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The continuing studies on the fruits of Stauntonia brachyanthera led to the isolations of 6 normal and nor-oleanane triterpenoids, including two new compounds, brachyantheoraside B10 (1) and brachy...

Descriptions of the cambial variants of the lianoids in two families, Lardizabalaceae and Sabiaceae, were lacking in Taiwan. This study aimed to diagnose the stem characteristics of seven lianoid species from these two families to update existing knowledge. Specifically, the transverse sections of fresh stems were diagnosed to generate a key. The results showed that all seven species develop one of ten cambial variant types, viz. axial vascular elements in segments. Of these species, Sabia swinhoei Hemsley, Stauntonia obovata Hemsley, and S. obovatifoliola Hayata formed secondary rays. The thick and successive periderm was apparent in Stauntonia obovata and S. obovatifoliola at older stem. The sclerenchyma ring was continuous or discontinuous in two genera (Akebia and Stauntonia), but was absent in Sabia. Four diagnostic features could be used to distinguish Lardizabalaceae and Sabiaceae; namely, the periderm, cortical sclerenchyma, vessel arrangement, and cortex ducts. The cambial variations documented for these seven lianoid species in Taiwan update existing information, facilitating comparisons between Lardizabalaceae and Sabiaceae.

Lutein is a carotenoid with several beneficial functions, but its poor water solubility, chemical instability, and low bioavailability limits its application. To overcome these shortcomings, self-assembly composite nanoparticles from Stauntonia brachyanthera seed albumin (SBSA), gum Arabic (GA), and carboxymethylcellulose (CMC) were developed for lutein encapsulation. Firstly, SBSA was extracted from seeds and its physicochemical properties were evaluated. Followingly, the nanoparticles were prepared with SBSA through a heat induced self-assembly method which were modified by GA and CMC. The nanoparticles exhibited good storage, pH, and salt stability. Hydrogen bonds, hydrophobic interactions, and electrostatic interactions were proved to derive the formation of nanoparticles. The maximum effective loading capacity (LC) of the lutein in nanoparticles was 0.92 ± 0.01% with an encapsulation efficiency (EE) at 83.95 ± 0.98%. Heat stability and storage stability of lutein were significantly enhanced after encapsulation into nanoparticles. In addition, the bioaccessibility of lutein increased from 17.50 ± 2.60% to 46.80 ± 4.70% after encapsulation into nanoparticles.

The analgesic studies on Stauntonia brachyanthera, a traditional Chinese folk medicine used to treat headache, pains and inflammatory diseases in local areas, showed that the EtOH extracts (EESB) and the characteristic ingredient YM11 could significantly inhibit the acetic acid-induced writhing responses by 43.1% and 78.95%, and decrease the xylene-induced ear edemas by 48.9% and 21.4%, respectively. EESB could significantly increase pain threshold of mice in hot-plate test, but the effect of YM11 was not obviously. Further study in formalin test showed the inhibitory effect of YM11 in 2nd phase was more significant than that in 1st phase, revealed the peripheral analgesic activity of YM11. The ELISA and Western Blot analysis suggested that the analgesic mechanisms of YM11 were related to the inhibitions of the expressions of TNF-α, IL-1β and IL-6, and down-regulations of Nav1.8 protein in the left side of L4–6 DRG regulated by MAPKs, in which the levels of p-ERK, p-JNK and p-p38 were all decreased. In addition, the electrophysiological experiments indicated YM11 could reduce the Nav1.8 currents by 46.01% in small-diameter DRG neurons. Therefore, the analgesic activity of S. brachyanthera might be based on the regulation of inflammatory mediators and the directly control of the sodium channel prompt.

With the aim of finding a better kidney-type glutaminase (KGA) inhibitor with potential anti-cancer properties, 18 nor-oleanane triterpenoids from Stauntonia brachyanthera, including 2 new ones, were screened against KGA. The structure-based virtual ligand screening identified 8 compounds, which might have more chance to become inhibitors of KGA with low binding energy. Glutaminase inhibition experiments and a series of cellular level assays, including cytotoxicity, wound healing, transwell invasion, western blot, and cell apoptosis, further confirmed the inhibitory effect of 5 (brachyantheraoside A8). These provided the possibility for 5 to become an inhibitor.

