Testosterone 5.ALPHA.-Reductase Inhibitory Active Constituents of Piper nigrum Leaf

Hirata, Noriko; Tokunaga, Masashi; Naruto, Shunsuke; Iinuma, Munekazu; Matsuda, Hideaki

doi:10.1248/bpb.30.2402

Cited by 42 publications

(25 citation statements)

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“…Two major lignans of PN-ext, (Ϫ)-cubebin (1) and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (2), were already isolated from the ethyl acetate soluble fraction as described in the previous paper. 1,4) Because Tsuruga et al 15) reported that several cubebin-type lignans having 3,4-dibenzyltetrahydrofuran ring, such as matairesinol and trachelogenin, had significant histamine release inhibitory activities, we examined inhibitory effects of 1 and 2 on compound 48/80-induced histamine release from rat peritoneal mast cells. As shown in Table 3, the inhibitory activities of 1 and 2 were superior to that of SCG.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4] It was suggested that these substances may be useful ingredients of hair-care cosmetics for prevention of gray hair and alopecia. As a part of our continuous study on P. nigrum leaf, we examined anti-allergic effect of the leaf, because hair care cosmetics having anti-allergic activity may be desirable.…”

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confidence: 99%

“…Natural (Ϫ)-cubebin (1) and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (2) were isolated from the EtOAc soluble fraction. 1,4) Animals Female BALB/c strain mice (14-19 g), female ICR strain mice (30-32 g) and male Wistar strain rats (160-180 g) were provided by SLC (Japan SLC, Hamamatsu, Japan). They were maintained in an air-conditioned room with lighting from 7 a.m. to 7 p.m.…”

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confidence: 99%

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Histamine Release Inhibitory Activity of Piper nigrum Leaf

Hirata

Naruto

Inaba

et al. 2008

Biological & Pharmaceutical Bulletin

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During the course of our search for useful ingredients of cosmetics from natural resource, we have previously reported that Piper nigrum leaf extract showed both melanogenesis stimulation activity and testosterone 5a-reductase inhibitory activity and that (Ϫ)-cubebin (1) and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (2) were isolated as active lignan constituents. [1][2][3][4] It was suggested that these substances may be useful ingredients of hair-care cosmetics for prevention of gray hair and alopecia. As a part of our continuous study on P. nigrum leaf, we examined anti-allergic effect of the leaf, because hair care cosmetics having anti-allergic activity may be desirable. It has been reported that antiallergic effect of a botanical formulation 5) in which P. nigrum fruit was included. Anti-allergic activity of piperine, 6) a major alkaloid amide of P. nigrum fruit have been reported, but HPLC analysis revealed that the piperine content in the leaf was 0.00007%. 7) Moreover, we have not found any reports on anti-allergic effect of the leaf. In this paper, we describe in vivo anti-allergic effects of P. nigrum leaf extract against type I allergy model and type IV allergy model in mice. 2,4-Dinitrofluorobenzene (DNFB) has been shown to induce triphasic increase in ear thickness of mouse by the challenge after a passive sensitization with monoclonal antidinitrophenyl (DNP) IgE antibody. 8,9) This model serves as an animal model for type I allergy. 8,9) In addition, we used picryl chloride (PC)-induced contact dermatitis in mice as an animal model for type IV allergy.10) Inhibitory effects of Piper nigrum leaf extract, on histamine release were also examined by in vitro assay using compound 48/80-induced histamine release from rat peritoneal mast cells. MATERIALS AND METHODS Plant MaterialsPiper nigrum leaf was the same sample described in the previous paper. 1-4)Reagents 2,4-Dinitrofluorobenzene (DNFB), Ficoll, Hanks' balanced salt solution, olive oil, o-phthaldialdehyde, picryl chloride (PC), and sodium carboxymethyl cellulose (CMC · Na) were purchased from Nacalai Tesque (Tokyo, Japan). Sodium cromoglycate (SCG) was purchased from Funakoshi (Tokyo, Japan). Compound 48/80, dimethyl sodium salt (DMSO), prednisolone, monoclonal anti-DNP antibody and heparin sodium salt were purchased from Sigma (St. Louis, MO, U.S.A.). Other chemical reagents were reagent grade and were purchased from Wako Pure Chemical Industries, Ltd. unless otherwise noted.Preparation of PN-ext and Fractionation Methanolic extract of Piper nigrum leaf (PN-ext) was obtained according to the previous paper in yield of 14.0%. The powdered dry leaves (500 g) of P. nigrum were extracted with MeOH (5 lϫ3 times) for 1 h under reflux. Combined extracts were evaporated under reduced pressure to give a methanolic extract (PN-ext, 71.1 g). A part of PN-ext (69.6 g) was extracted with hexane (400 mlϫ3), and the organic layer was evaporated to give a hexane soluble fraction (17.3 g). The hexane insoluble part was extracted with EtOAc (300 mlϫ2). The E...

