Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia

Leyla Güven; Ufuk Özgen; Hasan Seçen; Sıla Özlem Şener; Merve Badem; Gonca Çelik; Nurettin Yaylı

doi:10.29228/jrp.6

Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia

Abstract

The roots and pseudofruits of Rosa pimpinellifolia (Rosaceae) are used in traditional medicine as hemorrhoids, various infections, abdominal pain complaints, heart disease, flu, cold, and anemia treatment in Turkey. In this study, the phytochemical composition of the R. pimpinellifolia was revealed by using chromatographic and spectroscopic techniques. Two condensed tannin precursor, (-)-catechin (1), the mixture of catechin and epicatechin (2) and three triterpenoid glycosides, kaji-ichigoside F1 (3), 2α,3β,19α trihydroxyurs-12-en-28-O-β-D-glucopyranoside (4), 2α,3β,19α,23β-tetrahydroxyurs-12-en-28-O-β-D-glucopyranoside (5) were isolated from the roots of R. pimpinellifolia. The isolation studies were performed by column chromatography. The chemical structures of the isolated compounds were elucidated with 1H and 13C NMR spectroscopy. Total phenolic compound contents were determined as 31.1937 mg/g dry extract in the pseudofruit; 9.8909 mg/g dry extract in the root via HPLC. The seeds of R. pimpinellifolia were extracted with diethyl ether in Soxhlet apparatus. The methyl esters of fatty acid were obtained from fixed oil and analyzed by GC/MS. The total ratio of unsaturated fatty acids in the seeds was 93.4%; containing 51.40% ratio of linoleic acid and 41.20% ratio of homo-γ-linolenic acid.

Keywords

References

[1] Davis PH. Nilsson Ö. Rosa L. In Flora of Turkey and the East Aegean Islands vol 4. Edinburgh University Press, UK, 1972, pp 106-128.
[2] Baytop T, Türkiye’de Bitkiler ile Tedavi. Istanbul Üniversitesi, Istanbul, Türkiye 1999.
[3] Özgen U, Kaya Y, Houghton P. Folk medicines in the villages of Ilıca District (Erzurum, Turkey). Turk J Biol. 2012; 36(1): 93-106. [CrossRef]
[4] Tetik F, Civelek S, Cakilcioglu U. Traditional uses of some medicinal plants in Malatya (Turkey). J Ethnopharmacol. 2013; 146 (1): 331-346. [CrossRef]
[5] Gürhan G, Ezer N. Halk arasında hemoroit tedavisinde kullanılan bitkiler-I. Hacettepe Univ Eczacı Fak Derg. 2004; 24 (1): 37-55.
[6] Altundag E, Ozturk M. Ethnomedicinal studies on the plant resources of East Anatolia, Turkey. Procedia Soc Behav Sci. 2011; 19: 756-777. [CrossRef]
[7] Coşkun M, Kurucu S, Kartal M. HPLC analysis of ascorbic acid in the fruits of some Turkish Rosa species. Sci Pharm. 1997; 65: 169-174.
[8] Vertuani S, Bosco E, Testoni M, Ascanelli S, Azzena G, Manfredini S. Antioxidant herbal supplements for hemorrhoids. Developing a new formula. Nutrafoods. 2004; 3: 19-26.