The seed of Stauntonia brachyanthera is usually regarded as waste after fructus processing. Here, the potential utilization value of the protein isolate (SSPI) from seeds was evaluated by investigating its physicochemical and functional properties. SSPI was a complex protein containing 7 distinct subunits that had high contents of most essential amino acids. The maximum foaming capacity of SSPI was 406.7 ± 41% at pH 9.0, and the water holding/oil adsorption capacities were 4.66 g/g and 9.06 g/g, respectively. SSPI aggregates with a particle size of 154.1 ± 5.2 nm was prepared after heat treatment, which was performed as a Pickering-like stabilizer for the structuring of water-in-oil-in-water emulsions. The outer droplet size of emulsions decreased as the aggregate concentration increased. Emulsion gels could be observed with the increasing aggregate concentration and oil fraction. Further study found that the stabilities of inner water-in-oil droplets and creaming were progressively increased by increasing the aggregate concentration during storage.

With the aim of finding more potential anti-gout compounds from natural resources, a phytochemical study on the leaves of Stauntonia brachyanthera was carried out, which led to the isolation of 11 nor-oleanane triterpenoids, including 4 new ones. Their structures were determined by the comprehensive 1D, 2D NMR, HRMS, and HPLC analysis after acid hydrolysis. Brachyantheraoside B4 (3) and 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid (8) exhibited significant inhibitory activities on xanthine oxidase with IC50 values of 0.20 and 18.5μM, respectively. Brachyantheraoside C2 (2) also showed moderate effects on XO. A primary structure-activity relationship was also summarized, which revealed the anti-gout abilities of three nor-oleanane triterpenoids and their potential possibilities as the candidate compounds for the treatment of gout. The discovery of nor-oleanane triterpenoids also widens people's idea for the study of anti-gout agents and promotes the comprehensive development of S. brachyanthera.

The studies on Stauntonia brachyanthera led to the isolations of 7 normal and nor-oleanane triterpenoids, including 2 new ones. Compounds 1 and 3 showed moderate inhibitory activity on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with the IC50 values of 16.09 and 20.19 μM, respectively, which were stronger than that of positive control. A primary structure-activity relationship was also discussed, which revealed the anti-inflammation abilities of three types triterpenoids and their potential possibilities as the candidate compounds for the treatment of inflammation.

Stauntonia brachyanthera Hand-Mazz., an evergreen shrub belonging to the family of Lardizabalaceae, is traditionally used in China to treat various diseases. Its fruit, zhuyaozi, is extremely popular in the southwest of China because of its fresh taste and abundant nutrients. The chemical study on this fruit resulted in the isolation of eight new nor-oleanane type triterpenoid saponins, brachyanthera acid A, brachyantheraoside A1–A5 and brachyantheraoside B6, B9, along with nine known compounds. Their structures were determined by extensive 1D and 2D NMR experiments along with HRESIMS analysis. Nine compounds including four new ones showed hepatoprotective activities against DL-galactosamine-induced toxicity in WB-F344 cells, with their survival rates being very close to that of bicyclol. Additionally, the results of the inhibitory study of brachyantheraoside A5 (15) on 4-MU glucuronidation indicated its less probability leading to drug–drug interaction, which revealed that brachyantheraoside A5 and its analogues might be new safe leading compounds for further investigation as hepatoprotectants.

Stauntonia brachyanthera Hand-Mazz., known as zhuyaozi or north banana by Dong Ethnicity in the southwest of China, is widely accepted as a delicious fruit with high economic value because of the presence of health-promoting components and the delivery of new tastes. In search for antioxidant compounds, the activity-guided fractionation and purification processes were performed on the stems and roots of S. brachyanthera, which resulted in the isolation of six new compounds, brachyanin A–F (1–6), and seven known compounds (7–13). Their structures were elucidated by 1D and 2D NMR, and HR-ESI-MS. Brachyanin A (1) exhibited significant cytotoxicity against HepG2 and K562 cell lines with IC50 values of 6.93 and 7.89 µM, respectively, and possessed antioxidant activity. Six compounds presented stronger antioxidant activities than those of vitamin C and quercetin in three tests (DPPH, ABTS, and FRAP). Among them, calceolarioside B (9) exhibited strongest activity and was present in higher amounts in the plant, which could be designated as characteristic component for the pharmacognostic identification and the quality control of S. brachyanthera. These findings laid solid theoretical references for the exploration of traditional usage of S. brachyanthera.

