Structures and Syntheses of Two Phenolic Amides from<i>Piper nigrum</i>L.

Nakatani, Nobuji; Inatani, Reiko; Fuwa, Hidetsugu

doi:10.1080/00021369.1980.10864411

Cited by 19 publications

(6 citation statements)

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“…The HRESIMS spectrum showed a deprotonated molecule of m / z 403.1380 (calcd for 403.1393), corresponding to a molecular formula of C 21 H 24 O 8 containing 10 degrees of unsaturation. The 1 H and 13 C NMR spectral data of 1 were found to be similar to those of p -hydroxyphenethyl trans -ferulate ( 5 ), which in turn was identified by comparison of its NMR data with literature data. ,, A fragment ion of m / z 193 in the CID product ion spectrum suggested the presence of a feruloyl unit. , The 1 H NMR spectrum of 1 displayed signals at δ 7.588 (1H, d, J = 16.0 Hz) and 6.322 (1H, d, J = 16.0 Hz), indicating the presence of two trans -coupled olefinic protons, and signals at δ 3.929 (3H, s), 3.889 (3H, s), and 3.278 (3H, s) attributable to three methoxyl groups. In addition, two sets of 1,3,4-trisubstituted phenyl units (ABX system) were revealed by signals at δ 7.061 (1H, dd, J = 8.2, 2.0 Hz), 7.030 (1H, d, J = 2.0 Hz), 6.915 (1H, d, J = 8.2 Hz), 6.905 (1H, d, J = 8.6 Hz), 6.810 (1H, d, J = 2.0 Hz), and 6.806 (1H, dd, J = 8.6, 2.0 Hz) and confirmed by the COSY spectrum.…”

Section: Resultsmentioning

confidence: 69%

Serotonergic Activity-Guided Phytochemical Investigation of the Roots of Angelica sinensis

et al. 2006

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Serotonin receptor (5-HT 7 ) binding assay-directed fractionation of a methanol extract of the dried roots of Angelica sinensis (Apiaceae) led to the isolation and identification of twenty-one compounds including a new phenolic ester, angeliferulate (1), and three new phthalides, 10-angeloylbutylphthalide (2), sinaspirolide (3) and ansaspirolide (4), along with seventeen known compounds, p-hydroxyphenethyl trans-ferulate (5), Z-ligustilide (6), Z-butylidenephthalide (7), senkyunolide I (8), Z-6-hydroxy-7-methoxy-dihydroligustilide (9), N-butylbenzenesulphonamide (10), 11(S),16(R)-dihydroxy-octadeca-9Z,17-dien-12,14-diyn-1-yl acetate (11), (3R,8S)-falcarindiol (12), heptadeca-1-ene-9,10-epoxy-4,6-diyne-3,8-diol (13), oplopandiol (14), 8-hydroxy-1-methoxy-, Z-9-heptadecene-4,6-diyn-3-one (15), imperatorin, ferulic acid, vanillin, stigmasterol, sucrose, and 1,3-di-linolenin. This is the first report of a sulfonamide (10) identified from a higher plant source, although its presence needs further investigation. Biosynthetic pathways for dimeric phthalides 3 and 4 are proposed. Compound 5, 7, 11, 12, 15, and imperatorin exhibited affinity toward 5-HT 7 receptors in a competitive binding assay.Angelica sinensis (Oliv.) Diels (Apiaceae) is an herbaceous perennial plant mainly distributed in the northwest of China. The root is variously called Dang Gui or Dong Quai, among others. It has been traditionally applied to the treatment of gynecological disorders (e.g. menstrual disorders, amenorrhea, dysmenorrhea, anemia, premenstrual syndrome, menopause) for thousands of years in Asia, with the earliest record of its use in the Divine Husbandman's Classic of the Materia Medica (Shen Nong Ben Cao Jing) published during the period of the Han Dynasty (AD 25-225). 1-3 Dang Gui has been regarded as "lady's ginseng" or "female's ginseng", implicating its popularity and importance for various women's ailments. It was first introduced into the West in 1899 by Merck in the form of a liquid extract named "Eumenol", 4 and is presently marketed in the USA as a dietary supplement, with numerous products being marketed worldwide.It was generally presumed that Dang Gui has estrogenic activity based on its broad applications for female ailments. However, there is no evidence of estrogenicity in both in vitro and clinical studies, 5,6 which indicates that Dang Gui may act through an alternative mechanism rather than being a phytoestrogen. Indeed, preliminary testing of extracts demonstrated that the methanol extract of Dang Gui has serotonergic activity, suggesting that it may contain serotonergic ligands that act on serotonin receptors and, thus, exhibit pharmacological effects related to improvement of symptoms of moods, behaviors and hot flashes for premenstrual and menopausal women.

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Section: Resultsmentioning

confidence: 69%

Serotonergic Activity-Guided Phytochemical Investigation of the Roots of Angelica sinensis

et al. 2006

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“…The methylene chloride extract of the fruits of white pepper was separated in the same way described previously. 6 (64), 72 (4), 57 (16), 43 (10). These data were identical with those of synthetic pellitorine and the mixed melting point showedno depression.…”

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confidence: 99%

Constituents of pepper. part III. Isobutyl amides from pepper (Piper nigrum L.).

