A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies.

The genus Maytenus is a member of the Celastraceae family, of which several species have long been used in traditional medicine. Between 1976 and 2021, nearly 270 new compounds have been isolated and elucidated from the genus Maytenus. Among these, maytansine and its homologues are extremely rare in nature. Owing to its unique skeleton and remarkable bioactivities, maytansine has attracted many synthetic endeavors in order to construct its core structure. In this paper, the current status of the past 45 years of research on Maytenus, with respect to its chemical and biological activities are discussed. The chemical research includes its structural classification into triterpenoids, sesquiterpenes and alkaloids, along with several chemical synthesis methods of maytansine or maytansine fragments. The biological activity research includes activities, such as anti-tumor, anti-bacterial and anti-inflammatory activities, as well as HIV inhibition, which can provide a theoretical basis for the better development and utilization of the Maytenus.

New Cassane Diterpenoids from Caesalpinia sappan and their Antiplasmodial Activity.

One new cassane diterpene possessing an unusual N bridge between C-19 and C-20 named caesalsappanin R (1), as well as another new diterpene caesalsappanin S (2), were isolated from the seeds of Caesalpinia sappanwith methanol extract. Their structures were determined by spectroscopic analysis and examined alongside existing data from prior studies. Their biological activities were profiled by their antiplasmodial activity.

[A new triterpenic acid from the roots of Rosa laevigata].

This study was designed to investigate triterpenoids from the roots of Rosa laevigata Michx. The silica gel column chromatography was used to separate the chemical constituents from the roots of Rosa laevigata Michx. HPLC was used to analyze its purity and chemical constitution. Spectroscopy methods were used to determine their structures. Five constituents were isolated and identified as19α-OH-3ß-E-feruloyl corosolic acid (1), 23-hydroxy-tormentic acid (2), 2α, 3ß, 19α, 23- tetrahydroxy-12-en-28-oleanolic acid (3), 2α, 3α, 20ß- trihydroxyurs-13 (18)-en-28-oic-acid (4), 2α, 3ß, 20ß-trihydroxyurs-13 (18)-en-28-oic-acid (5). Compound 1 was assigned as a new compound, compounds 4, 5 were obtained from the genus Rosa for the first time.

[Triterpenoids from roots of Rosa laevigata].

To study the triterpenoids from the roots of Rosa laevigata. The silica gel column chromatography was used to separate the chemical constituents from the roots of Rosa laevigata Michx. HPLC was used to analyze its purity, chemical and spectroscopy methods were used to determine their structures. 12 constituents were isolated and identified as(2R, 19R)methyl 2-acetyloxy-19- hydroxyl-3-oxo-urs-12-en-28-carboxylate(1), pomonic acid (2), 18, 19-seco, 2α, 3α-dihydroxy-19-oxo-urs-11, 13(18)-dien-28-oic acid(3), swinhoeic acid (4), myrianthic acid(5), 2α, 3ß, 19α-trihydroxy-24-oxo-urs-12-en-oic acid (6), tormentic acid(7), arjunic acid (8), 1ß-hydroxyeuscaphic acid(9), quadranoside Ⅷ (10), alpinoside(11), rubuside B (12). Compounds 1-4, 6, 9, 11-12 were obtained from this plant for the first time. Compounds 2-4, 6, 11-12 were obtained from the genus Rosa for the first time.

[Cassae-type diterpenes from seeds of Caesalpinia minax].

Fifteen cassaen-type diterpenes were isolated from the 95% ethanolic extract of the seeds of C. minax through various chromatographic techniques. Their structures were identified on the basis of spectroscopic data as pulcherralpin (1), caesalpinin ML (2), chamaetexane C (3), chamaetexane D (4), 6ß, 18-diacetoxycassan-13, 15-diene (5), neocaesalpin K (6), neocaesalpin MP (7), neocaesalpin M (8), neocaesalpin Q (9), neocaesalpin P (10), neocaesalpin R (11), caesaldekarin D (12), caesaldekarin A (13), caesaldekarin b (14), 3ß,6α-diacetoxyvouacapane (15). Among them, compounds 14, 9-11 were isolated from this plant for the first time.

A new ursane-type triterpene, cymosic acid from Rosa cymosa.

A new ursane-type triterpene, cymosic acid (1) together with two known compounds, 3ß,19α-dihydroxy-2-oxo-12-ursen-28-oic acid (2) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (3), were isolated from Rosa cymosa Tratt. The structure of compound 1 was elucidated by analyzing its ¹H and ¹³C NMR, ¹H-¹H COSY, HSQC, HMBC, NOESY, and HR-ESI-MS values. The three compounds were found to display moderate inhibitory activities against nitric oxide production in lipopolysaccharide-activated macrophage cell lines, RAW 264.7 cells.

