Two new neo-clerodane diterpenes in Ajuga decumbens.

Min, Zhi-Da; Mizuno, Mizuo; Wang, Shiqiang; Iinuma, Munekazu; Tanaka, Toŝhiyuki

doi:10.1248/cpb.38.3167

Cited by 27 publications

(21 citation statements)

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“…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.…”

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confidence: 99%

A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

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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...

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confidence: 99%

A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

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“…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]. Similarly, Chen et al also obtained a new compound (11) from A. decumbens [23].…”

Section: Diterpenesmentioning

confidence: 99%

“…The inhibitory activities on LPS -induced NO production of diterpenes were evaluated, compounds (22)(23)(24)(25)(26)28) showed inhibitory effects, indicating these substances were expected to be useful as effective potential anti-inflammatory agents [29,30]. Similarly, Ajugacumbin J (31) and ajugacumbin D (4) exhibited the inhibitory activities of LPS-induced NO production in RAW 264.7 macrophages with an IC 50 value of 46.2 and 35.9 mM, respectively [31].…”

Section: Anti-inflammatory Activitiesmentioning

confidence: 99%

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

Ni¹,

Dong²,

Fu³

et al. 2015

Trop. J. Pharm Res

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“…1,2) Many compounds have been isolated and identified from the whole plant, A. decumbens, [3][4][5][6][7] several of which show anti-tumor activity. 8) Recently, the number of cases of age related illnesses, e.g.…”

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Beneficial Effects of Ajuga decumbens on Osteoporosis and Arthritis

Ono¹,

Fukaya²,

Imai³

et al. 2008

Biological & Pharmaceutical Bulletin

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Ajuga decumbens is a naturally occurring herb in Japan and China. The whole flowering plant of A. decumbens has been used in treatment of hypertension, hemoptysis, carbuncles and joint pain, etc.1,2) Many compounds have been isolated and identified from the whole plant, A. decumbens, [3][4][5][6][7] several of which show anti-tumor activity. 8) Recently, the number of cases of age related illnesses, e.g. osteoporosis and osteoarthritis have been trending upwards. These illnesses seriously affect people's daily lives because bones and joints play an important role in supporting the body during everyday movement.Collagen is one of the important bone and joint composition, and decreases naturally with age. Calcium resorption is caused by this effect. It was reported that A. decumbens upregulates the synthesis of collagen in false aged model rats. 9)Accordingly, we focused on the effects of A. decumbens on bone and joint disease.Post-menopausal osteoporosis is a metabolic bone disease characterized by a decrease of bone mass after menopause. 10)Many factors contribute to the development and maintenance of skeletal mass before and after menopause. 11,12) In fact, bone mass is the end result of a dynamic and complex process called remodeling. This process is characterized by a balance between osteoclast bone resorption and osteoblast bone formation. Estrogen is one of the factors that regulates bone metabolism, therefore, estrogen depletion after menopause causes an imbalance between bone resorption and bone formation.11) In addition, it is reported that NO, synthesized by iNOS, is related to the imbalance between osteoclast bone resorption and osteoblast bone formation. [13][14][15] It is widely known that NO is involved in a diverse array of physiological processes. Furthermore, NO, especially synthesized by iNOS, is related to inflammatory diseases like osteoarthritis and rheumatoid arthritis.14,16) Based on this knowledge, we hypothesized that the inhibition or down-regulation of NO production by iNOS would provide a new form of treatment for the prevention of inflammatory bone diseases and bone metabolic disease. MATERIALS AND METHODS AnimalsEight to ten-week-old female ddY mice and eight-week-old male LEW/SsN rats were obtained from SLC (Shizuoka, Japan). The mice and rats were housed under a 12 h/12 h light/dark cycle in a temperature and humidity-controlled room. They were allowed food and water ad libitum. After a week to adapt to the lighting conditions, healthy animals were used in a variety of experiments. All experimental procedures were approved by the Committee for Ethics and Animal Experimentation, Matsuura Yakugyo Co., Ltd. Preparation of Plant ExtractsThe whole plant A. decumbens (200 g) was grown in China and a voucher specimen (HS050601) was placed in our laboratory. The dried A. decumbens was refluxed with 70% aqueous ethanol for 30 min. The alcoholic extract was then concentrated to 50 g. The concentrate was freeze-dried, finally producing 20 g (i.e., 10% yield) of a dark brown, A. decumbens extr...

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Two new neo-clerodane diterpenes in Ajuga decumbens.

Cited by 27 publications

References 0 publications

A New Phytoecdysteroid from Ajuga taiwanensis

A New Phytoecdysteroid from Ajuga taiwanensis

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

Beneficial Effects of Ajuga decumbens on Osteoporosis and Arthritis

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