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Original article
03 2022
:16;
104511
doi:
10.1016/j.arabjc.2022.104511

Ceratoluteolin: A new flavonoid from Salvia ceratophylla from Jordan

, , ,
a Department of Chemistry, Faculty of Science, Al-Balqa Applied University, Al-Salt, Jordan
b Department of Chemistry, School of Science, The University of Jordan, Amman, Jordan
c Department Department of Chemistry, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia
d Department of Chemistry, Faculty of Science, Yarmouk University, Irbid, Jordan
e Department of Chemical Engineering, Faculty of Engineering Technology, Al-Balqa Applied University, Amman, Jordan

⁎Corresponding author. hala.aljaber@bau.edu.jo (Hala I. Al-Jaber)

Received: , Accepted: ,
© The Author(s) 2022
Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

Abstract

Ceratoluteolin 1, a new luteolin derivative was isolated from Salvia Ceratophylla growing wild in Jordan along with other 14 known compounds including two sterols, two triterpenes, four flavonoids and six phenolic compounds, one of which is reported for the first time from Lamiaceae family. The isolated compounds were genkwanin-4′-methyl ether 2, β-sitosterol 3, oleanolic acid 4, ursolic acid 5, apigenin 6, β-sitosteryl glucoside 7, p-hydroxyphenyl caffeate 8, caffeic acid 9, shimobashiric acid B 10, methyl rosmarinate 11, butyl rosmarinate 12, luteolin 13, luteolin-7-O-glucoside 14 and rosmarinic acid 15. Complete structural verification of the isolated compounds was achieved by careful inspection of their spectral data including NMR (1D & 2D) and HREIMS.

Keywords

Salvia ceratopylla
Ceratoluteolin
Flavonoids
Phenolic acids
1

1 Introduction

The use of Salvia plants in traditional medicine dates back in time as evident from the use of many Salvia species, especially in the Middle East, for the treatment of many ailments like colds, bronchitis, tuberculosis, hemorrhage and menstrual disorders (Topçu, 2006). Additionally, traditional healers in Jordan, Palestine, Syria and other neighbouring countries prescribe herbal teas prepared from several Salvia species for the treatment of microbial infections, coughs, and urinary disorders (Al-Jaber et al., 2012b; Al-Jaber 2015). Among the different Salvia species, Salvia ceratophylla has been used for the treatment of inflammations, fungal and nociceptive diseases (Abu-Darwish et al., 2020).

Salvia ceratophylla L., belonging to the Lamiaceae family (formerly known as Labiateae) is one of the 25 indigenous Salvia species native in Jordan. It is a perennial herb, 20–50 cm long, erect with soft green-yellow to purple branches that are covered with white dense hairs. Flowers are 1.5 cm long and lemon-yellow coloured. Flowering occurs in spring season, during the period extending from April to May (Al-Eisawi, 1998). In Jordan, S. ceratophylla has been reported to grow wild in different regions along the country, but mainly in waste lands and road sides of Irbid, Amman, Tafila, Shoubak, Petra, Ma’an and Mafraq, all belonging to the Mediterranean geographical zone.

Literature survey revealed that S. ceratophylla has been investigated for its essential oil composition (Mehdi et al., 2010; Karataş and Ertekin, 2010; Gürsoy et al., 2012; Bşer et al., 2015; Kilic 2016; Al-Jaber 2016), antioxidant activity (Gürsoy et al., 2012) and antimicrobial activity (Karataş and Ertekin, 2010). Extracts of S. ceratophylla have also been investigated for their anti-inflammatory activity (Bonesi et al., 2017; Shehadeh et al., 2014) in vitro anticholinesterase and antioxidant activities (Orhan et al., 2007), in addition to antiproliferative activity (Abu-Dahab et al., 2012; Mirzaei et al., 2019). Previous phytochemical investigation of S. ceratophylla roots resulted in the isolation of two new diterpenes (Gören et al., 2002), and seco-4,5-abietane diterpenoids (Mirzaei et al., 2019). It’s worth mentioning that this plant has never been investigated thoroughly for its secondary metabolite constituents, especially in Jordan.

Previously, our research group have reported the isolation, structural elucidation and bioactivity evaluation of several new compounds from Salvia plants growing wild in Jordan (Al-Jaber et al., 2012a; Al-Qudah et al., 2014; Barhoumi et al., 2022; Hasan et al., 2016). Following our interest in Salvia species, we report here the isolation and structural elucidation of one new flavone derivative, ceratoluteoline 1 (Fig. 1), along with other 14 known compounds from S. ceratophylla from Jordan.

Ceratoluteolin (1) isolated from S. ceratophylla from Jordan.
Fig. 1
Ceratoluteolin (1) isolated from S. ceratophylla from Jordan.

2

2 Experimental

2.1

2.1 General

1H NMR spectra were recorded on a Bruker Avance III 500 MHz spectrometer with TMS as an internal standard. 13C NMR spectra were recorded at 125 MHz. High resolution mass spectra (HRESIMS) were acquired by electrospray ionization in the positive mode technique using a Bruker APEX-4 Mass spectrometer. TLC was performed on silica gel 60 GF254 pre-coated glass plates (0.25 or 0.50 mm in thickness, Macherey-Nagel). Compounds were visualized under UV light or spraying with sulfuric acid-anisaldehyde spraying reagent followed by heating.