The present phytochemical investigations of Stauntonia brachyanthera Hand–Mazz resulted in the isolation of a triterpenoid glucoside (3-O- α - l -arabinopyranosyl-Akebonic acid, 1), four phenylpropanoids (staunoside C, cyclo-olivil-9-O- β - d -glucopyranoside, ficuscarpanoside B, ficuscarpanoside A, 2 – 5 ), three phenylethanoid glycosides (2-(3,4-dihydroxyphenyl)ethyl- β - d -glucopyranoside, 1′- O -phenethyl- α - l -rhamnopyranosyl-(1 → 6)- β - d -glucopyranoside, calceolarioside B, 6 – 8 ), a phenolic glycoside (seguinoside K, 9 ) and a chlorogenic acid analogue (methyl chlorogenate, 10 ). Among them, compounds 1 , 2 are isolated for the first time from this plant, compound 8 is firstly reported from genus Stauntonia and compounds 4 – 7 , 9 and 10 are new for the family of Lardizabalacea. The chemotaxonomic importance of these compounds was also summarized.

The inhibition of UDP-glucuronosyltransferases (UGTs) by herbal components might be an important reason for clinical herb-drug interaction (HDI). The inhibitory effects on UGTs via nor-oleanane triterpenoid saponins, which were the bioactive ingredients from Stauntonia brachyanthera, a traditional Chinese folk medicines with highly biological values, were evaluated comprehensively with recombinant UGT isoforms as enzyme source and a nonspecific substrate 4-methylumbelliferone (4-MU) as substrate. The results showed that there are seven compounds, 2, 3, 4, 8, 9, 13 and 14, respectively, exhibited potential inhibitions towards UGT1A1, UGT1A3 and UGT1A10 among all 23 compounds isolated from the plants. The IC50 values were 17.1μM, 13.5μM, 9.5μM, 15.7μM, 16.3μM, 1.1μM, and 0.3μM, respectively. Data fitting using Dixon and Lineweaver-Burk plots demonstrated that the inhibition of UGT1A10, UGT1A1 and UGT1A3 was best fit to noncompetitive type and competitive, respectively. The inhibition kinetic parameter (Ki) was calculated to be 39μM, 17μM, 3.3μM, 10μM, 9.3μM, 0.19μM, and 0.016μM, respectively. All these experimental data suggested that HDI might occur when compounds containing herbs were co-administered with drugs which mainly undergo UGTs-mediated metabolism.

The occurrence of more than a single species of Lardizabalaceae in Thailand is confirmed and the second species, the Vietnamese-Chinese Stauntonia chapaensis (Gagnep.) Christenh., is described and illustrated here based on the Thai specimens at Crug Farm Plants.

Stauntonia angustifolia (Wall.) Wall. ex Christenh., formerly Holboellia angustifolia Wall. is described and illustrated. Its recent history in cultivation in Cambridge is discussed.

Stauntonia brachyandra (H.N.Qin) Christenh., was collected in Vietnam in 2003, a new record for the country. This Stauntonia has the largest flowers known in the genus and was previously only known from just across the Vietnamese-Chinese border in Yunnan. It is described and illustrated here based on material from Crug Farm Plants.

Stauntonia latifolia (Wall.) Christenh. is described and illustrated here and its history of introduction is discussed. As Holboellia it was one of the first species of Stauntonia to appear in cultivation, and is currently one of the most widely grown.

