Chapter 4 Macrocyclic Peptide Alkaloids From Plants

Itokawa, Hideji; Takeya, Koichi; Hitotsuyanagi, Yukio; Morita, Hiroshi

doi:10.1016/s0099-9598(08)60018-8

Cited by 31 publications

(47 citation statements)

References 204 publications

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“…After removal of the Boc group, compound 23 was subjected to macrocyclization at a concentration of 0.0013 m in DMF with EDC·HCl and HOOBt to afford bicyclic peptide 24 in 60 % yield. However, debenzylation of compound 24 under standard catalytic hydrogenolysis conditions (H 2 , Pd(OH) 2 or Pd/C, EtOH) did not afford compound 5 at all: it gave just a complex mixture of products. When compound 24 was treated with palladium on charcoal and 1,4-cyclohexadiene in EtOH, [26] it gave the desired deprotected compound in 80 % yield, though the reaction was very sluggish.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…RA-VII (1), isolated from Rubia cordifolia L. and R. akane Nakai (Rubiaceae), [1,2] bouvardin (NSC 259968; 2), isolated from Bouvardia ternifolia (Cav.) Schltdl.…”

Section: Introductionmentioning

confidence: 99%

“…Schltdl. (Rubiaceae), [3] and deoxybouvardin (RA-V; 3), [1][2][3] isolated from those three plants are bicyclic hexapeptides that are characterized by the presence of a unique strained 14-membered cycloisodityrosine unit in their structures (Scheme 1). These peptides possess promising antitumor activity, and from the late 1980s until the early 1990s, peptide 1 underwent phase I clinical trials as an anticancer drug in Japan.…”

Section: Introductionmentioning

confidence: 99%

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Isolation, Structure Determination, and Synthesis of Allo‐RA‐V and Neo‐RA‐V, RA‐Series Bicyclic Peptides from Rubia cordifolia L.

Hitotsuyanagi

Odagiri

Kato

et al. 2012

Chemistry A European J

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Two bicyclic hexapeptides, allo-RA-V (4) and neo-RA-V (5), and one cyclic hexapeptide, O-seco-RA-V (6), were isolated from the roots of Rubia cordifolia L. Their gross structures were elucidated on the basis of spectroscopic analysis and X-ray crystallography of compound 5. The absolute stereochemistry of compounds 4 and 5 were established by their total syntheses, and the absolute stereochemistry of compound 6 by chemical correlation with deoxybouvardin (3). Comparison of the 3D structures of highly active RA-VII (1) with less-active compounds 4 and 5 suggests that the orientation of the Tyr-5 and/or Tyr-6 phenyl rings plays a significant role in their biological activity. The isolation of peptides 4-6, along with compound 3, and the comparison of their structures seem to indicate that peptide 6 may be the common precursor to bicyclic peptides 3-5 in the plant.

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Section: Wwwchemeurjorgmentioning

confidence: 99%

“…RA-VII (1), isolated from Rubia cordifolia L. and R. akane Nakai (Rubiaceae), [1,2] bouvardin (NSC 259968; 2), isolated from Bouvardia ternifolia (Cav.) Schltdl.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Isolation, Structure Determination, and Synthesis of Allo‐RA‐V and Neo‐RA‐V, RA‐Series Bicyclic Peptides from Rubia cordifolia L.

Hitotsuyanagi

Odagiri

Kato

et al. 2012

Chemistry A European J

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“…1 Their cyclic nature often provides more lipophilicity and membrane permeability, because of reduced zwitterionic character. Furthermore, restricted bond rotation results in rigid backbone conformation with more affinity and selectivity for binding proteins.…”

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confidence: 99%

Structure of a new cyclic nonapeptide, segetalin F, and vasorelaxant activity of segetalins from Vaccaria segetalis

Morita

Eda

Iizuka

et al. 2006

Bioorganic & Medicinal Chemistry Letters

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“…Bicyclic hexapeptide RA-VII (1) [1][2][3] (Fig. 1) and its 24 congeners isolated from Rubia cordifolia L. and R. akane Nakai (Rubiaceae), and two more related peptides, bouvardin (NSC 259968) (2) [4] and deoxybouvardin (RA-V) (3), from another plant of this family, Bouvardia ternifolia (Cav.)…”

Section: Introductionmentioning

confidence: 99%

Production of monoclonal antibodies against antitumor cyclohexapeptide RA-VII from Rubia cordifolia and their characterization

2011

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An immunoassay system was established for the estimation of the quantity of an antitumor cyclic hexapeptide RA-VII (1) from Rubia cordifolia L. and R. akane Nakai (Rubiaceae). First, 1 was converted into its hapten, which was then conjugated with a carrier protein to be used as an effective antigen to obtain its monoclonal antibody (MAb). In the resulting conjugate, the molecular ratio between 1 and the carrier protein as assayed by matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF MS) was about 5:1. Then, the splenocytes from the mouse immunized with the conjugate were fused with mouse myeloma cells to produce hybridoma, secreting MAb against 1. Two clones were isolated, one producing MAb IgG(1) and the other IgM, both having a κ light chain. The sensitivity and cross-reactivity of the thus obtained MAb were also assayed.

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Chapter 4 Macrocyclic Peptide Alkaloids From Plants

Cited by 31 publications

References 204 publications

Isolation, Structure Determination, and Synthesis of Allo‐RA‐V and Neo‐RA‐V, RA‐Series Bicyclic Peptides from Rubia cordifolia L.

Isolation, Structure Determination, and Synthesis of Allo‐RA‐V and Neo‐RA‐V, RA‐Series Bicyclic Peptides from Rubia cordifolia L.

Structure of a new cyclic nonapeptide, segetalin F, and vasorelaxant activity of segetalins from Vaccaria segetalis

Production of monoclonal antibodies against antitumor cyclohexapeptide RA-VII from Rubia cordifolia and their characterization

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