Constituents of Endiandra species. II. (E)-4-(6'-Phenyltetracyclo[5,4,2,03,13,010,12]-trideca-4',8'-dien-11'-yl)but-2-enoic acid from Endiandra introrsa (Lauraceae)

Bandaranayake, WM; Banfield, J. E.; Black, D. St. C.

doi:10.1071/ch9820557

Cited by 30 publications

(19 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first members of this class of compound, endiandric acid A and B ( 3 – 4 ) were isolated from the leaves of Endiandra introrsa [ 35 , 36 , 37 , 38 , 39 ]. Endiandric acid A ( 3 ) was also obtained from the leaves of other species such as B. obtusifolia and B. oligandra [ 40 ].…”

Section: Chemical Constituentsmentioning

confidence: 99%

“…This group contains compounds that possess bi-, tri- or tetracyclic fused ring systems other than skeleton 1 and 2 . In this group are beilschmiedic acid G ( 64 ) having an aromatic ring and beilschmiedin ( 65 ) with a seven-membered cyclic ether group isolated from B. anarcardiodes [ 19 , 20 ]; tricyclotsangibeilin, an endiandric acid derivative with cyclododecane ring system ( 66 ) isolated from the roots of B. tsangii [ 22 ] and the bicyclic endiandric acids D ( 67 ), E ( 68 ), F ( 69 ) and G ( 70 ) isolated from E. introrsa [ 35 , 36 , 37 , 38 , 39 , 40 ]. …”

Section: Chemical Constituentsmentioning

confidence: 99%

“…They have been the subject of very intensive chemical investigations by various research groups starting from the middle of the 1960s, with a large number of compounds isolated from different species. However, phytochemical investigations have been mostly conducted on 31 species of Beilschmiedia ( Beilschmiedia alloiophylla , B. anacardioides , B. bernesii , B. brevipes , B. chancho chancho , B. collina , B. costaricensis , B. cryptocaryoides , B. elliptica , B. erythrophloia , B. fulva , B. tsangii , B. ferruginea , B. kunstleri , B. madang , B. manii , B. miersii , B. obscura , B. obtusifolia , B. oligandra , B. oreophila Schlechter, B. pendula , B. podagrica , Beilschmiedia spp (from Gabon), B. talaranensis , B. tarairie , B. tawa , B. tooram , B. tovarensis , B. volckii , and B. zenkeri ) [ 12 , 13 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ] and 11 species of Endiandra ( Endiandra anthropophagorum , E. bassaphila , E. baillonii , E. introsa , E. jonesii , E. kingiana , E. leptodendron , E. monothyra , E. palmerstonii , E. xanthocarpa , and E. wolfii ) [ 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ]. These investigations led to the isolation and characterization of various classes of secondary metabolites, of which endiandric acid derivatives, epoxyfuranoid lignans, kin...…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae)

et al. 2015

View full text Add to dashboard Cite

Plants of the Lauraceae family are widely used in traditional medicine and are sources of various classes of secondary metabolites. Two genera of this family, Beilschmiedia and Endiandra, have been the subject of numerous investigations over the past decades because of their application in traditional medicine. They are the only source of bioactive endiandric acid derivatives. Noteworthy is that their biosynthesis contains two consecutive non-enzymatic electrocyclic reactions. Several interesting biological activities for this specific class of secondary metabolites and other constituents of the two genera have been reported, including antimicrobial, enzymes inhibitory and cytotoxic properties. This review compiles information on the structures of the compounds described between January 1960 and March 2015, their biological activities and information on endiandric acid biosynthesis, with 104 references being cited.

show abstract

Section: Chemical Constituentsmentioning

confidence: 99%

Section: Chemical Constituentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae)

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Isolated from the leaves of Endiandra intorsa , the endiandric acids 1 ( e.g. endiandric acid A, 1 , Scheme 1 ) possess complex and synthetically challenging tetracyclic frameworks.…”