Morphology. Most Lardizabalaceae are woody vines forming dense mats covering other plants, frequently climbing into the canopy of trees. Only Decaisnea are erect shrubs. Stems are usually covered in lenticels. The wood anatomy of Lardizabalaceae is unique in having very wide pith surrounded by a ring of vascular bundles, separated by wide intervascular rays. Decaisnea has long vessel elements and scalariform pitting on lateral walls and vessels with scalariform perforation plates. The vines have comparatively short and wide vessel elements with elliptic alternate pitting and vessels with simple perforation plates. Reduced short shoots are common in the East Asian taxa, but absent in the South American ones. Leaves are alternate or fasciculate on short shoots, usually palmately compound (imparipinnate in Decaisnea, biternate in Lardizabala), without stipules. Inflorescences are always axillary racemes or derived from that. Usually they emerge together with the leaves from short shoots on old growth. Typical simple racemes are found in Akebia, Lardizabala, Sinofranchetia and Stauntonia, usually with the larger female flowers at the base of the inflorescence. When the basal pedicels are elongated, corymbose racemes are formed, which are common in Stauntonia. When the racemes are branched, panicles are formed, and these are common in Decaisnea and some Japanese forms of Akebia quinata. Umbels are formed in Boquila, and through a

E-mail: yanggz888@126.comReceived July 15, 2013, Accepted December 9, 2013Key Words : Triterpenoid saponins, Lardizabalaceae, Stauntonia chinensisStauntonia chinensis DC. (Lardizabalaceae), an evergreenherb growing in southern China, commonly known as “YeMu Gua”, has been used as a traditional Chinese medicine,especially for its anti-inflammatory and analgesic effects.

The pharmacological evaluation demonstrated that the extracts from the stem ofS. brachyantheracould significantly increase the outputs of urine of rats compared to those of furosemide treated group, and the effect could last for a longer period of time. The best effect appeared in the first two hours, which scientifically confirmed the diuretic effect of the plant. The comparative pharmacognosy study showed that the characters of the crude drugs of the stem ofS. brachyantherawere similar to those ofAkebia caulis. Further systemic work on its chemical constituents by chromatographic methods and NMR elucidations led to the isolation of 10 triterpenoids, 6 flavonoids, 4 lignanoids, and 3 phenylethanoid glycosides, whose structural types were much similar to those ofA. quinata. Among them, 7 compounds were firstly reported in the genus ofStauntoniaand calceolarioside B was the common characteristic constituent in both plants. From the similar pharmacognosy characters, pharmacological effects, and chemical constituents, it could be concluded thatS. brachyantherahave a great possibility to be a succedaneum ofAkebia caulis, whose supply is extremely short in recent years.

Eleven species belonging to seven genera in the Lardizabalaceae were analyzed in terms of restriction fragment length polymorphism (RFLP) of chloroplast DNA and the sequence of the chloroplast gene,rbcL, of Lardizabalaceae and its related families. Phylogenetic trees inferred from parsimony, neighbor joining and maximum likelihood methods based on RFLP data showed that two South American genera,Boquila andLardizabala, and three East Asian genera,Akebia, Holboellia andStauntonia are closely related to each other, respectively. On the other hand, the parsimony, neighbor joining and maximum likelihood trees constructed using sequence data of therbcL gene showed thatAkebia, Stauntonia, Boquila andLardizabala clustered as(((Akebia, Stauntonia), Boquila), Lardizabala). This difference may be attributable to fewer informative sites inrbcL genes than in RFLP in this family.Decaisnea diverges at the very base of the Lardizabalaceae.

A combined data set of three genes (atpB and rbcL from the chloroplast genome and 18S nuclear ribosomal DNA) was used to assess relationships among the genera of Lardizabalaceae and to explore the relationships of the family to Sargentodoxaceae and other families in the Ranunculidae (Fumariaceae, Eupteleaceae, Circaeasteraceae, Kingdoniaceae, Berberidaceae, and Menispermaceae). Lardizabalaceae and Sargentodoxaceae together comprise a monophyletic group. Sargentodoxa, Decaisnea, and Sinofranchetia, in that order, are basal within the Lardizabalaceae sensu lato. As in previous studies based on molecular and morphological data, the ‘core’ Lardizabalaceae (Boquila, Lardizabala, Akebia, Holboellia, and Stauntonia) characterized by laminar placentation, is well-supported as a monophyletic group. A subset of this clade consisting of three Asian genera (Akebia, Holboellia, and Stauntonia) is also a well-supported monophyletic group.

