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

Morita, Hiroshi; Eda, Michiko; Iizuka, Tokio; Hirasawa, Yusuke; Sekiguchi, Mitsuhiro; Yun, Young Sook; Itokawa, Hideji; Takeya, Koichi

doi:10.1016/j.bmcl.2006.06.083

Cited by 44 publications

(29 citation statements)

References 14 publications

(8 reference statements)

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“…Therefore, research on the structure-activity relationship is significant. The same results were observed on the aortic without endothelium for the six segetalins (Morita et al 2006). The effect of the aqueous extract is endothelium-dependent and may be linked to the release of nitric oxide, decrease of Ca 2+ in cytoplasm and effect on the PGI 2 /cAMP pathway (E et al 2007).…”

Section: Effect On the Blood And Vesselsupporting

confidence: 76%

“…In addition, both the aqueous extract and five cyclic peptides (segetalin A, D, F, G and H) showed a vasorelaxant effect on the aortic rings with endothelium in vitro (Morita et al 2006;E et al 2007). Interestingly, one cyclic peptide (segetalin B) performed a contrary activity.…”

Section: Effect On the Blood And Vesselmentioning

confidence: 94%

“…Except segetalin F (33), all of them contain glycine. Chromatographic purification of EtOAc partition of MeOH extraction produced segetalins A-E (28-32), while chromatographic purification of n-BuOH partition brought segetalins F-H (33-35) (Morita et al 2006). Additionally, pressurized low polarity water extraction (Güçlü-Ü stündag and Mazza 2008) and high-speed counter-current chromatography ) have emerged as an attractive alternative to traditional methods for the isolation of segetalins.…”

Section: Vaccariosementioning

confidence: 98%

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Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review

et al. 2015

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Vaccaria hispanica is utilized medicinally both in China and Turkey. Phytochemical screenings demonstrated that the phytochemical diversity of V. hispanica at least includes 63 distinct metabolites, embracing triterpenoid saponins, cyclic peptides, flavonoids and others. The pharmacological studies confirmed that the crude extracts or purified compounds from the plant showed galactopoietic activity, antitumor activity, effect on the blood and vessel, antioxidant activity, ameliorative effect on osteopenia and others. The present paper is aimed to provide a critical analysis of data from scientific evaluations and aimed to find out the linkage of the medicinal uses to the scientific studies. Simultaneously, the possible future direction and perspective for investigations are discussed, as well.

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Section: Effect On the Blood And Vesselsupporting

confidence: 76%

Section: Effect On the Blood And Vesselmentioning

confidence: 94%

Section: Vaccariosementioning

confidence: 98%

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Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review

et al. 2015

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“…Among these, cyclic peptides and related congeners with unique structures and wide pharmacological profile [7][8][9][10] have received special attention which may prove better candidates to overcome the problem of wide spread increase of resistance towards conventional drugs. Different pharmacological activities possessed by cyclic peptides obtained from latex, seeds and roots of plants, include antitumour activity [11][12][13] , immunosuppressive and antimalarial activity 14 , vasorelaxant activity 15,16 , tyrosinase inhibitory activity 17,18 and estrogen-like activity 19,20 . Recently, a natural cyclopolypeptide, cherimolacyclopeptide E, has been isolated from seeds of small tree Annona cherimola and the structure was elucidated by MS/MS fragmentation experiments, extensive 2D-NMR analysis/chemical degradation and showed significant cytotoxic activity against KB (human nasopharyngeal carcinoma) cells 21 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Evaluation of a Glycine-Rich Peptide - Cherimolacyclopeptide E

Dahiya

2007

J. Chil. Chem. Soc.

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The synthesis of a natural cyclic peptide cherimolacyclopeptide E (12) by coupling of tripeptide units Boc-gly-leu-gly-OCH 3 (9) and Boc-phe-tyr-pro-OCH 3 (10) after proper deprotection at carboxyl and amino terminals followed by cyclization of linear hexapeptide segment, is described. Structure elucidation of the cyclopeptide 12 is based on detailed spectral analysis such as FTIR, 1 H NMR, 13 C NMR, FAB MS and elemental analysis. After biological screening, the newly synthesized peptide exhibited high cytotoxicity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines with CTC 50 values of 2.76 and 4.96 μM, and potent antimicrobial activity against pathogenic microbes P. aeruginosa, E.coli and C. albicans with MICs between 12.5-6 μg/mL. Furthermore, compound 12 possessed moderate anthelmintic activity against earthworms M. konkanensis, P. corethruses and Eudrilus sp. at 2 mg/mL dose level.

