Two New Diterpenoids from Ballota limbata

Ahmad, Viqar Uddin; Farooq, Umar; Hussain, Javid; Ullah, Farman; Nawaz, Syed Junaid; Choudhary, M. Iqbal

doi:10.1248/cpb.52.441

Cited by 28 publications

(24 citation statements)

References 17 publications

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“…The genus Otostegia (Lamiaceae) consists of about 33 species growing mainly in the Mediterranean region and adjoining Asia Minor (Ahmad et al, 2004). O. persica locally called "Golder" is widely distributed in south and south eastern of Iran.…”

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Anticonvulsant Activity of Otostegia persica (Burm.) Boiss

Ansari¹,

Shafaroodi²,

Asgarpanah³

2014

Biosci., Biotechnol. Res. Asia

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Investigation of the anticonvulsant activity Otostegia persica. The anticonvulsant activity of O. persica total extract was assessed in pentylenetetrazole (PTZ)-induced convulsion in mice, with Diazepam as standard drug. While mechanistic studies were conducted using flumazenil, a GABAA-benzodiazepine receptorcomplex site antagonist. the extractproduced protectionagainst convulsion at800mg/kg, compared with protection with benzodiazepine.The mean onset and percentage protection against convulsion in extract-treated mice werereduced by flumazenil. These results suggest that O. pesica extractpossesses biologically active constituent(s) that haveanticonvulsant activity which supports the ethnomedicinal claims of the use of the plant in the management of seizure.

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confidence: 99%

Anticonvulsant Activity of Otostegia persica (Burm.) Boiss

Ansari¹,

Shafaroodi²,

Asgarpanah³

2014

Biosci., Biotechnol. Res. Asia

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“…In agreement with this hypothesis, the UV spectrum of 1 showed multiple absorptions at l max 315, 308, 290, and 275 nm which were attributed to furan ring and a,b-unsaturated carbonyl group. In 1 H-NMR spectrum of 1 only two downfield methyl singlets were observed which were unusual for clerodanes previously isolated from Otostegia limbata, 6,7) whereas 13 C-NMR spectra showed several low field carbons, again unusual for the said class of diterpenoids. Apart from UV and IR spectra, the presence of furan was also confirmed from the methine signals in 1 …”

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confidence: 79%

Two New Rare-Class Tetracyclic Diterpenoids from Otostegia limbata

Farooq

Khan

Ahmad

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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The genus Otostegia (Lamiaceae) comprises ca. 33 species, mainly occurring in the Mediterranean region.2) In Pakistan, only two species have been found, namely Otostegia aucheri BOISS. and Otostegia limbata (BTH.) BOISS. (Syn. Ballota limbata BTH.; Labiatae). Otostegia limbata is locally called "Bui" or "Phut kandu."3) It is widely distributed in the North-West Frontier Province and lower hills of West Punjab in Pakistan. The species of genus Otostegia are widely used by the traditional practitioners against various diseases, and their constituents have shown to possess anti-ulcer, antispasmodic, antidepressant, anxiolytic and sedative activities. 4)Traditionally, O. limbata has been used in the treatment of children gum diseases and for ophthalmia in man.5) Here, we report the isolation and structure elucidation of two new rareclass tetracyclic diterpenoids ( Fig. 1) from O. limbata. Results and DiscussionThe CHCl 3 extract of the air-dried whole plant of Otostegia limbata was subjected to silica gel chromatotogarphy to give two new rare-class tetracyclic diterpenoids provisionally named as limbatenolide D (1) and limbatenolide E (2).Compound 1 was isolated as a gummy solid from moderately polar fraction eluted with CHCl 3 . The molecular ion peak of compound 1 at m/z 326 both in FD-MS and HR-EI-MS spectra combined with 22 hydrogen and 20 carbon signals seen in the 1 H-and 13 C-NMR spectra led to the molecular formula C 20 H 22 O 4 consistent with ten degrees of unsaturation. The basic skeleton of compound 1 was identified on the basis of its 1 H-, 13 C-NMR, and characteristic IR data.6) The IR spectrum showed an absorption band for furan ring at 865 cm Ϫ1, whereas a strong carbonyl absorption at 1620 cm Ϫ1 was attributed to an a,b-unsaturated ketone which was also conjugated to the furan ring; five-membered lactone absorption appeared at 1760 cm Ϫ1. In agreement with this hypothesis, the UV spectrum of 1 showed multiple absorptions at l max 315, 308, 290, and 275 nm which were attributed to furan ring and a,b-unsaturated carbonyl group. In 1 H-NMR spectrum of 1 only two downfield methyl singlets were observed which were unusual for clerodanes previously isolated from Otostegia limbata, 6,7) whereas 13 C-NMR spectra showed several low field carbons, again unusual for the said class of diterpenoids. Apart from UV and IR spectra, the presence of furan was also confirmed from the methine signals in 1 H-NMR at d (Fig. 2) that the furan ring was fused with the tetracyclic clerodane skeleton as the peak at d H 6.40 (H-14) showed cross peaks with downfield olefinic quaternary carbons C-13 (d C 135.9), C-16 (d C 150.6), and methylene car- Karachi-75270, Pakistan. Received October 9, 2006; accepted December 21, 2006 Two new tetracyclic diterpenoids trivially named as limbatenolide D (1) and limbatenolide E (2) have been isolated from Otostegia limbata. The structure elucidation of the compounds was based primarily on two-dimensional (2D) NMR techniques and on comparison with the literature data. Two New Rare-Clas...

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“…The chemical shift of an upfield OCH 3 was observed at δ 56.2 and a downfield C-15 signal at δ 100.9. In the 13 Cspectrum (Table 1) [4]. NOE ( Figure 1B) established correlation between H-19, H-5 and H-6, and were disposed cis to each other, while H-20 did not show connectivity with any of the above groups confirming the trans stereochemistry at the ring junction.…”

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confidence: 86%

“…The compounds are useful for skin, hair, nail, and are particularly useful to enhance the skin protective functions. Previously we have isolated diterpenoids from B. limbata, some of which have shown enzyme inhibition activities [2,3]. As part of our ongoing chemical studies on B. limbata, two new compounds provisionally named as ballonigrin lactone A and B (1 and 2) have been isolated from the roots.…”

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confidence: 99%

“…Its molecular formula, C 21 H 26 O 6 , was established by HR-EI-MS, which showed the [M] + peak at m/z 374.1727. The peaks at m/z 141, 140, and 127 suggested the presence of a methoxy substituted lactone ring with an alkyl chain [4], while the ion peaks at m/z 219, 202, and 174 showed the presence of a diterpenoid skeleton [5]. Other important peaks at m/z 356 [M-H 2 O], 346 [M-CO], and 330 [M-CO 2 ], typical for a diterpenoid skeleton, were also observed.…”

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confidence: 99%

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