Phenolic triterpenoids

Resins older than 40 000 years are considered to be fossil resins. The fossilization of resins begins with polymerisation and forms ambers and copals. Most of the ambers are derived from components of diterpenoid resins with a labdanoid structure other ambers are based on polymers of sesquiterpene hydrocarbons such as cadinene, and may include triterpenoids less common ambers from phenolic resins derive from polymers of styrene. Figure 1.4 shows the skeletal structures of the components which make up the polymers occurring in fossil resins [141]. 

The result obtained by GC-MS, with the same SPME conditions, from the black thick balm of a crocodile mummy (sample 1400, Musee Guimet, Lyon, France) is presented in Figure 10.11. The composition of the extract is close to that of sample 1998 but phenolic compounds were not detected. The GC-MS chromatogram obtained with the same substance after acid methanolysis and silylation is presented in Figure 10.12. Except for the sesquiterpenoids eluted between 10 min and 22 min, the observed compounds originate from a beeswax. The biomarkers of this substance are hexadecanoic acids hydroxylated in position 14 or 15 and long chain hydrocarbons, acids and alcohols eluted between 50 min and 90 min. Diterpenoid or triterpenoid resin components are not observed. 

Trisulfuric acid, 23 765 Tris[(dimethylamino)methyl]phenol, 1 536 Tri-t-butoxyalumino hydrides, 13 624 Triterpenoids, 24 555-557 Trithia[9]crown-3, 24 41 Trititanium pentoxide, 25 14... 

N.A. Iridoid glycosides, flavonol glycosides, coumarins, phenolic acids, sterols, triterpenoids, tannins." Stimulate digestive secretions, treat fluid retention, scabies, and fever. 

N.A. Triterpenoid saponins, flavonoids, phenols, tannins, volatile oil. Internally for bronchitis, respiratory tract infections, insomnia, anxiety, rheumatic disorders. 

N.A. Polygala senega L. Triterpenoid saponins, phenolic acids, polygalitol, methyl salicylate, sterols.99 103 291 292 Treat rattlesnake bite, cough, bronchitis, asthma. 

Nomura T and Fukai T (1998) Phenolic constituents of licorice (Glycyrrhiza species). Prog Chem Org Nat Prod 73, 1-140 (note includes triterpenoid saponins). 

Biosynthesis of Polyketides Phenolic Compounds derived from Shikimate The Biosynthesis of C5—C20 Terpenoid Compounds Triterpenoids, Steroids, and Carotenoids Non-protein Amino-acids, Cyanogenic Glycosides, and Glucosinolates Biosynthesis of Alkaloids. 

Lactuca saliva L. - Nervous Leaf (Infusion) Afro-Brazilians Phenolic acids [100] triterpenoids. ... 

Passiflora edulis Sims - maracuji, maracuja-de planta Tranquilizer, irritability Flower or leaf (decoction, ingested) Caboclos [53,57,59] Xokleng Indians [36] Flavonoids, glycosides, alkaloids [178] triterpenoids [179] saponins [180] norterpenoids derivatives [181] Cyanogenic glucosides [182] carotenoids [183] 3-Methyl-2-butanone [184] phenolic compounds [185] ... 

The phytochemical survey carried out with the species indicated, to which were attributed an anxiolytic effect showed that the main constituents found were the flavonoids, essential oils, as shown in Fig. (2), followed by the phenolic acids, sesquiterpenoids, triterpenoids, and alkaloids. 

Lactuca sativa L. - alface Insomnia, sedative Leaf (tea) Terena Indians [13] Afro-Brazilians (Northeast Brazil) [45,46] phenolic acids [100] triterpenoids, saponins [101,102] flavonoids [103] ... 

Saccharum officinarum L. -cana-de-afucar Insomnia Culm (suco) Caboclos [56] Flavonoids [344,345] long-chain aliphatic acids [347] fatty acids [346,348] phenolic compounds [349] glycans [350] triterpenoids and steroids [351] Anti-inflammatory and analgesic effects [348] antidiabetes [350]... 

Zeylasterone (154) is a novel phenolic 24-norfriedelane from K. zeylanica.108 Isoiquesterin (155) from Salaciamadagascariensis109 and (156) from S. macrosperma are new quinone methides.110 The biogenesis of triterpenoid quinone methides has been discussed.111... 

The chemical nature of amber is complex. Amber consists of complex mixtures of sesquiterpenoids, diterpenoids, and triterpenoids that have undergone polymerization and molecular reorganization during fossilization. Phenolic units may also be present. Baltic coast deposits, which contain about 8% succinic acid, are often called succinite. Amber is amorphous, and its infrared spectrum closely resembles those of nonvolatile resins from extinct pine trees. It is believed not to be a high polymer, the resinous state being accounted for by the complexity of materials present. Amber also serves as a repository for a variety of extinct species of insects. 

A preliminary chromatographic analysis of phytochemical constituents of selected species the three subfamilies in the Dipterocarpaceae was reported in 1977 [5], and indicated the presence of triterpenoids similar to dipterocarpol as constituents common to the three subfamilies. It was recommended that further studies on phenolic compounds such as flavonoids, which might be used as chemotaxonomic markers, should be carried out [5]. The present chapter focuses on the biologically active constituents of the plants in the family Dipterocarpaceae. 

Phenolic and 6-oxophenolic triterpenoids have also been reported. Zeylasterone (182) was the first celastroloid in this class to be described... 

Triterpenoid Saponins Phenolic Compounds Recent Methods of Structure Determination of Prenylated Phenols Biological Activities of Phenolic Constituents of Glycyrrhiza Species... 

As for the components of Morns root bark, occurrence of triterpenoids 12), diglycelide 13 and piperidine alkaloids 14) had been reported prior to the beginning of our work, whereas the hypotensive constituents had not been identified. In view of the reports cited in the previous paragraph we assumed that the hypotensive components were a mixture of unstable phenolic compounds and therefore undertook a study of the phenolic constituents of the root bark of the cultivated mulberry tree. This article reviews the chemistry and biological activities of phenolic constituents obtained from the mulberry tree and related plants. 

Two new chapters have been added—on fixed oils and triterpenoids—while the original phenol chapter has been divided into two. The new polyphenol chapter gives greater recognition to the plant tannins, as well as including a more comprehensive review of the flavonoids—previously grouped with glycosides. 

D-Glucuronic acid, a-linked to a glycerol unit, has been found as a constituent of ardiscrenolide E, a triterpenoid pentasaccharide from a Chinese shrub. 7 Both the phenolic and acyl p-D-glucuronides of salicylic acid, and the phenolic P-D-glucuionide of salicyluric acid (N-salicylyl-glycine) have been isolated from human urine by preparative h.p.l.c their stability in aqueous solution, and towards glucuronidase, was assessed. ... 

Chiang LC, Ng LT, Chiang W, Chang MY, Lin CC (2003) Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. Planta Med 69 600-604... 

Tan G, Zhu Z, Zhang H, Zhao L, Liu Y, Dong X, Lou Z, Zhang G, Chai Y (2010) Analysis of phenolic and triterpenoid compounds in licorice and rat plasma by high-performance liquid chromatography diode-array detection, time-of-flight mass spectnnnetry and quadmpole ion trap mass spectrometry. Rapid Commun Mass Spectnnn 24 209—218... 

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