Garmultins A–G, Biogenetically Related Polycyclic Acylphloroglucinols from <i>Garcinia multiflora</i>

Tian, Dong Song; Yi, Ping; Xia, Lei; Xiao, Xin; Fan, Yi; Gu, Wei; Huang, Lie Jun; Ben‐David, Yaacov; Di, Ying; Yuan, Chun Mao; Hao, Xiao Jiang

doi:10.1021/acs.orglett.6b03004

Cited by 59 publications

(45 citation statements)

References 24 publications

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“…Polycyclic polyprenylated cyclophloroglucinols (PPAPs) are a class of secondary metabolites that contain a highly functionalized bicyclic core and possess many interesting and potentially useful bioactivities. Because of their anticancer, antiviral, and antibacterial properties, PPAPs and their analogs are of interest as leads for drug discovery and have been the subject of synthesis by organic and medicinal chemists . Recently, and for the first time, an enantiomeric pair of PPAPs was isolated from Garcinia multiflora ((+) and (−) 24 ) .…”

Section: Discussionmentioning

confidence: 99%

Biomimetic syntheses of racemic natural products

Zask

Ellestad

2017

Chirality

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Racemic natural products are rarely produced in plants and microorganisms and are thought to be the result of nonenzymatic, spontaneous reactions. These compounds are often highly complex with multiple contiguous chiral centers that present a challenge to organic synthesis. Formation of these racemates often occurs by cyclization reactions that can generate multiple stereocenters from achiral precursors. Biomimetic synthesis of these racemic natural products provides support for their proposed nonenzymatic spontaneous biosynthesis. These elegant syntheses also provide scalable and efficient routes to these complex natural products. Although the number of reported racemic natural products is relatively low, an isolated natural product that has a very small optical rotation has been shown to be a true racemate. Thus, the occurrence of racemic natural products could be more common than thought.

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Section: Discussionmentioning

confidence: 99%

Biomimetic syntheses of racemic natural products

Zask

Ellestad

2017

Chirality

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“…Compounds (−)-garmultin C, (+)-garmultin C and (−)-garmultin D are novel PPAPs (Figure 11), and were evaluated of showing strong Fli-1 inhibitory activity in HEL cells. Indeed, it was the first time for PPAPs inhibiting Fli-1 protein (Tian et al, 2016).…”

Section: Plant Natural Product Inhibitors Of Friend Leukemia Integratmentioning

confidence: 99%

Natural product sciences: an integrative approach to the innovations of plant natural products

Shen

Hao

2020

Sci. China Life Sci.

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The study on plant natural products not only helps us understand that their structural diversity is the inevitable result of plant species diversity, but also helps us understand certain rules and unity of the inevitable connection between the two. The diversity and complexity of chemical structures of many natural products are beyond imagination before we elucidated their structures. The question that follows is what is the biological significance of these natural products. Intrigued by the relationship between plant resources, natural products and biological functions, the Hao laboratory has taken an integrative approach that employs tools and knowledge from multi-disciplines, including natural product chemistry, chemical ecology and chemical biology, to unveil the effects of plant natural products on plant resistance to diseases, and environmental acclimations. Collaborating with cell biologists, the research has resulted in discovery of new mechanisms of cellular signaling and lead compounds.

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“…Garcinia multiflora was the source of (±)-garcimulins A ((±)- 662 ) and B ( 663 ) as well as (±)-garmultin A ((±)- 664 ) and (–)-garmultin B ((–)- 665 ). (±)-Garcimulins A ((±)- 662 ) and B ( 663 ) included a tetracyclo[5.4.1 1, 5 .1.0 9, 13 ]tridecane skeleton (Fan et al, 2015a ), while (±)-garmultin A ((±)- 664 ) and (–)-garmultin B ((–)- 665 ) coupled a 2,11-dioxatricyclo[4.4.1.0 3, 9 ] undecane and a tricyclo [4.3.1.0 3, 7 ]decane (Tian et al, 2016a ). Thirteen enmein-type ent -kaurane diterpenoids were obtained from aerial parts of Isodon phyllostachys (Sichuane, China), among which phyllostacins J ( 666 ) and K ( 667 ) were the first examples of 3,20:6,20-diepoxyenmein-type ent -kauranoids (Yang et al, 2016e ).…”

Section: Terrestrial Plantsmentioning

confidence: 99%