China
Africa
Explore chapters and articles related to this topic
Biotransformation of Sesquiterpenoids, Ionones, Damascones, Adamantanes, and Aromatic Compounds by Green Algae, Fungi, and Mammals
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Yoshinori Asakawa, Yoshiaki Noma
(−)-Polygodial (293) possessing piscicidal, antimicrobial, and mosquito-repellant activity is the major pungent sesquiterpene dial isolated from Polygonum hydropiper and the liverwort Porella vernicosa complex. Polygodial was incubated with A. niger; however, because of its antimicrobial activity, no metabolite was obtained (Sekita et al., 2005). Polygodiol (295) prepared from polygodial (293) was also treated in the same manner as described earlier to afford 3β-hyrdoxy (297), which was isolated from Marasmius oreades as antimicrobial activity (Ayer and Craw, 1989), and 6α-hydroxypolygodiol (298) in 66%–70% and 5%–10% yields, respectively (Aranda et al., 1992). The same metabolite (297) was also obtained from polygodiol (295) as a sole metabolite from the culture broth of A. niger in Czapek-peptone medium for 3 days in 70.5% yield (Sekita et al., 2005), while the C9 epimeric product (296) from isopolygodial (294) was incubated with M. plumbeus to afford 3β-hydroxy- (299) and 6α-hydroxy derivative (300) in low yields, 7% and 13% (Aranda et al., 1992). Drim-9α-hydroxy-11β,12-diacetoxy-7-ene (301) derived from polygodiol (295) was treated in the same manner as described earlier to yield its 3β-hydroxy derivative (302%, 42%) (Sekita et al., 2005) (Figures 23.91 and 23.92).
Biologically Active Substances From Bryophytes
Published in R. N. Chopra, Satish C. Bhatla, Bryophyte Development: Physiology and Biochemistry, 2019
Table 15 shows the piscicidal activity of terpenoids isolated from some liverworts against the killifish (Oryzia latipes).16 The strongest piscicidal compounds are the pungent polygodial (21) and sacculatal (22).13-18, 96 The fish is killed within 2 h by a 0.4 ppm solution and within 20 min by a 7 ppm solution of 21 and 22. The killifish is also killed within 2 h by a 0.4 ppm solution of non-natural (+ )-polygodial (124) possessing a potent hot taste.18 Thus, it is confirmed that piscicidal activity against the killifish is not affected by chiral specificity of 21 and 124. Polygodial (21) is very toxic against bitterling fish, which are killed within 3 min by a 0.4 ppm solution.18 Some mosquito larvae are killed within 4 h by a 40 ppm solution of 21.16 On the other hand, isosacculatal (25) and isopolygodial (125) (which has been obtained from Polygonum hydropiper) lack fish-killing activity even in a 10,000 ppm solution.13-18 From the above results it is obvious that the occurrence of piscicidal activity of polygodial and sacculatal is significantly related to hot taste, that is, the absolute configuration of a formyl group at C-9. Costunolide (136) isolated from Marchantia polymorpha also possesses weak piscicidal activity (TLm = 2 ppm) against the killifish.97
Food Preservation and the Antimicrobial Activity of Australian Native Plants
Published in Yasmina Sultanbawa, Fazal Sultanbawa, Australian Native Plants, 2017
Polygodial is the principal antimicrobial compound in Tasmanian pepper leaf extracts and is very effective against fungi (Table 19.3). The fungicidal activity of polygodial was significantly increased when combined with anethole and sorbic acid, indicating a synergistic effect of these compounds (Fujita and Kubo, 2005a,b).