Two new degradative cassane-type diterpenes isolated from Caesalpinia minax.

Cassane-type diterpenes are main bioactive constituents of Caesalpinia minax HANCE. As a part of our ongoing chemical investigation of C. minax, two new degradative cassane-type diterpenes, named caesalpins I (1) and J (2), were isolated from the EtOAc extract of the seeds of C. minax. The structures were elucidated by means of spectroscopic analysis.

[Triterpene constituents from Rosa cymosa Tratt].

The constituents in 95% ethanol extract of the root of Rosa cymosa Tratt were purified by column chromatography techniques, leading to isolation of eleven triterpenes. Their structures were elucidated by spectroscopic data as pomolic acid (1), fupenzic acid (2), ursolic acid (3), euscaphic acid (4), arjunic acid (5), tomentic acid (6), 3ß-E-feruloyl corosolic acid (7), 1ß-hydroxyeuscaphic acid (8), myrianthic acid (9), cecropiacic acid (10), and ilexoside B (11). Among them, compounds 3, 6-8, 10 and 11 were obtained from this plant for the first time, and compounds 7 and 10 were obtained from this genus for the first time.

Cytotoxic constituents from Psoralea corylifolia.

Bioassay directed isolation of the EtOAc extract from a traditional Chinese medicine Psoralea corylifolia resulted in the purification of two isoflavonoids, corylifols D (1) and E (2), along with four known ones. The structures of 1 and 2 were determined by extensive 1D and 2D NMR and MS data analyses. When tested against HepG2 and Hep3B hepatocellular carcinoma cell lines, corylifol A (4) displayed IC50 values of 4.6 and 13.5 µg/ml, respectively.

[Chemical constituents from the twigs and leaves of Melodinus suaveolens].

OBJECTIVE: To investigate the chemical constituents from the twigs and leaves of Melodinus suaveolens. METHODS: The chemical consituents were separated and purified by column chromatographies with silica gel, Sephadex LH-20, ODS and RP-HPLC. Their structures were identified on the basis of physicochemical properties and spectral analysis. RESULTS: Ten compounds were isolated and identified as ursolic acid (1), 22alpha-hydroxyursolic acid (2), betulinic acid (3), betulinic alcohol (4), 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl) -propan-1-one (5), (+)-isolariciresinol (6), (+/-)-liquiritigenin (7), salicylic acid (8), beta-sitosterol (9) and daucosterol (10), respectively. CONCLUSION: NMR spectra of compound 2 are reported for the first time, and compounds 1 - 10 are firstly isolated from this plant.

Cassane-type diterpenes from the seeds of Caesalpinia minax with their antineoplastic activity.

Five new cassane-type diterpenes, neocaesalpin AA (1), neocaesalpin AB (2), neocaesalpin AC (3), neocaesalpin AD (4) and neocaesalpin AE (5), were isolated from Caesalpinia minax together with three known compounds, 12α-methoxyl,5α,14ß-dihydroxy-1α,6α,7ß-triacetoxycass-13(15)-en-16,12-olide (6), spirocaesalmin (7) and magnicaesalpin (8). Their structures were elucidated based on 1D and 2D NMR, MS and CD analyses. Compounds 1-6 were tested against Hela, HCT-8, HepG-2, MCF-7 and A549 cancer cells and showed moderate cytotoxicity with IC50 values from 18.4 to 83.9 µM.

The new cassane-type diterpenes from Caesalpinia minax.

Four new cassane-type diterpenes, Neocaesalpin S (1), Neocaesalpin T (2), Neocaesalpin U (3), and Neocaesalpin V (4) were isolated from Caesalpinia minax HANCE together with seven known compounds Neocaesalpin A (5), Neocaesalpin K (6), Neocaesalpin L (7), Neocaesalpin M (8), Neocaesalpin O (9), Neocaesalpin MP (10), and Magnicaesalpin (11). Their structures were elucidated on the basis of 1D- and 2D-NMR, MS, and circular dichroism (CD) analysis. Compounds 1-4 were tested against liver cancer (HepG-2) and breast cancer (MCF-7), and showed mild antiproliferative activity.

Two new diterpenes, neocaesalpin MR and minaxin C, from Caesalpinia minax.

Two new cassane-type diterpenes, neocaesalpin MR and minaxin C, were isolated from Caesalpinia minax HANCE. The structures of these compounds were elucidated by means of spectroscopic analysis. Among these isolated compounds, neocaesalpin MR showed mild activities toward HeLa and colon cancer (HCT-8) human cancer cell lines.

Traditional uses, phytochemical, pharmacology, quality control and modern applications of two important Chinese medicines from Rosa laevigata Michx.: A review.