[9] Ullah M, Khan H, Zubair H, Shamim U, Hadi S. The antioxidant ascorbic acid mobilizes nuclear copper leading to a prooxidant breakage of cellular DNA: implications for chemotherapeutic action against cancer. Cancer Chemother Pharmacol. 2011; 67 (1): 103-110. [CrossRef]
[10] Roman I, Stanila A, Stanila S. Bioactive compounds and antioxidant activity of Rosa canina L. biotypes from spontaneous flora of Transylvania. Chem Cent J. 2013; 7(1): 73. [CrossRef]
[11] Shin I-C, Jeong K-J, Shim T-H, Oh H-S, Park S-K, Cheung E-H, Kim S-N, Kim G-G, Choi D-S, Kwon Y-S. Catechin content and antioxidative effect from Rosa davurica Pall. Korean J Physiol Pharmacol. 2002; 33 (3): 177-181.
[12] Ahmad N, Anwar F. Rose hip (Rosa canina L.) oils. In: Essential oils in food preservation, flavor and safety. Elsevier. 2016; 667-675.
[13] Bruneton J. Pharmacognosy, phytochemistry, medicinal plants. vol Ed. 2. Technique et Documentation Lavoisier, Paris 1993.
[14] Cunnane S, Anderson M. Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and [1-14C] linoleate oxidation. J Lipid Res. 1997; 38 (4): 805-812.
[15] Schmitz G, Ecker J. The opposing effects of n− 3 and n− 6 fatty acids. Prog Lipid Res. 2008; 47 (2): 147-155. [CrossRef]
[16] Horrobin D. Nutritional and medical importance of gamma-linolenic acid. Prog Lipid Res. 1992; 31 (2): 163-194. [CrossRef]
[17] Feller SE, Gawrisch K. Properties of docosahexaenoic-acid-containing lipids and their influence on the function of rhodopsin. Curr Opin Struct Biol. 2005; 15 (4): 416-422. [CrossRef]
[18] Kumar N, Bhandari P, Singh B, Gupta AP, Kaul VK. Reversed phase-HPLC for rapid determination of polyphenols in flowers of Rosa species. J Sep Sci. 2008; 31 (2): 262-267. [CrossRef]
[19] Mikanagi Y, Yokoi M, Ueda Y, Saito N. Flower flavonol and anthocyanin distribution in subgenus Rosa. Biochem Syst Ecol. 1995; 23 (2): 183-200. [CrossRef]
[20] Gao X, Yang L, Shu L, Shen Y, Zhang Y, Hu Q. Aurone constituents from the flowers of Rosa rugosa and their biological activities. Heterocycles. 2012; 85 (8): 1925-1931. [CrossRef]
[21] Çoruh N, Özdoğan N. Identification and quantification of phenolic components of Rosa heckeliana Tratt roots. J Liq Chromatogr Relat. 2015; 38 (5): 569-578. [CrossRef]
[22] Gao XM, Shu LD, Yang LY, Shen YQ, Zhang YJ, Hu QF. Phenylethanoids from the flowers of Rosa rugosa and their biological activities. Bull Korean Chem Soc. 2013; 34 (1): 246-248. [CrossRef]
[23] Liu D, Zhu S, Ma R, Zhang J, Li H, Chen H. Triterpenoids from the roots of Rose odorata var. gigantean. Chin J Nat Med. 2010; 8 (1): 12-15. [CrossRef]
[24] Stoyanova-Ivanova B, Iochkova I, Mladenova K, Daskalov R. Content and composition of neutral components in wax from Rosa canina flowers. Dokl Bolg Akad Nauk. 1979; 32 (11): 1503-1506.
[25] Hashidoko Y. The phytochemistry of Rosa rugosa. Phytochemistry. 1996; 43 (3): 535-549. [CrossRef]
[26] Novruzov EN. Pigments of species in the genus Rosa and their chemotaxonomic value. Acta Horticulturae 690. (Proceedings of the 1st International Rose Hip Conference, 2004). 2005; 225-230.
[27] Ghazghazi H, Miguel MG, Hasnaoui B, Sebei H, Ksontini M, Figueiredo AC, Pedro LG, Barroso JG. Phenols, essential oils and carotenoids of Rosa canina from Tunisia and their antioxidant activities. Afr J Biotechnol. 2010; 9 (18): 2709-2716.