2.2

2.2 Plant material

Aerial parts of S. Ceratophylla were collected from Abu-Nusair region along Jordan Highway, north of Amman, Jordan, during the flowering period (March-April, 2015). The plant was identified by Prof. Hala I. Al-Jaber (Department of Chemistry, Faculty of Science, Al-Balqa Applied University, Al-Salt, Jordan). A voucher specimen (No: SC/LAM/2015) was deposited at the Herbarium of Al-Balqa Applied University, Al-Salt, Jordan.

2.3

2.3 Extraction and isolation of components

Extraction of the plant material was performed according to the procedure mentioned in the literature (Al-Jaber et al., 2012a). Briefly, the dried, ground aerial parts of S. ceratophylla (6.5 kg) was defatted with petroleum ether (30 L) and then extracted with ethanol repeatedly (20 L, five times, 6 days each) at room temperature. After evaporating ethanol at reduced pressure, the obtained gummy residue (230 g) was partitioned between chloroform and H2O. The reduced chloroform extract was then subjected to partitioning between n-hexane and MeOH/H2O (9:1, v/v) mixture (1:1, v/v) affording the hexane extract (SCH, 65 g) and the aqueous methanol extract (SCA, 55 g). Polar compounds in the water fraction were extracted using n-butanol (1:1, v/v) affording the butanol fraction (SCB, 46 g) and water fraction (SCW, 64 g).

SCA fraction (55 g) was chromatographed on a normal phase silica gel column (Macherey-Nagel, 400 g) packed in CH2Cl2 and eluted with a gradient of CH2Cl2/MeOH mixture of increasing polarity until pure MeOH was used and the obtained fractions were then grouped according to their TLC behaviour into 10 collective fractions (SCA I–X). Each of the collective fractions was chromatographed on a silica gel column eluted with Toluene/ethyl acetate mixtures of increasing polarity. The resulting fractions were further purified by size exclusion chromatography utilizing Sephadex LH-20, TLC using suitable solvent systems and/or recrystallization to give the pure compounds. The isolated pure compounds were then identified by analysis of their spectral data. Fraction SCA-II (0.9 g) afforded genkwanin 4′-methyl ether 2 (20 mg) and β-sitosterol 3 (50 mg). Fraction SCA-IV (2.4 g) afforded oleanolic acid 4 (30 mg) and ursolic acid 5 (20 mg). Fraction SCA-V (8.4 g) afforded apigenin 6 (20 mg) and β-sitosteryl glucoside 7 (35 mg).

SCB fraction (45 g) was treated in a similar manner to SCA. SCB-I (2.0 g) afforded the new compound ceratoluteolin (11 mg). Fraction SCB-II-7 (7.0 g) afforded p-hydroxyphenyl caffeate 8 (26 mg), caffeic acid 9 (16 mg), shimobashiric acid B 10 (12 mg), methyl rosmarinate 11 (161 mg), butyl rosmarinate 12 (50 mg), and luteolin 13 (12 mg). Fraction SCB-V (10 g) afforded Luteolin-7-O-glucoside 14 (28 mg) and rosmarinic acid 15 (35 mg).

2.3.1

2.3.1 Compound 1

Amorphous solid (130 mg). For 1H and 13C NMR spectral data, see Table 1. HR-ESI-MS: m/z 629.12671 [M + K] (clacd for C28H30 O14 [M + K]: 629.12671).

Table 1 1H (500 MHz), 13C (125 MHz) NMR data (δ in ppm, J in Hz), important COSY and HMBC correlations for compound 1 (in DMSO‑d6).
No δH (m, J in Hz) δC COSY HMBC
2 – 164.7 – H-6′, H-4
3 6.95 (1H, s) 104.1 – C-4
4 – 182.5 –
5 – 161.7
6 6.45 (1H, s) 99.8 H-8′ C-8, C-10
7 – 162.6 – H-1″
8 6.84 (1H, br s) 95.4 H-6′ C-9, C-1″
9 – 157.4 – H-8
10 – 106.1 – H-6
1′ – 121.7 – H-5′, H-6′
2′ 7.54 (2H, br s)* 110.9 H-6′ C-2′, C-4′
3′ – 148.6 – H-2, H-5′, H-6′, H-7′
4′ – 151.5 – H-2′, H-6′
5′ 6.96 (1H, d, J = 8.25) 116.3 H-6′ C-3′,
6′ 7.54 (2H, br s)* 121.1 H-2′, H-5′ C-2, C-1′, C-3′, C-4′
7′ 3.85 (3H, s) 56.5 – C-3′
8′ – 170.1 –
9′ 2.02 (3H, s) 21.6 – C-8′
Sugar mioety –
1″ 5.42 (1H, br d, J = 7.45) 99.3 – C-7
2″ 3.58 (2H, m) 69.5 – C-1″
3″ 71.0 – C-2″
4″ 4.29 (1H, d, J = 9.70) 75.2 – C-3″
5″ 4.92 (1H, t, J = 9.4) 76.8 – C-4″
6″ 4.05 (2H, m) 65.0 – H-2″′, C-1″′
Ester moiety –
1″′ – 168.6 – H-6″
2″′ 1.50 (2H, brt, J = 7.98) 30.4 H-3″′ H-6″, C-6″, C-3″′
3″′ 1.23 (2H, q, J = 7.22, 14.60) 18.9 H-4″′, H-2″′ H-2″′
4″′ 0.76 (3H, brt, J = 7.30) 14.0 H-3″′ H-3″′

