Sesquiterpene esters

Separation methods, multichromato-graphic la 56 Serine la 246,356 lb 132 Serotonin la 70,76,239,240,262,355, 380 lb 37-39,231,243,348 Serotonin metabolites lb 327 Serum lipids la 89 Serum proteins la 74 Sesquiterpene derivatives lb 239,446 Sesquiterpene esters lb 239 Sesquiterpene glucosides la 327 Sesquiterpene lactones lb 448 Sevin lb 387-389 Si 50 000, specific surface area la 91 Silica gel, caffeine-impregnated la 85 -, surface modified la 3 Silica gel 60, specific surface area la 91... 

The aroma of intact black currant fruit is mostly produced by anabolic pathways of the plant, and production of fruit volatiles occurs mainly during a short ripening period [112]. The aroma profile of black currant shares similarities with that of other berry fruits, although terpenes are more abundantly present in black currant [107]. Black currant is mainly used for the production of juice. Over 150 volatile compounds have been reported from either black currant berries and/or juice, of which the major groups are monoterpenes, sesquiterpenes, esters and alcohols [107]. Processing of berries to juice has been shown to lead to major changes in the aroma composition [113-118]. 

Sesquiterpene esters based on the dihydro-agarofuran moiety occur mainly within the Celastra-ceae family. The basic polyhydroxy skeleton vary according to the position, number and configuration of the ester residues in the dihydro- 3-agarofuran sesquiterpene. 

Sesquiterpene esters Echi nadiol-, epoxyechin adiol-echinaxantliol- and dihydroxynardol-dnnamale Caffeic acid derivatives... 

Table 6 shows the eleven sesquiterpene esters of aristolochic acids isolated from Aristolochia species. Isolation of the aristoloterpenate I (40) from the radix of A. mollissima is the first report of such compounds in... 

A. heterophylla [249,251] and a diterpene ester of aristolochic acid from the roots and stems of A. elegans [252] and thus, A. heterophylla is considered to be a rich source of sesquiterpene esters of aristolochic acids. Aristoloterpenate I (40) and III (42) are esters of aristolochic acid I (5) with the sesquiterpenes, madolin M (305) and L (306), respectively, whereas aristoloterpenate II (39) and IV (41) are esters of aristolochic acid II (1) [249]. In these four esters C-ll of the aristolochic acid and C-4 of sesquiterpene were involved in the ester linkage. The stereochemistry at... 

Recently, a paper appeared which reported the isolation of two new sesquiterpene esters I (R = isovaleryl, 2-methylbutryl) from Trisis Parodoxa. These two compounds as well as two other sesquiterpene lactones reported,extend further the list of natural isocedrene derivatives. ... 

The Celastraceae family is a rich source of sesquiterpene esters based on the dihydro-3-agarofuran [5,11-epoxy-5P,10a-eudesm-4(14)-ene] skeleton, and they are considered to be chemotaxonomic indicators of the family [6]. X-ray data and a conformational study by molecular mechanics showed that in every instance with only slight variations, the rraw-fiised A and B rings formed a chair-chair decalin system, slightly distorted by the presence of the 1,3-diaxial bond responsible for the tetrahydrofuran C ring, practically perpendicular to the plain formed by carbons C-5, C-7, C-8 and C-10, Fig. (1). 

Juvebione, paper factor a monocyclic sesquiterpene ester from the wood of the North American balsam fir (Abies balsamea). (-h)-J. is an oil, M, 266, [a] +79.5° (c = 3.5, CHCI3). J. was the first juvenile hormone isolated from a plant, and its structure was the first elucidated. It is specific for Pyrrhocoris apterus and only the dextrorotatory form is biologically active. The search for J. began when it was observed that filter paper made from the wood of the balsam fir contained a factor which produced developmental anomalies in the larvae of Pyrrhocoris. In addition to... 

Echinacea purpurea roots have been substituted for a long time with Partheni-um integrifolium. The sesquiterpene esters, echinadiol-, epoxyechinadiol-, echinax-anthol- and dihydroxy-nardol-cinnamate, described as constituents of Echinacea purpurea roots [81], were in fact derived from the adulterant Parthenium integri-folium which was mistakenly processed at that time. Since both species contain different constituents, HPLC and TLC methods have been developed to distinguish them [32]. Parthenium integrifolium is characterized by the sesquiterpene esters (Fig. 10) which cannot be found in Echinacea roots. 

Bauer R, Khan lA, hotter H, Wagner H, Wray V (1985) Structure and stereochemistry of new sesquiterpene esters from Echinacea purpurea (L.) MOENCH. Helv Chim Acta 68 2355-2358... 

The oil contains methyl-nonyl-ketone, and, probably, decyl aldehyde-Dipentene, linalol, a sesquiterpene, esters, and the lactone xanthotoxin were also isolated from the oil. 

Misidentification of source plants involved in chemical analysis before 1986, except for authenticated cultivated E. purpurea, renders earlier chemical studies unreliable. Components attributed to E. angustifolia, which may instead have involved E. pallida, include flavonoid components of the leaves essential oil constituents, including echinolone, humu-lene, caryophyllene epoxide, and various polyacetylene components. Four sesquiterpene esters (cinnamates of echinadiol, epox-yechinadiol, echinaxanthol, and dUiydroxy-nardol) attributed to E. purpurea in fact do not occur in Echinacea but are constituents of Parthenium integrifolium. Chemical work by R. Bauer and coworkers at Munich and Diisseldorf now makes distinction of source species in commercial supplies possible. 

In this chapter we will take a look at several syntheses of a sesquiterpene ester called juvabione. We will see that it became a target for synthesis because of structural and biological issues, and became a test molecule for the evaluating methodology for controlling vicinal stereochemistry in acyclic systems. But first let s once again examine the steroid sidechain problem. 

Mori, K. Matsui, M. "Synthesis of d/-Juvabione (Methyi c//-Todomatuate), A Sesquiterpene Ester with Juveniie Hormone Activity" Tetrahedron Lett. 1967, 2515-2518. 

Three chlorinated derivatives, chloriolins A-C, were isolated from cultures of an unidentified fimgus harvested from the sponge Jaspis cf johnstoni. Chloriolins B and C are sesquiterpene esters which have the tricyclic skeleton of hirsutane, of which chloriolin A is a degraded bicyclic form (Cheng et al, 1994). 

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