[28] Al-Rehaily AJ, Al-Howiriny TA, Bizzo HR Essential oil of Rosa abyssinica R. Br. from Saudi Arabia. J Essent Oil Res. 2003; 15 (5): 344-345. [CrossRef]
[29] Yoshida T, Jin Z, Okuda T. Tannins of rosaceous medicinal plants. Part 10. Hydrolyzable tannin oligomers from Rosa davurica. Phytochemistry. 1991; 30(8): 2747-2752. [CrossRef]
[30] Park JC, Hwang YH, Choi DR, Jung DY, Park JG, Hur JM, Kim SJ, Kim SN, Kim MS. A triterpenoid glucoside and phenolic compounds from Rosa davurica. Nat Prod Sci. 2003; 9(1): 31-33.
[31] Yang SC, Fang JM, Cheng YS. Chemical constituents from the root and aerial parts of Rosa taiwanensis. J Chın Chem Soc. 1995; 42(3): 573-577. [CrossRef]
[32] Li Y, Hu L, Lou F. Studies on the constituents of Rosa multiflora Thunb. Zhongguo Yaoke Daxue Xuebao. 2002; 33(3): 184-187
[33] Park KH, Kim SK, Choi SE, Kwon JH, Oh MH, Lee MW. Three new stereoisomers of condensed tannins from the roots of Rosa multiflora. Chem Pharm Bull. 2010; 58(9): 1227-1231. [CrossRef]
[34] Yeo H, Chin YW, Park SY, Kim J. Lignans of Rosa multiflora roots. Arch Pharm Res. 2004; 27(3): 287-290. [CrossRef]
[35] Li S, Zhai X, Wang T, Ma W, Hu J, Wang S, Li N, Wang K. Flavonoids and triterpenoids from the roots of Rosa laevigata. J Mex Chem Soc. 2014; 58(4): 374-377.
[36] He RR, Yao XS, Yao N, Wang M, Dai Y, Gao H, Yu Y, Kurihara H. Protective effects of radix Rosa laevigata against Propionibacterium acnes and lipopolysaccharide-induced liver injury. Biosci Biotechnol Biochem. 2009; 73(5): 1129-1136. [CrossRef]
[37] Liu DL, Zhu S, Ma R, Zhang JZ, Li HY, Chen H. Triterpenoids from the roots of Rose odorata var. gigantean. Chin J Nat Med. 2010; 8(1): 12-15. [CrossRef]
[38] An HJ, Kim IT, Park HJ, Kim HM, Choi JH, Lee KT. Tormentic acid, a triterpenoid saponin, isolated from Rosa rugosa, inhibited LPS-induced iNOS, COX-2, and TNF-α expression through inactivation of the nuclear factor-κb pathway in RAW 264.7 macrophages. Int. Immunopharmacol. 2011;11(4): 504-510. [CrossRef]
[39] Coruh N, Ozdogan N. Wild-growing Rosa heckeliana Tratt.: phenolic constituents with cytotoxic and antioxidative properties. Turk J Biol. 2017; 41: 195-212. [CrossRef]
[40] Park KH, Jeong MS, Park KJ, Choi YW, Seo SJ, Lee MW. Topical application of Rosa multiflora root extract improves atopic dermatitis-like skin lesions induced by mite antigen in NC/Nga mice. Biol Pharm Bull. 2014; 37(1): 178-183. [CrossRef]
[41] Kim IT, Ryu S, Shin JS, Choi JH, Park HJ, Lee KT. Euscaphic acid isolated from roots of Rosa rugosa inhibits LPS-induced inflammatory responses via TLR4-mediated NF-κB inactivation in RAW 264.7 macrophages. J Cell Biochem. 2012; 113(6): 1936-1946. [CrossRef]
[42] Porter EA., Van den Bos AA, Kite GC, Veitch NC, Simmonds MS. Flavonol glycosides acylated with 3-hydroxy-3-methylglutaric acid as systematic characters in Rosa. Phytochemistry. 2012; 81: 90-96. [CrossRef]
[43] Mavi A, Terzi Z, Özgen U, Yildirim A, Coşkun M. Antioxidant properties of some medicinal plants: Prangos ferulacea(Apiaceae), Sedum sempervivoides (Crassulaceae), Malva neglecta (Malvaceae), Cruciata taurica (Rubiaceae), Rosa pimpinellifolia (Rosaceae), Galium verum subsp. verum (Rubiaceae), Urtica dioica (Urticaceae). Biol Pharm Bull. 2004; 27(5): 702-705. [CrossRef]
