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Cycloolivil, a lignan from the roots of Stereospermum suaveolens.

Wahab Sab BA, Jacob J, Manjunath GG, Singh VK, Mundkinajeedu D, Shankarappa S - Pharmacognosy Res (2015 Jan-Mar)

Bottom Line: Roots of this plant are one of the ingredients of Dashamularishta.The present work deals with the isolation and identification of phytochemical constituents present in the roots of Stereospermum suaveolens.The isolated compounds structures were elucidated by analysis of spectroscopic data (UV, IR, 1D-NMR, and MS) and characterized as Cycloolivil (1) reported for the first time from this plant species, Lapachol (2) and β-sitosterol (3), respectively.

View Article: PubMed Central - PubMed

Affiliation: Pharmacognosy, Government College of Pharmacy, Natural Remedies Pvt. Ltd. Bangalore, Karnataka, India.

ABSTRACT

Background: Stereospermum suaveolens DC. (Syn. S. chelonoides) belonging to family Bignoniaceae is an important medicinal plant in India. Traditionally, it is mainly used as analgesic, liver stimulant, astringent, wound healing and antidyspeptic. Roots of this plant are one of the ingredients of Dashamularishta. The plant has been studied for many pharmacological actions, only few were concerned with isolation of active compounds.

Objective: The present work deals with the isolation and identification of phytochemical constituents present in the roots of Stereospermum suaveolens.

Material and methods: The compounds were isolated from the ethyl acetate-soluble fraction from the methanol extract of S. suaveolens by using open silica gel column chromatography and HPLC was carried out for all the fractions to target the major peaks in fractions.

Results and conclusion: The isolated compounds structures were elucidated by analysis of spectroscopic data (UV, IR, 1D-NMR, and MS) and characterized as Cycloolivil (1) reported for the first time from this plant species, Lapachol (2) and β-sitosterol (3), respectively.

No MeSH data available.


Related in: MedlinePlus

Structure of isolated Compound 1 (Cycloolivil)
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Figure 1: Structure of isolated Compound 1 (Cycloolivil)

Mentions: Compound 1 [Figure 1] shows a molecular ion peak at m/z 375.13 M-H]- consistent with molecular formula C20H24O7 (calculated 376.39316). The IR spectrum showed the bands at 1027.14 cm-1, (C-O stretch), 1261.50 cm-1 1463.07 cm-1 (aromatic C = C stretch), 2905.89 cm-1 (C-H stretch) and 3488.41 cm-1 (O-H stretch). The 1H NMR spectrum revealed the presence of two methoxy groups at δ 3.75 and δ 3.80. Two –CH2OH groups at δ 3.55 (d, J = 4.4), δ 3.81 (d, J = 2.4), δ 3.58 (d, J = 4.4) and δ 3.79 (d, J = 11.4). One naphthalene ring at δ 2.63 (d, J = 16.8), δ 3.26 (d, J = 16.8), δ 2.05 (d, J = 2.8), 4.03 (d, J = 11.6), δ 6.18 (s), δ 6.63 (s), δ 6.7 (d, J = 2.0). One benzene ring at δ 6.67 (d, J = 8.0, 2.0), δ 6.77 (d, J = 8.0) and δ 6.7 (d, J = 2.0). 13C NMR spectra of this sample further confirmed the compound by showing peak at δ 56.4 and δ 56.55 which correspond to two –OCH3 groups. The signals at δ 69.57 and 61.0 confirm the two –CH2OH groups. The signals at δ 40.08, 75.11, 47.73, 45.05, 117.5, 145.46, 147.65, 113.13, 126.59 and 133.71 confirm the presence of one naphthalene ring. The signals at δ 138.63, 114.10, 149.28, 146.26, 116.17 and 123.72 confirm the one benzene ring. Also, on the basis of spectroscopic data and previously reported literature values, compound 1 was confirmed as Cycloolivil.[13]


Cycloolivil, a lignan from the roots of Stereospermum suaveolens.

