New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Tang, Rong; Zhang, Yaqiong; Hu, Dawei; Yang, Xuefei; Yang, Jun; San, Myint Myint; Oo, Thaung Naing; Kong, Yi; Wang, Yue‐Hu

doi:10.1007/s13659-019-0208-z

Cited by 7 publications

(9 citation statements)

References 41 publications

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“…Identification of the constituents in P. retrofractum fruit extracts was conducted previously with various detection methods based on chemical and spectroscopic evidence. Several compounds such as piperine, piperodione, methyl piperate, oleic acid, glucosides, (2E,12E)-pipertridecadienamide, N-isobutyl-(2E,4E,10Z)-hexadeca-2,4,10-trienamide, N-isobutyleicos-2,14-dienamide, dipiperamides, (E)-N-cinnamoyl-2-methoxypiperidine and (R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one were recognized from P. retrofractum fruit (Kubo et al ., 2013; Muharini et al ., 2015; Tang et al ., 2019). It is evident that the chemical constituents identified from various extracts of P. retrofractum fruit, as reported in the present and previous studies, varied qualitatively and quantitatively.…”

Section: Discussionmentioning

confidence: 99%

Nematocidal effect of Piper retrofractum Vahl on morphology and ultrastructure of Strongyloides stercoralis third-stage infective larvae

et al. 2020

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In a previous research work aimed at discovering natural helminthicides as alternatives to conventional synthetic drugs, Piper retrofractum fruit hexane extract (PHE) has been shown to possess promising nematocidal activity against the third-stage infective larvae of Strongyloides stercoralis. Thus, this study was designed to evaluate the chemical composition and the impact of PHE on symptom and structural alterations of S. stercoralis. Chemical analysis of PHE by gas chromatography–mass spectrometry demonstrated 26 different compounds, constituting 100% of the total composition. The main components were 4-acetylphenyl (4-benzoylphenoxy) acetate (14.86%) and octyl methoxycinnamate (12.72%). Nematocidal bioassays revealed promising potential of PHE against S. stercoralis larvae, with an LC50 value of 0.059 mg/ml, while the reference drug ivermectin exerted higher efficacy, with an LC50 value of 0.020 µg/ml. Behavioural observations under light microscopy revealed that PHE-treated S. stercoralis larvae moved slowly, became paralysed and eventually died during 24 h of incubation. The dead larvae appeared under light microscope as straight worms with unknown vacuoles of different sizes inside their internal bodies. Morphological alterations of the PHE-treated S. stercoralis larvae, such as straight bodies with swollen cuticle, faded transverse annulations and faded longitudinal striations, as well as shallow and smooth lateral longitudinal grooves, were seen clearly under scanning electron microscopy. Ultrastructural changes in the treated larvae, such as protruded lateral longitudinal grooves, loose muscle with vacuolation, dissociation between the hypodermis and cuticle and marked intracellular disorganization with vacuolation, were detected under transmission electron microscopy. The results of this study provide evidence that PHE is toxic against S. stercoralis and also a potential new alternative for anti-Strongyloides chemotherapy.

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Section: Discussionmentioning

confidence: 99%

Nematocidal effect of Piper retrofractum Vahl on morphology and ultrastructure of Strongyloides stercoralis third-stage infective larvae

et al. 2020

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“…Kandungan senyawa piperine dalam P. retrofractum lebih rendah dari P. nigrum namun lebih tinggi dari P. betle (Rajophadye et al, 2011). Hasil penelitian yang dilakukan oleh Tang (Tang et al, 2019) (Jamal et al, 2013) Gambar 3. Struktur senyawa baru amida glikosida tanaman P. retrofractum (Tang et al, 2019) Gambar 4.…”

Section: Penggunaan Tradisionalunclassified

“…Hasil penelitian yang dilakukan oleh Tang (Tang et al, 2019) (Jamal et al, 2013) Gambar 3. Struktur senyawa baru amida glikosida tanaman P. retrofractum (Tang et al, 2019) Gambar 4. Struktur seyawa baru fenilpropanoid glikosida tanaman P. retrofractum (Tang et al, 2019) Gambar 5.…”

Section: Penggunaan Tradisionalunclassified

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Cabe Jawa (Piper retrofractum Vahl.) : PENGGUNAAN TRADISIONAL, FITOKIMIA dan AKTIVITAS FARMAKOLOGI Piper retrofractum Vahl. : Traditional Uses, Phytochemical and Pharmacological Activities

