Six New neo-Clerodane Diterpenoids from Aerial Parts of Scutellaria barbata and Their Cytotoxic Activities

Yang, Guochun; Hu, Jiahui; Li, Bing-Long; Liu, Huan; Wang, Jiayue; Sun, Lixin

doi:10.1055/a-0638-8255

Cited by 17 publications

(12 citation statements)

References 22 publications

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“…Compound 1 (Figure 1) 5.83) to C(3) and C(1'''), HÀ C(7) (δ(H) 5.53) to C(6) and C(1'') revealed that the two nicotinoyloxy groups were attached to C(1) and C(7), respectively. Based on all of the data the structure of compound 1 was established as shown in Figure 1 and compound 1 named as barbatin H.…”

Section: Resultsmentioning

confidence: 99%

“…[1] Phytochemical investigations on S. barbata showed that the main constituents contained flavonoids, [2] terpenoids, [2,3] and polysaccharides. [4] In recent years, a series of neo-clerodane diterpenoids with cytotoxic [5,6] activities had been isolated from S. barbata, which indicated that they might be a potential chemical structure of antitumor agent. However, very few concrete studies had reported on the effects of those different structural neo-clerodane diterpenoids on cytotoxicity against human cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Neo‐Clerodane Diterpenoids from Scutellaria barbata D.Don

Wang

Chen³

et al. 2019

Chemistry & Biodiversity

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A new neo-clerodane diterpenoid, barbatin H (1), together with fifteen known analogues (2 -16) were isolated from Scutellaria barbata D.DON. Their structures were determined on the basis of NMR and HR-MS spectral analysis and comparison with the reported data. All of those compounds were comparatively predicted for their cytotoxic activities against four human tumor cell lines, i. e. LoVo (colon cancer), MCF-7 (breast cancer), SMMC-7721 (hepatoma cancer), and HCT-116 (colon cancer) cells by MTT method in vitro. The results turned out that the series of neo-clerodane diterpenoids exhibited varying degrees of cytotoxic activities against the growth of the tested tumor cell lines, and most of them exhibited selective cytotoxicity against LoVo cell lines. Scutebata A (14) showed significant cytotoxic activities against four tested tumor cells with IC 50 values of 4.57, 7.68, 5.31, and 6.23 μM, respectively, which indicated that it might be a potential chemotherapeutic agent.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cytotoxic Neo‐Clerodane Diterpenoids from Scutellaria barbata D.Don

Wang

Chen³

et al. 2019

Chemistry & Biodiversity

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“…Moreover, phenylpropanoids [70,80], phenolic compounds, saccharides, and steroids have been isolated from RC [50,51,[80][81][82][83]. It was reported that diterpenoids [84,85] and essential oils [86] were also found in RS. In addition to alkaloids, CP also contains sterols, esters, triterpenes and other compounds [87][88][89][90].…”

Section: Other Chemical Componentsmentioning

confidence: 99%

Huang-Lian Jie-Du decoction: a review on phytochemical, pharmacological and pharmacokinetic investigations

Zhang

Zhu

2019

Chin Med

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Huang-Lian Jie-Du decoction (HLJDD), a famous traditional Chinese prescription constituted by Rhizoma Coptidis, Radix Scutellariae, Cortex Phellodendri and Fructus Gradeniae, has notable characteristics of dissipating heat and detoxification, interfering with tumors, hepatic diseases, metabolic disorders, inflammatory or allergic processes, cerebral diseases and microbial infections. Based on the wide clinical applications, accumulating investigations about HLJDD focused on several aspects: (1) chemical analysis to explore the underlying substrates responsible for the therapeutic effects; (2) further determination of pharmacological actions and the possible mechanisms of the whole prescription and of those representative ingredients to provide scientific evidence for traditional clinical applications and to demonstrate the intriguing molecular targets for specific pathological processes; (3) pharmacokinetic feature studies of single or all components of HLJDD to reveal the chemical basis and synergistic actions contributing to the pharmacological and clinically therapeutic effects. In this review, we summarized the main achievements of phytochemical, pharmacological and pharmacokinetic profiles of HLJDD and its herbal or pharmacologically active chemicals, as well as our understanding which further reveals the significance of HLJDD clinically.

