nach oben

Erschienen in:

28.11.2022 | Original Paper

Essential oil composition of Curcuma species and drugs from Asia analyzed by headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry

verfasst von: Qundong Liu, Katsuko Komatsu, Kazufumi Toume, Shu Zhu, Ken Tanaka, Shigeki Hayashi, Naoko Anjiki, Nobuo Kawahara, Akihito Takano, Katsunori Miyake, Norio Nakamura, Suchada Sukrong, Mangestuti Agil, Indira Balachandra

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2023

Einloggen, um Zugang zu erhalten

Abstract

Essential oils (EOs) comprised of various bioactive compounds have been widely detected in the Curcuma species. Due to the widespread distribution and misidentification of Curcuma species and differences in processing methods, inconsistent reports on major compounds in rhizomes of the same species from different geographical regions are not uncommon. This inconsistency leads to confusion and inaccuracy in compound detection of each species and also hinders comparative study based on EO compositions. The present study aimed to characterize EO compositions of 12 Curcuma species, as well as to detect the compositional variation among different species, and between the plant specimens and their related genetically validated crude drug samples using headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry. The plant specimens of the same species showed similar EO patterns, regardless of introducing from different geographical sources. Based on the similarity of EO compositions, all the specimens and samples were separated into eight main groups: C. longa; C. phaeocaulis, C. aeruginosa and C. zedoaria; C. zanthorrhiza; C. aromatica and C. wenyujin; C. kwangsiensis; C. amada and C. mangga; C. petiolata; C. comosa. From EOs of all the specimens and samples, 54 major compounds were identified, and the eight groups were chemically characterized. Most of the major compounds detected in plant specimens were also observed in crude drug samples, although a few compounds converted or degraded due to processing procedures or over time. Orthogonal partial least squares-discriminant analysis allowed the marker compounds to discriminate each group or each species to be identified.

Ravindran PN, Babu KN, Sivaraman K (2007) Turmeric: The genus Curcuma. CRC Press, pp 1–27, 409–436, 451–467

Xu XY, Meng X, Li S, Gan RY, Li Y, Li HB (2018) Bioactivity, health benefits, and related molecular mechanisms of curcumin: current progress, challenges, and perspectives. Nutrients 10:1553. https://doi.org/10.3390/nu10101553CrossRef

Dosoky NS, Setzer WN (2018) Chemical composition and biological activities of essential oils of Curcuma species. Nutrients 10:1196. https://doi.org/10.3390/nu10091196CrossRef

Lechtenberg M, Quandt B, Nahrstedt A (2004) Quantitative determination of curcuminoids in Curcuma rhizomes and rapid differentiation of Curcuma domestica Val. and Curcuma xanthorrhiza Roxb. by capillary electrophoresis. Phytochem Anal 15:152–158. https://doi.org/10.1002/pca.759CrossRef

Li R, Xiang C, Ye M, Li HF, Zhang X, Guo DA (2011) Qualitative and quantitative analysis of curcuminoids in herbal medicines derived from Curcuma species. Food Chem 126:1890–1895. https://doi.org/10.1016/j.foodchem.2010.12.014CrossRef

Dosoky NS, Satyal P, Setzer W (2019) Variations in the volatile compositions of Curcuma species. Foods 8:53. https://doi.org/10.3390/foods8020053CrossRef

Negi PS, Jayaprakasha GK, Jagan MRL, Sakariah KK (1999) Antibacterial activity of turmeric oil: a byproduct from curcumin manufacture. J Agric Food Chem 47:4297–4300. https://doi.org/10.1021/jf990308dCrossRef

Behura C, Ray P, Rath CC, Mishra RK, Ramachandraiah OS, Charyulu JK (2000) Antifungal activity of essential oils of Curcuma longa against five rice pathogens in vitro. J Essent Oil-Bear Plants 3:79–84

Honda S, Aoki F, Tanaka H, Kishida H, Nishiyama T, Okada S, Matsumoto I, Abe K, Mae T (2006) Effects of ingested turmeric oleoresin on glucose and lipid metabolisms in obese diabetic mice: a DNA microarray study. J Agric Food Chem 54:9055–9062. https://doi.org/10.1021/jf061788tCrossRef

10.

Tsai SY, Huang SJ, Chyau CC, Tsai CH, Weng CC, Mau JL (2011) Composition and antioxidant properties of essential oils from Curcuma rhizome. Asian J Arts Sci 2:57–66

11.

Tohda C, Nakayama N, Hatanaka F, Komatsu K (2006) Comparison of anti-inflammatory activities of six Curcuma rhizomes: a possible curcuminoid-independent pathway mediated by Curcuma phaeocaulis extract. Evid Based Complement Alternat Med 3:255–260. https://doi.org/10.1093/ecam/nel008CrossRef

12.