Wahab Sab BA, Jacob J, Manjunath GG, Singh VK, Mundkinajeedu D, Shankarappa S - Pharmacognosy Res (2015 Jan-Mar)

Structure of isolated Compound 1 (Cycloolivil)
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4285648&req=5

Figure 1: Structure of isolated Compound 1 (Cycloolivil)
Mentions: Compound 1 [Figure 1] shows a molecular ion peak at m/z 375.13 M-H]- consistent with molecular formula C20H24O7 (calculated 376.39316). The IR spectrum showed the bands at 1027.14 cm-1, (C-O stretch), 1261.50 cm-1 1463.07 cm-1 (aromatic C = C stretch), 2905.89 cm-1 (C-H stretch) and 3488.41 cm-1 (O-H stretch). The 1H NMR spectrum revealed the presence of two methoxy groups at δ 3.75 and δ 3.80. Two –CH2OH groups at δ 3.55 (d, J = 4.4), δ 3.81 (d, J = 2.4), δ 3.58 (d, J = 4.4) and δ 3.79 (d, J = 11.4). One naphthalene ring at δ 2.63 (d, J = 16.8), δ 3.26 (d, J = 16.8), δ 2.05 (d, J = 2.8), 4.03 (d, J = 11.6), δ 6.18 (s), δ 6.63 (s), δ 6.7 (d, J = 2.0). One benzene ring at δ 6.67 (d, J = 8.0, 2.0), δ 6.77 (d, J = 8.0) and δ 6.7 (d, J = 2.0). 13C NMR spectra of this sample further confirmed the compound by showing peak at δ 56.4 and δ 56.55 which correspond to two –OCH3 groups. The signals at δ 69.57 and 61.0 confirm the two –CH2OH groups. The signals at δ 40.08, 75.11, 47.73, 45.05, 117.5, 145.46, 147.65, 113.13, 126.59 and 133.71 confirm the presence of one naphthalene ring. The signals at δ 138.63, 114.10, 149.28, 146.26, 116.17 and 123.72 confirm the one benzene ring. Also, on the basis of spectroscopic data and previously reported literature values, compound 1 was confirmed as Cycloolivil.[13]

Bottom Line: Roots of this plant are one of the ingredients of Dashamularishta.The present work deals with the isolation and identification of phytochemical constituents present in the roots of Stereospermum suaveolens.The isolated compounds structures were elucidated by analysis of spectroscopic data (UV, IR, 1D-NMR, and MS) and characterized as Cycloolivil (1) reported for the first time from this plant species, Lapachol (2) and β-sitosterol (3), respectively.

View Article: PubMed Central - PubMed

Affiliation: Pharmacognosy, Government College of Pharmacy, Natural Remedies Pvt. Ltd. Bangalore, Karnataka, India.

ABSTRACT

Background: Stereospermum suaveolens DC. (Syn. S. chelonoides) belonging to family Bignoniaceae is an important medicinal plant in India. Traditionally, it is mainly used as analgesic, liver stimulant, astringent, wound healing and antidyspeptic. Roots of this plant are one of the ingredients of Dashamularishta. The plant has been studied for many pharmacological actions, only few were concerned with isolation of active compounds.

Objective: The present work deals with the isolation and identification of phytochemical constituents present in the roots of Stereospermum suaveolens.

Material and methods: The compounds were isolated from the ethyl acetate-soluble fraction from the methanol extract of S. suaveolens by using open silica gel column chromatography and HPLC was carried out for all the fractions to target the major peaks in fractions.

Results and conclusion: The isolated compounds structures were elucidated by analysis of spectroscopic data (UV, IR, 1D-NMR, and MS) and characterized as Cycloolivil (1) reported for the first time from this plant species, Lapachol (2) and β-sitosterol (3), respectively.

No MeSH data available.


Related in: MedlinePlus