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Compositions of the Volatile Oils of Citrus Macroptera and C. Maxima

Natural Product Communications

October 2012
7(10):1371-2

DOI:10.1177/1934578X1200701032

Source
PubMed

Authors:

Virendra S. Rana

Indian Agricultural Research Institute, New Delhi, India

María Amparo Blázquez

University of Valencia

The essential oils obtained by hydrodistillation from the fresh peels of Citrus macroptera Montr. and C. maxima (Burm.) Merr. were analyzed by GC and GC/MS. The yields of oil ranged from 0.53% in C. macroptera to 0.13% in C. maxima cultivar (white). Forty-seven compounds were identified in the oils with limonene (55.3-80.0%), dodecyl acrylate (2.2-8.0%), geranial (0.4-3.5%), trans-linalool oxide (1.0-2.8%), alpha-terpineol (0.7-2.3%), linalool (0.7-1.5%) and cis-linalool oxide (0.5-1.4%) identified as major compounds. The oil ofC. macroptera contained limonene (55.3%), beta-caryophyllene (4.7%) and geranial (3.5%) as main compounds. Similarly, oils from two C. maxima (pink and white) cultivars were rich in limonene (72.0-80.0%), dodecyl acrylate (8.0-7.2%) and nootkatone (1.6-2.5%). C. maxima (pink and white) cultivars were found to contain higher amount of limonene (72.0 and 80.0%) as compared with C. macroptera (55.3%). The chemical compositions of the oils were found to be similar, but nootkatone (1.6-2.5%) was identified only in C. maxima cultivars.

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Compositions of the Volatile Oils of Citrus macroptera and C. maxima

Virendra S. Ranaa* and Maria A. Blazquezb

aNatural Product Chemistry Lab, Medicinal Plants and Horticultural Resources Division,

Institute of Bioresources of Sustainable Development, Imphal, Manipur, India

bDepartment of Pharmacology, Faculty of Pharmacy, University of Valencia, Valencia, Spain

ranavs2000@yahoo.com

Received: February 26th, 2012; Accepted: August 7th, 2012

The essential oils obtained by hydrodistillation from the fresh peels of Citrus macroptera Montr. and C. maxima (Burm.) Merr. were analyzed by GC and

GC/MS. The yields of oil ranged from 0.53% in C. macroptera to 0.13% in C. maxima cultivar (white). Forty-seven compounds were identified in the oils with

limonene (55.3-80.0%), dodecyl acrylate (2.2-8.0%), geranial (0.4-3.5%), trans-linalool oxide (1.0-2.8%), -terpineol (0.7-2.3%), linalool (0.7-1.5%) and cis-

linalool oxide (0.5-1.4%) identified as major compounds. The oil of C. macroptera contained limonene (55.3%), β-caryophyllene (4.7%) and geranial (3.5%)

as main compounds. Similarly, oils from two C. maxima (pink and white) cultivars were rich in limonene (72.0-80.0%), dodecyl acrylate (8.0-7.2%) and

nootkatone (1.6-2.5%). C. maxima (pink and white) cultivars were found to contain higher amount of limonene (72.0 and 80.0%) as compared with C.

macroptera (55.3%). The chemical compositions of the oils were found to be similar, but nootkatone (1.6-2.5%) was identified only in C. maxima cultivars.

Keywords: Rutaceae, Citrus macroptera, C. maxima, Essential oil, Limonene, Nootkatone.

Citrus L. (Family: Rutaceae), a genus of evergreen aromatic shrubs

or small trees, are cultivated throughout tropical and sub-tropical

regions of the world for their fruits [1,2]. Citrus fruit is one of the

major produce in Indian agriculture and mainly used for juice and

its products [3a]. Citrus fruit processing industries yield

considerable amounts of by-products, such as peels, seeds and

pulps, which represents 50% of the raw processed fruit [3b]. These

by-products are valuable source of flavonoids, dietary fibers and

essential oils [1,3c]. Essential oil is one of the most important

Citrus by-products commonly used as a flavoring agent for drinks,

ice cream, and cakes, and as a perfumery agent in air-fresheners and

household products [1,3d]. Moreover, Citrus peel essential oils have

been classified as generally recognized as safe (GRAS) due to their

wide spectrum of biological activities [1,2], such as antimicrobial

[3e], antifungal [3f], Acaricidal [3g], insecticidal [3h], antioxidant

[3i], anti-inflammatory and anxiolytic [4a].

