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 Table of Contents  
ORIGINAL ARTICLE
Year : 2017  |  Volume : 37  |  Issue : 1  |  Page : 37-44

New triterpenic compounds from Swertia chirata


1 Department of Pharmacognosy, Delhi Institute of Pharmaceutical Sciences and Research, University of Delhi, New Delhi, India
2 School of Pharmacy, Sharda University, Greater Noida, Uttar Pradesh, India
3 Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, New Delhi, India

Date of Web Publication13-Jul-2018

Correspondence Address:
Sakshi Bajaj
Delhi Institute of Pharmaceutical Sciences and Research, University of Delhi, Pushp Vihar, Sector III, Mehrauli-Badarpur Road, New Delhi
India
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/asl.ASL_5_18

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  Abstract 

Aim: To study the Phytochemical constituents of dried aerial parts of Swertia chirata Linn (family Gentianaceae). Methods: The ethanolic extract of the aerial parts of plant S. chirata was subjected to column chromatography and was eluted with petroleum ether and chloroform of various concentrations to yield compound SC-1, 2 and 3 and their structures were elucidated on the basis of chemical methods and spectral techniques such as Ultraviolet (UV), Fourier Transform Infrared (FTIR), Hydrogen Nuclear Magnetic Resonance (1HNMR), Carbon Nuclear Magnetic Resonance (13CNMR), and Mass spectrometry (MS). Results: Three compounds were isolated and their structures were determined as (a) Olean-12-ene-18α H-3-one-9α-ol, (b) Olean-12-ene-18α H-3-one-19β-ol and (c) Olean-12-en-18α H-3-one. Conclusion: Chemical and spectral investigation of extract furnished three novel oleanenone triterpene glycosides from the genus Swertia for the first time.

Keywords: Elucidation, glycoside, isolation, Swertia, oleanenone


How to cite this article:
Bajaj S, Singh V, Ali M. New triterpenic compounds from Swertia chirata. Ancient Sci Life 2017;37:37-44

How to cite this URL:
Bajaj S, Singh V, Ali M. New triterpenic compounds from Swertia chirata. Ancient Sci Life [serial online] 2017 [cited 2018 Dec 16];37:37-44. Available from: http://www.ancientscienceoflife.org/text.asp?2017/37/1/37/236549


  Introduction Top


The genus Swertia belongs to family Gentianaceae which is known to have about 700 species and 80 genera.[1] In India, 40 species of Swertia are recorded [2],[3] of which, Swertia chirata is considered the most important for its medicinal properties. S. chirata was first described by Roxburgh under the name of Gentiana chyrayta in 1814.[4]

Swertia species are common ingredients in a number of herbal remedies. S. chirata is commonly known as “Chiretta”. This plant is widely used in Ayurvedic, Unani and Siddha systems of Medicine.[5] It is a critically endangered medicinal herb that grows at high altitudes in the sub-temperate regions of the Himalayas between 1200 and 2100 m altitudes from Kashmir to Bhutan [2],[6] on the slopes of moist shady places.[7]

It is used in the traditional system of medicine (TSM) as antiseptic and curative of fevers, urinary disorders, skin diseases, cough and poisoning.[8] Several species of Swertia are highly exploited as raw material for different traditional medicines. Among them, S. chirata is considered to be superior in medicine and trade.[9] This plant is widely used in Ayurvedic, Unani and Siddha systems of Medicines.[5] Chirata is an important component of the Ayurvedic tonic “Sudarśana Cūrṇa”. In traditional medicine the entire plant is used but the root is the richest source of active phytochemicals.[10] Previous phytochemical studies of S. chirata have resulted in the isolation of xanthone derivatives,[11],[12],[13],[14],[15],[16],[17] triterpenoids [18],[19],[20],[21] secoiridoid glycoside,[22] lignin,[23] bitter principle,[22] alkaloids [24] and phenolics.[25] Literature survey revealed that not much work was done on the aerial parts of the plant. Among the many pharmacological activities possessed by the S. chirata such as anti-hepatotoxic,[26] anti-inflammatory,[27] antiulcerogenic,[27] antimalarial [28] and hypoglycaemic.[29] Its widespread uses in traditional medicine have resulted in over-exploitation in its natural habitat and is now on the verge of extinction in the wild. S. chirata is also known by an array of names such as Anāryatikta, Bhūnimba, Ciratitka, Kairāta in Sanskrit, Qasabuzzarirah in Arabic and Persian, Chiaravata in Urdu, Sekhagi in Burmese, and Chirrato or Chiraita in Nepalese.[30]

