Molecular Structure of Guayulin A

Watkins, Steven F.; Fronczek, Frank R.; Chiari, G.; Reynolds, Gary W.; Rodriguez, Elroy

doi:10.1021/np50040a018

Cited by 18 publications

(6 citation statements)

References 11 publications

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“…The guayulin family of sesquiterpene secondary metabolites comprises four known members, guayulin A-D [1,2], although several other members may exist [3,4]. Guayulin A was first isolated in 1911 and its structure was determined some years later [5,6]. Guayulins consist of an isoprenoid nucleus, which may be partheniol, with a bicyclogermacrene structure (Guayulins A and B), or its derivative compound with an aromadendrene structure (Guayulins C and D) [7], esterified either by trans-cinnamic acid (Guayulins A and C), or p-anisic acid (Guayulins B and D) [3,4] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray)

Rozalén

García-Martínez

Carrión

et al. 2021

Plants

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The guayulins are a family of sesquiterpene compounds that consist of an isoprenoid nucleus substituted either by trans-cinnamic or p-anisic acid, and are present only in the resinous fraction of the rubber plant guayule (Parthenium argentatum, Gray). While the natural role of the guayulins remains enigmatic, they may serve as a defense function against other plants or herbivores by virtue of the accumulation of cinnamic acid. Prior research has suggested seasonal variation in guayulin content, which has been shown to decrease as winter arrives in two different varieties. In the present study, the effect of guayulins has been evaluated in 13 different accessions cultivated under the same conditions during autumn. A general reduction in guayulin content was found in the stems from all varieties between the September and November harvest, which was accompanied by an increase in the resin content. With respect to individual guayulins, while guayulin A was the most prominent member during most of the year, guayulin C had more prominence when temperature started to decrease. In this seasonal period, the production of each member of the guayulin family in the leaves was very balanced.

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Section: Introductionmentioning

confidence: 99%

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray)

Rozalén

García-Martínez

Carrión

et al. 2021

Plants

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“…Guayulins A and B are abundant in the resin. Namely, up to 10% of the resin mass is constituted of guayulin A [9][10][11], while the relevant amount of guayulin B in the resin from India is between 0.1% and 3% [10]. The wide variability in the amounts of guayulins A and B in the resin depends on a number of factors, such as: soil nature, climate, phenological phases, cultivar, age and, mainly, the nature of the different parts of the shrub [10,11].…”

Section: Introductionmentioning

confidence: 99%

Assessment, Validation and Application to Real Samples of an RP-HPLC Method for the Determination of Guayulins A, B, C and D in Guayule Shrub

et al. 2018

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Guayule (Parthenium argentatum Gray) is a shrub native to the arid regions of Mexico. In the last decades, significant attention to its cultivation has arisen because it is the raw material for the production of hypoallergenic natural rubber. Guayule biomass also contains high amounts of resin, which is not normally exploited in any way. Among other sesquiterpenic esters, guayulins (i.e., the parteniol esters of cinnamic acid, guayulin A, or of anisic acid, guayulin B) are contained in resin. In addition, minor amounts of guayulin C and guayulin D are formed by degradation/oxidation of guayulins A and B, respectively. Guayulins likely act as cinnamate and p-anisate reservoirs for the Guayule shrub; in addition, it has been postulated that they might have a key role in the chemical defense system of Guayule. Furthermore, it seems reasonable that guayulins may possess significant biological properties (e.g., antibacterial and anticancer activities), in close analogy with those shown by sesquiterpene lactones contained in many other species of Parthenum genus. As a matter of fact, guayulins A and B play an important role in the synthesis of antineoplastics used in breast cancer treatment. In this contribution we propose an original and validated RP-HPLC approach to the simultaneous quantification of guayulins A, B, C and D. The procedure of resin extraction from Guayule biomass has been optimized in terms of both extraction method and solvent. RP-HPLC separation has been accomplished by an Ascentis ® C18 column under isocratic elution with a 80:20 (v:v) acetonitrile:water mixture. Validation was carried out in terms of limits of detection and quantification, linearity, precision, and trueness. Finally, the method was tested with a number of fresh and seasoned samples of spontaneous Guayule shrub from Mexico.

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“…Before the breeding procedure, the resin content used to be about 40% of the rubber content, while after such a process, it increased up to 150% [14]. Sesqui-and tri-terpenes account for 37% and 52% of the resin produced by resin vessels [12] with the sesquiterpene, guayulin A, alone, accumulating to 1%-13.7% [15][16][17] depending on the variety and harvest date. Three other guayulins (B, C and D) occur in smaller amounts.…”

Section: Guayule: More Than Rubbermentioning

confidence: 99%

Potential Applications of Guayulins to Improve Feasibility of Guayule Cultivation

2019

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Guayule (Parthenium argentatum Gray) is an interesting alternative and renewable source of rubber/latex which has been used in the past. Guayule rubber and latex products are not available in the market largely because the raw material cost is higher than the current sources produced in South-East Asia and other tropical countries (Hevea brasiliensis). Guayule contains many other compounds whose joint exploitation could make guayule cultivation profitable, especially in semi-desert areas where cultivation of other crops is difficult or impossible. Guayulins A–D, sesquiterpene esters, appear to have some commercial promise. Despite being accumulated in relatively high concentrations (its majority representative, guayulin A, can account for up to 13.7% of the resin content of this plant, which itself ranges from 6%–12%), guayulins have received little direct attention from scientists. This review presents the current knowledge about the activity of these compounds and, based on known activities of similar compounds from other species, potential uses as fungicides, miticides and insecticides are suggested.

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Molecular Structure of Guayulin A

Cited by 18 publications

References 11 publications

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray)

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray)

Assessment, Validation and Application to Real Samples of an RP-HPLC Method for the Determination of Guayulins A, B, C and D in Guayule Shrub

Potential Applications of Guayulins to Improve Feasibility of Guayule Cultivation

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