[44] Seto R, Nakamura H, Nanjo F, Hara Y. Preparation of epimers of tea catechins by heat treatment. Biosci Biotechnol Biochem. 1997; 61 (9): 1434-1439. [CrossRef]
[45] Davis AL, Cai Y, Davies AP, Lewis J. 1H and 13C NMR assignments of some green tea polyphenols. Magn Reson Chem. 1996; 34 (11): 887-890. [CrossRef]
[46] Guang-yi L. The isolation and structure of-kaji-ichigoside f1 and rosamultin. Acta Bot Sin. 1988; 4: 409-413.
[47] Wang Q, Ju P, Wang Y-F, Luo S-D. Triterpenoids from Saurauia napaulensis (Saurauiaceae). Acta Bot Yunnan. 2008; 30 (1): 121-124.
[48] Liu DL, Zhu S, Ma R, Zhang JZ, Li HY, Chen H. Triterpenoids from the roots of Rose odorata var. gigantean. Chin J Nat Med. 2010; 8 (1): 12-15. [CrossRef]
[49] Seto T, Tanaka T, Tanaka O, Naruhashi N. β-Glucosyl esters of 19α-hydroxyursolic acid derivatives in leaves of Rubusspecies. Phytochemistry. 1984; 23 (12): 2829-2834.[CrossRef]
[50] De Leo M, De Tommasi N, Sanogo R, D’Angelo V, Germanò MP, Bisignano G, Braca A. Triterpenoid saponins from Pteleopsis suberosa stem bark. Phytochemistry. 2006. 67(24): p. 2623-2629. [CrossRef]
[51] Ponou BK, Teponno RB, Ricciutelli M, Quassinti L, Bramucci M, Lupidi G, Barboni L, Tapondjou LA. Dimeric antioxidant and cytotoxic triterpenoid saponins from Terminalia ivorensis A. Chev. Phytochemistry. 2010. 71(17-18): p. 2108-2115. [CrossRef]
[52] Aliyazicioglu R, Demir S, Badem M, Sener SO, Korkmaz N, Demi EA, Ozgen U, Karaoglu SA, Aliyazicioglu Y. Antioxidant, Antigenotoxic, Antimicrobial Activities and Phytochemical Analysis of Dianthus carmelitarum. Rec Nat Prod. 2017; 11 (3).
[53] Shameh S, Alirezalu A, Hosseini B, Maleki R. Fruits phytochemical composition and color parameters of twenty‐one accessions of five Rosa species grown in North West Iran. J Sci Food Agric. 2019; 99(13): 5740-5751. [CrossRef]
[54] Okan O, Serencam H, Baltas N, Can Z. Some edible forest fruits their in vitro antioxidant activities, phenolic compounds and some enzyme inhibition effects. Fresenius Environ. Bull. 2019; 28: 6090-6098.
[55] Cakir A. Essential oil and fatty acid composition of the fruits of Hippophae rhamnoides L. (Sea Buckthorn) and Myrtus communis L. from Turkey. Biochem Syst Ecol. 2004; 32 (9): 809-816. [CrossRef] [56] Murathan ZT, Zarifikhosroshahi M, Kafkas NE. Determination of fatty acids and volatile compounds in fruits of rosehip (Rosa L.) species by HS-SPME/GC-MS and Im-SPME/GC-MS techniques. Turk J Agric For. 2016; 40 (2): 269-279. [CrossRef]
[57] Ercisli S, Orhan E, Esitken A. Fatty acid composition of Rosa species seeds in Turkey. Chem Nat Compd. 2007; 43 (5): 605-606.
[58] Renda G, Celik G, Korkmaz B, Karaoglu SA, Yayli N Antimicrobial Activity and Analyses of Six Geranium L. Species with Headspace SPME and Hydrodistillation. J Essent Oil Bear Pl. 2016; 19 (8): 2003-2016. [CrossRef]
[59] Adams RP. Identification of volatile oil components by gas chromatography/mass spectroscopy. Allured Publishing Corporation, Carol Stream, IL, USA 2004.
[60] Yaylı N, Tosun G, Yayh B, Gündoğan Z, Coşkunçelebi K, Karaoğlu Ş. Altitude Variation in the Composition of Essential Oils, Fatty Acid Methyl Esters, and Antimicrobial Activities of Two Subspecies of Primula vulgaris Grown in Turkey. Nat Prod Commun. 2016; 11 (10): 1505-1510.

