α-Glucosidase inhibitive diarylheptanoids from Ottelia acuminata var. acuminata, a traditional vegetable of Bai Nationality in Yunnan.

Diabetes is an urgent health issue characterized by ethnic and regional variations, and is inseparable from the different dietary habits. It is worthy to note that the incidence of diabetes in Bai nationality has been reported to be much lower than Han in China. As a daily vegetable of Bai, the phytochemical and antidiabetic study of Ottelia acuminata var. acuminata had not been carried out. In this study, 41 metabolites with diverse diarylheptanoid (six new ones, Otteacumienes A-F), flavone, sesquiterpenoid, coumarin, lignan, polyacetylene, and alkaloid skeletons were characterized from O. acuminata var. acuminata. Among them, the racemic nature of 3 was characterized by chiral resolution and calculated ECD methods. The biological study revealed diarylheptanoids showed significant α-glucosidase inhibitory activities with 5 as the most effective one (60-fold stronger than acarbose). Molecular docking studies indicated that these structures have different binding cavities with acarbose. This study demonstrated that O. acuminata var. acuminata might correlated with the low incidence diabetes of Bai and the diarylheptanoids may have potential therapeutic value for diabetes mellitus.

1,9-seco-Bicyclic Polyprenylated Acylphloroglucinols from Hypericum uralum.

Hyperuralones C-H (1-6), six new 1,9-seco-bicyclic polyprenylated acylphloroglucinols (1,9-seco-BPAPs) derived from the normal polyprenylated acylphloroglucinols with a bicyclo[3.3.1]nonane-2,4,9-trione core, together with six known analogues, were isolated from the aerial parts of Hypericum uralum. The structures of 1-6 were elucidated on the basis of the interpretation of NMR and MS spectroscopic data. The structure of attenuatumione B, a known compound isolated from H. attenuatum, was revised to that of a 1,9-seco-BPAP by NMR spectroscopic analysis and previous biomimetic synthesis methods. The inhibitory activities of these isolates on acetylcholinesterase were tested, and compounds 1 and 2 exhibited moderate activities with IC50 values of 9.6 and 7.1 µM, respectively.

A Triterpenoid Inhibited Hormone-Induced Adipocyte Differentiation and Alleviated Dexamethasone-Induced Insulin Resistance in 3T3-L1 adipocytes.

6α-Hydroxylup-20(29)-en-3-on-28-oic acid (1), a natural triterpenoid, was found to possess the ability in a dose-dependent manner inhibiting hormone-induced adipocyte differentiation in 3T3-L1 preadipocytes, and restoring glucose consuming ability in dexamethasone (DXM)-induced insulin resistant 3T3-L1 adipocytes. Compound 1 was also found to ameliorate DXM-induced adipocyte dysfunction in lipolysis and adipokine secretion. Mechanistic studies revealed that 1 inhibited adipocyte differentiation in 3T3-L1 preadipocytes via down-regulating hormone-stimulated gene transcription of peroxisome proliferator-activated receptor γ and CCAAT-enhancer-binding protein alpha which are key factors in lipogenesis, and restored DXM-impaired glucose consuming ability in differentiated 3T3-L1 adipocytes via repairing insulin signaling pathway and activating down-stream signaling transduction by phosphorylation of signaling molecules PI3K/p85, Akt2 and AS160, thus leading to increased translocation of glucose transporter type 4 and transportation of glucose.

Hyperuralones A and B, new acylphloroglucinol derivatives with intricately caged cores from Hypericum uralum.

Hyperuralone A (1), a polycyclic polyprenylated acylphloroglucinol possessing an unprecedented tetracyclo-[5.3.1.1(4,9).0(4,11)]-dodecane core, was characterized from Hypericum uralum together with hyperuralone B (2), a congener with another complex caged skeleton. Their structures were determined by extensive spectroscopic analysis and ECD calculations. A plausible biosynthetic pathway of their intriguing architectures via intramolecular Diels-Alder reactions was also proposed. Compound 1 exhibited obviously cytotoxic activities against five human cancer cell lines in vitro (IC50 4.6-14.4 µM).

Effects of Traditional Chinese Medicinal Plants on Anti-insulin Resistance Bioactivity of DXMS-Induced Insulin Resistant HepG2 Cells.

ABSTRACT: Medicinal plants have a long history of use in China to treat diabetic symptoms. Ancient Chinese medical manuscripts and ethnobotanical surveys document plant remedies that continue to be actively used in China for the treatment of diabetic symptoms. Based on a systematic ancient Chinese medical manuscripts review in combination with ethnobotanical survey, 16 medicinal plants for the traditional treatment of diabetic symptoms were identified for the evaluation of anti-insulin resistance bioactivity. The biological activity of 16 medicinal plants was tested on dexamethasone (DXMS)-induced insulin resistant HepG2 cells. The result shows that 11 of the 16 medicinal plants enhanced glucose uptake of DXMS-induced insulin resistant HepG2 cells, thereby demonstrating their ability to increase insulin sensitivity, other five medicinal plants including Astragalus membranaceus were found ineffective. The study shows that ancient Chinese medical manuscripts and ethnobotanical surveys on plants for the prevention and treatment of diabetic symptoms provide a promising knowledge base for drug discovery to mitigate the global diabetes epidemic.

