Sesquiterpene lactones and other constituents from Siegesbeckia orientalis and Guizotia scabra

doi:10.1016/0031-9422(91)84212-B

Phytochemistry

Volume 30, Issue 5, 1991, Pages 1579-1584

https://doi.org/10.1016/0031-9422(91)84212-B Get rights and content

Abstract

From the aerial parts of Siegesbeckia orientalis, in addition to a known sesquiterpene lactone, nine new germacranolides, three melampolides, three geranylnerol derivatives and three ent-pimarenes were isolated. From Guizotia scabra a new eudesmanolide was obtained. The structures were elucidated by high field NMR techniques. The chemotaxonomic aspects are discussed briefly.

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Cited by (38)

Herba Siegesbeckiae: A review on its traditional uses, chemical constituents, pharmacological activities and clinical studies
2021, Journal of Ethnopharmacology
Citation Excerpt :
According to the different oxygen-containing substituents of kaurenoids, Zhang et al. (1990) summarized the regular change of chemical shift of each carbon atom in 13C-NMR spectrum, which provided a reference for the position and orientation of substituents. To date, three chains diterpenes (Table 5, Fig. 5, 82–84) were discovered from HS (Zdero et al., 1991). However, studies of chain diterpenoids have been poorly researched.
Herba Siegesbeckiae, mainly includes Sigesbeckia orientalis L, Sigesbeckiae pubescens Makino and Sigesbeckiae glabrescens Makino. Herba Siegesbeckiae, also known as ‘Xi-Xian Cao’ (Chinese: 豨莶草), has been regarded as an important traditional Chinese medicine since Tang dynasty. The dried aerial parts of Herba Siegesbeckiae are also being used as a herbal medicine in many countries such as Japan, Korea and Vietnam. In China, Herba Siegesbeckiae has been used for the treatment of rheumatic arthralgia with aching and weakness of loins and knees, as well as numbness of limbs.
The aim of this review was to provide critical analysis on the scientific evidence to support the traditional uses of Herba Siegesbeckiae. The information available on its in botanical characteristics, traditional uses, chemical constituents, pharmacological activities, clinical studies, toxicity and quality control was summarized to understand the current research and provided the leas for future study.
The search terms “Herba Siegesbeckiae”, “Sigesbeckia orientalis”, “Sigesbeckia pubscens” and “Sigesbeckia glabrescens” were used to obtain the information from electronic databases such as Web of Science, China National Knowledge Infrastructure, PubMed, Google Scholar and SciFinder Scholar and other web search instruments (Springer, Yahoo search). The information provided in this review was based on peer-reviewed papers in English and Chinese. Besides, information was also collected from ancient documents.
The studies showed that Herba Siegesbeckiae contains sesquiterpenoids, diterpenoids, flavonoids and organic acids, etc. Due to these constituents, it displayed numerous pharmacological activities, such as anti-inflammatory, antitumor, antiallergic, antioxidant, antithrombotic and antibacterial activities. In addition, it showed effects in protecting myocardial and cerebral ischemia injury.
According to its traditional uses, chemical constituents, pharmacological activities and clinic studies, Herba Siegesbeckiae is regarded as a promising medical plant with various chemical compounds and numerous pharmacological activities. However, fewer experimental studies were focused on toxicity and quantitative study of 3 species. It suggested that further in-depth study of toxicity and quality control were critical for future evaluation of drug efficacy and safety.
Diverse diterpenoids and sesquiterpenoids from Siegesbeckia pubescens and their activity against RANKL-induced osteoclastogenesis
2021, Bioorganic Chemistry
Citation Excerpt :
One carbonyl and four double bonds accounted for five unsaturated degrees, which suggested 16 is an acyclic compound. Its NMR data was similar to those of reported acyclic diterpenoids [22]. The COSY cross-peaks (Fig. 2) indicated three spin systems of H2-1 (δH 4.03)/H-2 (δH 5.43)/H3-20 (δH 1.72), H2-4 (δH 2.11)/H2-5 (δH 2.18)/H-6 (δH 5.30)/H2-19 (δH 4.10), and H2-8 (δH 2.30)/H2-9 (δH 2.42)/H-10 (δH 6.68)/H3-18 (δH 1.82).