3

3 Results and discussion

A total of fifteen compounds were isolated from the aerial parts of S. ceratophylla from Jordan. These included the new compound ceratoluteolin 1, genkwanin 4′-methyl ether 2, β-sitosterol 3, oleanolic acid 4 (Goren et al., 2002), ursolic acid 5 (Tundis et al 2002), apigenin 6 (Al-Qudah et al., 2015), β-sitosteryl glucoside 7 (Peshin and Kar, 2017), p-hydroxyphenyl caffeate 8 (Ren et al 2017), caffeic acid 9 (Ren et al 2017), shimobashiric acid B 10 (Choi et al., 2018), methyl rosmarinate 11 (Sawabe et al., 2006), butyl rosmarinate 12 (Huang et al., 1999), luteolin 13, Luteolin-7-O-glucoside 14 (Lin et al., 2015) and rosmarinic acid 15 (Al-Qudah et al., 2015). It’s worth mentioning that p-hydroxyphenyl caffeate 8 is reported here for the first time from Lamiaceae family. Additionally, compounds 2, 6, 8, 10–14 are reported here for the first time from S. ceratophylla. The structures of all isolated compounds (Fig. S1) were completely verified based on thorough investigation of their spectral data.

Ceratoluteolin 1, (Fig. 2) obtained as an amorphous solid from fraction SCB-I, is reported here for the first time from a natural source. The molecular formula of this compound was established as C28H30O14 based on its HRESIMS spectrum in the positive mode at m/z at 629.12671 (calcd for C28H30 O14 [M + K]: 629.12671). IR absorption bands at 3257, 1736 1663, 1568 and 1378 cm−1 indicated the presence of hydroxyl, carbonyl and aromatic groups, respectively. The 13C NMR spectrum of 1 (DMSO‑d6) along with each of DEPT and HMQC spectra indicated the presence of 28 carbons, 21 of which corresponded perfectly to luteolin-3′-methylether-7-O-glucoside. Aside from the carbon signals corresponding the glucoside group (δC 65.0, 69.5, 71.0, 75.2, 76.8, 99.3 for C-6″, C-2″, C-3″, C-4″, C5″, C-1″, respectively), extra two carbon signals for an acetyl groups (δC 170.1 (C-8′), 21.6 (Me-9′)) and other 4 carbon signals fitting a butyryl group (δC 14.0 (C-4″′), 18.9 (C-3″′), 30.4 (C-2″′) & 168.6 (C-1″′)) were observed. The exact location of these two groups was established based on the correlations observed in the 2D NMR experiments including COSY, HMQC and HMBC (Fig. 2). The key HMBC correlations from δH 6.84 (H-8) to δC 99.3 (anomeric, C-1″) and from δH 5.42 (anomeric H-1″) to δC 162.6 (C-7) confirmed the location of the sugar moiety at C-7. The position of the butyrate ester moiety was established based on the correlations observed from δH 4.05 (m, H-6″) to each of C-1″′ (δC 168.6) and C-2″′ (δC 30.4) in addition to the correlations between H-2″′ (δH 1.50, (2H, brt, J = 7.98)) and C-3″′ (δC 18.9). Furthermore, the COSY spectrum showed correlations between CH2-3″′ and each of H-4″′ and H-2″′. Moreover, the COSY and HMBC spectra showed correlations which confirmed the substitution pattern at ring B of the letuolein skeleton. CH-6′ showed COSY correlations with both H-2′ and H-5′. The HMBC spectrum showed that each of OCH3 protons (δH 3.85), H-5′ (δH 6.96) H-6′ (δH 7.54) were correlated to C-3′ (δC 148.6). Such correlations firmly established the location of the acetyl group at C-4′. Table 1 shows the different 1H and 13C NMR shifts (CDCl3) observed for the new compound 1.

Important COSY and HMBC correlations for compound 1.
Fig. 2
Important COSY and HMBC correlations for compound 1.

Declaration of Competing Interest

The authors declare no conflict of interest.

Acknowledgments

This work was Funded by the Dean of Scientific Research and Innovation at Al-Balqa Applied University, Al-Salt, Jordan (Grant No: 758/2017/2018) to whom the authors are especially grateful.

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Appendix A

Supplementary material

Supplementary material to this article can be found online at https://doi.org/10.1016/j.arabjc.2022.104511.

Appendix A

Supplementary material

The following are the Supplementary material to this article:

Supplementary data 1

Supplementary data 1


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