Sterols and Terpenoids from Viburnum odoratissimum.

ABSTRACT: A new stigmasterol type natural product, viburodorol A (1), along with eleven known sterols and terpenoids (2-12), were isolated from the aerial parts of Viburnum odoratissimum. The structure of 1 was elucidated on the basis of comprehensive spectroscopic analysis. It's noteworthy that compound 2, the major constituent of this plant, can significantly stimulate glucose absorption in insulin resistant HepG2 cells without affecting cell viability. Furthermore, this compound can also restore the glucose absorption in DXMS-induced insulin resistant 3T3-L1 cells.

Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens.

ABSTRACT: Four new polycyclic polyprenylated acylphloroglucinol type metabolites, hypercohones D-G (1-4), along with four known analogues (5-8), were isolated from the aerial parts of Hypericum cohaerens. The structures of these isolates were elucidated by extensive spectroscopic methods. The inhibitory activities of these isolates against five human cancer cell lines in vitro were also tested.

Comparative homegarden medical ethnobotany of Naxi healers and farmers in Northwestern Yunnan, China.

BACKGROUND: Homegardens are ecologically and culturally important systems for cultivating medicinal plants for wellbeing by healers and farmers in Naxi communities of the Sino Himalayan region. The cultivation of medicinal plants in Naxi communities and associated ethnomedical knowledge base for maintaining and utilizing these resources is at risk with expanded commercialization of natural resources, development policies and rapid socio-economic change in China. Research is needed to understand the medicinal plant species maintained in Naxi homegardens, their use and contribution to community wellbeing, and how these practices and knowledge base varies between Naxi healers and farmers in order to develop plans for biodiversity conservation and preservation of ethnomedical practices. The main objective of this study is to document and compare medicinal plant species in Naxi homegardens and associated ethnomedical knowledge between Naxi healers and farmers. METHODS: Ethnobotanical homegarden surveys were conducted with three Naxi healers and 28 farmer households in two Naxi communities in Lijiang Prefecture in Northwest Yunnan Province of China. Surveys included inventories of medicinal plants in homegardens and semi-structured interviews with homegarden managers to document traditional medicinal uses of inventoried plants. Inventoried plants were classified into 13 'usage categories' of medical condition groupings that impact a system of the body. Finally, plant species richness was calculated for each homegarden and species richness was compared between healers and farmers as well as between study sites using a Least Square Means Tukey HSD function. RESULTS: Ethnobotanical surveys at the study sites found that 13% of households rely exclusively on traditional Naxi medicine, 26% exclusively use Western medicine and 61% use a combination of traditional Naxi and Western medicine. A total of 106 medicinal plants were inventoried in Naxi homegardens representing 50 botanical families. Over 85% of inventoried medicinal plants were herbaceous. The most represented families were Asteraceae (12.8%), Ranunculaceae (8.3%), Apiaceae (8.3%), and Polygonaceae (7.3%). The primary medical functions of inventoried plants were to treat inflammation (73 species), circulatory system disorders (62), nervous system disorders (41), detoxification (39), digestive system disorders (33), muscular-skeletal system disorders (26), genitourinary system disorders (26), skin conditions (23), respiratory systems disorders (22), and cold and flu (20). Local herbal experts maintained greater medicinal plant species richness in their homegardens compared to local farmers as well as had greater knowledge of medicinal functions of plants. Healers maintained medicinal plants primarily for healing while farmer households maintained approximately 90% of the medicinal plants in their homegardens for commercialization and the remaining for household healthcare. CONCLUSIONS: This study highlights the importance of biodiversity and traditional ecological and medical knowledge for human wellbeing and livelihoods in Naxi communities. Conservation efforts and policies are necessary to preserve the ecological and cultural base that maintains medicinal plant use by both healers and farmers in Naxi homegardens of the Sino Himalayan region.

Bioactive polyprenylated acylphloroglucinol derivatives from Hypericum cohaerens.

Nine new polyprenylated acylphloroglucinol derivatives, hypercohins B-J (1-9), and nine known analogues were isolated from the aerial parts of Hypericum cohaerens. The structures of 1-9 were elucidated based on spectroscopic analysis, and the absolute configuration of 1 was confirmed by X-ray crystallographic analysis. The inhibitory activities of these isolates on acetylcholinesterase and five human tumor cell lines were tested, and hypercohins B-D (1-3) exhibited moderate inhibitory activity (IC50 5.8-17.9 µM) against the tested tumor cell lines.