Nakatani

Inatani

1981

Agricultural and Biological Chemistry

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“…Identification of known compounds was done on the basis of the spectroscopic data and comparisons with those found in the literature as achilleamide ( 1 ), 2,4-( E , E )-dodecadienyl piperidide ( 2 ), 1-cinnamoylpiperidine ( 4 ), N - trans -feruloyl piperidine ( 5 ), coumaperine ( 6 ), piperanine ( 7 ), piperoleine A ( 8 ), piperoleine B ( 9 ), piperine ( 11 ), pipernonaline ( 12 ), piperchabamide B ( 13 ), piperchabamide C ( 14 ), piperettine ( 15 ), dehydropipernonaline ( 16 ), (2 E ,4 E ,12 E )-13-(3,4-methylenedioxyphenyl)-1-(1-piperidinyl)-2,4,12-tridecatrien-1-one ( 17 ), tricholeine ( 18 ), piperyline ( 19 ), brachyamide B ( 20 ), 1-[(2 E ,10 E )-11-(3,4-methylenedioxyphenyl)-2,10-undecenoyl]pyrrolidine ( 21 ), piperettyline ( 22 ), 6,7-dehydrobrachyamide B ( 23 ), 1-[(2 E ,4 E ,10 E )-11-(3,4-methylenedioxyphenyl)-2,4,10-undecatrienoyl]pyrrolidine ( 24 ), brachyamide A ( 25 ), pellitorine ( 26 ), kalecide ( 27 ), N -isobutyl-(2 E ,4 E )-hexadecadienamide ( 28 ), N -isobutyl-(2 E ,4 E )-octadecadienamide ( 29 ), N -isobutyl-(2 E ,4 E ,12 Z )-octadeca-2,4,12-trienamide ( 30 ), N -isobutyl-(2 E ,4 E ,14 Z )-eicosa-2,4,14-trienamide ( 31 ), piperlonguminine ( 32 ), piperchabamide D ( 33 ), retrofractamide A ( 34 ), retrofractamide B ( 35 ), guineensine ( 36 ), brachystamide B ( 37 ), feruloyltyramine ( 39 ), N - trans -feruloyldopamine ( 40 ), (2 E ,4 E )-5-(3,4-methylenedioxyphenyl)-2,4-pentadienal ( 45 ), piperic acid ( 46 ), methyl piperate ( 47 ), (+)-bornyl piperate ( 49 ), (6 E )-7-(3,4-methylenedioxyphenyl)-heptenoic acid ( 50 ), (8 E )-9-(3,4-methylenedioxyphenyl)-nonenoic acid ( 51 ), cubebinol ( 52 ), (−)-dehydrodiconiferyl alcohol ( 53 ), (−)-secoisolariciresinol ( 54 ), and (2 R ,3 R )-2-[(3,4-dimethoxyphenyl)methyl]-3-[(3,4,5-trimethoxyphenyl)methyl]-1,4-butanediol ( 55 ) …”

Section: Resultsmentioning

confidence: 99%

Alkaloids from Black Pepper (Piper nigrum L.) Exhibit Anti-Inflammatory Activity in Murine Macrophages by Inhibiting Activation of NF-κB Pathway

Pei

Xue

Tang

et al. 2020

J. Agric. Food Chem.

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Black pepper (Piper nigrum L.) has been commonly utilized in food preparation and traditional medicine in several countries. Seven new amide alkaloids, pipernigramides A–G (3, 10, 38, and 41–44), a new piperic ester, pipernigrester A (48), along with 47 known compounds were isolated from the EtOH extract of P. nigrum. The inhibitory effects on nitric oxide (NO) of all compounds were then evaluated. Among the tested compounds, three of them (42–44) significantly inhibited inducible nitric oxide synthase (iNOS)-mediated NO (IC50 = 4.74 ± 0.18, 4.08 ± 0.19, and 3.71 ± 0.32 μM, respectively), and IL-1β, IL-6, TNF-α, and PGE2 release in RAW 264.7 cells stimulated by lipopolysaccharide. Moreover, 42–44 suppressed IκB degradation and further inhibited the cytosol-nucleus translocation of the p65 subunit by targeting IKK-β. In the carrageenan-induced paw edema test, 42–44 demonstrated anti-inflammatory effects as well. These results indicate that all three compounds from P.nigrum have the potential anti-inflammatory effects.

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Structures and Syntheses of Two Phenolic Amides fromPiper nigrumL.

Cited by 19 publications

References 3 publications

Serotonergic Activity-Guided Phytochemical Investigation of the Roots of Angelica sinensis

Serotonergic Activity-Guided Phytochemical Investigation of the Roots of Angelica sinensis

Constituents of pepper. part III. Isobutyl amides from pepper (Piper nigrum L.).

Alkaloids from Black Pepper (Piper nigrum L.) Exhibit Anti-Inflammatory Activity in Murine Macrophages by Inhibiting Activation of NF-κB Pathway

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