Three phenyldihydronaphthalene lignanamides from fruits of Cannabis sativa

Sakakibara, Iwao; Ikeya, Yukinobu; Hayashi, Kôji; Mitsuhashi, Hiroshi

doi:10.1016/0031-9422(92)83479-i

Cited by 87 publications

(54 citation statements)

References 8 publications

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“…HMBC Correlations from the anomeric H-atom to C(1'') indicated a 1'-O-1'' linkage between the sugar moiety and the benzene ring. The correlation of HÀC(6')/C (15) suggested that the carboxy group of the dihydrophaseic acid moiety was connected to C(6') of the sugar unit by an ester bond. The two MeO groups (d(H) 3.72 and 3.79) were connected to C(4'') and C(5''), respectively, as shown by HMBC and ROESY experiments.…”

Section: Results Andmentioning

confidence: 97%

“…The aporphine alkaloids were previously reported from Mitrephora genus [7], the existence of cinnamic acid amide derivatives in this genus is reported here for the first time. It is known from the literature that the dimerization of cinnamic acid amides is a common phenomenon in higher plants [8] [10] [12] [13] [15]. For example, grossamide and cannabisin G and F are all dimerized from two cinnamic acid amides possessing coupling sites at 8 -8, 8 -5, and 8-O-4, respectively.…”

Section: Results Andmentioning

confidence: 99%

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Lignanamides and Sesquiterpenoids from Stems of Mitrephora thorelii

Tang

Yang

2008

Helvetica Chimica Acta

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The first phytochemical investigation on stems of Mitrephora thorelii led to the isolation of three new lignanamides, thoreliamides A -C (1 -3), and a new sesquiterpenoid, thorelinin (4), together with ten known compounds. The structures of the new compounds were established on the basis of extensive spectroscopic analyses. Thoreliamide C is the first trimer derived from cinnamic acid amide units.Introduction. -The genus Mitrephora (Annonaceae), including ca. 40 species, is distributed widely throughout tropical areas in Asia. Some plants of this genus have been used as a tonic traditional medicine in Thailand [1]. So far, five species, i.e., M., and M. zippeliana [6] have been investigated. Alkaloids from M. maingayi possessing an unprecedented skeleton and diterpenoids from M. glabra bearing a novel skeleton have been successively reported. The potent and broad anticancer activity of the diterpenoids attracted us to further investigate another species of this genus, Mitrephora thorelii Pierre, distributed in southwest China.Our first phytochemical study reported here led to the isolation and characterization of three new lignanamides, thoreliamides A -C (1 -3, resp.), and a new sesquiterpene, thorelinin (4), along with ten known compounds, liriodenine, oxoputerine, N-trans-sinapoyltyramine, N-trans-feruloyltyramine, N-trans-caffeoyltyramine [7], N-trans-feruloyldopamine, N-trans-feruloyl-3-methyldopamine [8], N-p-coumaroyltyramine [9], cannabisin G, and cannabisin F [10] from stems of M. thorelii. Thoreliamide C (3) is the first cinnamic acid amide trimer reported from the plant kingdom. The structure elucidation of 1 -4 was accomplished on the basis of spectroscopic data, especially 2D-NMR.

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Section: Results Andmentioning

confidence: 97%

Section: Results Andmentioning

confidence: 99%

Lignanamides and Sesquiterpenoids from Stems of Mitrephora thorelii

Tang

Yang

2008

Helvetica Chimica Acta

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“…Hempseed cakes, the by-products of this industry, are not currently considered as having high economic added value. But hempseed and its residue are sources of amide compounds derived from caffeic acid [10][11][12][13], among which some possess predominant radical scavenging activity [14]. With the aim to find novel natural compounds useful for the development of new treatments, we performed a biological and phytochemistry study of the extracts from hempseed cakes.…”

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confidence: 99%

“…It was previously obtained by semisynthesis from cannabisin A by an acid treatment under strong conditions [Pyridine/HBr (48 %), 90°C during 2 days] [10]. The other purified compounds were identified as cannabisins A [10], B [11], C [11], F [12], M [14], 3,3′-demethylgrossamide [15], grossamide [10], N-trans-caffeoyltyramine [16], and N-trans-caffeoyloctopamine [17] by direct comparison of their spectral data with those in the literature. Compound 1, cannabisins B, F, and M, 3,3′-demethylgrossamide, and N-trans-caffeoyltyramine were first screened for their potential arginase inhibitory property at 10 and 100 µM on purified liver bovine arginase.…”

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confidence: 99%

In Vitro Mammalian Arginase Inhibitory and Antioxidant Effects of Amide Derivatives Isolated from the Hempseed Cakes (Cannabis sativa)

Bourjot

Zedet

Demange

et al. 2017

PMIO

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!In an effort to identify novel inhibitors of arginase, a phytochemical study was performed on hempseed cakes (Cannabis sativa L.). It led to the isolation of a new lignanamide, cannabisin I (1), together with seven known lignanamides, cannabisins A, B, C, F, M, 3,3′-demethylgrossamide, grossamide, and two phenylpropanoid amides, N-trans-caffeoyltyramine and N-trans-caffeoyloctopamine, among which was later identified for the first time from C. sativa. Their structures were elucidated by comprehensive analysis of NMR spectroscopy and mass spectrometry data. These compounds were evaluated on mammal arginase (purified liver bovine arginase), showing that N-trans-caffeoyltyramine exhibited the higher activity with an IC 50 value of 20.9 µM, which remains, however, less active than the reference compound S-(2-boronoethyl)-l-cysteine (IC 50 = 4.3 µM). Radical scavenging capacity of these compounds was determined by the ORAC-FL method. All tested cannabisins displayed antioxidant activity close to or better than the reference compounds. N-trans-Caffeoyltyramine has both arginase inhibitory property and antioxidant capacity.

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“…20 Cannabisin C and negundin B are dihydronaphthalene natural products found in the roots of cannabis sativa and vitex negundo , respectively. 21 (+)-Phyltetralin was one of five constituents isolated from pkyllantkus niruri , which has been used in the treatment of jaundice, asthma, and bronchial infections. 22 Previously, several approaches have been reported to access substituted 1,2-dihydronaphthalene structures.…”

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confidence: 99%

Enantioselective Synthesis of 1,2-Dihydronaphthalene-1-carbaldehydes by Addition of Boronates to Isochromene Acetals Catalyzed by Tartaric Acid

et al. 2015

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Tartaric acid is an ideal asymmetric catalyst as it is abundant, cheap, and environmentally friendly. (+)-Tartaric acid was found to catalyze a novel enantioselective [4 + 2] cycloaddition of isochromene acetals and vinylboronates. A variety of substituted isochromene acetals were tolerated, furnishing the desired dihydronaphthalenes and dihydrobenzofluorene products in good yields. High enantiomeric ratios (up to 98.5:1.5) and excellent diastereoselectivities (all >99:1) were observed employing 10 mol % of (+)-tartaric acid as the catalyst, in combination with 5 mol % of Ho(OTf)3.

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Three phenyldihydronaphthalene lignanamides from fruits of Cannabis sativa

Cited by 87 publications

References 8 publications

Lignanamides and Sesquiterpenoids from Stems of Mitrephora thorelii

Lignanamides and Sesquiterpenoids from Stems of Mitrephora thorelii

In Vitro Mammalian Arginase Inhibitory and Antioxidant Effects of Amide Derivatives Isolated from the Hempseed Cakes (Cannabis sativa)

Enantioselective Synthesis of 1,2-Dihydronaphthalene-1-carbaldehydes by Addition of Boronates to Isochromene Acetals Catalyzed by Tartaric Acid

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