Tanaka K, Kuba Y, Ina A, Watanabe H, Komatsu K (2008) Prediction of cyclooxygenase inhibitory activity of Curcuma rhizome from chromatograms by multivariate analysis. Chem Pharm Bull 56:936–940. https://doi.org/10.1248/cpb.56.936CrossRef

13.

Naveen Kumar K, Venkataramana M, Allen JA, Chandranayaka S, Murali HS, Batra HV (2016) Role of Curcuma longa L. essential oil in controlling the growth and zearalenone production of Fusarium graminearum. LWT-Food Sci Technol 69:522–528. https://doi.org/10.1016/j.lwt.2016.02.005CrossRef

14.

Jantan I, Saputri FC, Qaisar MN, Buang F (2012) Correlation between chemical composition of Curcuma domestica and Curcuma xanthorrhiza and their antioxidant effect on human low-density lipoprotein oxidation. Evid Based Complement Alternat Med 2012:e438356. https://doi.org/10.1155/2012/438356CrossRef

15.

Theanphong O, Mingvanish W, Kirdmanee C (2015) Chemical constituents and biological activities of essential oil from Curcuma aeruginosa Roxb. rhizome. BHST 13:06–16

16.

Braga MEM, Leal PF, Carvalho JE, Meireles MAA (2003) Comparison of yield, composition, and antioxidant activity of turmeric (Curcuma longa L.) extracts obtained using various techniques. J Agric Food Chem 51:6604–6611. https://doi.org/10.1021/jf0345550CrossRef

17.

Lai EYC, Chyau CC, Mau JL, Chen CC, Lai YJ, Shih CF, Lin LL (2004) Antimicrobial activity and cytotoxicity of the essential oil of Curcuma zedoaria. Am J Chin Med 32:281–290. https://doi.org/10.1142/S0192415X0400193XCrossRef

18.

Angel GR, Menon N, Vimala B, Nambisan B (2014) Essential oil composition of eight starchy Curcuma species. Ind Crops Prod 60:233–238. https://doi.org/10.1016/j.indcrop.2014.06.028CrossRef

19.

Liu Q, Zhu S, Hayashi S, Takano A, Miyake K, Sukrong S, Agil M, Balachandra I, Nakamura N, Kawahara N, Komatsu K (2021) Discrimination of Curcuma species from Asia using intron length polymorphism markers in genes encoding diketide-CoA synthase and curcumin synthase. J Nat Med 76:69–86. https://doi.org/10.1007/s11418-021-01558-2CrossRef

20.

Wang C, Zhang W, Li H, Mao J, Guo C, Ding R, Wang Y, Fang L, Chen Z, Yang G (2019) Analysis of volatile compounds in pears by HS-SPME-GC×GC-TOFMS. Molecules 24:E1795. https://doi.org/10.3390/molecules24091795CrossRef

21.

Wang X, Rogers KM, Li Y, Yang S, Chen L, Zhou J (2019) Untargeted and targeted discrimination of honey collected by Apis cerana and Apis mellifera based on volatiles using HS-GC-IMS and HS-SPME-GC-MS. J Agric Food Chem 67:12144–12152. https://doi.org/10.1021/acs.jafc.9b04438CrossRef

22.

Zhang C, Qi M, Shao Q, Zhou S, Fu R (2007) Analysis of the volatile compounds in Ligusticum chuanxiong Hort. using HS-SPME-GC-MS. J Pharm Biomed Anal 44:464–470. https://doi.org/10.1016/j.jpba.2007.01.024CrossRef

23.

Uehara S, Yasuda I, Takeya K, Itokawa H (1992) Terpenoids and curcuminoids of the rhizome of Curcuma xanthorrhiza Roxb. Yakugaku Zasshi 112:817–823CrossRef

24.

Yang FQ, Li SP, Chen Y, Lao SC, Wang YT, Dong T, Tsim K (2005) Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. J Pharm Biomed Anal 39:552–558. https://doi.org/10.1016/j.jpba.2005.05.001CrossRef

25.

Sun W, Wang S, Zhao W, Wu C, Guo S, Gao H, Tao H, Lu J, Wang Y, Chen X (2017) Chemical constituents and biological research on plants in the genus Curcuma. Crit Rev Food Sci Nutr 57:1451–1523. https://doi.org/10.1080/10408398.2016.1176554CrossRef

26.

Komatsu K, Sasaki Y, Tanaka K, Kuba Y, Fushimi H, Cai S-Q (2008) Morphological, genetic, and chemical polymorphism of Curcuma kwangsiensis. J Nat Med 62:413–422. https://doi.org/10.1007/s11418-008-0272-xCrossRef

27.

