Four new insect antifeedant neo-clerodane diterpenoids, ajugacumbins A, B, C and D, from Ajuga decumbens.

Min, Zhi-Da; Wang, Shiqiang; Zheng, Qi‐Tai; Wu, Binrg; Mizuno, Mizuo; Tanaka, Toŝhiyuki; Iinuma, Munekazu

doi:10.1248/cpb.37.2505

Cited by 36 publications

(25 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Plant names Phytochem Rev (2008) 7:25-49 29 Kubo (1976) ajugarin I-III A2, A5, A43 Kubo (1980) clerodin CAa1 12-bromoajugarin I (X-ray) Kubo (1982) ajugarin IV A49 Kubo (1983) ajugarin V A1 A. bracteosa (A. remota Benth.) Odek-Ogunde (1993) Min (1989) ajugacumbin A, B, D e A4, A6, A7.1 ajugacumbin C e A38.1 Min (1990) ajugacumbin E e , F A26.1, A44 ajugamarin a (AJM A1) A ajugacumbin G, A, B A3, A Amano (1997) ajugatakasin A, B A37, A32 ajugamarin A1, B1 a , G1, H1 A clerodendrin D a (= ajugapitin) CA Takasaki (1999) Malakov (1991) ajugavensin A-C CBa7, CBa8, CBa6 Malakov (1992) ajugavensin A,B (X-ray) A. iva Camps (1982) ivain…”

Section: General Introduction: the Ajuga Genus Of The Labiataementioning

confidence: 99%

neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity

Coll

Tandrón

2007

Phytochem Rev

View full text Add to dashboard Cite

The presence of several types of allelochemicals has been reported from Ajuga, a Labiatae genus comprising more than 40 species of wide distribution in extratropical regions of both hemispheres. The genus is of great medicinal and economic importance and among the biological properties of the secondary metabolites, the antifeedant activity against pest insects appears to be related to the presence of neo-clerodane type diterpenes. This review focuses on the isolation and structural elucidation of this type of compounds from Ajuga species and the hemisynthetic compounds of closely related structure obtained. The reported biological activity of crude extracts and isolated diterpenes will be briefly commented.

show abstract

Section: General Introduction: the Ajuga Genus Of The Labiataementioning

confidence: 99%

neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity

Coll

Tandrón

2007

Phytochem Rev

View full text Add to dashboard Cite

show abstract

“…4,5) Furthermore, it has also been reported that some species of this genus were especially used as diuretic agents, as a remedy for fever, toothache, dysentery and hypertension. 6) Earlier chemical investigations have led to the isolation of clerodane diterpenoids, [7][8][9] ecdysteroids, 3,5,10,11) flavonoids, 12) iridoids [13][14][15] and triglycerides. 16) The compounds isolated from the genus Ajuga, exert a broad spectrum of biological and pharmacological actions such as cytotoxic, anti-mitotic, anti-bacterial, cardiotonic, vasorelaxing, antifungal and antifeedant and insect growth-inhibitions.…”

mentioning

confidence: 99%

A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

View full text Add to dashboard Cite

Many plants contain ecdysteroids, polyhydroxysteroids with a cis-fused A/B ring junction and 14a-hydroxy-7-ene-6-one system, structurally related with ecdysone, the biosynthetic precursor of the insect moulting hormone.1) These compounds exhibit interesting physiological activities such as regulation of moulting in insects, hormonal functions involve regeneration, metamorphosis, reproduction and differentiation in all arthropods, and antiulcer, antirheumatic, insulin regulation and diuretic or tonic effects in mammals. 2)Among the numerous plants containing phytoecdysteroids, those pertaining to Ajuga genus are unique for the great variety of such compounds produced.3) Species belonging to genus Ajuga have been used as folk medicinal plants as anthelmintic against intestinal disorders, antifungal, hypoglycaemic, antitumor and antimicrobial agents. 4,5) Furthermore, it has also been reported that some species of this genus were especially used as diuretic agents, as a remedy for fever, toothache, dysentery and hypertension. 6) Earlier chemical investigations have led to the isolation of clerodane diterpenoids, 7-9) ecdysteroids, 3,5,10,11) flavonoids, 12) iridoids [13][14][15] and triglycerides.16) The compounds isolated from the genus Ajuga, exert a broad spectrum of biological and pharmacological actions such as cytotoxic, anti-mitotic, anti-bacterial, cardiotonic, vasorelaxing, antifungal and antifeedant and insect growth-inhibitions. These facts encouraged us to investigate the chemical constituents of an Ajuga species A. taiwanensis NAKAI ex MURATA (Labiatae) mainly distributed in the Taiwan, Philippines and Ryukyus which has been often used for the treatment of hepatitis and hepatoma in Taiwanese folk medicine.17) The isolation of ajugalide A to D from title plant has recently been reported from our laboratories. In this paper, we now describe the isolation and structural elucidation of one new phytoecdysteroid, ajugalide-E (1) and twenty five known compounds. Results and DiscussionAjugalide-E (1) was isolated as an optically active, white amorphous solid, mp 210-212°C. The high-resolution fastatom bombardment mass spectrum (HR-FAB-MS) of 1 showed a pseudo molecular ion peak ([MϩH] . These data were consistent with the occurrence of characteristic side chain with g-lactone by similitude with 22-acetylcasterone signals. Additional functionalities included the signal of an olefinic proton at d 6.21 (br s) as well as nine methine protons and seven methylene groups and an acetyl methyl group also supported the basic skeleton of phytoecdysteroid. As shown in Table 1 the 1 H-and 13 C-NMR spectra for compound 1 showed a high analogy with those of 22-acetylcasterone with a cis fused A/B ring junction and 14a-hydroxy-7-ene-6-one skeleton 19) Results of two-dimensional correlation spectroscopy (2D-COSY) and the long-range 13 C-1 H correlation in heteronuclear multiple bond correlation (HMBC) experiments also confirmed that the planar structure of 1 was the same as 22-acetylcasterone (2). But the differences in...

show abstract

“…Neo-clerodane diterpenes mostly show insecticidal [14,15], antibacterial [16,17], antimalarial [18], and anticancer activities [19]. In 1989, eight compounds, named Ajugacumbins A, B, C, D (1 -4), Ajugamarins A2, G1, H1 and F4 (5 -8), were isolated from the ethanol extract of A. decumbens [20,21 ]. After that, two new compounds, ajugacumbins E, F (9, 10), were isolated [22].…”

Section: Diterpenesmentioning

confidence: 99%

“…Min et al reported that these compounds (1-4, 9-10) from the ethanol extract of A. decumbens displayed growth-inhibitory properties against insects [20,22]. Similarly, compound 11 also exhibited significant insecticidal activities [23].…”

Section: Insecticidal Activitiesmentioning

confidence: 99%

Phytochemical and biological properties of <i>ajuga decumbens</i> (labiatae): A review

Ni¹,

Dong²,

Fu³

et al. 2015

Trop. J. Pharm Res

View full text Add to dashboard Cite

show abstract

Four new insect antifeedant neo-clerodane diterpenoids, ajugacumbins A, B, C and D, from Ajuga decumbens.

Cited by 36 publications

References 0 publications

neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity

neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity

A New Phytoecdysteroid from Ajuga taiwanensis

Phytochemical and biological properties of <i>ajuga decumbens</i> (labiatae): A review

Contact Info

Product

Resources

About