Due to the many therapeutic properties of this plant, we decided to look at the phytochemistry of S. chirata. In this paper we report the isolation and structural elucidation of three novel oleanenone triterpene glycosides. (a) Olean-12-ene-18α H-3-one-9α-ol, (b) Olean-12-ene-18α H-3-one-19β-ol and (c) Olean-12-en-18α H-3-one. None of these compounds has been isolated earlier from any other parts of the plant.

Material and Methods

General experimental procedure

Melting points were uncorrected. IR spectra were recorded as KBr pellets on Nicolet FTIR spectrophotometer. MS were recorded by effecting electron impact ionization at 70 eV on an ESIMS analyst QS TOF (Canada) mass spectrometer.1 H and 13 C NMR spectra were scanned on Bruker DRX-300 NMR (300 MHz) instrument in CDCl3 and D2O using tetramethylsilane (TMS) and CDCl3 as the internal standard. The coupling constants (J values) are expressed in Hertz (Hz). Silica gel G (Qualigen, 60-120 mesh) was used for column chromatography. TLC was performed on plates coated with silica gel G (E. Merck, Germany).

Plant material

The dried plant material was purchased from the local market of Delhi, Khari Baoli and identified by Dr. M.P Sharma, Taxonomist, Department of botany, Faculty of Science, Jamia Hamdard (Hamdard University). The voucher specimen (PRL/JHMD/08/13) of the test drug was deposited in the herbarium of Ram-eesh institute of vocational and technical education, Greater Noida for future reference.

Extraction and isolation

In the present study, the aerial parts were carefully collected and air dried under shade. The air dried materials were reduced to coarse powder. The coarse powdered material (2.0 kg) was subjected to exhaustive extraction with 95% ethanol in a Soxhlet apparatus for 50 hours. The extract was concentrated in a rotary evaporator under vacuum to obtain dried greenish brown coloured 105 g (5.25%) residue. The residue was chromatographed on a silica gel column. The column was eluted successively using solvent system of petroleum ether and chloroform to isolate the phytoconstituents.


  Result and Discussions Top


Compound SC 1

SC-1 [Figure 1] was obtained as colourless crystals from elution of the column with petroleum ether-chloroform (2:3) that were later recrystallized from acetone. The compound SC-1 responded positively to the tests of steroids and showed an Rf value of 0.78 in the petroleum ether: chloroform (3:2) solvent system. The melting point for isolated compound SC-1 was determined by the open capillary method and was recorded as 211 – 212°C, which was uncorrected. The compound SC-1 showed IR bands at 3453, 2930, 2858, 2369, 1710, 1633, 1456, 1330, 1239, 1113, 1040 cm -1. The positive FAB-MS showed mass to charge ratio (m/z) (Relative Intensity) at 441[M + 1]+ (18.9), 440 [M]+ (C30H48 02) (6.3), 425 (24.3), 422 (31.8), 410 (100), 407 (60.3), 398 (23.1), 395 (11.6), 392 (12.5), 384 (15.3), 381 (14.2), 380 (12.3), 222 (21.5), 218 (62.8), 205 (65.1), 203 (87.2), 191 (71.6), 190 (75.3), 188 (69.7), 176 (63.1), 175 (62.9), 173 (59.6), 161 (63.4), 160 (68.2), 158 (73.1), 146 (53.2), 131 (57.6), 95 (77.6). The structure of compound SC-1 was further supported by the 1 H-NMR and 13 C-NMR data given in [Table 1].
Figure 1: Swertiaoleanenone A

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Table 1: 1Hydrogen nuclear magnetic resonance and carbon nuclear magnetic resonance values of Swertiaoleanenone A

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Compound SC 1 named as swertiaoleanenone A, was obtained as a colorless crystalline mass from petroleum ether: chloroform (2:3) elutants. It responded positively libermann burchard test and zimmermann test [31] indicating its triterpenic nature of the molecule with 3-keto group. It had characteristic IR absorption bands for hydroxyl groups (3453 cm -1), carbonyl groups (1710cm -1) and unsaturated groups. The mass spectrum of compound SC 1 exhibited a molecular ion peak at m/z 440 consistent with the molecular formula C30H48O. It indicated seven double bond equivalents; five of them were adjusted in the pentacyclic carbon skeleton and one each in the carbonyl function and unsaturation.