Antifouling activity of portimine, select semisynthetic analogues, and other microalga-derived spirocyclic imines
Published in Biofouling, 2018
Darby G. Brooke, Gunnar Cervin, Olivier Champeau, D. Tim Harwood, Henrik Pavia, Andrew I. Selwood, Johan Svenson, Louis A. Tremblay, Patrick L. Cahill
The relative potency of 1 matches or exceeds that of modern commercial AF biocides, marine natural product antifoulants, and relevant terrestrial phytochemicals assessed similarly in laboratory bioassays. The biodegradable settlement inhibitors Sea-Nine™ 221N and Selektope™ have EC50 values determined in laboratory bioassays based on macrofouling organisms of around 300 ng ml−1 (Trepos et al. 2015) and 2 ng ml−1 (Dahlström & Elwing 2006), respectively. The most potent compound in a recent meta-analysis of almost 200 macroinvertebrate derived antifouling natural products was the diterpenoid pukalide, which is produced by a gorgonian coral and has an EC50 against A. amphitrite of 19 ng ml−1 (Gerhart & Coll 1993; Qi & Ma 2017). Terrestrial phytochemicals that have been assessed for marine AF activity include batatasin-III and polygodial; these compounds are effective against a range of micro and macrofoulers down to ∼1 µg ml−1 (Moodie et al. 2017a) and 5 ng ml−1 (Moodie et al. 2017b), respectively. Notwithstanding differences in methodology between studies and likely incomplete data coverage, the potency values calculated here are consistent with 1 being a best-in-class natural product AF lead compound.
The traditional herb Polygonum hydropiper from China: a comprehensive review on phytochemistry, pharmacological activities and applications
Published in Pharmaceutical Biology, 2023
Yi-Dan Kong, Ying Qi, Na Cui, Zhi-Hong Zhang, Na Wei, Chang-Fu Wang, Yuan-Ning Zeng, Yan-Ping Sun, Hai-Xue Kuang, Qiu-Hong Wang
To date, a total of 324 compounds have been isolated and identified from PH, mainly flavonoids, phenylpropanoids, volatile oils, terpenoids and organic acids. Among them, flavonoids and volatile oil components have certain antibacterial and antiviral effects, but the active ingredients and pharmacodynamic substance basis have not been reported. The volatile oil component ‘eugenol’ was found to be a pesticide, and the insecticidal mechanism was that eugenol significantly inhibited the activities of acetylcholinesterase and glutathione-S-transferase (Zeng 2007). The second volatile oil component ‘confertifolin’ was considered for use in the control of human vector mosquitoes, but the mechanism is unclear (Maheswaran and Ignacimuthu 2013). Confertifolin is very promising for formulating a potent and affordable natural product to control dreadful disease transmission and nuisance-creating human vector mosquitoes. The other active insecticidal components were crude extracts. In general, the study of PH remains inadequate. Quercetin is an anti-inflammatory active ingredient, and its mechanism is that it inhibits the Src/Syk/NF-κB and IRAK/AP-1/CREB signaling pathways. It has been suggested that quercetin should be developed as a novel anti-inflammatory remedy (Yang et al. 2012). In particular, there is a lack of toxicity research. To date, only a few studies have reported that the flavonoids of PH have no acute toxicity and are nontoxic after long-term use. However, there is a lack of reports of other active components, especially volatile oil and terpenoid components. When used as pesticides, there is also a lack of reports on the optimal concentration and dose of pesticides for various pests and whether there is harm to the human body when used as pesticides. In ancient China, people often burned PH at night to repel mosquitoes and insects, and this practice could match the insecticidal effect in modern pharmacological research. The polygodial contained in PH is a volatile terpenoid, has good antifeedant activity to insects, and has antioxidation, good stability to air and light, and a half-life of more than one month. It is less stable to heat but has a half-life of more than 15 days, which is different from other herbs (Zhang 2004). While the current study only reported that the active ingredients of PH with insecticidal effects are volatile oils and some crude extracts, the active compounds have not been determined. High-temperature burning has a pungent odor, and whether the insecticidal mechanism is related to the pungent odor is unknown, so the subsequent research should involve more in-depth screening of the active substances with insecticidal effects, which can be developed into pesticides and insecticides of plant origin.