New Hydroxylated Spermidine Alkaloids from <i>Pleurostylia opposita</i>(W<scp>ALL</scp>.) M<scp>ERILL</scp>‐M<scp>ETCALF</scp>

Seguineau, C.; Richomme, Pascal; Bruneton, J.; Pusset, J.

doi:10.1002/hlca.19920750714

Helvetica Chimica Acta

1992

DOI: 10.1002/hlca.19920750714

|View full text |Cite

New Hydroxylated Spermidine Alkaloids from Pleurostylia opposita(WALL.) MERILL‐METCALF

C. Seguineau¹,

Pascal Richomme²,

J. Bruneton³

et al.

Abstract: The leaves of a New Caledonian celastraceae, Pleurostylia opposita (WALL.) MERRILL‐METCALF, have yielded three new spermidine alkaloids, 7‐hydroxypleurostyline (1), 7‐hydroxycelacinnine (2), and 7′‐hydroxy‐7′,8′‐dihydropleurostyline (3), as minor basic constituents, together with three related alkaloids pleurostyline (4), celacinnine (5), and celallocinine (6).

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1993

2006

Publication Types

Select...

Article6

Relationship

Self Cite0

Independent6

Authors

Journals

Cited by 14 publications

(8 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…SeÂguineau et al have isolated several novel hydroxylated spermidine alkaloids from the leaves of a New Caledonian Celastraceae, Pleurostylia opposita (Wall.) Merrill-Metcalf [3] [4]. Their proposed structures for 3-hydroxycelacinnine (1) (originally named 7-hydroxycelacinnine [3]), 7-hydroxypleurostyline (2), and 7-hydroxypleurocorine (3) are shown in Scheme 1 1 ).…”

mentioning

confidence: 99%

“…Merrill-Metcalf [3] [4]. Their proposed structures for 3-hydroxycelacinnine (1) (originally named 7-hydroxycelacinnine [3]), 7-hydroxypleurostyline (2), and 7-hydroxypleurocorine (3) are shown in Scheme 1 1 ). The presence of an OH group at the a-position to the lactam carbonyl group represents a new feature in such alkaloids.…”

mentioning

confidence: 99%

“…The presence of an OH group at the a-position to the lactam carbonyl group represents a new feature in such alkaloids. A biosynthetic pathway of their formation involving an epoxy precursor has been suggested [3] [4] (Scheme 1) 2 ). We are interested in the structure verification and biosynthesis of these alkaloids.…”

mentioning

confidence: 99%

“…A large difference between coupling constants (9.0 vs. 1.2 Hz) as well as a significant difference between 1 H-NMR chemical shifts in the HÀC(2)ÀC(3)ÀH moiety of the synthesized 1 and the natural 3-hydroxycelacinnine [3] [4] suggest that the proposed relative trans-configuration (2R*,3R*) for the natural alkaloid should be changed to the corresponding cisconfiguration (2R*,3S*). Also, the same conclusion holds for 2 and 3, as well, since all three natural alkaloids had almost identical 1 H-and 13 C-NMR data for this moiety [3] [4].…”

mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R,3R)-3-Hydroxycelacinnine

Khanjin

Hesse

2001

HCA

View full text Add to dashboard Cite

The macrocyclic lactam alkaloid (±)‐(2R*,3R*)‐3‐hydroxycelacinnine (1) derived from spermidine was synthesized via stereoselective epoxide‐ring opening with magnesium azide and cesium carbonate promoted macrocyclization of the ditosylated diamino precursor 12 with 1,4‐dibromobutane in the two key steps (Scheme 2). 1H‐ and 13C‐NMR Signal assignments from COSY, HSQC, and HMBC 2D NMR data of the synthesized 1 were compared with the earlier‐described data of the natural 3‐hydroxycelacinnine. The similarity of their 13C‐NMR spectra point to the correctness of the proposed constitutional formula for natural 3‐hydroxycelacinnine; however, different 1H‐NMR chemical shifts and coupling constants (J(2,3)=9.0 vs. 1.2 Hz, resp.) in the α‐hydroxy‐β‐amino lactam moiety suggest that natural 3‐hydroxycelacinnine is the 2,3‐cis‐epimer of one synthetic (±)‐1.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R,3R)-3-Hydroxycelacinnine