The ion fragments arising at m/z 425 [M-Me]+, 410 (425-Me)+, 395 (410-Me)+, 380 (395-Me)+, 384 [M-CH2 CH2 CO], 398 [M-CH2 CO]+, 422 [M-H2O]+, 407 (422-Me)+ and 392 (407-Me)+ supported the existence of the carbonyl and hydroxyl groups in the molecule. The ion peaks at m/z 222 and 218 were generated due to retro Diels-Alder fragmentation pattern indicating the location of the vinylic linkage in ring C and the keto and hydroxyl function in ring A/B.[32],[33] The ion peaks produced at m/z 205 (222-OH)+, 190 (205-Me)+, 175 (190-Me)+ and 160 (175-Me)+ and also suggested the presence of the hydroxyl group in the ring A/B. The ion peaks appearing at m/z 203 (218-Me)+, 188 (203-Me)+, 173 (188-Me)+, 158 (173-Me)+, 131 (158-CHCH2)+, 191 (218-CHCH2)+, 176 (191-Me)+, 161 (176 - Me)+ and 146 (161-Me)+ and indicated the existence of four methyl functions in the saturated rings D and E [Scheme 1].



The 1 HNMR spectrum of SC 1 displayed a one proton doublet at δ 5.43 (J = 3.1 Hz) assigned to vinylic H-12 proton. Eight broad signals at δ 0.89, 1.01, 1.11, 0.78, 1.01, 1.25, 1.04 and 0.94 were ascribed to tertiary C-23, C-24, C-25, C-26, C-27, C-28, C-29 and C-30 methyl protons, all located on the saturated carbons. A one proton double doublet at δ 2.26 (J = 3.0 Hz) was attributed α oriented H-18 methine proton.

The remaining ethylene and methane protons resonated between δ 2.76-1.21. The absence of any signal between δ 5.43-2.76 indicated tertiary nature of the hydroxyl group. The 13 CNMR spectrum of SC 1 exhibited 30 carbon signals and the important signals were displayed at δ 145.15 (C-13), 116.10 (C-12), 68.47 (C-9), 207.61 (C-3) and methyl carbons between δ 24.53-12.55. The 13 CNMR values were compared with the reported values of Oleanone type triterpenoids.[33],[34] On the basis of the spectral data analysis and chemical reactions the structure of SC 1 has been elucidated as olea-12-en-18α H-3-one-9α-ol.

Compound SC 2

SC-2 [Figure 2] was obtained as colourless crystals from elution of the column with petroleum ether: chloroform (1:4) that were subsequently recrystallized from acetone. The compound SC-2 responded positively to the tests of steroids and showed an Rf value of 0.85 in the petroleum ether: chloroform (1:4) solvent system. The melting point for isolated compound SC-2 was determined by the open capillary method and was recorded as 181 – 182°C, which was uncorrected. The compound SC-2 showed IR bands at 3437, 2945, 2859, 1707, 1644, 1463, 1379, 1035, 808 cm -1 and UV absorption maxima at 253 nm in methanol. The positive FAB-MS showed m/z (Relative Intensity) at 440 [M]+ (C30H48O2) (5.5), 425 (33.6), 422 (18.2), 410 (63.5), 407 (28.8), 398 (15.1), 395 (10.2), 392 (10.3), 380 (5.5), 368 (5.1), 234 (6.1), 219 (23.7), 216 (15.4), 206 (51.8), 204 (38.6), 201 (22.3), 192 (46.3), 191 (33.8), 189 (32.3), 186 (21.9), 177 (29.6), 176 (32.5), 174 (21.0), 171 (32.7), 162 (31.9), 161 (33.1), 147 (60.3), 146 (52.3). The structure of compound SC-2 was further supported by the 1 H-NMR and 13 C-NMR data given in [Table 2].
Figure 2: Swertiaoleanenone B

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Table 2: 1Hydrogen nuclear magnetic resonance and 13carbon nuclear magnetic resonance values of Swertiaoleanenone B