Rosa laevigata Michx. is an ethnic medicine that have strong biological activities used in the traditional medicine system for the treatment of diabetes, nephropathy, myocardial damage, oxidative damage, liver damage and so on. Currently, The Chinese herb R. laevigata Michx. can be divided into two important medicines: Fructus R. laevigata and Radix R. laevigata, from which approximately 148 chemical components have been isolated, including flavonoids, lignans, polyphenols, steroids, triterpenoids, tannins as well as other components. Pharmacological studies have already confirmed that both of these herbs have antioxidant, anti-inflammatory, antiviral and anti-tumor activities, as well as renal protective, immunomodulatory, lipid-lowering, cardiovascular protective, bacteriostatic, and other pharmacological effects. Toxicological tests and quality control studies revealed the safety and nontoxicity of R. laevigata Michx. Therefore, this paper systematically summarizes the traditional uses, botanical, phytochemical, and pharmacology as well as the quality control and toxicology of Fructus and Radix, which in order to provide a comprehensive reference for its continued research.

New triterpene glucosides from the roots of Rosa laevigata Michx.

Two new ursane-type triterpene glucosides, 2alpha,3alpha,24-trihydroxyurs-12,18-dien-28-oic acid beta-D-glucopyranosyl ester (1) and 2alpha,3alpha,23-trihydroxyurs-12,19(29)-dien-28-oic acid beta-D-glucopyranosyl ester (2), were isolated from the roots of Rosa laevigata, together with three known compounds: 2alpha,3beta,19alpha-trihydroxyurs-12-en-28-oic acid beta-Dglucopyranosyl ester (3), 2alpha,3alpha,19alpha-trihydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (4) and 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (5). The structures of new compounds were established on the basis of detailed 1D and 2D NMR spectroscopic analyses. Compounds 2 and 5 exhibited modest in vitro antifungal activities against Candida albicans and C. krusei.

[Studies on chemical constituents of Sarcandra glabra].

OBJECTIVE: To study antibacterial chemical constituents of Sarcandra glabra. METHOD: The constituents of the chloroform and EtOAc-soluble portions of the EtOH extract from the whole plant of S. glabra, which posses the antibacterial activities, were isolated and purified with column chromatography. The compounds were identified by physical and spectroscopic techniques. RESULT: Six compounds were isolated and identified as 4, 4'-biisofraxidin (1), esculetin (2), fraxetin (3), scoparone (4), isofraxidin (5), scopoletin(6), respectively. CONCLUSION: Compound 1 is a novel natural product. Compounds 24 were isolated from the plants of Chloranthaceae for the first time. The antibacterial activities of these six compounds were tested for the first time. Some compounds may have potential for future study and development as plant-derived oral antibacterial agents.

[Studies on flavonoids of Eupatorium odoratum L].

OBJECTIVE: To investigate the flavonoid constituents from aerial parts of Eupatorium odoratum L. systematically. METHODS: The constituents of the EtoAc-soluble portions of the 95% ethanol extraction were isolated and purified by silica gel and sephadex LH-20 chromatography. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. RESULTS: Eight compounds were isolated and identified as kaempferol-3-methoxy (I), rhamnetin (II), tamarixetin (III), quercetin (IV), kaempferol (V), apigenin (VI), luteolin (VII), dihydrokaempferide (VIII). CONCLUSION: Compound I , II and VI were isolated for the first time from genus Eupatorium, and VIII which is rare flavonoid was obtainted for the first time from family Compositae.

Pentacyclic triterpenoids from leaves of Excoecaria agallocha.

A new oleanane-type triterpenoid (1) and five known pentacyclic triterpenoids (2-6) were isolated from the leaves of Excoecaria agallocha. Their structures were elucidated by spectroscopic analyses. The new compound was characterized as 3beta-[(2E,4E)-5-oxo-decadienoyloxy]-olean-12-ene (1). Compounds 1-6 were found inactive in vitro against several human cancer cell lines.

Norcassane- and cassane-type furanoditerpenoids from the seeds of Caesalpinia sappan.

Three novel furanoditerpenoids, norcaesalpinin J (1) featuring an unusual 20-norcassane hydroperoxide and phangininoxys B (2) and C (3) possessing cassane hemiketal skeletons, were isolated from the seeds of Caesalpinia sappan. Their structures were elucidated by extensive spectroscopic methods. All isolates were evaluated for the cytotoxic activities on three human cancer cell lines.

Novel dinorcassane- and cassane-type diterpenes from the seeds of Caesalpinia minax.

Two novel diterpenes, norcaesalpinin I (1) featuring an unusual ring C-contracted dinorcassane and caesalpinin U (2) possessing a highly oxygenated furanocassane skeleton were isolated from the seeds of Caesalpinia minax. Their structures were determined by different spectroscopic methods. A plausible biosynthetic pathway of 1 was proposed. The cytotoxic activity of compounds 1 and 2 against HepG2 and HeLa human tumor cell lines was evaluated.