Novel Terpenoids from <i>Calocedrus macrolepis</i> var. <i>formosana</i>

Hsieh, Chin‐Lin; Tseng, Mei‐Hui; Pan, Ryh‐Nan; Chang, Jang‐Yang; Kuo, Ching‐Chuan; Lee, Tzong‐Huei; Kuo, Yueh‐Hsiung

doi:10.1002/cbdv.201000237

Cited by 8 publications

(3 citation statements)

References 14 publications

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“…formosana ) belonging to the Cupressaceae family, has been used to make incense since ancient times in Taiwan. More than 100 compounds have been isolated from the plant, including monoterpenoids, diterpenoids, lignans, and steroids [ 15 , 16 ]. The compounds of C. formosana possessed the diverse activities, such as anti-oxidative [ 17 , 18 ], anti-termitic and anti-fungal [ 19 ], anti-inflammatory [ 20 ], and anti-cancer [ 21 ] properties.…”

Section: Introductionmentioning

confidence: 99%

Anti-Melanogenic Activity of Calocedrus formosana Wood Essential Oil and Its Chemical Composition Analysis

Hsiao

Kumar

Lee

et al. 2021

Plants

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Calocedrus formosana (Cupressaceae) is one of the five precious woods of Taiwan. In this study, we investigated the anti-melanogenic activity of C. formosana wood essential oil (CFEO) and its bioactive components in vitro. Initially, CFEO exhibited strong mushroom tyrosinase activity in the cell-free mushroom tyrosinase assay system with an IC50 value of 2.72 µg/mL. Next, treatment with CFEO significantly as well as dose-dependently reduced a combination of a-melanocyte-stimulating hormone and forskolin (a-MSH-FSK)-induced melanin synthesis in B16-F10 cells. Indeed, 80 mg/mL CFEO completely inhibited melanin production, which is similar to that of control cells. Further studies revealed that treatment with CFEO significantly inhibited melanogenesis regulatory proteins, including TRP-1, TRP-2, and MITF, whereas tyrosinase was unaffected by either a-MSH-FSK or CFEO. In addition, the composition of the CFEO was characterized. The major components of CFEO were α-terpineol (23.47%), shonanic acid (10.45%), terpinen-4-ol (12.23%), thymol (5.3%), piperitone (3.44%), berbenone (2.81%), thujic acid (1.65%), and chaminic acid (0.13%). Among them, shonanic acid (1), thujic acid (2), and chaminic acid (3) were uncommon constitutes in essential oils, which could be the index compounds of CFEO, and the structure of these compounds were confirmed by spectral analysis. Furthermore, we found that thymol is an active ingredient responsible for CFEO’s anti-melanogenic activity. Based on these results, we suggest that CFEO or thymol could be a potential candidate for the development of skin whitening products for cosmetic purposes.

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Section: Introductionmentioning

confidence: 99%

Anti-Melanogenic Activity of Calocedrus formosana Wood Essential Oil and Its Chemical Composition Analysis

Hsiao

Kumar

Lee

et al. 2021

Plants

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“…formosana . Results of the study indicated that ferrugimenthenol displayed potent activity against human oral epidermoid carcinoma cells ( Hsieh et al, 2011 ). Qin et al isolated myrtucommulone D, isomyrtucommulone B, and callisalignenes G–I from the Callistemon salignus leaves and twigs.…”

Section: Biological Activities Of Meroterpenoidsmentioning

confidence: 99%

Biological activities of meroterpenoids isolated from different sources

et al. 2022

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Meroterpenoids are natural products synthesized by unicellular organisms such as bacteria and multicellular organisms such as fungi, plants, and animals, including those of marine origin. Structurally, these compounds exhibit a wide diversity depending upon the origin and the biosynthetic pathway they emerge from. This diversity in structural features imparts a wide spectrum of biological activity to meroterpenoids. Based on the biosynthetic pathway of origin, these compounds are either polyketide-terpenoids or non-polyketide terpenoids. The recent surge of interest in meroterpenoids has led to a systematic screening of these compounds for many biological actions. Different meroterpenoids have been recorded for a broad range of operations, such as anti-cholinesterase, COX-2 inhibitory, anti-leishmanial, anti-diabetic, anti-oxidative, anti-inflammatory, anti-neoplastic, anti-bacterial, antimalarial, anti-viral, anti-obesity, and insecticidal activity. Meroterpenoids also possess inhibitory activity against the expression of nitric oxide, TNF- α, and other inflammatory mediators. These compounds also show renal protective, cardioprotective, and neuroprotective activities. The present review includes literature from 1999 to date and discusses 590 biologically active meroterpenoids, of which 231 are from fungal sources, 212 are from various species of plants, and 147 are from marine sources such as algae and sponges.

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“…Our long-term studies on the C. macrolepis var. formosana have identified plentiful secondary metabolites with cytotoxicity toward human oral epidermoid carcinoma KB cells [ 13 , 16 , 17 ], which prompted us to further explore its ingredients as the source of cytotoxic compounds.…”

Section: Introductionmentioning

confidence: 99%

Anti-lymphangiogenic diterpenes from the bark of Calocedrus macrolepis var. formosana

Lee¹,

Hsieh²,

Wu³

et al. 2021

Journal of Food and Drug Analysis

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Eight new diterpenes, 6α,7β-dihydroxyferruginol (1), 6α,7α-dihydroxyferruginol (2), 6α-hydroxyhinokiol (3), 4α-hydroxy-7-oxo-18-norabieta-8,11,13-trien-4α-ol (4a), 15,16-dehydrosugiol (5), 7-methoxy-6,7-secoabieta-8,11,13-triene-6,12-diol (6), 7α-acetoxyabieta-8,12-diene-11,14-dione (7), 7α-butyloxyethyloxyabieta-8,12-diene-11,14-dione (8), along with four known compounds, 6,7-dehydroferruginol (9), 12-hydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial (10), 7α-11-dihydroxy-12-methoxy-8,11,13-abietatriene (11), and 11,14-dihydroxy-8,11,13-abietatrien-7-one (12) were successfully isolated from the bark of Calocedrus macrolepis var. formosana . The structures of all isolates were elucidated by physical data (appearance, UV, IR, optical rotation) and spectroscopic data (1D, 2D NMR, and HREIMS). Compounds 9, 10, 11, and 12 showed promising growth-inhibitory effect on human lymphatic endothelial cells (LECs). Among these compounds, compound 10 exerted the most potent anti-lymphangiogenesis property by suppressing cell growth and tube formation of LECs. In conclusion, the results revealed the anti-lymphangiogenic potentials of Formosan C. macrolepis var. formosana .

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Novel Terpenoids from Calocedrus macrolepis var. formosana

Cited by 8 publications

References 14 publications

Anti-Melanogenic Activity of Calocedrus formosana Wood Essential Oil and Its Chemical Composition Analysis

Anti-Melanogenic Activity of Calocedrus formosana Wood Essential Oil and Its Chemical Composition Analysis

Biological activities of meroterpenoids isolated from different sources

Anti-lymphangiogenic diterpenes from the bark of Calocedrus macrolepis var. formosana

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