Natural sesquiterpenoids

Fraga, Braulio M.

doi:10.1039/b108977n

Cited by 64 publications

(26 citation statements)

References 270 publications

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“…To the best of our knowledge, there are three known sesquiterpene skeletons with 6/5/5 ring systems: cedrane, prezizaane, and zizaane (Figure 3). 12,13 However, these skeletons are totally different from that of acaciicolin A ( 1 ). We propose the name “acaciicolane” for the norsesquiterpene skeleton of 1 (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

Tricyclic and Spirobicyclic Norsesquiterpenes from the Endophytic Fungus Pseudolagarobasidium acaciicola

et al. 2014

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The new tricyclic and spirobicyclic norsesquiterpenes 1 and 2 and the new nor-chamigrane endoperoxide 3, together with the known sesquiterpenes steperoxide A (4), merulin B (5), and merulin C (6), were isolated from the endophytic fungus Pseudolagarobasidium acaciicola. The structures and absolute configurations of 1-3 were determined by analysis of spectroscopic data, as well as by single-crystal X-ray

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Section: Resultsmentioning

confidence: 99%

Tricyclic and Spirobicyclic Norsesquiterpenes from the Endophytic Fungus Pseudolagarobasidium acaciicola

et al. 2014

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“…Geraniol, limonene, linalool, and pinene are some of the volatile components detected in fruit samples ( Figure 3 ). Terpenes, mainly sesquiterpenes, have been identified in the root, bark, flowers, and leaves of plants [ 92 ]. Only a few terpenes have been discovered in fruits.…”

Section: Phytochemicals In 15 Selected Indigenous Tropical Fruitsmentioning

confidence: 99%

Phytochemicals and Medicinal Properties of Indigenous Tropical Fruits with Potential for Commercial Development

Khoo

Azlan

Kong

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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Hundreds of fruit-bearing trees are native to Southeast Asia, but many of them are considered as indigenous or underutilized. These species can be categorized as indigenous tropical fruits with potential for commercial development and those possible for commercial development. Many of these fruits are considered as underutilized unless the commercialization is being realized despite the fact that they have the developmental potential. This review discusses seven indigenous tropical fruits from 15 species that have been identified, in which their fruits are having potential for commercial development. As they are not as popular as the commercially available fruits, limited information is found. This paper is the first initiative to provide information on the phytochemicals and potential medicinal uses of these fruits. Phytochemicals detected in these fruits are mainly the phenolic compounds, carotenoids, and other terpenoids. Most of these phytochemicals are potent antioxidants and have corresponded to the free radical scavenging activities and other biological activities of the fruits. The scientific research that covered a broad range of in vitro to in vivo studies on the medicinal potentials of these fruits is also discussed in detail. The current review is an update for researchers to have a better understanding of the species, which simultaneously can provide awareness to enhance their commercial value and promote their utilization for better biodiversity conservation.

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“…21) On the other hand, functionalization, especially oxygenation, of octahydronaphthalenes or decalin derivatives is also very important because many bioactive or natural compounds contain a skeleton resembling the AB fused ring of cholesterol. [22][23][24] Therefore, we wished to identify the required structural factors for regio-and stereoselective direct 7a-hydroxylation of steroids by our electrochemical method, as well as to extend the range of applicability of this method for allylic a-hydroxylation of small cyclic compounds.…”

Section: IIImentioning

confidence: 99%

Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

Okamoto

Funaki

Nobuchika

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oxygenation reactions are very important in steroid metabolism and biosynthesis.1-3) Many investigations on biomimetic oxygenation systems using iron(III) picolinate (Fe III (PA) 3 ) or iron(II) picolinate (Fe II (PA) 2 ) complexes as catalysts have been reported under various conditions and in various solvents, [4][5][6][7][8] but direct 7a-hydroxylation is not easy and most reported allylic hydroxylations involve multistep reactions via other functionalized compounds [9][10][11][12][13][14] or afford low yield or stereoselectivity. [15][16][17] We have been developing a 7a-hydroxylation system for steroids, [18][19][20] and we reported in a preceding paper that the combination of electrolysis and the Fe III (PA) 3 /O 2 /CH 3 CN system gave good results in the hydroxylation of cholesteryl acetate. 21)On the other hand, functionalization, especially oxygenation, of octahydronaphthalenes or decalin derivatives is also very important because many bioactive or natural compounds contain a skeleton resembling the AB fused ring of cholesterol.22-24) Therefore, we wished to identify the required structural factors for regio-and stereoselective direct 7a-hydroxylation of steroids by our electrochemical method, as well as to extend the range of applicability of this method for allylic a-hydroxylation of small cyclic compounds.In this report, we describe the iron picolinate-induced hydroxylation reactions of octahydronaphthalene derivatives 5b, 6b and 7b as simple models for allylic oxygenation of steroids or other decalin derivatives. Results and DiscussionThe substrates 5b-7b were prepared by benzoylation of the corresponding octahydronaphthalenols 5a-7a. [25][26][27] Both 5b and 6b have an alkene moiety at a similar position to C5-C6 of cholesterol. However, the double bond of 7b is not located at the bridgehead of the fused ring. We applied Showa Pharmaceutical University; 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan. Received October 23, 2004; accepted November 11, 2004; published online November 22, 2004 The combination of electrolysis and the Fe III (PA) 3 /O 2 /CH 3 CN system was investigated for allylic hydroxylation of octahydronaphthalene derivatives. Substrates with a bridgehead double bond gave the allylic alcohol with a a-preference, while non-bridgehead olefin did not react smoothly. This system is a useful tool for a a-selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond as model compounds for the AB fused ring of cholesterols.

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Natural sesquiterpenoids

Abstract: This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2001 is reviewed, and 404 references are cited.

Cited by 64 publications

References 270 publications

Tricyclic and Spirobicyclic Norsesquiterpenes from the Endophytic Fungus Pseudolagarobasidium acaciicola

Tricyclic and Spirobicyclic Norsesquiterpenes from the Endophytic Fungus Pseudolagarobasidium acaciicola

Phytochemicals and Medicinal Properties of Indigenous Tropical Fruits with Potential for Commercial Development

Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

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