Details

Primary Language

English

Subjects

Pharmacognosy, Pharmaceutical Botany

Journal Section

Research Article

Authors

Leyla Güven ^*
Türkiye

Ufuk Özgen
Türkiye

Hasan Seçen
Türkiye

Sıla Özlem Şener This is me
Türkiye

Merve Badem
Türkiye

Gonca Çelik
Türkiye

Nurettin Yaylı
Türkiye

Publication Date

June 27, 2025

Submission Date

September 17, 2020

Acceptance Date

February 15, 2021

Published in Issue

Year 2021 Volume: 25 Number: 2

DOI

https://doi.org/10.29228/jrp.6

IZ

https://izlik.org/JA89KB46SE

Cite

RIS / Bibtex

APA

Güven, L., Özgen, U., Seçen, H., Şener, S. Ö., Badem, M., Çelik, G., & Yaylı, N. (2025). Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia. Journal of Research in Pharmacy, 25(2), 153-163. https://doi.org/10.29228/jrp.6

AMA

1.Güven L, Özgen U, Seçen H, et al. Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia. J. Res. Pharm. 2025;25(2):153-163. doi:10.29228/jrp.6

Chicago

Güven, Leyla, Ufuk Özgen, Hasan Seçen, et al. 2025. “Phytochemical Studies on the Seeds, Pseudofruits, and Roots of Rosa Pimpinellifolia”. Journal of Research in Pharmacy 25 (2): 153-63. https://doi.org/10.29228/jrp.6.

EndNote

Güven L, Özgen U, Seçen H, Şener SÖ, Badem M, Çelik G, Yaylı N (June 1, 2025) Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia. Journal of Research in Pharmacy 25 2 153–163.

IEEE

[1]L. Güven et al., “Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia”, J. Res. Pharm., vol. 25, no. 2, pp. 153–163, June 2025, doi: 10.29228/jrp.6.

ISNAD

Güven, Leyla - Özgen, Ufuk - Seçen, Hasan - Şener, Sıla Özlem - Badem, Merve - Çelik, Gonca - Yaylı, Nurettin. “Phytochemical Studies on the Seeds, Pseudofruits, and Roots of Rosa Pimpinellifolia”. Journal of Research in Pharmacy 25/2 (June 1, 2025): 153-163. https://doi.org/10.29228/jrp.6.

JAMA

1.Güven L, Özgen U, Seçen H, Şener SÖ, Badem M, Çelik G, Yaylı N. Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia. J. Res. Pharm. 2025;25:153–163.

MLA

Güven, Leyla, et al. “Phytochemical Studies on the Seeds, Pseudofruits, and Roots of Rosa Pimpinellifolia”. Journal of Research in Pharmacy, vol. 25, no. 2, June 2025, pp. 153-6, doi:10.29228/jrp.6.

Vancouver

1.Leyla Güven, Ufuk Özgen, Hasan Seçen, Sıla Özlem Şener, Merve Badem, Gonca Çelik, Nurettin Yaylı. Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia. J. Res. Pharm. 2025 Jun. 1;25(2):153-6. doi:10.29228/jrp.6

Cited By

Cephalaria tchihatchewii Boiss. Ekstrelerinin Antioksidan Aktivitesi, Metabolik Enzimler Üzerine Etkisi ve UPLC-MS/MS Analizi ile Kimyasal Karakterizasyonun Belirlenmesi

Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi

https://doi.org/10.21597/jist.1337439

Evaluation of LC-MS/MS Analysis and In Vitro Biological Activities of Rosa pimpinellifolia Root, Pseudo-fruit, and Seed extracts

International Journal of Life Sciences and Biotechnology

https://doi.org/10.38001/ijlsb.1108547

Fruit extracts of Rosa canina L. and Rosa pimpinellifolia L.: Phytochemical profiles, in vitro antioxidant, anti-inflammatory, xanthine oxidase inhibitory effects, and in silico molecular dynamics studies

Kahramanmaraş Sütçü İmam Üniversitesi Tarım ve Doğa Dergisi

https://doi.org/10.18016/ksutarimdoga.vi.1639294