Citrus macroptera and C. maxima are locally known as Haribob

and Nobab in Manipur [4b]. C. macroptera is commonly used by

Manipuri people for spice and medicinal purposes [2,4b]. The fruit of

C. maxima is also used for nutritional purposes and as a cardiotonic,

and the leaves in epilepsy, cholera and convulsive cough [1,2]. Two

cultivars (white and pink) of C. maxima were found to be widely

consumed in Manipur. Literature survey revealed that limonene is a

major compound of Citrus peel oils, but the amount of limonene

was diverse in the different species [1,2]. Though the oils of other

Citrus species have been extensively studied, no detailed analysis

has been reported on the peel oils of these two species growing in

the region. Thus, it was thought worthwhile to isolate the essential

oil from the peels of C. macroptera and C. maxima cultivars and

determine their chemical compositions. The yields of oil ranged

from 0.53% in the peel of C. macroptera to 0.23% in C. maxima

(pink) to 0.13% in C. maxima (white), based on a fresh weight

basis. A total of forty-seven compounds were identified, accounting

for 87.0 to 96.1% of the oils. Limonene (55.3-80.0%), dodecyl

acrylate (2.2-8.0%), geranial (0.4-3.5%), trans-linalool oxide (1.0-

2.8%), -terpineol (0.7-2.3%), linalool (0.7-1.5%) and cis-linalool

oxide (0.5-1.4%) were identified as the major compounds in the

oils. Monoterpene hydrocarbons (57.4-81.5%) constituted the major

portion, followed by oxygenated monoterpenes (3.8-15.6%), and

other groups of compounds (1.1-7.4%). The oil of C. macroptera

contained sesquiterpene hydrocarbons (12.7%) and oxygenated

sesquiterpenes (7.1%), but these groups of compound were absent

in C. maxima oils.

In the oil obtained from the peels of C. macroptera (Haribob),

thirty-seven compounds were identified, accounting for

96.1% of the oil. The main compounds were limonene (55.3%),

β-caryophyllene (4.7%), geranial (3.5%), δ-cadinene (2.8%),

β-eudesmol (2.7%), trans-linalool oxide (2.3%), -terpineol (2.3%),

neral (2.2%), dodecyl acrylate (2.2%), -cadinol (1.7%), geraniol

(1.3%), -copaene (1.2%), cis-linalool oxide (1.2%), linalool

(1.1%), citronellol (1.1%) and β-cubebene (1.1%), together with

three compounds in trace amounts (<0.05%).

The oils of two C. maxima (pink and white) cultivars were also

analyzed. Eighteen compounds, constituting 87.0% of the oil, were

identified in the pink cultivar; the main compounds were limonene

(72.0%), dodecyl acrylate (8.0%), trans-linalool oxide (2.8%),

nootkatone (1.6%), linalool (1.5%), cis-linalool oxide (1.4%) and -

terpineol (1.3%). Likewise, seventeen compounds, accounting for

95.2%, were identified in the white cultivar, with the major

compounds being limonene (80.0%), dodecyl acrylate (7.2%),

nootkatone (2.5%) and trans-linalool oxide (1.0%). Limonene

(55.3-80.0%) was a major compound, but nootkatone (1.6-2.5%)

was identified only in the C. maxima cultivars. Furthermore, C.

maxima (pink and white) cultivars contained higher amounts of

limonene (72.0 and 80.0%) as compared with C. macroptera

(55.3%). Comparing the chemical composition of the oils with

those reported earlier showed that most of the components

identified were similar, with limonene as a major compound [1,2],

but there was considerable quantitative variation between the major

compounds. Thus, it was concluded that the peels of these species

can be used as a source of essential oil as well as limonene, besides

as fruit juice in the region.