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Compound SC 2 named as swertiaoleanenone B was obtained as a colorless crystalline mass from petroleum ether: chloroform (1:4) elutants. The compound was characterized with IR signal at (γ max 3437 (OH), 1707 (CO) and 1644 (C = C) cm-1) and mass signal at (M + m/z 440, C30H48O2). The ion fragment arising at m/z 425 [M-Me]+, 410 (425-Me)+, 395 (410-Me)+, 380 (395-Me)+, 398 {M-CH2 CO]+, 368 (398-2xMe)+,422 [M- H2 O]+, 407 (422-Me)+ and 392 (407-Me)+ indicated the presence of one each hydroxyl and keto groups in the molecule. The ion peaks generated at 206 and 234 m/z due to retro-Diels-Alder fragmentation pattern supported the existence of the carbonyl group in ring A/B, which was placed at C-3 on the basis of biogenetic consideration, and the hydroxyl group in rings D/E. The ion peaks at m/z 191 (206 - Me)+, 176 (191 - Me)+, 161 (176 - Me)+ and 146 [16 - Me]+ were formed due to subsequent expulsion of the methyl groups from the mass unit 206 [C14H22O]+.

The ion peaks appearing at m/z 216 (234- H2 O)+, 201 (216- M e)+, 186 (201-Me)+ and 171 422 (186-Me)+ supported the location of the hydroxyl group in ring D/E. The stepwise removal of the methyl groups from the mass unit 234 [C16H26O]+ produced the ion fragments at m/z, 219 (234-Me)+, 204 (219-Me)+, 189 (204-Me)+, 174 (189-Me)+, 192 (219-CHCH2)

+, 177 (192-Me)+, 162 (177-Me)+ and 147 (162-Me)+ [Scheme 2].



The 1 HNMR spectrum of SC 2 displayed a one-proton doublet at 5.34 (J = 5.1Hz) assigned to vinylic H-12 proton. Two one proton doublet at δ 3.56 (J = 5.7) and 2.68 (J = 5.7Hz) were accounted correspondingly to α- oriented H-19α carbinol and H-18α methane protons. The methyl signals appeared between δ 1.17-0.70 indicating that all these functions were located on the saturated carbons. The remaining ethylene and methane carbons appeared between δ 2.27-1.39. The 13 CNMR spectrum of SC 2 exhibited 30 carbon signals and the important signals resonated for carbonyl carbon at δ 207.03 (C-3), vinylic carbons at δ 116.09 (C-12) and 143.96 (C-13), carbinol carbon at δ 78.02 and methyl carbons between δ 27.79-12.61. The 13 CNMR values of SC2 were compared to the reported values of the oleanone type triterpenoids.[33],[34] On the basis of spectral data analysis and chemical reactions the structure of SC 2 has been established as olean-12-en-18α H-3-One-19β-ol.

Compound SC 3

SC-3 [Figure 3] was obtained as colorless needle shaped crystals from the elution of the column with petroleum ether: chloroform (3:7) which were then recrystallized from acetone. The compound SC-3 responded positively to the tests of steroids and showed Rf value of 0.64 in the petroleum ether: chloroform (1:1) solvent system. The melting point for isolated compound SC-3 was determined by the open capillary method and was recorded as 191 – 192°C, which was uncorrected. The compound SC-3 showed IR bands at 2947, 2860, 1704, 1640, 1457, 1378, 1255, 1106, 1014, 808 cm -1 and UV absorption maxima at 246 nm in methanol. The positive FAB-MS showed m/z (Relative Intensity) at 425 [M+1]+ (98.1), 424 [M]+ (C30H48O) (76.8), 409 (86.5), 394 (25.2), 379 (13.1), 218 (26.7), 206 (68.5), 203 (63.6), 191 (65.2), 188 (59.7), 176 (31.5), 173 (47.2), 158 (63.2), 161 (40.3), 146 (71.9). The structure of compound SC-3 was further supported by the 1 H-NMR and 13 C-NMR data given in [Table 3].
Figure 3: 18-αH-oleanenone

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Table 3: 1HNMR and 13CNMR values of 18-αH-oleanenone

