Laurenene

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Laurenene
Laurenene.svg
Identifiers
PubChem CID
Properties
C20H32
Molar mass 272.48 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Laurenene is a diterpene natural product with an unusual [5.5.5.7]fenestrane structure. It was first discovered in extracts from the New Zealand tree species Dacrydium cupressinum by researchers at the University of Otago. [2] It has since been found in other species of New Zealand trees, such as Podocarpus totara . [3]

Diterpenes are a class of chemical compounds composed of two terpene units, often with the molecular formula C20H32. Diterpenes consist of four isoprene subunits. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and antiinflammatory.

Fenestrane

A fenestrane in organic chemistry is a type of chemical compound with a central quaternary carbon atom which serves as a common vertex for four fused carbocycles. They can be regarded as spiro compounds twice over. Because of their inherent strain and instability, fenestranes are of theoretical interest to chemists. The name—proposed in 1972 by Vlasios Georgian and Martin Saltzman—is derived from the Latin word for window, fenestra. Georgian had intended that "fenestrane" solely referred to [4.4.4.4]fenestrane, whose skeletal structure looks like windows, and Kenneth B. Wiberg called that specific structure "windowpane". The term fenestrane has since become generalized to refer to the whole class of molecules that have various other ring-sizes. Georgian recommended rosettane for the class, based on the structural appearance as a rosette of flowers.

<i>Dacrydium cupressinum</i> species of plant

Dacrydium cupressinum, commonly known as rimu, is a large evergreen coniferous tree endemic to the forests of New Zealand. It is a member of the southern conifer group, the podocarps. The former name "red pine" has fallen out of common use.

Related Research Articles

<i>Podocarpus totara</i> species of plant

Podocarpus totara is a species of podocarp tree endemic to New Zealand. It grows throughout the North Island and northeastern South Island in lowland, montane and lower subalpine forest at elevations of up to 600 m.

Podocarpaceae family of plants

Podocarpaceae is a large family of mainly Southern Hemisphere conifers, comprising about 156 species of evergreen trees and shrubs. It contains 19 genera if Phyllocladus is included and if Manoao and Sundacarpus are recognized.

<i>Podocarpus</i> genus of plants

Podocarpus is a genus of conifers, the most numerous and widely distributed of the podocarp family, Podocarpaceae. Podocarpus are evergreen shrubs or trees, usually from 1 to 25 metres tall, known to reach 40 metres (130 ft) at times. The cones have two to five fused cone scales which form a fleshy, berry-like, brightly coloured receptacle at maturity. The fleshy cones attract birds which then eat the cones and disperse the seeds in their droppings. There are approximately 97 to 107 species in the genus depending on the circumscription of the species.

<i>Nageia</i> genus of plants

Nageia is a genus of conifers belonging to the podocarp family Podocarpaceae. Nageia includes evergreen shrubs and trees, from one to 54 meters in height. A 2009 treatment of the genus recognized five species. Some authors consider Nageia formosensis to be a separate species from Nageia nagi, thus recognizing six species. The podocarp genera have been reshuffled by various botanists. Most recently, several species formerly classed as Nageia were moved to the new genus Retrophyllum, while Nageia falcata and Nageia mannii were moved to the new genus Afrocarpus.

<i>Podocarpus nubigenus</i> species of plant

Podocarpus nubigenus is a species of podocarp, endemic to the Valdivian temperate rain forests of southern Chile and adjacent southwestern Argentina. It is the southernmost podocarp in the world, It grows from 38° to Ultima Esperanza, It grows in wet and swampy soils. It can settle clear grounds, with a faster growth than the other Chilean podocarpaceae.

Copromorphidae, the "tropical fruitworm moths" is a family of insects in the lepidopteran order. These moths have broad, rounded forewings, and well-camouflaged scale patterns. Unlike Carposinidae the mouthparts include "labial palps" with the second rather than third segment the longest. With other unusual structural characteristics of the caterpillar and adult, it could represent the sister lineage of all other extant members of this superfamily. The genus Sisyroxena from Madagascar is also notable for its unusual venation and wing scale sockets.

Perenniporia podocarpi is a species of resupinate (encrusting) polypore. It occurs widely but uncommonly on the New Zealand endemic podocarps Dacrydium cupressinum and Prumnopitys taxifolia. Basidiocarps are dimitic and grow up to 9 cm across, thick and cushion-like with a distinctive white or very pale cream spore surface with large pores. The basidiospores are extremely large for the genus, up to 27 μm in length.

Podocarpus acutifolius Species of plant

Podocarpus acutifolius, commonly called needle-leaved tōtara, is a species of conifer in the Podocarpaceae family. It is found only in New Zealand. Its natural habitat is subtropical or tropical high-altitude shrubland. The specific epithet, acutifolius, meaning "thorny leaves", is derived from Latin acutus, and -folius (-leaved), and refers to the characteristic shape of the leaves.

<i>Podocarpus laetus</i> species of plant

Podocarpus laetus is a species of conifer in the Podocarpaceae family, commonly known as Hall's tōtara, mountain tōtara or thin-barked tōtara. Previously known as Podocarpus hallii and Podocarpus cunninghamii, in 2015 it was realised that the much earlier name P. laetus has priority.

<i>Podocarpus nivalis</i> species of plant

Podocarpus nivalis is a species of conifer in the Podocarpaceae family. It is endemic to New Zealand. It grows up to 5 m (16 ft) tall, and is found in the mountains and subalpine lands from 37° to the far south New Zealand.

<i>Harmonia antipoda</i> species of beetle

Harmonia antipoda, known as the antipodean ladybird, is a species of ladybird beetle indigenous to New Zealand. It occurs in forests on the North Island; they have been spotted on dead rimu trees, both on the leaves and under bark. They are a brown colour, and about 3 mm long. Another (non-native) species of the same genus also occurs in New Zealand, but is much larger and more conspicuously coloured.

<i>Pseudocoremia fenerata</i> species of insect

Pseudocoremia fenerata is a moth of the Geometridae family. It is endemic to New Zealand.

Totarol chemical compound

Totarol is a naturally produced diterpene that is bioactive as (+)-totarol. It was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand. Podocarpus totara was investigated for unique molecules due to the tree’s increased resistance to rotting. Recent studies have confirmed (+)-totarol’s unique antimicrobial and therapeutic properties. Consequently, (+)-totarol is a promising candidate for a new source of drugs and has been the goal of numerous syntheses.

<i>Isonomeutis amauropa</i> species of insect

Isonomeutis amauropa is a species of moth in the Copromorphidae family. It is endemic to New Zealand, where it is widespread and moderately common.

Robert Edward Corbett was a New Zealand organic chemist. He is noted for his contribution to natural product chemistry through the isolation and structural elucidation of compounds from New Zealand native plants.

References

  1. 1 2 "Laurenene". NIST.
  2. Corbett, R. Edward; Lauren, Denis R.; Weavers, Rex T. (1979). "The structure of laurenene, a new diterpene from the essential oil of Dacrydium cupressinum. Part 1". Journal of the Chemical Society, Perkin Transactions 1 : 1774–1790. doi:10.1039/P19790001774.
  3. Clarke, Don B.; Hinkley, Simon F.R.; Weavers, Rex T. (June 1997). "Waihoensene. A new laurenene-related diterpene from Podocarpus totara var waihoensis". Tetrahedron Letters . 38 (24): 4297–4300. doi:10.1016/S0040-4039(97)00884-8.