Main constituents and cytotoxic activity of the essential oil of Piper artanthe

Abstract

The identification of novel antitumor agents that demonstrate efficacy is necessary to improve medical treatment based on new drugs. The pharmaceutical industries have been working together in this area for several years to try to find novel compounds with good antitumor activity. Brine shrimp (Artemia salina) larvae have been reported as an organism that can detect bioactive compounds. Since there is a good correlation between the toxicity on Artemia salina and antitumor [1, 2], phototoxicity [3], and anti-Trypanosoma cruzi [4] activity, this test is a good prescreening method for identifying new potential antitumor agents.Piper artanthe C.DC. (Piperaceae) is commonly known as the "cordoncillo." It is a shrub or small tree growing to 1 to 2 m, and it is widespread in America [5] and used in folk medicine for the treatment of different disease symptoms. Despite phytochemical studies on the Piper species describing the isolation of several bioactive compounds [6], to our knowledge P. artanthe has not been investigated for its biological activity, and no data can be found concerning the chemical composition of this species.The main purpose of this study was not only to evaluate the biological activities using the Artemia salina toxicity model as a prescreening procedure but also to evaluate the composition and structural characterization of the main components of the essential oil from the aerial parts of P. artanthe C.DC.As shown in Table 1, 41 compounds consisting of more than 87% of the total hydrodistilled essential oil were identified. The chromatographic data on both columns, HP-5MS and DB-1, indicate that the major components were apiol (14.52%), G-elemene (11.69%), (E)-caryophyllene (10.24%), epi-cubebol (8.85%), myristicin (6.38%), and cubebol (6.30%). Over 44% of these compounds were sesquiterpenes, and 45% of them were oxygenated sesquiterpenes.The evaluation of biological activity using the brine shrimp lethality test showed that the essential oil of the fresh aerial parts of P. artanthe displayed an LC 50 value of 107.1 Pg/mL (V n-1 : 8.9 Pg/mL). According to [7], crude extracts resulting in LC 50 values of less than 250 Pg/mL are considered significantly active. For that reason, this oil can be regarded as a promising candidate for further investigation. Accordingly, our following objective was to isolate and identify the major components of this essential oil in order to evaluate their individual biological activities. Though all constituents could not be isolated, the main component was made pure by means of column chromatography on silica gel as a yellowish oil (980 mg). This compound displayed an LC 50 value of 13.1 Pg/mL (V n-1 : 0.4 Pg/mL). Plant polyalkoxybenzenes display a broad spectrum of biological activities. For example, apiol has previously been reported to be a specific inhibitor of the biosynthesis of aflatoxin G1, a calcium antagonist, and a diuretic, abortive, sedative, antioxidant, and insecticidal agent >8-11@.1 H NMR spectrum analysis indicated that the main component isolated fro...

Essential Oils from Neotropical Piper Species and Their Biological Activities

“… Rondônia state, Brazil Leaf (SD) Octanal (5.5%), germacrene D (72.9%), γ-elemene (6.8%) c --- [ 112 ] P. artanthe C. DC. San Migues, Santander, Colombia Aerial parts (HD) δ-Elemene (11.7%), β-caryophyllene (10.2%), epi -cubebol (8.9%), cubebol (6.3%), myristicin (6.4%), apiole (14.5%) --- [ 113 ] P. augustum Rudge Reserva Biológica Alberto Manuel Brenes, Costa Rica Leaf (HD) α-Pinene (10.5%), α-phellandrene (14.7%), limonene (13.0%), β-phellandrene (5.6%), linalool (10.3%), β-caryophyllene (13.5%) --- [ 114 ] P. augustum Rudge Valle de Anton, Cerro Caracoral, Cocle, Panama Leaf (HD) α-Pinene (6.0%), β-elemene (12.3%), cembrene (11.7%), cembratrienol 1 (25.4%), cembratrienol 2 (8.6%) --- [ 47 ] P. auritum Kunth Boca de Uracillo, Colon Province, Panama Leaf (HD) Safrole (70%) --- [ 115 ] P. auritum Kunth Güira de Melena, Cuba Leaf (HD) Safrole (64.5%) --- [ 116 ] …”

Secondary Metabolic Profile as a Tool for Distinction and Characterization of Cultivars of Black Pepper (Piper nigrum L.) Cultivated in Pará State, Brazil

“…The other main constituents identified in the cultivar were ( E )-β-caryophyllene (4.7%), and muurola-4,10(14)-dien-1β-ol (4.9%) [ 49 ]. Other Piper species that present δ-elemene as one of the main constituents are P. aequale (19.0%) [ 50 ], P. amalago (6.82%) [ 51 ], P. aleyreanum (8.2%) [ 52 ], P. artanthe (11.69%) [ 53 ], P. dilatatum (7.6%) [ 54 ], and P. fimbriulatum (9.4%) [ 48 ]. The major compounds in the “Clonada” and “Uthirankota” cultivars were oxygenated sesquiterpenoids (60.90 ± 3.58% and 75.01 ± 7.89%, respectively).…”

Μελέτη της βιοποικιλότητας του Cistus στην Ελλάδα και επιλογή γονοτύπων για ενεργές χημικές ουσίες με βιοτεχνολογικές προσεγγίσεις

“…Τα εκχυλίσματα κουμπεμπόλης παρουσίασαν την καλύτερη δραστικότητα έναντι των προνυμφών κουνουπιών, με τιμές LC 50 από 60,1 έως 50,0 μg /ml (Gu et al, 2009). Μία άλλη μελέτη επικεντρώθηκε στα συστατικά και την κυτταροτοξική δράση του αιθέριου ελαίου του Piper artanthe, όπου στις κύριες ενώσεις συμπεριλαμβανόταν η επι-κουμπεμπόλη, με συγκέντρωση 8,85%, και η κουμπεμπόλη, με 6,30% (Avella and Rios-Motta, 2010). Η κουμπεμπόλη βρέθηκε στο αιθέριο έλαιο από τα εναέρια μέρη και τα άνθη της Chromolaena odorata, με την επικουμπεμπόλη να ανιχνεύεται σε συγκέντρωση 9,8% και τη κουμπεμπόλη σε 8.6 % (Joshi, 2013).…”

“…Η ένωση κουμπεμπόλη ανήκει και αυτή στα σεσκιτερπένια με τον γονότυπο Τ3 με 68,61 μg/g φύλλου να είναι ο πλέον παραγωγικός, ενώ σε επίπεδο πληθυσμών αυτός που παρουσίασε την υψηλότερη απόδοση ήταν της Τήνου (Σχήμα 3.6.2.7Α, 3.6.2.7Β, Αποτελέσματα). Η ένωση περιέχεται στο είδος Piper cubeba, στο αιθέριο έλαιο του Piper artanthe σε συγκέντρωση 6,30% (Avella and Rios-Motta, 2010) και ενώ έχει ανιχνευτεί στο είδος C. creticus (Kampranis and Makris 2012) δεν έχει ποσοτικοποιηθεί. Η κουμπεμπόλη αποτελεί παράγοντα δροσισμού-ανανέωσης σε τρόφιμα (Leffingwell, 2007), ενώ έχει και δραστικότητα έναντι των προνυμφών κουνουπιών (Gu et al 2009) και Το σεσκιτερπένιο βιριντιφλορόλη σε επίπεδο γονοτύπων τη μεγαλύτερη παραγωγή έδωσε ο S3 από τις Σίσσες με 83,14 μg/g φύλλου και σε επίπεδο πληθυσμών υπερτερούσαν τα Φλώρια (Σχήμα 3.6.2.9Α, 3.6.2.9Β, Αποτελέσματα).…”