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“…Diterpenoid alkaloids are the most widely reported compounds from S. barbata with cytotoxic activities tested on cancer cell lines. Their in vitro cytotoxicities have been identified on at least one of the following cancer cell lines including HONE-1 nasopharyngeal, KB oral epidermoid carcinoma, HT29 colorectal carcinoma, 19 -22,29,30,35 -37,39,53,54 HL-60 leukemia, 27,31,32,40 SK-BR-3 breast adenocarcinoma, 32 K562 erythromyeloblastoid leukemia, HepG2 and SMMC-7721 hepatocellular carcinoma, 3,23,24,39 A549 lung adenocarcinoma, 3,23 LNCaP prostate cancer, SK-MEL-2 melanoma, 39 MCF-7 breast adenocarcinoma, 24,37,39 SGC7901 gastric cancer, 33 LoVo, 24 HCT-116, 24,28 and SW480 colon adenocarcinoma cells 32 with IC 50 values ranging from 2.0 to over 100 µM. The 6-(2,3-epoxy-2-isopropyl- n -propoxyl) barbatin C (Figure 3) was the most cytotoxic neo-clerodane diterpenoid reported so far with IC 50 as low as 2.0 µM to KB oral epidermoid cancer cells.…”

Section: Phytochemical and Pharmacological Properties Of Scutellaria Barbatamentioning

confidence: 99%

From Scutellaria barbata to BZL101 in Cancer Patients: Phytochemistry, Pharmacology, and Clinical Evidence

Gao

Yin

Corcoran

2019

Natural Product Communications

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Scutellaria barbata D.Don is a popular Chinese medicinal plant documented to treat cancer patients in traditional Chinese medicine (TCM). A botanical new investigational drug for breast cancer BZL101 (FDA IDN# 59521) was previously developed in the United States from the aqueous extract of the aerial parts from S. barbata. The early phase 1A and 1B clinical trials show its favorable toxicity profiles, good clinical tolerance, and promising efficacy for patients with metastatic breast cancer. To further evidence the phytopharmacology research, drug development, and anticancer use of this herb, a systematic literature review was performed herein on the phytochemistry, pharmacology, and specifically anticancer clinical evidence. A systematic review of the literature on phytochemical and pharmacological properties of the plant related to cancer treatment employed several web-based scientific databases including Wanfang (Chinese), Pubmed, Web of Science, and Elsevier. Key words included Scutellaria barbata, Ban Zhi Lian, cancer, and tumor. Based on critical quality criteria, only 8 out of 69 reports related to clinical studies of cancer patients in China. This review covered the available literature up to July 2019. The anticancer effects of S. barbata can be explained by the presence of various flavonoids and diterpenoids alkaloids. The underlying mechanisms are primarily summarized as cyclin/cyclin-dependent kinase (CDK)-modulated cell cycle arrest and mitochondria-mediated apoptotic death. The highly cancer-cell selective cytotoxicity and detoxifying effects of S. barbata contribute to a favorable clinical profile and enhanced quality of life for the cancer patient, thereby demanding further study as an adjuvant or alternative to conventional chemotherapy. The phytochemical and pharmacological studies reviewed strongly underpin a fundamental understanding of the anticancer activity of S. barbata and support ongoing clinical trials. The further safety verification and clinical trials are expected to progress S. barbata-based development to finally transform the traditional TCM herb S. barbata to the valuable anticancer drug.

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Six New neo-Clerodane Diterpenoids from Aerial Parts of Scutellaria barbata and Their Cytotoxic Activities

Cited by 17 publications

References 22 publications

Cytotoxic Neo‐Clerodane Diterpenoids from Scutellaria barbata D.Don

Cytotoxic Neo‐Clerodane Diterpenoids from Scutellaria barbata D.Don

Huang-Lian Jie-Du decoction: a review on phytochemical, pharmacological and pharmacokinetic investigations

From Scutellaria barbata to BZL101 in Cancer Patients: Phytochemistry, Pharmacology, and Clinical Evidence

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