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Histamine Release Inhibitory Activity of Piper nigrum Leaf

Hirata

Naruto

Inaba

et al. 2008

Biological & Pharmaceutical Bulletin

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“…nigrum and fruit of P . cubeba revealed strong inhibiting activity in the concentration of 2 mg/ml [11].…”

Section: Plant Raw Materialsmentioning

confidence: 95%

“…Moreover, 5% solution of methanol extract from P . Nigrum leaves, applied locally during the in vivo test of hair growth in mice responsive to testosterone, revealed strong antiandrogenic properties [11].…”

Section: Plant Raw Materialsmentioning

confidence: 99%

Plants as potential active components in treatment of androgenetic alopecia

et al. 2014

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S u m m a r yAndrogenetic alopecia is caused by the influence of sex hormones on hair follicles and by hereditary factors. Characteristic for that type of alopecia is shortening of the hair growth phase and elongation of the rest phase caused by disturbance of the process of transformation of testosterone into dihydrotestosterone. Treatment of that type of alopecia involves 5α-reductase inhibitors, antagonists of the androgenic receptor or stimulating proliferation of cells to induce the hair growth. A number of plant raw materials work that way, thus they can be used in treatment of this type of alopecia.

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Promotion of Hair Growth by Rosmarinus officinalis Leaf Extract

Murata

Noguchi

Kondo³

et al. 2012

Phytotherapy Research

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Topical administration of Rosmarinus officinalis leaf extract (RO-ext, 2 mg/day/mouse) improved hair regrowth in C57BL/6NCrSlc mice that experienced hair regrowth interruption induced by testosterone treatment. In addition, RO-ext promoted hair growth in C3H/He mice that had their dorsal areas shaved. To investigate the antiandrogenic activity mechanism of RO-ext, we focused on inhibition of testosterone 5α-reductase, which is well recognized as one of the most effective strategies for the treatment of androgenic alopecia. RO-ext showed inhibitory activity of 82.4% and 94.6% at 200 and 500 µg/mL, respectively. As an active constituent of 5α-reductase inhibition, 12-methoxycarnosic acid was identified with activity-guided fractionation. In addition, the extract of R. officinalis and 12-methoxycarnosic acid inhibited androgen-dependent proliferation of LNCaP cells as 64.5% and 66.7% at 5 µg/mL and 5 μM, respectively. These results suggest that they inhibit the binding of dihydrotestosterone to androgen receptors. Consequently, RO-ext is a promising crude drug for hair growth.

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Testosterone 5.ALPHA.-Reductase Inhibitory Active Constituents of Piper nigrum Leaf

Abstract: dition, the P. nigrum leaf extract showed in vivo anti-androgenic activity using the hair regrowth assay in testosterone sensitive male C57Black/6CrSlc strain mice.

Cited by 42 publications

References 19 publications

Histamine Release Inhibitory Activity of Piper nigrum Leaf

Histamine Release Inhibitory Activity of Piper nigrum Leaf

Plants as potential active components in treatment of androgenetic alopecia

Promotion of Hair Growth by Rosmarinus officinalis Leaf Extract

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