Pk A, Sc D (2009) Chemical composition of Curcuma longa leaves and rhizome oil from the plains of Northern India. J Young Pharm 1:312. https://doi.org/10.4103/0975-1483.59319CrossRef

28.

Naz S, Ilyas S, Parveen Z, Javed S (2010) Chemical analysis of essential oils from turmeric (Curcuma longa) rhizome through GC-MS. Asian J Chem 22:3153–3158

29.

Asghari G, Mostajeran A, Shebli M (2010) Curcuminoid and essential oil components of turmeric at different stages of growth cultivated in Iran. Res Pharma Sci 4:55–61

30.

Oyemitan IA, Elusiyan CA, Onifade AO, Akanmu MA, Oyedeji AO, McDonald AG (2017) Neuropharmacological profile and chemical analysis of fresh rhizome essential oil of Curcuma longa (turmeric) cultivated in Southwest Nigeria. Toxicol Rep 4:391–398. https://doi.org/10.1016/j.toxrep.2017.07.001CrossRef

31.

Gardini F, Belletti N, Ndagijimana M, Guerzoni ME, Tchoumbougnang F, Zollo PHA, Micci C, Lanciotti R, Kamdem SLS (2009) Composition of four essential oils obtained from plants from Cameroon, and their bactericidal and bacteriostatic activity against Listeria monocytogenes, Salmonella enteritidis and Staphylococcus aureus. AJMR 3:264–271. https://doi.org/10.5897/AJMR.9000198CrossRef

32.

Ferreira FD, Kemmelmeier C, Arrotéia CC, da Costa CL, Mallmann CA, Janeiro V, Ferreira FMD, Mossini SAG, Silva EL, Machinski M (2013) Inhibitory effect of the essential oil of Curcuma longa L. and curcumin on aflatoxin production by Aspergillus flavus Link. Food Chem 136:789–793. https://doi.org/10.1016/j.foodchem.2012.08.003CrossRef

33.

Sharma RK, Misra BP, Sarma TC, Bordoloi AK, Pathak MG, Leclercq PA (1997) Essential oils of Curcuma longa L. from Bhutan. J Essent Oil Res 9:589–592. https://doi.org/10.1080/10412905.1997.9700783CrossRef

34.

Chane-Ming J, Vera R, Chalchat J-C, Cabassu P (2002) Chemical composition of essential oils from rhizomes, leaves and flowers of Curcuma longa L. from Reunion Island. J Essent Oil Res 14:249–251. https://doi.org/10.1080/10412905.2002.9699843CrossRef

35.

Zhang L, Yang Z, Chen F, Su P, Chen D, Pan W, Fang Y, Dong C, Zheng X, Du Z (2017) Composition and bioactivity assessment of essential oils of Curcuma longa L. collected in China. Ind Crops Prod 109:60–73. https://doi.org/10.1016/j.indcrop.2017.08.009CrossRef

36.

Singh P, Singh S, Kapoor IPS, Singh G, Isidorov V, Szczepaniak L (2013) Chemical composition and antioxidant activities of essential oil and oleoresins from Curcuma zedoaria rhizomes, part-74. Food Biosci 3:42–48. https://doi.org/10.1016/j.fbio.2013.06.002CrossRef

37.

Kojima H, Yanai T, Toyota A (1998) Essential oil constituents from Japanese and Indian Curcuma aromatica rhizomes. Planta Med 64:380–381. https://doi.org/10.1055/s-2006-957458CrossRef

38.

Singh G, Singh OP, Maurya S (2002) Chemical and biocidal investigations on essential oils of some Indian Curcuma species. Prog Cryst Growth Charact Mater 45:75–81. https://doi.org/10.1016/S0960-8974(02)00030-XCrossRef

39.

Wahab IRA, Blagojević PD, Radulović NS, Boylan F (2011) Volatiles of Curcuma mangga Val. & Zijp (Zingiberaceae) from Malaysia. Chem Biodivers 8:2005–2014. https://doi.org/10.1002/cbdv.201100135CrossRef

40.

Singh G, Kapoor IPS, Singh P, de Heluani CS, de Lampasona MP, Catalan CAN (2010) Comparative study of chemical composition and antioxidant activity of fresh and dry rhizomes of turmeric (Curcuma longa Linn.). Food Chem Toxicol 48:1026–1031. https://doi.org/10.1016/j.fct.2010.01.015CrossRef

41.

Sakui N, Kuroyanagi M, Ishitobi Y, Sato Y, Ueno A (1992) Biotransformation of sesquiterpenes by cultures cells of Curcuma zedoaria. Phytochemistry 31:143–147CrossRef

42.

Asakawa Y, Noma Y (2010) Biotransformation of sesquiterpenoids. In: Mander L, Liu HW (eds) Comprehensive natural products II: chemistry and biology. Elsevier Ltd., pp 824–825

43.