NPC Natural Product Communications 2012

Vol. 7

No. 10

1371 - 1372

1372 Natural Product Communications Vol. 7 (10) 2012 Rana and Blazquez

Table 1: Percentage composition of the essential oils of C. macroptera and C. maxima cultivars.

Compound RI RI Lit. Area (%)

CM CMP CMW

Monoterpene hydrocarbons 57.4 73.3 81.5

-Pinene 938 938 0.4 0.2 0.3

Sabinene 977 977 0.2 nd 0.1

β-Pinene 980 980 0.1 nd 0.7

Myrcene 992 992 0.8 0.8 0.1

Limonene 1032 1032 55.3 72.0 80.0

γ-Terpinene 1064 1064 0.6 0.3 0.3

Oxygenated monoterpenes 15.6 11.0 3.8

1,8-Cineole 1035 1035 t nd nd

trans-Linalool oxide 1076 1076 2.3 2.8 1.0

cis-Linalool oxide 1090 1090 1.2 1.4 0.5

Linalool 1100 1100 1.1 1.5 0.7

trans-p-Mentha-2,8-dien-1-ol 1123 1123 nd 0.5 0.2

cis-Limonene oxide 1137 1137 nd 0.7 nd

Terpinene-4-ol 1177 1177 0.4 0.3 0.3

-Terpineol 1192 1192 2.3 1.3 0.7

trans-Carveol 1217 1217 nd 0.8 nd

Citronellol 1226 1226 1.1 nd nd

cis-Carveol 1229 1229 nd 0.6 nd

Neral 1238 1238 2.2 nd nd

Carvone 1244 1244 nd 0.5 nd

Geraniol 1257 1257 1.3 nd nd

Geranial 1269 1269 3.5 0.6 0.4

Citronellyl formate 1274 1274 0.2 nd nd

Sesquiterpene hydrocarbons 12.7 - -

-Copaene 1380 1380 1.2 nd nd

β-Cubebene 1388 1388 1.1 nd nd

β-Elemene 1394 1394 t nd nd

β-Caryophyllene 1419 1419 4.7 nd nd

-Humulene 1454 1454 0.8 nd nd

Germacrene D 1486 1486 0.9 nd nd

Bicyclogermacrene 1500 1500 0. 7 nd nd

-Muurolene 1500 1500 0.3 nd nd

-Farnesene 1506 1506 0.2 nd nd

δ-Cadinene 1523 1523 2.8 nd nd

Oxygenated sesquiterpenes 7.1 nd nd

Elemol 1550 1550 2.7 nd nd

Nerolidol 1563 1563 0.8 nd nd

Cubenol - - 0.3 nd nd

γ-Eudesmol 1632 1632 0.8 nd nd

τ-Muurolol 1642 1642 0.6 nd nd

-Muurolol 1646 1646 0.2 nd nd

β-Eudesmol 1651 1651 t nd nd

-Cadinol 1654 1654 1.7 nd nd

Diterpene nd 1.6 2.5

Nootkatone 1806 1806 nd 1.6 2.5

Other groups of compound 3.3 1.1 7.4

Octanol 993 993 0.2 0.3 nd

Nonanal 1101 1101 0.4 nd nd

Decanal 1202 1202 0.3 nd nd

Methyl eugenol 1403 1403 nd nd 0.2

Hexadecane 1600 1600 0.2 nd nd

Dodecyl acrylate - - 2.2 8.0 7.2

Percentage of different groups of compound identified

Monoterpene hydrocarbons 57.4 73.3 81.5

Oxygenated monoterpenes 15.6 11.0 3.8

Sesquiterpene hydrocarbons 12.7 nd nd

Oxygenated sesquiterpenes 7.1 nd nd

Diterpene nd 1.6 2.5

Other groups of compound 3.3 1.1 7.4

Total percentage of oil identified 96.1 87.0 95.2

RI: Retention Indices, RI Lit.: Retention Indices Literature, CM: Citrus macroptera, CMP: C. maxima (pink),

CMW: C. maxima (white), GC: Gas chromatography, GC-MS: Gas chromatography-Mass Spectrometry, nd:

not detected, t: trace (<0.05%)

Experimental

Plant material: The fresh fruits of C. macroptera and C. maxima

cultivars (pink and white) were collected in July 2007-08 from

Moreh and Imphal, Manipur, and specimens are preserved at the

Institute of Bioresources and Sustainable Development, Imphal.