Section: Introductionmentioning

confidence: 99%

Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

2015

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4][5][6][7][8][9][10][11][12][13] These complex fatty acids, typically isolated as racemic mixtures, were proposed by Black to be the result of a series of consecutive nonenzymatic cyclizations (8πe, 6πe, and DielsAlder) of a polyunsaturated fatty acid precurser. 14 Support for such a mode of biosynthesis was provided by a biomimetic synthesis carried out by Nicolaou.…”

mentioning

confidence: 99%

Cytotoxic and antibacterial beilschmiedic acids from a gabonese species of Beilschmiedia

Williams

et al. 2012

Planta Med

View full text Add to dashboard Cite

High-throughput natural products chemistry methods have facilitated the isolation of eight new (1-8) and two known (9 and 10) beilschmiedic acid derivatives from the leaves of a Gabonese species of Beilschmiedia. Compounds 3-10 were isolated in microgram quantities, and the NMR data for structure elucidation and dereplication were acquired utilizing a Bruker BioSpin TCI 1.7 mm MicroCryoProbe. All of the compounds were screened for cytotoxic and antibacterial activity against NCI-H460 human lung cancer cells and a clinical isolate of methicillin-resistant Staphylococcus aureus, respectively. This is the first report of cytotoxic activity for the endiandric/ beilschmiedic acid class of compounds.A few species of Beilschmiedia and one species of Endiandra have been found to produce a remarkable series of polycyclic fatty acids known as beilschmiedic and endiandric acids. [1][2][3][4][5][6][7][8][9][10][11][12][13] These complex fatty acids, typically isolated as racemic mixtures, were proposed by Black to be the result of a series of consecutive nonenzymatic cyclizations (8πe, 6πe, and DielsAlder) of a polyunsaturated fatty acid precurser. 14 Support for such a mode of biosynthesis was provided by a biomimetic synthesis carried out by Nicolaou. 15 To date, 29 of these compounds have been reported in the literature as natural products, with 31 additional compounds resulting from derivatization and synthesis. Recent publications have reported antibacterial and anti-inflammatory activity. 9,10,13 Additionally, one analogue was the subject of a patent that claimed it was useful in the treatment of asthma. 7 Given the unique chemical space occupied by these compounds, and the lack of biological activity reported, we checked our plant library to see if any material was available that could yield similar compounds. We found that our library contained two collections of Beilschmiedia from Gabon. One had previously been screened for cytotoxic activity and was found to be active. Further examination of that hit resulted in the isolation of the known beilschmiedic acids A (9) and C (10), 9 as well as eight new beilschmiedic acids H -O (1-8). Compounds 4, 5, 7, and 8 represent new frameworks as described by Lipkus, et al. 16,17 Several of the compounds demonstrated moderate cytotoxic activity in the NCI-H460 human lung cancer cell line. The second collection contained no evidence of beilschmiedic acids as indicated by thorough HPLC and NMR analysis. , COSY correlations could be followed through the entirety of compound 1 (Figure 1) with the only exceptions being the three quaternary carbons. Those were assigned based on HMBC correlations (Figure 1). In particular, HMBC correlations from H-5 (δ H 6.91) to CO 2 H (δ C 170.4) and from H-4 (δ H 4.14) to C-6 (δ C 136.5) confirmed the presence of the α/β-unsaturated carboxylic acid. Likewise, HMBC correlations from H-6′ (δ H 6.78) to C-8′ (δ C 139.8) and from H-9′/13′ (δ H 7.38) to C-7′ (δ C 131.3) confirmed the location of the phenyl moiety. Finally, HMBC correlations from ...

show abstract

Constituents of Endiandra species. II. (E)-4-(6'-Phenyltetracyclo[5,4,2,03,13,010,12]-trideca-4',8'-dien-11'-yl)but-2-enoic acid from Endiandra introrsa (Lauraceae)

Abstract: The structure (5) of the title compound, a vinylog of endiandric acid, is proposed on the basis of chemical and spectroscopic evidence.

Cited by 30 publications

References 0 publications

Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae)

Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae)

Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

Cytotoxic and antibacterial beilschmiedic acids from a gabonese species of Beilschmiedia

Contact Info

Product

Resources

About