The heartwood of Pterocarpus marsupium is called as “Asana” in Ayurveda. Its aquatic infusion was used for treating “prameha,” which indicates a polyuria disease in modern medicine. In our research program to investigate a novel agent to improve hyperuricemia, we focused on the extract of Asana as a xanthine oxidase (XOD) inhibitor. Asana extract (50% ethanolic extract, PM-ext) showed 11%, 35%, and 38% inhibition at 50, 200, and 500 µg/mL, respectively. Subsequently, PM-ext was partitioned with ethyl acetate (AcOEt), butanol, and water. Among them, AcOEt-soluble fraction indicated the most potent XOD inhibitory activity and was consecutively fractionated using various liquid chromatography to obtain liquiritigenin (1), isoliquiritigenin (2), and marsupsin (3) as active principles. Compound 1 showed 16% inhibition at 200 µM while 2 showed 20%, 32%, and 46% inhibition at 50, 100, and 200 µM, respectively. Compound 3 showed 15% inhibition at 500 µM. This is the first report on the XOD inhibitory activity of 3. From these results, PM-ext is a promising candidate material for improvement of hyperuricemia. Here, Asana was recognized as an effective material against noncommunicable disease and is expected to be developed as a functional ingredient.

Skeletal muscle plays a critical role in locomotion and energy metabolism. Maintenance or enhancement of skeletal muscle mass contributes to the improvement of mobility and prevents the development of metabolic diseases. The extracts from Kaempferia parviflora rhizomes contain at least ten methoxyflavone derivatives that exhibit enhancing effects on ATP production and glucose uptake in skeletal muscle cells. In the present study, we investigated the effects of ten K. parviflora-derived methoxyflavone derivatives (six 5,7-dimethoxyflavone (DMF) derivatives and four 5-hydroxy-7-methoxyflavone (HMF) derivatives) on skeletal muscle hypertrophy. Murine C2C12 myotubes and senescence-accelerated mouse-prone 1 (SAMP1) mice treated with methoxyflavones were used as experimental models to determine the effects of HMF derivatives on myotube diameter and size and muscle mass. The four HMF derivatives, but not the six DMF derivatives, increased myotube diameter. The 5-hydroxyflavone, 7-methoxyflavone, and 5,7-dihydroxyflavone had no influence on myotube size, a result that differed from HMF. Dietary administration of the mixture composed of the four HMF derivatives resulted in increase in the soleus muscle size and mass in SAMP1 mice. HMF derivatives also promoted protein synthesis in myotubes, and treatment with the intracellular Ca2+ chelator BAPTA-AM, which depletes intracellular Ca2+ levels, inhibited this promotion. Furthermore, BAPTA-AM inhibited HMF-promoted protein synthesis even when myotubes were incubated in Ca2+-free medium. These results indicate that HMF derivatives induce myotube hypertrophy and that both the 5-hydroxyl group and the 7-methoxy group in the flavones are necessary for myotube hypertrophy. Furthermore, these results suggest that HMF-induced protein synthesis requires intracellular Ca2+, but not extracellular Ca2+.

In our research program to investigate novel agents for anti-malodor activity from natural plant resources, we focused on Pterocarpus marsupium, which has been used as a “toothbrush tree” in Asian countries for many years. A 50% ethanol extract (PM-ext) was prepared and tested for anti-methioninase and anti-collagenase activity along with suppressive activity against matrix metalloprotease (MMP)-1 from interleukin-1β stimulated human gingival fibroblast. PM-ext showed moderate anti-methioninase and anti-collagenase activity as 35 and 33% at 500 μg/mL, while PM-ext showed suppression of MMP-1 release at 10 μg/mL. The active principles of MMP-1 release suppression were revealed as pterostilbene, (+)-liquiritigenin, isoliquiritigenin and α- epi-coatline A. Among them, pterostilbene showed suppression at 0.5 μM, which was the most potent of the four compounds.