Isolation of essential oils: The peels of the ripened fruits were

removed and hydrodistilled in a Clevenger type apparatus for 3 h.

The distillate was extracted with diethyl ether, the ethereal layer

dried over anhydrous sodium sulfate, and the diethyl ether removed

by gentle distillation on a heated water bath. The essential oils were

stored at 4-8°C until further analysis.

Gas chromatography and gas chromatography-mass

spectrometry: GC analysis was carried out on a Clarus 500 (Perkin

Elmer) equipped with a flame ionization detector (FID) and a non-

polar HP-1 (crosslinked methylsilicone) capillary column (30 m ×

0.2 mm, 0.33 m film thickness). The oven temperature was held at

60°C for 5 min then programmed at 3°C/min to 180°C and then

20°C/min to 280°C, and held for 20 min. Helium was used as

carrier gas at a flow rate of 1 mL/min. The injection volume was

1μL in split mode (1:25). The injector and detector temperatures

were 220°C and 250°C, respectively. GC/MS analysis was

performed on a Varian Saturn 2000 equipped with a Varian C.SVA-

5MS capillary column (30 m x 0.25 mm i.d., film thickness 0.25

m). Chromatographic conditions were as follows: helium as carrier

gas at a flow-rate of 1 mL/min; injection volume 0.5 L; injector

temperature 250°C. The column temperature was held at 60°C for 5

min., and programmed at 3°C/min to 180°C and then 20°C/min to

300°C and held for 20 min with split mode injection (1:25). The

column was coupled directly to the quadrupole mass spectrometer

in EI mode at 70 eV with a mass range of 28-400 a.m.u. at 1 scan/s.

Kovat’s retention indices were calculated using chromatographed

standard hydrocarbons. The individual compounds were identified

by comparing their retention indices and mass spectra with data

available in the NIST2005 Mass Spectral Library and literature [4c].

Acknowledgments - Authors are thankful to the Department of

Science and Technology, Govt. of Manipur for financial support and

the Director, IBSD, Imphal for necessary facilities and to Dr

Biseshwori Th., Scientist-C (Plant taxonomy) of the institute for

identification of plant species.

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Jan 2022

(+)-Nootkatone is a type of eremophilane naturally derived sesquiterpenoids with a grapefruit smell from plants, which is widely used in food and cosmetics industries. Many investigations elucidated (+)-nootkatone presents extensive pharmacological activity, such as anti-proliferation in cancer cells, anti-inflammatory, antioxidant nitration stress, etc. In addition, (+)-nootkatone has been registered by the Environmental Protection Agency as a new active ingredient for use in insecticides and insect repellents against ticks, mosquitoes, and a wide variety of other biting pests. On account of the increasingly stringent environmental supervision and market demand for “natural” (+)-nootkatone, the explorations for producing this high-value chemical by green chemosynthesis and biosynthesis technology are in progress. Structural derivatization is becoming one of the most important ways to exploit pharmaceutical and ecological applications. This review covered the progress of the above research and application advances comprehensively to encourage interested scientists to implement further studies.

Lesser known edible fruits of Karbi Anglong district of Assam

Article

Full-text available

May 2021

Fruits are one of the prime sources of vitamins and nutrients for a healthy life. Likewise, many lesser known and minor fruits are present in this biodiversity still yet to explore. The present study has been carried out with an objective to explore, identify and document some of the wild edible fruit species consumed by rural masses of Karbi Anglong district of Assam. In this study, a total of 13 species belonging to 10 families have been recorded along with their scientific names, family, local names in Karbi and Dimasa, time of availability, taste, colour on maturity, seed number, flower colour, consumption and use of folk medicines. The study revealed that amongst all the fruits collected, most have an immense potential for use as medicines. These fruits can be the source of many future medicines but only after following several procedures and researches.