Faramayuda

Arifin

Syam

et al. 2021

PSP

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ABSTRAK Cabe jawa (Piper retrofractum Vahl.) adalah tanaman daerah tropis asli Indonesia yang dijumpai juga di negara Asia Tenggara seperti Thailand dan Malaysia, dan sejak dahulu telah digunakan secara turun-temurun sebagai bahan tambahan makanan ataupun obat tradisional. Secara tradisional di masyarakat, buah cabe jawa dapat digunakan dalam ramuan untuk mengobati demam, perut kembung, mulas, muntah, mengatasi gangguan pencernaan, merangsang nafsu makan, dan lemah syahwat. Akarnya sering digunakan untuk mengobati sakit gigi, luka dan kejang, serta bagian daunnya digunakan juga untuk obat kumur. Beberapa penelitian menyebutkan aktivitas farmakologi cabe Jawa memiliki efek afrodisiaka, antipiretik, antihiperurisemia, antikanker, dan antimikroba. Pengujian klinis terhadap cabe jawa telah dilakukan dan potensial dikembangkan menjadi obat tradisional golongan fitofarmaka. Cabe jawa memiliki aktivitas sebagai imunostimulan, lebih tinggi dibandingkan dengan kelompok imunostimulan fitofarmaka. Cabe jawa mempunyai potensi sebagai anti-photoaging, aktivitas antituberkular, antiproliferasi, aktivitas larvasida, dan aktivitas sitotoksik. Studi fitokimia senyawa metabolit sekunder utama yang terkandung dalam cabe jawa antara lain beberapa jenis alkaloid seperti piperine, pipernonaline, guineensine, piperoctadecalidine, minyak atsiri buah cabe jawa mengandung tiga komponen utama yaitu yaitu β-caryophyllene (17%), pentadecane (17,8%) dan β- bisabollene (11,2%) . Selain senyawa utama tersebut, terdapat senyawa baru pada buah cabe jawa, diantaranya; senyawa amida, amida glikosida, fenilpropanoid glikosida, dan alkaloid. Sebagai afrodisiaka bagian yang digunakan adalah buahnya dan senyawa piperin yang diduga bertanggung jawab terhadap aktivitas tersebut. Piperin merupakan senyawa utama dan zat berkhasiat yang terkandung dalam buah cabe jawa dan berfungsi sebagai penurun demam, mengurangi rasa sakit, antioksidan, mengurangi peradangan, antitumor, dan sebagai imunomodulator. Berdasarkan aktifitas farmakologi yang baik dari cabe jawa maka studi atau penelitian-penelitian pada tanaman ini harus terus dilakukan seperti pengembangan formulasi dan upaya perbanyakan tanaman karena populasi cabe jawa jumlahnya terbatas. Media terbaik dalam induksi kalus tanaman cabe jawa adalah Murrashige Skoog (MS) yang ditambah 6-Benzil Amino Purin (BAP) dan Naphtalene Acetic Acid (NAA).ABSTRACT Piper retrofractum vahl. is a tropical plant native to Indonesia which is also found in Southeast Asian countries such as Thailand and Malaysia, and has been used for generations as a food additive or traditional medicine. Traditionally in the community, P. retrofractum fruit can be used in potions to treat fever, flatulence, heartburn, vomiting, overcome digestive disorders, stimulate appetite, and impotence. The roots are often used to treat toothaches, wounds, and seizures, and the leaves are also used for mouthwash. Several studies have stated that the pharmacological activity of P. retrofractum has aphrodisiac, antipyretic, anticancer, and antimicrobial effects. Clinical testing on P. retrofractum has been carried out and has the potential to be developed into a traditional medicine of the phytopharmaceutical class. P. retrofractum has activity as an immunostimulant, which is higher than the phytopharmaceutical immunostimulant group. P. retrofractum has potential as anti-photoaging, antitubercular, antiproliferative, larvicidal activity, and cytotoxic activity. Phytochemical studies of the main secondary metabolites contained in P. rectofractum include several types of alkaloids such as piperine, pipernonaline, guineensine, piperoctadecalidine, fruit essential oils. Javanese chili contains three main components, namely-caryophyllene (17%), pentadecane (17.8%) and -bisabollene (11.2%). In addition to these main compounds, there are new compounds in P. retrofractum fruit, including; amide compounds, amide glucosides, phenylpropanoid glucosides, and alkaloids. As an aphrodisiac, the part used is the fruit and the piperine compound which is thought to be responsible for this activity. Piperine is the main compound and efficacious substance contained in P. retrofractum fruit and functions as a fever reducer, pain reliever, antioxidant, reducing inflammation, antitumor, and immunomodulator. Based on the good pharmacological activity of P. retrofractum , studies or researches on this plant must continue to be carried out such as formulation development and plant propagation efforts because the population of P. retrofractum is limited. The best medium for callus induction of cabe jawa was Murashige Skoog (MS) with 6-Benzyl Amino Purine (BAP) and Naphtalene acetic (NAA) added.