黒ショウガ(Kaempferia parviflora) はタイで古来民間薬として様々な疾患に対して利用されている.この黒ショウガからメトキシフラボン類が同定され,機能性について報告されているものもある.黒ショウガの80 %エタノール抽出物から,6種類のメトキシフラボン;5,7,3',4'-tetramethoxyflavone, 3,5,7,3', 4'-pentamethoxyflavone, 5,7-dimethoxyflavone, 5,7,4'-trimethoxyflavone, 3,5,7-trimethoxyflavone, 3,5,7,4'-tetramethoxyflavoneの含有を確認した.この6種類のメトキシフラボン混合物の安全性を検討するために,マウスを用いた28日間反復経口投与試験を実施した.その結果,この反復経口投与試験においては体重変化,血液学検査,臓器重量測定,血液生化学検査では被験物質投与による有意な毒性は示されなかった.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

The decoction from a tumbler made of heartwood of the Indian kino tree (Asana, Pterocarpus marsupium, PM) was a remedy for diabetes mellitus in Ayurveda. Diabetes mellitus is a one of the lifestyle-related diseases that finally leads to the induction of fatal diseases such as arterial sclerosis and cerebral infarction. In this study, effects on blood fluidity was investigated using extract obtained from the heartwood of PM. Oral administration of the extract reduced passage time of the blood obtained from disseminated intravascular coagulation model rats. In addition, the extract inhibited the reduction of platelets, which suggests that this attributed to the inhibition of platelet aggregation. The extract also demonstrated suppressive effects on both collagen- and arachidonic acid-induced platelet aggregation. Moreover, the extract showed inhibition against cyclooxygenase. The active principle was determined to be pterostilbene by collagen-induced platelet aggregation inhibitory activity-guided purification. Pterostilbene is a derivative of resveratrol, which is known to be in red wine and to possess beneficial effects for prevention of life-style related diseases. Pterostilbene exhibited 56 and 57% inhibition on both collagen- and arachidonic acid-induced platelet aggregation at 20 μM, respectively. These results demonstrate that the extract of PM heartwood may be a promising candidate as a multifunctional agent for treating lifestyle-related diseases.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Improvement in blood fluidity leads to the prevention of various lifestyle-related diseases. A raw material for improving blood fluidity has been long desired in the research area of functional and supplemental foods. We successfully showed an improvement in blood fluidity by the Zingiberaceae plant, Kaempferia parviflora . The rhizome of the plant reduced the blood passage time through a micro slit using a disseminated intravascular coagulation model. The mechanism was attributed to the activation of fibrinolysis, as demonstrated by elongation of the euglobulin lysis time and an in-vitro fibrinolysis assay. The active principles were determined to be methoxyflavones. The results show that the rhizome of K. parviflora is a promising candidate preventive agent for treating lifestyle-related diseases.

Kaempferia parviflora (KP), a Zingiberaceae plant, is used as a folk medicine in Thailand for the treatment of various symptoms, including general pains, colic gastrointestinal disorders, and male impotence. In this study, the inhibitory activities of KP against xanthine oxidase (XOD) were investigated. The extract of KP rhizomes showed more potent inhibitory activity (38% at 500 µg/ml) than those of the other Zingiberaceae plants tested. Ten methoxyflavones were isolated from the KP extract as the major chemical components and their chemical structures were elucidated by X-ray crystallography. The structurally confirmed methoxyflavones were subjected to the XOD inhibitory test. Among them, 3,5,7,4',5'-pentamethoxyflavone and 3',4',5,7-tetramethoxyflavone showed inhibitory activities (IC(50) of 0.9 and >4 mM, respectively) and their modes of inhibition are clarified as competitive/non-competitive mixed type. To the best of our knowledge, this is the first report to present the inhibitory activities of KP, 3,5,7,4',5'-pentamethoxyflavone and 3',4',5,7-tetramethoxyflavone against XOD.