Khanjin

Hesse

2001

HCA

View full text Add to dashboard Cite

show abstract

“…The molecular formula, C 44 H 51 NO 17 , was determined by HRESIMS, and suggested that oppositine B (2) had one less oxygen than oppositine A (1). Comparison of the NMR data of 2 with 1 confirmed the absence of the hydroxyl at the C-4 position.…”

mentioning

confidence: 99%

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

et al. 2006

View full text Add to dashboard Cite

Two new sesquiterpene pyridine alkaloids, oppositines A (1) and B (2), have been isolated from the plant, Pleurostylia opposita (Celastraceae), collected in Sri Lanka. The compounds were isolated and purified by solvent/solvent partitioning, column chromatography and HPLC. Their structures were assigned on the basis of extensive 1D and 2D NMR studies as well as analysis by HRESIMS. Oppositines A (1) and B (2) showed moderate cytotoxicity against HCT116 cell lines with EC 50 values of 27 ± 2 and 26 ± 3 μM, respectively.Poly-acetylated sesquiterpene pyridine alkaloids are ubiquitously found in the Celastraceae family of plants. 1-4 Dihydro-β-agarofuran sesquiterpenes frequently incorporate pyridine dicarboxylic acids to bridge their sesquiterpenoid cores at the C-3 and C-13 positions. The dihydro-β-agarofuran skeleton is comprised of a decalin ring, a tetrahydrofuran ring, and methyl substituents located at the C-4, C-10, and two at the C-11 position. Evoninic, wilfordic, edulic, cathaic, and cassininic (often misnamed cassinic) acids are some of the pyridine carboxylic acids present in this class of sesquiterpenes. These compounds are of interest due to their wide range of biological activities including: cytotoxicity, 1 immunosuppression, 2 insecticidal, 3,5,6 insect-antifeedant, 5,7 anti-HIV, 4 reversal of the multidrug resistance (MDR) phenotype, 8-11 and antitumor. 12 As part of an ongoing search for bioactive compounds, two new sesquiterpene alkaloids, oppositines A (1) and B (2), were isolated from the Sri Lankan plant, Pleurostylia opposita (Wallich, 1824) (Celastraceae).The air dried stem bark of P. opposita was extracted with 1:1 MeOH/CH 2 Cl 2 . The extract was dried and partitioned between petroleum ether and aqueous MeOH, and the aqueous MeOH was subsequently partitioned with chloroform. The chloroform-soluble material was fractionated using size exclusion chromatography, preparative TLC, and reversed-phase HPLC resulting in oppositines A (1) and B (2).

show abstract

Absolute configuration of macrocyclic spermidine alkaloids

et al. 1997

View full text Add to dashboard Cite

In this short review of several macrocyclic spermidine alkaloids, special consideration has been given to the correct determination of the absolute configuration at their chiral centers. The bases of interest are characterized by possessing a 13‐membered macrocyclic lactam ring incorporating spermidine and either cinnammic or fatty acid precursorial units. In this context, the synthesis of some of these alkaloids is presented and the first total synthesis of optically pure (+)‐(S)‐viburnine, and (−)‐(S)‐celafurine is reported. Finally, a common initial step in biosynthesis starting with an enzyme‐catalyzed Michael addition of spermidine to an α,β‐unsaturated acid is proposed. Chirality 9:523–528, 1997. © 1997 Wiley‐Liss, Inc.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

New Hydroxylated Spermidine Alkaloids from Pleurostylia opposita(WALL.) MERILL‐METCALF

Cited by 14 publications

References 6 publications

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R,3R)-3-Hydroxycelacinnine

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R,3R)-3-Hydroxycelacinnine

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

Absolute configuration of macrocyclic spermidine alkaloids

Contact Info

Product

Resources

About

New Hydroxylated Spermidine Alkaloids from Pleurostylia opposita(WALL.) MERILL‐METCALF

Cited by 14 publications

References 6 publications

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R*,3R*)-3-Hydroxycelacinnine

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R*,3R*)-3-Hydroxycelacinnine

Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita

Absolute configuration of macrocyclic spermidine alkaloids

Contact Info

Product

Resources

About

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R,3R)-3-Hydroxycelacinnine

Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R,3R)-3-Hydroxycelacinnine