Nepetanal and nepetanoate: a new diterpene aldehyde and a benzene derivative ester from <i>Nepeta juncea</i>

Hussain, Javid; Jamila, Nargis; Khan, Farman Ullah; Devkota, Krishna Prasad; Shah, Mohammad Raza; Anwar, Saeed

doi:10.1002/mrc.2439

Cited by 8 publications

(7 citation statements)

References 10 publications

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“…Another flavone frequently present in Nepeta species is 8‐hydroxycirsimaritin, detected in 30 species (Jamzad et al , ). Several studies reported the presence of the triterpenoids ursolic acid and oleanolic acid among the major components of Nepeta species (Kökdil et al , ; Taviano et al , ; Güvenalp et al , ; Hussain et al , ; Bisht et al , ). The iridoid nepetanudoside B was previously isolated from the aerial parts of Nepeta nuda ssp.…”

Section: Resultsmentioning

confidence: 99%

Angiotensin‐Converting Enzyme Inhibitory Activity and Antioxidant Properties of Nepeta crassifolia Boiss & Buhse and Nepeta binaludensis Jamzad

Tundis

Nadjafi

Menichini

2012

Phytotherapy Research

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This article reports phytochemical and biological studies on Nepeta binaludensis and Nepeta crassifolia. Both species were investigated for their angiotensin-converting enzyme (ACE) inhibitory activity and antioxidant properties through three in vitro models [2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) and ferric reducing antioxidant power (FRAP) assay]. Aerial parts were extracted with methanol and partitioned between water and subsequently n-hexane, ethyl acetate and n-butanol. N. binaludensis methanol extract exerted significantly higher reducing power (1.9 μM Fe(II)/g) than did the positive control butylhydroxytoluene (63.2 μM Fe(II)/g) in FRAP assay. The highest DPPH radical scavenging activity was found for N. crassifolia, with IC50 values of 9.6 and 12.1 µg/mL for ethyl acetate and n-butanol fractions, respectively. n-Butanol fraction of both species showed the highest ACE inhibitory activity, with IC50 values of 59.3 and 81.7 µg/mL for N. binaludensis and N. crassifolia, respectively. Phytochemical investigations resulted in the isolation of ursolic acid, oleanolic acid, apigenin, luteolin and ixoroside. Apigenin-7-O-glucoside, 8-hydroxycirsimaritin and cirsimaritin were furthermore identified in N. crassifolia ethyl acetate-soluble fraction. Nepetanudoside B was isolated from the n-butanol fraction of N. binaludensis.

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Section: Resultsmentioning

confidence: 99%

Angiotensin‐Converting Enzyme Inhibitory Activity and Antioxidant Properties of Nepeta crassifolia Boiss & Buhse and Nepeta binaludensis Jamzad

Tundis

Nadjafi

Menichini

2012

Phytotherapy Research

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“…170,171 Compounds 423 and 428 both contain a 18-aldehyde and the same relative stereochemistry, but the former was reported as a neo -clerodane from Teucrium massiliense and the latter as an ent - neo -clerodane from Nepeta juncea . 111,172 …”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

“…However, the boriented epoxide of phlomeoic acid (376) from Phlomis bracteosa is uniquely at C-1/C-10. 89,111,142,151,165,[170][171][172] (Table 12 compounds 420-428 found in ESI †). Crolechinic acid ( 422) is representative of type II subtype IIb compounds and was found as a minor constituent in Croton lechleri based on TLC proles and NMR spectra.…”

Section: Type I With An Acyclic Side Chain At C-9mentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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“…The HMBC (Scheme-I) of 1 revealed that the α-oriented CH 3 -19 at δ H 1.20 was correlated to the carbon atoms at δ C 28.3 (C-4), 75.4 (C-6) and 32.2 (C-10), which established the presence of aldehyde moiety at C-4 15,16 . The signal in 1 The comparative stereochemistry of 1 was decided by judgment of the spectral data of 1 with those documented for other known diterpenoids 17 as well as from its NOESY spectrum (Scheme-II). The CH3-19 displayed NOE relationship with H-1, H-3, H-4 and H-20, whereas CH3-17 also demonstrated correlation with H-12 and H-20.…”

Section: Resultsmentioning

confidence: 99%

Asperal: A New Clerodane Diterpene from Sonchus asper

Khan¹,

Khan²,

Hussain³

et al. 2014

Asian J. Chem.

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Sonchus asper (L.) Hill belongs to family Asteraceae andlocally named as Mahtari used in the treatment of liver injuries 1 , protease inhibition and in the prevention of squamous cellcarcinoma of esophagus 2 as well as in human colorectal cancer 3 . This herb has also been credited in a variety of human disorder including wounds and burns 4 cough, bronchitis and asthma 5 , gastrointestinal infection, inflammation, diabetes and cardiac dysfunction 6 , kidney and liver disorders 7 , reproductive disorder like impotence (erectile dysfunction) in humans 8 , jaundice 9 and cancer 3 . Besides its pharmacological behavior, S. asper also contains secondary metabolites like flavonoids 10 , terpenes and glycosides 11 . EXPERIMENTALThe plant Sonchus asper was collected at Parachinar Kurram Agency, Khyber Pukhtunkhwa (N.W.F.P) Pakistan, in July, 2009 and was identified by a plant taxonomist. As the field from where the plant has been collected was open, no authority was responsible to issue permission and the study did not involve endangered and protected species. Likewise there was no restriction from land owner on usability of this specie and the permission was given from the land owner for

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Nepetanal and nepetanoate: a new diterpene aldehyde and a benzene derivative ester from Nepeta juncea

Cited by 8 publications

References 10 publications

Angiotensin‐Converting Enzyme Inhibitory Activity and Antioxidant Properties of Nepeta crassifolia Boiss & Buhse and Nepeta binaludensis Jamzad

Angiotensin‐Converting Enzyme Inhibitory Activity and Antioxidant Properties of Nepeta crassifolia Boiss & Buhse and Nepeta binaludensis Jamzad

Clerodane diterpenes: sources, structures, and biological activities

Asperal: A New Clerodane Diterpene from Sonchus asper

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