Albino RC, Oliveira PC, Prosdocimi F, da Silva OF, Bizzo HR, Gama PE, Sakuragui CM, Furtado C, de Oliveira DR (2017) Oxidation of monoterpenes in Protium heptaphyllus oleoresins. Phytochemistry 136:141–146. https://doi.org/10.1016/j.phytochem.2017.01.013CrossRef

44.

Yang FQ, Li SP, Zhao J, Lao SC, Wang YT (2007) Optimization of GC-MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes. J Pharm Biomed Anal 43:73–82. https://doi.org/10.1016/j.jpba.2006.06.014CrossRef

45.

Padalia RC, Verma RS, Sundaresan V, Chauhan A, Chanotiya CS, Yadav A (2013) Volatile terpenoid compositions of leaf and rhizome of Curcuma amada Roxb. from Northern India. J Essent Oil Res 25:17–22. https://doi.org/10.1080/10412905.2012.747271CrossRef

46.

Phaet-thanesuara P (ed) (1969) Pramuan Sapphakhun Ya Thai (Medicinal uses of Thai drugs), vol 3. Samakhon Rongrian Phaet Phaen Boran, Bangkok, pp 155–156

47.

Qu Y, Xu F, Nakamura S, Matsuda H, Pongpiriiiyadacha Y, Wu L, Yoshikawa M (2009) Sesquiterpenes from Curcuma comosa. J Nat Med 63:102–104. https://doi.org/10.1007/s11418-008-0282-8CrossRef

48.

Palanuvej C, Ruangrungsi N (2007) Chemical constituents and antimicrobial activity of volatile oil from Curcuma comosa Rhizome. J Health Res 21:35–42

49.

Soontornchainaksaeng P, Jenjittikul T (2010) Chromosome number variation of phytoestrogen-producing Curcuma (Zingiberaceae) from Thailand. J Nat Med 64:370–377. https://doi.org/10.1007/s11418-010-0414-9CrossRef

50.

Keeratinijakal V, Kongkiatpaiboon S (2017) Distribution of phytoestrogenic diarylheptanoids and sesquiterpenoids components in Curcuma comosa rhizomes and its related species. Rev Bras Farmacogn 27:290–296. https://doi.org/10.1016/j.bjp.2016.12.003CrossRef

Titel: Essential oil composition of Curcuma species and drugs from Asia analyzed by headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry
verfasst von: Qundong Liu
Katsuko Komatsu
Kazufumi Toume
Shu Zhu
Ken Tanaka
Shigeki Hayashi
Naoko Anjiki
Nobuo Kawahara
Akihito Takano
Katsunori Miyake
Norio Nakamura
Suchada Sukrong
Mangestuti Agil
Indira Balachandra
Publikationsdatum: 28.11.2022
Verlag: Springer Nature Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 1/2023
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-022-01658-7

Preparation and pharmaceutical properties of Hangeshashinto oral ointment and its safety and efficacy in Syrian hamsters with 5-fluorouracil-induced oral mucositis

Open Access
Original Paper

Anti-influenza A virus activity of flavonoids in vitro: a structure–activity relationship

Note

Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity

Original Paper

Hepatoprotective functions of jujuboside B

Original Paper

Andrographolide ameliorates hepatic steatosis by suppressing FATP2-mediated fatty acid uptake in mice with nonalcoholic fatty liver disease

Open Access
Original Paper

Seasonal variation in the total saponin content of platycodon roots cultivated in Japan

Original Paper

Springer Medizin

Essential oil composition of Curcuma species and drugs from Asia analyzed by headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry

Abstract

Weitere Artikel der Ausgabe 1/2023

Preparation and pharmaceutical properties of Hangeshashinto oral ointment and its safety and efficacy in Syrian hamsters with 5-fluorouracil-induced oral mucositis

Anti-influenza A virus activity of flavonoids in vitro: a structure–activity relationship

Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity

Hepatoprotective functions of jujuboside B

Andrographolide ameliorates hepatic steatosis by suppressing FATP2-mediated fatty acid uptake in mice with nonalcoholic fatty liver disease

Seasonal variation in the total saponin content of platycodon roots cultivated in Japan

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Preparation and pharmaceutical properties of Hangeshashinto oral ointment and its safety and efficacy in Syrian hamsters with 5-fluorouracil-induced oral mucositis

Anti-influenza A virus activity of flavonoids in vitro: a structure–activity relationship

Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity

Hepatoprotective functions of jujuboside B

Andrographolide ameliorates hepatic steatosis by suppressing FATP2-mediated fatty acid uptake in mice with nonalcoholic fatty liver disease

Seasonal variation in the total saponin content of platycodon roots cultivated in Japan