phytol (40 mg/kg) administered orally to mice infected with adult S. mansoni resulted in total and female worm burden reductions of 51.2% and 70.3%, respectively. Moreover, phytol reduced the number of eggs in faeces (76.6%) and the frequency of immature eggs (oogram pattern) was significantly reduced. The oogram also showed increases in the proportion of dead eggs. Confocal microcopy studies revealed tegumental damage in adult S. mansoni recovered from mice, especially in female worms. Conclusions The significant reduction in parasite burden by this chlorophyll molecule validates phytol as a promising drug and offers the potential of a new direction for chemotherapy of human schistosomiasis. Phytol is a common food additive and nonmutagenic, with satisfactory safety. Thus, phytol has potential as a safe and cost-effective addition to antischistosomal therapy.

The First Synthesis of a Daphnane Diterpene: The Enantiocontrolled Total Synthesis of (+)-Resiniferatoxin

Abstract: Resiniferatoxin (RTX,1) is a daphnane diterpene, identified in the latex of Euphorbia resiniferaon the basis of its extraordinary irritant activity. 1 While structurally related to the potent tumor-promoting phorbol esters, 2 RTX is not a tumor promoter 3 and does not compete for the phorbol ester binding site on protein kinase C. 4 It does, however, exhibit activity in common with capsaicin ( 2), the major active constituent of red peppers. 5 In addition to its widely appreciated culinary use, capsaicin is the active ingredient in several commercial analgesic formulations and is also of interest as an antinociceptive agent and antifeedant. 6 Exhibiting potencies 10 3 to 105 times greater than capsaicin in many assays, RTX itself is of special therapeutic interest as an analgesic agent, particularly for the treatment of pain associated with diabetic polyneuropathy and postherpetic neuralgia. 7 In addition, RTX and its analogs serve as key probes for biochemical investigations of the relatively little studied vanilloid receptor. 8 Notwithstanding the remarkably long (>2000 years) continuous therapeutic use of daphnane extracts, 5a the complexity and restricted availability of daphnanes and their analogs have greatly limited studies on their molecular mode of action. 9,10

Jatropha Diterpenes: a Review

Abstract: Terpenes are the largest group of phytochemicals that exhibit diverse functions in mediating antagonistic and beneficial interactions in, and among, organisms. For many years the abundance and distribution of terpenoid compounds in plants have benefitted both nature and human civilization. Jatropha species, belonging to the family Euphorbiaceae, are a rich source of terpenoid compounds. Among the terpenes, diterpenoid compounds have dominated the research area in Jatropha species with respect to their novel chemical structures and medicinal values. The present review describes the chemistry and biological activities of an array of Jatropha diterpenes. The diterpenes isolated from Jatropha species belongs to rhamnofolane, daphnane, lathyrane, tigliane, dinorditerpene, deoxy preussomerin and pimarane skeletal structures. Among the 68 diterpenes collated in this review, the biological activity of compounds varied distinctly—the majority of the diterpenes exhibited cytotoxic, antitumor and antimicrobial activities in vitro. To name a few, jatrophone, spruceanol and jatrophatrione exhibited antitumor properties against P338 lymphocytic leukemia and japodagrol against KB carcinoma cells. Whereas, curcusone B exhibited anti-invasive effects against cholangiocarcinoma cells. The phorbol esters (Jatropha factor C1–C6) and Jatropherol exhibited insect deterrent/cytotoxic properties. Many diterpenes (jatrophalactam, faveline derivatives, multifolone, curcusone, jatrophone derivatives etc.) showed in-vitro cytotoxic activity, while japodagrin, jatrogrossidione derivatives and jatropholone derivatives exhibited antimicrobial activities. Jatropha diterpenoids having a wide spectrum of bioactivity could form lead compounds or could be used as templates for the synthesis of new compounds with better biological activity for utilization in the pharmaceutical industries.

Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. II : Isolation of carnosic acid and formation of other phenolic diterpenes

Abstract: The phenolic diterpene carnosic acid appears to be the main substance for general oxidation leading to artifacts with gamma- or delta-lactone structure in extracts of Rosmarinus officinalis and Salvia officinalis. Until now it was only possible to prepare carnosic acid by hydrogenolysis of carnosol. A semipreparative HPLC method has been developed isolating carnosic acid among other phenolic diterpenes. The separated substances were identified by 13C-nuclear magnetic resonance (NMR), 1H-NMR, mass and IR spectroscopy. Conversion of carnosic acid and carnosol to other phenolic diterpenes was investigated by HPLC.