Phytochemical investigation of the aerial parts of Siegesbeckia pubescens led to seventeen diterpenoids (1–17) and twelve sesquiterpenoids (18–29). Their structures were varied including twelve ent-pimarane (1–12), three ent-kaurane (13–15), two acyclic diterpenoids (16–17), ten germacrene (18–27), one guaiane (28), and one caryolane (29) sesquiterpenoids. Eight of twenty-nine were new ones (1, 3, 4, 16–18, 23, and 28). Their structures were elucidated by extensive spectroscopic analysis. The absolute configurations of compounds 1 and 2 were identified using X-ray diffraction analysis, and of compounds 18, 23, and 28 were elucidated by the experimental and calculated electronic circular dichroism (ECD) spectra. All the isolated compounds (1–29) were assayed for their inhibition of RANKL-induced osteoclastogenesis in bone marrow macrophages (BMMs). Four sesquiterpenoids 18, 25, 26, and 27 exhibited potent inhibition of osteoclastogenesis with IC₅₀ value of 0.51, 0.80, 0.50, and 0.83 μM, respectively. Here we demonstrated that S. pubescens may be a resource for discovery of anti-osteoporosis agents.
Six novel lignanoids with complex structures from Sigesbeckia glabrescens Makino with their cytotoxic activities
2021, Fitoterapia
Citation Excerpt :
Modern pharmacological studies have clearly shown that the extracts of Sigesbeckiae Herba exhibited anti-inflammatory [3,4], anti-allergic [5], immunosuppressive [6,7], antithrombotic [8], anti-tumor [9] and other activities [10,11]. Previous chemical studies of this plant have revealed the presence of diterpenoids [12,13], sesquiterpenoids [14–16] and flavonoids [17,18]. However, there have been no reports of lignans in this herb.
Six new lignanoids, Glalignin A-E (1–5) and Glaneolignin A (6), together with four analogues, (+)-isolariciresinol (7), (+)-syringaresinol (8), dihydrodehydrodiconiferyl alcohol (9) and tribulusamide A (10), were obtained from the aerial parts of Sigesbeckia glabrescens Makino and also isolated for the first time from the Sigesbeckia genus. The structures of these compounds were elucidated by the interpretation of HRESIMS, 1D NMR, 2D NMR data and chemical evidence. The cytotoxic activities of the compounds were evaluated by testing their inhibition in several tumor cells using the MTT assay. New compound 2 and 5 displayed cytotoxicity against the human cancer cell lines human lung adenocarcinoma cells (A549) with IC₅₀ values of 32.89 ± 6.83 and 35.86 ± 6.83 μM.
A selection of eleven plants used as traditional Polynesian cosmetics and their development potential as anti-aging ingredients, hair growth promoters and whitening products
2019, Journal of Ethnopharmacology
In French Polynesia, embellishment of the hair and skin is an important cultural and everyday practice. Yet, little research has focused on traditional preparations used for beautification in this region and their potential development as innovative cosmetic ingredients.
In this present study we aim to assess and compile the ethnocosmetic potential of plants of French Polynesia to select and further study plants showing the most promise to be developed as anti-aging, anti-blemish and hair care products.
A literature analysis of plants of the IECIC list, present in French Polynesia was conducted. The most interesting plants from a cosmetic development standpoint were selected based on four main criteria, i.e. their traditional use in Polynesian cosmetic-related preparations, their biogeographical status, their phytochemistry of cosmetic interest, and lastly their availability and absence from the UICN list. Furthermore, a preliminary screening of antioxidant and anti-inflammatory activities was also performed on several extracts obtained.
Eleven plants were chosen, and a compilation of multidisciplinary data emphasized each selected plant's potentiality. Traditional allegations showed uses ranging from dermatology such as wound healing or anti-inflammatory properties, to hair growth promoting preparations or even skin ligthening ones. Preliminary screenings were useful in narrowing the number of extracts to study. Literature-based data associated to traditional uses depicted how the remaining plants and plant parts could be developed for targeted cosmetic applications.