Identification of essential oil components by gas chromatography / mass spectroscopy

Book

Full-text available

Jan 1995

Robert P. Adams

Biodiversity Significance of North East India

Technical Report

Full-text available

Jun 2006

Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci

Article

Full-text available

Oct 2012
NAT PROD COMMUN

Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound I was the first example with a Z-configuration of the C-4'/C-5' double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines.

Physico-Chemical Characteristics of Citrus Seeds and Seed Oils from Pakistan

Article

Full-text available

Apr 2008

The physico-chemical characteristics of the seeds and seed oils of four citrus species, Mitha (Citrus limetta), Grapefruit (Citrus paradisi), Mussami (Citrus sinensis), and Kinnow (Citrus reticulata) were investigated. The hexane-extracted oil content of citrus seeds ranged from 27.0 to 36.5%. The protein, fiber and ash contents were found to be 3.9–9.6%, 5.0–8.5%, and 4.6–5.6%, respectively. The extracted oils exhibited an iodine value of 99.9–110.0; refractive index (40°C), 1.4639–1.4670; density (24°C), 0.920–0.941mg/mL; saponification value, 180.9–198.9; unsaponifiable matter, 0.3–0.5%; acid value (mg KOH/g of oil), 0.5–2.2 and color (1-in. cell) 1.4–3.0R+15.0–30.0Y. The oils revealed a good oxidative stability as indicated by the determinations of specific extinctions at 232 and 270nm (2.3–4.4 and 0.6–0.9, respectively), p-anisidine value (2.2–3.2) and peroxide value (1.6–2.4mequiv/kg of oil). The citrus seed oils mainly consisted of linoleic acid (36.1–39.8%). Other prominent fatty acids were palmitic acid (25.8–32.2%), oleic acid (21.9–24.1%), linolenic acid (3.4–4.4%), and stearic acid (2.8–4.4%). The contents of tocopherols (α, γ, and δ) in the oil were 26.4–557.8, 27.7–84.1, and 9.1–20.0mg/kg, respectively. The results of the present study demonstrated that the seeds of citrus species investigated are a potential source of valuable oil which might be utilized for edible and other industrial applications.

Insecticidal Activity Against Bemisia tabaci Biotype B of Peel Essential Oil of Citrus sinensis var. pear and Citrus aurantium Cultivated in Northeast Brazil

Article

Full-text available

Nov 2010
NAT PROD COMMUN

The fumigant action of peel essential oils of Citrus sinensis var. pear (pear orange = PO) and C. aurantium (bitter orange = BO) from the northeast of Brazil were evaluated against Bemisia tabaci biotype B and compared with eugenol as a positive control. The oil concentration in the PO at 8.5 microL/L of air caused 97% mortality, while the oil concentration of BO at 9.5 microL/L of air caused 99% mortality. However, the LC50 estimates for both oils (LC50 = 3.80 microL/L of air for PO and LC50 = 5.80 microL/L of air for BO) did not differ from each other, but they did when compared with eugenol (LC50 = 0.20 microL/L of air). Regarding their effects on oviposition, the Citrus oils showed concentration-response dependence, reducing the number of eggs as the concentration increased, which was not observed for eugenol. The minimum concentrations of the oils that caused a significant reduction in the egg lay were 3.5 and 7.0 microL/L of air for BO and PO, respectively. These results suggest that oils from PO and BO peels may be promising as models to develop new insecticides that might be applied into the integrated management of whiteflies.