Stauntonia hexaphylla (Lardizabalaceae, Japanese name mube) (Fig. 1) is widely distributed in thickets in lowlands and foothills in warmer regions of Japan, Korea and China. It is an evergreen, glabrous woody climber, whose flowers, usually unisexual, bloom pale yellow in April–May (Ohwi 1984). Stauntonia plants occur over 15 species in eastern Asia. A general outline of the lardizabalaceous family has been earlier cited (Ikuta 1991). A decoction of the stem and the root of the plant or the pericarp of the fruit is used as a diuretic in Japan and China. The fruits also activate the circulation and improve the eyesight, the barks are prepared in a compound to treat blennorrhea and to regulate menstruation (India-China) (Perry and Metzger 1980). From defatted powdered seeds of S. hexaphylla extd. (1.1 kg), three acidic triterpene glycosides mubenins A (7.2 g), B (7.9 g), and C (5.2 g) containing oleanolic acid for A and B, and hederagenin for C as the sapogenins were isolated and determined (Takemoto and Kametani 1965). (Fig. 2). Furthermore, six triterpene saponins (Yemuoside YM 7, 8, 9, 11, 13, and 14) and two lignan glycosides (YM 2 and 6) have been reported from S. chinensis DCNE grown in South China. This plant has been used as a traditional medicine in China especially for analgesic and sedative purposes (Wang et al. 1989a, b, 1990). Earlier six triterpenes, two sterols and four saponins containing eight new compounds were reported from the callus tissues of the lardizabalaceous plant Akebia quinata (Ikuta and Itokawa 1986, 1988, 1989a, Ikuta 1991).

The lardizabalaceous family occurs in central (the Himalayas) to eastern Asia (Japan), and in Chile, and there are eight genera [Decaisnea (India, China), Sinofranchetia (China), Holboellia (E. Asia), A kebia (E. Asia), Parvatia (E. Himal.), Boquila (Chile), Stauntonia (E. Asia), and Lardizabala (Chile)]. About 38 species are recorded (Huchinson 1973). The plants are woody vines or sometimes shrubs. Leaves are palmate or rarely pinnate alternate. Flowers are usually unisexual. Ovules are usually many, and fruit berrylike, dehiscing lengthwise. Some genera are cultivated in the United States, where A kebia is more common (Decaisnea, Lardizabala, Stauntonia, and rarely Sargentadoxa along the southern border of the United States) (Benson 1979). Futhermore, some few species are found in East Asia and three species in Japan, i.e., A kebia quinata Decne (Akebi in Japanese), A. triforiata Koidz (Mitubaakebi in Japanese), and Stauntonia hexaphylla Decne (Mube in Japanese). A. quinata (Fig. 1) is widely distributed in thickets in hills and mountains in Japan, Korea, and China. It is a glabrous climber with woody vines or sometimes shrubs, with plants reaching to more than 3 m high, whose flowers, usually unisexual, bloom pale purple in April-May. The ovules are usually many and the fruit is 5–8 cm long, oblong and is a fleshy follicle, bacciform, dehiscing lengthwise. It becomes dark purplish, and when mature in September-October, the seeds are black (Ohwi 1984). Its air-dried stems are used as a crude drug (Mokutsu in Japanese) in Japan and China, for example as an antiphlogistic, diuretic, and analgesic.

Optically active monoacetyldiacylglycerols were isolated from the Stauntonia hexaphylla seed oil. The hydrogenated Stauntonia monoacetyldiacylglycerols gave a plain, negative optical rotatory dispersion curve. Comparison of the triacylglycerols with those of known configuration in the optical rotatory behavior showed that all Stauntonia monoacetyldiacylglycerols were essentially (S) -3-acetyl-1, 2-diacylglycerol. The constituent acids, other than acetic, of the triacylglycerols were ordinary long-chain fatty acids. Octadecenoic and octadecadienoic acids were present in abundance in the 2-position.