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“…7) This alkaloid possesses an unprecedented tricyclic skeleton and exhibits potent antiplasmodial activity. 6,8,9) Although we have recently reported that some alkaloids and peptides exhibit not only antiplasmodial activity, but also vasorelaxant activity in the rat aorta, [10][11][12] the effect of cassiarin A on vascular tone remains unclear. We have very recently found that cassiarin A induces relaxation in the rat thoracic aorta and this was largely due to endotheliumderived nitric oxide (NO).…”

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confidence: 99%

Vasodilator Effect of Cassiarin A, a Novel Antiplasmodial Alkaloid from Cassia siamea, in Rat Isolated Mesenteric Artery

Matsumoto

Kobayashi

Ishida

et al. 2010

Biological & Pharmaceutical Bulletin

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Cassia siamea (Leguminosae), a small-to medium-sized tree, is one of the most commonly cultivated trees in Southeast Asia. Different parts of this plant can be used for a variety of medical purposes, giving the plant considerable medicinal potential. In traditional folk medicine, its stem bark is used as a mild, pleasant, safe purgative; a decoction of the bark is given to treat diabetes; a paste is used as a dressing for ringworm and chilblains; the roots are used as an antipyretic; and the leaves are used for the treatment of constipation, hypertension, and insomnia.1,2) A number of compounds, including barakol, emodin, b-and g-sitosterol, lupeol, luteolin, D-pinitol, chromone alkaloids, flavonoid glycosides, and a number of anthraquinones and bianthraquinones, have been isolated from Cassia siamea. 1,3,4) Although members of the genus Cassia are widely distributed in tropical and subtropical regions, where they have long been used in traditional folk medicine, particularly for the treatment of periodic fever and malaria, 5) we only recently have isolated the novel heteroaromatic alkaloid cassiarin A (Fig. 1) from the leaves of Cassia siamea. 6) This was followed a year later by the first total synthesis of cassiarin A, a process completed in eight steps from a known compound, methyl 2,4-dihydroxybenzoate.7) This alkaloid possesses an unprecedented tricyclic skeleton and exhibits potent antiplasmodial activity. 6,8,9) Although we have recently reported that some alkaloids and peptides exhibit not only antiplasmodial activity, but also vasorelaxant activity in the rat aorta, 10-12) the effect of cassiarin A on vascular tone remains unclear. We have very recently found that cassiarin A induces relaxation in the rat thoracic aorta and this was largely due to endotheliumderived nitric oxide (NO).9) However, no study has investigated the effects of cassiarin A on vascular tone in other, smaller arteries. The primary purpose of this study was therefore to test the hypothesis that cassiarin A induces in vitro vascular relaxation in rat mesenteric arteries precontracted with phenylephrine. In addition, we wanted to determine whether the vascular relaxation is endothelium dependent or whether cassiarin A acts directly upon vascular smooth muscle. MATERIALS AND METHODS Drugs and Chemicals, glibenclamide, 4-aminopyridine (4-AP), and tetraethylammonium (TEA) were all purchased from Sigma Chemical Co. (St. Louis, MO, U.S.A.). Acetylcholine chloride was from Daiichi-Sankyo Pharmaceuticals (Tokyo, Japan), 1H-[1,2,4]oxadiazolo[4,3-a]-quinoxalin-1-one (ODQ) was from Wako (Osaka, Japan), and iberiotoxin was from the Peptide Institute Inc. (Osaka, Japan). Drugs were dissolved in saline, except for glibenclamide [dissolved in dimethyl sulfoxide (DMSO)] and indomethacin (dissolved first in a small amount of Na 2 CO 3 0.1 M solution, then made up to the final volume with distilled water).Cassiarin A was prepared as previously reported. 6) Briefly, leaves of Cassia siamea (collected at the Purwodadi Botanical Garden, Pasuruan, Indon...

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

Cited by 44 publications

References 14 publications

Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review

Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review

Synthesis, Characterization and Biological Evaluation of a Glycine-Rich Peptide - Cherimolacyclopeptide E

Vasodilator Effect of Cassiarin A, a Novel Antiplasmodial Alkaloid from Cassia siamea, in Rat Isolated Mesenteric Artery

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