Glossary of Indian Medicinal Plants

Article

Jan 1986

Citrus peel extract – A natural source of antioxidant

Article

Dec 2006
FOOD CHEM

Zia Ur Rehman

Citrus peel extract as a natural source of antioxidant was evaluated during 6 months storage of refined corn oil at 25 and 45 °C. Extracts of citrus peel were prepared by refluxing the dried ground peel with ethanol, methanol, acetone, hexane, diethyl ether and dichloromethane. Maximum amount of citrus peel extract was obtained with methanol. Antioxidant activity of methanolic extract was assessed by measuring free fatty acid (FFA) content peroxide value (POV) and iodine value (IV) during 6 months storage of refined corn oil at 25 and 45 °C. After 6 months of storage at 45 °C, corn oil containing 1600 and 2000 ppm citrus peel extract, showed lower FFA contents (1.5% and 1.0%), and POVs (8.38 and 7.0 meq kg−1) and higher iodine values (81, 89) than the control sample (FFA 17.0% POV 101 meq kg−1 IV 47). Refined corn oil containing 200 ppm of butylated hydroxy anisole (BHA) and butylated hydroxy toluene (BHT) showed FFA contents of 2.0% and 1.8%, POVs 17.0 and 12.7 meq kg−1 and IVs 84 and 87, respectively, after 6 months of storage at 45 °C. These results show that methanolic extract of citrus exhibited very strong antioxidant activity, which was almost equal to synthetic antioxidants (BHA and BHA). Therefore, the use of citrus peel extract is recommended as a natural antioxidant to suppress development of rancidity in oils and fats.

Effective drying of citrus by-product by high speed drying: A novel drying technique and their antioxidant activity

Article

May 2009
J FOOD ENG

The citrus by-products (CBP) released from the citrus processing plants may contain high amount of potential bioactive compounds. Hence, this study aims to evaluate the antioxidant activity of CBP prepared using a novel drying technique known as high speed drying (HSD), economically and efficiently. HSD extract showed high amount of polymethoxylated flavones (heptamethoxyflavone and nobiletin) and flavanone (hesperidin and naritutin). The antioxidant activity was evaluated by means of DPPH, hydroxyl and alkyl radical scavenging assays and lipid peroxidation assay. HSD extract showed strong activities on radical scavenging (IC50 value of DPPH, hydroxyl and alkyl radicals scavenging were 0.16, 0.5, 0.019mg/mL, respectively) and lipid peroxidation inhibition. These results suggest that the flavonoids and other phenolic compounds in the HSD extract could be good radical scavengers. Hence, HSD method is an effective and efficient method to transform citrus by-products into dried form and could be used in food and pharmaceutical industry as a natural antioxidant agent.

Potential antimicrobial uses of essential oils in food: Is citrus the answer?

Article

Mar 2008
TRENDS FOOD SCI TECH

The antimicrobial properties of essential oils (EOs) have been recognised for centuries and, with growing demand from changes in legislation, consumer trends and increasing isolation of antibiotic resistant pathogens, alternatives to chemical-based bactericides need to be found. Citrus oils not only lend themselves to use in food but also are generally recognised as safe (GRAS) and have been found to be inhibitory both in direct oil and vapour form against a range of both Gram-positive and Gram-negative bacteria. This group of oils may provide the natural antimicrobials that the food industry requires to fulfil both its requirements and those of the consumer.

Antifungal activity and chemical composition of Citrus reticulata Blanco essential oil against phytopathogens from North East India

Article

Apr 2009
LWT-FOOD SCI TECHNOL

The essential oil (EO) isolated by hydro-distillation from the peel of fully matured ripen fruits of Citrus reticulata Blanco were analyzed by GC and GC–MS. Thirty seven different components were identified constituting approximately ≥99% of the oil. The major components were limonene (46.7%), geranial (19.0%), neral (14.5%), geranyl acetate (3.9%), geraniol (3.5%), β-caryophyllene (2.6%), nerol (2.3%), neryl acetate (1.1%) etc. The antifungal activity of the oil was tested by poisoned food (PF) technique and the volatile activity (VA) assay against five plant pathogenic fungi viz Alternaria alternata (Aa), Rhizoctonia solani (Rs), Curvularia lunata (Cl), Fusarium oxysporum (Fo) and Helminthosporium oryzae (Ho). The oil showed better activity in VA assay. The Minimum inhibitory concentration (MIC) for Aa, Rs and Cl was 0.2 ml/100 ml whereas >0.2 ml/100 ml for Fo and Ho in PF technique. Fungal sporulation was also completely inhibited at 2 ml/100 ml of the oil except for Cl and Ho, which was only 0.5% (±0.5) and 0.25% (±0.25) respectively as compared to control.