A prospective approach of plants used traditionally for cosmetic purposes in French Polynesia gave insight on their development potential when paired with the appropriate multidisciplinary data. The eleven plants presented show promise in being developed sustainably as natural anti-aging or hair care products and as skin brightening agents.
Germacrane-type sesquiterpenoids with cytotoxic activity from Sigesbeckia orientalis
2019, Bioorganic Chemistry
Citation Excerpt :
The calculated ECD spectrum of 11 displayed similar cotton effects to the experimental ECD curve (Fig. 4), allowing the assignment of the absolute configuration as 6R,7R,8S,9S. Compounds 12–28 were identified as (4β,10E)-6α,14,15-trihydroxy-8β-(isobutyryloxy)germacra-10,11(13)-diene-12-oic acid 12,6-lactone (12) [14], 2-propenoic acid, 2-methyl-2,3,3a,4,5,8,9,10,11,11a-decahydro-6,10-bis(hydroxymethyl)-3-methylene-2-oxocyclodeca[b]furan-4-yl ester (13) [16], (1(10)E,4β)-8β-(angeloyloxy)-6α,14,15-trihydroxygermacra-1(10),11(13)-diene-12-oic acid 12,6-lactone (14) [10], 9α-ethoxy-8β-(2-isobutyryloxy)-14-oxo-acanthospermolide (15) [17], (1(10)E,4Z,6α,8β,9α)-9-ethoxy-6,15-dihydroxy-8-(2-methylacryloxy)-14-oxogermacra-1(10),4,11(13)-trieno-12,6-lactone (16) [18], (2Z)-2-methylbut-2-enoic acid (3aS,4S,5S,6E,10Z,11aR)-5-(ethoxy)-6-formyl-2,3,3a,4,5,8,9,11a-octahydro-10-(hydroxymethyl)-3-methylene-2-oxocyclodeca[b]furan-4-yl ester (17) [10], (1(10)E,4Z)-9α,15-dihydroxy-8β-isobutyryloxy-14-oxo-melampolide (18) [19], (1(10)E,4Z,6α,8β,9α)-6,9,15-trihydroxy-8-(methylacryloxy)-14-oxogermacra-1(10),4,11(13)-trieno-12,6-lactone (19) [18], lecocarpinolide F (20) [20], sigesbeckialide A (21) [4], (3aS,4S,5S,6Z,10Z,11aR)-5-(acetyloxy)-2,3,3a,4,5,8,9,11a-octahydro-6,10-bis(hydroxymethyl)-3-methylene-2-oxo-cyclodeca[b]furan-4-yl ester (22) [21], orientalide (23) [22], lecocarpinolide B (24) [23], pubetallin (25) [11], (1(10)E,4Z)-8β-(angeloyloxy)-9α-methoxy-6α,15-dihydroxy-14-oxogermacra-1(10),4,11(13)-trien-12-oic acid 12,6-lactone (26) [24], 9α-Hydroxy-8β-methacryloyloxy-14-oxo-acanthospermolide (27) [25], and 3β-hydroxybalchanolide (28) [26], respectively, based on the comparisons of NMR and MS data with reported values. All the compounds except 5 and 24, which were obtained only in a limited amount, were assayed for their cytotoxicity against human MDA-MB-231 (breast) and A549 (lung) cancer cell lines with adriamycin as a positive control (Table 4).
Eleven new highly oxygenated germacrane-type sesquiterpenoids (1–11) and 16 known analogues (12–27) were isolated from the aerial parts of Sigesbeckia orientalis. Their structures, including absolute configurations, were determined by comprehensive spectroscopic methods especially NMR and ECD analyses. Compounds 13, 21 and 23 possessing an 8-methacryloxy group showed stronger in vitro cytotoxicity against human A549 and MDA-MB-231 cancer cell lines than other co-metabolites, with IC₅₀ values ranging from 6.02 to 10.77 μM comparable to the positive control adriamycin.
Isolation and characterization of diterpene glycosides from Siegesbeckia pubescens
2017, Bioorganic and Medicinal Chemistry Letters
Five new diterpenoid glycosides, siegesides A–E (1–5), along with the known compound darutoside (6) were isolated and characterized from the ethanol extract of Siegesbeckia pubescens. The structural elucidation of the isolates was accomplished by extensive HRESIMS and NMR analysis. Compounds 1 and 2 are epimers of 6. All isolates were evaluated for their inhibition on the migration of MB-MDA-231 breast cancer cells induced by the chemokine epithelial growth factor, and compound 2 showed superior inhibitory activities in comparison with the positive control drug with IC₅₀ value of 0.27 μM.

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Sesquiterpene lactones and other constituents from Siegesbeckia orientalis and Guizotia scabra

Abstract

Compt. Rend.

J. Org. Chem.

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Bot. Rev.

Smithsonian Contr. Botany

Tetrahedron Letters

Tetrahedron Letters