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“…P. retrofractum also has quite some fruit branches, with a round shape and green, dark green (Haryudin & Rostiana., 2015). According to research conducted by Tang in 2019, there are new compounds contained in the P. retrofractum plant, which are two amide compounds; (E) -N-cinnamoyl-2-methoxypiperidine and (R)-1-(2-oxopyrrolidine-3-yl)-5,6-dihydropyridine-2 (1H) -one, four amide compounds glucoside; retrofractosides AD, and two phenylpropanoid glycoside compounds; retrofractosides E and F ( Tang et al, 2019;Muharini et al, 2015;Jadid et al, 2018;Musthapa et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Identification Secondary Metabolites From Callus Piper retrofractum Vahl

Faramayuda

Permana

Syam

et al. 2021

EKW

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Javanese chili (Piper retrofractum Vahl) is a traditional medicinal plant originating from Indonesia and has many pharmacological activities, one of which is often used as a base for aphrodisiac herbal medicine. The population of P. retrofractum is limited, so it is necessary to design secondary metabolite production and propagation efforts using plant tissue culture techniques. The materials used in this study were explants of P. retrofractum leaves that were induced in Murashige and Skoog (MS) media and the ratio of growth regulators 2.4-dichlorophenoxyacetis acid (2,4-D): Benzyl Amino Purine (BAP) 0.5: 0.5. The results showed that the callus of P. retrofractum was formed in the growth regulator 2.4D: BAP (0.5: 0.5). TLC and spectrophotometry identified the secondary metabolite content of callus. Secondary metabolite analysis using the thin layer chromatography (TLC) method using the mobile phase ethyl acetate: n-hexane (7: 3) showed a terpenoid compound indicated by purple spots on the visual appearance after spraying 10% spotting vanillin. Identification using infrared spectrophotometry shows functional groups -CH, C = O, C = C, -CH2, and -CH3, characteristic of terpenoid compounds. Based on TLC data and spectrophotometry, callus P. retrofractum is thought to contain terpenoid compounds. This study's results are expected to be the basis for developing secondary metabolite production in P. retrofractum with cell suspension culture and P. retrofractum propagation by micropropagation.Abstrak: Cabai Jawa (Piper retrofractum Vahl) merupakan tanaman obat tradisional yang berasal dari Indonesia dan banyak memiliki aktivitas farmakologis salah satunya sering digunakan sebagai bahan dasar jamu afrodisiaka. Populasi tanaman cabai Jawa terbatas maka perlu dirancang upaya produksi metabolit sekunder dan upaya perbanyakan tanaman cabai Jawa salah satunya menggunakan teknik kultur jaringan tanaman. Bahan yang digunakan pada penelitian ini adalah eksplan daun tanaman cabai Jawa yang diinduksi pada media Murashige and Skoog (MS) dan perbandingan zat pengatur tumbuh 2.4-dichlorophenoxyacetis acid (2,4-D) : Benzyl Amino Purine (BAP) 0,5 : 0,5. Hasil penelitian menunjukkan bahwa kalus cabai Jawa terbentuk dalam zat pengatur tumbuh 2,4D: BAP (0,5: 0,5). Kandungan metabolit sekunder dari kalus diidentifikasi dengan KLT dan spektrofotometri. Analisis metabolit sekunder menggunakan metode kromatografi lapis tipis (KLT) menggunakan fasa gerak etil asetat: n-heksana (7: 3) menunjukkan adanya senyawa terpenoid yang ditunjukkan dengan adanya bercak ungu pada penampakan visual setelah disemprotkan spotting vanilin 10%. Hasil Identifikasi menggunakan spektrofotometri UV-Vis menunjukkan isolat mempunyai panjang gelombang maksimum 272,6 nm. Identifikasi menggunakan spektrofotometri inframerah menunjukkan adanya gugus fungsi -CH, C = O, C = C, -CH2, dan -CH3 yang merupakan ciri khas senyawa terpenoid . Berdasarkan data KLT dan spektrofotometri kalus cabai Jawa diduga mengandung senyawa terpenoid. Hasil penelitian ini diharapkan dapat menjadi dasar pemgembangan produksi metabolit sekunder dalam tanaman cabai Jawa dengan kultur suspensi sel dan perbanyakan tanaman cabai Jawa dengan mikropropagasi.

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New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Abstract: Two new amides ( E )- N -cinnamoyl-2-methoxypiperidine ( 1 ) and ( R )-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1 H )-one ( 2 ), four new amide glucosides, retrofractosides A–D ( 3 – 6 ), and two new phenylpropanoid glucosides, retrofractosides E ( 7 ) and F ( … Show more

Cited by 7 publications

References 41 publications

Nematocidal effect of Piper retrofractum Vahl on morphology and ultrastructure of Strongyloides stercoralis third-stage infective larvae

Nematocidal effect of Piper retrofractum Vahl on morphology and ultrastructure of Strongyloides stercoralis third-stage infective larvae

Cabe Jawa (Piper retrofractum Vahl.) : PENGGUNAAN TRADISIONAL, FITOKIMIA dan AKTIVITAS FARMAKOLOGI Piper retrofractum Vahl. : Traditional Uses, Phytochemical and Pharmacological Activities

Identification Secondary Metabolites From Callus Piper retrofractum Vahl

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