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Compound SC 3: Compound SC 3 named as 18-α H- oleanenone, was obtained as colorless needle shape mass from petroleum ether: chloroform (1:4) elutant. It gave positive result on Zimmermann test [31] indicating 3-oxotriterpenoid nature of the molecule. Its IR spectrum exhibits distinctive absorption bands for carbonyl group (1704 cm -1) and unsaturation (1640 cm -1). On the basis of positive ion, FAB mass spectrum and 13 C NMR values the mass weight was established at m/z 424 consistent with the molecular formula of a triterpenoid, C30H48O. It indicates seven double equivalents; five of them were adjusted in the pentacyclic carbon framework of the triterpenoid and one each in the vinylic linkage and carbonyl group. The mass spectrum of SC 3 exhibited important ion Fragments at m/z 409 [M - Me]+, 394 (409 - Me)+ and 379(394 - Me)+ Indicating the presence of tertiary methyl groups in the molecule. The Ion fragments at m/z 206 [C14H22O]+ and 218[C16H26]+ were generated due to retro-Diels-Alder fragmentation pattern of the molecules Suggesting the existence of the vinylic linkage in the ring c [32],[33] and the oxygenation in ring A/B which was placed at C-3 on the basis of biogenetic consideration. The ion peaks at mHz 191(206 - Me)+, 176 (191 - Me)+, 161 (176 - Me)+, 146 (161- Me)+, 203 (218 - Me)+, 188 (203 - Me)+, 173 (188 - Me)+ and 158 (173 - Me)+ were formed due to subsequent expulsion of the methyl functions from the Mass units 206 and 218 supporting the location of eight tertiary methyl groups in the molecule [Scheme 3].



The 1 HNMR spectrum of SC 3 showed a one proton multiplet at δ 5.37 assigned to vinylic H-12 proton. A one proton doublet at δ 2.28 with coupling interactions of 5.7 and 5.4 Hz was attributed to α-oriented H-18 methine proton. Four one proton doublets at δ 2.06 (J = 5.4, 5.7Hz), 2.64 (J = 5.4, 5.7Hz), 2.72 (J = 5.7, 5.4Hz) and 2.06 (J = 3.7, 3.2Hz) were attributed to methylene H2-1a and to H2-2a, H-2b ethylene protons adjacent to the carbonyl group and to α-oriented H-5 methine protons. Broad signals between δ 1.18-0.82, all integrated for three protons each were ascribed to tertiary C23 – C30 methyl protons attached to the saturated carbons. The 13 C NMR spectrum of SC 3 exhibited 30 carbon Signals including the important signals for carbonyl carbon at δ 206.83(C-3), vinylic carbons at δ116.10 (C-12), δ145.14 (C-13) and methyl carbons between δ 27.81-12.46. The 13 C NMR values Of SC 3 were compared with the reported values of Oleanenone type Triterpenoids.[33],[34] On the basis of the foregoing discussion the structure of SC 3 has been formulated as olean-12-en-18α H-3-one.


  Conclusion Top


S. chirata offers many promising prospects for both traditional and modern medicine. Overexploitation combined with habitat destruction has resulted in the drastic reduction of its population. For the successful commercialization of this critically endangered medicinal plant any proposed research must be viewed in a wider context.

Exploration of chemical constituents is required for establishing mechanisms of action of possible markers and structure-activity-relationship among the constituents present in the root, stem-bark and leaves which will give us the basis for its therapeutic use. S. Chirata can be used as a good source of active therapeutics. In Indian market, there are many Ayurvedic preparations containing S. Chirata that are widely utilized for curing various ailments. So far no serious side effects or toxicity of S. chirata have been reported, but further toxicological studies are still needed to confirm the safety of S. chirata in humans. These studies will be helpful for the development of active molecules and clinical trials a tool for development of Ayurvedic formulations. Efforts are required for further studies, especially evaluating its biological activities in vivo and toxicological properties. Depending on the primary information available on, this plant, the isolation and identification of active constituents, modern pharmacological evaluations on isolated compounds and their toxicity testing is to be explored. Thus, this article provides an easily accessible source of ecological biodiversity, traditional uses and phytochemistry of S. chirata.

Financial support and sponsorship

Nil.

Conflicts of interest

There are no conflicts of interest.

 
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    Figures

  [Figure 1], [Figure 2], [Figure 3]
 
 
    Tables

  [Table 1], [Table 2], [Table 3]



 

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